Multifunctional crosslinkers for shape-memory polyimides, polyamides and poly(amide-imides) and methods of making the same
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-211/02
C07C-215/00
C07C-213/02
출원번호
US-0013090
(2013-08-29)
등록번호
US-8962890
(2015-02-24)
발명자
/ 주소
Tan, Loon-Seng
Wang, David Huabin
출원인 / 주소
The United States of America as represented by the Secretary of the Air Force
대리인 / 주소
AFMCLO/JAZ
인용정보
피인용 횟수 :
0인용 특허 :
52
초록
Multifunctional amine crosslinkers that may be used to create crosslinked polyimide, polyamide, and poly(amide-imide) polymers and films having shape memory properties at elevated temperatures and methods of making the same.
대표청구항▼
1. A method for synthesizing a trifunctional crosslinker having the general structure: wherein W is N or B(—O)3, and wherein the amine groups are located meta or para with respect to R, the method comprising the steps of: mixing in a polar, aprotic solvent potassium carbonate, a tris(hydroxyphenyl)
1. A method for synthesizing a trifunctional crosslinker having the general structure: wherein W is N or B(—O)3, and wherein the amine groups are located meta or para with respect to R, the method comprising the steps of: mixing in a polar, aprotic solvent potassium carbonate, a tris(hydroxyphenyl) compound selected from the group consisting of tris(4-hydroxyphenyl)amine and tris(4-hydroxyphenyl)borate, and a halogenated nitrobenzene having the following general structure: wherein X is selected from the group consisting of —F and —Cl; R is selected from the group consisting of —H, —F, —Cl, —CF3, and —CH3; and the nitro group is either meta or para with respect to R, to form a tris(nitrophenoxy)phenyl compound; and reducing the tris(nitrophenoxy)phenyl compound by catalytic hydrogenation in the presence of 5% palladium on activated carbon in a hydrogen atmosphere to form the trifunctional crosslinker. 2. The method of claim 1 wherein W is N, and wherein the trifunctional crosslinker is selected from the group consisting of tris[4-(4-aminophenoxyl)phenyl]amine, tris[4-(2-fluoro-5-aminophenoxy)phenyl]amine, tris[4-(2-fluoro-4-aminophenoxy)phenyl]amine, tris[4-(2-chloro-5-aminophenoxy)phenyl]amine, tris[4-(2-chloro-4-aminophenoxy)phenyl]amine, tris[4-(2-trifluoromethyl-5-aminophenoxy)phenyl]amine, tris[4-(2-trifluoromethyl-4-aminophenoxy)phenyl]amine, tris[4-(2-methyl-5-aminophenoxy)phenyl]amine, and tris[4-(2-methyl-4-aminophenoxy)phenyl]amine. 3. The method of claim 1 wherein W is B(—O)3, and wherein the trifunctional crosslinker is selected from the group consisting of tris[4-(4-aminophenoxyl)phenyl]borate, tris[4-(2-fluoro-5-aminophenoxy)phenyl]borate, tris[4-(2-fluoro-4-aminophenoxy)phenyl]borate, tris[4-(2-chloro-5-aminophenoxy)phenyl]borate, tris[4-(2-chloro-4-aminophenoxy)phenyl]borate, tris[4-(2-trifluoromethyl-5-aminophenoxy)phenyl]borate, tris[4-(2-trifluoromethyl-4-aminophenoxy)phenyl]borate, tris[4-(2-methyl-5-aminophenoxy)phenyl]borate, and tris[4-(2-methyl-4-aminophenoxy)phenyl]borate. 4. A method for synthesizing a trifunctional crosslinker having the general structure: wherein W is P═O and wherein the amine groups are located meta or para with respect to R, the method comprising the steps of: oxidizing tris(4-methoxyphenyl)phosphine with aqueous hydrogen peroxide to form tris(4-methoxyphenyl)phosphine oxide;demethylating the tris(4-methoxyphenyl)phosphine oxide by heating in pyridine hydrochloride to form tris(4-hydroxyphenyl)phosphine oxide;mixing in a polar, aprotic solvent the tris(4-hydroxyphenyl)phosphine oxide, potassium carbonate, and a halogenated nitrobenzene having the following general structure: wherein X is selected from the group consisting of —F and —Cl; R is selected from the group consisting of —H, —F, —Cl, —CF3, and —CH3; and the nitro group is either meta or para with respect to R, to form a tris(nitrophenoxy)phenyl phosphine oxide compound; and reducing the tris(nitrophenoxy)phenyl phosphine oxide compound by catalytic hydrogenation in the presence of 5% palladium on activated carbon in a hydrogen atmosphere to form the trifunctional crosslinker. 5. The method of claim 4 wherein the halogenated nitrobenzene is selected from the group consisting of 1-fluoro-4-nitro-benzene, 1-chloro-4-nitro-benzene, 1,2-difluoro-4-nitro-benzene, 1,2-dichloro-4-nitro-benzene, 1-fluoro-2-methyl-4-nitro-benzene, 1-chloro-2-methyl-4-nitro-benzene, 1-fluoro-2-(trifluoromethyl)-4-nitro-benzene, 1-chloro-2-(trifluoromethyl)-4-nitro-benzene, 1-methyl-2-chloro-4-nitrobenzene, 1-methyl-2-fluoro-4-nitro-benzene, 1-(trifluoromethyl)-2-chloro-4-nitro-benzene, 1-methyl-2-fluoro-4-nitro-benzene. 6. The method of claim 4 wherein the trifunctional crosslinker is selected from the group consisting of tris[4-(4-aminophenoxyl)phenyl]phosphine oxide, tris[4-(2-fluoro-5-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-fluoro-4-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-chloro-5-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-chloro-4-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-trifluoromethyl-5-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-trifluoromethyl-4-aminophenoxy)phenyl]phosphine oxide, tris[4-(2-methyl-5-aminophenoxy)phenyl]phosphine oxide, and tris[4-(2-methyl-4-aminophenoxy)phenyl]phosphine oxide.
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