GB1099372A - Improvements relating to carbohydrate-derived polymers - Google Patents

Improvements relating to carbohydrate-derived polymers

Info

Publication number
GB1099372A
GB1099372A GB906565A GB906565A GB1099372A GB 1099372 A GB1099372 A GB 1099372A GB 906565 A GB906565 A GB 906565A GB 906565 A GB906565 A GB 906565A GB 1099372 A GB1099372 A GB 1099372A
Authority
GB
United Kingdom
Prior art keywords
acid
galactose
methyl
esters
diketal
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
GB906565A
Inventor
Tom Pate Bird
Eric Thomas Dewar
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.)
Milk Marketing Board
Original Assignee
Milk Marketing Board
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 Milk Marketing Board filed Critical Milk Marketing Board
Priority to GB906565A priority Critical patent/GB1099372A/en
Publication of GB1099372A publication Critical patent/GB1099372A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Saccharide Compounds (AREA)

Abstract

Polymers of 1,2:3,4-diketals of galactose esterified in the 6-position with an a ,b -olefinically unsaturated mono- or di-carboxylic acid are prepared by polymerizing the corresponding monomeric ester (see Division C2) in the presence of a free radical catalyst. The ketal residues may then be removed from the polymer by controlled hydrolysis, e.g. in the presence of an aqueous organic acid such as formic acid. The galactose diketal may be esterified with, for example, acrylic, methacrylic, ethacrylic, a -chloroacrylic or a -cyanoacrylic acid, or maleic, fumaric or itaconic acid or their half-esters. The ketal groups may be derived from acetone, methyl ethyl ketone, methyl propyl ketone, monochloroacetone or cyclohexanone. Polymerization can be effected in bulk or in benzene using azobisisobutyronitrile as catalyst. The galactose diketal acrylates or methacrylates may be copolymerized with monomers such as methyl acrylate, methyl methacrylate or acrylonitrile. The polymers after removal of the ketal groups can be converted to acetate, benzoate, phenyl carbamate, phenylhydrazone and phenylosazone derivatives; they may also be nitrated with nitrogen pentoxide, reduced with sodium borohydride to the corresponding polygalactitol-6-ester, and oxidized with chlorous acid to the corresponding galactonic acid polymer (or 1,4-lactone thereof) which can then be neutralized to the salt form, e.g. sodium or calcium salt.ALSO:Esters of an a ,b olefinically unsaturated polymerizable mono- or di-carboxylic acid and the hydroxyl group in the six position of galactose, specifically diisopropylidene galactose 6-methacrylate and acrylate are novel compounds and are prepared by reacting a ketone with galactose to form a 1,2:3,4-diketal and then reacting with the unsaturated acid. Acids specified are acrylic, methacrylic, a -chloroacrylic, a -cyanoacrylic, maleic, half esters of maleic or fumaric, a -ethacrylic, itaconic and half esters thereof, and the ketones may be acetone, methyl ethyl ketone, methyl propyl ketone, mono-chloracetone, and cyclohexanone, and a polymerization inhibitor may be present.
GB906565A 1965-03-03 1965-03-03 Improvements relating to carbohydrate-derived polymers Expired GB1099372A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB906565A GB1099372A (en) 1965-03-03 1965-03-03 Improvements relating to carbohydrate-derived polymers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB906565A GB1099372A (en) 1965-03-03 1965-03-03 Improvements relating to carbohydrate-derived polymers

Publications (1)

Publication Number Publication Date
GB1099372A true GB1099372A (en) 1968-01-17

Family

ID=9864724

Family Applications (1)

Application Number Title Priority Date Filing Date
GB906565A Expired GB1099372A (en) 1965-03-03 1965-03-03 Improvements relating to carbohydrate-derived polymers

Country Status (1)

Country Link
GB (1) GB1099372A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0180262A2 (en) * 1984-10-26 1986-05-07 Shell Internationale Researchmaatschappij B.V. A process for the preparation of water soluble vinyl saccharide polymers.
EP0237131A2 (en) * 1986-03-13 1987-09-16 Shell Internationale Researchmaatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0237132A2 (en) * 1986-03-13 1987-09-16 Shell Internationale Researchmaatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0251348A1 (en) * 1986-05-01 1988-01-07 Shell Internationale Researchmaatschappij B.V. Water-soluble saccharide polymers
WO2005063833A1 (en) * 2003-12-31 2005-07-14 Council Of Scientific And Industrial Research Oligomers containing n-acetyl glucosamine
US6977285B2 (en) 2004-03-30 2005-12-20 Council Of Scientific And Industrial Research Oligomers containing N-acetyl glucosamine (NAG)
US8871512B2 (en) 2010-10-27 2014-10-28 Empire Technology Development Llc Biocompatible polymerizable acrylate products and methods
US9174871B2 (en) 2012-11-02 2015-11-03 Empire Technology Development Llc Cement slurries having pyranose polymers
US9212245B2 (en) 2012-12-04 2015-12-15 Empire Technology Development Llc High performance acrylamide adhesives
US9238774B2 (en) 2012-11-02 2016-01-19 Empire Technology Development Llc Soil fixation, dust suppression and water retention

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0180262A2 (en) * 1984-10-26 1986-05-07 Shell Internationale Researchmaatschappij B.V. A process for the preparation of water soluble vinyl saccharide polymers.
EP0180262A3 (en) * 1984-10-26 1989-02-01 Shell Internationale Researchmaatschappij B.V. A process for the preparation of water soluble vinyl saccharide polymers.
EP0237132A3 (en) * 1986-03-13 1987-12-02 Shell Internationale Research Maatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0237132A2 (en) * 1986-03-13 1987-09-16 Shell Internationale Researchmaatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0237131A3 (en) * 1986-03-13 1987-12-02 Shell Internationale Research Maatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0237131A2 (en) * 1986-03-13 1987-09-16 Shell Internationale Researchmaatschappij B.V. Process for the preparation of water-soluble saccharide polymers
EP0251348A1 (en) * 1986-05-01 1988-01-07 Shell Internationale Researchmaatschappij B.V. Water-soluble saccharide polymers
WO2005063833A1 (en) * 2003-12-31 2005-07-14 Council Of Scientific And Industrial Research Oligomers containing n-acetyl glucosamine
US6977285B2 (en) 2004-03-30 2005-12-20 Council Of Scientific And Industrial Research Oligomers containing N-acetyl glucosamine (NAG)
US8871512B2 (en) 2010-10-27 2014-10-28 Empire Technology Development Llc Biocompatible polymerizable acrylate products and methods
US9428532B2 (en) 2010-10-27 2016-08-30 Empire Technology Development Llc Methods for making biocompatible polymerizable acrylate products
US9174871B2 (en) 2012-11-02 2015-11-03 Empire Technology Development Llc Cement slurries having pyranose polymers
US9238774B2 (en) 2012-11-02 2016-01-19 Empire Technology Development Llc Soil fixation, dust suppression and water retention
US9212245B2 (en) 2012-12-04 2015-12-15 Empire Technology Development Llc High performance acrylamide adhesives

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