Patent US4046749A successfully refreshed from Google Patents.
US4046749A
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Phenylene sulfide oligomer production
Assignee: Phillips Petroleum Co
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Filing: 1975-09-15
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Granted: 1977-09-06
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Expires: 1995-09-15
Abstract
Abstract Phenylene sulfide oligomers are produced by heating at least one aromatic sulfide in an oxygen-containing gaseous atmosphere at an elevated temperature and for a period of time sufficient to form the oligomers. The oligomers can be cured by heating in an oxygen-containing atmosphere while the oligomers are being produced or in a subsequent step after production to yield cured oligomers having utility as coatings, films, and the like.
Inventors
- 👤 Richard T. Hawkins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:30
CPC Classifications
C; C07; C07C; C07C321/00; C08; C08G; C08G75/00; C08G75/02; C08G75/0204; C08G75/025; C08G75/0272; C08G75/0286; C08G75/0295
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
93 words
A process for the production of phenylene sulfide oligomers which comprises heating at least one aromatic sulfide having the formula ##STR11## where m is an integer of 1, 2, or 3 and where the structure of each ##STR12## is selected from ##STR13## in an atmosphere of an oxygen-containing gas and at an elevated temperature and for a period of time sufficient to form a phenylene sulfide oligomer represented by the formula ##STR14## where n is an integer of 2 to about 12 and where the structure of each ##STR15## is selected from ##STR16##
Claim 2
Dependent Claim
93 words
A process for the production of phenylene sulfide oligomers which comprises heating at least one aromatic sulfide having the formula ##STR11## where m is an integer of 1, 2, or 3 and where the structure of each ##STR12## is selected from ##STR13## in an atmosphere of an oxygen-containing gas and at an elevated temperature and for a period of time sufficient to form a phenylene sulfide oligomer represented by the formula ##STR14## where n is an integer of 2 to about 12 and where the structure of each ##STR15## is selected from ##STR16##
Claim 3
Dependent Claim
38 words
A process according to claim 1 wherein said heating is carried out in the presence of a free radical generator selected from sulfur, disulfides, and organic peroxides including hydroperoxides, capable of generating free radicals at the reaction temperature.
Claim 4
Dependent Claim
40 words
A process according to claim 1 wherein the phenylene sulfide oligomer obtained is subjected to additional heating in an atmosphere of an oxygen-containing gas at temperatures higher than about 350° C. for a period of time sufficient to effect cure.
Claim 5
Dependent Claim
54 words
A process according to claim 1 wherein said oligomer is additionally heated to effect cure in an atmosphere of an oxygen-containing gas at a temperature in the range of about 310° C. to about 480° C. and in the presence of a cure promoter selected from sulfur, copper, 2,2'-azobis(2-methylpropionitrile) and organic peroxides including hydroperoxides.
Claim 6
Dependent Claim
59 words
A process according to claim 1 wherein m is 2 or 3 and said heating is conducted at a temperature in the range of about 390° C. to about 420° C. for a period of time in the range of about 30 minutes to about 3 hours to effect phenylene sulfide oligomer production and curing in a single step.
Claim 7
Dependent Claim
52 words
A process according to claim 1 wherein said heating is carried out at a temperature in the range of about 270° C. to about 420° C. for a period of time ranging from about one-fourth hour to about 24 hours and under sufficient pressure to avoid substantial volatilization of aromatic sulfide reactant.
Claim 8
Dependent Claim
37 words
A process according to claim 1 wherein said aromatic sulfide is 1,4-bis(phenylthio)benzene and said oxygen-containing gas is air, and said heating is effected at a temperature in the range of about 300° C. to about 395° C.
Claim 9
Dependent Claim
53 words
A process according to claim 1 wherein said aromatic sulfide is 1,4-bis(phenylthio)benzene and said oxygen-containing gas is air, said heating is effected at a temperature in the range of about 300° C. to about 395° C., and said heating is carried out in the presence of diphenyl disulfide as a free radical generator.
Claim 10
Dependent Claim
30 words
A process according to claim 4 wherein said aromatic sulfide is 1,4-bis(phenylthio)benzene, said oxygen-containing gas is air, and said cure promoter is selected from sulfur, copper, 2,2'-azobis(2-methylpropionitrile) and α,α-dimethylbenzyl hydroperoxide.
Claim 11
Dependent Claim
56 words
A process according to claim 1 wherein said aromatic sulfide is a mixture of 1,4-bis(phenylthio)benzene and 1,3-bis-(phenylthio)benzene, said oxygen-containing gas is air, said heating is effected at a temperature in the range of about 300° C. to about 395° C., and said heating is effected in the presence of diphenyl disulfide as a free radical generator.
Claim 12
Dependent Claim
31 words
A process according to claim 5 wherein said oligomer production and curing are effected in the presence of a cure promoter selected from sulfur, copper, 2,2'-azobis(2-methylpropionitrile), and organic peroxides including hydroperoxides.
Claim 13
Dependent Claim
30 words
A process according to claim 1 wherein said heating is initially effected at a lower temperature and increased as the reaction proceeds, thereby avoiding substantial volatilization of the sulfide reactant.
Claim 14
Dependent Claim
32 words
A process according to claim 1 wherein the oxygen-containing gas is passed through the aromatic sulfide reactant during heating, thereby aiding in removing by-products of lower molecular weight as the reaction proceeds.
Claim 15
Dependent Claim
37 words
A process according to claim 1 wherein said aromatic sulfide is bis[p-(phenylthio)phenyl] sulfide, said oxygen-containing gas is air, and said heating is effected at a temperature in the range of about 300° C. to about 395° C.
Claim 16
Dependent Claim
51 words
A process according to claim 1 wherein said aromatic sulfide is 1,3-bis(phenylthio)benzene, said oxygen-containing gas is air, said heating is effected at a temperature in the range of about 300° C. to about 395° C., and said heating is effected in the presence of diphenyl disulfide as a free radical generator.
Claim 17
Dependent Claim
47 words
A process according to claim 1 wherein the phenylene sulfide oligomer obtained is subjected to additional heating in the absence of a cure promoter at a temperature in the range of about 380° C. to about 430° C. for a period of time sufficient to effect cure.
Claim 18
Dependent Claim
65 words
A process according to claim 1 wherein the phenylene sulfide oligomer obtained is subjected to additional heating in an atmosphere of an oxygen-containing gas at a temperature in the range of about 310° C. to about 350° C. for a period of time sufficient to effect cure and in the presence of a cure promoter selected from sulfur, copper, 2,2'-azobis(2-methylpropionitrile) and organic peroxides including hydroperoxides.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-05 | 1981-03-07 | 1981-09-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-05 | 1985-03-07 | 1985-09-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-05 | 1989-03-07 | 1989-09-06 | $7700.00 | Window Closed / Lapsed |