Patent US4117196A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4117196A Expired / Lapsed US ⏱️ 0.0 years remaining

Photocurable imidizable polyene-polythiol compositions

Assignee: WR Grace and Co Conn
•
Filing: 1977-09-02
•
Granted: 1978-09-26
•
Expires: 1997-09-02
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract This invention relates to polyenes containing at least two ethylenically unsaturated bonds per molecule formed by reacting in substantially stoichiometric amounts, (1) a primary diamine, (2) a member of the group consisting of a benzenoid-containing dianhydride, acid anhydride and anhydride acid halide and (3) an ethylenically unsaturated alcohol. The thus formed amide-acid polyene either per se or after being cured in combination with a polythiol in the presence of a free radical generator will, upon heating, imidize.

Inventors

  • 👤 Eckart Mathias

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:55
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/1025; C08G75/00; C08G75/02; C08G75/04; C08G75/045; C08G75/12; C09; C09D; C09D131/00; C09D131/02; C09D181/00; C09D181/02; Y; Y10; Y10S; Y10S525/00; Y10S525/925; Y10S525/928; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2933; Y10T428/294; Y10T428/31504; Y10T428/31533

Claims Analysis

Total Claims: 53
Claim 1
Independent Claim 96 words
An amide-acid polyene of the formula: ##STR26## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR27## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10.
Claim 2
Dependent Claim 96 words
An amide-acid polyene of the formula: ##STR26## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR27## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10.
Claim 3
Dependent Claim 101 words
An imide-containing polyene of the formula: ##STR28## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR29## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10.
Claim 4
Dependent Claim 101 words
An imide-containing polyene of the formula: ##STR28## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR29## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10.
Claim 5
Independent Claim 173 words
A method of preparing an amide-acid polyene which comprises reacting in an inert atmosphere under anhydrous conditions in substantially stoichiometric amounts (1) at least one primary diamine having the structural formula: H 2 N--R--NH 2 wherein R is a divalent organic moiety containing at least 2 carbon atoms, the two amino groups of said diamine each attached to separate carbon atoms of said divalent organic moiety with (2) at least one anhydride-containing member of the group consisting of ##STR30## wherein R' is an aromatic residue attached to at least 3 carboxyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue and X is a halide radical and (3) an ethylenically unsaturated alcohol of the formula: HO--A)(Y) m wherein A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR31## R" is hydrogen or methyl; and m and d are 1 to 10 at a temperature in the range 20° to 100° C. in an organic solvent for the amide-acid polyene product.
Claim 6
Independent Claim 173 words
A method of preparing an amide-acid polyene which comprises reacting in an inert atmosphere under anhydrous conditions in substantially stoichiometric amounts (1) at least one primary diamine having the structural formula: H 2 N--R--NH 2 wherein R is a divalent organic moiety containing at least 2 carbon atoms, the two amino groups of said diamine each attached to separate carbon atoms of said divalent organic moiety with (2) at least one anhydride-containing member of the group consisting of ##STR30## wherein R' is an aromatic residue attached to at least 3 carboxyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue and X is a halide radical and (3) an ethylenically unsaturated alcohol of the formula: HO--A)(Y) m wherein A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR31## R" is hydrogen or methyl; and m and d are 1 to 10 at a temperature in the range 20° to 100° C. in an organic solvent for the amide-acid polyene product.
Claim 7
Dependent Claim 39 words
The method according to claim 3 wherein the anhydride-containing member is an anhydride acid halide and the halide formed from reacting the anhydride acid halide with the ethylenically unsaturated alcohol is removed prior to reaction with the primary diamine.
Claim 8
Dependent Claim 30 words
The process of imidizing the amide-acid polyene of claim 1 which comprises heating said polyene at a temperature in the range 50°-250° C. for a time sufficient to cause imidization.
Claim 9
Dependent Claim 28 words
The process according to claim 7 wherein the imidization is carried out in an inert solvent for the amide-acid polyene at a temperature in the range 50°-150° C.
Claim 10
Dependent Claim 167 words
A photocurable composition comprising (A) an amide-acid containing polyene of the formula: ##STR32## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR33## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator.
Claim 11
Dependent Claim 167 words
A photocurable composition comprising (A) an amide-acid containing polyene of the formula: ##STR32## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR33## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator.
Claim 12
Dependent Claim 171 words
A photocurable composition comprising (A) an imide-containing polyene of the formula: ##STR34## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR35## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator.
Claim 13
Dependent Claim 171 words
A photocurable composition comprising (A) an imide-containing polyene of the formula: ##STR34## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR35## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator.
Claim 14
Dependent Claim 182 words
The process of forming a solid cured amide-acid containing polythioether which comprises admixing (A) a polyene of the formula: ##STR36## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR37## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator and, thereafter, exposing the mixture to actinic radiation.
Claim 15
Dependent Claim 182 words
The process of forming a solid cured amide-acid containing polythioether which comprises admixing (A) a polyene of the formula: ##STR36## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR37## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator and, thereafter, exposing the mixture to actinic radiation.
Claim 16
Dependent Claim 210 words
The process of forming a solid cured imide containing polythioether which comprises (1) admixing (A) a polyene of the formula: ##STR38## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR39## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, then in either order (2) exposing said admixture to actinic radiation and (3) heating the admixture at a temperature in the range 50°-250° C. for a time sufficient to imidize the amide-acid in the polyene.
Claim 17
Dependent Claim 210 words
The process of forming a solid cured imide containing polythioether which comprises (1) admixing (A) a polyene of the formula: ##STR38## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR39## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, then in either order (2) exposing said admixture to actinic radiation and (3) heating the admixture at a temperature in the range 50°-250° C. for a time sufficient to imidize the amide-acid in the polyene.
Claim 18
Dependent Claim 253 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR40## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR41## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) 0.01-5% by weight of (A) and (B) of a pinacol of the general formula: ##STR42## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy and, thereafter, heating the admixture in the range 50°-250° C.
Claim 19
Dependent Claim 253 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR40## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR41## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) 0.01-5% by weight of (A) and (B) of a pinacol of the general formula: ##STR42## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy and, thereafter, heating the admixture in the range 50°-250° C.
Claim 20
Dependent Claim 189 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) an imide containing polyene of the formula: ##STR43## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR44## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, and, thereafter, exposing the mixture to actinic radiation.
Claim 21
Dependent Claim 189 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) an imide containing polyene of the formula: ##STR43## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR44## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, and, thereafter, exposing the mixture to actinic radiation.
Claim 22
Dependent Claim 258 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR45## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR46## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) 0.01-5% by weight of (A) and (B) of the pinacol of the general formula: ##STR47## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy and, thereafter, heating the admixture in the range 50°-250° C.
Claim 23
Dependent Claim 258 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR45## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR46## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) 0.01-5% by weight of (A) and (B) of the pinacol of the general formula: ##STR47## wherein R 1 and R 3 are members independently selected from the group consisting of substituted and unsubstituted aromatic radicals, R 2 and R 4 are members independently selected from the group consisting of substituted and unsubstituted aliphatic and aromatic radicals and X and Y are members independently selected from the group consisting of hydroxyl, alkoxy and aryloxy and, thereafter, heating the admixture in the range 50°-250° C.
Claim 24
Dependent Claim 112 words
A photopolymerizable composition comprising (A) an imide-containing polyene of the formula: ##STR48## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR49## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10; and (B) a photocuring rate accelerator.
Claim 25
Dependent Claim 112 words
A photopolymerizable composition comprising (A) an imide-containing polyene of the formula: ##STR48## wherein → denotes isomerism, R is a divalent organic moiety remaining after a secondary diamide has reacted with adjacent carboxylic acid groups to form imide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR49## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10; and (B) a photocuring rate accelerator.
Claim 26
Dependent Claim 14 words
An article comprising the composition of claim 7 as a coating on a substrate.
Claim 27
Dependent Claim 13 words
The article according to claim 15 wherein the substrate is an electrical conductor.
Claim 28
Dependent Claim 14 words
An article comprising the composition of claim 8 as a coating on a substrate.
Claim 29
Dependent Claim 12 words
The article of claim 17 wherein the substrate is an electrical conductor.
Claim 30
Dependent Claim 217 words
The process of coating a substrate which comprises (1) applying to a substrate a curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR50## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR51## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, then in either order (2) exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate and (3) heating said cured composition in the range 50°-250° C. to imidize the polyene.
Claim 31
Dependent Claim 217 words
The process of coating a substrate which comprises (1) applying to a substrate a curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR50## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR51## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, then in either order (2) exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate and (3) heating said cured composition in the range 50°-250° C. to imidize the polyene.
Claim 32
Dependent Claim 38 words
The process according to claim 19 wherein the curable composition contains 0.005 to 50% by weight of the polyene and polythiol of said curable composition of a photocuring rate accelerator and the free radical generator is actinic radiation.
Claim 33
Dependent Claim 16 words
The process according to claim 19 wherein the free radical generator is high energy ionizing radiation.
Claim 34
Dependent Claim 108 words
A photopolymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR52## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR53## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a photocuring rate accelerator.
Claim 35
Dependent Claim 108 words
A photopolymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR52## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR53## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a photocuring rate accelerator.
Claim 36
Dependent Claim 205 words
The process of coating a substrate which comprises applying to a substrate a curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR54## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is a member of the group consisting of ##STR55## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and thereafter exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate.
Claim 37
Dependent Claim 205 words
The process of coating a substrate which comprises applying to a substrate a curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR54## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is a member of the group consisting of ##STR55## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and thereafter exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate.
Claim 38
Dependent Claim 38 words
The process according to claim 23 wherein the curable composition contains 0.005 to 50% by weight of the polyene and polythiol of said curable composition of a photocuring rate accelerator and the free radical generator is actinic radiation.
Claim 39
Dependent Claim 16 words
The process according to claim 23 wherein the free radical generator is high energy ionizing radiation.
Claim 40
Dependent Claim 231 words
A process for forming a continuous flexible adherent cured coating on the surface of an electrical conductor selected from the group consisting of wire and cable which comprises immersing said electrical conductor in a bath of a liquid radiation curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR56## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is a member of the group consisting of ##STR57## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and thereafter exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate.
Claim 41
Dependent Claim 231 words
A process for forming a continuous flexible adherent cured coating on the surface of an electrical conductor selected from the group consisting of wire and cable which comprises immersing said electrical conductor in a bath of a liquid radiation curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR56## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is a member of the group consisting of ##STR57## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and thereafter exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate.
Claim 42
Dependent Claim 38 words
The process according to claim 26 wherein the curable composition contains 0.005 to 50% by weight of the polyene and polythiol of said curable composition of a photocuring rate accelerator and the free radical generator is actinic radiation.
Claim 43
Dependent Claim 16 words
The process according to claim 26 wherein the free radical generator is high energy ionizing radiation.
Claim 44
Dependent Claim 134 words
The process of coating a substrate which comprises applying to a substrate a polymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR58## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR59## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10 and exposing said compositions under ambient conditions to a free radical generator to form a solidified coating on said substrate.
Claim 45
Dependent Claim 134 words
The process of coating a substrate which comprises applying to a substrate a polymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR58## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR59## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10 and exposing said compositions under ambient conditions to a free radical generator to form a solidified coating on said substrate.
Claim 46
Dependent Claim 31 words
The process according to claim 29 wherein the composition contains 0.005 to 50% by weight of the polyene of a photocuring rate accelerator and the free radical generator is actinic radiation.
Claim 47
Dependent Claim 16 words
The process according to claim 29 wherein the free radical generator is high energy ionizing radiation.
Claim 48
Dependent Claim 156 words
The process of coating a substrate which comprises applying to a substrate a polymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR60## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR61## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and then in either order (2) exposing said curable composition under ambient conditions to a free radical generator to form a solidified, adherent coating on said substrate and (3) heating said cured composition in the range 50°-250° C. to imidize the polyene.
Claim 49
Dependent Claim 156 words
The process of coating a substrate which comprises applying to a substrate a polymerizable composition comprising (A) an amide-acid containing polyene of the formula: ##STR60## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR61## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, and then in either order (2) exposing said curable composition under ambient conditions to a free radical generator to form a solidified, adherent coating on said substrate and (3) heating said cured composition in the range 50°-250° C. to imidize the polyene.
Claim 50
Dependent Claim 31 words
The process according to claim 32 wherein the composition contains 0.005 to 50% by weight of the polyene of a photocuring rate accelerator and the free radical generator is actinic radiation.
Claim 51
Dependent Claim 16 words
The process according to claim 32 wherein the free radical generator is high energy ionizing radiation.
Claim 52
Dependent Claim 267 words
A process for forming a continuous flexible adherent cured coating on the surface of an electrical conductor selected from the group consisting of wire and cable which comprises (1) immersing said electrical conductor in a bath of a liquid radiation curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR62## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR63## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, thus coating said electrical conductor with said composition, (2) passing said coated electrical conductor through a die, then in either order (3) exposing said coated electrical conductor to actinic radiation for a time sufficient to cure said coating on said electrical conductor under ambient conditions and (4) heating said coated electrical conductor in the range 50°-250° C. to imidize the polyene.
Claim 53
Dependent Claim 267 words
A process for forming a continuous flexible adherent cured coating on the surface of an electrical conductor selected from the group consisting of wire and cable which comprises (1) immersing said electrical conductor in a bath of a liquid radiation curable composition comprising (A) an amide-acid containing polyene of the formula: ##STR62## wherein → denotes isomerism, R is a divalent organic moiety remaining after a primary diamine has reacted to form amide linkages; R' is an aromatic residue attached to at least 3 carbonyl groups at least two of which groups are attached to adjacent carbon atoms on the aromatic residue; A is an alkylene group having from 1 to 10 carbon atoms; Y is ##STR63## R" is hydrogen or methyl; k and h are 0 or 1; m and d are 1 to 10 and p is 0 to 10, (B) a polythiol having a molecular weight in the range from about 94 to 20,000 of the general formula: R 8 --(SH) n where n is at least 2 and R 8 is a polyvalent organic moiety, the sum of m and n being greater than 3, the polyene/polythiol mole ratio being in the range 0.2 to 8.0:1, respectively, and (C) a photocuring rate accelerator, thus coating said electrical conductor with said composition, (2) passing said coated electrical conductor through a die, then in either order (3) exposing said coated electrical conductor to actinic radiation for a time sufficient to cure said coating on said electrical conductor under ambient conditions and (4) heating said coated electrical conductor in the range 50°-250° C. to imidize the polyene.

References Cited (Backward Citations)

US3483104A Cited
US3663651A Cited
US3845018A Cited
US3897395A Cited
US3998786A Cited
US3993630A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-09-25 1982-03-27 1982-09-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-09-25 1986-03-27 1986-09-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-09-25 1990-03-27 1990-09-26 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag