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GB1140520A - Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use - Google Patents

Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use

Info

Publication number
GB1140520A
GB1140520A GB32402/66A GB3240266A GB1140520A GB 1140520 A GB1140520 A GB 1140520A GB 32402/66 A GB32402/66 A GB 32402/66A GB 3240266 A GB3240266 A GB 3240266A GB 1140520 A GB1140520 A GB 1140520A
Authority
GB
United Kingdom
Prior art keywords
ester compounds
cationic ester
novel
reaction
polymerized
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.)
Expired
Application number
GB32402/66A
Inventor
Aldo De Benedictis
Igor Sobolev
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.)
SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
Original Assignee
SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
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 SHELL INT RESEARCH, Shell Internationale Research Maatschappij BV filed Critical SHELL INT RESEARCH
Priority to GB32402/66A priority Critical patent/GB1140520A/en
Publication of GB1140520A publication Critical patent/GB1140520A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/016—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
    • 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
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • 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
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/22—Esters containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C11/00—Surface finishing of leather
    • C14C11/003—Surface finishing of leather using macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/01—Organic compounds containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/01—Organic compounds containing nitrogen
    • B03D1/011—Quaternary ammonium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

1,140,520. Cationic ester compounds containing a quaternary nitrogen atom. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 19 July, 1966, No. 32402/66. Heading C2C. [Also in Divisions B2, C3, C6 and D2] The invention comprises cationic ester compounds of the general formula wherein R is C 1 -C 20 alkyl, R<SP>1</SP> is an aliphatic hydrocarbon group having from 2 to 7 carbon atoms and 1 or 2 ethylenic linkages, X is Cl or Br and n is 1 or 2 with the proviso that if n is 2 R<SP>1</SP> has not more than 4 carbon atoms. They may be obtained by reacting the corresponding glycidyl trialkyl ammonium halide with the corresponding unsaturated mono- or di-carboxylic acid in the liquid phase. The liquid phase may be water which may contain other solvents, e.g. C 1 -C 4 alcohols. The reaction is preferably effected at between 45‹ C. and 140‹ C. The R groups are preferably C 1 -C 4 alkyl groups. In an alternative procedure the compounds are obtained by directly reacting the corresponding trialkylamine and the corresponding 2,3-epoxy-1-halo-propane with the corresponding unsaturated mono- or di-carboxylic acid in an inert polar solvent, e.g. a sulphone, N,N-disubstituted alkyl amide, a sulphoxide or a secondary or tertiary alcohol. The reaction, in either type of process, should preferably be carried out in the presence of a polymerization inhibitor and suitable reaction temperatures are from 30‹ to 110‹ C. The products may be polymerized, or co-polymerized with an ethylenically unsaturated monomer, to form polymeric esters which are useful as agents for treating fibrous materials and for the separation of clays and ores from aqueous suspensions. They may also be esterified or etherified on the hydroxyl group, or the ethylenio linkage in the group R<SP>1</SP> may be epoxidized to form epoxy resin precursors.
GB32402/66A 1966-07-19 1966-07-19 Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use Expired GB1140520A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB32402/66A GB1140520A (en) 1966-07-19 1966-07-19 Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB32402/66A GB1140520A (en) 1966-07-19 1966-07-19 Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use

Publications (1)

Publication Number Publication Date
GB1140520A true GB1140520A (en) 1969-01-22

Family

ID=10338070

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32402/66A Expired GB1140520A (en) 1966-07-19 1966-07-19 Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use

Country Status (1)

Country Link
GB (1) GB1140520A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2103898A1 (en) * 1970-01-30 1971-08-12 Gaf Corp Quaternary copolymers
US4216156A (en) * 1978-01-27 1980-08-05 Chem-Y, Fabriek van Chemische Produkten, B.V. Stable concentrated solution of glycidyltrimethylammonium chloride and process for preparing stable concentrated solutions of glycidyltrimethylammonium chloride
DK154423B (en) * 1969-10-20 1988-11-14 Kendall & Co QUATERNES AMMONIUM COMPOUND FOR SIMILAR USE AS EMULSION STABILIZER AND AS COMONOMS BY EMULSION POLYMERIZATION OF ETHYLENIC Saturated MONOMERS
US5008444A (en) * 1988-11-30 1991-04-16 Polypure, Inc. Process for the production of substituted acryloyloxyhydroxypropyltrialkylammonium chloride
US5132383A (en) * 1988-11-30 1992-07-21 Polypure, Inc. Copolymers of 3-methacryloyloxy-2-hydroxypropyl trimethylammonium chloride monomer and vinyl monomer
WO1995030777A1 (en) * 1994-05-06 1995-11-16 Henkel Kommanditgesellschaft Auf Aktien Cationic agents for stuffing leather and hides
WO2001055083A1 (en) * 2000-01-27 2001-08-02 Biodep, Inc. Inositol derivatives and their pharmaceutical use
CN107746446A (en) * 2016-10-14 2018-03-02 中国石油大学(华东) A kind of preparation method of ternary polymerization amphiprotic polyacrylamide
CN107746378A (en) * 2016-10-14 2018-03-02 中国石油大学(华东) A kind of polymerizable quaternaries cation monomer and preparation method thereof
CN109530094A (en) * 2019-01-17 2019-03-29 湖南中医药大学 Amide groups hydroxycarboxylic acid/hydroximic acid compound and its application in mineral floating

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK154423B (en) * 1969-10-20 1988-11-14 Kendall & Co QUATERNES AMMONIUM COMPOUND FOR SIMILAR USE AS EMULSION STABILIZER AND AS COMONOMS BY EMULSION POLYMERIZATION OF ETHYLENIC Saturated MONOMERS
DE2103898A1 (en) * 1970-01-30 1971-08-12 Gaf Corp Quaternary copolymers
US4216156A (en) * 1978-01-27 1980-08-05 Chem-Y, Fabriek van Chemische Produkten, B.V. Stable concentrated solution of glycidyltrimethylammonium chloride and process for preparing stable concentrated solutions of glycidyltrimethylammonium chloride
US5008444A (en) * 1988-11-30 1991-04-16 Polypure, Inc. Process for the production of substituted acryloyloxyhydroxypropyltrialkylammonium chloride
US5132383A (en) * 1988-11-30 1992-07-21 Polypure, Inc. Copolymers of 3-methacryloyloxy-2-hydroxypropyl trimethylammonium chloride monomer and vinyl monomer
WO1995030777A1 (en) * 1994-05-06 1995-11-16 Henkel Kommanditgesellschaft Auf Aktien Cationic agents for stuffing leather and hides
US5660759A (en) * 1994-05-06 1997-08-26 Henkel Kommanditgesellschaft Auf Aktien Cationic formulations for oiling leathers and skins
WO2001055083A1 (en) * 2000-01-27 2001-08-02 Biodep, Inc. Inositol derivatives and their pharmaceutical use
CN107746446A (en) * 2016-10-14 2018-03-02 中国石油大学(华东) A kind of preparation method of ternary polymerization amphiprotic polyacrylamide
CN107746378A (en) * 2016-10-14 2018-03-02 中国石油大学(华东) A kind of polymerizable quaternaries cation monomer and preparation method thereof
CN109530094A (en) * 2019-01-17 2019-03-29 湖南中医药大学 Amide groups hydroxycarboxylic acid/hydroximic acid compound and its application in mineral floating

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