Isocyanate mixtures blocked by dimethylpyrazole

FIELD: chemistry of polymers, chemical technology.

SUBSTANCE: invention relates to mixtures consisting of blocked polyisocyanates designated as hardening agents in monocomponent lacquers of hot drying and comprising: (a) blocked polyisocyanate based on 1,6-diisocyanate hexane; (b) blocked polyisocyanate based on cycloaliphatic diisocyanates chosen from group comprising 1-isocyanato-3,3,5-trimethyl-5-ixocyanatomethylcyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,6-bis-isocyanatonorbornane, 2,5-bis-isocyanatonorbornane, 1,4-bis-isocyanatomethylcyclohexane and their mixtures, and (c) 3,5-dimethylpyrazole as a single blocking agent of agent of polyisocyanates named in (a) and (b). Blocked polyisocyanates are taken in the weight ratio (a) : (b) = 1:(1.8-2.2). Using mixtures of blocked polyisocyanates provides preparing clear lacquers with good acid resistance, stability against scratching and thermal yellowing.

EFFECT: improved and valuable properties of agents.

1 cl, 6 ex

 

The invention relates to certain mixtures of polyisocyanates which are blocked 3,5-dimethylpyrazole, and their use as a means of forming cross-links in the one-component lacquers hot drying, in particular automotive clear lacquer.

The compositions of polyacrylate resins containing Oh-groups, with blocked polyisocyanates or mixtures of melamine-formaldehyde resins and blocked polyisocyanates as binders for one-component" hot drying varnishes known. Properties derived from these varnishes together are defined as a type polyisocyanate component and a blocking means, because, as you know, a certain share of the latter always remains in the lacquer.

3,5-Dimethylpyrazol, abbreviated to SLE, for the first time is called as a means of blocking the NCO-groups have hot drying varnishes, in EP-A 0159117 B1. Comparison of the blocking means, such as butanonoxime, 1,2,4-triazole and SLE, described in the journal "Paints and varnishes" (Farbe &Lack), 1996 edition, volume 102, No. 7, p.51-58 (Engbert and others). This study shows that DMP has the advantage compared with butanonoxime relative to the temperature of the hot drying and resistance to thermal yellowing. Further, it was found that the acid resistance of transparent varnish based on MDI IPDI blocked SLE, it is considered appropriate and is only slightly mouth is Paeth kislotostojkuju similar two-component lacquer (without blocking the means). On the resistance to scratching is not reported.

The acid resistance and resistance to scratching are important properties of automotive clear lacquer as the uppermost layer, which, for example, must withstand the impact of the environment, as well as line conditions for car washing. In the above-cited study, transparent lacquer, in which the blocking means is used 1,2,4-triazole, shows a markedly inferior properties, for example, in kislotostojkuju.

In the publications of the conference European Conference on Coatings, Berlin 1999, Vincent Verlag, "Blocked Isocyanates - Assessment Methods and Recent Developments", Remmer and other Chemicals Baxenden" reported mainly on the temperature of the release of isocyanates, blocked SLE. However, issues such as can be made transparent lacquer polyisocyanate, blocked SLE, with good resistance to scratching, and with good acid resistance, are not discussed.

The objective of the invention is the development of blocked polyisocyanates, which can be recycled to the hot drying varnish with

1) good acid resistance,

2) good resistance to scratching,

3) good resistance to thermopolae and

4) a relatively low temperature of the hot drying 130-150°With (at 30 min).

This task can be solved with what omashu blocked mixtures of the polyisocyanates according to the invention.

The subject invention are a mixture of blocked polyisocyanates containing:

a) the blocked polyisocyanates based on 1,6-diisocyanatohexane (GDI),

b) the blocked polyisocyanates based on cycloaliphatic diisocyanates and

(C) 3,5-dimethylpyrazol as the sole locking means mentioned under a) and b) polyisocyanates, characterized in that the blocked polyisocyanates are in a weight ratio of a):b)=1:1,8-2,2.

The subject of the invention is also the use of mixtures of blocked polyisocyanates according to the invention in a mixture with melamine-formaldehyde resins during curing varnishes hot drying, characterized in that it is applied to 50% of a mixture of blocked polyisocyanates (a)+(b) based on the entire component is a hardener.

And, finally, the subject invention is the use of a mixture of blocked polyisocyanates according to the invention as component-hardener-component varnishes hot drying, in particular for automotive clear lacquer.

The mixture according to the invention are a combination of flexible blocked polyisocyanate component a) and rigidly blocked polyisocyanate component b), and mixing ratio a:b ranges from 1:1.8 to 1:2.2 to. Preferably, the ratio a:b=1:2.

As a researcher is as polyisocyanates for component a) are considered known in themselves lacquer polyisocyanates, having biuret-, which is, allophanate-, iminoimidazolidine-(asymmetric trimer), urethane - and/or uretdione group, based on 1,6-diisocyanatohexane (GDI) with an NCO content of 19 to 25 wt.%. Preferred lacquer polyisocyanates containing predominantly, which is group-based GDI, in short - trimeresurus GDI.

As polyisocyanates for component b) are considered known in themselves, which contains-, allophanate-, uretdione and urethane groups lacquer polyisocyanates based on cycloaliphatic diisocyanates with a content of NCO 12-23 wt.%. Examples of cycloaliphatic diisocyanates are 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (IPDI), bis(4-isocyanatophenyl)methane (N12MDI or Desmodur W®/Bayer AG), 2,6 - or 2,5-visitorinfo-norbornene or 1,4-bis-isocyanatomethyl-cyclohexane. Can be used 1:1-mixture of polyisocyanates based on IPDI and Desmodur W®. Are preferred, which contains mostly group lacquer polyisocyanates based on IPDI and Desmodur W®. Lacquer polyisocyanate based trimeresurus IPDI is a solid resin with a NCO content of 17 wt.% and traded so in the form of a 70%aqueous solution with an NCO content of about 12 wt.%. Containing isoci suratnya group polyisocyanate based on Desmodur W ®described in example 6.

Block NCO-group tool - 3,5-dimethylpyrazol is a colourless solid (TPL 107°). It can relatively easily and quantitatively obtained by condensation of 1 mole of acetylacetone with 1 mol of hydrazine hydrate is added. However, for blocking isocyanate you can use warm reaction solution of the adduct (Edukt), as described, for example, in EP-A 0713871 B1. According to this invention all of the isocyanate groups used isocyanates blocked, so that the mixtures according to this invention there is no free isocyanate groups.

The mixture according to the invention, the blocked polyisocyanates are mixed with conventional methods of organic polyhydroxylated compounds in one-component lacquer binder, so that the number of blocked NCO-groups is combined with the appropriate number of Oh-groups. The stoichiometric ratio of blocked NCO-groups: HE-groups is 1:1.

If a single component lacquer hot drying mainly sew with melamine-formaldehyde resin and as a modifying component is a mixture of polyisocyanates, blocked according to this invention, the mixing ratio of the binder should be determined empirically. The fulcrum for the mass distribution of polyacrylate: the chalk is but-formaldehyde resin: a mixture of blocked polyisocyanates network is given in the examples, the ratio of 70:20:10 wt.% in the calculation of the corresponding solid resin. This mix crosslinking components linking agent, namely, melamine-formaldehyde resin and a mixture of blocked polyisocyanates are in a weight ratio of 2:1. Depending on the desired effect, do we prefer mostly the stitching due to melamine-formaldehyde resin, or joining blocked polyisocyanates, it is above the mixing ratio may vary between 5:1 and 1:2.

Using mixtures of blocked polyisocyanates according to the invention are obtained transparent varnishes with good acid resistance, resistance to scratching, and resistance to thermopolae.

Examples

Example 1

Describes the structure component of the blocked polyisocyanates

Execution:

Take a polyisocyanate and a mixture of solvents. With stirring the solid portions DMP at a temperature of 75-85°C and stirred for about 1 hour at 80°C, until no longer be detected NCO-groups. Get clear, slightly yellowish (Hazen 30-40) solution of the above parameters.

Execution:

Take a polyisocyanate and a mixture of solvents. With stirring the solid portions DMP at a temperature of 85-95°C and stirred for about 1 hour at 95°until on is not longer detected NCO-groups (IR spectrum). Get clear, slightly yellowish solution with the above parameters.

Example 2 (according to the invention)

Presented to the mixture according to the invention from two blocked polyisocyanate components of examples 1a+1B) in a weight ratio of 1:2, and made of them a lacquer binder.

A mixture of blocked polyisocyanates according to the invention is combined with the polyacrylate Desmophen®A VP LS 2009/1 (70%solution in butyl acetate, the content of 3 wt.%, 1 EQ. HE-groups = 566 g, Bayer AG) in a lacquer binder, as follows.

Example 3 (according to the invention)

Lacquer initial mixture is prepared as a mixture of blocked according to the invention polyisocyanates in accordance with example 2, and substance-by comparison, dried 30 min at a temperature of 140°and are evaluated on their kislotostojkuju, scratch resistance and resistance to thermopolae.

a) original Lacquer mixture

Composition [wt.%]Painted 1 (according to the invention)Lacquer 2 (comparison)
Desmophen®A VP LS 2009/1, 70%solution in BA38,436,7
The blocked polyisocyanate according to example 1A 9,8-
The blocked polyisocyanate according to example 1B24,637,3
72,874,0
Dibutyltindilaurate, 10% in xylene (Brenntag AG)a 4.94,8
Baysilone OL 17, 10% in xylene (Bayer AG)0,50,5
Modaflow, 1% in xylene (Monsanto Co San Luis)0,50,5
Tinuvin 292, 10% in xylene (Shiba Speciality chemical Inc. Basel)a 4.94,8
Tinuvin 1130, 10% in xylene (see above)9,89,6
1-Methoxypropylacetate/colonnata 100 (1:1)the 4.7a 3.9
Butylpyrocatechol1,91,9
100,0100,0

In both original lacquer mixtures the ratio of blocked NCO-groups to groups is 1.0. Unlike varnish 1 according to the invention in the varnish 2 is only one of the two blocked polyisocyanate components.

Lacquer original mixture of 1 and 2 in the form of clear lacquer is applied by spraying on the test metal sheets with a white water-soluble varnish base and dried 30 min at a temperature of 140° C.

b) Evaluation of Lac

Painted 1 (according to the invention)Lacquer 2 (comparison)
Acid [°]
(Gradient oven test method Daimler-Chrysler)
H2SO4that 1%5153
Resistance to scratching
(Laboratory wash installation, DFO1)- test method, standard DIN in preparation)
Original gloss20°90,691,4
Loss of gloss (Δ Shine) after 10 wash cycles30,340,6
Relative residual gloss[%]66,655,6
Resistance to thermopolae
(Colorimetric detection, CIELAB; DIN 6174)
Transparent lacquer on vocarstvo the Imam lacquer as the base, white
Initial yellowing[b]of-1.5-1,7
Yellowing after heating at 160°With over 300,30,4
min[Δb]
1)DFO German research society for surface treatment

As you can see, acid varnish-comparison with the value of 53°slightly better than the lacquer according to the invention with 51°that is a good value.

In contrast, when measuring the resistance to scratching of the residual gloss varnish 1 according to the invention is 11% higher than that of the varnish 2.

Both lacquer equally well resistant to thermopolae.

Example 4

Describes a binder, in which HE-containing polyacrylate cures primarily through melamine-formaldehyde resin and only 10 wt.% per binder with blocked MDI. As the optimal ratio of the three components of the mixture of the binder HE-containing polyacrylate: melamine-formaldehyde resin: the blocked polyisocyanate set the value for the solid resin 70:20:10. Also it shows that transparent varnish, which 10 wt.% the binder consists of a block the data according to the invention polyisocyanates, behaves better.

a) a Binder containing melamine-formaldehyde resin and the mixture is blocked according to the invention polyisocyanates

The communication componentAmount [g]Solid [g]The ratio of components
Desmophen®A VP LS 2009/1, 70%;46,5worth 32.5570
cf. example 2
Setamin US-138 BB-70, 70%in butanol,13,39,3120
Akzo-Nobel Rubber, Bergen op Zoom
The blocked polyisocyanate according to example 1A), 75%2,1of 1.57
The blocked polyisocyanate (b) according to example 1B), 60%5,23,12

As can be seen from the above examples, both blocked MDI are in the ratio according to the invention a:b=1:2.

b) Connecting with melamine-formaldehyde resin and a blocked polyisocyanate (comparison)

Amount [g]
The communication componentSolid [g]The ratio of components
Desmophen®A VP LS 2009/1, the 70%, cf. example 246,732,770
Setamin US-148 BB-70, 70%, see example 4A)13,39,320
the blocked polyisocyanate according to example 1A), 75%6,24,6510

C) Connecting only with melamine-formaldehyde resin as a means of matching (comparison)

The communication componentAmount [g]Solid [g]The ratio of components
Desmophen®A VP LS 2009/1, the 70%, cf. example 247,633,3270
Setamin US-148 BB-70, 70%, see example 4A)20,4of 14.2830

Example 5

Describes the source of a mixture of transparent varnish with two different mixed media knitting from melamine-formaldehyde resin/MDI, means joining melamine-formaldehyde resin and comparative tests of varnishes.

a) original Lacquer mixture

Composition, wt.% Varnish 3Lacquer 4Lacquer 5
the agreements. Fig. cf. prima)(cf. prims)(cf. prims)
Desmophen®A VP LS 2009/146,546,747,6
Setamin US-138 BB-7013,313,320,4
The blocked polyisocyanate (a) agreement. approx. 1A)2,16,2-
The blocked polyisocyanate (b) of the agreement. approx. 1B)5,2--
Dibutyltindilaurate, see example 3A)2,62,6-
p-Toluensulfonate, 10% in xylene, Merck-Suchard1,01,01,0
Baysilone OL 17, see example 3A)0,50,50,5
Modaflow, see example 3A)0,50,50,5
Tinuvin 292, see example 3A)5,15,15,2
Tinuvin 1130, see example 3A)10,210,210,4
1-Methoxypropylacetate/10,7the 11.6to 12.0
Colonnata
Butylpyrocatechol,3 2,32,4
100,0100,0100,0

Varnish 3 contains a mixture of blocked according to the invention polyisocyanates in an amount of 10 wt.% calculated on the solid binder. Lac 4, as well as lacquer 3 is a mixed means of crosslinking with melamine-formaldehyde resin/blocked polyisocyanate, but without the mixture of polyisocyanates according to the invention. Lacquer 5 is a means of stitching only with melamine-formaldehyde resin.

b) Evaluation of varnishes

The original mix of varnishes 3-5 are applied by spraying in the form of transparent varnish on the test metal sheets with a white water-soluble varnish base and dried for 30 minutes at 140°C.

Varnish 3Lacquer 4Lacquer 5
the agreements. Fig.(comparison)(comparison)
Acid [°]413836
(Gradient furnace; test method of the Chrysler-Daimler), H2SO4, 1 wt.%
Resistance to scratching
(laboratory wash installation, DFO test method, standard DIN in preparation)
Original gloss 20°91,9to 92.1for 95.3
Loss of gloss (ΔShine) after 10 cycles27,425,533,0
washing20°
Relative residual gloss[%]67,570,365,4
Resistance to thermopolae
(CIELAB; DIN 6174)
Initial yellowing[b]-2,0-1,9of-2.1
Yellowing after heating at 160°
for 30 min[Δb]0,40,20,4

In the above review lacquer 3 shows the high acid resistance (size 41°). However, this value is below 10°C, che is the means of stitching containing only the polyisocyanate according to example 3b). Lacquer 5 has the highest resistance to scratching (with residual gloss of 65.4%). Yellowing after warming up very slightly and all three variants of varnishes in order. Varnish 3 (according to the invention) were better than lacquer 4, and noticeably better than lacquer 5.

Example 6 (according to the invention)

Describes getting blocked SLE of trimerization Desmodur W®appropriate combinations of binder and evaluation of transparent varnish.

a) Preparation of blocked SLE of trimerized Desmodur W®

Original mix:

1) Trimerization

2.0 EQ. Desmodur W®=262,0 g
0.7 EQ. Trimerization using a 10%aqueous solution of Triton=-
1.3 EQ. Desmodur W®trimeresurus=262,0 g NCO:the calc. 20,8% calc. 20,3%
Butyldiglycol (BDGA)=65,5 g
1.3 EQ. Trimeresurus Desmodur W®=327,5 g NCO:the calc. 16,67% calc. 16,13%
1,0 EQ. Trimeresurus Desmodur W®, 80%in RIGA=260.4 g
2) Blocking
1,0 EQ. Trimeresurus Desmodur W®=260.4 g
of 1.05 mol of 3,5-dimethylpyrazole (SLE)=100,8 g
1-Methoxypropylacetate (MPA)=154,0 g
1,0 EQ. Blocked the DMP trimerized Desmodur W®=515,2 g
Solids content:309,12 g, 60 wt.%
Viscosity at 23°:1850 mPa.s
the content of blocked NCO-groups:8,15 wt.%

Execution:

1) Desmodur W®exempt from CO2by means of vacuum and stirred at 85°C. is added in small portions to 10%solution of Triton In n-butanol, first, about 2 ml, then such portions, so that the exothermic reaction is always maintained at a temperature of 85-90°C. After 3.5 hours of reaction at 90°and the catalyst consumption of 11.7 ml found the NCO content of 20.3 wt.%. The mixture is diluted with butylpyrocatechol and cool.

2) Trimeresurus Desmodur W®and MPA are at 80°C. With stirring contribute large portions SLE and left to interact at 90°From about 1 hour up until no longer be detected free NCO-groups (IR spectrum). Get the transparent slightly yellowish solution with the above parameters.

b) the mixture according to the invention from a locked flexibly and rigidly locked polyisocyanates in a mass ratio of 1:2 and lacquer binder as in example 2.

Amount [g]The solids content [g]The ratio a/bThe equivalent of blocked NCO-groups
The blocked polyisocyanate (a) agreement. example 1A) - base: GDI-trimerized140,2105,010,355
The blocked polyisocyanate (b) of the agreement. example 6A) - basis:332,3210,02to 0.645
Desmodur W®- trimerized
472,5315,01,000

Of the above mixture of cross-linking means according to the invention is formed of a varnish binder as in example 2, as follows:

Lacquer binder

The number gEquivalents of blocked NCO or HEReduced y to the number in g for lacquer original mix = 100 g
The blocked polyisocyanate (a) agreement. example 1A)140,20.3559,8
The blocked polyisocyanate (b) of the agreement. example 6A)332,30,69523,3
Desmophen®A VP LS 2009/1, 70%in butyl acetate, IT is equivalent to = 566566,01,00039,6
1038,572,7

This lacquer binder, as shown by example 3, processed with additives and solvents in a ready to spray clear lacquer and applied by spraying on the test metal sheets with a white water-soluble varnish base and subjected to a hot dryer for 30 minutes at 140°C.

C) Assessment of lacquer

Acid [°]50
(see example 3b), H2SO4,1%
Resistance to scratching
(see example 3b)
Original gloss20°90,9
Loss of gloss after
10 wash cycles20° 26,2
Relative residual gloss [%]71,2
Yellowing after heating at 160°C for 30 min (see example 3b)
[Δb]0,5

As you can see in comparison with varnish 1 according to example 3b) (GDI/IPDI-trimerized = the weight ratio 1:2), the above varnish (GDI/W-trimerized = the weight ratio 1:2) has the advantage of scratch resistance. The acid resistance and resistance to thermopolae are equally good values.

1. A mixture of blocked polyisocyanates, used as a hardener component varnishes hot drying, containing

a) a blocked polyisocyanate based on 1,6-diisocyanatohexane,

b) a blocked polyisocyanate based on cycloaliphatic diisocyanates selected from the group comprising 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane, bis(4-isocyanatophenyl)methane, 2,6-visitorinfo-norbornene, 2,5-visitorinfo-norbornene, 1,4-bis-isocyanatomethyl-cyclohexane and mixtures thereof, and

b) 3,5-dimethylpyrazol as the sole locking means mentioned under a) and b) polyisocyanates, characterized in that the blocked polyisocyanates taken in the weight balance of the situation:b)=1:1,8-2,2.



 

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9 cl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the chemistry of foamed polyurethanes, particularly a polyurethane system for making elastic articles, preferably for medical purposes, for example, orthopaedic articles, technical parameters of which have improved sanitary properties which meet their operating requirements. The present invention can also be used to make polyurethane bandages. The polyurethane system for making articles with improved sanitary properties contains compositions based on a polyol compound A, an isocyanate compound B and a mineral agent C, which is dispersed in polyol compound A. The isocyanate compound B used is prepolymers of methylene diphenyl diisocyanates MDI. The mineral agent C used is a mixture of bentonite nanopowders which are intercalated with silver ions Ag+ and cerium ions Ce3+.

EFFECT: improved sanitary properties of the obtained elastic articles, with regard to both inhibiting growth of microorganisms and reducing gas release of volatile toxic organic compounds.

9 cl, 2 dwg, 5 ex

Adhesive substances // 2466149

FIELD: chemistry.

SUBSTANCE: invention relates to aqueous compositions for gluing substrates, a method of obtaining such compositions, as well as a method of making latent-reactive coatings, films and powders from said compositions. The aqueous compositions for gluing substrates contain: polymers dispersed in water, having groups capable of reacting with isocyanate, such as urethane groups and urea groups; at least one dispersed solid aliphatic polyisocyanate which is not surface-active, with softening temperature higher than or equal to 40C; one or more compounds of group (subgroup) 5 and 6 elements, in which the oxidation state of said element is at least +4; and optionally other additives and auxiliary materials.

EFFECT: obtaining novel compositions for gluing substrates and latent-reactive coatings, films and powders based thereon, which are stable during storage and stable with respect to colour.

18 cl, 1 dwg, 6 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing self-curing polyurethane dispersions, use thereof as coating agents, coating agents containing these self-curing aqueous dispersions, a method of coating substrates, as well as substrates treated with coating agents. The method of producing self-curing aqueous polyurethane dispersions involves the following steps: I. reacting al) polyisocyanate with a mixture of, a2) 2,2-bis(hydroxymethyl)alkanecarboxylic acid as an anionic hydrophilisation agent containing a group which is reactive towards isocyanate and, a3) at least one polyol component with average OH-functionality >1, wherein any mixture from a2) and a3), or component a1) k) contains at least one catalyst selected from a group consisting of tertiary amines, tin, zinc or bismuth compounds; II obtaining an OH-functional polyurethane without NCO-groups from step I, which then; III. a4) is mixed with a reactive blocking agent for isocyanate groups, selected from a group consisting of butanone oxime, diisopropylamine or tert-butylbenzylamine, 3,5-dimethylpyrazole, triazole, respectively, mixture thereof; IV. subsequent reaction of that mixture from step III with a5) one or more polyisocyanates selected from group a1), wherein these polyisocyanates are the same as or are different from al), and subsequent V. obtaining a physical mixture of OH-functional polyurethane without NCO-groups and a blocked polyisocyanate from step IV, after which after either; VI. acid groups of OH-functional polyurethane a6) are completely or partially deprotonated by adding a neutralising agent; VII. and the polyurethane obtained at step VI id dispersed in water, or step VII is carried out before step VI.

EFFECT: obtaining self-curing aqueous polyurethane dispersions containing negligible amounts of cosolvent.

14 cl, 1 tbl, 5 ex

FIELD: printing.

SUBSTANCE: group of inventions relates to production of identification documents, made of thermoplastic material and a method of their manufacture. The identification document comprises the layers A), B) and C), at that the layer A) is thermoplastic, the layer B) is made of a storage-stable adhesive with latent reactivity, and the layer C) is thermoplastic, at that the adhesive comprises an aqueous dispersion comprising a diisocyanate or polyisocyanate with a melting point or, respectively, softening point above +30C and the polymer reactive towards isocyanates, which is polyurethane composed of crystallised polymer chains which, according to the study results, by thermomechanic method at temperatures below +110C decrystalise partially or completely.

EFFECT: exclusion of layers stratifying.

11 cl, 8 ex, 8 tbl

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