CA2377859A1 - High molecular weight zwitterionic polymers - Google Patents

High molecular weight zwitterionic polymers Download PDF

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Publication number
CA2377859A1
CA2377859A1 CA002377859A CA2377859A CA2377859A1 CA 2377859 A1 CA2377859 A1 CA 2377859A1 CA 002377859 A CA002377859 A CA 002377859A CA 2377859 A CA2377859 A CA 2377859A CA 2377859 A1 CA2377859 A1 CA 2377859A1
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CA
Canada
Prior art keywords
molecular weight
high molecular
weight water
acrylamide
dimethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002377859A
Other languages
French (fr)
Other versions
CA2377859C (en
Inventor
Phillip W. Carter
Patrick G. Murray
Larry E. Brammer, Jr.
Andrew J. Dunham
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ChampionX LLC
Original Assignee
Nalco Chemical Company
Phillip W. Carter
Patrick G. Murray
Larry E. Brammer, Jr.
Andrew J. Dunham
Ondeo Nalco Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nalco Chemical Company, Phillip W. Carter, Patrick G. Murray, Larry E. Brammer, Jr., Andrew J. Dunham, Ondeo Nalco Company filed Critical Nalco Chemical Company
Publication of CA2377859A1 publication Critical patent/CA2377859A1/en
Application granted granted Critical
Publication of CA2377859C publication Critical patent/CA2377859C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/06—Paper forming aids
    • D21H21/10—Retention agents or drainage improvers
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
    • C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
    • C02F1/56—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/32—Polymerisation in water-in-oil emulsions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups

Abstract

This invention is directed to high molecular weight water-soluble zwitterionic polymers derived from zwitterionic and nonionic monomer units, and to the use of the polymers in papermaking processes.

Claims (14)

1. A high molecular weight water-soluble zwitterionic polymer comprising from about 50 to about 99.9 mole percent of one or more nonionic monomers and from about 0.1 to about 50 mole percent of one or more zwitterionic monomers of formula <IMGs>

wherein L+ is a group of formula <IMGs>

L- is a group of formula R1 and R8 are independently hydrogen or methyl;

R2, R3, R4, R5 and R6 are independently selected from hydrogen and C1-C4 alkyl;

Y1 and Y2 are independently selected from O or NR2;
W+ is -S+R3- or -N+-R2R3-;

W- is ;
Z- is CO2-, SO3-, <IMGs>
Z+ is -N+R5R6R7;
m is 2 or 3; and n is 1-5.
2. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomers are selected from acrylamide, methacrylamide, N-methylacrylamide, N, N dimethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, N-(2-hydroxypropyl)methacrylamide, N-methylolacrylamide, N-vinylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, poly(ethylene glycol)(meth)acrylate, poly(ethylene glycol) monomethyl ether mono(meth)acryate, N-vinyl-2-pyrrolidone, glycerol mono((meth)acrylate), 2-hydroxyethyl(meth)acrylate, vinyl methylsulfone and vinyl acetate.
3. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomers are selected from acrylamide and methacrylamide.
4. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide.
5. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide and the zwitterionic monomer is <IMGs>
6. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide and the zwitterionic monomer is
7. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide and the zwitterionic monomer is
8. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide and the zwitterionic monomer is selected from N,N-dimethyl-N-acryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine, N,N dimethyl-N-acrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, N,N-dimethyl-N-methacryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-methacrylamidopropyl-N-(3-sulfopropyl)-ammonium betaine, 2-(methylthio)ethyl methacryloyl-S-(sulfopropyl)-sulfonium betaine, 2-[(2-acryloylethyl)dimethylammonio]ethyl 2-methyl phosphate, 2-(acryloyloxyethyl)-2'-(trimethylammonium)ethyl phosphate and [(2-acryloylethyl)dimethylammonio]methyl phosphoric acid.
9. The high molecular weight water-soluble zwitterionic polymer of claim 1 wherein the nonionic monomer is acrylamide and the zwitterionic monomer is selected from N,N-dimethyl-N-acryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-acrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, N,N-dimethyl-N-methacryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine and N,N-dimethyl-N-methacrylamidopropyl-N-(3-sulfopropyl)-ammonium betaine.
10. A method for increasing retention and drainage in fibrous suspensions of pulp during processing of said pulp comprising adding to the pulp an effective flocculating amount of the high molecular weight water-soluble zwitterionic polymer of claim 1.
11. The method of claim 10 further comprising adding bentonite, microparticles, or resin enhancers to the pulp.
12. The method of claim 10 further comprising adding coagulant to the pulp.
13. A method of removing suspended solids and clarifying white water in the papermaking process comprising adding to the white water, pulp washers, or thickeners an effective flocculating amount of the high molecular weight water-soluble zwitterionic polymer of claim 1.
14. A method of increasing filler retention comprising adding an effective flocculating amount of the high molecular weight water-soluble zwitterionic polymer of claim 1 to the filler slurry prior to addition to the paper furnish.
CA2377859A 1999-07-07 2000-06-28 High molecular weight zwitterionic polymers Expired - Lifetime CA2377859C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/349,054 US6313246B1 (en) 1999-07-07 1999-07-07 High molecular weight zwitterionic polymers
US09/349,054 1999-07-07
PCT/US2000/017841 WO2001004201A1 (en) 1999-07-07 2000-06-28 High molecular weight zwitterionic polymers

Publications (2)

Publication Number Publication Date
CA2377859A1 true CA2377859A1 (en) 2001-01-18
CA2377859C CA2377859C (en) 2010-10-19

Family

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Family Applications (1)

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CA2377859A Expired - Lifetime CA2377859C (en) 1999-07-07 2000-06-28 High molecular weight zwitterionic polymers

Country Status (14)

Country Link
US (2) US6313246B1 (en)
EP (1) EP1198503A4 (en)
JP (2) JP4132017B2 (en)
KR (1) KR100596068B1 (en)
CN (1) CN100334149C (en)
AR (1) AR024673A1 (en)
AU (1) AU5776000A (en)
BR (1) BR0012251A (en)
CA (1) CA2377859C (en)
MX (1) MXPA02000149A (en)
NO (1) NO20020033L (en)
NZ (1) NZ516417A (en)
TW (1) TWI254728B (en)
WO (1) WO2001004201A1 (en)

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Publication number Publication date
CA2377859C (en) 2010-10-19
US6313246B1 (en) 2001-11-06
KR20020034153A (en) 2002-05-08
JP4132017B2 (en) 2008-08-13
EP1198503A4 (en) 2005-03-02
NO20020033L (en) 2002-03-05
BR0012251A (en) 2002-03-26
JP2008174897A (en) 2008-07-31
NO20020033D0 (en) 2002-01-04
MXPA02000149A (en) 2002-07-02
JP2003504476A (en) 2003-02-04
NZ516417A (en) 2003-09-26
KR100596068B1 (en) 2006-07-03
WO2001004201A1 (en) 2001-01-18
AU5776000A (en) 2001-01-30
CN1359408A (en) 2002-07-17
TWI254728B (en) 2006-05-11
EP1198503A1 (en) 2002-04-24
CN100334149C (en) 2007-08-29
US6590051B1 (en) 2003-07-08
AR024673A1 (en) 2002-10-23

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