Derivatives ethers of bisphenol a, stable composition and method for stabilizing a polymer

 

(57) Abstract:

The invention relates to stabilizers for organic materials against oxidative, thermal or light degradation. As stabilizers use derivatives ethers of bisphenol a General formula I

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where R1and R2for example, WITH1-C5-alkyl, C5-C12-cycloalkyl, phenyl, alkylphenyl-CH2-S-X:

R3-R8is hydrogen, alkyl or phenyl;

n = 1 or 2, if n = 1, And, for example, alkoxyalkyl, -O-Z1, -N(Z2)(Z3), NH(OZ4), -S(O)mZ7-or-O-N = C(Z5)(Z)6if n = 2, then A, for example, diamine, including2-C8-alkylen,2-C12-alkylen, interrupted in the chain by oxygen or WITH7-C9-phenylalkyl, and Z1for example, WITH1-C8-alkyl, C3-C10-alkyl, which is interrupted in the chain by oxygen, WITH5-C8-cycloalkyl, tetrahydrofuryl etc., Z2- C1-C18-alkyl, C2-C4-alkyl, substituted IT WITH7-C9-phenylalkyl, Z3is hydrogen, C1-C18-alkyl, C2-C4-alkyl, substituted IT WITH7-C9-phenylalkyl, Z2and Z3taken together mean WITH3-C6OK who provide stabilization of the polymeric composition in an amount of 0.01-30% by weight of the polymer. Polymers, such as polyolefin, polybutadiene rubber, block copolymers of styrene and butadiene or Acrylonitrile, styrene and butadiene. Increases the effectiveness of the stabilizers in comparison with the known substances. 3 S. and 4 C.p. f-crystals, 4 PL.

The invention relates to new derivatives of ethers of bisphenol a, through which stabilizing organic materials against oxidative, thermal and sweetestrossie.

The use of certain derivatives of esters of phenols as stabilizers are described, for example, in JP-A-4-308581, DE-A-3718751, EP-A-479560 and US-A-4414408.

The subject of the present invention are the compounds of formula I

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where the radical R1means independently of each other C1-C25-alkyl, C2-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, C5-C12cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or-CH2-S-X1,

the radical R2means independently from each other hydrogen, C1-C25-alkyl, C2-C24alkenyl, >2-cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, -CH2-S-X1, -(CH2)pCOO-X2or -(CH2)qO-X3,

the radical R3means independently from each other hydrogen or C1-C4-alkyl,

R4means hydrogen or C1-C8-alkyl,

R5means hydrogen, C1-C10-alkyl, phenyl, -CH2-COO-X4or CN,

R6mean water line, C1-C4-alkyl, phenyl, -COO-X5, -CN, or-CON(X6)(X7)

R7means hydrogen or C1-C10-alkyl,

R8means hydrogen, C1-C4-alkyl or phenyl,

X1means C1-C25-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or -(CH2)rCOO - Y1,

X2X4and X5means independently of each other C1-C25-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl, Samedan is, 5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C7-phenylalkyl, C1-C25-alkanoyl, C3-C25-alkenyl, C3-C25-alkanoyl with the bridge oxygen, sulfur or C6-C9-cycloalkylcarbonyl, benzoyl, benzoyl, substituted C1-C4-alkyl, tenor or furoyl,

X6and X7mean independently from each other hydrogen, C1-C25-alkyl, C2-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, C5-C12-cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl, Y1means C1-C25-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl, Y2means hydrogen or C1-C8-alkyl,

p varies from 0.1 to 2,

q is an integer from 0 to 8,

r is 1 or 2,

n is an integer from 1 to 4

if n = 1, avlab> or-S-Z8in addition, A is A heterocyclic radical, unsubstituted or substituted C1-C4the alkyl, the free valency of which is a nitrogen atom,

Z1means hydrogen, C1-C25-alkyl, C3-C25-alkyl bridge oxygen, sulfur, C3-C24alkenyl, monocyclic saturated hydrocarbon radical with 5 to 20 carbon atoms, a bicyclic saturated hydrocarbon radical with 5 to 20 carbon atoms, a tricyclic saturated hydrocarbon radical with 10-20 carbon atoms, C5-C12-cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, C7-C9-phenylalkyl,7-C9-phenylalkyl with substitution in the phenyl ring C1-C4-alkyl, tetrahydrofurfuryl, tetrahydrofuryl, C1-C25-alkanoyl, C3-C25-alkenyl, C3-C25-alkanoyl with the bridge oxygen, sulfur or C6-C9-cycloalkylcarbonyl benzoyl, benzoyl, substituted C1-C4-alkyl, tenor, furoyl or a group of formula IIa or IIb

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Z2means hydrogen, C1-C25-alkyl, C2-C25-alkyl substituted by hydroxyl, C3-C24alkenyl, C5-C12-cycleau>4-alkyl, C7-C9-phenylalkyl, C1-C25-alkanoyl, C3-C25-alkenyl, C3-C25-alkanoyl with the bridge oxygen, sulfur , or C6-C9-cycloalkylcarbonyl, benzoyl, benzoyl, substituted C1-C4-alkyl, tenor, furoyl, -(CH2)p- -COO-X2or a radical of the formula IIb,

Z3means hydrogen, C1-C25-alkyl, C2-C25-alkyl substituted by hydroxyl, C3-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb,

or

Z2and Z3together form a C3-C6-alkylene, C3-C6-oxoalkyl or C3-C6-alkylen with the bridge oxygen, sulfur or

Z4means C1-C25-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl,

Z5and Z6mean independently from each other hydrogen, C1-C25-alkyl, C2-C24alkenyl, C5-C12-cycloalkyl>C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl

or

the radicals Z5and Z6together with the carbon atom to which they are attached, form a C5-C12-cycloalkylation ring unsubstituted or substituted C1-C4-alkyl,

Z7means C1-C25-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or -(CH2)rCOO - Y1,

Z8mean 2-benzoxazolyl unsubstituted or substituted C1-C4-alkyl or 2-benzothiazolyl unsubstituted or substituted C1-C4-alkyl,

T1and T2mean independently from each other hydrogen, C1-C25-alkyl, C2-C12alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, C5-C12-cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or-CH2-S-X1alkyl, C2-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, C5-C12-cycloalkenyl, C5-C12-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, -(CH2)pCOO-X2or -(CH2)qO-X3,

T5means hydrogen, C1-C8-alkyl, C2-C4-alkyl, substituted hydroxyl group, OH, -OH, -NO, -CH2CN, C1-C18-alkyloxy, C5-C12-cycloalkane, C3-C6alkenyl, C7-C9-phenylalkyl, C7-C9-phenylalkyl substituted in the phenyl ring C1-C4-alkyl, C1-C8-alkanoyl, C3-C8-alkanoyl or benzoyl,

T6means C1-C12-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl,

m = 1 and 2

w = 0 or 1,

if n = 2, a is a group of formula IIIa, IIIb, IIIc, IIId, IIIe or IIIf,

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G1and G3mean independently from each other hydrogen, C1-C25-Ala -C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, -(CH2)p-COO-X2or a radical of the formula IIb,

G2means C2-C12-alkylene, C4-C20-alkylen with the bridge oxygen, sulfur, or C4-C20-albaniles, C4-C20-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and 5-12 carbon atoms, a bicyclic saturated hydrocarbon radical with two free valences and 7-30 carbon atoms, phenylene, phenylene, substituted C1-C4-alkyl, naftilan, C2-C20-alcander, C4-C20-alcendor or carboxybenzoyl, G4and G6means independently from each other hydrogen, C1-C25-alkyl, C3-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb,

G5means C2-C12-alkylene, C4-C20-alkylen with the bridge oxygen, sulfur or C4-C20-akinyan, C4-C20-alkene is odorata with two free valences and 5-12 carbon atoms, bicyclic saturated hydrocarbon radical with two free valences and 7-30 carbon atoms, phenylene, phenylene, substituted C1-C4-alkyl, or naftilan,

G7means C2-C20-alkylene, C4-C20-alkylen with the bridge oxygen, sulfur, C4-C20-albaniles, C4-C20-akinyan,

(C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and 5-12 carbon atoms, a bicyclic saturated hydrocarbon radical with two free valences and 7-30 carbon atoms, phenylene, phenylene, substituted C1-C4-alkyl, naftilan, C2-C20-alcindor, C4-C20-alcendor, carboxybenzoyl or a group of formula IVa, IVb or IVc

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G8and G10mean independently from each other hydrogen, C1-C25-alkyl, C3-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb,

G9and G11means independently of each other C12-C12-alkylidene, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon residue with two free valences and 5-12 carbon atoms, a bicyclic saturated hydrocarbon residue with two free valences and 7-30 carbon atoms, phenylene, phenylene, substituted C1-C4-alkyl, naftilan,

G12means hydrogen, C1-C25-alkyl, C3-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb,

the radical D1means independently from each other hydrogen, C1-C8-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl,

D2means independently from each other hydrogen, C1-C8-alkyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl,

D3and D4mean the independence of the carbohydrate, with which is associated, form unsubstituted or substituted C1-C4-alkyl, C5-C12-cycloalkylation ring,

t = 1 or 2

v = 0 or 1,

if n = 3, a is a group of formula Va, Vb or Vc,

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E1means C3-C7-alcantar,

E2and E3mean C2-C8-alkylen,

if n = 4, a is a group of the formula VI

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E4means C4-C10-alcantera or C4-C10-alcantera with the bridge oxygen.

Alkyl with the number of carbon atoms of up to 25, preferably up to 18, especially up to 10 carbon atoms is, for example, stands, ethyl, propylene, isopropyl, n-bootrom, second-bootrom, isobutyl, tert-bootrom, 2-ethylbutyl, n-Pentium, tert-Pentium, isopentyl, 1-methylpentyl, 1,3-di-methylbutyl, n-hexyl, 1-methylhexan, n-heptyl, isoheptyl, 1,1,3,3-TETRAMETHYLBUTYL, 1-methylheptane, 3-methylheptane, n-actiom, 2-ethylhexyl, 1,1,3-trimethylhexanal, 1,1,3,3-tetramethylpentane, nannilam, decyl, intellon, 1-methylindenyl, dodecyl, 1,1,3,3,5,5-hexamethyldisilane, tridesilon, tetradecyl, pentadecyl, hexadecimal, heptadecyl, octadecyl, akosile or cocosila.

Preferably R1and the scrap, tert-bootrom, tert-Pentium.

Preferably R4is C1-C4-alkyl, especially stands.

Preferably Y2is C1-C4-alkyl, especially stands.

Preferably Z2and Z2are C1-C18-alkilani.

Preferably Z7is C1-C18-alkyl, especially C1-C10-alkyl.

Preferably T1, T2and T4are C1-C4-alkyl, especially stands, tert-bootrom.

Preferably T5is C1-C4-alkyl, especially stands.

Preferably T6is C1-C4-alkyl.

Examples of C3-C25the alkyl bridge oxygen, sulphur or a is CH3-O-CH2-CH2-, CH3-CH2-O-CH2-CH2-CH2-O-, (CH3)2CH-O-CH2-CH2-,

CH2-S-CH2-CH2-, CH3-NH-CH2CH2-, CH3-N(CH3)-CH2CH2-, CH2-O-CH2CH2- -O-CH2CH2-, CH3-(O-CH2CH2-)2O-CH2CH2-, CH3-(O-CH2CH2-)3O-CH2CH2or CH3-(O-CH2CH23-C10-alkyl.

Radicals (C1-C5-alkyl)-(OCH2CH2)1-10and (C1-C5-alkyl)-(OCH2CH2)1-2preferred.

C2-C25-alkyl, substituted by a group-IT, especially C2-C4-alkyl, substituted by a group-IT is, for example, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl.

Examples of group C1-C18-alkyloxy are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentox, isopentane, hexose, heptose, actoxy, decyloxy, dodecyloxy, tetradecenoic, octadecylamine. Preferably C6-C12-alkyloxy, especially epoxy, actoxy.

Alkenyl with the number of carbon atoms to 24, particularly to 18 carbon atoms, are, for example, vinyl, propenyl, Isopropenyl, 2-butenyl, 3-butenyl, Isobutanol, 3-methyl-but-2-enyl, n-Octo-2-enyl, n-dodeca-2-enyl, ISO-dodecenyl, n-octadec-2-enyl or n-octadec-4-enyl. Preferred alkeneamine radicals, the carbon atoms are in position 1 is saturated, especially preferred C3-C18alkenyl. C5-C12-cycloalkyl, substituted C1-C4the alkyl or nezamescennych, dimethylcyclohexyl, trimethylcyclohexyl or tert-butylcyclohexyl. Preferably C5-C8-cycloalkyl, substituted C1-C4-alkyl or unsubstituted, particularly preferably cyclohexyl.

Preferably the radical R1cyclohexyl.

Examples of C5-C12-cycloalkane are cyclopentane, cyclohexane, Cycloheptane, cyclooctane, cyclodecane, cyclododecane. Cyclopentane, cyclohexane preferred.

Monocyclic saturated hydrocarbon residue with the number of carbon atoms from 5 to 20 is unsubstituted or substituted C1-C4-alkyl, C5-C12-cycloalkyl or (C5-C12-cycloalkyl)-(C1-C4-alkyl), not substituted or substituted in cycloalkylation residue C1-C4-alkyl, in particular cyclohexylmethyl, methylcyclohexylamine or dimethylcyclohexylamine.

Examples of bicyclic saturated hydrocarbon radicals with a number of carbon atoms of 7 to 20 are

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Examples of tricyclic saturated hydrocarbon residues with the number of carbon atoms from 10 to 20 are

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Examples of unsubstituted or substituted C1-C4

Substituted C1-C4the alkyl phenyl is, for example, were, dimethylphenyl, trimetilfenil, ethylphenyl, diethylphenyl, isopropylphenyl, tert-butylphenyl, di-tert-butylphenyl or methyl-di-tert-butylphenol.

Examples of unsubstituted or substituted C1-C4-alkyl, C5-C12-cycloalkylation rings are

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C5-C8-cycloalkylation ring is preferable.

Examples of C7-C9-phenylalkyl, which in this case is replaced by

C1-C4the alkyl in the phenyl ring, are benzyl, phenethyl, 3-phenylpropyl, - -methylbenzyl, ,- -dimethylbenzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl and tert-butylbenzyl.

Examples of alkanoyl with the number of carbon atoms to 25 are methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, deletion, pentadecanol, hexadecanol, octadecanol, nonadecanoic or eicosanol. Preferably C1-C18-alkanoyl. Signs of C3-C25alkanoyl with bridge sour>alkyl), and-CH-CH2CH2-N(Y2)-(C1-C10-alkyl). Preferably C3-C25-alkanoyl with the bridge oxygen or

Examples of C3-C25alkanoyl are acryloyl, methacryloyl, crotonoyl, isocrotonic and oleoyl. Preferably C3-C18-alkanoyl.

C6-C9-cycloalkylcarbonyl means, for example, cyclopentanecarbonyl, cyclohexylcarbonyl, cyclohexylcarbonyl or cyclooctylmethyl.

Examples of substituted C1-C4the alkyl benzoyl is, for example, methylbenzoyl, tert-butylbenzoyl.

Examples of unsubstituted or substituted C1-C4-alkyl heterocyclic radical having the free valence on the nitrogen atom, are:

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Preferably a 5-7 membered heterocyclic radical, and 9-10-membered heterocyclic radical. As heteroatom preferably nitrogen. Preferred is unsubstituted or substituted C1-C4-alkyl 1-pyrrolyl, unsubstituted or substituted C1-C4-alkyl 1-pyrazolyl, unsubstituted or substituted C1-C4-alkyl 1-imidazolyl, unsubstituted or substituted C1-C4-alkyl 1-benzimidazole carbon atoms to 20, especially up to 12 or up to 6, are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene, decamethrin, undeletion or dodecamethyl.

G2, G5, G7, G9and G11preferably are C2-C8-alkylene. Examples of C4-C20-alkylene with the bridge oxygen, sulphur or a is-CH2CH2-O-CH2CH2-, -CH2CH2-S-CH2CH2-, -CH2CH2-NH-CH2CH2-, -CH2CH2CH2-NH-cG2CH2CH2-,

-CH2CH2CH2-NH-CH2CH2-, -CH2CH2CH2CH2-NH-CH2CH2CH2-, -(CH2)6-NH-(CH2)6-,

CH2CH2-N(CH3)-CH2CH2-, -CH2CH2CH2-N(CH3)-CH2CH2CH2-, -CH2CH2-(O-CH2CH2-)2O-CH2CH2-, -CH2CH2-(O-CH2CH2-)3O-CH2CH2-, -CH2CH2(O-CH2CH2-)4O-CH2CH2-, -CH2CH2CH2CH2-O-CH2CH2CH2CH2-O-CH2CH2CH2CH2-,

-CH2CH2-NH-CH2CH2
CH2CH2-NH-CH2CH2CH2CH2- NH-CH2CH2CH2-. The most preferred C4-C20-alkylen with an oxygen bridge or a bridge Preferred radicals-CH2CH2CH2CH2-O-CH2CH2CH2CH2-O-CH2CH2CH2CH2- and-CH2CH2-O-CH2CH2-.

The radical-N(Z2)(Z3) is mainly morpholine.

C3-C6-alkylen with bridge > N-T6that is, for example,

-CH2CH2-N(CH3)-CH2CH2, -CH2CH2CH2-N(CH3)-CH2CH2CH2-.

C3-C6-oxoalkyl is, for example, -CO-CH2CH2CH2CH2-.

C4-C20-albaniles means, for example, 2-butylen-1,4,3-penttinen-1.5, or 2-hextile-1,6.

C4-C20-akinyan is for example, 2-Butyrin (-CH2O C-CH2-), 2-pentikinen, 2-geksanalem, 3-geksanalem, 3-Eptingen, 2-decisoin, 4-decisoin or 8-octadecenyl.

(C1-C4-alkylen)-phenylene-(C1-C4-alkylen) means, for example, a group

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Examples of monocyclic saturated moiety uglev is B>-cycloalkyl as cyclopentene, cyclohexene, cycloheptene or cyclooctene.

Examples of bicyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 7 to 30 are

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Substituted C1-C4-alkyl-phenylene is, for example, methylphenylene or tert-butylaniline.

Examples of C2-C20-alcantera are ethanediol, propandiol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol.

C2-C10-alcander preferred.

Examples of C4-C20-alcantera are, for example, maleoyl, fumaroli, citraconic or methanol.

Examples of C3-C7alcantarilha are

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Examples of C4-C10alcantarilha or C4-C10alcantarilha with an oxygen bridge are

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The radicals R5, R6, R7and R8preferably are hydrogen.

The value of n is preferably 1 or 2.

Preferred compounds of formula I where the radical R1independently of each other C1-C18-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C1
-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or-CH2-S-X1,

the radical R2independently from each other hydrogen, C1-C18-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, -CH2-S-X1, -(CH2)pCOO-X2or -(CH2)qO-X3,

the radical R3independently of one another is hydrogen, C1-C8-alkyl,

the radical R4means hydrogen or C1-C8-alkyl,

the radical R5preferably hydrogen, C1-C10-alkyl or phenyl,

R6means hydrogen, C1-C4-alkyl or phenyl,

R7means hydrogen or C1-C10-alkyl,

R8means hydrogen, C1-C4-alkyl or phenyl,

X1means C1-C18-alkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkyl, phenyl HB>1,

X2means C1-C18-alkyl, unsubstituted or substituted C1-C4-alkyl, C5-C8-cycloalkyl, unsubstituted phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl,

X3means C1-C18-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, C1-C18-alkanoyl, C3-C18-alkenyl, C3-C18-alkanoyl with the bridge oxygen or C6-C9-cycloalkylcarbonyl, benzoyl, benzoyl, substituted C1-C4-alkyl, tenor, furoyl,

Y1means C1-C18-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl, Y2means hydrogen or C1-C8-alkyl,

p = 0, 1, or 2,

q is an integer from 0 to 8,

r = 1 or 2

n is an integer from 1 to 4

if n = 1, group A is-O-Z1, - N(Z2(Z3), -NH(OZ4), -O-N= C(Z2)(Z6), -S(O)mZ7, -NH-Z8or-S-Z8or there is AlertNet which is located at the nitrogen atom,

Z1means hydrogen, C1-C18-alkyl, C3-C18-alkyl bridge oxygen or C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyl, substituted C1-C4-alkyl, C7-C9-phenylalkyl, C7-C9-phenylalkyl substituted in the phenol ring C1-C4-alkyl, tetrahydrofurfuryl, tetrahydrofuryl, C1-C18-alkanoyl, C3-C18-alkenyl, C3-C18-alkanol with an oxygen bridge or a bridge C6-C9-cycloalkylcarbonyl, benzoyl, benzoyl, substituted C1-C4-alkyl, tenor, furoyl or a group of formula IIa or IIb,

Z2means hydrogen, C1-C18-alkyl, C2-C18-alkyl, substituted HE, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl,

C1-C18-alkanoyl, C3-C18-alkenyl, C3-C18-alkanol with an oxygen bridge or a bridge C6-C9-cycloalkylcarbonyl decal formula IIb,

Z3means hydrogen, C1-C18-alkyl, C2-C18-alkyl, substituted HE, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb or

Z3and Z2together form a C3-C6-alkylene, C3-C6-oxoalkyl or C3-C6-alkylen with an oxygen bridge or a bridge

Z4means C1-C18-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl, Z5and Z6mean independently from each other hydrogen, C1-C18-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl or radicals Z5and Z6together with the carbon atom to which they relate, UB>7means C1-C18-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9- phenylalkyl or -(CH5)rCOO-Y1,

Z8means unsubstituted or substituted C1-C4the alkyl 2-benzoxazolyl or unsubstituted or substituted C1-C4the alkyl 2-benzothiazolyl,

T1and T2mean independently from each other hydrogen, C1-C18-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or

-CH2-S-X1,

T3means hydrogen or C1-C4-alkyl,

T4means hydrogen, C1-C18-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyl, substituted C1-C4-alkyl, phenyl, phenyl, UB>2or (CH2)qO-X3, T5means hydrogen, C1-C4-alkyl, -HE, C6-C12-alkyloxy, C5-C8-cycloalkane, allyl, benzyl or acetyl,

T6means C1-C12-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl or C7-C9-phenylalkyl, m = 1 or 2

w is 0 or 1,

if n = 2, a is a group of the formula IIIa, IIIb, IIIc, IIId, IIIe or IIIf

G1and G3mean independently from each other hydrogen, C1-C18-alkyl, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, -(CH2)pCOO-Xpor a radical of the formula IIb,

G2means C2-C12-alkylene, C4-C12-alkylen with an oxygen bridge or a bridge C4-C12-albaniles, C4-C12-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 12, phenyl shall cendol or carboxybenzoyl,

G4and G6independently of one another denote hydrogen, C1-C18-alkyl, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb,

G5means C2-C12-alkylene, C4-C12-alkylen with an oxygen bridge or a bridge C4-C12-albaniles, C4-C12-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 12, phenylene, phenylene, substituted C1-C4-alkyl, or naftilan,

G7means C2-C12-alkylene, C4-C12-alkylen with an oxygen bridge or a bridge C4-C12-albaniles, C4-C12-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 12, phenylene, phenylene, substituted C1-C4-alkyl, naftilan, C2-C18-alcindor, C4-C18- Who/SUB>-alkyl, C3-C18alkenyl, C5-C18-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4- alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl, a group of the formula IIb,

G9and G11mean C2-C12-alkylene, C4-C12-alkylen with an oxygen bridge or a bridge C4-C12-albaniles, C4-C12-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen), monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 12, phenylene, phenylene, substituted C1-C4-alkyl, or naftilan,

G12means hydrogen, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of formula IIb, C1-C18-alkyl,

t = 1 or 2.

The compound of the formula I are also preferred, if the radical R1means independently of each other C1-C10-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkenyl, phenyl, C7-C1-C10-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkenyl, phenyl, C7-C9-phenylalkyl, -CH2-S-X1, -(CH2)pCOO-X2or -(CH2)qO-X3,

the radical R3means hydrogen,

R4is hydrogen or C1-C4-alkyl,

R5is hydrogen, C1-C4-alkyl or phenyl,

R6is hydrogen, C1-C4-alkyl or phenyl,

R7is hydrogen or C1-C4-alkyl,

R8is hydrogen, C1-C4-alkyl or phenyl,

X1means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or -(CH2)rCOO-Y1,

X2means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl or C7-C9-phenylalkyl,

X3means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl, C1-C10-alkanoyl, C3-C18-alkenyl, C3-C18-alkanol with an oxygen bridge or benzoyl,

Y1means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl or C7-C9-phenylalkyl,

p = 0, 1, or 2,

q is an integer from 0 to d, NH(OZ4), -O-N= C(Z5)(Z6), -S(O)mZ7, -NH-Z8or-S-Z8or, in addition, A is unsubstituted or substituted C1-C4-alkyl heterocyclic moiety, the free valence of which is located at the nitrogen atom, Z1means hydrogen, C1-C18-alkyl, C3-C18-alkyl with an oxygen bridge, C3-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkenyl, C7-C9-phenylalkyl, tetrahydrofurfuryl, C1-C10-alkanoyl, C3-C18-alkenyl, C3-C18-alkanol with an oxygen bridge, benzoyl or a group of formula IIa or IIb,

Z2means hydrogen, C1-C18-alkyl, C2-C10-alkyl, substituted HE, C3-C18alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl, C1-C10-alkanoyl, C3-C18-alkenyl, C3-C18-alkanol with an oxygen bridge, benzoyl, -(CH2)pCOO-X2or a radical of the formula IIb,

Z3means hydrogen, C1-C18-alkyl, C2-C10-alkyl, substituted HE, C3-C18alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or a group of formula IIb or a-C6-alkylen with an oxygen bridge,

Z4means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl or C7-C9-phenylalkyl,

Z2and Z6independently of one another denote hydrogen, C1-C10-alkyl, C2-C18alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkenyl, phenyl or C7-C9-phenylalkyl, or

the radicals Z5and Z6together with the carbon atom to which they are attached, form a C5-C8-cycloalkylation ring,

X7means C1-C10-alkyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or -(CH2)rCOO-Y1,

Z8means unsubstituted or substituted C1-C4the alkyl 2-benzoxazolyl or unsubstituted or substituted C1-C4the alkyl 2-benzotriazolyl,

T1and T2independently of one another denote hydrogen, C1-C18-alkyl, C2-C12alkenyl, C5-C8-cycloalkyl, C5-C8-cycloalkenyl, phenyl, C7-C9-phenylalkyl or-CH2-S-X1,

T3hydrogen or C1-C4-alkyl,

T4hydrogen, C1-C10-alkyl, C2-C18-Ala is UB>-S-X1, -(CH2)pCOO-X2or -(CH2)qO-X3,

T5means hydrogen, C1-C4-alkyl, -HE, C6-C12-alkyloxy, C5-C8-cycloalkane, allyl, benzyl or acetyl,

m = 1 or 2

w = 0 or 1,

if n = 2, a is a group of the formula IIIa, IIIb, IIIc, IIId, IIIe or IIIf,

G1and G3mean independently from each other hydrogen, C1-C10-alkyl, C3-C18alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl, -(CH2)pCOO-Xpor a radical of the formula IIb,

G2means C2-C10-alkylene, C4-C12-alkylen with an oxygen bridge, C4-C10-albaniles, C4-C10-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen),

monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 10, phenylene, C2-C10-alcindor, C4-C10-alcendor or carboxybenzoyl,

G4and G6independently from each other hydrogen, C3-C18-alkyl, C5-C8alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or a group of formula IIb,

G5about the flax, C4-C10-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen),

monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 10 or phenylene,

G7means C2-C10-alkylene, C4-C12-alkylen with an oxygen bridge, C4-C10-albaniles, C4-C10-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen),

monocyclic saturated hydrocarbon radical with two free valences and the number of carbon atoms from 5 to 10, phenylene, C2-C10-alcindor, C4-C10-alcendor or carboxybenzoyl,

G8and G10independently of one another are hydrogen, C1-C10-alkyl, C3-C18-alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or a group of formula IIb,

G9and G11mean C2-C10-alkylene, C4-C12-alkylen with an oxygen bridge, C4-C10-albaniles, C4-C10-akinyan, (C1-C4-alkylen)-phenylene-(C1-C4-alkylen),

monocyclic saturated hydrocarbon radical with two free UB>3-C18alkenyl, C5-C8-cycloalkyl, phenyl, C7-C9-phenylalkyl or a group of formula IIb, and

t = 1 or 2.

The compounds of formula I are preferred, if

n = 1,

A is a group of formula-N(Z2)(Z3)

Z2is hydrogen,

Z3means hydrogen, C1-C25-alkyl, C2-C25-alkyl, substituted hydroxyl group, C3-C24alkenyl, C5-C12-cycloalkyl, C5-C12-cycloalkyl, substituted C1-C4-alkyl, phenyl, phenyl substituted C1-C4-alkyl, C7-C9-phenylalkyl or a group of the formula IIb.

In addition, preferred is a compound of formula I, if n = 1, a is a group of the formula-O-Z1and

Z1means C1-C25-alkyl with an oxygen bridge or a group of formula IIa

w = 1.

According to the invention preferred are the compounds of formula I, if

the radicals R1are the same and denote C1-C5-alkyl or C5-C8-cycloalkyl,

the radicals R2are the same and denote C1-C5-alkyl,

the radical R3is hydrogen,

R4is the BR>
the radicals R1are the same and denote C1-C5-alkyl or C5-C8-cycloalkyl,

the radicals R2are the same and denote C1-C5-alkyl,

the radical R3means hydrogen,

R4hydrogen or C1-C4-alkyl,

R5, R6, R7and R8are hydrogen,

n =1 or 2, and

if n = 1, a is a group-O-Z1, -N(Z2)(Z3), -NH(OZ4), -O-N= C(Z5)(Z6), -S(O)mZ7, -NH-Z8or-S-Z8or, alternatively, A is unsubstituted or substituted C1-C4-alkyl heterocyclic moiety, the free valence of which is located at the nitrogen atom,

Z1means C1-C18-alkyl, C3-C10-alkyl with an oxygen bridge, C5-C8-cycloalkyl, tetrahydrofurfuryl or a group of formula IIa or IIb,

Z2means C1-C18-alkyl, C2-C4-alkyl, substituted by a group of HE, C7-C9-phenylalkyl, -(CH2)pCOO-X2or a radical of the formula IIb,

Z3means hydrogen, C1-C18-alkyl, C2-C4-alkyl, substituted by a group-IT, C7-C9-phenylalkyl, or a radical of the formula IIb, or

the first bridge,

Z4means C7-C9-phenylalkyl,

the radicals Z5and Z6together with the carbon atom to which they are attached, form a C5-C8-cycloalkylation ring,

Z7is C1-C10-alkyl,

Z8is unsubstituted or substituted C1-C4the alkyl 2-benzoxazolyl or unsubstituted or substituted C1-C4the alkyl 2-benzotriazolyl,

T1, T2, T3and T4independently of one another are hydrogen or C1-C4-alkyl,

T5is hydrogen or C1-C4-alkyl,

X2is C1-C10-alkyl,

m = 1 or 2

p = 1,

w = 0 or 1 and

if n = 1, a is a group of formula IIIa, IIIc or IIIf,

G1and G3independently of one another are hydrogen, C7-C9-phenylalkyl or a radical of the formula IIb,

G2means C2-C8-alkylen or monocyclic saturated hydrocarbon radical with two free valences and 10 carbon atoms,

G7means C4-C12-alkylene or C4-C12-alkylen with an oxygen bridge,

G12means C7-C9-phenylalkyl or group FOM:

Method A: the Interaction of the compounds of formula a

< / BR>
with a corresponding compound of formula b (accession Michael)

< / BR>
when the radicals R1until R6and the index n correspond to the values specified for formula I.

The reaction may proceed by mixing both components of the reaction in the presence of a solvent or without solvent. Possible solvents are conventional hydrocarbons (such as toluene, hexane and cyclohexane), halogenated hydrocarbons (such as dichloromethane, dichloroethane and chlorobenzene), ethers (such as diethyl ether, disutility ether, tetrahydrofuran and dimethoxyethane), alcohols (such as methanol or ethanol) and, in addition, acetonitrile, butyl acetate, dimethylformamide.

The interaction is preferably carried out at a temperature of 5oC to the boiling temperature of the reaction mixture.

When attaching alcohol (or mercaptan) to the compound of formula a preferably to the reaction mixture to add a catalytic amount (0.5 to 30 mol. %) of the Foundation. Suitable bases are hydroxides of alkali metals, alkoxides C1-C5alkali metals, amines (e.g. triethylamine, N, N-dimly ORGANOMETALLIC compound (for example, BuLi).

The compounds of formula I, where a is a group-S(O)mZ7you can get the interaction bactenologica formula with a mercaptan of the formula b (A= SZ7and subsequent oxidation of the resulting tiefer conventional methods (Comprehensive Organic Chemistry, vol. 3, p. 124-126, 174, Ed. D. Neville Jones, Pergamon Press, 1979).

Method B: the Esterification or transesterification derivatives of carboxylic acids of the formula c

< / BR>
with a bisphenol of the formula d

< / BR>
where the radicals from R1to R8, A, and the index n correspond to the values for formula I and X, for example, is HE, Cl,

< / BR>
The reaction can be performed in a known manner, for example by adding one of the two components to a second component, and mixing the two components, preferably in the absence of oxygen. The interaction can be carried out in the presence of a solvent or without a solvent, the solvent can be used, for example toluene. The reaction temperature can be between the melting point and boiling point of the reaction mixture, for example between -50 and 150oC, preferably between 0 and 150oC. Purification of the products obtained can be carried out by known methods, for example by flushing water/HCl, extraction ori, and for phase chromatographic purification preferred hexane, ethyl acetate, or mixtures thereof.

If in the reaction as a carboxylic acid derivative is used, the acid chloride (X= Cl), to the reaction mixture, you can add the acid acceptor. Suitable acceptors are, for example amines as pyridine or triethylamine. Preferably the number of acceptor equivalent to the amount of the acid chloride. It is, for example, 1 equivalent, preferably from 1.2 to 1.7 equivalents of the acid chloride.

The acid chloride can also be obtained in situ. In this case, the carboxylic acid of formula (X=OH), the bisphenol of formula d and the acid acceptor (such as triethylamine) are mixed and immediately added phosphorus oxychloride by analogy with the method described, for example, in US-A-5.128.398.

If you use a carboxylic acid of the formula and the bisphenol of formula d as the original products, it is advisable to carry out communication using reagent freely substitute water as, for example, dicyclohexylcarbodiimide.

Method C: the Interaction of chloride of formula e

< / BR>
with a compound of formula b, preferably in the presence of a base as acid acceptor. Suitable lia), the alcoholate (for example, methanolate sodium and tert-butyl potassium) and organic base, such as BuLi).

If the grounds are hydrides, alkali metals, hydroxides of alkali metals, alkali metal alcoholate or organolithium compounds, then you need to get the corresponding anion of the compounds of formula b.

Examples of compounds of formula I are given in the following table 1

The compounds of formula I are used for stabilizing organic materials against thermal, oxidative and cotoniero destruction. Examples of such materials are:

1. Polymers of mono - and diolefins, for example polypropylene, polyisobutylene, polybutene-1, poly-4-methylpentene-1, polyisoprene or polybutadiene, as well as polymerizate of cycloolefins, such as cyclopentene or norbornene, polyethylene (which may be crosslinked), e.g. high density polyethylene (NDRE), high-density polyethylene and high molecular weight (NDRE-HMW), high density polyethylene and ultrahigh molecular weight polyethylene, medium density (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), branched polyethylene dizkodude paragraph as an example, especially polyethylene and polypropylene can be obtained in various ways, preferably by the following methods:

a) radical (usually at high pressure and high temperature).

b) by catalyst, the catalyst usually contains one or more metals of groups IVb, Vb, VIb or VIII. These metals are usually associated with one or more ligands as oxides, halides, alcoholate, ethers, esters, amines, alkali, alkenyl and/or arily, which can have either-or - coordination. These metal complexes can be free or fixed media, such as on activated magnesium chloride, titanium chloride (III), aluminium oxide or silicon oxide. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts can be active only during polymerization, or may be used for subsequent activation, as, for example, alkali metals, metal hydrides, alkylhalogenide metals, alkyloxy or alkyloxy metals, and the metals are the elements of the Ia, IIa and/or IIIa groups. Activators can interact subsequently with ether, ester, amino or silylamine groups. These rolled the catalysts (SSC).

2. The mixture mentioned in paragraph 1 of the polymers, for example mixtures of polypropylene and polyisobutylene, polypropylene and polyethylene (for example PP/NDRE, PP/LDHE) and a mixture of polyethylene of different types (for example LDPE/HDPE)

3. Copolymers of mono - and diolefins with each other or with other vinyl monomers, for example ethylene-propylenebis copolymer, linear low density polyethylene (LLDPE) and mixtures with low density polyethylene (LDPE), a copolymer of propylene and butene-1 copolymer of propylene and isobutylene, a copolymer of ethylene and butene-1 copolymer of ethylene and hexene, a copolymer of ethylene and methylpentene, the copolymer) of ethylene and Heptene copolymer of ethylene and octene, a copolymer of propylene and butadiene, a copolymer of isobutylene and isoprene, a copolymer of ethylene and alkylacrylate, a copolymer of ethylene and alkylmethacrylamide, a copolymer of ethylene and vinyl acetate and their copolymers with carbon monoxide, or copolymers of ethylene and acrylic acid and their salts (monomers), and terpolymer of ethylene with propylene and a diene such as hexadiene, Dicyclopentadiene, ethylidenenorbornene, except that a mixture of these copolymers with each other or with polymers mentioned in paragraph 1, for example polypropylene/ ethylene copolymer and propylene, LDPE/ ethylene copolymer and vinyl acetate, LDP is howling acid and copolymers of polyalkylene/ carbon monoxide different patterns, including statistical, and their mixtures with other polymers, such as polyamides.

4. Hydrocarbon resins (for example, C5-C9) including hydrogenated modifications (e.g., power stickiness), and a mixture of polyalkylene and starch.

5. Polystyrene, poly(p-methylsterol), poly - methylsterol).

6. Copolymers of styrene or a - methylstyrene with denami or acrylic derivatives, such as styrene-butadiene, styrene-Acrylonitrile, styrene-alkylmethacrylamide, styrene-butadiene-alkylacrylate and-methacrylate, styrene-maleic anhydride, styrene-Acrylonitrile-methyl acrylate, mixtures of high impact strength from copolymers of styrene and other polymers, such as polyacrylate, a diene polymer or an ethylene propylene-diene terpolymer, as well as copolymers of styrene, such as styrene-butadiene-styrene, styrene-isoprene-styrene, styrene-ethylene/butylene-styrene or styrene-ethylene/propylene-styrene.

7. Graft copolymers of styrene or a - methylstyrene, as, for example, styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-Acrylonitrile copolymers, styrene and Acrylonitrile (including Methacrylonitrile) on polybutadiene; styrene, Acrylonitrile and methyl methacrylate n maleic acid imide on polybutadiene; the styrene maleic acid imide on polybutadiene, styrene and alkylacrylate, including alkylmethacrylamide on polybutadiene; styrene and Acrylonitrile on ethylene-propylene-diene thermopolymer; styrene and Acrylonitrile on polyalkylacrylate or polyalkylacrylate; styrene and Acrylonitrile on acrylate copolymer and butadiene, and mixtures thereof with the copolymers listed in paragraph 6, such as so-called ABS, MBS-, ASA or AES polymers.

8. Halogenated polymers, such as polychloroprene, glorious, chlorinated and brominated copolymers of isobutylene and isoprene (halobutilic), chlorinated or chlorosulphurized polyethylene, copolymers of ethylene and chlorinated ethylene Homo - and copolymers of epichlorhydrine, the preferred polymers of halogen-containing vinyl compounds, such as polyvinyl chloride, grades, polyvinylidene fluoride; and also their copolymers, as the vinyl chloride-vinylidenechloride, vinyl chloride-vinyl acetate or vinylidenechloride-vinyl acetate.

9. Polymers derived from unsaturated acids and their derivatives, as polyacrylates and polymethylacrylates, adamvasco modified with butyl acrylate poly (methyl methacrylate), polyacrylamide and polyacrylonitrile.

< copolymers of Acrylonitrile and butadiene, copolymers of Acrylonitrile and alkylacrylate, copolymers of Acrylonitrile and alkoxylalkyl, copolymers of Acrylonitrile and vinylchloride or terpolymer Acrylonitrile, alkylmethacrylamide and butadiene.

11. Polymers derived from unsaturated alcohols and amines, such as their acyl derivatives or acetals as polyvinyl alcohol, polyvinyl acetate, stearate, benzoate, maleate, polyvinyl butyral, polyarylate, polyallylamine; and also their copolymers with olefins mentioned in paragraph 1.

12. Homo - and copolymers of cyclic ethers, as polyalkyleneglycol polyethyleneoxide, polypropyleneoxide or their copolymers with bisglycinate ether.

13. Polyacetals, as Polyoxymethylene, and also the polyoxymethylenes containing comonomers, such as ethylene oxide; Polyacetals modified with thermoplastic polyurethane, acrylates or MBS.

14. Polyphenyleneoxides and sulfides and their mixtures with polymers of styrene or a polyamide.

15. Polyurethanes derived from polyethers, esters and polybutadiene with fixed hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other hand, as well as their intermediates.

testwuide lactam, as the polyamide-4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides derived from m-xylene, diamine and adipic acid; a polyamide derived from a diamine and ISO - and/or terephthalic acid and the elastomer as modifier, for example poly-2,4,4-trimethylhexamethylenediamine or polyamide m-phenylene-isophthalic acid. The copolymers of the aforementioned polyamides with polyolefins, copolymers with olefins, ionomers or chemically bonded or grafted elastomers; or with polyethylene, as, for example, polyethylene glycol, polypropyleneglycol or polytetramethylene. In addition, with EPDM or ABC modified polyamides or copolyamids; and such polyamides condensed during processing ("PIM-polyamide systems").

17. Polyurea, polyimide, polyamide-imides, imides simple and polyesters, poligeenan and polybenzimidazole.

18. Polyesters derived from dicarboxylic acids and datanya alcohols and/or hydroxycarbonate acid or the corresponding lactone as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylcyclohexane, polyhydroxybenzenes, as well as block copolymers complex and prolific, modified MBS.

19. Polycarbonates and polycarbonate esters.

20. Polysulfones, polyether polysulfones, polyether ketones.

21. Crosslinked polymers derived from aldehydes on the one hand and phenols, urea or melamine on the other hand, as phenol-formaldehyde, urea-formaldehyde and melamine-formaldehyde resins.

22. Drying, non-drying alkyd resins.

23. Unsaturated resins polyesters derived from copolymers of polyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinking agent, and their halogenated with low inflammability modification.

24. Crosslinked acrylic resins derived from substituted acrylic esters of the acids, as, for example, epoxyacrylate, urethane-acrylates or polymers of esters of acrylates.

25. Alkyd resins, resins, polyesters and acrylic resins, crosslinked melamine resin, urea resin, isocyanate, isocyanurate, polyisocyanate or epoxy resin.

26. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic initiauy ether, sewn by conventional curing agents, such as anhydrides or amines, with or without the accelerator.

27. Natural polymers such as cellulose, natural rubber, and their chemically modified derivatives as acetate, propionate or butyrate cellulose, such as cellulose ether, as methylcellulose, as well as rosins and derivatives.

28. A mixture of (grafted polymers) of these polymers, such as PP/EPDM, polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, RUM/ thermoplastic PUS, PC/thermoplastic PUR, POM/acrylate, RUM/ MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or PBT/PEN/PC.

29. Natural and synthetic organic substances which are pure monomers or a mixture such as, for example, mineral oil, vegetable or animal fats, waxes and fats based on synthetic esters (for example, phthalate, adipate, phosphate or trimellitate), and also mixtures of synthetic esters with mineral oils in any weight ratio, as, for example, they are used for applying auxiliary substances on synthetic canvas in the process of its formation, as well as their water emulsion.

30. Aqueous emulsions of natural or synthetic rubber, as x2">

Another object of the invention is a composition comprising susceptible to oxidative, thermal and cotoniero decomposition of organic material and a minimal amount of compounds of formula I.

Under organic material mainly refers to synthetic polymers, especially those which contain the above-mentioned groups. Polyolefins and polybutadiene rubber obtained by polymerization in solution, the most preferred. Particularly preferred styrene-butadiene copolymer obtained by polymerization in solution, or a styrene-butadiene block copolymers, the ratio of styrene and a conjugated butadiene for example is 5: 95 to 95:5. Preferably the proportion of polybutadiene in such copolymers is from 5 to 30%. Preferable as the organic material used is a copolymer of Acrylonitrile, butadiene and styrene.

The compounds of formula I added to the stabilized organic material in an amount of from 0.01 to 10%, preferably from 0.01 to 5%, most preferably from 0.05 to 0.5% based on the weight of the stabilized material.

The application proposed in the invention compounds on organic materialise dissolved or dispersed compounds to the organic material, with subsequent evaporation of the solvent. Proposed according to the invention compounds can be added to the stabilized material in the form of powder, granules or in the form of a concentrate (master BAC) containing 2.5 to 25 wt.%.

The compounds of formula I may be added before or during polymerization or before crosslinking.

Stabilized in this way materials can be used in various forms such as films, fibers, molded pulp, profiles or as a binder for lacquers, adhesives or putties.

Stabilized organic materials may optionally contain various excipients, such as, for example:

1. Antioxidants

1.1 Alkylated monophenol, including 2,6-di-tert-butyl-4-METHYLPHENOL, 2-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenyl, 2,6-di-cyclopentyl-4-METHYLPHENOL, 2 - methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-METHYLPHENOL, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethanol, line, or with the side chains branched Nonylphenol as 2,6-di nonyl-4-METHYLPHENOL, 2,4-dimethyl-6-(1'-methyl-undeca-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyl-heptadec-1'-yl)-phenol,methyl-6-tert-butylphenol, 2,4-di-actitioner-6-METHYLPHENOL, 2,4-di-actitioner-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-Nonylphenol.

1.3. Hydroquinone and alkilirovanny hydroquinone, for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyl-oxyfuel, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl-stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate.

1.4 Tocopherol, for example - tocopherol - tocopherol - tocopherol - tocopherol and a mixture (vitamin E)

1.5 Gidroksilirovanii esters of thiodiphenol, for example 2,2'-thio-bis(6-tert-butyl-4-METHYLPHENOL), 2,2'-thio-bis(4-op), 4,4'-thio-bis(6-tert-butyl-3-METHYLPHENOL), 4,4'-thio-bis(6-tert-butyl-2-METHYLPHENOL), 4,4'-thio-bis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-di-methyl-4-hydroxyphenol)-disulfide.

1.6 Alkylidene bisphenol such as 2,2'-methylene-bis(6-tert-butyl-4-METHYLPHENOL), 2,2'-methylene-bis(6-tert-butyl-4-ethylphenol), 2,2'-methylene-bis/-4-methyl-6 - methylcyclohexyl)-phenol/, 2,2'-methylene-bis-(4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis-(6-nonyl-4-methyl-phenol), 2,2'-methylene-bis(4,6-di-tert-butylphenol), 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 2,2'-ethylidene-bis(6-tert-butyl-4-isobutylphenyl), 2,2 re-butylphenol), 4,4'-methylene-bis(6-tert-butyl-2-METHYLPHENOL), 1,1-bis(5-tert-butyl-4-hydroxy-2-were-butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-METHYLPHENOL, 1,1,3-Tris(5-tert-butyl-4-hydroxy-2-were-butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptan, ethylene glycol bis/3,3-bis(3'-tert-butyl-4 hydroxyphenyl)-butyrate/, bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)-Dicyclopentadiene, bis/2(3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert-butyl-4 - methyl-phenyl/-terephthalate, 1,1-bis(3,5-dimethyl-2-hydroxyphenyl)-butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-propane, 2,2-bis(5-tert-butyl-4-hydroxy-2-were) -4-N-dodecylmercaptan-butane, 1,1,5,5-Tetra(5-tert-butyl-4-hydroxy-2-were-pentane.

1.7 Connection 0-, N - and S-benzyl, for example 3,5,3',5-'-Tetra-tert-butyl-4,4'-dihydroxydiphenyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl-mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butyl-benzyl mercaptoacetate, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-dithiotreitol, bis(3,5-di-tert-butyl-4-hydroxybenzyl)-sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl-mercaptoacetate.

1.8 Hydroxybenzoate malonate, such as dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxy-Ben is et-butyl-4-hydroxybenzyl)-malonate, di-/4-(1,1,3,3-TETRAMETHYLBUTYL)-phenyl/-2,2-bis(3,5-di-tert-butyl-4 - hydroxybenzyl)-malonate.

1.9 Hydroxybenzene aromatic compounds, for example 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-phenol.

1.10 Triazine compounds, for example 2,4-bis-artillerie-6- (3,5-di-tert-butyl-4-hydroxy-aniline)-1,3,5-triazine, 2-artillerie-4,6-bis(3,5-di-tert-butyl-4-hydroxyanisole)-1,3,5-triazine, 2-artillerie-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5 - triazine, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxyphenylpropionic)-hexahydro - 1,3,5-triazine, 1,3,5-Tris(3,5-dicyclo-hexyl-4-hydroxybenzyl)-isocyanurate.

1.11 Benzylphosphonates, for example dimethyl-2,5-di-tert-butyl-4-hydroxyethylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxyethylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxyethylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, Ca-Sol monae 4-hydroxy-lauric acid anilide, anilide 4-hydroxystearate acid, oktilovom ester of N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamino acid.

1.13 Esters - (3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid with one or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propandiol, neopentylglycol, thiodiethanol, diethylene glycol, triethylene glycol, pentaerythritol, Tris(hydroxyethyl)-isocyanurate, N,N'-bis(hydroxyethyl) -oxalic acid diamide, 3-thia-undecanol, 3-thiapentanal, trimethylhexanal, trimethylolpropane, 4-hydroxymethyl-1-FOSFA-2,6,7-dioxabicyclo/2.2./-octane.

1.14 Esters - (5-tert-butyl-4-hydroxy-3-were)-propionic acid with one or polyhydric alcohols, such as, for example, with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol ethylene glycol, 1.2-propane diol, neopentylglycol, thiodiethanol, diethylene glycol, triethylene glycol, pentaerythritol, Tris(hydroxyethyl)-isocyanurate, diamid N,N'-bis (hydroxyethyl)-oxalic acid, 3-Ticonderoga, 3-thiapentanal, trimethylhexanal, tomatillas, 4-hydroxymethyl-1-FOSFA-2,6,7-dioxabicyclo-/2.2.2/-octane.

Mer, methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propandiol, neopentylglycol, thiodiethanol, diethylene glycol, pentaerythritol, Tris(hydroxyethyl)-isocyanurate, N,N'-bis(hydroxyethyl)-oxalic acid diamide, 3-Ticonderoga, 3-thiapentanal, trimethylhexanal, trimethylolpropane, 4-hydroxymethyl-1-phosphate - 2,6,7-dioxabicyclo/2.2.2/-octane.

1.16 Esters of 3,5-di-tert-butyl-4-hydroxyphenylarsonic acid with one or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propandiol, neopentylglycol, thiodiethanol, triethylene glycol, pentaerythritol, Tris(hydroxyethyl)-isocyanurate, N,N'-bis(hydroxyethyl) oxalic acid diamide, 3-Ticonderoga, 3-thiapentanal, trimethylhexanal, trimethylolpropane, 4-hydroxymethyl-1-FOSFA-2,6,7-dioxabicyclo-/2.2.2/-octane.

1.17 Amides - (3,5-di-tert-stil-4-hydroxyphenyl) -propionic acid, such as N, N'-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionic)-hexamethylenediamine were, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionic)-trimethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionic)-hydrazine.

1.18 Ascorbic acid (Vitamin C).

2 UV. Absorbers and light stabilizers

2.1 2-(2'-hydroxyphenyl)-benzotriazole, as, for example, 2-(2'-hydroxy-5'-were-benzotriazol, 2-(3', 5'-di-tert-butyl-2'-hydroxyphenyl)-benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)-benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-TETRAMETHYLBUTYL)phenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-were)-5-chloro-benzotriazole, 2-(3'-sec.-butyl-5'-tert-butyl-2'-hydroxy-phenyl)-benzotriazole, 2-(2'-hydroxy-4'-acetoxyphenyl)-benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)-benzotriazole, 2-(3', 5'-bis - dimethylbenzyl)-2'-hydroxyphenyl)-benzotriazol, a mixture of 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxyphenyl)- phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-5'-(2-octyloxyphenyl) phenyl)-benzotriazole, 2-(3'-tert-butyl-5'-/2-(2-ethylhexyloxy)carbonylethyl/-2'-hydroxyphenyl)- benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5-were-benzotriazole and 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctylmercaptoacetate)phenyl - benzotriazole, 2,2'-methylene-bis/4-( 1,1,3,3-TETRAMETHYLBUTYL)-6-benzotriazol-2-yl-phenol/, the product of the interesterification 2-/3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2-hydroxy-phenyl/ -benzotriazole with polyethylene glycol 300; CR-CH2CH2-COO(CH2)3] 2with R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-yl-phenyl.

2.2. 2-hydroxybenzophenone, as, for example, 4-hydroxy, 4-methoxy-, 4-actoxy-, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy-, 4,2',4'-trihydroxy-, 2'-hydroxy-4,4',-dimethoxy - derivative.

2.3 Esters of substituted benzoic acids, such as 4-tert-butyl-phenyl-salicylate, fenilsalitsilat, dibenzoylresorcinol, bis-(4-tert-butyl-benzoyl)-resorcinol, benzoylation, 3,5-di-tert-butyl-4-hydroxybenzoic acid 2,4-di-tert-BUTYLPEROXY ether, hexadecylamine ester of 3,5-tert-butyl-4-hydroxybenzoic acid, octadecenoic ester of 3,5-di-tert-butyl-4-hydroxybenzoic acid, 2-methyl-4,6-di-tert-BUTYLPEROXY ester of 3,5-di-tert-butyl-4-hydroxybenzoic acid.

2.4. Acrylates, such as for example ethyl ether - cyan -,- de - cyan -- methyl-p-methoxy-cinnamic acid, its butyl ether, methyl ether, carbomethoxy-p-methoxy-cinnamic acid, N - (carbomethoxy -- cyanovinyl)-2-methyl-indolin.

2.5 Connection of Nickel, for example, complexes of Nickel 2,2'-thio-bis/4-(1,1,3,3-Tetra-methylbutyl)-phenol/, as a complex of 1: 1 or 1:2, in this case with additional ligands, such as n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine, nickeldimethylglyoxime, Nickel salt monoalkyl ester 4-hydroxy-3,5-di-tert-butylbenzylphthalate acid, for example, methyl or ethyl ester, the Nickel complex with cetuximab, as 2-hydroxy-4-methyl-phenyl-undecyloxy, Nickel complex of 1-phenyl-4-lauroyl-5-hydroxy-pyrazole, in this case with additional ligands.

2.6 Steric employed amines, such as bis(2,2,6,6-tetramethyl-piperidine-4-yl)-sebacina, bis-(2,2,6,6-tetramethyl-piperidine-4-yl) succinate, bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-sebacina, bis(1-octyloxy-2,2,6,6-tetramethylpiperidine-4-yl)-sebacina, n-butyl-3,5, -di-tert-butyl-4-hydroxybenzyl-malonic acid bis(1,2,2,6,6-pentamethylpiperidine ether), the condensation product of 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, condensation product of N,2,6,6-tetramethyl-4-piperidyl)-nitrilotriacetate, tetrakis(2,2,6,6- -tetramethyl-4-piperidyl)-1,2,3,4-butanetriol, 1,1'-(1,2-ethandiyl)-bis(3,3,5,5-tetramethyl-piperazinone, 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-sterilox-2,2,6,6-tetramethylpiperidine, bis(1,2,2,6,6-pentamethylpiperidin)-2-n-butyl-2-(2-hydroxy-3,5 - di-tert-butylbenzyl)-malonate, 3-n-octyl-7,7,9,9-Tetra-methyl-1,3,8-tratosphere/4.5/decane-2, 4-dione, bis(1-octyloxy-2,2,6,6-tetramethylpiperidine)-sebacina, bis(1-octyloxy-2,2,6,6-tetramethylpiperidine)-succinate, condensation product of N, N-bis(2,2,6,6-tetramethyl-4-piperidyl)-diamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the condensation products of 2-chloro-4,6-di(4-n-butylamino-2,2,6,6-tetramethylpiperidine)-1,3,5-triazine and 1,2-bis(3-aminopropylene)-ethane, condensation product of 2-chloro-4,6-di(4-n-butylamino-1,2,2,6,6-pentamethylpiperidin)-1,3,5 - triazine and 1,2-bis(3-aminopropylene)ethane, 8-acetyl-3-dodecyl-7,7,9,-tetramethyl-1,3,8-diazaspiro/4.5/decane-2,4 - dione-, 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)-pyrrolidin-2,5-dione, mixture of 4-hexadecylamine - and 4-sterilox-2,2,6,6-tetramethylpiperidine, the condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-gexametilenimina and 4 cyclohexylamino-2,6-dichloro-1,3,5-triazine, condensation product of 1,2-bis(3-aminopropylene)-ethane and 2,4,6-Tr is l)-n-dodecylamine, N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylamine, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-Spiro/4,5/ Dean, the product of the transformation 7,7,9,9-tetramethyl-2-cyclodecyl-1-oxa - 3,8-diaza-4-oxaspiro/4.5/decane and epichlorohydrin.

2.7 the Diamide of oxalic acid, as, for example, 4,4'-di-octyloxy-oxamyl-ID, 2,2'-diethoxy-oxanilide, 2,2'-di-octyloxy-5,5'-di-tert-butyl-oxanilide, 2,2'-di-dodecyloxy-5,5'-di-tert-butyl-oxanilide, 2-ethoxy-2'- ethyl-oxanilide, N, N'-bis(3-dimethylaminopropyl)-oxalate, 2 ethoxy-5-tert-butyl-2'-ethyloxazole and their mixtures with 2-ethoxy-2-ethyl-5,4'-di-tert-butyl-oxanilide mixture of o-, p-methoxy-and of o - and p-ethoxy di-substituted oxanilide.

2.8. 2-(2-hydroxyphenyl)-1,3,5-triazine as, for example, 2,4,6-Tris-(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-proproxyphene)-6-(2,4-dimetilfenil)-1,3,5-triazine, 2-(2-hydroxy-4-octyl oksifenil)-4,6-bis(4-(were)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazine, 2-(2-hydroxy-4-tridecylalcohol)-4,6-bis-(2,4-dimetilfenil)- 1,3,5-triazine, 2-/2-hydroxy-4-(2-hydroxy-3-Butylochka-propyloxy)- phenyl/-4,6-bis (2,4-dimethyle is decyloxy/tridecylamine-2-hydroxypropoxy)- 2-hydroxy-phenyl/-4,6-bis(2,4-dimetilfenil)-1,3,5-triazine, 2-/2-hydroxy-4-(2-hydroxy-3-dodecyloxy-propoxy)phenyl/-4,6-bis (2,4-di-methyl)-1,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-Tris/2-hydroxy-4-(3-butoxy-2-hydroxy-propoxy)phenyl/-1,3,5 - triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine.

3. The decontamination officers of metals, such as, for example, diamid N,N diphenylsilane acid, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)-hydrazine, N, N-bis(3,5-di-tert-butyl-4 - hydroxyphenylpropionic)-hydrazine, 3-salicylamide-1,2,4-triazole, Digidesign bis(benzylidene)-oxalic acid, oxanilide, dehydrated isophthalic acid, bis-phenylhydrazide sabatinovka acid, dehydrated N,N'-di-acetyl-adipic acid, dehydrated N,N'-bis-salicyloyl-oxalic acid, dehydrated N,N'-bis-salicyloyl-thiopropionic acid.

4. The phosphonites and phosphites, such as, for example, triphenylphosphite, diphenylacetic, phenylvaleric, three (nonylphenyl)-pofit, trilaurylamine, trioctadecyl, DISTEARYL-pentaerithritol, Tris(2,4-di-tert - butylphenyl)-pofit, diisodecylphthalate-diphosphite, bis(2,4-di-tert.butylphenyl)-pentaerythrityl, bis-(2,6-di-tert-butyl-4-were)-pentaerithritol the tert-butylphenyl)-pentaerythrityl, Tristearin-sorbitol-three-pofit, tetrakis(2,4-di-tert-butylphenyl)-4,4-biphenylene-diphosphonic, 6-isooctane-2,4,8,10-Tetra-tert-butyl-N-dibenz /d,g/-1,3,2-di - oxaphosphorin, 6-fluoro-2,4,8,10-Tetra-tert-butyl-12-methyl-dibenz-/d g/-1,3,2-dioxaphospholane, bis(2,4-di-tert-butyl-6-were)-methylphosphonic, bis(2,4-di-tert-butyl-6-were-ethylphosphate.

5. Hydroxylamine, as, for example, N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctylsebacate, N,N-drawingdocument, N,N-detraditionalisation, N, N-dihexadecyl, N,N-dictatorially, N, N-hexadecyl-N-octadecyl-hydroxylamine, N,N-heptadecyl-N-octadecyltriethoxysilane, N, N-dialkylhydroxylamines of hydrogenated fatty amines.

6. Nitron, as, for example, N-benzyl-alpha-phenyl-Nitron, N-ethyl-alpha-methyl-Nitron, N-octyl-alpha-heptyl-Nitron, N-lauryl-alpha undecyl-Nitron, N-tetradecyl-alpha tridecyl-Nitron, N-hexadecyl-alpha pentadecyl-Nitron, N-octadecyl-alpha heptadecyl-Nitron, N-hexadecyl-alpha heptadecyl-Nitron, N-octadecyl-alpha pentadecyl-Nitron, N-heptadecyl-alpha heptadecyl-Nitron, N-octadecyl-alpha hexadecyl-Nitron, Nitron derivatives of N,N-dialkylhydroxylamines derived from hydrogenated fatty amines.

7. T the howling acid.

8. Paracycnotrachelus connection, as, for example, ether - thio-di-propionic acid, such as lauric, ministerului, stearic and tridecylamine esters, mercaptobenzimidazole, zinc salt of 2-mercaptobenzimidazole, zinc-dibutil-dithiocarbamate, dioctadecyl-disulfide, pentaerythritol-tetrakis - dodecylmercaptan)-propionate.

9. Polyamide stabilizers, such as, for example, salt of copper in combination with iodide and/or a compound of phosphorus and salts of divalent manganese.

10. Basic Co-stabilizers, such as, for example, melamine, polivinilpirolidon, dicyandiamide, treelistener, urea derivatives, hydrazine derivatives, amines, polyamide, polyurethane, salts of alkali and alkaline earth metals and of higher fatty acids, for example calcium stearate, zinc stearate, beginat magnesium, stearate, ricinoleic sodium, potassium palmitate, pyrocatechin antimony or pyrocatechin zinc.

11. Nucleobases means, as, for example, inorganic substances such as talc, metallic oxides, as titanpoker or magnesium oxide, phosphates, carbonates or sulfates, preferably of alkaline earth metals; organic compounds as mono - or polycarboxylic acids and their salts such as, for example, 4-I; high-molecular compounds such as, for example, ionic copolymers ("ionomers").

12. Fillers and reinforcing means, as, for example, calcium carbonate, silicates, glass, spherical glass, asbestos, talc, kaolin, mica, barium sulphate, oxide and hydroxide of metals, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.

13. Other additives, such as plasticizer, softening agent, emulsifier, pigments, additives regulatory rheological properties, catalysts, auxiliaries for spills, bleach, flame retardants, antistatics, blowing agents, CN.

14. Benzofuranol, for example, indoline, as, for example, described in US-A -4325863, US-A-4338244, US-A-5175312, US-A-5216052, US-A-5252643, DE-A-4316611, DE-A-4316622, DE-A-4316876, EP-A-0591102, or EP-A-0589839 3-/4-(acetoacetate)phenyl/-5,7-di-tert-butyl-benzofuran-2-it, 5,7-di-tert-butyl-3-/4-(2-stearoyl-acetoxy)phenyl/- benzofuran-2-it, 3,3'-bis/5,7-di-tert-butyl-3-(4-/2-hydroxyethoxy/- phenyl)-benzofuran-2-it, 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2 he, 3-(4-acetoxy-3, 5dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2 he, 3-(3,5-dimethyl-4-pivaloyloxymethyl)-5,7-di-tert-butyl-benzofuran-2-it.

The mass ratio proposed in izobreteniya compounds of formula I for stabilising organic materials against oxidative, thermal and cotoniero destruction.

The invention is illustrated by the following examples. All quantitative data are mass parts, unless otherwise indicated.

Example 1. The connection 101 ( method A). 7.2 g (18 mmole) of 2,2-methylene-bis/6-tert-butyl-4-METHYLPHENOL/monoacrylate dissolved in 70 ml of dichloromethane. To this solution at room temperature (RT) is slowly added dropwise 2,17 ml (20 mmole) of benzylamine. Immediately thereafter the mixture is stirred for 3 hours at RT. Evaporate the solvent and carry out the chromatography fractions on silica gel (solvent: hexane), 6,63 g (66%) of compound 101 as a white powder. The melting point is 124-126oC.

Connection 102-104 obtained in example 1 described manner.

Example 2. The connection 105 ( method A).

In a round bottom flask with a magnetic stir bar and a refrigerator in an argon atmosphere add 16,57 g (42 mmole) of 2,2-methylene-bis/6-tert - butyl-4-METHYLPHENOL/monoacrylate and 2.17 ml (20 mmole) of benzylamine in 150 ml of dichloroethane. The reaction mixture overnight to boil education phlegmy then using a vacuum rotary evaporator. Chromatography carried out on silica gel (Belogo powder. The melting point is 70-76oC.

Connection 106-110 obtained by the method described in example 2.

Example 3. Getting connection 111 ( method A).

A mixture of 4.6 g (8.3 mmole) of 2,2'-ethylidene-bis/4,6-di-tert-amylphenol/- monoacrylate and 1 g (4,16 mmole) of N,N-dibenziletilendiaminom stirred for 4 hours at 140oC. After cooling to RT conduct chromatographic analysis of the product on silica gel (solvent:hexane), 5,15 g (93%) of compound 111 in the form of amorphous powder. The melting point is 129-134oC.

Example 4. The connection 112 (Method C),

a) obtaining 2,4-di-tert-butyl-6/1-(3,5-di-tert-butyl-2-hydroxyphenyl)-ethyl/-phenyl ester 3-chloropropionic acid.

< / BR>
In a 250 ml round bottom flask with a magnetic stir bar, refrigerator and counter gas bubbles injected to 21.9 g (50 mmole) 2,-2'-ethylidene-bis/4,6-di-tert-butylphenol/ and 48 ml (500 mmol) of the chloride of 3-chloropropionic acid in 100 ml of xylene. The mixture is heated for 15 hours to form phlegmy (emphasis HCl). The remainder of the acid chloride and the toluene is distilled off. Crystallization of the residue in acetonitrile allocate to 15.8 g (60%) received monoether 112 in the form of a side of the powder. The melting point of the composition is To a solution of 4.5 g (8.5 mmole) of the compound a (example 4A) in toluene (30 ml) and inclination in a nitrogen atmosphere at RT was added dropwise 1.63 g (to 18.7 mmole) of the research. The reaction mixture is stirred for one hour at 70oC, cooled to RT, filtered and evaporated. Crystallization of the residue in hexane allot of 3.9 g (80%) of compound 112 in the form of a white powder. The melting point is 150-152oC.

Example 5. The connection 113 ( method A).

A mixture of 19.7 g (0,04 mole) 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/-monoacrylate ( method of obtaining see EP-A-500 S) and 6,72 g (0,052 mole) of octylamine heated to 115oC. the Obtained colorless solution is stirred at this temperature for 30 minutes. Immediately after this, add 50 ml of ethanol. Upon cooling to RT crystallized product interaction. After filtration and drying under vacuum gain of 21.9 g (88%) of compound 113 in the form of a white powder. The melting point is 102-104oC.

Connection 114, 115 and 116 receive the same manner as in example 5 method.

Example 6. Getting connection 117 (Method A).

In a 200-ml flask for sulfation c thermometer, stirrer, reflux condenser and addition funnel under nitrogen atmosphere enter 6,41 g (13 mmole) of 2,2'-ethylidene-bis/4,6-di-tertbutylphenol/monoacrylate, 2 g (14.3 mmole) of the hydrochloride glycinamido ether and 50 ml ativanativan at this temperature for 5 hours. The resulting suspension was diluted with 25 ml of hexane and filtered salt. After the solvent is evaporated in a vacuum rotary evaporator and crystallization obtained from the hexane solution of the product emit 3.7 g (48%) of compound 117 as a white powder. The melting point is 121-122oC.

Example 7. The connection 118 ( Method A).

The mixture 6,92 g (14 mmol) of 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/-monoacrylate and 0,89 g (7.7 mmol) of 1,6-diaminohexane in 40 ml of acetic ether is heated for 30 minutes to form phlegmy. Immediately thereafter the solvent is evaporated. Crystallization of the residue from acetonitrile selected 5 g (65%) of compound 118 as a white powder. The melting point is 148oC.

Example 8. The connection 121 ( Method B).

A mixture of 2.05 g (12 mmole) 3-/2-oxopiperidine/-propionic acid (see Dado, G. P. Gellman, S. H.; J. Am. Chem. Soc. 116(3), 1054-62, 1994), 4,4 g (10 mmol) of 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/, of 2.06 g (10 mmol) of dicyclohexylcarbodiimide and 50 mg dimethylaminopyridine in 60 ml of dichloroethane is heated for 15 hours to form phlegmy. Immediately thereafter filtered emitted urea and evaporate the solvent. Crystallization of the residue is em 217-223oC.

Example 9. The connection 122 (Method A).

A mixture of 6.6 g (13 mmol) of 2,2-ethylidene-bis/4,6-di-tert-butylphenol/- monoacrylate, 4G (23.5 mmole) of O-benzyl-hydroxylamine-hydrochloride and 38 ml (27 mmole) of trialanine in 70 ml of dichloroethane is stirred for 8 hours at 65oC. Then the reaction mixture was diluted with 10 ml of hexane, salt is filtered off and the solvent is removed on a vacuum rotary evaporator. Crystallization of the residue from methanol allocate 4.6 g (55%) of compound 122 as a white powder. The melting point is 123oC.

Example 10. Getting connection 201 (Method A).

In a round bottom flask (volume 250 ml) under nitrogen atmosphere enter the 5.65 g ( 33 mmole) of 4-hydroxy-1,2,2,6,6-pentamethylpiperidine in 85 ml of tetrahydrofuran. The solution is cooled to 0oC and pin 5.6 ml (9 mmole) of 1.6 N solution of utility in hexane. The obtained white suspension is admixed within 30 minutes, and immediately thereafter slowly added dropwise a solution of 11,84 g ( 30 mmol) of 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/monoacrylate in 65 ml of tetrahydrofuran. The obtained yellow solution is stirred for 3 hours at RT. Then the reaction mixture is evaporated, poured into aqueous saturated solution of chloride ammonium vacuum rotary evaporator. Chromatography of the residue (SiO2: Hex/HER 9:1 ---> 1:1) allocate 11,06 g (65%) of compound 201 as a white powder. The melting point is 104-105oC.

Connections 202 and 203 receive by analogy with the method described in example 4.

Example 11. Getting connection 204 ( Method B).

a) obtaining a 3-octyloxybenzoic acid

To the colorless solution is 39.1 g (0,3 mol) octanol and 1.2 ml (2,9 mole) hydroxide designed (40% solution in water) at RT under nitrogen atmosphere for 25 minutes was added dropwise to 21.7 ml of 0.33 mole) of Acrylonitrile (Ekaterini process 40oC). After the addition is continued stirring at RT advanced for 25 minutes. The excess Acrylonitrile is removed by distillation (vacuum rotary evaporator). The obtained 3-octyloxyphenyl (light yellow liquid; 97% and dissolved in 150 ml of concentrated hydrochloric acid and 150 ml of acetic acid, the solution is heated at 85oC for 3 hours. The mixture is cooled, poured into 100 ml of water and extracted with acetic ether. Separate the organic phase, washed aqueous saturated solution of NaCl, dried over Na2SO4and use a vacuum rotary evaporator. Get 60 grams of 3-octyl-oxopropionate the 65,31 10,96

defined 64,94 11,09

b) In 100-ml round bottom flask with a magnetic stir bar and a refrigerator in an argon atmosphere add 7,08 (35 mmole) of 3-octyloxybenzoic acid (see example 11a) in 50 ml of toluene. To this solution was added with 7.6 ml (18.5 g, 105 mmole) of thionyl chloride. The mixture is slowly heated to 90oC (HCl formed and SO2) and stirred at this temperature for 2 hours. The next 30 minutes, stirred only in the stream of argon. When restoring pressure (20 mbar) is distilled off excess thionyl chloride and toluene. The residue (7 g of the chloride of 3-antioxidative acid) dissolved in 50 ml of toluene and add 10,97 g (25 mmole) of 2,2'-ethylidene-bis/4,6-di-tert-butyl-phenol/. To this solution at 10oC pin of 4.9 ml (35 mmol) of triethylamine. After 10 minutes the mixture is heated to RT and RT, stirred for 1 hour and 30 minutes. After the reaction mixture was filtered through cellit, and the filtrate is passed through a vacuum rotary evaporator. The remainder is added to 30 ml of acetonitrile, where distilled connection 204. Sduw and drying of the product allow 14,05 g (90%) of compound 204 as a white powder. The melting point of 114 suppliesoC.

Connections 205 and 214 receive on the analogy of example 11.

160oC). The resulting suspension is heated for 1 hour at 80oC. After cooling to PT add 10 ml of water (dissolved salt). Separate the organic phase, washed with water, dried over Na2SO4and use a vacuum rotary evaporator. Crystallization of the residue (10 g) in 20 ml of acetonitrile emit 6.8 g (73%) of compound 204 as a white powder. The melting point is 114-115oC.

Example 13. Getting connection 204 (Method B).

B 50 ml round bottom flask c magnetic stir bar and refrigerator are placed 12,18 g (0.05 mole) 3-octyloxybenzoic acid (83 wt.%) of 4.7 ml (0,065 mole) of thionyl chloride and 0.11 g (0.5 mmole) of chloride of benzyltriethylammonium. The colorless solution is stirred for 10 minutes at RT (formed HCl + SO2; endotherm: Ti 12oC). Heated to 65oC in a stream of nitrogen, and stirred at this temperature t (acid chloride) is added 18 g level (0.041 mole) of 2,2'-ethylene-bis/4,6-di-tert-butylphenol/. The mixture is heated to 140oC (formed HCl) and stirred at this temperature for 30 minutes, continue stirring in a light stream of nitrogen. The obtained brown liquid is cooled to 100oC and add 70 ml of ethanol. While cooling in an ice bath, distilled product. After filtration and drying under high vacuum, receive a 20 g (78%) of compound 204 as a white powder. The melting point is 115oC.

Example 14. Getting connection 215 ( Method B).

a) Obtaining 3-(2-butoxy-ethoxy)-propionic acid.

To a solution of 3.8 g (32 mol) of 2-butoxyethanol in 2 ml of tetrahydrofuran at 10oC in an atmosphere of nitrogen was added dropwise 2 ml (3.2 mmole, 10 mol.%) a 1.6 N solution of utility. The solution is stirred for 5 minutes at 10oC. then add 2.5 ml (38 mmol) of Acrylonitrile. The reaction mixture is heated to 55oC and stirred at this temperature for 2.5 hours. Re-add 0.25 ml (3.8 mmole) of Acrylonitrile and the mixture was stirred at 55oC for one hour. After cooling to RT the mixture was poured into water, acidified with 2N HCl (2 ml) and extracted with toluene, the organic phase is washed with aqueous NaCl solution, dried on magnesium sulfate and evaporated in vacuum. The obtained 3-(2-butoxy-ethoxy) the brown solution is cooled to RT, diluted with water, washed with aqueous NaCl solution, dried over MgSO4and evaporated in vacuum, get 3.2 g (53%) of 3-(2-butoxy-ethoxy)-propionic acid as light brown liquid.1H-NMR (300 MHz, CDCl3: (ppm) of 0.91 (t, J = 7,3 Hz, 3H), of 1.36 (Sextet, J = 7,66 Hz, 2H), 1.57 in (Quintet, J = 7.8 Hz, 2H), 2,65 (t. J = 6.3 Hz, 2H), 3,47 (t, J = 6.6 Hz, 2H), 3,56-3,65 (dxm, 4H), of 3.77 (t, J = 6.3 Hz, 2H), AND 9.6 (S, wide, 1H)

b) To a solution of 6.6 g (15 mmol) of 2,2-ethylidene-bis/4,6-di-tert-butylphenol/, 3,76 g (18 mmol) of 3-(2-butoxy-ethoxy)-propionic acid and 0.1 g (0.8 mmole, 5 mol. %) dimethylaminopyridine in 60 ml of ethylene glycol at RT under nitrogen atmosphere suppress a solution of 3.1 g (15 mmole) of dicyclohexylcarbodiimide in 10 ml of telengard. The mixture was stirred at RT for 15 hours. Then separate the urea and evaporate the solvent. Crystallization from acetonitrile allocate 5 g (54%) of compound 215 in the form of a white powder. The melting point is 88-91oC

Example 15. Getting connection 216 (Method B).

a) In a 250 ml round bottom flask under nitrogen atmosphere was placed 10,02 g (55 mmol) 3-/3-(2-carboxy-ethoxy)-propoxy/-propanoic acid (see R. V. Christian und R. M. Hixon J. A. C. S. 70, 1933, (1948)) in 100 ml of toluene. To this suspension is added to 13.2 ml ( 180 mmol) thionylchloride, the mixture is slowly heated (about 40 minutes) to 90oC (HCl formed and SOoC in a stream of argon for 45 minutes. Separate the excess thionyl chloride and toluene and produce crude chloride bis-acid.

b) In 350 ml flask for sulfation in the atmosphere of argon for example 15A described chloride bis-acid (55 mmol) and 43,87 g (0.1 mol) of 2,2'-ethylidene-bis-/4,6-di-tert-butylphenol/ add to 100 ml of toluene. This solution is cooled to 10oC and slowly added dropwise and 16.7 ml (120 mmol) of triethylamine. Upon completion of the addition (50 minutes) the mixture is heated to 70oC and stirred at this temperature over night.

Filter out triethylenediamine and the filtrate is evaporated.

Chromatography on silica gel (solvent: Hex/EE 40:1) allows you to allocate 21 g (40%) of compound 216 in the form of amorphous powder. The melting point is 94oC.

Connection 217 and 218 receive by analogy with the procedure outlined in example 15 by the way.

Example 16. Getting connection 219 (Method B).

a) Obtaining 3-(2,4-di-tert-butylphenoxy)-propionic acid.

To a solution of 9.7 g (47 mmol) of 2,4-di-tert-butylphenol and 0.6 ml (1.5 mmole) hydroxide designed (40% solution in water) at RT under nitrogen atmosphere for 20 minutes pin of 6.2 ml (94 mmole) of Acrylonitrile. Pic is giving 2.5 hours. Then separate the excess of Acrylonitrile (vacuum rotary evaporator). The resulting crude 3-(2,4-di-tert-butylphenoxy)-propionitrile dissolved in 40 ml of concentrated hydrochloric acid and 40 ml of acetic acid and heat the solution for 10 hours at 100oC. the Mixture is cooled, poured into 60 ml of water and extracted with a mixture of hexane and acetic ester 1:1. Separate the organic phase, washed with aqueous saturated NaCl solution, dried over sodium sulfate and evaporated on a vacuum rotary evaporator. Distillation of the residue (60oC/ 0.1 mbar) to provide 10 g (77%) received salt as a white powder. The melting point is 105-106oC. 1-H-NMR (300 MHz) CDCl3: = 2,89 (t, J = 6.2 Hz, 20N, COOH-), 4,27 (t, J = 6.2 Hz, 2 H, Ar-O ).

b) In a round bottom flask with a fridge and a magnetic stirrer was placed 10 g (36 mmol) of 3-(2,4-di-tert-butylphenoxy)-propionic acid, 13,1 g (30 mmol) of 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/ 0.2 g (1.6 mmole) 5 mol%) dimethylaminopyridine and 180 ml of dichloroethane. To this solution at RT under nitrogen atmosphere was added dropwise a solution of 6.2 g (30 mmol) dicyclohexylcarbodiimide in 20 ml of dichloroethane. The mixture is stirred for 15 hours at RT. Filtered precipitated urea and the solvent is distilled off. Cristallization>C.

Connection 220 from commercially available 3-phenoxypropionic acid and 2,2'-ethylidene-bis/4,6-di-tert-(butylphenol/ receive analogy described in example 16b method.

Example 17. Getting connection 221 (Method B).

a) obtaining a 3-cyclohexylhydroxylamine acid.

The mixture was 32.8 g (to 0.29 mol) cyclohexasiloxane, 26 g (of 0.26 mole) acrylate, 26 ml (0,052 mole) of 2N KOH solution in ethanol and 150 ml of ethanol was stirred at 60oC for 60 hours and then separated on a vacuum rotary evaporator. The residue (orange) is dissolved in 175 g (0,31 mole) of a 10% solution of KOH in ethanol, heated at 60oC and for 1 hour. Separate the solvent and the solid residue is placed in water, acidified with 15 ml of concentrated hydrochloric acid and extracted with acetic ether. The organic phase is washed with water, dried over Na2SO4and sent to a vacuum rotary evaporator. The distillation residue is separated and 11.8 g (25%) of the acid obtained as an orange liquid. Boiling point is 135oC/ 0,05 mbar.

Elemental analysis:

With% of theory. 58,36 practical use. 58,47

H% theoretical. 8,16 practical use. 8,30

N% of theory. 7,56 practical use. 7,13

b) the Method is carried out according to example 16b, pret-butylphenol/ in the form of a white powder of 15.3 g (72%) of compound 221. The melting point is 118-121oC (methanol).

Connection 222-224 receive by analogy with the method B described in example 13.

Connection 225 receive by analogy with the method B described in example 14b.

Example 18. The connection 301 (oxidation tiefer obtained by the method (A).

a) Obtaining 2-tert-(butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenylethyl-4 - metilfenidato ester 3-(octylthio)-propionic acid.

In a 200 ml flask to dissolve sulfation 9,86 g (25 mmole) of 2,2'-methylene-bis/6-tert-butyl-4-METHYLPHENOL/monoacrylate, was 4.02 g (27.5 mmol) actantial in 50 ml of toluene. When RT was added dropwise 0.75 ml (1.25 mmole) of 1.7 N solution of tert-pentolate potassium in toluene. After that, the reaction mixture is heated to 55oC and stirred at this temperature for 1 hour. The mixture is cooled to RT, poured into diluted hydrochloric acid (0,1 N) and repeatedly extracted with acetic ether. The organic phase is combined, dried over sodium sulfate, and served on a vacuum rotary evaporator. After separation of unreacted bisphenol a (tube with ball extension for distillation 200oC/10 mbar), get 11,35 g (84%) of the obtained compound as a pale yellow oil.

Example 19. Getting connection 302 (Oxidation obtained by way of tiefer).

In a 250 ml flask for sulfation in the atmosphere of nitrogen dissolved at 10.82 g (20 mmol) of the compound from example 18 in 80 ml of dichloromethane. To this solution was added dropwise at -15oC solution 13,82 g (42 mmole) of m-chloroperbenzoic acid in 120 ml of dichloromethane. The thick suspension is stirred while warming to RT, poured into aqueous saturated sodium bicarbonate solution and repeatedly extracted in dichloromethane. Allocate the organic phase, washed with water, dried over sodium sulfate and sent to a vacuum rotary evaporator. Crystallization of the residue from isopropanol allocate 8,05 g (70%) of compound 302 in seeing 401 ( Method A).

A mixture of 12.3 g (0,025 mol) 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/ monoacrylate, 2,07 g (0,03 mole) of 1,2,4-triazole and a few drops of pyridine is stirred at 150oC for 3 hours. After that the reaction mixture is cooled to 100oC, is mixed with 30 ml of isopropanol and filtered. Upon cooling to RT, distilled connection 401. After separation and drying receive in the form of a white powder compound 401. The melting point is 160-162oC.

Connection 402 receive by analogy with the method described in example 20, the reaction is carried out at a temperature of from 170oC to 150oC.

Example 21. Getting connection 403 ( Method B).

To the colorless solution 4,39 g (10 mmol) of 2,2'-ethylidene-bis/4,6-di-tert-butylphenol/, 2.5 g ( 13 mmol) of 3-benzotriazol-1-yl-propionic acid Wiley et al; J. A. C. S 76, 4933 (1954)) and 2.02 g (20 mmol) of triethylamine in 40 ml of tetrahydrofuran was added dropwise at 50oC in nitrogen atmosphere of 0.68 ml (1,15 g, 7.5 mmol) of phosphorylchloride. The resulting suspension is stirred for 5 hours before flavobacteria. After cooling to RT, the reaction mixture is filtered off from the salts and evaporated on a vacuum rotary evaporator. The residue is poured into water and twice extracted with acetic ether is on a vacuum rotary evaporator.

Crystallization of the residue from ethanol allot of 3.9 g (80%) of compound 404 in the form of a white powder. The melting point is 174-178oC.

Example 22. Getting connection 404 ( Method A).

A mixture of 14,78 g (0,03 mole) 2,2'-ethylidene-bis/4,6-di-tert-butyl-phenol/monoacrylate, 5,02 g (0,03 mole) of 2-mercapto-benzothiazole and a few drops of pyridine in 25 ml of dichloroethane is stirred for 15 hours before flavobacteria. The reaction mixture is evaporated on a vacuum rotary evaporator. After chromatographic purification (SiO2; Hexane/ethyl acetate: 40:1) and crystallization from acetonitrile get the 7.65 g (39%) of compound 404 in the form of a white powder. The melting point is 123-128oC.

Example 22A. Getting connection 405.

The solution of 14,78 g (0,03 mole) 2,2'-ethylidene-bis/4,6-di-tert-butyl-phenol/monoacrylate, 5,02 g 2-mercapto-benzthiazole and a few drops of pyridine in 25 ml of dichloroethane is stirred for 15 hours at 90oC. After that the reaction mixture is evaporated on a vacuum rotary evaporator. After chromatographic purification of the residue (SiO2hexane/ethyl acetate:40:1) allocate to 7.7 g (39%2 connections 405 in the form of amorphous powder. The melting point after crystallization from acetonitrile costall powdered polypropylene (Profax 6501), stable 0.025% of n-octadecylamide ester 3-/3,5-Lee-tert-butyl - 4-hydroxyphenyl/propionic acid, (index melting 3.2 measured for of 2.16 kg at 23oC) are mixed with 0.05% pentaerythritol - Il-tetrakis-/3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate/), 0.05 % of calcium stearate, 0.03% of dihydrochalcone /Mg4,5Al2(OH)13CO33,5 H2O and 0.05% of the compound from table 1. These compounds ekstragiruyut in the extruder with the cylinder diameters of 20 mm and a length of 400 mm at 100 revolutions per minute, with 3 areas of the vulcanization are separated according to the following temperatures: 260o, 270o, 280oC. the Extrudate is fed to the refrigerator through a water bath and subsequently granulated. This extrudate re ekstragiruyut. After 3 extrusions measure the index of fusion (at 230oC for 2,16 kg). A strong increase in the index melting witness the collapse of the polymer chains, i.e. weak stabilization. The results are shown in table 2.

Example 24. Stabilization of elastomers (Test of Brabender).

Styrene-butadiene-styrene elastomer (Finaprene 902) is mixed with the stabilizers shown in table 3, and plasticity in plastograph of Brabender at 200orerave, due to cross-linking of the polymer occurs fast permanent increase in torque over time for the softening. The action of the stabilizer appears to extend a short period of time during which the torque remains constant.

The results are shown in table 3.

Example 25. Stabilization of styrene-butadiene block copolymers.

During thermal oxidation effects on styrene-butadiene block copolymer is the crosslinking of the rubber phase. This binding leads to an increase in the viscosity of the melt and, consequently, pressure extrusion during processing in the extruder or in the car for casting under pressure.

Check stability during processing is often performed for the styrene-butadiene block copolymers in a capillary rheometer. Thus polymerizat as during extrusion, in the form of a melt press nozzle.

25 g of the granules of styrene-butadiene block copolymer (K-Resin KR-01von Phillips Petroleum), containing 0.2 % n-octadecyl-3/3',5'-di-tert-butyl-4'-hydroxyphenyl/propionate and 0.6% Tris/Nonylphenol/phosphite dissolved in 250 ml of cyclohexane at room temperature.

The stabilizer, the amount of which lead the Ute at 60oC and 0,013 bar.

The polymer is pressed into plates with a thickness of 2 mm at 180oC, plates are punched circular samples with a diameter of 8 mm. These samples are placed in a receiver channel of a capillary rheometer typeKeyeness Galaxy V and conduct measurements at 250oC with a shear rate of 14 594 sec-1. After 6 minutes register of apparent shear rate as a function of time for 30 minutes. Rise curve (/tinPa C/min) is a measure of the degree of polymer crosslinking and is directly dependent on the action of the stabilizer. The smaller this value, the more effective the stabilizer.

The results are shown in table 4.

1. Derivatives ethers of bisphenol of the General formula (I)

< / BR>
where the substituents of the radical R1have the same values and mean C1-C5-alkyl or C5-C8-cycloalkyl;

the substituents of the radical R2have the same values and mean C1-C5-alkyl;

the substituents of the radical R3each independently of one another denote hydrogen or C1-C4-alkyl;

R4is hydrogen or C1-C4-alkyl;

R5- R8is hydrogen;

n = 1 or 2, and if n = 1, it means any SUB> or as well As means unsubstituted or C1-C4-alkyl substituted heterocyclic radical having a free valency on the nitrogen atom, L1- C1-C18-alkyl, C3-C10-alkyl, which is interrupted in the chain by oxygen, C5-C8-cycloalkyl, tetrahydrofurfuryl or a group of formula IIA or IIb;

< / BR>
L2- C1-C18-alkyl, -OH-substituted C2-C4-alkyl, C7-C9-phenylalkyl, the group -(CH2)pCOO-X2or a radical of the formula IIb; L3is hydrogen, C1-C18-alkyl, -HE-substituted C2-C4-alkyl, C7-C9-phenylalkyl or a radical of the formula IIb or L2and L3taken together, - C3-C6-oxoalkyl or C3-C6-alkylen, interrupted in the chain by oxygen, L4- C7-C9-phenylalkyl, L5and L6together with the binding carbon atom form a C5-C8-cycloalkylation ring, L7- C1-C10-alkyl, L8is unsubstituted or C1-C4-alkyl substituted 2-benzoxazolyl or unsubstituted or C1-C4-alkyl substituted 2-benzothiazolyl; T1- T4each independently is hydrogen or C1-C4-alkyl; T5is hydrogen or C1-C2< / BR>
-O-G7-O-(IIIc) or >N__G12(IIIf)

G1and G3each independently is hydrogen, C7-C9-phenylalkyl or a radical of the formula IIb;

G2- C2-C8-alkylen or monocyclic saturated hydrocarbon radical with two free valences and containing 10 carbon atoms;

G7- C2-C8-alkylene or C4-C12-alkylen, interrupted in the chain by oxygen, and G12- C7-C9-phenylalkyl or a group of formula IIb.

2. Stable composition, characterized in that it contains a polymer that is sensitive to oxidative, thermal and induced light of destruction, and from 0.01 to 30.0% of the total mass of the specified polymer compounds of the formula (I) under item 1.

3. Stabilized composition according to p. 2, characterized in that the polymer used as the polyolefin.

4. Stabilized composition according to p. 2, characterized in that the polymer used polymerized in a solution of polybutadiene rubber.

5. Stabilized composition according to p. 2, characterized in that the polymer used polymerized in solution styrene-butadiene copolymer or a styrene-butadiene block copolymers.

7. The method of stabilization of the polymer is sensitive to oxidative, thermal and induced light degradation, characterized in that the specified polymer is injected from 0.01 to 10.0% of the total weight of the polymer of the compounds of formula (I) under item 1.

 

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The invention relates to the field of petrochemicals, more specifically to methods for stabilizers for rubbers, thermoplastic elastomers and rubbers

The invention relates to a previously undescribed perchlorates of diphenylethylenediamine General formula (I)

< / BR>
where n= 0,1; R1, R6the atom of hydrogen or halogen, C1-C6alkyl, C1-C6alkoxy or di(C1-C6)alkylamino; R2, R5= a hydrogen atom or halogen, C1-C6- alkoxy - or actigraphy; R3, R4the atom of hydrogen or C1-C6alkoxygroup; R7=R8=R9a hydrogen atom, or R7+R9=(CH2)1-3and R8=H; if n=0 have the General formula (Ia-C):

< / BR>
(perchlorate 1,5-diphenyl-3-ethoxymethyleneamino), and when n=1 have the General formula (I-R):

< / BR>
(perchlorate 1,7-diphenyl-3,5-diethoxymethylsilane) and which can be used as a promising synthons in organic synthesis, and in particular in the synthesis of fluorescent dyes (Durder J. A

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