US4366307A
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US
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Liquid polythioethers
Assignee: PRC Desoto International Inc
•
Filing: 1981-03-30
•
Granted: 1982-12-28
•
Expires: 2001-03-30
Abstract
Abstract A non-crystallizing, water, solvent, fuel and temperature resistant liquid polythioether having two to four terminating radicals which do not substantially reduce the water, solvent, fuel and temperature resistance and a water, solvent, fuel and temperature resistant polymeric backbone having repeating units of the formula: <IMAGE> wherein each of R1, R2, R3 and R4 is hydrogen or lower alkyl providing that a sufficient number of R1, R2, R3 and/or R4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from -CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-S-CH2-CH2- or -CH2-CH2-O-CH2-CH2-; n is 8 to 200; and p is 0 or 1.
Inventors
- 👤 Hakam Singh
- 👤 Jack W. Hutt
- 👤 Morris E. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 09:43
CPC Classifications
C; C08; C08L; C08L71/00; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/52; C08G59/00; C08G59/18; C08G59/20; C08G59/22; C08G59/30; C08G59/302; C08G65/00; C08G65/34; C08G65/48; C08G75/00; C08G75/02; C08G75/12; C08G75/14; C08L63/00
Claims Analysis
Total Claims: 105
Claim 1
Independent Claim
142 words
A non-crystallizing, water, solvent, and fuel resistant liquid polythioether having two to four terminating radicals which do not substantially reduce the water, solvent, and fuel resistance and a water, solvent, and fuel resistant polymeric backbone having repeating units of the formula: ##STR12## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --CH 2 --O--CH 2 --CH 2 --; n is 8 to 200; and p is 0 or 1.
Claim 2
Dependent Claim
142 words
A non-crystallizing, water, solvent, and fuel resistant liquid polythioether having two to four terminating radicals which do not substantially reduce the water, solvent, and fuel resistance and a water, solvent, and fuel resistant polymeric backbone having repeating units of the formula: ##STR12## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --CH 2 --O--CH 2 --CH 2 --; n is 8 to 200; and p is 0 or 1.
Claim 3
Dependent Claim
43 words
A liquid polythioether according to claim 1 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/5.
Claim 4
Dependent Claim
43 words
A liquid polythioether according to claim 1 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/4.
Claim 5
Dependent Claim
14 words
A liquid polythioether according to claim 2 or 3 wherein lower alkyl is methyl.
Claim 6
Dependent Claim
11 words
A liquid polythioether according to claim 1 wherein p is 0.
Claim 7
Dependent Claim
30 words
A liquid polythioether according to claim 1 wherein at least one of R 1 or R 4 is lower alkyl and each of R 2 and R 3 is hydrogen.
Claim 8
Dependent Claim
17 words
A liquid polythioether according to claim 1 wherein said terminating radicals do not exceed twenty carbon atoms.
Claim 9
Dependent Claim
14 words
A liquid polythioether according to claim 7 wherein said terminating radicals are chemically non-reactive.
Claim 10
Dependent Claim
18 words
A liquid polythioether according to claim 8 wherein said polythioether is linear and has two chemically non-reactive radicals.
Claim 11
Dependent Claim
20 words
A liquid polythioether according to claim 8 wherein said polythioether is branched and has 3 or 4 chemically non-reactive radicals.
Claim 12
Dependent Claim
28 words
A liquid polythioether according to claims 9 or 10 wherein said terminating chemically non-reactive radical is selected from the group consisting of aromatic, alkyl, heteroalkyl, alicyclic and heteroalicyclic.
Claim 13
Dependent Claim
22 words
A liquid polythioether according to claim 11 wherein the number of carbon atoms in said chemically non-reactive radical does not exceed ten.
Claim 14
Dependent Claim
17 words
A liquid polythioether according to claim 8 wherein said terminating chemically non-reactive radical is thioalicyclic or oxyalicyclic.
Claim 15
Dependent Claim
15 words
A liquid polythioether according to claim 8 wherein said terminating chemically non-reactive radical is aromatic.
Claim 16
Dependent Claim
15 words
A liquid polythioether according to claim 8 wherein said terminating chemically non-reactive radical is heteroalkyl.
Claim 17
Dependent Claim
15 words
A liquid polythioether according to claim 8 wherein said terminating chemically non-reactive radical is alkyl.
Claim 18
Dependent Claim
20 words
A liquid polythioether according to claim 15 wherein said heteroalkyl is selected from the group consisting of thioalkyl and oxyalkyl.
Claim 19
Dependent Claim
13 words
A liquid polythioether according to claim 1 wherein said terminating radicals are vulcanizable.
Claim 20
Dependent Claim
17 words
A liquid polythioether according to claim 18 wherein said polythioether is linear and has two vulcanizable radicals.
Claim 21
Dependent Claim
19 words
A liquid polythioether according to claim 18 wherein said polythioether is branched and has 3 or 4 vulcanizable radicals.
Claim 22
Dependent Claim
13 words
A liquid polythioether according to claim 19 wherein said vulcanizable radical is hydroxyl.
Claim 23
Dependent Claim
14 words
A liquid polythioether according to claim 19 wherein said vulcanizable radical is reactive silyl.
Claim 24
Dependent Claim
31 words
A liquid polythioether according to claim 20 wherein said low temperature vulcanizable radical is selected from the group consisting of hydroxyl, epoxide, reactive silyl, isocyanate, reactive olefinic double bond and mercaptan.
Claim 25
Dependent Claim
13 words
A liquid polythioether according to claim 23 wherein said vulcanizable radical is hydroxyl.
Claim 26
Dependent Claim
16 words
A liquid polythioether according to claim 23 wherein said vulcanizable radical is reactive olefinic double bond.
Claim 27
Dependent Claim
13 words
A liquid polythioether according to claim 23 wherein the vulcanizable radical is epoxide.
Claim 28
Dependent Claim
13 words
A liquid polythioether according to claim 23 wherein the vulcanizable radical is isocyanate.
Claim 29
Dependent Claim
13 words
A liquid polythioether according to claim 23 wherein the vulcanizable radical is mercaptan.
Claim 30
Dependent Claim
132 words
A non-crystallizing, linear, water, solvent and fuel resistant liquid polythioether having the formula ##STR13## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl with the provision that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 --, or --CH 2 --CH 2 --O--CH 2 --CH 2 --; n is 8 to 200, p is 0 or 1 and B is a terminating radical which does not substantially reduce the water, solvent and fuel resistance.
Claim 31
Dependent Claim
132 words
A non-crystallizing, linear, water, solvent and fuel resistant liquid polythioether having the formula ##STR13## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl with the provision that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 --, or --CH 2 --CH 2 --O--CH 2 --CH 2 --; n is 8 to 200, p is 0 or 1 and B is a terminating radical which does not substantially reduce the water, solvent and fuel resistance.
Claim 32
Dependent Claim
43 words
A liquid polythioether according to claim 29 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/5.
Claim 33
Dependent Claim
43 words
A liquid polythioether according to claim 29 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/4.
Claim 34
Dependent Claim
30 words
A liquid polythioether according to claim 29 wherein at least one of R 1 or R 4 is lower alkyl and each of R 2 and R 3 is hydrogen.
Claim 35
Dependent Claim
15 words
A liquid polythioether according to claims 30, 31 or 32 wherein lower alkyl is methyl.
Claim 36
Dependent Claim
11 words
A liquid polythioether according to claim 29 wherein p is 0.
Claim 37
Dependent Claim
17 words
A liquid polythioether according to claim 29 wherein said terminating radical does not exceed twenty carbon atoms.
Claim 38
Dependent Claim
14 words
A liquid polythioether according to claim 29 wherein said terminating radical is chemically non-reactive.
Claim 39
Dependent Claim
24 words
A liquid polythioether according to claim 36 wherein said chemically non-reactive radical selected from the group consisting of aromatic, alkyl, heteroalkyl, alicyclic and heteroalicyclic.
Claim 40
Dependent Claim
22 words
A liquid polythioether according to claim 37 wherein the number of carbon atoms in said chemically non-reactive radical does not exceed ten.
Claim 41
Dependent Claim
16 words
A liquid polythioether according to claim 37 wherein said chemically non-reactive radical is thioalicyclic or oxyalicyclic.
Claim 42
Dependent Claim
14 words
A liquid polythioether according to claim 37 wherein said chemically non-reactive radical is aromatic.
Claim 43
Dependent Claim
14 words
A liquid polythioether according to claim 37 wherein said chemically non-reactive radical is heteroalkyl.
Claim 44
Dependent Claim
14 words
A liquid polythioether according to claim 37 wherein said chemically non-reactive radical is alkyl.
Claim 45
Dependent Claim
20 words
A liquid polythioether according to claim 41 wherein said heteroalkyl is selected from the group consisting of thioalkyl and oxyalkyl.
Claim 46
Dependent Claim
17 words
A liquid polythioether according to claims 20 or 35 wherein said terminating radical is a vulcanizable radical.
Claim 47
Dependent Claim
33 words
A liquid polythioether according to claim 44 wherein said vulcanizable radical is selected from the group consisting of epoxide, reactive silyl, isocyanate, reactive olefinic double bond, mercaptan and hydrogen of a hydroxyl group.
Claim 48
Dependent Claim
13 words
A liquid polythioether according to claim 44 wherein the vulcanizable radical is epoxy.
Claim 49
Dependent Claim
14 words
A liquid polythioether according to claim 44 wherein the vulcanizable radical is reactive silyl.
Claim 50
Dependent Claim
13 words
A liquid polythioether according to claim 44 wherein the vulcanizable radical is isocyanate.
Claim 51
Dependent Claim
13 words
A liquid polythioether according to claim 44 wherein the vulcanizable radical is mercaptan.
Claim 52
Dependent Claim
178 words
A non-crystallizing, branched, water, solvent, and fuel resistant liquid polythioether, said liquid polythioether having the formula R--(A--O--B) m wherein R is the fragment of the organic triol or tetrol R--(OH) m having a molecular weight of less than 400; m is 3 or 4; B is a terminating radical which does not substantially reduce the water, solvent, and fuel resistance; and A is a polymeric backbone of repeating units of the formula ##STR14## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 , --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --Ch 2 --O--CH 2 --CH 2 --; n is 8 to 200; m is 3 or 4; and p is 0 to 1.
Claim 53
Dependent Claim
178 words
A non-crystallizing, branched, water, solvent, and fuel resistant liquid polythioether, said liquid polythioether having the formula R--(A--O--B) m wherein R is the fragment of the organic triol or tetrol R--(OH) m having a molecular weight of less than 400; m is 3 or 4; B is a terminating radical which does not substantially reduce the water, solvent, and fuel resistance; and A is a polymeric backbone of repeating units of the formula ##STR14## wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 , --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --Ch 2 --O--CH 2 --CH 2 --; n is 8 to 200; m is 3 or 4; and p is 0 to 1.
Claim 54
Dependent Claim
18 words
A liquid polythioether according to claim 50 wherein R--(OH) m has a molecular weight of less than 360.
Claim 55
Dependent Claim
20 words
A liquid polythioether according to claim 51 wherein each hydroxyl is R--(OH) m is located beta to a sulfur atom.
Claim 56
Dependent Claim
15 words
A liquid polythioether according to claim 52 wherein R is aliphatic sulfide or heteroaliphatic sulfide.
Claim 57
Dependent Claim
43 words
A liquid polythioether according to claim 50 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/5.
Claim 58
Dependent Claim
43 words
A liquid polythioether according to claim 50 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/4.
Claim 59
Dependent Claim
30 words
A liquid polythioether according to claim 50 wherein at least one of R 1 or R 4 is lower alkyl and each of R 2 and R 3 is hydrogen.
Claim 60
Dependent Claim
12 words
A liquid polythioether according to claim 56 wherein lower alkyl is methyl.
Claim 61
Dependent Claim
11 words
A liquid polythioether according to claim 50 where p is 0.
Claim 62
Dependent Claim
17 words
A liquid polythioether according to claim 50 wherein said terminating radical does not exceed twenty carbon atoms.
Claim 63
Dependent Claim
14 words
A liquid polythioether according to claim 59 wherein said terminating radical is chemically non-reactive.
Claim 64
Dependent Claim
26 words
A liquid polythioether according to claim 60 wherein said terminal chemically non-reactive radical is selected from the group consisting of aromatic , heteroalkyl, alicyclic and heteroalicyclic.
Claim 65
Dependent Claim
23 words
A liquid polythioether according to claim 61 wherein the number of carbon atoms in said terminal chemically non-reactive radical does not exceed ten.
Claim 66
Dependent Claim
17 words
A liquid polythioether according to claim 60 wherein said terminal chemically non-reactive radical is thioalicyclic or oxyalicyclic.
Claim 67
Dependent Claim
15 words
A liquid polythioether according to claim 60 wherein said terminal chemically non-reactive radical is aromatic.
Claim 68
Dependent Claim
15 words
A liquid polythioether according to claim 60 wherein said terminal chemically non-reactive radical is heteroalkyl.
Claim 69
Dependent Claim
15 words
A liquid polythioether according to claim 60 wherein said terminal chemically non-reactive radical is alkyl.
Claim 70
Dependent Claim
15 words
A liquid polythioether according to claims 50 or 59 wherein said terminating radical is vulcanizable.
Claim 71
Dependent Claim
33 words
A liquid polythioether according to claim 67 wherein said vulcanizable radical is selected from the group consisting of epoxide, reactive silyl, isocyanate, reactive olefinic double bond, mercaptan and hydrogen of a hydroxyl group.
Claim 72
Dependent Claim
13 words
A liquid polythioether according to claim 67 wherein the vulcanizable radical is epoxide.
Claim 73
Dependent Claim
14 words
A liquid polythioether according to claim 67 wherein the vulcanizable radical is reactive silyl.
Claim 74
Dependent Claim
13 words
A liquid polythioether according to claim 67 wherein the vulcanizable radical is isocyanate.
Claim 75
Dependent Claim
13 words
A liquid polythioether according to claim 67 wherein the vulcanizable radical is mercaptan.
Claim 76
Dependent Claim
16 words
A liquid polythioether according to claim 67 wherein the vulcanizable radical is hydrogen of a hydroxyl.
Claim 77
Dependent Claim
151 words
A non-crystallizing, water, solvent, and fuel resistant liquid polythioether having the formula ##STR15## wherein Z is hetero(lower) aliphatic; B is a terminating radical which does not substantially reduce the water, solvent, and fuel resistance; A is a polymeric backbone consisting of repeating units of the formula ##STR16## each of a, b, and p is 0 or 1; each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --CH 2 --O--CH 2 --CH 2 --; and n is 8 to 200.
Claim 78
Dependent Claim
151 words
A non-crystallizing, water, solvent, and fuel resistant liquid polythioether having the formula ##STR15## wherein Z is hetero(lower) aliphatic; B is a terminating radical which does not substantially reduce the water, solvent, and fuel resistance; A is a polymeric backbone consisting of repeating units of the formula ##STR16## each of a, b, and p is 0 or 1; each of R 1 , R 2 , R 3 and R 4 is hydrogen or lower alkyl providing that a sufficient number of R 1 , R 2 , R 3 and/or R 4 are lower alkyl in said polymeric backbone to render said backbone non-crystallizing; X is a divalent organic radical selected from --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --CH 2 --, --CH 2 --CH 2 --S--CH 2 --CH 2 -- or --CH 2 --CH 2 --O--CH 2 --CH 2 --; and n is 8 to 200.
Claim 79
Dependent Claim
13 words
A liquid polythioether according to claim 74 wherein a and b are 0.
Claim 80
Dependent Claim
15 words
A liquid polythioether according to claim 74 wherein b is 0 and a is 1.
Claim 81
Dependent Claim
43 words
A liquid polythioether according to claim 74 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymer backbone is at least the nearest whole number to the quotient of n/5.
Claim 82
Dependent Claim
43 words
A liquid polythioether according to claim 74 wherein the total number of R 1 , R 2 , R 3 and/or R 4 which are lower alkyl in said polymeric backbone is at least the nearest whole number to the quotient of n/4.
Claim 83
Dependent Claim
30 words
A liquid polythioether according to claim 74 wherein at least one of R 1 or R 4 is lower alkyl and each of R 2 and R 3 is hydrogen.
Claim 84
Dependent Claim
15 words
A liquid polythioether according to claims 77, 78 and 79 wherein lower alkyl is methyl.
Claim 85
Dependent Claim
11 words
A liquid polythioether according to claim 74 wherein p is 0.
Claim 86
Dependent Claim
14 words
A liquid polythioether according to claim 74 wherein said terminating radical is chemically non-reactive.
Claim 87
Dependent Claim
25 words
A liquid polythioether according to claim 74 wherein said chemically non-reactive radical is selected from the group consisting of aromatic, alkyl, heteroalkyl, alicyclic and heteroalicyclic.
Claim 88
Dependent Claim
23 words
A liquid polythioether according to claim 82 wherein the number of carbon atoms in said terminal chemically non-reactive radical does not exceed ten.
Claim 89
Dependent Claim
17 words
A liquid polythioether according to claim 82 wherein said terminating chemically non-reactive radical is thioalicyclic or oxyalicyclic.
Claim 90
Dependent Claim
15 words
A liquid polythioether according to claim 82 wherein said terminating chemically non-reactive radical is aromatic.
Claim 91
Dependent Claim
15 words
A liquid polythioether according to claim 82 wherein said terminating chemically non-reactive radical is heteroalkyl.
Claim 92
Dependent Claim
15 words
A liquid polythioether according to claim 82 wherein said terminating chemically non-reactive radical is alkyl.
Claim 93
Dependent Claim
20 words
A liquid polythioether according to claim 87 wherein said heteralkyl is selected from the group consisting of thioalkyl and oxyalkyl.
Claim 94
Dependent Claim
13 words
A liquid polythioether according to claim 74 wherein said terminating radical is vulcanizable.
Claim 95
Dependent Claim
33 words
A liquid polythioether according to claim 90 wherein said vulcanizable radical is selected from the group consisting of epoxide, reactive silyl, isocyanate, reactive olefinic double bond, mercaptan and hydrogen of a hydroxyl group.
Claim 96
Dependent Claim
13 words
A liquid polythioether according to claim 90 wherein the vulcanizable radical is epoxide.
Claim 97
Dependent Claim
14 words
A liquid polythioether according to claim 90 wherein the vulcanizable radical is reactive silyl.
Claim 98
Dependent Claim
13 words
A liquid polythioether according to claim 90 wherein the vulcanizable radical is isocyanate.
Claim 99
Dependent Claim
13 words
A liquid polythioether according to claim 90 wherein the vulcanizable radical is mercaptan.
Claim 100
Dependent Claim
18 words
A liquid polythioether according to claim 90 wherein the vulcanizable radical is the hydrogen of a hydroxyl group.
Claim 101
Dependent Claim
12 words
A liquid polythioether according to claim 74 wherein Z is oxy(lower) aliphatic.
Claim 102
Dependent Claim
12 words
The solid vulcanized elastomeric polythioether of the liquid polythioether of claim 18.
Claim 103
Dependent Claim
12 words
The solid vulcanized elastomeric polythioether of the liquid polythioether of claim 44.
Claim 104
Dependent Claim
12 words
The solid vulcanized elastomeric polythioether of the liquid polythioether of claim 67.
Claim 105
Dependent Claim
12 words
The solid vulcanized elastomeric polythioether of the liquid polythioether of claim 90.
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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) | 1985-12-27 | 1986-06-28 | 1986-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-27 | 1990-06-28 | 1990-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-27 | 1994-06-28 | 1994-12-28 | $7700.00 | Window Closed / Lapsed |