US4587312A
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Sulfone-ester polymers containing pendent ethynyl groups
Assignee: National Aeronautics and Space Administration
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Filing: 1984-05-23
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Granted: 1986-05-06
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Expires: 2004-05-23
Abstract
Abstract Sulfone-ester polymers containing pendent ethynyl groups and a direct and multi-step process for preparing same are disclosed. The multi-step process involves the conversion of a pendent bromo group to the ethynyl group while the direct route involves reacting hydroxy-terminated sulfone oligomer or polymers with a stoichiometric amount of 5-(4-ethynylphenoxy)isophthaloyl chloride. The 5-(4-ethynylphenoxy)isophthaloyl chloride and process for preparing same are also disclosed.
Inventors
- 👤 Paul M. Hergenrother
- 👤 Brian J. Jensen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:10
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/688; C08G63/6884; C08G63/6888; C07; C07C; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07C65/00; C07C65/21; C07C65/28; C08G63/91; C08G63/914; C08G63/918; C08G65/00; C08G65/34; C08G65/48
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
38 words
The class of ethynyl containing sulfone-esters having the general formula ##STR3## where PS is an polyarylene ether sulfone with an number average molecular weight of less than 50,000 g/mole, and n is an integer of 1 or greater.
Claim 2
Dependent Claim
38 words
The class of ethynyl containing sulfone-esters having the general formula ##STR3## where PS is an polyarylene ether sulfone with an number average molecular weight of less than 50,000 g/mole, and n is an integer of 1 or greater.
Claim 3
Dependent Claim
23 words
The crosslinked polymer recovered by thermally reacting the sulfone-ester polymer of claim 1 in the temperature range of 200°-300° C. for thirty minutes.
Claim 4
Dependent Claim
43 words
A method of making the ethynyl terminated sulfone-ester polymer of claim 1 comprising: providing an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight less than 50,000 g/mole, and reacting this oligomer or polymer with a stoichiometric amount of 5-(4-ethynylphenoxy)isophthaloyl chloride.
Claim 5
Dependent Claim
68 words
A method of making the ethynyl terminated sulfone-ester or polymer of claim 1 comprising: providing an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight less than 50,000 g/mole, and reacting this oligomer or polymer with a stoichiometric amount of a diacid chloride consisting of a mixture of 5-(4-ethynylphenoxy)isophthaloyl chloride and one or more of the group consisting of isophthaloyl chloride, terephthaloyl chloride and 4,4'-methylenebisbenzoyl chloride.
Claim 6
Independent Claim
88 words
A method of making an ethynyl containing sulfone-ester polymer comprising: providing a quantity of hydroxy-terminated sulfone oligomer or polymer, reacting this oligomer or polymer in a dry solvent selected from the group consisting of methylene chloride, chloroform and N,N-dimethylacetamide with 5-(4-bromophenoxy)isophthaloyl chloride to form a sulfone-ester polymer containing pendent bromo groups, displacing the bromo groups by trimethylsilylacetylene in an organic solvent and using a palladium catalyst, and cleaving the trimethysilyl group with a weak base to recover a light tan solid of sulfone-ester polymer containing pendent ethynyl groups.
Claim 7
Independent Claim
88 words
A method of making an ethynyl containing sulfone-ester polymer comprising: providing a quantity of hydroxy-terminated sulfone oligomer or polymer, reacting this oligomer or polymer in a dry solvent selected from the group consisting of methylene chloride, chloroform and N,N-dimethylacetamide with 5-(4-bromophenoxy)isophthaloyl chloride to form a sulfone-ester polymer containing pendent bromo groups, displacing the bromo groups by trimethylsilylacetylene in an organic solvent and using a palladium catalyst, and cleaving the trimethysilyl group with a weak base to recover a light tan solid of sulfone-ester polymer containing pendent ethynyl groups.
Claim 8
Dependent Claim
34 words
A sulfone-ester polymer containing pendent ethynyl groups and formed as the reaction product of an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight of less than 50,000 g/mole and 5-(4-ethynylphenoxy)isophthaloyl chloride.
Claim 9
Dependent Claim
34 words
A sulfone-ester polymer containing pendent ethynyl groups and formed as the reaction product of an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight of less than 50,000 g/mole and 5-(4-ethynylphenoxy)isophthaloyl chloride.
Claim 10
Dependent Claim
62 words
A sulfone-ester polymer containing pendent ethynyl groups and formed as the reaction product of: (1) an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight less than 50,000 g/mole, and (2) a mixture of diacid chlorides at least one of which is 5-4(-ethynylphenoxy)isopthaloyl chloride and one or more of the group consisting of isophthaloyl chloride, terephthaloyl chloride and 4,4'-methylenebisbenzoyl chloride.
Claim 11
Dependent Claim
62 words
A sulfone-ester polymer containing pendent ethynyl groups and formed as the reaction product of: (1) an hydroxy-terminated sulfone oligomer or polymer having a number average molecular weight less than 50,000 g/mole, and (2) a mixture of diacid chlorides at least one of which is 5-4(-ethynylphenoxy)isopthaloyl chloride and one or more of the group consisting of isophthaloyl chloride, terephthaloyl chloride and 4,4'-methylenebisbenzoyl chloride.
Claim 12
Dependent Claim
41 words
The sulfone-ester polymer containing pendent ethynyl groups as in claim 7 and crosslinked by thermal treatment for approximately thirty minutes in the range of 200°-300° C. to yield a polymer having improved solvent resistance and thermal use properties over uncrosslinked polymers.
Claim 13
Independent Claim
58 words
A method of making an ester polymer containing pendent ethynyl groups comprising: reacting stoichiometric quantities of an acid chloride and a dihydroxy compound wherein the acid chloride is selected from the group consisting of 5-(4-ethynylphenoxy)isophthaloyl chloride and a mixture of 5-(4-ethynylphenoxy)isophthaloyl chloride and one or more of the group consisting of isophthaloyl chloride, terephthaloyl chloride and 4,4'-methylenebisbenzoyl chloride.
Claim 14
Independent Claim
58 words
A method of making an ester polymer containing pendent ethynyl groups comprising: reacting stoichiometric quantities of an acid chloride and a dihydroxy compound wherein the acid chloride is selected from the group consisting of 5-(4-ethynylphenoxy)isophthaloyl chloride and a mixture of 5-(4-ethynylphenoxy)isophthaloyl chloride and one or more of the group consisting of isophthaloyl chloride, terephthaloyl chloride and 4,4'-methylenebisbenzoyl chloride.
Claim 15
Dependent Claim
24 words
The method of claim 9 wherein the dihydroxy compound is selected from the group consisting of bisphenol A, 4,4'-oxydiphenol, 4,4'-oxydithiophenol, resorcinol, hydroquinone and 4,4'-dihydroxybiphenyl.
Claim 16
Dependent Claim
30 words
The class of ethynyl ester polymers having the general formula ##STR4## where Y is selected from the group consisting of ##STR5## and n is an integer of 10 to 200.
Claim 17
Dependent Claim
30 words
The class of ethynyl ester polymers having the general formula ##STR4## where Y is selected from the group consisting of ##STR5## and n is an integer of 10 to 200.
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) | 1989-05-05 | 1989-11-04 | 1990-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-05 | 1993-11-04 | 1994-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-05 | 1997-11-04 | 1998-05-06 | $7700.00 | Window Closed / Lapsed |