GB757078A - Improvements relating to styrenated esters of epoxy resinous materials - Google Patents

Improvements relating to styrenated esters of epoxy resinous materials

Info

Publication number
GB757078A
GB757078A GB339453A GB339453A GB757078A GB 757078 A GB757078 A GB 757078A GB 339453 A GB339453 A GB 339453A GB 339453 A GB339453 A GB 339453A GB 757078 A GB757078 A GB 757078A
Authority
GB
United Kingdom
Prior art keywords
tert
styrene
oil fatty
fatty acid
cumene hydroperoxide
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
GB339453A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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
Priority claimed from US279445A external-priority patent/US2736717A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB757078A publication Critical patent/GB757078A/en
Expired legal-status Critical Current

Links

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
    • C08F212/00—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 an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene
    • 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
    • C08F242/00—Copolymers of drying oils with other monomers
    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/10—Epoxy resins modified by unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D125/00—Coating compositions based on 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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/04—Homopolymers or copolymers of styrene
    • C09D125/08—Copolymers of styrene
    • C09D125/14—Copolymers of styrene with unsaturated esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)

Abstract

Styrene or a ring-substituted derivative thereof and an organic peroxide polymerization catalyst are added in small increments to a drying or semi-drying oil fatty acid or tall oil fatty acid or lower alkyl ester thereof at 130-215 DEG C. and the mixture is heated until reaction is complete, whereupon the epoxy reaction product of a polyhydric phenol with an epi- or di-halohydrin is added and reaction is continued until esterification is substantially complete. Suitable substituted styrenes are the o-methyl, m-ethyl, p-propyl, 2,4-dimethyl, 2,5-diethyl, 3,5-dibutyl, o-, m- or p-chloro, 2,4-dichloro or 2,5-dichloro derivatives. Catalysts mentioned are 2,2 - bis - (tert. - butylperoxy)-butane; tert.-butyl hydroperoxide; di-tert.-butyl peroxide; tert.-butyl propyl peracids; tert.-butylpentamethylethyl peroxide; cumene hydroperoxide. The first stage of the process may be carried out in an organo solvent, e.g. xylol, Varsol, Solvesso (Registered Trade Mark), Solvasol, kerosene, toluol, high-flash naphtha, heavy aromatic naphtha. Suitable polyhydric phenols for the epoxy resins are resorcinol, 2,2-diparahydroxyphenylpropane, p,p1-dihydroxybenzophenone, p,p1 - dihydroxydiphenyl, p,p1-dihydroxyldibenzyl, and o,o1,p,p1-tetrahydroxydiphenyldimethyl methane. When using a lower alkyl ester of the fatty acid, or transesterification catalyst, e.g. lithage, sodium methoxide, sodium hydroxide is preferably employed. The products are useful for coating-especially for cap closures. The compositions may include a pigment, e.g. TiO2 and a dryer, e.g. cobalt naphthenate. In examples, epoxy resins from epichlorhydric and 2,2-diparahydroxyphenylpropane are esterified with copolymers prepared with cumene hydroperoxide from:-Examples 1, 2, 3, 6 and 7, styrene and a cottonseed oil acid fraction prepared with cumene hydroperoxide. Example 4, styrene and tall oil fatty acids, and Example 5, styrene and linseed oil fatty acids. In each case the product was cut with a heavy aromatic naphtha Amsco F-80 to yield a coating composition.
GB339453A 1952-03-29 1953-02-06 Improvements relating to styrenated esters of epoxy resinous materials Expired GB757078A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US279445A US2736717A (en) 1952-03-29 1952-03-29 Copolymers of vinyl aromatic compound, fatty acid ester of epoxy resin and a vegetable oil

Publications (1)

Publication Number Publication Date
GB757078A true GB757078A (en) 1956-09-12

Family

ID=23069003

Family Applications (1)

Application Number Title Priority Date Filing Date
GB339453A Expired GB757078A (en) 1952-03-29 1953-02-06 Improvements relating to styrenated esters of epoxy resinous materials

Country Status (1)

Country Link
GB (1) GB757078A (en)

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