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US 5,548,051 AGranted
Single component inorganic/organic network materials and precursors thereof
AssigneeE. I. Du Pont de Nemours and Company
InventorsMichael J. Michalczyk, Kenneth G. Sharp
Life of this patent
Estimating the term…
Abstract
Single component inorganic/organic network materials incorporating the physical properties of glasses with the flexibility of organic materials of empirical formula X(SiO.sub.1.5).sub.n wherein X is one or more flexible organic linkages and n is greater than or equal to 2, as well as precursors thereof, are disclosed.
Claims14
A compound of the formula (I):
- X(SiQ.sub.3).sub.n (I)
- wherein:
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- and
- X is at least one flexible organic link selected from the group consisting of:
- (a) R.sup.1.sub.m SiY.sub.4-m ;
- (b) R.sup.1.sub.m Si(OSi(CH.sub.3).sub.2 Y).sub.4-m ;
- (c) R.sup.1.sub.m Si(OY).sub.4-m ;
- (d) CH.sub.3 SiY.sub.2 --O--SiY.sub.2 CH.sub.3 ;
- (e) O[--C.sub.6 H.sub.4 --Si(CH.sub.3).sub.2 Y].sub.2 ;
- (f) Y(CH.sub.3).sub.2 SiCH.sub.2 --CH.sub.2 Si(CH.sub.3).sub.2 Y;
- (g) Y(CF.sub.2).sub.p Y, provided that Y is other than ethylene;
- (h) Y.sub.3 SiOSiY.sub.3 ;
- (i) Y.sub.3 Si(CH.sub.2).sub.b SiY.sub.3 ;
- (j) Y.sub.3 SiC.sub.6 H.sub.4 SiY.sub.3 ;
- (k) substituted benzene selected from the group consisting of:
- (i) C.sub.6 H.sub.3 (SiZ.sub.3-a Y.sub.a).sub.3 ;
- (ii) C.sub.6 H.sub.2 (SiZ.sub.3-a Y.sub.a).sub.4 ;
- (iii) C.sub.6 H(SiZ.sub.3-a Y.sub.a).sub.5 ;
- and
- (iv) C.sub.6 (SiZ.sub.3-a Y.sub.a).sub.6 ;
- and
- (l) substituted cyclohexane selected from the group consisting of:
- (i) 1,2-C.sub.6 H.sub.10 (Y).sub.2 ;
- 1,3-C.sub.6 H.sub.10 (Y).sub.2 ;
- 1,4-C.sub.6 H.sub.10 (Y).sub.2
- (ii) 1,2,4-C.sub.6 H.sub.9 (Y).sub.3 ;
- 1,2,3-C.sub.6 H.sub.9 (Y).sub.3 ;
- 1,3,5-C.sub.6 H.sub.9 (Y).sub.3 ;
- (iii) 1,2,3,4-C.sub.6 H.sub.8 (Y).sub.4 ;
- 1,2,4,5-C.sub.6 H.sub.8 (Y).sub.4 ;
- 1,2,3,5-C.sub.6 H.sub.8 (Y).sub.4 ;
- (iv) 1,2,3,4,5-C.sub.6 H.sub.7 (Y).sub.5 ;
- and
- (v) C.sub.6 H.sub.6 (Y).sub.6 ;
- wherein:
- Z is an alkyl group of 1 to 4 carbon atoms, 3,3,3-trifluoropropyl, aralkyl or aryl;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.1 is alkyl of 1 to about 8 carbon atoms or aryl;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- m is 0, 1 or 2;
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- and
- a is 1, 2 or 3;
- p is an even integer from 4 to 10;
- b is an integer from 1 to 10.
44 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is R.sup.1.sub.m SiY.sub.4-m ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- R.sup.1 is alkyl of 1 to about 8 carbon atoms or aryl;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- m is 0, 1 or 2;
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula R.sup.1.sub.m Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.4-m, or a compound containing an Si--H group having the formula R.sup.1.sub.m SiH.sub.4-m with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
7 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is R.sup.1.sub.m Si(OSi(CH.sub.3).sub.2 Y).sub.4-m ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- R.sup.1 is alkyl of 1 to about 8 carbon atoms or aryl;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- m is 0, 1 or 2;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula R.sup.1.sub.m Si[OSi(CH.sub.3).sub.2 (CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7 ].sub.4-m, or a compound containing an Si--H group having the formula R.sup.1.sub.m Si(OSi(CH.sub.3).sub.2 H).sub.4-m with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
8 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- R.sup.1.sub.m Si(OY).sub.4-m ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- R.sup.1 is alkyl of 1 to about 8 carbon atoms or aryl;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- m is 0, 1 or 2;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula R.sup.1.sub.m Si(O(CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.4-m ;
- in the presence of a transition metal catalyst or free radical initiator.
8 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is CH.sub.3 SiY.sub.2 --O--SiY.sub.2 CH.sub.3 ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula CH.sub.3 Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.2 --O--Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.2 CH.sub.3 or a compound containing an Si--H group having the formula CH.sub.3 SiH.sub.2 --O--SiH.sub.2 CH.sub.3 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is O[--C.sub.6 H.sub.4 --Si(CH.sub.3).sub.2 Y.sub.2 ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k and h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula D((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.2, wherein D is (CH.sub.3).sub.2 SiC.sub.6 H.sub.4 OC.sub.6 H.sub.4 Si(CH.sub.3).sub.2, or a compound containing an Si--H group having the formula DH.sub.2 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is Y(CH.sub.3).sub.2 SiCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.2 Y;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k and h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula D((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.2, wherein D is (CH.sub.3).sub.2 SiCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.2, or a compound containing an Si--H group having the formula DH.sub.2 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is Y(CF.sub.2).sub.p Y;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (R.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- p is an even integer from 4 to 10;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula CR.sup.6 R.sup.7 .dbd.CR.sup.4 (CR.sup.2 R.sup.3).sub.k (CF.sub.2).sub.p (CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7, in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is Y.sub.3 SiOSiY.sub.3 ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3 OSi((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3, or a compound containing an Si--H group having the formula SiH.sub.3 OSiH.sub.3 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is Y.sub.3 Si(CH.sub.2).sub.b SiY.sub.3 ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- b is an integer from 1 to 10;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3 (CH.sub.2).sub.b Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3, or a compound containing an Si--H group having the formula SiH.sub.3 (CH.sub.2).sub.b SiH.sub.3 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
7 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is Y.sub.3 SiC.sub.6 H.sub.4 SiY.sub.3 ;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3 C.sub.6 H.sub.4 Si((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.3, or a compound containing an Si--H group having the formula SiH.sub.3 C.sub.6 H.sub.4 SiH.sub.3 with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
6 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is substituted benzene, C.sub.6 H.sub.6-w (SiZ.sub.3-a Y.sub.a).sub.w, wherein w is the number of substituents;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Z is an alkyl group of 1 to 4 carbon atoms, 3,3,3-trifluoropropyl, aralkyl or aryl;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- m is 0, 1 or 2;
- a is 1, 2 or 3;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula C.sub.6 H.sub.6-w (SiZ.sub.3-a ((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.a).sub.w, or a compound containing an Si--H group having the formula C.sub.6 H.sub.6-w (SiZ.sub.3-a H.sub.a).sub.w with a compound containing a carbon-carbon double bond having the formula CR.sup.4 R.sup.5 .dbd.CR.sup.6 (CR.sup.8 R.sup.9).sub.h SiQ.sub.3 ;
- in the presence of a transition metal catalyst or free radical initiator.
10 more elements
A process for the preparation of a compound having the formula X(SiQ.sub.3).sub.n, wherein:
- X is substituted cyclohexane, C.sub.6 H.sub.12-w (Y).sub.w, wherein w is the number of substituents;
- Q is alkoxy of 1 to about 8 carbon atoms, acyloxy of 1 to about 8 carbon atoms, or halogen;
- n is an integer greater than or equal to 2;
- Y is --(CR.sup.2 R.sup.3).sub.k CR.sup.4 R.sup.5 CR.sup.6 R.sup.7 (CR.sup.8 R.sup.9).sub.h --;
- R.sup.2 to R.sup.9 are each independently hydrogen, alkyl of 1 to about 8 carbon atoms or aryl, provided that at least one of R.sup.4 to R.sup.7 is hydrogen;
- and
- k and h are each independently an integer from 0 to 10, provided that at least one of k or h is zero;
- comprising reacting a compound containing an Si--H group having the formula HSiQ.sub.3, with a compound containing a carbon-carbon double bond having the formula C.sub.6 H.sub.12-w ((CR.sup.2 R.sup.3).sub.k CR.sup.4 .dbd.CR.sup.6 R.sup.7).sub.w in the presence of a transition metal catalyst or free radical initiator.
5 more elements
Dependencies are inferred from the claim text.