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US4080484A Expired / Lapsed US ⏱️ 0.0 years remaining

Photocurable imidizable polyene-polythiol compositions, method of coating therewith and coated articles

Assignee: WR Grace and Co
•
Filing: 1976-12-23
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Granted: 1978-03-21
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Expires: 1996-12-23
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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 2026-10-24 14:20
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: 44
Claim 1
Independent Claim 113 words
An amide-acid polyene of the formula: ##STR21## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR22## 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 113 words
An amide-acid polyene of the formula: ##STR21## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR22## 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 118 words
An imide-containing polyene of the formula ##STR23## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR24## 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 118 words
An imide-containing polyene of the formula ##STR23## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR24## 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 190 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 ##STR25## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR26## 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 190 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 ##STR25## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR26## 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 13 words
The method according to claim 3 wherein the anhydride-containing member is a dianhydride.
Claim 8
Dependent Claim 14 words
The method according to claim 3 wherein the anhydride-containing member is an acid anhydride.
Claim 9
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 10
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 11
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 12
Dependent Claim 184 words
A photocurable composition comprising (A) an amide-acid containing polyene of the formula: ##STR27## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR28## 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 184 words
A photocurable composition comprising (A) an amide-acid containing polyene of the formula: ##STR27## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR28## 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 188 words
A photocurable composition comprising (A) an imide-containing polyene of the formula: ##STR29## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR30## 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 15
Dependent Claim 188 words
A photocurable composition comprising (A) an imide-containing polyene of the formula: ##STR29## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR30## 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 16
Dependent Claim 199 words
The process of forming a solid cured amide-acid containing polythioether which comprises admixing (A) a polyene of the formula: ##STR31## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR32## 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)HD 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 17
Dependent Claim 199 words
The process of forming a solid cured amide-acid containing polythioether which comprises admixing (A) a polyene of the formula: ##STR31## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR32## 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)HD 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 18
Dependent Claim 222 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR33## 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 --CR"═CH 2 , --O--(CH 2 ) d --CH"═CH 2 and ##STR34## 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 exposing said admixture to actinic radiation and, thereafter, heating the cured polythioether at a temperature in the range 50°-250° C for a time sufficient to imidize the amide-acid in the polyene.
Claim 19
Dependent Claim 222 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR33## 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 --CR"═CH 2 , --O--(CH 2 ) d --CH"═CH 2 and ##STR34## 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 exposing said admixture to actinic radiation and, thereafter, heating the cured polythioether at a temperature in the range 50°-250° C for a time sufficient to imidize the amide-acid in the polyene.
Claim 20
Dependent Claim 268 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR35## 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 1 to 10 carbon atoms; Y is a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR36## 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 0.01-5% by weight of (A) and (B) of a pinacol of the general formula: ##STR37## 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 21
Dependent Claim 268 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR35## 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 1 to 10 carbon atoms; Y is a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR36## 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 0.01-5% by weight of (A) and (B) of a pinacol of the general formula: ##STR37## 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 22
Dependent Claim 206 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) an imide containing polyene of the formula: ##STR38## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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. and, thereafter, exposing the mixture to actinic radiation.
Claim 23
Dependent Claim 206 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) an imide containing polyene of the formula: ##STR38## 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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. and, thereafter, exposing the mixture to actinic radiation.
Claim 24
Dependent Claim 274 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 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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 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 25
Dependent Claim 274 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 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 a member of the group consisting of --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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 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 26
Dependent Claim 228 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR43## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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 heating said admixture at a temperature in the range 50°-250° C for a time sufficient to imidize the amide-acid in the polyene and, thereafter, exposing said admixture to actinic radiation to form a cured imide containing polythioether.
Claim 27
Dependent Claim 228 words
The process of forming a solid cured imide containing polythioether which comprises admixing (A) a polyene of the formula: ##STR43## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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 heating said admixture at a temperature in the range 50°-250° C for a time sufficient to imidize the amide-acid in the polyene and, thereafter, exposing said admixture to actinic radiation to form a cured imide containing polythioether.
Claim 28
Dependent Claim 14 words
An article comprising the composition of claim 9 as a coating on a substrate.
Claim 29
Dependent Claim 13 words
The article according to claim 17 wherein the substrate is an electrical conductor.
Claim 30
Dependent Claim 14 words
An article comprising the composition of claim 10 as a coating on a substrate.
Claim 31
Dependent Claim 12 words
The article of claim 19 wherein the substrate is an electrical conductor.
Claim 32
Dependent Claim 14 words
An article comprising a cured amide-acid containing polythioether as a coating on a substrate.
Claim 33
Dependent Claim 14 words
An article comprising a cured amide-acid containing polythioether as a coating on a substrate.
Claim 34
Dependent Claim 13 words
The article according to claim 21 wherein the substrate is an electrical conductor.
Claim 35
Dependent Claim 14 words
An article comprising a cured imide containing polythioether as a coating on a substrate.
Claim 36
Dependent Claim 14 words
An article comprising a cured imide containing polythioether as a coating on a substrate.
Claim 37
Dependent Claim 13 words
The article according to claim 23 wherein the substrate is an electrical conductor.
Claim 38
Dependent Claim 13 words
The article according to claim 24 wherein the electrical conductor is a wire.
Claim 39
Dependent Claim 228 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: ##STR45## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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, 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, exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate and, thereafter heating said cured composition in the range 50°-250° C to imidize the polyene.
Claim 40
Dependent Claim 228 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: ##STR45## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##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, 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, exposing said curable composition under ambient conditions to a free radical generator to form a solidified, cured polythioether coating on said substrate and, thereafter heating said cured composition in the range 50°-250° C to imidize the polyene.
Claim 41
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 42
Dependent Claim 16 words
The process according to claim 26 wherein the free radical generator is high energy ionizing radiation.
Claim 43
Dependent Claim 277 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: ##STR47## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR48## 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, passing said coated electrical conductor through a die, exposing said coated electrical conductor to actinic radiation for a time sufficient to cure said coating on said electrical conductor under ambient conditions and, thereafter, heating said coated electrical conductor in the range 50°-250° C to imidize the polyene.
Claim 44
Dependent Claim 277 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: ##STR47## 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 --CR"═CH 2 , --O--(CH 2 ) d --CR"═CH 2 and ##STR48## 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, passing said coated electrical conductor through a die, exposing said coated electrical conductor to actinic radiation for a time sufficient to cure said coating on said electrical conductor under ambient conditions and, thereafter, heating said coated electrical conductor in the range 50°-250° C to imidize the polyene.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-03-20 1981-09-19 1982-03-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-03-20 1985-09-19 1986-03-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-03-20 1989-09-19 1990-03-21 $7700.00 Window Closed / Lapsed

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