Cross-linked organic polymers for use as elastomers in high temperature applications
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-065/48
C08G-016/00
C08G-008/28
C08G-061/12
출원번호
US-0216659
(2014-03-17)
등록번호
US-9109075
(2015-08-18)
발명자
/ 주소
Drake, Kerry A.
Song, Le
Burgoyne, Jr., William F.
출원인 / 주소
Delsper LP
대리인 / 주소
Flaster/Greenberg PC
인용정보
피인용 횟수 :
0인용 특허 :
41
초록▼
Methods are disclosed to prepare elastomeric materials by providing aromatic polymer(s) which is/are non-elastomeric at room temperature; cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer which is substantially cured; and heating the cross-link
Methods are disclosed to prepare elastomeric materials by providing aromatic polymer(s) which is/are non-elastomeric at room temperature; cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer which is substantially cured; and heating the cross-linked aromatic polymer to a temperature at or above a glass transition temperature of the cross-linked aromatic polymer. Materials formed thereby and end products are also described which may be formed using the aromatic polymer cross-linking techniques to develop strong elastomeric materials for high temperature and/or harsh condition end applications.
대표청구항▼
1. A method of preparing an elastomeric material, comprising (a) providing an aromatic polymer which is non-elastomeric at room temperature;(b) cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer that is substantially cured, wherein the cross-lin
1. A method of preparing an elastomeric material, comprising (a) providing an aromatic polymer which is non-elastomeric at room temperature;(b) cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer that is substantially cured, wherein the cross-linking compound has a structure according to formula (II): wherein A is an arene moiety having a molecular weight of less than 10,000 g/mol, R1 is selected from a group consisting of hydroxide (—OH), amine (—NH2), halide, ether, ester, or amide, and x is about 2.0 to about 6.0; and (c) heating the cross-linked aromatic polymer to a temperature at or above a glass transition temperature of the cross-linked aromatic polymer. 2. The method of preparing an elastomeric material according to claim 1, wherein, in step (b), the aromatic polymer is at least about 80% cured. 3. The method of preparing an elastomeric material according to claim 2, wherein the aromatic polymer is at least about 90% cured. 4. The method of preparing an elastomeric material according to claim 3, wherein the aromatic polymer is fully cured. 5. The method of preparing an elastomeric material according to claim 1, wherein the aromatic polymer is selected from the group consisting of poly(arylene ether)s, polysulfones, polyethersulfones, polyarylene sulfides, polyimides, polyamides, polyureas, polyurethanes, polyphthalamides, polyamide-imides, poly(benzimidazole)s, polyarylates, liquid crstalline polymers (LCPs) and polyaramids. 6. The method of preparing an elastomeric material according to claim 1, wherein the aromatic polymer is a poly(arylene ether) including polymer repeating units having the following structure: —(—O—Ar1—O—Ar2—)m(—O—Ar3—O—Ar4—)n— wherein Ar1,Ar2, Ar3 and Ar4 are identical or different aryl radicals, m=0 to 1.0, and n=1 m. 7. The method of preparing an elastomeric material according to claim 1, wherein the cross-linking compound has a structure selected from a group consisting of 8. The method of preparing an elastomeric material according to claim 1, wherein the arene moiety has a molecular weight of about 1,000 g/mol to about 9,000 g/mol. 9. The method of preparing an elastomeric material according to claim 1, wherein the arene moiety has a molecular weight of about 2,000 g/mol to about 7,000 g/mol. 10. The method of preparing an elastomeric material according to claim 1, wherein step (b) further comprises cross-linking the organic polymer with the cross-linking compound and a cross-linking reaction additive selected from an organic acid and/or an acetate compound, wherein the cross-linking reaction additive is capable of reacting with the cross-linking compound to form a reactive intermediate in the form of an oligomer, which reactive intermediate oligomer is capable of cross-linking the organic polymer. 11. The method of preparing an elastomeric material according to claim 10, wherein the cross-linking reaction additive is an organic acid selected from glacial acetic acid, formic acid, and/or benzoic acid. 12. The method of preparing an elastomeric material according to claim 10, wherein the cross-linking reaction additive is an acetate compound having a structure according to formula (XI): wherein M is a Group I or a Group II metal; and R2 is a alkyl, aryl or aralkyl group, wherein the alkyl group comprises a hydrocarbon group of 1 to about 15 carbon atoms which has from 0 to about 5 ester or ether groups along or in a chain of the hydrocarbon group, and wherein R2 comprises 0 to about 5 functional groups selected from sulfate, phosphate, hydroxyl, carbonyl, ester, halide, mercapto or potassium. 13. The method of preparing an elastomeric material according to claim 12, wherein the acetate compound is selected from lithium acetate hydrate sodium acetate, and/or potassium acetate, and salts and derivatives thereof. 14. The method of preparing an elastomeric material according to claim 10, wherein the weight percentage ratio of the cross-linking compound to the cross-linking reaction additive is about 10:1 to about 10,000:1. 15. The method of preparing an elastomeric material according to claim 14, wherein the weight percentage ratio of the cross-linking compound to the cross-linking reaction additive is about 20:1 to about 1000:1. 16. The method of preparing an elastomeric material according to claim 1, wherein the method further comprises forming a composition comprising the cross-linked organic polymer and heating the composition to form a molded article and step (c) further comprises placing the molded article in use at a temperature at or above the glass transition temperature of the cross-linked organic polymer. 17. An article formed by the method of claim 1. 18. The article according to claim 17, selected from the group consisting of an O-ring, a V-ring, a U-cup, a gasket, at least one component of a seal stack, a packer element, a diaphragm, a thee seal, a bearing, a valve seat, an adapter, a wiper ring, a chevron seal back-up ring, an tubing. 19. A method of preparing an elastomeric material, comprising (a) providing an aromatic polymer which is non-elastomeric at room temperature;(b) cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer that is substantially cured; and(c) heating the cross-linked aromatic polymer to a temperature at or above a glass transition temperature of the cross-linked aromatic polymer,and wherein the aromatic polymer is a poly(arylene ether), and the polymer has repeating units having the structure of formula (I): 20. An elastomeric material formed by heating a cross-linked aromatic polymer that is substantially cured at or above a glass transition temperature of the cross-linked aromatic polymer, wherein the aromatic polymer is not elastomeric at room temperature prior to cross-linking, and wherein the aromatic polymer is cross-linked by reaction with a cross-linking compound having a structure according to formula (II): wherein A is an arene moiety having molecular weight of less than 10,000 g/mol, R1 is selected from a group consisting of hydroxide(—OH), amine (—NH2), halide, ether, ester, or amide, and x is about 2.0 to about 6.0, or by thermally induced cross-linking of an aromatic polymer having a graft bonded to the aromatic polymer. 21. An elastomeric article formed by heat molding a composition comprising a cross-linked aromatic polymer to form a molded article, wherein the aromatic polymer is not elastomeric at room temperature prior to cross-linking, and wherein the cross-linked aromatic polymer is substantially cured, and heating the molded article at or above a glass transition temperature of the cross-linked aromatic polymer, wherein the aromatic polymer is cross-linked by reaction with a cross-linking compound having a structure according to formula (II): wherein A is an arene moiety having a molecular weight of less than 10,000 g/mol, R1 is selected from a group consisting of hydroxide (—OH),amine (—NH2) halide, ether, ester, or, amide, and x is about 2.0 to about 6.0, or by thermally induced cross-linking of an aromatic polymer having a graft bonded to the aromatic polymer. 22. A composition for forming an elastomeric material, comprising an aromatic polymer that is non-elastomeric at room temperature; anda cross-linking compound, wherein the cross-linking compound and the aromatic polymer can react to form a cross-linked aromatic polymer that becomes elastomeric when heated at or above a glass transition temperature of the cross-linked aromatic polymer, and the cross-linking compound has a structure according to formula (II): wherein A is an arene moiety having a molecular weight of less than 10,000 g/mol, R1 is selected from a group consisting of hydroxide (—OH) amine (—NH2), halide, ether, ester, or amide, and x is about 2.0 to about 6.0. 23. A method of using an organic polymer that is not elastomeric at room temperature in an elastomeric application, comprising cross-linking the organic polymer using a cross-linking compound to form a cross-linked organic polymer to substantially cure the aromatic polymer, wherein the cross-linking compound has as structure according to formula(II): wherein A is an arene moiety having a molecular weight of less than 10 000 g/mol, R1 is selected from a group consisting of hydroxide (—OH), amine (—NH2), halide, ether, ester, or amide, and x is about 2.0 to about 6.0; and heating the cross-linked polymer in use at or above a glass transition temperature of the cross-linked polymer such that it becomes elastomeric. 24. The method of using an organic polymer in an elastomeric composition according to claim 23, further comprising forming a composition comprising the cross-linked organic polymer, molding the composition into a molded article, placing the molded article in use and heating the molded article in use so as to heat the cross-linked polymer at or above the glass transition temperature of the cross-linked polymer. 25. A method of preparing an elastomeric material, comprising (a) providing an aromatic polymer which is non-elastomeric at room temperature;(b) cross-linking the aromatic polymer using a cross-linking compound to form a cross-linked aromatic polymer, wherein the cross-linking compound has a structure according to formula (II): wherein A is an arene moiety having a molecular weight of less than 10,000 g/mol, R1 is selected from a group consisting of hydroxide (—OH), amine (—NH2), halide, ether, ester, or amide, and x is about 2.0 to about 6.0; and (c) heating the cross-linked aromatic polymer to a temperature at or above a glass transition temperature of the cross-linked aromatic polymer. 26. The method of preparing an elastomeric material according to claim 25, wherein, in step (b), the aromatic polymer is at least about 80% cured. 27. The method of preparing an elastomeric material according to claim 26, wherein the aromatic polymer is at least about 90% cured. 28. The method of preparing an elastomeric material according to claim 27, wherein the aromatic polymer is fully cured. 29. A method of preparing an elastomeric material according to claim 25, wherein the aromatic polymer is selected from the group consisting of poly(arylene ether)s, polysulfones, polyethersulfones, polyarylene sulfides, polyimides, polyamides, polyureas, polyurethanes, polyphthalamides, polyamide-imides, poly(benzimidazole)s, polyarylates, liquid crstalline polymers (LCPs) and polyaramids. 30. The method of preparing an elastomeric material according to claim 29, wherein the aromatic polymer is a poly(arylene ether) including polymer repeating units having the following structure: —(—O—Ar1—O—Ar2—)m(—O—Ar3—O—Ar4—)n— wherein Ar1, Ar2, Ar3 and Ar4 are identical or different aryl radicals, m=0 to 1.0, and n=1 m. 31. The method of preparing an elastomeric material according to claim 30, wherein step (b) further comprises cross-linking the organic polymer with the cross-linking compound and a cross-linking reaction additive selected from an organic acid and/or an acetate compound, wherein the cross-inking reaction additive is capable of reacting with the cross-linking compound to form a reactive intermediate in the form of an oligomer, which reactive intermediate oligomer is capable of cross-linking the organic polymer. 32. The method of preparing an elastomeric material according to claim 31, wherein the cross-linking reaction additive is an organic acid selected from glacial acetic acid, formic acid, and/or benzoic acid. 33. The method of preparing an elastomeric material according to claim 31, wherein the cross-linking reaction additive is an acetate compound having a structure according to formula (XI): wherein M is a Group I or a Group II metal; and R2 is a alkyl, aryl or aralkyl group, wherein the alkyl group comprises a hydrocarbon group of 1 to about 15 carbon atoms which has from 0 to about 5 ester or ether groups along or in a chain of the hydrocarbon group, and wherein R2 comprises 0 to about 5 functional groups selected from sulfate, phosphate, hydroxyl, carbonyl, ester, halide, mercapto or potassium. 34. The method of preparing an elastomeric material according to claim 33, wherein the acetate compound is selected from lithium acetate hydrate sodium acetate, and/or potassium acetate, and salts and derivatives thereof. 35. The method of preparing an elastomeric material according to claim 31, wherein the weight percentage ratio of the cross-linking compound to the cross-linking reaction additive is about 10:1 to about 10,000:1. 36. The method of preparing an elastomeric material according to claim 35, wherein the weight percentage ratio of the cross-linking compound to the cross-linking reaction additive is about 20:1 to about 1000:1. 37. The method of preparing an elastomeric material according to claim 30, wherein the organic polymer is a poly(arylene ether), m is 1 and n is 0 and the polymer has repeating units having the structure of formula (I): 38. The method of preparing an elastomeric material according to claim 25, wherein the cross-linking compound has a structure selected from a group consisting of 39. The method of preparing an elastomeric material according to claim 25, wherein the arene moiety has a molecular weight of about 1,000 g/mol to about 9,000 g/mol. 40. The method of preparing an elastomeric material according to claim 39, wherein the arene moiety has a molecular weight of about 2,000 g/mol to about 7,000 g/mol. 41. The method of preparing an elastomeric material according to claim 25, wherein the method further comprises forming a composition comprising the cross-linked organic polymer and heating the composition to form a molded article and step (c) further comprises placing the molded article in use at a temperature at or above the glass transition temperature of the cross-linked organic polymer. 42. An article formed by the method of claim 25. 43. The article according to claim 42, selected from the group consisting of an O-ring, a V-ring, a U-cup, a gasket, at least one component of a seal stack, a packer element, a diaphragm, a face seal, a bearing, a valve seat, an adapter, a wiper ring, a chevron seal back-up ring, an tubing.
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