Hydroxyl-containing liquid polymers and pressure-sensitive adhesives and laminates prepared therefrom

Claim 2

A composition comprising (A) at least one alkyl acrylate liquid polymer containing polymerized therein from about 1 weight percent to about 20 weight percent N-vinyl-2-pyrrolidone and containing both terminal and random hydroxyl functionality, and (B) at least one prepolymer of a polyalkylene ether glycol or polyester glycol with an excess amount of an aromatic diisocyanate, wherein (1) said alkyl acrylate liquid polymer contains an average from about 1.4 to about 6 hydroxyl groups per molecule, and contains polymerized therein at least about 65 weight percent of at least one alkyl acrylate, the alkyl group of which contains from 3 to 10 carbon atoms, (2) said polyalkylene ether glycol contains from 3 to 6 carbon atoms per alkylene group and has a molecular weight from about 400 to about 2,000, (3) said aromatic diisocyanate contains from 8 to about 24 carbon atoms, (4) said prepolymer has a molecular weight from about 900 to about 3,000, and (5) the ratio of hydroxyl equivalents to free isocyanate equivalents is from about 0.7/1 to about 4.5/1.

Claim 3

A composition of claim 1 wherein said alkyl acrylate liquid polymer has a molecular weight from about 1,000 to about 6,000, and said prepolymer contains from about 2 weight percent to about 10 weight percent excess isocyanate based upon prepolymer weight.

Claim 4

A composition of claim 1 wherein said alkyl acrylate liquid polymer contains copolymerized therein at least one other olefinically unsaturated monomer.

Claim 5

A composition of claim 3 wherein said olefinically unsaturated monomer is a vinylidene comonomer containing at least one terminal CH 2 ═C< group per molecule.

Claim 6

A composition of claim 4 wherein said vinylidene comonomer is selected from the group consisting of (a) dienes containing 4 to 10 carbon atoms, (b) vinyl nitriles having the formula ##STR6## wherein R 2 is hydrogen or an alkyl group containing 1 to 3 carbon atoms, (c) acrylates having the formula ##STR7## wherein R 3 is hydrogen or an alkyl radical containing 1 to 3 carbon atoms, and R 4 is hydrogen or an alkyl radical containing 1, 2 or 11 to 18 carbon atoms or an alkoxyalkyl, alkylthioalkyl, or cyanoalkyl radical containing 2 to 12 carbon atoms, or wherein R 3 is an alkyl radical containing 1 to 3 carbon atoms and R 4 is an alkyl radical containing 3 to 10 carbon atoms, (d) vinyl aromatics having the formula ##STR8## wherein R 5 is hydrogen, halogen or an alkyl radical containing 1 to 4 carbon atoms, (e) vinyl and allyl esters of carboxylic acids containing 2 to 8 carbon atoms, (f) vinyl and allyl ethers of alkyl radicals containing 1 to 8 carbon atoms, (g) monoolefins containing 2 to 14 carbon atoms, (h) vinyl halides, (i) divinyls and diacrylates, (j) amides of α,β-olefinically unsaturated carboxylic acids containing 2 to 8 carbon atoms, (k) hydroxyl-containing vinylidene monomers, and (l) diacetone acrylamide.

Claim 7

A composition of claim 5 wherein said vinylidene comonomer is selected from the group consisting of said dienes, vinyl nitriles, acrylates, hydroxyl-containing vinylidene monomers and diacetone acrylamide.

Claim 8

A composition of claim 6 wherein said vinylidene comonomer is selected from the group consisting of butadiene, acrylonitrile, ethyl acrylate, propyl acrylate, a hydroxyl-containing ester of acrylic acid, and diacetone acrylamide.

Claim 9

A composition of claim 7 wherein component B is a prepolymer of polytetramethylene ether glycol with toluene diisocyanate, or a prepolymer of polypropylene ether glycol with toluene diisocyanate.

Claim 10

A composition of claim 8 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, butadiene, and a hydroxyl-containing ester of acrylic acid.

Claim 11

A composition of claim 9 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 12

A composition of claim 8 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, butadiene, acrylonitrile, and a hydroxyl-containing ester of acrylic acid.

Claim 13

A composition of claim 11 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 14

A composition of claim 8 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, ethyl acrylate and a hydroxyl-containing ester of acrylic acid.

Claim 15

A composition of claim 13 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 16

A cured composition of claim 1.

Claim 17

A laminate structure having as adhesive a composition comprising (A) at least one alkyl acrylate liquid polymer containing polymerized therein from about 1 weight percent to about 20 weight percent N-vinyl-2-pyrrolidone and containing both terminal and random hydroxyl functionality, and (B) at least one prepolymer of a polyalkylene ether glycol or polyester glycol with an excess amount of an aromatic diisocyanate, wherein (1) said alkyl acrylate liquid polymer contains an average from about 1.4 to about 6 hydroxyl groups per molecule, and contains polymerized therein at least about 65 weight percent of at least one alkyl acrylate, the alkyl group of which contains from 3 to 10 carbon atoms, (2) said polyalkylene ether glycol contains from 3 to 6 carbon atoms per alkylene group and has a molecular weight from about 400 to about 2,000, (3) said aromatic diisocyanate contains from 8 to about 24 carbon atoms, (4) said prepolymer has a molecular weight from about 900 to about 3,000, and (5) the ratio of hydroxyl equivalents to free isocyanate equivalents is from about 0.7/1 to about 4.5/1.

Claim 18

A laminate structure having as adhesive a composition comprising (A) at least one alkyl acrylate liquid polymer containing polymerized therein from about 1 weight percent to about 20 weight percent N-vinyl-2-pyrrolidone and containing both terminal and random hydroxyl functionality, and (B) at least one prepolymer of a polyalkylene ether glycol or polyester glycol with an excess amount of an aromatic diisocyanate, wherein (1) said alkyl acrylate liquid polymer contains an average from about 1.4 to about 6 hydroxyl groups per molecule, and contains polymerized therein at least about 65 weight percent of at least one alkyl acrylate, the alkyl group of which contains from 3 to 10 carbon atoms, (2) said polyalkylene ether glycol contains from 3 to 6 carbon atoms per alkylene group and has a molecular weight from about 400 to about 2,000, (3) said aromatic diisocyanate contains from 8 to about 24 carbon atoms, (4) said prepolymer has a molecular weight from about 900 to about 3,000, and (5) the ratio of hydroxyl equivalents to free isocyanate equivalents is from about 0.7/1 to about 4.5/1.

Claim 19

A laminate structure of claim 16 wherein said alkyl acrylate liquid polymer has a molecular weight from about 1,000 to about 6,000, and said prepolymer contains from about 2 weight percent to about 10 weight percent excess isocyanate based upon prepolymer weight.

Claim 20

A laminate structure of claim 16 wherein said alkyl acrylate liquid polymer contains copolymerized therein at least one other olefinically unsaturated monomer.

Claim 21

A laminate structure of claim 18 wherein said olefinically unsaturated monomer is a vinylidene comonomer containing at least one terminal CH 2 ═C< group per molecule.

Claim 22

A laminate structure of claim 19 wherein said vinylidene comonomer is selected from the group consisting of (a) dienes containing 4 to 10 carbon atoms, (b) vinyl nitriles having the formula ##STR9## wherein R 2 is hydrogen or an alkyl group containing 1 to 3 carbon atoms, (c) acrylates having the formula ##STR10## wherein R 3 is hydrogen or an alkyl radical containing 1 to 3 carbon atoms, and R 4 is hydrogen or an alkyl radical containing 1, 2 or 11 to 18 carbon atoms or an alkoxyalkyl, alkylthioalkyl, or cyanoalkyl radical containing 2 to 12 carbon atoms, or wherein R 3 is an alkyl radical containing 1 to 3 carbon atoms and R 4 is an alkyl radical containing 3 to 10 carbon atoms, (d) vinyl aromatics having the formula ##STR11## wherein R 5 is hydrogen, halogen or an alkyl radical containing 1 to 4 carbon atoms, (e) vinyl and allyl esters of carboxylic acids containing 2 to 8 carbon atoms, (f) vinyl and allyl ethers of alkyl radicals containing 1 to 8 carbon atoms, (g) monoolefins containing 2 to 14 carbon atoms, (h) vinyl halides, (i) divinyls and diacrylates, (j) amides of α,β-olefinically unsaturated carboxylic acids containing 2 to 8 carbon atoms, (k) hydroxyl-containing vinylidene monomers, and (l) diacetone acrylamide.

Claim 23

A laminate structure of claim 20 wherein said vinylidene comonomer is selected from the group consisting of said dienes, vinyl nitriles, acrylates, hydroxyl-containing vinylidene monomers and diacetone acrylamide.

Claim 24

A laminate structure of claim 21 wherein said vinylidene comonomer is selected from the group consisting of butadiene, acrylonitrile, ethyl acrylate, propyl acrylate, a hydroxyl-containing ester of acrylic acid, and diacetone acrylamide.

Claim 25

A laminate structure of claim 22 wherein component B is a prepolymer of polytetramethylene ether glycol with toluene diisocyanate, or a prepolymer of polypropylene ether glycol with toluene diisocyanate.

Claim 26

A laminate structure of claim 23 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, butadiene, and a hydroxyl-containing ester of acrylic acid.

Claim 27

A laminate structure of claim 24 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 28

A laminate structure of claim 23 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, butadiene, acrylonitrile, and a hydroxyl-containing ester of acrylic acid.

Claim 29

A laminate structure of claim 26 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 30

A laminate structure of claim 23 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, ethyl acrylate and a hydroxyl-containing ester of acrylic acid.

Claim 31

A laminate structure of claim 28 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 32

A cured laminate structure of claim 16.

Claim 33

A process comprising mixing and curing a composition comprising (A) at least one alkyl acrylate liquid polymer containing polymerized therein from about 1 weight percent to about 20 weight percent N-vinyl-2-pyrrolidone and containing both terminal and random hydroxyl functionality, and (B) at least one prepolymer of a polyalkylene ether glycol or polyester glycol with an excess amount of an aromatic diisocyanate, wherein (1) said alkyl acrylate liquid polymer contains an average from about 1.4 to about 6 hydroxyl groups per molecule, and contains polymerized therein at least about 65 weight percent of at least one alkyl acrylate, the alkyl group of which contains from 3 to 10 carbon atoms, (2) said polyalkylene ether glycol contains from 3 to 6 carbon atoms per alkylene group and has a molecular weight from about 400 to about 2,000, (3) said aromatic diisocyanate contains from 8 to about 24 carbon atoms, (4) said prepolymer has a molecular weight from about 900 to about 3,000, and (5) the ratio of hydroxyl equivalents to free isocyanate equivalents is from about 0.7/1 to about 4.5/l.

Claim 34

A process comprising mixing and curing a composition comprising (A) at least one alkyl acrylate liquid polymer containing polymerized therein from about 1 weight percent to about 20 weight percent N-vinyl-2-pyrrolidone and containing both terminal and random hydroxyl functionality, and (B) at least one prepolymer of a polyalkylene ether glycol or polyester glycol with an excess amount of an aromatic diisocyanate, wherein (1) said alkyl acrylate liquid polymer contains an average from about 1.4 to about 6 hydroxyl groups per molecule, and contains polymerized therein at least about 65 weight percent of at least one alkyl acrylate, the alkyl group of which contains from 3 to 10 carbon atoms, (2) said polyalkylene ether glycol contains from 3 to 6 carbon atoms per alkylene group and has a molecular weight from about 400 to about 2,000, (3) said aromatic diisocyanate contains from 8 to about 24 carbon atoms, (4) said prepolymer has a molecular weight from about 900 to about 3,000, and (5) the ratio of hydroxyl equivalents to free isocyanate equivalents is from about 0.7/1 to about 4.5/l.

Claim 35

A composition of claim 8 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, and a hydroxyl-containing ester of acrylic acid.

Claim 36

A composition of claim 32 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

Claim 37

A laminate structure of claim 23 wherein the backbone of said alkyl acrylate liquid polymer (component A) contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone, and a hydroxyl-containing ester of acrylic acid.

Claim 38

A laminate structure of claim 34 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.