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GB944322A - Ethylenically polymerizable long-chain compound and method of preparing same - Google Patents

Ethylenically polymerizable long-chain compound and method of preparing same

Info

Publication number
GB944322A
GB944322A GB826960A GB826960A GB944322A GB 944322 A GB944322 A GB 944322A GB 826960 A GB826960 A GB 826960A GB 826960 A GB826960 A GB 826960A GB 944322 A GB944322 A GB 944322A
Authority
GB
United Kingdom
Prior art keywords
soybean oil
alkyl
acid
methacrylic acid
epoxidised
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
GB826960A
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.)
Primary Products Ingredients Americas LLC
Original Assignee
Tate and Lyle Ingredients Americas LLC
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 Tate and Lyle Ingredients Americas LLC filed Critical Tate and Lyle Ingredients Americas LLC
Publication of GB944322A publication Critical patent/GB944322A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • 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
    • C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • 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
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives 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
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or 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 halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—Compositions of homopolymers or 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride

Landscapes

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

Abstract

The invention comprises an ethylenically unsaturated hydrocarbon, carboxylic acid or derivative thereof with at least one aliphatic chain of from 10 to 24 carbon atoms, with at least one pair of adjacent carbon atoms substituted thus: <FORM:0944322/C2/1> where p is an integer from 0 to 2, and X is hydrogen halogen, cyano, -CH2-COO alkyl (C1-4), phenyl, benzyl, or alkyl (C1-4). The carboxylate derivatives are esters, amides, salts, alcohols, ethers, amines, mercaptans isocyanates, nitriles, halides or quaternary ammonium salts. Compounds described are animal or vegetable oils e.g. soy bean, corn, cotton seed, hemp seed, safflower, peanut, linseed, rice bran, olive, cod, herring, tall, or menhaden oil wherein at least one fatty acid chain in each glyceride molecule has a pair of adjacent carbon atoms substituted as above; a compound derived from a vegetable oil fatty acid ester and monohydric alcohol substituted in at least one C10 to C24 chain as above and in which p is O; the mono- or diglyceride of the fatty acid with the substituted C10 to C24 chain; a monohydric alcohol with the alkyl radical, C10 to C24 substituted as above; or esters of general formula: <FORM:0944322/C2/2> wherein Z represents phenyl, benzyl, 0-, m-, and p-tolyl, rescorcinyl, furfuryl, cyclohexyl, inosityl, glyceryl, pentaerithrityl, orabityl, sorbityl, alkylene (C2-C12) and alkyl (C12-C24), m is 1-6, n is 0 to 5, R is alkyl C1-C24, and Z and R provide at least one ethylenically unsaturated aliphatic chain of C10 to C24 atoms. The compounds are prepared by reacting an epoxy compound e.g. a fatty acid glyceride epoxidised in at least one glyceride acyl group, and an aliphatic carboxylic acid H2C=CX-(CH2)n-COOH, amide or alcohol, wherein n is 0, 1 or 2 and X is hydrogen, halogen, cyano, -CH2-COO alkyl (C1-C4), phenyl, benzyl, or alkyl (C1-C4) in the presence of a polymerization inhibitor. Oxygen or oxygen containing gas may be continually passed through the reaction mixture and examples of the acid are, acrylic, methacrylic, vinyl acetic, vinyl acrylic and alkyl acetic acids and methyl acid itaconate. Examples describe the reaction of epoxidised soybean oil with acrylic or methacrylic acids; epoxidised soybean fatty acid 2-ethyl hexyl esters with methacrylic acid; epoxidised soybean oil and monomethyl itaconate; epoxidised tall oil fatty acid isooctyl esters and methacrylic acid; epoxidised soybean oil fatty acid monoglyceride and methacrylic acid epoxidised soybean oil fatty alcohol and methacrylic acid, a -chloroacrylic a -phenyl acrylic, a -benzyl acrylic, and a -cyanoacrylic acids. The products may be polymerized or copolymerized with cross-linking.ALSO:Polymers and copolymers of ethylenically unsaturated hydrocarbons and carboxylic acids or derivatives thereof with at least one aliphatic chain of from 10 to 24 carbon atoms and with at least one pair of adjacent carbon atoms substituted thus: <FORM:0944322/C3/1> where p is an integer from 0 to 2 and X is hydrogen, halogen, cyano, -CH2.COO (alkyl C,1-4,), phenyl, benzyl, or alkyl (C, 1-4), (see Division C2) are prepared using peroxide catalysts. Copolymers with methyl and ethyl methacrylates, ethyl and stearyl acrylate, acrylic and methacrylic acids, styrene and methyl styrene, alkyl alcohol, vinyl acetate and stearate, acrylonitrile, butadiene, maleic, crotonic and cinnamic acids, dipentene, myrcene are mentioned and the products are viscous liquids to rubbery and hard resins. Examples describe the reaction of epoxidised soybean oil with acrylic or methacrylic acid and the homo polymerization of the product and the copolymerization of the soybean oil-acrylic acid and the soybean oil-methacrylic acid products with styrene and the copolymerization of the soybean oil-methacrylic acid product with methyl methacrylate; of epoxidised soybean fatty acid 2-ethylhexyl ester and methacrylic acid and the homo- and copolymerization of the product with methyl and butyl methacrylates; of epoxidised soybean oil and monomethylitaconate and the homopolymerization of the product; of epoxidised tall oil fatty acid isooctyl esters and epoxidised soybean oil and the copolymerization of the product with methacrylic acid; of epoxidised soybean oil fatty acid monoglyceride and methacrylic acid and the homo- or copolymerization of the product with styrene; of epoxidised soybean oil fatty alcohol and methacrylic acid and the homopolymerization of the product. The products are useful as protective coatings, sizing and textile and paper additives, laminating and potting resins, stabilizer-plasticizers and adhesives.
GB826960A 1959-03-18 1960-03-09 Ethylenically polymerizable long-chain compound and method of preparing same Expired GB944322A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US80007159A 1959-03-18 1959-03-18

Publications (1)

Publication Number Publication Date
GB944322A true GB944322A (en) 1963-12-11

Family

ID=25177432

Family Applications (1)

Application Number Title Priority Date Filing Date
GB826960A Expired GB944322A (en) 1959-03-18 1960-03-09 Ethylenically polymerizable long-chain compound and method of preparing same

Country Status (4)

Country Link
BE (1) BE593359A (en)
DE (1) DE1443142A1 (en)
GB (1) GB944322A (en)
NL (2) NL249517A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034893A2 (en) * 1980-02-15 1981-09-02 Monsanto Company Compositions for bonding fibrous substrates and cellulosic fibrous substrate treated therewith

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034893A2 (en) * 1980-02-15 1981-09-02 Monsanto Company Compositions for bonding fibrous substrates and cellulosic fibrous substrate treated therewith
EP0034893A3 (en) * 1980-02-15 1982-06-09 Monsanto Company Compositions for bonding fibrous substrates and cellulosic fibrous substrate treated therewith

Also Published As

Publication number Publication date
NL126251C (en)
NL249517A (en)
DE1443142A1 (en) 1968-10-17
BE593359A (en)

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