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US 6,307,081 B1Granted
Hyperbranched polymers and methods for the preparation, cure, and stabilization thereof
AssigneeDow Corning Silicone Co., Ltd.
InventorsKyosuke Takiuchi, Tadashi Okawa, Stephen Edward Cray, Aziz Muzafarow
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Abstract
This invention relates to a macromonomer and a method for its preparation. The macromonomer has one or more silicon-bonded hydrogen atoms at one molecular chain terminal, and one or more aliphatically unsaturated silicon-bonded organic groups at the other molecular chain terminal. This invention further relates to a method of forming a hyperbranched polymer by polymerizing the macromonomer with a group VIII metal catalyst. The hyperbranched polymers can be used as surfactants, gelling agents, drug delivery systems, and polymeric absorbents.
Claims49
A macromonomer having the general formula:
- wherein each D is independently an aliphatically unsaturated organic group, each R is independently selected from the group consisting of monovalent hydrocarbon groups free of aliphatic unsaturation and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation;
- each R′ is independently selected from the group consisting of monovalent hydrocarbon groups and monovalent halogenated hydrocarbon groups, B is selected from the group consisting of an oxygen atom and a divalent hydrocarbon group having at least two carbon atoms and free of aliphatic unsaturation;
- each X is independently selected from the group consisting of hydroxyl groups, monovalent organosiloxy-groups containing a silicon-bonded functionality selected from the group consisting of a hydrogen atom, alkenyl groups, acryloxy groups, methacryloxy groups, vinylphenyl groups, primary amino groups, and secondary amino groups, and groups of the formula
- wherein s is 0 or 1;
- n is an integer with a value of 1 to 1,001;
- x is 1, 2, or 3;
- m is 0, 1, or 2;
- f is an integer with a value greater than or equal to 0;
- and y is 1, 2, or 3.
6 more elements
A method for synthesizing a macromonomer, wherein the method comprises:
- (1) effecting the ring-opening polymerization of component (C) a cyclic trisiloxane, using component (A) a lithium siloxanolate as polymerization initiator, and
- (2) terminating the ring-opening polymerization with component (D) a terminating agent;
- wherein
- component (A) has the formula
- wherein D is an aliphatically unsaturated organic group;
- each R is independently a monovalent hydrocarbon group free of aliphatic unsaturation;
- each R′ is independently a monovalent hydrocarbon group;
- B is a divalent hydrocarbon group having at least two carbon atoms and free of aliphatic unsaturation;
- m is 0 or 1;
- and p is an integer with a value no greater than 10,
- component (C) has the general formula
- wherein R′ is as described above, and
- component (D) is selected from the group consisting of acids, and halosilyl functional compounds.
10 more elements
A method for synthesizing a macromonomer, wherein the method comprises
- (1) effecting ring-opening polymerization of component (C) a cyclic trisiloxane using component (A) a polymerization initiator
- (2) terminating the ring-opening polymerization with component (D) an acid terminating agent, thereby synthesizing an organopolysiloxane-type polymer in which one molecular chain terminal is blocked by aliphatically unsaturated bond-containing organic groups and the other terminal is blocked by silanol, having the formula
- and thereafter
- (3) reacting the organopolysiloxane-type polymer with component (E), wherein (E) is selected from the group consisting of:
- an amine compound and a hydrolyzable compound;
- wherein
- component (A) is a lithium siloxanolate with the general formula
- wherein each D is independently an aliphatically unsaturated organic group;
- each R is independently selected from monovalent hydrocarbon groups free of aliphatic unsaturation;
- each R′ is independently selected from monovalent hydrocarbon groups;
- B is a divalent hydrocarbon group having at least two carbon atoms and free of aliphatic unsaturation;
- m is 0 or 1;
- n is an integer with a value from 1 to 1,000 that is larger than p, and p is an integer with a value no greater than 10,
- component (C) is a cyclic trisiloxane with the general formula
- wherein R′ is as described above,
- component (D) is a terminating agent selected from the group consisting of acids,
- the amine compound for component (E) is selected from the group consisting of a cyclic silylamine, and an N-substituted cyclic silylamine, and
- the hydrolyzable compound for component (E) is selected from the group consisting of an SiH-functional compound that contains a hydrolyzable silyl group, an alkenyl-functional compound that contains a hydrolyzable silyl group, an acryloxy-functional compound that contains a hydrolyzable silyl group, a methacryloxy-functional compound that contains a hydrolyzable silyl group, and a compound that contains both a vinylphenyl group and a hydrolyzable silyl group.
15 more elements
A method for synthesizing a macromonomer comprising:
- (i) reacting components (a) and (b) to form a product;
- wherein
- component (a) has the formula
- wherein D is an aliphatically unsaturated organic group, each R is independently selected from the group consisting of monovalent hydrocarbon groups free of aliphatic unsaturation and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation;
- f is an integer with a value greater than or equal to 0;
- x is 1, 2, or 3;
- and A is selected from the group consisting of a hydrogen atom, an alkali metal atom, and combinations thereof;
- and
- component (b) has formula
- where R is as defined above;
- B is selected from the group consisting of an oxygen atom and a divalent hydrocarbon group with at least 2 carbon atoms and free of aliphatic unsaturation;
- E is selected from the group consisting of halogen atoms, amino groups, substituted amino groups, and acyloxy groups;
- y is 1, 2, or 3;
- with the provisos that when x is 1, y is 2 or 3 and when y is 1, x is 2 or 3;
- and when E is an amino group or a substituted amino group, A is hydrogen.
12 more elements
A method of preparing a macromonomer, wherein the method comprises
- (I′) reacting components (a′) and (b′);
- wherein
- component (a′) has general formula
- wherein D is an aliphatically unsaturated organic group, each R is independently selected from the group consisting of monovalent hydrocarbon groups free of aliphatic unsaturation and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation;
- n is an integer with a value greater than or equal to 0;
- x is 1, 2, or 3;
- and P is selected from the group consisting of halogen atoms and alkali metal atoms;
- and
- component (b′) has general formula
- where R, is as defined above;
- B is selected from the group consisting of an oxygen atom and a divalent hydrocarbon group with at least 2 carbon atoms and free of aliphatic unsaturation;
- y is 1, 2, or 3, Q is selected from the group consisting of alkali metal atoms and halogen atoms;
- with the provisos that when x is 1,y is 2 or 3;
- when y is 1, x is 2 or 3;
- when P is an alkali metal atom, Q is a halogen atom;
- and when Q is an alkali metal atom, P is a halogen atom.
13 more elements
A method of forming a hyperbranched polymer, wherein the method comprises polymerizing a macromonomer with a catalyst comprising a group VIII metal;
- wherein the macromonomer has the formula
- wherein each D is independently an aliphatically unsaturated organic group, each R is independently selected from the group consisting of monovalent hydrocarbon groups free of aliphatic unsaturation and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation;
- B is selected from the group consisting of an oxygen atom and a divalent hydrocarbon group of at least two carbon atoms and free of aliphatic unsaturation;
- f is an integer with a value greater than or equal to 0;
- x is 1, 2, or 3;
- y is 1, 2, or 3;
- with the provisos that when x is 1, y is 2 or 3 and when y is 1, x is 2 or 3.
4 more elements
Dependencies are inferred from the claim text.