US5015700A
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Anhydride-functional organo/(poly)siloxanes, a process for preparing the same and uses thereof
Assignee: Wacker Chemie AG
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Filing: 1990-08-06
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Granted: 1991-05-14
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Expires: 2010-08-06
Abstract
Abstract Anhydride-functional organo(poly)siloxanes having average units of the general formula ##EQU1## in which the R(s) are the same or different and represent a monovalent hydrocarbon radical or a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A represents a radical of the formula ##STR1## in which R 1 represents a hydrogen atom or a monovalent hydrocarbon radical or a monovalent halogenated hydrocarbon radical having from 1 to 12 carbon atom(s) per radical and R 2 represents a hydrogen atom or a monovalent hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, or the two radicals R and R 2 together represent a divalent hyrocarbon radical having from 3 to 5 carbon atoms per radical, R 3 represents a hydrogen atom or a monovalent hydrocarbon radical having from 1 to 4 carbon atom(s) per radical, with the proviso that R 3 is a hydrogen atom if the two radicals R 1 and R 2 together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 4 , which may be the same or different, represent a hydrogen atom, a halogen atom or a cyano radical, a is 0 or 1, with an average of from 0.003 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.05 to 2.5, and the sum of a+b is an average which is not greater than 3, with the proviso that at least one A radical is present per molecule.
Inventors
- 👤 Christian Herzig
- 👤 Josef Esterbauer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:00
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/20; C08G77/14; C08G77/38
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
271 words
An anhydride-functional organo(poly)siloxane having average units of the general formula ##EQU4## in which the R(s) are selected from the group consisting of a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A is a radical selected from the group consisting of the formulas ##STR18## mixtures thereof, in which R 1 is selected from the group consisting of a hydrogen atom, a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, R 2 is selected from the group consisting of a hydrogen atom, and a monovalent hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, or the radicals R 1 and R 2 together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 3 is selected from the group consisting of a hydrogen atom and a monovalent hydrocarbon radical having from 1 to 4 carbon atom(s) per radical, with the proviso that R 3 is a hydrogen atom when the R 1 and R 2 radicals together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 4 is selected from the group consisting of a hydrogen atom, a halogen atom and a cyano radical, a is 0 or 1, with an average of from 0.003 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.05 to 2.5, and the sum of a+b is an average which is not greater than 3, with the proviso that at least one radical A is present per molecule.
Claim 2
Dependent Claim
271 words
An anhydride-functional organo(poly)siloxane having average units of the general formula ##EQU4## in which the R(s) are selected from the group consisting of a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A is a radical selected from the group consisting of the formulas ##STR18## mixtures thereof, in which R 1 is selected from the group consisting of a hydrogen atom, a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, R 2 is selected from the group consisting of a hydrogen atom, and a monovalent hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, or the radicals R 1 and R 2 together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 3 is selected from the group consisting of a hydrogen atom and a monovalent hydrocarbon radical having from 1 to 4 carbon atom(s) per radical, with the proviso that R 3 is a hydrogen atom when the R 1 and R 2 radicals together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 4 is selected from the group consisting of a hydrogen atom, a halogen atom and a cyano radical, a is 0 or 1, with an average of from 0.003 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.05 to 2.5, and the sum of a+b is an average which is not greater than 3, with the proviso that at least one radical A is present per molecule.
Claim 3
Dependent Claim
26 words
The anhydride-functional organo(poly)siloxane of claim 1, wherein R 1 is a methyl radical and R 2 , R 3 and R 4 are each hydrogen atoms.
Claim 4
Dependent Claim
275 words
The anhydride-functional organo(poly)siloxane of claim 1, which has the general formula A.sub.d R.sub.3-d SiO(SiR.sub.2 O).sub.n (SiRAO).sub.m SiR.sub.3-d A.sub.d(II) in which the R(s) are selected from the group consisting of a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A is a radical selected from the group consisting of the formulas ##STR19## and mixtures thereof, in which R 1 is selected from the group consisting of a hydrogen atom, a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, R 2 is selected from the group consisting of a hydrogen atom, and a monovalent hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, or the radicals R 1 and R 2 together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 3 is selected from the group consisting of a hydrogen atom and a monovalent hydrocarbon radical having from 1 to 4 carbon atom(s) per radical, with the proviso that R 3 is a hydrogen atom if the R 1 and R 2 radicals together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 4 is selected from the group consisting of a hydrogen atom, a halogen atom and a cyano radical, d is 0 or 1, n is 0 or an integer of from 1 to 1,500 and m is 0 or an integer of from 1 to 200, with the proviso that at least one radical A is present per molecule and the ratio of n:m is not greater than 200.
Claim 5
Dependent Claim
24 words
The anhydride-functional organo(poly)siloxane wherein R 1 is a methyl radical and R 2 , R 3 and R 4 are each a hydrogen atom.
Claim 6
Dependent Claim
24 words
The anhydride-functional organo(poly)siloxane wherein R 1 is a methyl radical and R 2 , R 3 and R 4 are each a hydrogen atom.
Claim 7
Dependent Claim
128 words
A process for preparing the anhydride-functional organo(poly)siloxane of claim 1, which comprises in a first stage, reacting an acetylenic alcohol selected from the group consisting of a secondary and tertiary acetylenic alcohol (1) with an organo(poly)siloxane (2) having at least one Si-linked hydrogen atom in the presence of a catawith (3) which promotes the addition of Si-linked hydrogen to an aliphatic multiple bond, and then in a 2nd stage, reacting the alkenol groups of the organo(poly)siloxane obtained in the 1st stage with an anhydride selected from the group consisting of maleic anhydride and a substituted maleic anhydride, in which the elements of water are eliminated by an intramolecular reaction from the alkenol groups and the anhydride is then added on thereto in the manner of a Diels-Alder reaction.
Claim 8
Dependent Claim
32 words
The process of claim 5, wherein the reaction between the alkenol groups of the organo(poly)siloxane obtained in the first stage with the anhydride is conducted in the presence of an acid catalyst.
Claim 9
Dependent Claim
48 words
The process of claim 5, wherein the anhydride-functional organo(poly)siloxane obtained from the 2nd stage is equilibrated with an organo(poly)siloxane (4) selected from the group consisting of linear organo(poly)siloxanes containing terminal triorganosiloxy groups, linear organo(poly)siloxanes containing terminal hydroxyl groups, cyclic organo(poly)siloxanes and copolymers formed from diorganosiloxane and monoorganosiloxane units.
Claim 10
Dependent Claim
18 words
The process of claim 7, wherein the equilibrated process is conducted in the presence of an acid catalyst.
Claim 11
Dependent Claim
163 words
The process of claim 5, wherein the acetylenic alcohol (1) is an acetylenic alcohol of the general formula HC.tbd.C--C(OH)R.sup.1 --CHR.sup.2 R.sup.3, in which R 1 is selected for the group consisting of a hydrogen atom, a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, R 2 is selected from the group consisting of a hydrogen atom, and a monovalent hydrocarbon radical having from 1 to 12 carbon atom(s) per radical, or the radicals R 1 and R 2 together represent a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical, R 3 is selected from the group consisting of a hydrogen atom and a monovalent hydrocarbon radical having from 1 to 4 carbon atom(s) per radical, with the proviso that R 3 is a hydrogen atom if the two radicals R 1 and R 2 together represents a divalent hydrocarbon radical having from 3 to 5 carbon atoms per radical.
Claim 12
Dependent Claim
12 words
The process of claim 5, wherein the acetylenic alcohol (1) is 2-methyl-3-butyn-2-ol.
Claim 13
Dependent Claim
86 words
A process for preparing organopolysiloxane/polyimide copolymers which comprises reacting the anhydride-functional organo(poly)siloxane of claim 1 with an organic diamine of the formula NH.sub.2 R.sup.5 NH.sub.2 in which R 5 is selected from the group consisting of a divalent hydrocarbon radical having from 2 to 15 carbon atoms per radical and a divalent radical of the formula ##STR20## in which R 6 is selected from the group consisting of ##STR21## --S-- and C x H 2x , where x is an integer of from 1 to 5.
Claim 14
Dependent Claim
138 words
The process of claim 11, wherein the anhydride-functional organo(poly)siloxane has average units of the general formula ##EQU5## in which the R(s) are selected from the group consisting of a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A is a radical selected from the group consisting of the formulas ##STR22## mixtures thereof, in which R 1 is a methyl radical and R 2 , R 3 and R 4 are each hydrogen atoms, a is 0 or 1, with an average of from 0.003 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.05 to 2.5 an the sum of a+b is an average which is not greater than 3, with the proviso that at least one radical A is present per molecule.
Claim 15
Dependent Claim
22 words
A process for forming a curable epoxy resin, which comprises mixing the anhydride-functional organo(poly)siloxane of claim 1, with a heat-curable epoxy resin.
Claim 16
Dependent Claim
138 words
The process of claim 13, wherein the anhydride-functional organo(poly)siloxane has average units of the general formula ##EQU6## in which the R(s) are selected from the group consisting of a monovalent hydrocarbon radical and a monovalent halogenated hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, A is a radical selected from the group consisting of the formulas ##STR23## mixtures thereof, in which R 1 is a methyl radical and R 2 , R 3 and R 4 are each hydrogen atoms, a is 0 or 1, with an average of from 0.003 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.05 to 2.5 and the sum of a+b is an average which is not greater than 3, with the proviso that at least one radical A is present per molecule.
Claim 17
Dependent Claim
14 words
A cured epoxy resin which is obtained by heating the mixture of claim 13.
Claim 18
Dependent Claim
14 words
A cured epoxy resin which is obtained by heating the mixture of claim 14.
References Cited (Backward Citations)
EP0176085A2
Cited
US4923948A
Cited
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