CA2336447A1 - Continuous bulk polymerization and esterification process and compositions including the polymeric product - Google Patents

Continuous bulk polymerization and esterification process and compositions including the polymeric product Download PDF

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Publication number
CA2336447A1
CA2336447A1 CA002336447A CA2336447A CA2336447A1 CA 2336447 A1 CA2336447 A1 CA 2336447A1 CA 002336447 A CA002336447 A CA 002336447A CA 2336447 A CA2336447 A CA 2336447A CA 2336447 A1 CA2336447 A1 CA 2336447A1
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CA
Canada
Prior art keywords
polymeric
ethylenically unsaturated
functional monomer
unsaturated acid
polymeric product
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
CA002336447A
Other languages
French (fr)
Other versions
CA2336447C (en
Inventor
Kevin M. Andrist
Glenn C. Calhoun
Frederick C. Hansen
Dean R. Hellwig
Kurt A. Hessenius
D. Sunil Jayasuriya
Matt G. Lee
Stephen J. Maccani
H. Thomas Mills
Gregory R. Peterson
Paul E. Sandvick
Dennis M. Wilson
John E. Blasko
Steven M. Hurley
John P. Wiruth
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.)
BASF Corp
Original Assignee
S.C. Johnson Commercial Markets, Inc.
Kevin M. Andrist
Glenn C. Calhoun
Frederick C. Hansen
Dean R. Hellwig
Kurt A. Hessenius
D. Sunil Jayasuriya
Matt G. Lee
Stephen J. Maccani
H. Thomas Mills
Gregory R. Peterson
Paul E. Sandvick
Dennis M. Wilson
John E. Blasko
Steven M. Hurley
John P. Wiruth
Johnsondiversey, Inc.
Johnson Polymer, Llc
Basf Corporation
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 S.C. Johnson Commercial Markets, Inc., Kevin M. Andrist, Glenn C. Calhoun, Frederick C. Hansen, Dean R. Hellwig, Kurt A. Hessenius, D. Sunil Jayasuriya, Matt G. Lee, Stephen J. Maccani, H. Thomas Mills, Gregory R. Peterson, Paul E. Sandvick, Dennis M. Wilson, John E. Blasko, Steven M. Hurley, John P. Wiruth, Johnsondiversey, Inc., Johnson Polymer, Llc, Basf Corporation filed Critical S.C. Johnson Commercial Markets, Inc.
Publication of CA2336447A1 publication Critical patent/CA2336447A1/en
Application granted granted Critical
Publication of CA2336447C publication Critical patent/CA2336447C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C08F2/02—Polymerisation in bulk
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/04—Acids, Metal salts or ammonium salts thereof
    • 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
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/04—Anhydrides, e.g. cyclic anhydrides
    • C08F22/06—Maleic anhydride
    • 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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C09G1/16—Other polishing compositions based on non-waxy substances on natural or synthetic resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/52—Natural or synthetic resins or their salts
    • 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
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
    • 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
    • D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
    • D21H17/24—Polysaccharides
    • D21H17/28—Starch
    • 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
    • D21H21/14—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 characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents

Abstract

A continuous bulk polymerization and esterification process includes continuously charging into a reaction zone at least one ethylenically unsaturated acid-functional monomer and at least one linear or branched chain alkanol having greater than 11 carbon atoms.
The process includes including maintaining a flow rate. through the reaction zone sufficient to provide an average residence time of less than .50 minutes and maintaining a temperature in the reaction zone sufficient to produce a polymeric product incorporating at least some of the alkanol as an ester of the polymerized ethylenically unsaturated acid-functional monomer. The polymeric product is used in various processes to produce water-based compositions including emulsions and dispersions such as oil emulsions, wax dispersions, pigment dispersions, surfactants and coatings which contain the polymeric product. A
polymeric surfactant includes at least one ethylenically unsaturated acid-functional monomer which has been radically incorporated into the polymeric surfactant and at least one ester of the incorporated ethylenically unsaturated acid-functional monomer which has a linear or branched chain alkyl group with greater than 11 carbon atoms. The molar critical micelle concentration of the polymeric surfactant is less than 1.0 × 10 -2 moles/liter. Aqueous 2 percent neutralized solutions of certain polymeric surfactants have a surface tension of less than 45 mN/m at 30°C and exhibit a decrease in surface tension of at least 5 mN/m as the temperature warms from 30 °C to 50 °C.
CA002336447A 1998-07-10 1999-07-02 Continuous bulk polymerization and esterification process and compositions including the polymeric product Expired - Lifetime CA2336447C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9240598P 1998-07-10 1998-07-10
US60/092,405 1998-07-10
PCT/US1999/015163 WO2000002934A1 (en) 1998-07-10 1999-07-02 Continuous bulk polymerization and esterification process and compositions including the polymeric product

Publications (2)

Publication Number Publication Date
CA2336447A1 true CA2336447A1 (en) 2000-01-20
CA2336447C CA2336447C (en) 2007-08-21

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002336447A Expired - Lifetime CA2336447C (en) 1998-07-10 1999-07-02 Continuous bulk polymerization and esterification process and compositions including the polymeric product

Country Status (12)

Country Link
US (3) US6355727B1 (en)
EP (1) EP1097177B1 (en)
JP (1) JP4685239B2 (en)
KR (1) KR100619648B1 (en)
CN (1) CN1150224C (en)
AU (1) AU4969199A (en)
CA (1) CA2336447C (en)
DE (1) DE69937610T2 (en)
ES (1) ES2297929T3 (en)
MX (1) MXPA01000320A (en)
TW (1) TWI237642B (en)
WO (1) WO2000002934A1 (en)

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Also Published As

Publication number Publication date
CN1312824A (en) 2001-09-12
EP1097177A1 (en) 2001-05-09
EP1097177B1 (en) 2007-11-21
DE69937610T2 (en) 2008-09-25
CN1150224C (en) 2004-05-19
US6858678B2 (en) 2005-02-22
MXPA01000320A (en) 2001-07-31
US20050059782A1 (en) 2005-03-17
JP4685239B2 (en) 2011-05-18
CA2336447C (en) 2007-08-21
JP2002520430A (en) 2002-07-09
KR20010053452A (en) 2001-06-25
DE69937610D1 (en) 2008-01-03
AU4969199A (en) 2000-02-01
WO2000002934A1 (en) 2000-01-20
US20020082375A1 (en) 2002-06-27
TWI237642B (en) 2005-08-11
ES2297929T3 (en) 2008-05-01
US6355727B1 (en) 2002-03-12
KR100619648B1 (en) 2006-09-05

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