Thermoset and ceramic containing silicon and boron
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-079/08
C08G-077/56
C04B-035/00
출원번호
US-0254938
(2002-09-26)
발명자
/ 주소
Keller, Teddy M.
Son, David Y.
출원인 / 주소
The United States of America as represented by the Secretary of the Navy
대리인 / 주소
Hunnius Stephen T.
인용정보
피인용 횟수 :
3인용 특허 :
25
초록▼
A thermoset polymer has a repeating unit comprising at least one crosslinking group having at least one unsaturated carbon-carbon bond and at least two crosslinking bonds, at least one borate group, at least one silyl group and/or at least one siloxyl group. The thermoset polymer of the present inve
A thermoset polymer has a repeating unit comprising at least one crosslinking group having at least one unsaturated carbon-carbon bond and at least two crosslinking bonds, at least one borate group, at least one silyl group and/or at least one siloxyl group. The thermoset polymer of the present invention may be prepared by reacting a first compound having at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, with a second compound selected from boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid under reaction conditions sufficient to crosslink a sufficient number of alkyne bonds to form the thermoset polymer. The thermoset polymer of the present invention possesses both the processability of an organic polymer and the thermal and oxidative stability of an inorganic polymer. The thermoset polymer of the present invention may be further processed into a ceramic material by pyrolysis.
대표청구항▼
1. A thermoset polymer produced by reacting a first compound comprising at least one alkynyl group and at least one group selected from silyl groups and siloxyl groups, with a second compound selected from boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid under reaction co
1. A thermoset polymer produced by reacting a first compound comprising at least one alkynyl group and at least one group selected from silyl groups and siloxyl groups, with a second compound selected from boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid under reaction conditions sufficient to crosslink a sufficient number of alkyne bonds to produce a thermoset. 2. A thermoset polymer as claimed in claim 1, wherein said first compound comprises at least two repeating units comprising at least one alkynyl group and at least one siloxyl group. 3. A thermoset polymer as claimed in claim 1, wherein said first compound is a poly (siloxane-acetylene) and said second compound is boric acid. 4. A thermoset polymer as claimed in claim 1, wherein one said reaction condition is a reaction temperature of at least 150° C. 5. A thermoset polymer as claimed in claim 1, wherein said first compound and said second compound are combined at a weight ratio of between 1:1 and 400:1, respectively. 6. A thermoset polymer as claimed in claim 1, wherein said first compound and said second compound are combined at a weight ratio of between 5:1 and 10:1, respectively. 7. A thermoset polymer as claimed in claim 1, wherein said thermoset polymer comprises a repeating unit represented by the formula:wherein:(1) m, n and y are independently selected from positive integers; z is selected from zero or positive integers;(2) R 1 , R 2 , R 3 , and R 4 , are independently selected from a hydrocarbon group, hydrogen, a silane group, and a siloxane group;(3) R 5 is selected from the group-consisting of —OH, a hydrocarbon group, a siloxane group, and a repeating unit of the formula of the poly(siloxane acetylene);(4) R 6 is OR 5 or a hydrocarbon group; and(5) Ae is a group with at least one unsaturated carbon-carbon bond and at least two crosslinking bonds. 8. A thermoset polymer as claimed in claim 7, wherein m and n are positive integers, and z is one. 9. A thermoset polymer as claimed in claim 7,wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of:a haloalkyl group having up to 20 carbon atoms,a haloaryl group having up to 20 carbon atoms,an alkyl, aryl, arylalkyl, or alkylaryl hydrocarbon group having up to 20 carbon atoms, and hydrogen;and wherein R 5 is a repeating unit of the formula of the poly(siloxane acetylene). 10. A thermoset polymer as claimed in claim 7, wherein Ae comprises agroup selected from the group consisting of:and combinations thereof, wherein stands for a crosslinking bond. 11. A thermoset polymer as claimed in claim 7, wherein n is 1. 12. A thermoset polymer as claimed in claim 7, wherein m is 2. 13. A thermoset polymer as claimed in claim 7, wherein said second compound is phenyl boronic acid. 14. A thermoset polymer having a repeating unit comprising at least one crosslinking group having at least one unsaturated carbon-carbon bond and at least two crosslinking bonds, at least one borate group, and at least one group selected from silyl groups and siloxyl groups. 15. A thermoset polymer as claimed in claim 14, wherein said repeating unit further comprises at least one silyl group. 16. A thermoset polymer produced by a method comprising the steps of forming a polymeric composition having a repeating unit comprising at least one alkynyl group, at least one borate group, and at least one group selected from silyl groups and siloxyl groups, and crosslinking said polymeric composition through said at least one alkynyl group. 17. A thermoset polymer as claimed in claim 16, wherein the step of forming said polymeric composition involves reacting a first compound comprising at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, and a second compound selected from the group consisting of boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid. 18. A thermoset polymer as claimed in claim 17, where in said first compound comprises poly(siloxane-acetylene) and said second compound comprises boric acid. 19. A thermoset polymer as claimed in claim 16, wherein the step of crosslinking said polymeric composition further comprises heating said polymeric composition to a temperature sufficient to crosslink an alkyne bond. 20. A thermoset polymer as claimed in claim 16, wherein the step of crosslinking said polymeric composition further comprises the step of irradiating said polymeric composition. 21. A thermoset polymer as claimed in claim 16, wherein said second compound comprises phenyl boronic acid. 22. A method of preparing a thermoset polymer comprising the steps of forming a polymeric having a repeating unit comprising at least one alkynyl group, at least one borate group, and at least one group selected from silyl groups and siloxyl groups, and crosslinking said polymeric composition through said at least one alkynyl group. 23. A method as claimed in claim 22, wherein the step of forming said polymeric composition comprises reacting a first compound comprising at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, with a second compound selected from the group consisting of boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid. 24. A method as claimed in claim 23, wherein said first compound comprises poly(siloxane-acetylene) and said second compound comprises boric acid. 25. A method as claimed in claim 22, wherein the step of crosslinking said polymeric composition further comprises heating said polymeric composition to a temperature sufficient to crosslink an alkyne bond. 26. A method as claimed in claim 22, wherein the step of crosslinking said polymeric composition further comprises the step of irradiating said polymeric composition. 27. A method of preparing a thermoset polymer comprising the step of reacting a first compound comprising at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, with a second compound selected from the group consisting of boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid under reaction conditions sufficient to crosslink a sufficient number of alkyne bonds to form the thermoset polymer. 28. A method as claimed in claim 27, wherein said first compound is a poly (siloxane-acetylene) and said second compound is boric acid. 29. A method as claimed in claim 27, wherein said second compound is phenyl boronic acid. 30. A method as claimed in claim 27, wherein one said reaction condition is a reaction temperature of at least 150° C. 31. A method as claimed in claim 27, wherein said first compound and said second compound are combined at a weight ratio of between 1:1 and 400:1, respectively. 32. A method as claimed in claim 27, wherein said first compound and said second compound are combined at a weight ratio of between 5:1 and 10:1, respectively. 33. A ceramic material made by pyrolyzing a polymer having a repeating unit comprising at least one siloxyl group, at least one crosslinking group having at least one unsaturated carbon-carbon bond and at least two crosslinking bonds, and at least one borate group. 34. A ceramic material as claimed in claim 31, wherein said repeating unit is represented by the formula:wherein:(1) m, n and y are independently selected from positive integers; z is selected from zero or positive integers;(2) R 1 , R 2 , R 3 , and R 4 , are independently selected from a hydrocarbon group, hydrogen, a silane group, and a siloxane group;(3) R 5 is selected from the group consisting of —OH, a hydrocarbon group, a siloxane group, and a repeating unit of the formula of the poly(siloxane acetylene);(4) R 6 is OR 5 or a hydrocarbon group; and(5) Ae is a group with at least one unsaturated carbon-carbon bond and at least two crosslinking bonds. 35. A ceramic material prepared by pyrolyzing a composition comprising a first compou nd including at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, and a second compound selected from the group consisting of boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid. 36. A ceramic material prepared by a method comprising the steps of:forming a thermoset polymer from a first compound comprising at least one alkynyl group, and at least one group selected from silyl groups and siloxyl groups, and a second compound selected from the group consisting of boric acid, hydrocarbon boronic acid, hydrocarbon borate, and pyroboric acid; andpyrolyzing said thermoset polymer.
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이 특허에 인용된 특허 (25)
Reinhardt Bruce A. (Tipp City OH) Bhatt Jayprakash C. (Riverside OH), Acetylenic heterocyclic nonlinear optical thermoset monomers.
Riccitiello Salvatore R. (San Jose CA) Hsu Ming-Ta S. (San Jose CA) Chen Timothy S. (San Jose CA), Boron-containing organosilane polymers and ceramic materials thereof.
Keller Teddy M. (Alexandria VA) Henderson Leslie J. (Alexandria VA), Carborane-(silane or siloxane)-unsaturated hydrocarbon based thermosetting polymers.
Keller Teddy M. (Alexandria VA) Henderson ; Jr. Leslie J. (Alexandria VA), Ceramics formed by pyrolysis of either linear or thermosetting carborane (siloxane or silane) acetylene based precursor.
Schmidt Helmut (Saarbrucken-Gudingen DEX) Kasemann Reiner (Mandelbachtal-Ormesheim DEX) Bruck Stefan (Merchweiler DEX), Coating compositions based on fluorine-containing inorganic polycondensates, their production and their use.
Keller Teddy M. (Alexandria VA) Son David Y. (Alexandria VA), High temperature thermosets and ceramics derived from linear carborane-(siloxane or silane)-acetylene copolymers.
Keller Teddy M. (Alexandria VA) Sundar Raj A. (Basking Ridge NJ), High temperature thermosets/ceramics from novel hybrid copolymer containing random distribution of boranyl, silyl, or si.
Keller Teddy M. ; Houser Eric J., Polymer precursor composition, crosslinked polymers, thermosets and ceramics made with silyl and siloxyl substituted car.
Keller Teddy M. ; Houser Eric J., Polymer precursor composition, crosslinked polymers, thermosets and ceramics made with silyl and siloxyl substituted carboranes with unsaturated organic end groups.
Wolter Herbert (Gerchsheim DEX) Rose Klaus (Kitzingen DEX) Egger Christian (Hchberg DEX), Polymerizable silicic acid heteropolycondensates and their application.
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