Patent US4293666A successfully refreshed from Google Patents.
US4293666A
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US
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Organic pigments
Assignee: Hercules LLC
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Filing: 1980-06-23
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Granted: 1981-10-06
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Expires: 2000-06-23
Abstract
Abstract Disclosed are novel organic pigments adapted particularly for use as fillers for paper. The organic pigments are finely divided particles obtained by graft copolymerizing an ethylenically unsaturated monomer, such as styrene, onto a water-soluble cationic prepolymer in an aqueous solution and in the presence of a free-radical polymerization initiator.
Inventors
- 👤 William W. Maslanka
- 👤 Gavin G. Spence
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:27
CPC Classifications
D; D21; D21H; D21H21/00; D21H21/14; D21H21/28; D21H21/285; C; C08; C08F; C08F265/00; C08F265/04; C08F265/10; C08F271/00; D21H17/00; D21H17/20; D21H17/33; D21H17/34; D21H17/41; D21H17/44; D21H17/45; D21H17/455
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
320 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (a) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR20## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR21## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR22## where Y is hydroxyl or halogen, ##STR23## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomers (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 2
Dependent Claim
320 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (a) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR20## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR21## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR22## where Y is hydroxyl or halogen, ##STR23## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomers (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 3
Dependent Claim
300 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (a) being a monomer having the formula ##STR24## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; dially maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR25## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR26## where Y is hydroxyl or halogen, ##STR27## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 4
Dependent Claim
300 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (a) being a monomer having the formula ##STR24## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; dially maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR25## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR26## where Y is hydroxyl or halogen, ##STR27## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 5
Dependent Claim
21 words
The water-insoluble graft copolymer particles of claim 1 wherein monomer (a) is styrene and the monoethylenically unsaturated amide monomer is acrylamide.
Claim 6
Dependent Claim
41 words
The water-insoluble graft copolymer particles of claim 1 wherein monomer (a) is styrene, the monoethylenicaly unsaturated amide monomer is acrylamide, and cationic monomer (i) is selected from the group consisting of methacryloyloxyethyltrimethylammonium methyl sulfate, methacryloyloxyethyltrimethylammonium chloride, methacryloyloxyethyldimethylammonium chloride and methacryloyloxyethyldimethylammonium acetate.
Claim 7
Dependent Claim
52 words
The water-insoluble graft copolymer particles of claim 1 wherein monomer (a) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 95 mole % acrylamide and from about 30 mole % to about 5 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the cellulose reactive group is an aldehyde.
Claim 8
Dependent Claim
52 words
The water-insoluble graft copolymer particles of claim 1 wherein monomer (a) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 88 mole % acrylamide and from about 30 mole % to about 12 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the cellulose reactive group is an aldehyde.
Claim 9
Dependent Claim
321 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free-radical initiator (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), said monomer (a) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylo nitrile, methacrylonitrile, and monomers having the formula ##STR28## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR29## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR30## where Y is hydroxyl or halogen, ##STR31## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomers (1) employed.
Claim 10
Dependent Claim
321 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free-radical initiator (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), said monomer (a) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylo nitrile, methacrylonitrile, and monomers having the formula ##STR28## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR29## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR30## where Y is hydroxyl or halogen, ##STR31## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomers (1) employed.
Claim 11
Dependent Claim
300 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free-radical initiator (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), said monomer (a) being a monomer having the formula ##STR32## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR33## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR34## where Y is hydroxyl or halogen, ##STR35## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomers (1) employed.
Claim 12
Dependent Claim
300 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free-radical initiator (1) at least one ethylenically unsaturated monomer (a) and at least one polyethylenically unsaturated monomer (b) in an amount at least sufficient to provide cross linked graft copolymer particles, and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), said monomer (a) being a monomer having the formula ##STR32## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, said monomer (b) being selected from the group consisting of divinylbenzene; diallyl phthalate; ethylene glycol dimethacrylate; 1,3-butylene glycol dimethacrylate; 1,6-hexanediol dimethacrylate; polyethylene glycol dimethacrylate; polypropylene glycol dimethacrylate; trivinylbenzene; divinylnaphthalene; diallyl maleate; diallyl fumarate; trimethylol propane trimethacrylate; and pentaerythritol tetraacrylate, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR33## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR34## where Y is hydroxyl or halogen, ##STR35## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomers (1) employed.
Claim 13
Dependent Claim
18 words
The method of claim 7 wherein monomer (a) is styrene and the monoethylenically unsaturated amide monomer is acrylamide.
Claim 14
Dependent Claim
38 words
The process of claim 7 wherein monomer (a) is styrene, the monoethylenically unsaturated amide monomer is acrylamide and cationic monomer (i) is selected from the group consisting of methacryloyloxyethyltrimethylammonium methyl sulfate, methacryloyloxyethyltrimethylammonium chloride, methacryloyloxyethyldimethylammonium chloride and methacryloyloxyethyldimethylammonium acetate.
Claim 15
Dependent Claim
56 words
The process of claim 7 wherein the monomer (a) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 95 mole % acrylamide and from about 30 mole % to about 5 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the compound reacted with the prepolymer to provide cellulose reactive groups is glyoxal.
Claim 16
Dependent Claim
56 words
The process of claim 7 wherein the monomer (a) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 88 mole % acrylamide and from about 30 mole % to about 12 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the compound reacted with the prepolymer to provide cellulose reactive groups is glyoxal.
Claim 17
Dependent Claim
259 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (1) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR36## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR37## wherein R 1 is hydrogen or methyl, R 2 is hydrogen or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR38## where Y is hydroxyl or halogen, ##STR39## and --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 18
Dependent Claim
259 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (1) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR36## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR37## wherein R 1 is hydrogen or methyl, R 2 is hydrogen or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR38## where Y is hydroxyl or halogen, ##STR39## and --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 19
Dependent Claim
239 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (1) being a monomer having the formula ##STR40## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR41## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR42## where Y is hydroxyl or halogen, ##STR43## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 20
Dependent Claim
239 words
Water-insoluble graft copolymer particles consisting essentially of the free radical catalyzed graft copolymerization product of (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.), the prepolymer moiety of the graft copolymer particles being present on the surface of the particles, said monomer (1) being a monomer having the formula ##STR40## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR41## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR42## where Y is hydroxyl or halogen, ##STR43## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed, said prepolymer moiety of the particles having chemically bonded thereto a cellulose reactive group.
Claim 21
Dependent Claim
21 words
The water-insoluble graft copolymer particles of claim 13 wherein monomer (1) is styrene and the monoethylenically unsaturated amide monomer is acrylamide.
Claim 22
Dependent Claim
41 words
The water-insoluble graft copolymer particles of claim 13 wherein monomer (1) is styrene, the monoethylenically unsaturated amide monomer is acrylamide, and cationic monomer (i) is selected from the group consisting of methacryloyloxyethyltrimethylammonium methyl sulfate, methacryloyloxyethyltrimethylammonium chloride, methacryloyloxyethyldimethylammonium chloride and methacryloyloxyethyldimethylammonium acetate.
Claim 23
Dependent Claim
53 words
The water-insoluble graft copolymer particles of claim 13 wherein the monomer (1) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 95 mole % acrylamide and from about 30 mole % to about 5 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the cellulose reactive group is an aldehyde.
Claim 24
Dependent Claim
53 words
The water-insoluble graft copolymer particles of claim 13 wherein the monomer (1) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 88 mole % acrylamide and from about 30 mole % to about 12 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the cellulose reactive group is an aldehyde.
Claim 25
Dependent Claim
259 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free radical initiator (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.) said monomer (1) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR44## wherein R is hydrogen or methyl, Y is methyl or chlorine, n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR45## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR46## where Y is hydroxyl or halogen, ##STR47## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomer (1) employed.
Claim 26
Dependent Claim
259 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free radical initiator (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 2.5 (1 M NaCl, 1%, 25° C.) said monomer (1) being selected from the group consisting of methyl alpha-chloroacrylate, ethyl alpha-chloroacrylate, methyl methacrylate, isopropyl methacrylate, phenyl methacrylate, vinyl chloride, acrylonitrile, methacrylonitrile, and monomers having the formula ##STR44## wherein R is hydrogen or methyl, Y is methyl or chlorine, n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR45## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR46## where Y is hydroxyl or halogen, ##STR47## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 1 part to about 25 parts by weight for each 100 parts by weight of monomer (1) employed.
Claim 27
Dependent Claim
240 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free radical initiator (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.) said monomer (1) being a monomer having the formula ##STR48## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR49## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR50## where Y is hydroxyl or halogen, ##STR51## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed.
Claim 28
Dependent Claim
240 words
A process for preparing a latex of graft copolymer particles which comprises graft copolymerizing in aqueous media and in the presence of a free radical initiator (1) at least one ethylenically unsaturated monomer and (2) a water-soluble cationic prepolymer having an RSV of about 0.1 to about 1.0 (1 M NaCl, 1%, 25° C.) said monomer (1) being a monomer having the formula ##STR48## wherein R is hydrogen or methyl, Y is methyl or chlorine, and n is 0, 1, 2, or 3, and said prepolymer (2) being the addition polymerization product of (i) about 5 mole percent to 100 mole percent of a cationic monomer having the formula ##STR49## wherein R 1 is hydrogen or methyl, R 2 is hydrogen, or a C 1 -C 4 alkyl, R 3 is hydrogen, a C 1 -C 4 alkyl, ##STR50## where Y is hydroxyl or halogen, ##STR51## or --CH 2 CH 2 O) n H where n is an integer 1 or more and X - is an anion, and (ii) from about 95 mole percent to 0 mole percent of at least one monoethylenically unsaturated amide monomer, said prepolymer prior to graft copolymerization being reacted with a compound that provides the prepolymer with cellulose reactive groups, and the amount of prepolymer (2) employed in preparing the graft copolymer particles being from about 2 parts to about 10 parts by weight for each 100 parts by weight of monomer (1) employed.
Claim 29
Dependent Claim
18 words
The process of claim 19 wherein monomer (1) is styrene and the monoethylenically unsaturated amide monomer is acrylamide.
Claim 30
Dependent Claim
38 words
The process of claim 19 wherein monomer (1) is styrene, the monoethylenically unsaturated amide monomer is acrylamide and cationic monomer (i) is selected from the group consisting of methacryloyloxyethyltrimethylammonium methyl sulfate, methacryloyloxyethyltrimethylammonium chloride, methacryloyloxyethyldimethylammonium chloride and methacryloyloxyethyldimethylammonium acetate.
Claim 31
Dependent Claim
56 words
The process of claim 19 wherein the monomer (1) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 95 mole % acrylamide and from about 30 mole % to about 5 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the compound reacted with the prepolymer to provide cellulose reactive groups is glyoxal.
Claim 32
Dependent Claim
56 words
The process of claim 19 wherein the monomer (1) is styrene and the prepolymer (2) is prepared from about 70 mole % to about 88 mole % acrylamide and from about 30 mole % to about 12 mole % methacryloyloxyethyltrimethylammonium methyl sulfate, and the compound reacted with the prepolymer to provide cellulose reactive groups is glyoxal.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-05 | 1985-04-06 | 1985-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-05 | 1989-04-06 | 1989-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-05 | 1993-04-06 | 1993-10-06 | $7700.00 | Window Closed / Lapsed |