Polydiorganosiloxane oligourea segmented copolymers and a process for making same
First Claim
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1. Polydiorganosiloxane oligourea segmented copolymers comprising (i) a pair of soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue unit is a polydiorganosiloxane amine minus all —
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) a single hard polyisocyanate residue unit, wherein the polyisocyanate residue unit is a polyisocyanate minus the —
NCO groups, (iii) urea linkages connecting the isocyanate residue unit and the polydiorganosiloxane amine residue units, and (iv) terminal groups that are not reactive under moisture curing or free radical curing conditions and are not a reactive amine or a reactive isocyanate.
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Abstract
The present invention provides polydiorganosiloxane oligourea segmented copolymers. The copolymers contain soft polydiorganosiloxane units, hard segments that are diisocyanate residues, the polydiorganosiloxane units and diisocyanate residues being connected by urea linkages, and terminal groups that are non-reactive, reactive under free radical or moisture cure conditions, or amines. The invention also provides methods of preparing the copolymers.
129 Citations
40 Claims
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1. Polydiorganosiloxane oligourea segmented copolymers comprising (i) a pair of soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue unit is a polydiorganosiloxane amine minus all —
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) a single hard polyisocyanate residue unit, wherein the polyisocyanate residue unit is a polyisocyanate minus the —
NCO groups, (iii) urea linkages connecting the isocyanate residue unit and the polydiorganosiloxane amine residue units, and (iv) terminal groups that are not reactive under moisture curing or free radical curing conditions and are not a reactive amine or a reactive isocyanate. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) a single hard polyisocyanate residue unit, wherein the polyisocyanate residue unit is a polyisocyanate minus the —
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16. Poyldiorganosiloxane oligourea segmented copolymer comprising the reaction product of:
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(a) a polyisocyanate; and
(b) a polydiorganosiloxane monoamine having a first terminal portion reactive with an isocyanate and a second terminal portion that is not reactive under moisture curing or free radical curing conditions and is not a reactive amine or a reactive isocyanate.
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17. A process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) providing reactants, wherein the reactants comprise (i) a polyisocyanate, (ii) a polydiorganosiloxane monoamine having a first terminal portion that is an amine and a second terminal portion that is not reactive under moisture curing or free radical curing conditions and is not a reactive amine or a reactive isocyanate, and (iii) solvent, to a reactor;
(b) mixing the reactants in the reactor;
(c) allowing the reactants to react to form a polydiorganosiloxane oligourea segmented copolymer having (i) a single hard polisocyanate residue unit, wherein the polyisocyanate residue unit is the polyisocyanate minus the —
NCO groups, (ii) a pair of soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are the polydiorganosiloxane monamine minus the —
NDH group with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, and (iii) urea linkage connecting the isocyanate residue unit and the polydiorganosiloxane amine residue units; and
(d) conveying the oligomer from the reactor.
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18. An essentially solventless process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) continuously providing reactants to a reactor under substantially solventless conditions, wherein the reactants comprise (i) a polyisocyanate, and (ii) a polydiorganosiloxane monoamine having a first terminal portion that is an amine and a second terminal portion that is not reactive under moisture curing or free radical curing conditions and is not a reactive amine or a reactive isocyanate;
(b) mixing the reactants in the reactor under the substantially solventless conditions;
(c) allowing the reactions to react to form a polydiorganosiloxane oligourea segmented copolymer having (i) a single hard polyisocyanate residue unit, wherein the polyisocyanate residue unit is the polyisocyanate minus the —
NCO groups, (ii) a pair of soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are the polydiorganosiloxane monoamine minus the —
NDH group with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, and (iii) urea linkage connecting the isocyanate residue unit and the polydiorganosiloxane amine residue units; and
(d) conveying the oligomer from the reactor.
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19. Polydiorganosiloxane oligourea segmented copolymers comprising (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are the polydiorganosiloxane amine minus all —
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) Hard polyisocyanate residue units, wherein the polyisocyanate residue units are the polyisocyanate minus the —
NCO groups, (iii) moisture curable monoisocyanate residue terminal units, wherein the moisture curable monoisocyanate residue terminal units are the monoisocyanate minus the —
NCO group and the moisture curable monoisocyanate residue terminal units are selected from the group consisting of propyl trimethoxysilane, propyl triethoxysilane, propyl dimethoxy (methylethylketoximino)silane, propyl diethoxy (methylethylketoximino)silane, propyl monomethoxy di(methylethylketoximino)silane, propyl monoethoxy di(methylethylketoximino) silane, and propyl tri(methylethylketoximino)silane, and (iv) urea linkages connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the moisture curable terminal groups. - View Dependent Claims (20, 21, 22, 23, 24, 25)
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) Hard polyisocyanate residue units, wherein the polyisocyanate residue units are the polyisocyanate minus the —
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26. Polydiorganosiloxane oligurea segmented copolymer comprising the reaction product of:
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(a) at least one polyisocyanate;
(b) at least one polydiorganosiloxane diamine; and
(c) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion reactive with an amine, and a second terminal portion that can react under moisture-cure conditions.
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27. A process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) providing reactants to a reactor, wherein the reactants comprise (i) at least one polyisocyanate, (ii) at least one polydiorganosiloxane diamine, and (iii) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion of an —
NCO group, and a second terminal portion that can react under moisture-cure conditions selected from the group consisting of propyl trimethoxysilane, propy triethoxysilane, propyl dimethoxy (methylethylketoximino)silane, propyl diethoxy (methylethylketoximino)silane, propyl monomethoxy di(methylethylketoximino)silane, propyl monoethoxy di(methylethylketoximino) silane, and propyl tri(methylthylketoximino)silane, and (iv) solvent;
(b) mixing the reactants in the reactor;
(c) allowing the reactants to react to form a polydiorganosiloxane oligourea segmented copolymer having (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are the polydiorganosiloxane amine minus all —
NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are the polysisocyanate minus the —
NCO groups, (iii) endcapping agent residue units wherein the endcapping agent residue units are the endcapping agent minus the —
NCO group, and (iv) urea linkages connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the endcapping agent residue units; and
(d) conveying the oligomer from the reactor.
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28. An essentially solventless process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) continuously providing reactants to a reactor under substantially solventless conditions, wherein the reactants comprise (i) at least one polyisocyanate, (ii) at least one polydiorganosiloxane diamine, and (iii) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion of an —
NCO group, and a second terminal portion that can react under moisture-cure conditions;
(b) mixing the reactants in the reactor under the substantially solventless conditions;
(c) allowing the reactants to react to form a polydiorganosiloxane oligourea segmented copolymer having (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are the polydiorganosiloxane amine minus all —
NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are the polyisocyanate minus the —
NCO groups, (iii) endcapping agent residue units wherein the endcapping agent residue units are the endcapping agent minus the —
NCO group, and (iv) urea linkages connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the endcapping agent residue units; and
(d) conveying the oligomer from the reactor.
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29. Polydiorganosiloxane oligourea segmented copolymers comprising (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are a polydiorganosiloxane amine minus all —
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are a polyisocyanate minus the —
NCO groups, (iii) monoamine residue terminal units having an endcapping group, wherein the monoamine residue terminal units are a monamine minus the —
NDH group with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, and (iv) urea linkage connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the monoamine residue terminal units, wherein the monamine residue terminal units are connected through the —
NDH group on the monoamine. - View Dependent Claims (30, 31, 32, 33, 34, 35, 36, 37)
- NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are a polyisocyanate minus the —
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38. Polydiorganosiloxane oligourea segmented copolymer comprising the reaction product of:
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(a) at least one polyisocyanate;
(b) at least one polydiorganosiloxane diamine; and
(c) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion reactive with an isocyanate, and a second terminal portion selected from the group consisting of (i) a moiety that is not reactive under moisture curing or free radical curing conditions selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl, (ii) a free radically curable end group, or (iii) a moisture curable group selected from the group consisting of propyl trimethoxysilane, propyl triethoxysilane, propyl methyldimethoxysilane, propyl methyldiethoxysilane, propyl dimethoxy (methylethylketoximino)silane, propyl diethoxy (methylethylketoximino)silane, propyl monomethoxydi(methylethylketoximino)silane, propyl monoethoxydi(methylethylketoximino)silane, and propyl tri(methylethylketoximono)silane, mixtures thereof and partial hydrolyzates thereof.
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39. A process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) providing reactants to a reactor, wherein the reactants comprise (i) at least one polyisocyanate, (ii) at least one polydiorganosiloxane diamine, and (iii) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion reactive with an isocyanate, and a second terminal portion selected from the group consisting of (A) a moiety that is not reactive under moisture curing or free radical curing conditions selected from the group consisting or alkyl, substituted alkyl, aryl, and substituted aryl (B) a free radically curable end group, or (C) a moisture curable group selected from the group consisting of propyl trimethoxysilane, propyl triethoxysilane, propyl methyldimethoxysilane, propyl methyldiethoxysilane, propyl dimethoxy (methylethylketoximino)silane, propyl diethoxy (methylethylketoximino)silane, propyl monomethoxydi(methylethylketoximino)silane, propyl monoethoxydi(methylethylketoximino)silane, and propyl tri(methylethylketoximino)silane mixtures thereof and partial hydrolyzates thereof, and (iv) solvent;
(b) mixing the reactants in the reactor;
allowing the reactants to react to form a polydioganosiloxane oligourea segmented copolymer having (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are a polydiorganosiloxane amine minus all —
NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are a polyisocyanate minus the —
NCO groups, (iii) monoamine residue terminal units, wherein the monoamine residue terminal units are a amonoamine minus the —
NDH group with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, and the monoamine residue terminal units have an endcapping group, and (iv) urea linkages connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the monoamine residue terminal units, wherein the monoamine residue terminal units are connected through the —
NDH group on the monoamine; and
(d) conveying the oligomer from the reactor.
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40. an essentially solventless process for preparing polydiorganosiloxane oligourea segmented copolymers comprising the steps of:
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(a) continuously providing reactants to a reactor under substantially solventless conditions, wherein the reactants comprise (i) at least one polyisocyanate, (ii) at least one polydiorganosiloxane diamine, and (iii) at least one non-siloxane containing endcapping agent wherein the endcapping agent has a first terminal portion reactive with an isoyanate, and a second terminal portion selected from the group consisting of (A) a moiety that is not reactive under moisture curing or free radical curing conditions selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl, (B) a free radically curable end group, or (C) a moisture curable group selected from the group cosisting of propyl trimethoxysilane, propyl triethoxysilane, propyl methyldimethoxysilane, propyl methyldiethoxysilane, proply dimethoxy (methylethylketoximino)silane, propyl diethoxy (methylethylketoximino)silane, propyl monomethoxydi(methylethylketoximino)silane, propyl monoethoxydi(methylethylketoximino)silane, and propyl tri(methylethylketoximino)silane mixtures thereof and partial hydrolyzates thereof;
(b) mixing the reactants in the reactor under the substantially solventless conditions;
(c) allowing the reactants to react to form a polydiorganosiloxane oligourea segmented copolymer having (i) soft polydiorganosiloxane amine residue units, wherein the polydiorganosiloxane amine residue units are a polydiorganosiloxane amine minus all —
NDH groups with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to from a hetercycle having about 6 to 20 carbon atoms, (ii) hard polyisocyanate residue units, wherein the polyisocyanate residue units are a polyisocyanate minus the —
NCO groups, (iii) monoamine residue terminal units, wherein the monoamine residue terminal units are a monoamine minus the —
NDH group with D selected from hydrogen, alkyl radicals having 1 to 10 carbon atoms, phenyl and a radical that completes a ring structure to form a heterocycle having about 6 to 20 carbon atoms, and the monoamine residue terminal units have an endcapping group, and (iv) urea linkages connecting the isocyanate residue units, the polydiorganosiloxane amine residue units and the monoamine residue terminal units, wherein the monoamine residue terminal units are connected through the —
NDH group on the monoamine; and
(d) conveying the oligomer from the reactor.
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Specification