Curable liquid polymer compositions

Claim 2

A composition curable in the presence of a free radical generating agent comprising: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR12## and A is a polyvalent organic moiety, free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silicon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; and, Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 95 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4.

Claim 3

The composition of claim 1 including 0.0005 to about 50% by weight of the polyene/polythiol composition of a photocuring rate accelerator.

Claim 4

The composition of claim 1 wherein the polyene is a member of the group consisting of methylene bisacrylamide 1,3 butylene glycol diacrylate, 1,4 butylene glycol diacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, 1,6-hexane diol diacrylate, pentaerythritol tetraacrylate, bisphenol A dimethacrylate, N,N'-di(hydroxyethyl)dimethylhydantoin diacrylate, polyethylene glycol (200)diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, bisphenol A diacrylate, 1,3 butylene glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, triethylene glycol dimethacrylate, and trimethylol propane trimethacrylate, trimethylolpropane tricrotonate, and diethylene glycol dicinnamate.

Claim 5

The composition according to claim 1 wherein the polyene is the reaction product of an isocyanate terminated prepolymer or isocyanate monomer with a hydroxyalkyl ester of a member of the group consisting of acrylic acid, methacrylic acid, crotonic acid and cinnamic acid.

Claim 6

The composition according to claim 1 wherein the polyene is the reaction product of an oxirane terminated epoxy resin with a member of the group consisting of anhydride, acrylhalide amide and hydroxyalkyl ester of an acid member of the group consisting of acrylic, methacrylic, crotonic anc cinnamic.

Claim 7

A process of forming a solid cured polythioether which comprises 1. admixing a composition comprising: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR13## and A is a polyvalent organic moiety free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silicon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4, and

Claim 8

A process of forming a solid cured polythioether which comprises 1. admixing a composition comprising: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR13## and A is a polyvalent organic moiety free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silicon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4, and

Claim 9

exposing the mixture to a free radical generating agent.

Claim 10

exposing the mixture to a free radical generating agent.

Claim 11

The process according to claim 6 wherein the free radical generating agent is high energy radiation.

Claim 12

The process according to claim 6 wherein the free radical generating agent is a chemical free radical generating agent.

Claim 13

The process of claim 8 wherein the chemical free radical generating agent is selected from the group consisting of molecular oxygen; organic hydroperoxides and peroxides; blends of organic hydroperoxides and peroxides with tertiary amines; blends of organic hydroperoxies and peroxides with transition metal salts and blends of organic hydroperoxides and peroxides with tertiary amines and transition metal salts.

Claim 14

The process according to claim 6 wherein the composition includes 0.0005 to about 50% by weight of the polyene/polythiol composition of a photocuring rate accelerator.

Claim 15

The process according to claim 10 wherein the free radical generating agent is U. V. light.

Claim 16

The process according to claim 6 wherein the polyene is a member of the group consisting of methylene bisacrylamide 1,3 butylene glycol diacrylate, 1,4 butylene glycol diacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, 1,6-hexane diol diacrylate pentaerythritol tetraacrylate, bisphenol A dimethacrylate, N,N'-di(hydroxyethyl)dimethylhydantoin diacrylate, polyethylene glycol (200)diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, bisphenol A diacrylate, 1,3 butylene glycol dimethacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, triethylene glycol dimethacrylate, and trimethylol propane trimethacrylate, trimethylolpropane tricrotonate, and diethylene glycol dicinnamate.

Claim 17

The solid polythioether product prepared by the process of claim 6.

Claim 18

A sealant consisting essentially of the composition of claim 1.

Claim 19

An adhesive consisting essentially of the composition of claim 1.

Claim 20

The composition of claim 1 where X is acryloxy or methacryloxy.

Claim 21

The composition of claim 16 wherein X is acryloxy.

Claim 22

A composition capable of being crosslinked solely by radiation to form thioether groups between the carbon-to-carbon unsaturation of I and the thiol groups of II comprising: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR14## and A is a polyvalent organic moiety, free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silicon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; and, Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 95 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4.

Claim 23

A composition capable of being crosslinked solely by radiation to form thioether groups between the carbon-to-carbon unsaturation of I and the thiol groups of II comprising: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR14## and A is a polyvalent organic moiety, free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silicon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; and, Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 95 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4.

Claim 24

A process of forming a solid cured polythioether which consists essentially of 1. admixing a composition consisting essentially of: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR15## and A is a polyvalent organic moiety free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silocon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4, and

Claim 25

A process of forming a solid cured polythioether which consists essentially of 1. admixing a composition consisting essentially of: I. 98 to 2% by weight of the composition of a liquid polyene component of the formula [A--X).sub.m wherein m is an integer of at least 2, X is ##STR15## and A is a polyvalent organic moiety free of reactive carbon to carbon unsaturation and of highly water-sensitive members and consisting of atoms selected from the group consisting of carbon, hydrogen, oxygen, nitrogen, chlorine, bromine, fluorine, phosphorous and silocon; and R is a radical selected from the group consisting of hydrogen, phenyl and an alkyl containing 1 to 9 carbon atoms; Ii. 2 to 98% by weight of the composition of a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R.sub.8 --SH).sub.n wherein R 8 is a polyvalent organic moiety and n is at least 2, the reactive unsaturated carbon to carbon bonds per molecule in the polyene and the thiol groups per molecule in the polythiol being greater than 4, and

Claim 26

exposing the mixture to a free radical generating agent.

Claim 27

exposing the mixture to a free radical generating agent.