# US 2001/0041773 A1 · UV curable elastomer composition

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- Number: US 2001/0041773 A1
- Document ID: US20010041773A1
- Status: Published application
- Kind: A1
- Application number: 09/842,493
- Filed: 2001-04-26
- Published: 2001-11-15
- Earliest claimed: 1998-01-21
- Assignees: DuPont Dow Elastomers L.L.C.
- Inventors: Christian Ruepping
- Web page: https://patentgrep.com/patent/US20010041773A1

## CPC

- C08F 265/06: Polymerisation of acrylate or methacrylate esters on to polymers thereof
- C08F 255/02: on to polymers of olefins having two or three carbon atoms
- C08F 255/026: {on to ethylene-vinylester copolymers}
- C08F 259/08: on to polymers containing fluorine
- C08F 263/04: on to polymers of vinyl acetate
- C08F 265/04: on to polymers of esters
- C08F 279/02: on to polymers of conjugated dienes
- C08F 291/02: on to elastomers
- C08L 33/08: Homopolymers or copolymers of acrylic acid esters
- C09K 3/10: {Materials in mouldable or extrudable form} for sealing or packing joints or covers (filling pastes C09D5/34)
- C09K 2003/1068: {Crosslinkable materials}
- C09K 2200/0612: Butadiene-acrylonitrile rubber
- C09K 2200/062: Polyethylene
- C09K 2200/0625: Polyacrylic esters or derivatives thereof
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Ethylene copolymer elastomer compositions, acrylate rubber compositions, nitrile rubber compositions, fluoroelastomer compositions, and chlorinated elastomer compositions are provided which are curable by exposure to UV radiation. The compositions are particularly suited for production of elastomeric seals using hot melt equipment and a gasketing in place technique.

## Claims

### Claim 1

A thermally stable, curable elastomer composition comprising
a) 75 to 95 weight percent of an elastomer selected from the group consisting of
1) copolymers comprising ethylene and a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic acid, C1-C8 alkyl esters of methacrylic acid, and vinyl esters of C2-C8 carboxylic acids;
2) alkyl acrylate polymers selected from the group consisting of homopolymers of C1-C10 alkyl acrylates and copolymers of C1-C10 alkyl acrylates with up to 40 weight percent monovinyl monomers; and
3) diene copolymers selected from the group consisting of copolymers of a diene and an unsaturated nitrile and hydrogenated copolymers of a diene and an unsaturated nitrile;
b) 2 to 24 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional methiacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and multifunctional isocyanurate crosslinking agents; and
c) 0.2 to 5.0 weight percent of a UV initiator wherein the weight percentages of each of components a), b), and c) are based on the combined weight of components a), b), and c).

### Claim 2 (depends on 1)

The composition of claim 1 wherein the elastomer is a copolymer comprising ethylene and a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic acid and vinyl esters of C2-C8 carboxylic acids.

### Claim 3 (depends on 2)

The composition of claim 2 wherein the clastomer is a copolymer of ethylene and a C1-C8 alkyl ester of acrylic acid.

### Claim 4 (depends on 3)

The composition of claim 3 wherein the elastomer is a copolymer of ethylene and methyl acrylate.

### Claim 5 (depends on 2)

The composition of claim 2 wherein the elastomer is a copolymer of ethylene and a vinyl ester of a C2-C8 carboxylic acid.

### Claim 6 (depends on 5)

The composition of claim 5 wherein the elastomer is ethylene vinyl acetate.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the elastomer is a copolymer comprising
a) ethylene;
b) a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic acid, C1-C8 alkyl esters of methacrylic acid, and vinyl esters of C2-C8 carboxylic acids; and
c) a comonomer selected from the group consisting of carboxylic acids of 3-12 carbon atoms selected from the group consisting of alpha, beta-unsaturated monocarboxylic acids, alpha, beta-unsaturated dicarboxylic acids, and monoesters of alpha, beta-unsaturated dicarboxylic acids.

### Claim 8 (depends on 7)

The composition of claim 7 wherein the comonomer of b) is selected from the group consisting of C1-C8 alkyl esters of acrylic acid, and vinyl esters of C2-C8 carboxylic acids.

### Claim 9 (depends on 7)

The composition of claim 7 wherein component c) is a monoester of an alpha, beta-unsaturated dicarboxylic acid.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the elastomer is a homopolymer of a C1-C10 alkyl acrylate.

### Claim 11 (depends on 1)

The composition of claim 1 wherein the elastomer is a copolymer of a C1-C10 alkyl acrylate with up to 40 weight percent monovinyl monomer.

### Claim 12 (depends on 1)

The composition of claim 1 wherein the elastomer is a copolymer of a diene and an unsaturated nitrile.

### Claim 13 (depends on 1)

The composition of claim 1 wherein the multifunctional crosslinking agent is a multifunctional acrylate.

### Claim 14 (depends on 1)

The composition of claim 1 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 15 (depends on 1)

The composition of claim 1 wherein the UV initiator is a ketone.

### Claim 16

A process for applying a seal to an article comprising the steps of
A) blending at a temperature of between 25° C. and 250° C.:
1) 75 to 95 weight percent of an elastomer selected from the group consisting of
a) copolymers comprising ethylene and a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic to acid, C1-C8 alkyl esters of methacrylic acid, and vinyl esters of C2-C8 carboxylic acids;
b) alkyi acrylate polymers selected from the group consisting of homopolyrners of C1-C10 alkyl acrylates and copolymers of C1-C10 alkyl acrylates with up to 40 weight percent monovinyl monomers; and
c) diene copolymers selected from the group consisting of copolymers of a diene and an unsaturated nitrile and hydrogenated copolymers of a diene and an unsaturated nitrile;
2) 2 to 24 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional inethacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and multifunctional isocyanurate crossliinkinig agents; and
3) 0.2 to 5.0 weight percent of a UV initiator
wherein the weight percentages of each of components 1), 2), and 3) are based on the combined weight of components 1), 2), and 3), to form a thermally stable, curable, extrudable mixture;
B) depositing said extrudable mixture on said article in the shape and thickness desired to form an uncured seal; and
C) irradiating said uncured seal with UV radiation for a time sufficient to cure said seal.

### Claim 17 (depends on 16)

The process of claim 16 wherein the curable composition is heated to a temperature of 90°-170° C. in step A).

### Claim 18 (depends on 16)

The process of claim 16 wherein the article is made of a thermoplastic material.

### Claim 19 (depends on 16)

The process of claim 16 wherein the elastomer is a copolymer comprising ethylene and a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic acid and vinyl esters of C2-C8 carboxylic acids.

### Claim 20 (depends on 19)

The process of claim 19 wherein the elastomer is a copolymer of ethylene and a C1-C8 alkyl ester of acrylic acid.

### Claim 21 (depends on 20)

The process of claim 20 wherein the elastomer is a copolymer of ethylene and methyl acrylate.

### Claim 22 (depends on 19)

The process of claim 19 wherein the elastomer is ethylene vinyl acetate.

### Claim 23 (depends on 16)

The process of claim 16 wherein the elastomer is a copolymer comprising
a) ethylene;
b) a comonomer selected from the group consisting of C1-C8 alkyl esters of acrylic acid, C1-C8 alkyl esters of methacrylic acid, and vinyl esters of C2-C8 carboxylic acids; and
c) a comonomer selected from the group consisting of carboxylic acids of 3-12 carbon atoms selected from the group consisting of alpha, beta-unsaturated inonocarboxylic acids, alpha, beta-unsaturated dicarboxylic acids and monoesters of alpha, beta-unsaturated dicarboxylic acids.

### Claim 24 (depends on 23)

The process of claim 23 wherein component c) is a monoester of an alpha, beta-unsaturated dicarboxylic acid.

### Claim 25 (depends on 16)

The process of claim 16 wherein the elastomer is a homopolymer of a C1-C10 alkyl acrylate.

### Claim 26 (depends on 16)

The process of claim 16 wherein the elastomer is a copolymer of a C1-C10 alkyl acrylate with up to 40 weight percent monovinyl monomer.

### Claim 27 (depends on 16)

The process of claim 16 wherein the elastomer is a copolymer of a diene and an unsaturated nitrile.

### Claim 28 (depends on 16)

The process of claim 16 wherein the multifunctional crosslinking agent is a multifunctional acrylate.

### Claim 29 (depends on 16)

The process of claim 16 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 30 (depends on 16)

A cured article produced by the process of claim 16.

### Claim 31 (depends on 1)

The composition of claim 1 additionally comprising a foaming agent.

### Claim 32 (depends on 1)

A curable elastomer composition of claim 1 wherein the elastomer has a Mooney viscosity of 1-20 ML 1+4 (100° C.).

### Claim 33

A therimally stable, curable elastomer composition comprising
A) 70 to 99 weight percent of a fluoroeiastomer having at least one cure site selected from the group consisting of 1) copolymerized brominated olefins, chlorinated olefins and iodinated olefins; 2) copolymerized brominated unsaturated ethers, chlorinated unsaturated ethers, and iodinated unsaturated ethers; 3) copolymerized non-conjugated dienes and trienes and 4) iodine atoms, bromine atoms and mixtures thereof that are present at terminal positions of the fluoroelastomer chain;
B) 0.5 to 20 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional methacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and m ultifun ctional isocyanurate crosslinking agents; and
C) 0.1 to I0 weight percent of a UV initiator
wherein the weight percentages of each of components A), B), and C) are based on the combined weight of components A), B), and C).

### Claim 34 (depends on 33)

The composition of claim 33 wherein the fluoroelastomer is a copolymer comprising copolymerized units of vinylidenie fluoride.

### Claim 35 (depends on 33)

The composition of claim 33 wherein the fluoroelastomer is a copolymer comprising copolymerized units of tetrafluoroethylene.

### Claim 36 (depends on 33)

The composition of claim 33 wherein at least one cure site is selected from the group consisting of copolymerized brominated olefins, chlorinated olefins and iodinated olefins.

### Claim 37 (depends on 33)

The composition of claim 33 wherein at least one cure site is selected from the group consisting of copolymerized brominated unsaturated ethers, chlorinated unsaturated ethers, and iodinated unsaturated ethers.

### Claim 38 (depends on 33)

The composition of claim 33 wherein at least one cure site is selected from the group consisting of copolymerized non-conjugated dienes.

### Claim 39 (depends on 33)

The composition of claim 33 wherein at least one cure site is selected from the group consisting of iodine atoms and bromine atoms and mixtures thereof that are present at terminal positions of the fluoroelastorner chain.

### Claim 40 (depends on 33)

The composition of claim 33 having a cure site that is a brominated olefin.

### Claim 41 (depends on 40)

The composition of claim 40 wherein the cure site is 4-bromo-3,3,4,4-tetrafluorobutene-1.

### Claim 42 (depends on 33)

The composition of claim 33 wherein the multifunctional crosslinking agent is a multifunctional acryl ate.

### Claim 43 (depends on 33)

The composition of claim 33 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 44 (depends on 33)

The composition of claim 33 wherein the UV initiator is a ketone.

### Claim 45

A process for applying a seal to an article comprising the steps of
A) blending at a temperature of between 25° C. and 250° C.
1) 70 to 99 weight percent of a fluoroelastomer;
2) 0.5 to 20 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional metbacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and multifunctional isocyanurate crosslinking agents; and
3) 0.1 to 10 weight percent of a UV initiator
wherein the weight percentages of each of components 1), 2), and 3) are based on the combined weight of components 1), 2), and 3), to form a thermally stable, curable, extrudable mixture;
B) depositing said extrudable mixture on said article in the shape and thickness desired to form an uncured seal; and
C) irradiating said uncured seal with UV radiation for a time sufficient to cure said seal.

### Claim 46 (depends on 45)

The process of claim 45 wherein the curable composition is heated to a temperature of 90°-170° C. in step A).

### Claim 47 (depends on 45)

The process of claim 45 wherein the article is made of a thernoplastic material.

### Claim 48 (depends on 45)

The process of claim 45 wherein the fluoroelastomer is a copolymer comprising copolym-nerized units of vinylidene fluoride.

### Claim 49 (depends on 45)

The process of claim 45 wherein the fluoroelastomer is a copolymer comprising copolymerized units of tetrafluoroethylene.

### Claim 50 (depends on 45)

The process of claim 45 wherein the multifunctional crosslinking agent is a multifunctional acrylate.

### Claim 51 (depends on 45)

The process of claim 45 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 52 (depends on 45)

A cured article produced by the process of claim 45.

### Claim 53 (depends on 33)

The composition of claim 33 additionally comprising a foaming agent.

### Claim 54 (depends on 45)

The process of claim 45 wherein the fluoroelastomer has a Mooney viscosity of 10-90, ML 1+4 (121° C.).

### Claim 55

A thermally stable, curable elastomer composition consisting essentially of
A) 80 to 97 weight percent of a chlorinated elastomer selected from the group consisting of chlorinated polyolefin elastomers and epichlorohydrin elastomers;
B) 2 to 19.5 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional methacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and multifunctional isocyanurate crosslinking agents; and
C) 0.2 to 5.0 weight percent of a UV initiator
wherein the weight percentages of each of components A), B), and C) are based on the combined weight of components A), B), and C).

### Claim 56 (depends on 55)

The composition of claim 55 wherein the chlorinated elastomer is a chlorinated polyolefin elastomer.

### Claim 57 (depends on 56)

The composition of claim 56 wherein the chlorinated polyolefin elastomer is a chlorosulfonated polyolefin elastomer.

### Claim 58 (depends on 55)

The composition of claim 55 wherein the chlorinated elastomer is an epichlorohydrin elastomer.

### Claim 59 (depends on 55)

The composition of claim 55 wherein the multifunctional crosslinking agent is a multifunctional acrylate.

### Claim 60 (depends on 55)

The composition of claim 55 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 61 (depends on 55)

The comnposition of claim 55 wherein the UV initiator is a ketone.

### Claim 62

A process for applying a seal to an article comprising the steps of
A) blending at, a temperature of between 25° C. and 250° C.
1) 80 to 97 weight percent of a chlorinated elastomer selected from the group consisting of chlorinated polyolefin elastomers and epichlorohydrin elastomers;
2) 2 to 19.5 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents, multifunctional methacrylic crosslinking agents, multifunctional cyanurate crosslinking agents, and multifunctional isocyanurate crosslinking agents; and
3) 0.2 to 5.0 weight percent of a UV initiator
wherein the weight percentages of each of components 1), 2), and 3) are based on the combined weight of components 1), 2), and 3), to form a thermally stable, curable, extrudable mixture;
B) depositing said extrudable mixture on said article in the shape and thickness desired to form an uncured seal; and
C) irradiating said uncured seal with UV radiation for a time sufficient to cure said seal.

### Claim 63 (depends on 62)

The process of claim 62 wherein the curable composition is heated to a temperature of 90°-170° C. in step A).

### Claim 64 (depends on 62)

The process of claim 62 wherein the article is made of a thermoplastic material.

### Claim 65 (depends on 62)

The process of claim 62 wherein the chlorinated elastomer is a chlorinated polyolefin elastomer.

### Claim 66 (depends on 62)

The process of claim 62 wherein the chlorinated polyolefin elastomer is a chiorosulfonated polyolefini elastomer.

### Claim 67 (depends on 62)

The process of claim 62 wherein the chlorinated elastomer is an epichlorohydrin elastomer.

### Claim 68 (depends on 62)

The process of claim 62 wherein the multifunctional crosslinking agent is a multifunctional acrylate.

### Claim 69 (depends on 62)

The process of claim 62 wherein the multifunctional crosslinking agent is a multifunctional methacrylate.

### Claim 70 (depends on 62)

The process of claim 62 wherein the UV initiator is a ketone.

### Claim 71 (depends on 62)

A cured article produced by the process of claim 62.

### Claim 72 (depends on 55)

The composition of claim 55 additionally comprising a foaming agent.

### Claim 73 (depends on 62)

The process of claim 62 wherein the chlorinated elastomer has a Mooney viscosity of 10-90, ML 1+4 (121° C.).

### Claim 74

A process for applying a seal to an article comprising the steps of
A) blending at a temperature of between 25° C. and 250° C.
1) 80-98 weight percent of an ethylene alpha-olefin copolymer comprising ethylene and a C3-C20 alpha-olefin;
2) 1-19.5 weight percent of a multifunctional crosslinking agent selected from the group consisting of multifunctional acrylic crosslinking agents and multifunctional methacrylic crosslinlking agents; and
3) 0.2-5 weight percent of a UV initiator
wherein the weight percentages of each of components 1), 2), and 3) are based on the combined weight of components 1), 2), and 3), to form a thermally stable, curable, extrudable mixture;
B) depositing said extrudable mixture on said article in the shape and thickness desired to form an uncured seal; and
C) irradiating said uncured seal with UV radiation for a time sufficient to cure said seal.

### Claim 75 (depends on 74)

The process of claim 74 wherein the ethylene is an elastomeric copolymer of ethylene, a C3-C8 alpha-olefin and at least one non-conjugated diene.

### Claim 76 (depends on 74)

A cured article produced by the process of claim 74.