Adhesive compositions with double curing system

FIELD: chemistry.

SUBSTANCE: described is an adhesive composition for gluing to metal, containing: (a) at least one methacrylate radical polymerisation monomer; (b) an ambient temperature radical polymerisation initiator system containing at least one oxidant and at least one reducing agent; (c) a photoinitiator; and (d) an epoxy compound; where the adhesive will at least partially solidify at temperature between 10 and 40°C through a radical polymerisation catalyst system which is activated at ambient temperature. Described also is a two-component curing adhesive for gluing to metal, containing: (a) a first component containing (i) at least one methacrylate radical polymerisation monomer, (ii) at least one reducing agent and (iii) a photoinitiator and (b) a second component containing an oxidant which is reactive at ambient temperature with respect to the reducing agent and forms free radicals capable of initiating radical polymerisation and facilitate chain growth, and an epoxy compound; where the adhesive will at least partially solidify at temperature between 10 and 40°C through a radical polymerisation system activated at ambient temperature.

EFFECT: obtaining an adhesive which does not require additional heat for initiating curing.

24 cl, 6 ex

 

Cross-reference to related applications

This application has a priority based on provisional application for patent of the United States the number 60/820680, filed July 28, 2006 and entitled "Compositions adhesives with dual curing system," and provisional patent application in the United States the number 60/870143, filed December 15, 2006, entitled "Compositions adhesives with dual curing system".

The technical field to which the invention relates.

The present invention relates to adhesives containing system curing at ambient temperature and photoinitiator. The adhesive cures when activated curing system at ambient temperature and activation photoinitiator curing parts glue surface.

The level of technology

Acrylic structural adhesives activated by redox mechanism are well known articles of Commerce which are used commercially for fastening metal to metal and structural connections materials of two different substrates. Acrylic structural adhesives have found increasing application in the automotive industry, where adhesive bonding of metal parts replaces welding and mechanical fastening. However, these applications have exhibited unique requirements, to the E. it is not easy to do when using previously known adhesives. These requirements include high strength and superior nature of the destruction.

Cured by a redox mechanism, acrylic adhesives typically include a mixture of one or more olefinic reactive monomers such as methyl methacrylate or methacrylic acid, and curing agents and curing or polymerization proceed according to the mechanism of redox initiation at ambient temperature using the oxidant and reductant. Typical reducing agents are tertiary amines. Disubstituted aniline derivatives are disclosed in U.S. patent No. 4421879 (3,4-disubstituted aniline). U.S. patent No. 5932638 discloses n-halogen with 3,4-diamesinae and shows ways to overcome the fall of inhibition air.

U.S. patent No. 5641834 and U.S. patent No. 5710235, both introduced in the present document by reference, disclose a combination of blocked isocyanate groups polyalkalene with terminal olefinic groups. The composition also includes a monomer polymerizable by a radical mechanism, such as olefin monomer, and optionally a second polymer material. In a preferred embodiment of the invention the composition is an adhesive, which also includes fosforsoderzhashchie connection and oxidation will restore the local catalyst, active when the ambient temperature.

Additional distinctive features acrylic adhesives are surface stickiness and time to seizure. As used herein, "sticky surface" means the amount of glue on the exposed surface of the applied adhesive, which has not been cured. Such uncured adhesive can be transferred to other parts of the site or application equipment, leading to increased costs of cleaning. The General principle of surface stickiness is called "air inhibition", since atmospheric oxygen is a potent inhibitor of free-radical reactions. Accordingly, the number of surface tack can be measured by determining the thickness of any uncured adhesive on the surface.

In typical applications two-component reactive adhesive systems, two components are mixed together, the mixed material is applied to the first substrate for mounting, then perform the contact of the second substrate with the first substrate, on which is applied the glue. The time required for the mixing, application and implementation of contact, called herein "time to seizure".

In the prior art various approaches have been tried to overcome tackiness in the adhesive, which was PR is dmeta air inhibition. U.S. patent No. 6294249 offers farkle, which combined with bunching the material and then polymerized with the formation of the Packed composition, adhesive hot melt, which is then used for fastening. The adhesive comprises (a) from 50 to 100 parts by mass polymerization-capable component comprising at least one acrylic or methacrylic ester is not tertiary Olkiluoto alcohol in which the alkyl group contains from 1 to 20 (for example, from 3 to 18 carbon atoms); (b) from 0 to 50 parts by weight polymerization-capable component comprising at least one modifying monomer that is different from the named acrylic or methacrylic complex ether, copolymerizing with the component (a); sum (a) and (b) is to 100 parts by weight; (C) an effective amount of a polymerization initiator and (d) an effective amount of the agent of the transfer chain. The polymerization initiator preferably is photoinitiator or thermoregulatory initiator.

U.S. patent No. 5997682 relates to a method of obtaining a construction site, including the stage of receiving at least two products, each product has a surface; applying adhesive mixture with a dual system curing at least a portion of at least one of the surfaces; the connection of at least two products so that the button glutinous mixture was placed between at least two products; at least partially curing the first part of the adhesive mixture by irradiation of at least one of the products is the energy of the electron beam, so that a construction site, where at least two products are connected by the adhesive under the action of at least partially utverzhdenii the first part of the adhesive mixture, and the rest remain uncured under the action of the energy beam of electrons, and when the first part is cured, the remaining part of the adhesive mixture is cured thermally.

It would be desirable to create a glue that does not require any additional heat to initiate curing, especially when a team of construction produced from materials that deform under the influence of heat, such as the most rigid thermoplastics. It would be preferential to avoid the use of special reducing agents to solve air inhibition, while providing the rapid removal of surface tackiness in the adhesive, which is on display at the air.

Summary of the invention

Accordingly, the present invention is the creation of a glue comprising at least one monomer radical polymerization, radical initiating system at ambient temperature and photoinitiator. In one embodiment, implemented the I present invention acrylic adhesive further includes an adhesion promoter, the agent that increases the rigidity of the epoxide and the filling material.

In other embodiments, implementation of the present invention photoinitiator includes photoinitiator-based phosphine oxide, alpha-hydroxyketone or 2-hydroxy-2-methyl-1-phenyl-1-propanone.

In another embodiment of the present invention the monomer include olefin monomer, such as at least tetrahydrofurfurylamine, methacrylic acid and methyl methacrylate. In another embodiment of the present invention the monomer is contained in an amount of 20-70 percent by weight.

In one additional embodiment of the present invention, the reducing agent comprises a tertiary amine such as a compound of formula (I):

where each of the radicals R1and R2that may be the same or different, independently selected from the group including linear or branched, saturated or unsaturated With1-C10alkyl and linear or branched, saturated or unsaturated With1-C10hydroxyalkyl (i.e. alkyl substituted by a group-HE);

each of the radicals R3and R4independently selected from the group comprising a hydrogen atom and linear or branched, saturated or unsaturated With1-C10alkyl; and

X represents an atom of Galaga the A.

In alternative embodiments, the implementation of the present invention the reducing agent is selected from such compounds as N,N-diisopropanol-p-Chloroaniline; N,N-diisopropanol-p-bromaniline; N,N-diisopropanol-p-bromo-m-methylaniline; N,N-dimethyl-p-Chloroaniline; N,N-dimethyl-p-bromaniline; N,N-diethyl-p-Chloroaniline and N,N-diethyl-p-bromaniline.

In one embodiment of the present invention, the oxidizing agent includes an organic peroxide. In another embodiment of the present invention, the composition further includes an adhesion promoter, such as phosphorus-containing adhesion promoter, the adhesion promoter comprises from 0.01 to 20 mass% per the total weight of the basic component.

In another embodiment of the present invention, the composition further includes an agent rigidity, such as a liquid elastomer with olefinic terminal fragments derived from polyalkenes with terminal hydroxyl groups. In another embodiment of the present invention, the agent stiffness includes a block copolymer of the type a-b-A, where a unit selected from styrene, ring alkylated in the ring of styrene or mixtures thereof, and the block is an elastomeric segment having a low Tgselected from a conjugated diene or ethylene-propylene.

In another variant implementation of the ia of the present invention, the agent stiffness is contained in an amount of about 1 to 10 mass percent, in another embodiment of the invention the composition includes an auxiliary agent stiffness contained in an amount of from about 1 to about 15 weight percent calculated on the total weight of the basic component.

In the second aspect of the present invention it relates to two-component reaction glue, comprising a first component containing at least one monomer for radical polymerization, at least one reducing agent and photoinitiator; and a second component containing an oxidizing agent which is the reaction at ambient temperature relative to the reducing agent and forms free radicals that can initiate radical polymerization and to ensure the growth of chains.

In one embodiment of the present invention a two-component reaction adhesive further includes an auxiliary high-molecular agent stiffness with Mwgreater than approximately 18000 or Mngreater than about 10,000. In another embodiment, the present invention two-component reactive adhesive further comprises from 0.1 to 20 mass%, and containing phosphorus compounds having one or more olefinic groups.

In the third aspect of the present invention relates to a method for connecting substrates to receive the related node, including

a) contacting the substrate with an adhesive comprising the polymerization-capable component, radical catalytic system at ambient temperature and photoinitiator;

b) connection of substrates compression substrates together up until the excess glue on the connection lines will not be exposed to air;

(C) curing the adhesive for the formation of a partial or full strength under the action of a radical catalyst system at ambient temperature; and

d) effects on exposed outdoors adhesive activating electromagnetic energy to cure the exposed part of the adhesive.

In the fourth aspect of the present invention relates to a method for connecting substrates with the formation of the node, including

a) applying the adhesive containing polymerization-capable component, the catalytic radical system at ambient temperature and photoinitiator, between the two substrates so that the adhesive is in contact with surfaces and at least partially fills the space between the substrates and at least was partially exposed to the air;

b) at least partially curing the adhesive under the action of a radical catalyst system at a temperature of the environment;

(C) the impact on the portion of the adhesive exposed on the air, enable the processes of electromagnetic energy curing the exposed adhesive portion under the action of photoinitiator.

In the fifth aspect of the present invention relates to a method for a node with a bent edge, which includes stages

(a) the location of the first panel near, but without contact, with the second panel so that the edge of the second panel was located on the edge of the first panel;

(b) applying adhesive containing polymerization-capable component, radical catalytic system at ambient temperature and photoinitiator, between the overlapping part of two panels;

(C) adding the non-overlapping part of the second panel over the edge of the first panel;

(d) application of pressure to the overlapping side panels so that the panels are moved toward each other to the point where they remain at a predetermined distance from each other and at least part of the adhesive remains in the gap between the first and second panels with a portion of the adhesive exposed in the atmosphere;

(e) the course of curing at ambient temperature; and

(f) curing the exposed part of the adhesive by exposing the exposed part of the adhesive electromagnetic energy.

In another embodiment, the present invention prior to exposure on the exposed part of the adhesive electromagnetic energy exposed surface of the adhesive is sticky and after exposure to the exposed part of the adhesive electromagn the things of the energy surface becomes non-sticky.

In another embodiment of the present invention, the adhesive is exposed to electromagnetic energy using a robotic arm, comprising a source of electromagnetic energy, and in another embodiment of the invention the adhesive is applied through the distributor head, attached to an adjustable robotic arm.

Detailed description of the invention

Curing at ambient temperature adhesives, which are known to undergo air-inhibition process according to a variant implementation of the present invention an effective amount of photoinitiator. It was unexpectedly found that the redox initiating system does not affect photoinitiator and the adhesive exposed on the air, quickly develops local solidification, with the exception of the surface. In addition, although the compositions described in the present document, classified as adhesives, they can additionally be used as coatings, sealants, etc.

As used herein, "main components" of the various embodiments of the present invention are at least one monomer radical polymerization, a radical polymerization initiator that is activated at the temperature of the environment, including oxidation and restore the positive system of initiation and photoinitiator. Optional components include traditional and conventional additives and modifiers, such as the adhesion promoter, a plasticizer, a pigment, filler, UV stabilizer, etc.

Accordingly, as used herein, the term "ambient temperature" refers to the temperature of the adhesive application or the operating temperature of the environment surrounding the bonding part. Although it will usually be in the range from 10°C to 40°C, and preferably between 17°C and 35°C, but there may be cases where the ambient temperature may reach 70°C or higher, for example, in a room or chamber that provides irradiation with activation of photoinitiator. Basically, the advantage of curing at ambient temperature adhesives is that they do not require curing cycle or other purposeful application of energy for curing of the adhesive. Except for the random energy sources, such as room heaters, lamps or heated spreading equipment, no targeted thermal energy is not required for curing of the adhesive.

The monomer

Preferred monomers for radical polymerization according to a variant implementation of the present invention include olefin monomers characterized by the presence of-C=C - group. Examples of latinovich monomers include esters of (meth)acrylic acid, such as methyl methacrylate, ethyl methacrylate, butylmethacrylate, methyl acrylate, butyl acrylate, cyclohexylacetate, hexylaniline, 2-ethyl hexyl acrylate, laurelcrest, acrylate, diethylene glycol dimethacrylate, dicyclopentadienyltitanium, cyclohexylmethyl, laurenmarie, glycidylmethacrylate and tetrahydrofurfurylamine, methacrylic acid, acrylic acid, substituted (meth)acrylic acid, such as taconova acid, Acrylonitrile, Methacrylonitrile, acrylamide and methacrylamide; styrene, substituted styrene, such as Winstrol, chloresterol, methylsterol and n-butalbiral; vinyl acetate; vinylidenechloride and BUTADIENES such as 2,3-dichloro-1,3-butadiene and 2-chloro-1,3-butadiene. Other olefinic monomers include complex maleate ester; compound fumaric esters and styrene compounds such as styrene, chloresterol, methylsterol, butalbiral and Winstrol.

In one embodiment of the present invention the monomer is contained in an amount of 10-90% by weight of the main components. In an additional embodiment of the present invention the monomer is contained in an amount of from 20 to 70 percent by weight of the main components. In another embodiment of the present invention the monomer is contained in an amount of from 30 to 60 percent by weight of the basic component.

OK slideline recovery initiation system

In one embodiment of the invention, the adhesive contains the reaction at ambient temperature redox initiator or catalyst system. The reaction at ambient temperature catalytic systems are well known redox dual system, and there is no need to consider them in detail in this document, but they include at least one oxidizer and at least one reducing agent which is the reaction at ambient temperature for the formation of free radicals effective to initiate polymerization by the connecting mechanism and curing of the adhesive. Suitable redox initiators include, but not limit the scope of the claims, a combination of persulfate initiators such reducing agents as sodium metabisulfite and sodium bisulfite; systems based on organic peroxides and tertiary amines (for example, benzoyl peroxide plus dimethylaniline); and systems based on organic peroxides and transition metals, such as cumene hydroperoxide plus cobalt naphthenate.

In one embodiment, the present invention can be used in essentially any known oxidizing agent. Examples of oxidizing agents including the Ute, without limiting the scope of the claims, organic peroxides, such as benzoyl peroxide and other diazepamonline, hydroperoxides, such as cumene hydroperoxide, complex madefire, such as β-butyl peroxybenzoate; hydroperoxides ketones such as methyl ethyl ketone hydroperoxide, organic salts of transition metals such as cobalt naphthenate; and compounds containing a movable chlorine atom, such as sulphonylchloride.

Examples of reducing agents include, without limiting the scope of the claims, sulfinate acids; azo compounds, such as DINITROL asuitable acid; alpha-aminosulfonyl, such as bis(trisulfonates)benzylamine; tertiary amines, such as diisopropanol-p-toluidine (DIIPT), dimethylaniline, n-halogenated derivatives of aniline and dimethyl-p-toluidine; and condensation products of aminoaldehyde, for example, condensation products of aliphatic aldehydes, such as Butyraldehyde with primary amines, such as aniline or butylamine. The preferred reducing agents are the n-halogenated aniline derivatives having the formula (I):

where each of the radicals R1and R2that may be the same or different, independently selected from the group including linear or branched, saturated or unsaturated With1-C10Alki and linear or branched, saturated or unsaturated With1-C10hydroxyalkyl (i.e. alkyl substituted by a group-IT); each of the radicals R3and R4independently selected from the group comprising a hydrogen atom and linear or branched, saturated or unsaturated With1-C10alkyl; and X represents a hydrogen atom.

In a preferred embodiment of the invention in formula (I) each of the radicals R1and R2independently selected from the group comprising From1-C4alkyl and C1-C4hydroxyalkyl, and more preferably each of the radicals R1and R2that are the same is a methyl or isopropanol; each of the radicals R3and R4represents a hydrogen atom; and X represents an atom of fluorine, chlorine, bromine or iodine, more preferably chlorine atom or bromine. Examples of reducing agents include, but are not limited volume of claims, N,N-diisopropanol-p-Chloroaniline; N,N-diisopropanol-p-bromaniline; N,N-diisopropanol-p-bromo-m-methylaniline; N,N-dimethyl-p-Chloroaniline; N,N-dimethyl-p-bromaniline; N,N-diethyl-p-Chloroaniline and N,N-diethyl-p-bromaniline.

Tertiary amines which are suitable reducing agents include those which have the formula

where Z represents methylene; Y is selected from the group including the volume of hydrogen, the hydroxy-group, amino group, With1-C8alkyl, preferably1-C4alkyl, and C1-C8alkoxy, preferably1-C4alkoxy, a represents 0 or 1; and b is 1 or 2. This tertiary amine is preferred to accelerate the curing of options exercise of glue containing unsaturated organophosphorus compounds discussed above. Particularly preferred tertiary amines in this context are N,N-dimethylaniline and N,N-dimethylaminomethylphenol. The use of the known accelerators and promoters with redox dual catalytic systems can be pre-emptive. For example, can be used dimethylaminomethylphenol or organic salts of transition metals, such as copper naphthenate or cobalt.

Preferably the oxidizing agent is contained in an amount in the range from about 0.5 to about 50 percent by weight of the polymerized adhesive composition, and the amount of reducing agent will be in the range from about 0.05 to about 10, preferably from about 0.1 to about 6 percent by weight of the polymerized adhesive composition.

Photoinitiator

Photosensitizers or photoinitiators can further increase the reactivity of the compounds with olefinic nen is sidenote. Usable photoinitiator used as photoinitiated activators radical curing systems known in this field. Suitable examples include acetophenone, such as benzyldimethylamine and 1-hydroxycyclohexane, substituted alpha-ketols, such as 2-methyl-2-hydroxypropiophenone, simple benzoic esters, such as simple methyl ester benzoic acid, simple isopropyl ester of benzoic acid, ethers, substituted benzoic acid, such as a simple methyl ether Arizona, aromatic sulphonylchloride, photoactive oximes, photoinitiator on the basis of thioxanthone, such as a mixture of 2-isopropyl and 4-isopropylthioxanthone, and phosphinoxide photoinitiator, such as 2,4,6-trimethylbenzenesulfonamide. In one preferred embodiment of the present invention the preferred photoinitiator include alpha-hydroxyketone initiators.

Examples of photoinitiators include 2-hydroxy-2-methyl-1-phenylpropane-1-it, 1-hydroxycyclohexyl, 2-benzyl-2-dimethylamino-1-(4-morpholinomethyl)butanone-1, 2,2-dimethoxy-1,2-diphenylethan-1-it, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-he mixtures thereof.

In one embodiment, the present invention photoinitiator is used in an amount of about 0.001 to about 10,Casta by weight per 100 parts of total monomer, preferably from about 0.01 to about 5.0 parts by weight per 100 parts of total monomer.

Photoinitiator chosen depending on a number of factors, including compatibility with other components of the adhesive composition and the desired wavelength of the activating radiation. In a preferred embodiment of the present invention photoinitiator choose to activating radiation include any wavelength from 4 to 1000 nanometers, including in the area of the near ultraviolet and the far or vacuum UV radiation, visible radiation and near infrared radiation. Even more preferred embodiment of the invention the activating radiation includes wavelengths from about 10 to about 400 nanometers; and in another preferred embodiment of the present invention from about 400 to about 700 nanometers. In an additional embodiment of the present invention the radiation is incoherent, pulsed ultraviolet radiation from the discharge excimer lamp with a dielectric barrier or radiation from a mercury lamp.

Agent stiffness

Optional can be used to increase the rigidity of the polymer in amounts of from about 0 to about 80 percent. More preferably 2-50% by weight of the basic com is onenew. Being an example, low-molecular-weight agent stiffness has a mass-average molecular mass (Mw) less than about 18000 or srednecenovogo molecular mass (Mn) less than about 10,000. Increasing the stiffness of the polymeric material may include or not to include a structure with the olefinic unsaturation which is capable of polymerization by itself or copolymerizate at least one of the monomers of the radical polymerization described above. The polymeric material can be, for example, various solid and liquid elastomeric polymer materials and, in particular, liquid elastomers with integral olefinic groups, as described in U.S. patent No. 4223115; 4452944; 4769419; 5641834 and 5710235; and olefinic urethane reaction products of a prepolymer with isocyanate functional groups and monomers with hydroxyl groups, as described in U.S. patent No. 4223115; 4452944; 4467071 and 4769419, all the essence of each of which is introduced herein by reference.

Examples of liquid elastomers with integral olefinic groups, disclosed in WO 97/39074 include homopolymers of butadiene, copolymers of butadiene and at least one monomer, copolymerizable with him, for example styrene, Acrylonitrile, Methacrylonitrile (for example, poly(butadiene(meth)Acrylonitrile or poly(butadiene(meth)acrilan is triliteral) and mixtures thereof; and modified elastomeric polymeric materials, such as butadiene homopolymers and copolymers, as noted above, modified by copolymerization with their number from about a trace to about 5 percent by weight, based on the weight of the elastic material at least one functional monomer (such as acrylic acid, methacrylic acid, maleic anhydride, fumaric acid, styrene and methyl methacrylate, to obtain, for example, homopolymers and/or copolymers of polybutadiene with methacrylate end fragments). The preferred increase the rigidity of the polymer is a liquid elastomer with terminal olefinic groups derived from polyalkene with hydroxyl end groups, as described in patent '834. Other examples of increasing the rigidity of the polymers are urethane-modified liquid elastomer with olefinic terminal fragments derived from alkadiene with terminal carboxylic acids, as described in patent '419.

Also suitable for use are such agents increase the rigidity as a-b-A block copolymer of styrene-isoprene-styrene. Typical configurations include linear triblock, radial, branched and pyramidal geometry. And the block is hard at working temperature, while the block is usually what is elastic at the operating temperature. Suitable copolymers include those in which the block a represents isoprene, α-methylsterols, tert-butalbiral and other ring alkylated styrene, and mixtures of some of all the above. To represent an elastomeric conjugated diene, i.e. isoprene, having a mass-average molecular weight of from about 5,000 to about 500000.

In an additional embodiment, the present invention uses additional agent stiffness in combination with the primary agent stiffness. Additional polymeric agent stiffness can be entered in the typical amount of preferably 1-15% by weight of the mass of the main component, and more preferably about 1-10 percent by weight of the weight of the main components. Examples of additional polymeric agent stiffness is a polymer having a Mw greater than about 18000, or Mn greater than about 10,000. Other agents stiffness used in the embodiment of the present invention include, for example, block copolymers and random copolymers, including but not limiting of the scope of claims of the invention, polyethylene, polypropylene, styrene-butadiene, polychloroprene, EPDM, chlorinated elastomer, butyl rubber, styrene/butadiene/Acrylonitrile e is ustomer and chlorosulphurized polyethylene.

Adhesion promoters

Additional variant of implementation of the present invention also includes an adhesion promoter. The adhesion promoter according to a variant implementation of the present invention includes any adhesion promoter, known to specialists in this field as used for enhancing adhesion of acrylic adhesives. Preferred adhesion promoters according to a variant implementation of the present invention are phosphorus-containing compounds that enhance the adhesion of metal and can be any derivative of phosphinic acid, phosphonic acid or phosphoric acid, containing at least one P-Oh group and at least one organic residue, characterized by the presence of olefinic groups, which is preferably located at the ends. List of phosphate compounds is found in U.S. patent No. 4223115.

Phosphorus-containing compounds having vinyl unsaturation are preferably those compounds which have the allylic unsaturation, of which preferred are complex monetary phosphinic, phosphonic and phosphoric acids containing one link with vinyl or allyl, especially vinyl, unsaturation. Examples of phosphorus-containing compounds include, without limiting the scope of the claims, phosphoric acid,2-methacryloyloxyethyl; bis-(2-methacryloyloxyethyl)phosphate; 2-acryloyloxyhexyloxy; bis-(2-acryloyloxy)phosphate; methyl(2-methacryloyloxyethyl)phosphate; utilitaruluiincorporat; methylacetoacetate; ethylacetoacetate; vinylphosphonic acid; cyclohexen-3-phosphonic acid; alpha-hydroxybutane-2 phosphonic acid; 1-hydroxy-1-phenylmethane-1,1-diphosphonic acid; 1-hydroxy-1-methyl-1-diphosphonic acid; 1-amino-1-phenyl-1,1-diphosphonic acid; 3-amino-1-hydroxypropan-1,1-diphosphonic acid, amino-Tris(methylenephosphonic acid); gamma-aminopropylphosphonic acid; gamma-glycidoxypropyl acid; an ester of phosphoric acid-mono-2-amino-ethyl; allylphosphonate acid; allylphosphonate acid; β-methacryloyloxyethyl acid; diarylphosphino acid; β-methacryloyloxyethyl)phosphinic acid and allylmercaptocysteine acid. The most preferred adhesion promoter is 2-hydroxyethylmethacrylate phosphate.

An additional group of phosphorus-containing compounds suitable for use as adhesion promoters, includes compounds having the formula:

where R5selected from the group including H, C1-C8preferably1-C4alkyl, and N2C=CH-; R5selected from the group comprising H, With1-C8preferably1-C4alkyl; a is selected from the group comprising-R7O - and (R8O)nwhere R7represents an aliphatic or cycloaliphatic1-C9preferably2-C6, alkylenes group; R8represents a C1-C7alkylen, preferably2-C4alkylenes group; n is an integer from 2 to 10 and m is 1 or 2, preferably 1.

Adhesion promoters may be present in the compositions variant implementation of the present invention in amounts from about 0.01 to about 20, preferably from about 2 to about 10 percent by weight, based on the total weight of the adhesive composition.

Epoxysilane

In an additional embodiment of the present invention, the composition optionally includes an epoxy component. In one embodiment, the present invention epoxy-curable component includes amoxilonline connection (liquid resin), which contains statistically more than one oxiranes rings in the molecule (polyepoxide). Preferred amoxilonline material contains two epoxy groups per molecule. Monofunctional epoxy compound may also be combined with polyepoxide component as modificato is and viscosity, which acts as the reaction diluent. Epoxy resins suitable for use in the present invention include simple polyglycidyl esters of polybasic alcohols and complex polyglycidyl esters of polycarboxylic acids. Complex polyglycidyl esters can be obtained by engagement of epichlohydrin, such as epichlorohydrin or epibromohydrin, with aliphatic or aromatic polycarboxylic acid, such as oxalic acid, succinic acid, glutaric acid, terephthalic acid, 2,6-natalijagolosova acid and diarizonae linoleic acid. Simple polyglycidyl ethers of aromatic polyols are preferred, and they are received by the reaction of epichlorohydrin with polyhydroxyphenols compound in the presence of a base. Suitable source polyhydroxyphenols include resorcinol, catechin, hydroquinone, bis(4-hydroxyphenyl)-2,2-propane, also known as bisphenol a, bis(4-hydroxyphenyl)-1,1-isobutane, 4,4-dihydroxybenzophenone, bis(4-hydroxyphenol)-1,1-ethane. Bis(2-hydroxyphenyl)methane and 1,5-hydroxynaphthalene and simple diglycidyl ether of bisphenol A.

In one embodiment of the present invention the epoxy component is from 2 mass% to 15 mass percent, preferably from 6 mass% to 13 mass p is Acento, calculated on the total weight of the adhesive composition.

Packing for the application

Although glue various embodiments of the present invention can have many packaging forms, one of which is a Multipack or two-component adhesive system, where one package or part contains a curable or reactive components and the reducing agent, and the second packing or part contains an oxidizer. Photoinitiator may be included in any package; however, in the preferred embodiment of the present invention photoinitiator included with the reducing agent. Two-component adhesive system may optionally include rheology modifiers, waxes, stabilizers, and fillers, as is well known in this field.

The two parts are mixed together at the point of use in order to initiate the curing reaction. After mixing the individual packages on one or both of the joined surfaces apply the mixed adhesive system and surface combine with each other. The second package may include activator mounting, which includes an oxidizing agent for the redox catalyst system, and optionally an epoxy compound, an adhesion promoter and fillers.

The activator includes mounting

(1) from about 0.5 to about 50 percent what about the weight calculated on the total weight of the activator mounting at least one oxidizing agent, which can act as an oxidant of the redox dual catalytic system; and

(2) from about 30 to about 99.5 percent by weight, based on the total weight of the activator mounting bracket diluent.

Bearing diluents which are suitable for use in actuators mounting, can be simple inert solvent or diluent such as methylene chloride or butylbenzylphthalate, including mixtures of such solvents or diluents. Carrying the diluent should contain not more than about 5.0 percent by weight of any substance which is reactive with respect to the oxidant at ambient temperature. Bearing diluent may be more complex mixture comprising at least one film-forming binder in addition to the inert solvent or diluent. Carrying the diluent may contain, in addition to the solvent or solvent and film-forming binders, additives such as external plasticizers, agents greater flexibility, dispersing agents and stabilizers, provided that none of these supplements are not affected in an unacceptable way on the stability of the activator composition.

An example of a two-component system includes

(1) a first package including

(a) 10-90, preferably 20-70 mass% olefin the first monomer, selected from the group consisting of (meth)acrylic acid; esters; amides or NITRILES of (meth)acrylic acid; a complex maleate ester; compound fumaric esters; conjugated dienes; basis of itaconic acid; styrene compounds and vinylidenechloride;

(b) 0.05 to 10, preferably 0.1 to 6 weight percent of at least one reducing agent which reacts with the oxidant to form free radicals capable of initiating the radical polymerization reaction and the growth of the circuits;

(C) from 0.001 to about 10.0 g, preferably from 0.01 to about 5.0 parts by weight per 100 parts of total monomer photoinitiator;

(d) 10-80, preferably 20-50 weight percent of the principal agent stiffness;

(e) optionally 1 to 15, preferably 1-10 mass% of auxiliary agent stiffness;

(f) optionally from 0.01 to 20, preferably 2 to 10 mass percent of phosphorus-containing compounds having one or more olefinic groups; and

(II) a second package containing

activator attachment containing the oxidant redox dual catalytic system at ambient temperature, the oxidizing agent is reactive at ambient temperature relative to the agent (b), when the first and second packing is mixed with the received shall eat free radicals, able to initiate radical polymerization and growth of the chains, the amount of oxidant is sufficient to interact with the agent (b),

when this mass% calculated on the total number of major components.

Application

The adhesive system can be used to join metallic surfaces such as steel, aluminum and copper, with a variety of substrates, including metal, plastics and other polymers, reinforced plastics, fiber, glass, ceramics, wood, etc. Distinguishing feature of a variant of implementation of the present invention lies in the fact that the proposed adhesive compositions can be used for fastening metal substrates such as steel, aluminum and copper, with a small pre-treatment of the metal surface before applying glue or without it. Accordingly, the adhesive system variant implementation of the present invention provide effective fastening at ambient temperature, so there is no need for application of heat or application of adhesive systems on substrates, or for curing.

Although the adhesives according to a variant implementation of the present invention are preferred for compounds of metal surfaces, the adhesive compositions of the present invention can be the ü applied as an adhesive, primer or coating on any surface or substrate capable of receiving the adhesive. The metals which are preferred for mounting adhesives of the present invention include zinc, copper, cadmium, iron, tin, aluminum, silver, chromium, alloys of these metals and metal coating or plating these metals, such as galvanized steel, including coated by immersion in a melt steel with a coating applied by the method of electrolytic galvanizing in the melt, and galvannealing steel.

The adhesive coating can be applied by kstewangel, rolling, spraying, spot application, spiderbeam or in other ways on a single substrate, but preferably on both of the substrate to the desired thickness, preferably not exceeding 60 mil. The substrates can be clamped to the stiffness in the curing process in those installations where it is possible to expect the relative movement of the two substrates. For example, for the connection of metal surfaces for attachment amount of the adhesive composition is applied on one side, preferably on both sides, and the surface is combined with the adhesive composition between them. The adhesive should have a thickness less than 60 mils for optimum results. The smoothness of the surfaces and their purity (for example, if g is of Asda and bolts) will determine the desired film thickness for optimal mounting. Two metal and is placed between the composition is maintained in contact up until the mentioned adhesive composition has hardened enough to connect the two surfaces.

As already discussed herein, the compositions of the adhesives of various embodiments of the present invention can be used in various applications. In the preferred application as adhesive coatings bent edge of polymeric material is applied on the cut off edge of the bent flange connection after the connection was closed (bent). The main task is to protect the connection from corrosion and to provide an attractive appearance throughout the site.

As discussed above, the adhesive is cured by radical polymerization mechanism, but the inhibition by oxygen of the chemical mechanism prevents proper curing of glue surface, leading to the formation of a thin, sticky, partially cured layer. Photoinitiator contained in the adhesive composition, provides the surface hardening (leading to the formation of perceiving the paint with a non-sticky surface) after exposure under the action of a specified quantity and type of electromagnetic radiation. Thus, the gluing stage requires application and stud and exposure under the action of radiation. Photoinitiation curing can be carried out simultaneously with curing at ambient temperature or after him. As will be clear to experts in the field, curing at ambient temperature will be initiated as soon as mixed two-part adhesive system, but due to the speed of curing may take several hours before the glue reaches the desired strength.

Application and photoinitiation surface curing of this adhesive can be done in different ways. The following are some non-limiting volume of claims examples.

In the first aspect of the adhesive according to the options of implementing the present invention, two components of the adhesive composition is pumped from the storage containers into the dosing device. The metering device may consist of gear pumps, meters positive displacement rods or any other method of ensuring the correct relationship volumetric flow rate at the output of the two components before entering the mixing head. The mixing may be carried out by combining the measured quantities of the components in a static mixer or a dynamic mixer. The resulting mixed material is then ekstragiruyut through the tip of the applicator on h is the terrain directly above the seam. It is desirable to have the mixing head near the point of application, as immediately after mixing the adhesive has a limited time to seizure; may require aeration of the mixed glue between the application, if the expenses are not high enough to prevent gelation of the adhesive in the mixing head.

In another embodiment of the present invention the applicator and/or mixing head can be mounted on the robot to provide (1) a smooth pattern of the adhesive, (2) a reproducible illustration, and (3) together with the control of the flow speed of the robot can dictate the size of the droplets of glue. Considered the robotic process can also be carried out manually, if aesthetic considerations and reproducible forms are not significant.

As soon as a drop of glue applied to the part or parts that are designed for bonding, the outer layer should be superficially overiden using a source of electromagnetic radiation. As and when the glue is applied, there are a number of methods of surface hardening the applied adhesive.

In the first explanatory embodiment of the present invention the part coated with the glue drop is moved to the closed space, which provides protection details outside of this space from the action of electromagnetic and the receipt. The item is then placed by the robot over, under, along, etc. block lamps. The exposure time depends on the amount of electromagnetic energy is focused on the adhesive drop when the part is located at a certain distance from the light source. In most cases, the exposure takes place in a few seconds. Depending on the power light lamp can Shine continuously or, if used microwave or other "instant" light sources, they can be included only when there is detail and only during the desired time display.

In another explanatory embodiment of the present invention the part coated with the glue drop is moved into a closed space, which provides protection for items outside of this space from the action of electromagnetic radiation. The robot with the end of the Executive element, provided with a source of electromagnetic radiation, carries a source of uncured drop of glue at the correct distance and speeds up the curing of the surface of a drop. The robot can be the same robot that caused the glue, but only using the other end of the Executive element.

In another explanatory embodiment of the present invention the entire work cell is protected and then the source of electromagnetic radiation may be the adapted directly for distribution nozzle, so that the adhesive surface undergoes curing as soon as he put on the item. Depending on the kinetics of curing of the adhesive during the curing process may be the optimal time for curing the surface of the glue.

The following examples are given only for explanation purposes and in no way are intended to limit the scope of the claims of the invention.

Example 1

Received the following Royal blend

Side a

Description of the source materialAmount (wt.%)
Monomer 1 Tetrahydrofurfurylamine33,79
The monomer 2 Methacrylic acid2,4
The initiator based on the tertiary amine1,4
PhotoinitiatorX% (see below)
The adhesion promoter3,0
The rheology modifierof 5.4
Stabilizer0,01
Elastomeric agent stiffness34,5
Filler16,3
Wax1,2
Only-100,0

Side

Epoxy50,7
The source of benzoyl peroxide (BPO)7,7
The rheology modifier1,0
Filler40,6
Only100,0

The adhesive was mixed in the ratio 4:1 by volume and distributed in the form of a flange (1/4” width x 1/8” thick x 3” long) on an aluminum substrate and passed through the installation of UV-curing at different energy levels. The samples were evaluated on the stickiness of the surface immediately after exposure to UV radiation and 24 hours after exposure. Content photoinitiator, the data in the following table is presented as a percentage of the adhesive after mixing of the two sides a and B.

td align="center"> 361
PhotoinitiatorContent PHI (wt.%) UV energy (MJ/cm2)Original stickinessStickiness in 24 hours
No (comparative)0723stickysticky
1012stickysticky
Photoinitiator And12,0701not stickynot sticky
424not stickynot sticky
357not stickynot sticky
329not stickynot sticky
301not stickynot sticky
1,0684not stickynot sticky
446not stickynot sticky
not stickynot sticky
303Slightly stickynot sticky
0,5732not stickynot sticky
437slightly stickynot sticky
358slightly sticky, curingnot sticky
310no curingslightly sticky

PhotoinitiatorContent PHI (wt.%)UV energy (MJ/cm2)Original stickinessStickiness in 24 hours
0,11545not stickynot sticky
1128slightly stickynot sticky
732SL is HCA sticky not sticky
647slightly stickynot sticky
424no curingslightly sticky
Photoinitiator In22,0668not stickynot sticky
518not stickynot sticky
401slightly stickynot sticky
339slightly stickynot sticky
290stickynot sticky
1,0667not stickynot sticky
499slightly stickynot sticky
407stickynot sticky
0,5/td> 1529not stickysticky
1418not stickysticky
1041slightly stickyslightly sticky
676slightly stickyslightly sticky
0,12140slightly stickysticky
1572slightly stickyslightly sticky
1450slightly stickyslightly sticky
1047slightly stickyslightly sticky
685stickynot sticky
1 - Photoinitiator And includes a mixture of 50/50 wt.% 1-hydroxycyclohexanone and benzophenone
2 - Photoinitiator includes 2-hydroxy-2-methyl-1-phenylpropane

Note the R 2

A shoulder on the above masterbatches with 1 percent of photoinitiator In, added to the side And put on the substrate and utverjdali for 24 hours at ambient temperature. Cured adhesive, which had a thin film neuverennogo glue on the surface, exposed to UV light with a capacity of 600 MJ/cm2. The surface was assessed as non-sticky. Then the sample was stained. After complete curing inks were tested for adhesion, cross-hatch according to the standard ASDTM F 1842-02, and the adhesion was excellent.

Example 3

The following photoinitiator was added at 2 and 4 mass% in the above-mentioned Royal mix on the a side and thoroughly mixed.

1. No photoinitiator.

2. Photoinitiator With (a mixture of 2-isopropyl and 4-isopropylthioxanthone).

3. Photoinitiator D (2,4,6-trimethylbenzenesulfonamide).

Each of these materials were mixed in the ratio 4:1 by volume with the above fallopian mix hand In and distributed in the form of a flange with a width of 0.25” and left to cure at ambient temperature for 60 minutes. After curing, the surfaces of all samples were sticky. All samples then were exposed to UV light with intensity of the last 2000 MJ/cm2. The surface of both samples No. 2 and No. 3 were non-sticky, whereas poverhnostbyu No. 1 remained sticky.

Example 4

Preparing the following composition, including alternative redox system of initiation.

Description raw materialsNumber
Liquid elastomer GMA/CTB100 g
The methyl methacrylate88 g
Methacrylic acid10 g
Cumene hydroperoxide1 part per hundred (based on the whole solution)
p-toluensulfonate30 mmol/100 g of elastomer

To this composition was added photoinitiator E (a mixture of 50/50 weight percent diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide and 2-hydroxy-2-methyl-1-phenylpropane) in an amount of about 0.2 to 4 weight percent. These blends are combined on a side, containing the condensation product of Butyraldehyde and aniline in the ratio 10:1 by weight and left to cure at ambient temperature for 60 minutes. All samples had a very sticky surface after curing. All samples then were exposed to UV light with intensity of the last 2000 MJ/cm2. On the Ergneti both samples, containing photoinitiator E, were non-sticky, whereas the sample surface without photoinitiator remained sticky.

Example 5A

Was prepared following the fallopian mixture, mixed, and then applied and was utverjdali as in example 1. The following results are obtained.

Side a

Description raw materialsAmount (wt.%)
The monomer Tetrahydrofurfurylamine8,8
The initiator based on the tertiary amine1,6
Photoinitiator1,0
The adhesion promoter4,5
The rheology modifier4,0
Stabilizer0,01
Elastomeric agent stiffness61,2
Fillerrate 18.89
Only100,0

Side

Description of source materials/td> Amount (wt.%)
Epoxy48,0
Source bio11,0
The rheology modifier2,9
Elastomeric agent stiffness8,1
Filler30,0
Only100, 0

PhotoinitiatorContent PHI (wt.%)UV energy (MJ/cm2)Original stickinessStickiness in 24 hours
No (comparative)02000StickySticky
3000StickySticky
Photoinitiator And11,01008Slightly sticky Slightly sticky
1400Slightly stickySlightly sticky

PhotoinitiatorUV energy (MJ/cm2)Original stickinessStickiness in 24 hours
Content PHI (wt.%)1936Slightly stickyNon-sticky
2448Non-stickyNon-sticky
1,01000Slightly stickySlightly sticky
2000Slightly stickyNon-sticky
3000Non-stickyNon-sticky
0,51000Slightly stickySlightly sticky
Slightly stickyNon-sticky
3000Non-stickyNon-sticky
Photoinitiator With22,01000StickySticky
2000Slightly stickySlightly sticky
1,01000Slightly stickySlightly sticky
2000Non-stickyNon-sticky
1 - Photoinitiator And includes a mixture of 50/50 wt.% 1-hydroxycyclohexanone and benzophenone
2 - Photoinitiator includes a mixture of 50/50 wt.% diphenyl-2,4,6-trimethylbenzenesulfonamide and 2-hydroxy-2-methyl-1-phenylpropane-1-it

Example 5b

Was prepared following the fallopian mix with the wax component is added, mixed, applied, as in example 1.

Side a

Description of the source material the print materials Amount (wt.%)
The monomer Tetrahydrofurfurylamine8,8
The initiator based on the tertiary amine1,6
Photoinitiator1,0
The adhesion promoter4,5
The rheology modifier4,0
Stabilizer0,01
Elastomeric agent stiffness61,2
Filler14,89
Wax4,0
Only100,0

Side B

Description raw materialsAmount (wt.%)
Epoxy50,7
Source bio7,7
The rheology modifier 1,0
Filler40,6
Only100,0

The glue was utverjdali at 1000 and 2000 MJ/cm2. Glue containing wax and photoinitiator, had no source of stickiness and had no stickiness after 24 hours.

1. The adhesive composition for attaching to metal containing
(a) at least one methacrylate monomer radical polymerization;
(b) the system initiator of radical polymerization at ambient temperature, containing at least one oxidizing agent and at least one reducing agent;
(c) photoinitiator; and
(d) epoxy compound;
where the adhesive is at least partially harden at a temperature between 10 and 40°C through a system of radical polymerization catalyst that is activated when the ambient temperature.

2. The composition according to claim 1, where photoinitiator is phosphinoxide photoinitiation.

3. The composition according to claim 1, where photoinitiator is the alpha hydroxyketones.

4. The composition according to claim 1, where photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone.

5. The composition according to claim 1, where the monomer contains at least one of such monomers as tetrahydrofurfurylamine, methacrylic acid and methyl methacrylate.

6. The composition according to claim 1, where the monomer is contained in K is the number of 20-70 wt.% in the calculation of the total of components (a), (b) and (C).

7. The composition according to claim 1, where the reducing agent is a tertiary amine.

8. The composition according to claim 1, where the reducing agent has the formula (I)

where each of the radicals R1and R2that may be the same or different, independently selected from the group consisting of linear or branched, saturated or unsaturated C1-C10the alkyl and linear or branched, saturated or unsaturated C1-C10hydroxyalkyl (i.e., alkyl substituted by a group-HE);
each of the radicals R3and R4independently selected from the group consisting of a hydrogen atom and linear or branched, saturated or unsaturated C1-C10of alkyl; and
X represents a halogen atom.

9. The composition according to claim 1, where the reducing agent is selected from such compounds as N,N-diisopropanol-p-Chloroaniline; N,N-diisopropanol-p-bromaniline; N,N-diisopropanol-p-bromo-m-methylaniline; N,N-dimethyl-p-Chloroaniline; N,N-dimethyl-p-bromaniline; N,N-diethyl-p-Chloroaniline and N,N-diethyl-p-bromaniline.

10. The composition according to claim 1, where the oxidizing agent contains organic peroxide.

11. The composition according to claim 1, additionally containing an adhesion promoter.

12. The composition according to claim 11, where the adhesion promoter is a phosphorus-containing adhesion promoter.

13. The composition according to item 12, where the adhesion promoter sostav the et from 0.01 to 20 wt.% calculated on the total weight of the basic component.

14. The composition according to claim 1, additionally containing agent stiffness.

15. The composition according to 14, where the agent stiffness is liquid elastomer with olefinic terminal fragments derived from polyalkene with terminal hydroxyl groups.

16. The composition according to 14, where the agent rigidity contains the block copolymer of the type a-b-A, where a unit selected from styrene alkylated in the ring of styrene or mixtures thereof, and the block is an elastomeric conjugated diene, having a mass-average molecular weight of from about 5,000 to about 500000.

17. The composition according to 14, where the agent stiffness is contained in an amount of about 1 to 10 wt.%.

18. The composition according to 14, further containing an auxiliary agent stiffness contained in an amount of from about 1 to about 15 wt.% calculated on the total weight of the basic component.

19. Two-component curing adhesive for fastening to metal, containing
(a) a first component containing the
(i) at least one methacrylate monomer for radical polymerization,
(ii) at least one reducing agent and
(iii) photoinitiator and
(b) a second component containing an oxidizing agent which is the reaction at ambient temperature relative to the reducing agent and forms free radicals that in order to initiate radical polymerization and to ensure the growth of the chains, and epoxy compound;
where the adhesive is at least partially harden at a temperature between 10 and 40°C through a system of radical polymerization catalyst that is activated when the ambient temperature.

20. Two-component curing adhesive for fastening to metal in claim 19, where (a) further comprises an auxiliary high-molecular agent stiffness with Mwmore than about 18000 or Mnmore than about 10000.

21. Two-component curing adhesive for fastening to metal in claim 19, where (a) further comprises from 0.1 to 20 wt.% phosphorus-containing compounds having one or more olefinic groups.

22. The composition according to claim 2, where photoinitiator is 2,4,6-trimethylbenzenesulfonamide.

23. The composition according to claim 1, where the epoxy compound is polyepoxide.

24. The composition according to claim 1, where the epoxy compound is chosen from simple polyglycidyl ether of a polyhydric alcohol and a complex polyglycidyl ether polycarboxylic acid.



 

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