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GB663841A - Improvements in or relating to artificial resins and processes of making the same - Google Patents

Improvements in or relating to artificial resins and processes of making the same

Info

Publication number
GB663841A
GB663841A GB33787/47A GB3378747A GB663841A GB 663841 A GB663841 A GB 663841A GB 33787/47 A GB33787/47 A GB 33787/47A GB 3378747 A GB3378747 A GB 3378747A GB 663841 A GB663841 A GB 663841A
Authority
GB
United Kingdom
Prior art keywords
esters
ethyl
methyl
butyl
phenyl
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
GB33787/47A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical 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
Application filed by Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB663841A publication Critical patent/GB663841A/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
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/02—Ethene
    • 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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Graft Or Block Polymers (AREA)
  • Paper (AREA)

Abstract

Copolymers are prepared by mass polymerizing by heating a compound having the formula R-CH=CH2, where R is a phenyl or substituted phenyl radical, and a secondary alkyl half ester of an ethylene a ,b -dicarboxylic acid. Suitable vinyl compounds include styrene and nuclear halogen and methyl substituted styrenes, e.g. p-chloro- and p-methyl-styrenes. The alkyl groups of the esters preferably contain 3 to 8 carbon atoms and specified esters are isopropyl, sec.-butyl, methyl isoamyl and sec.-octyl half-esters of maleic, fumaric, citraconic, and phenyl, ethyl and benzyl maleic acids. The half esters may be used in the crude state and may be mixed and contain free acid. Polymerization is effected in the presence of a peroxy catalyst by heating at 60-70 DEG C. and finally at 125 DEG C. A small proportion of b -nitrostyrene may be incorporated as described in Specification 650,838 to obtain polymers of lower molecular weight. The products which are hard, colourless resins, form alkali solutions which are useful as sizes or paper coatings. Improved water resistance is obtained by drying at elevated temperatures or in the presence of materials capable of reacting with the carboxyl groups, e.g. calcium carbonate, polyethylene amine, polyglycols, polyvinyl alcohol and melamine-formaldehyde resins. The copolymers are soluble in nitrocellulose lacquer solvents such as ethyl-butyl acetate, glycol ethyl ether, toluene, ethyl or butyl alcohols and butanol-xylol and butanol-petroleum mixtures; and examples are given of compositions with (1) nitrocellulose, (2) polyvinyl butyral, and (3) Manila copal. On baking with polyvinyl butyral the polymers mutually react forming an insoluble film resistant to softening by heat. Plasticizers such as oleic and ricinoleic acid soaps, diglycol ricinoleate, glyceryl mono-oleate, dibutyl sebacate and the phthalic ester of diethylene glycol monoethyl ether and pigments such as clay or ground limestone may be added to the polymer compositions. Specification 588,725 also is referred to.
GB33787/47A 1946-12-28 1947-12-22 Improvements in or relating to artificial resins and processes of making the same Expired GB663841A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US663841XA 1946-12-28 1946-12-28

Publications (1)

Publication Number Publication Date
GB663841A true GB663841A (en) 1951-12-27

Family

ID=22069165

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33787/47A Expired GB663841A (en) 1946-12-28 1947-12-22 Improvements in or relating to artificial resins and processes of making the same

Country Status (1)

Country Link
GB (1) GB663841A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2717247A (en) * 1953-12-21 1955-09-06 Mensanto Chemical Company Interpolymers of styrene, allyl acetate and alkyl half esters of maleic acid and process for preparing the same
US2798062A (en) * 1953-11-13 1957-07-02 Monsanto Chemicals Low molecular weight heteropolymers of styrene and alkyl esters of maleic acid and process for preparing the same
US3331886A (en) * 1963-01-28 1967-07-18 Dow Chemical Co Thermosettable coating comprising (1) an organic polycarboxylic polymeric material and (2) a resinous polyepoxide-alkanol amine adduct
EP1396576A1 (en) * 2002-09-04 2004-03-10 Raisio Chemicals Oy Coating composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2798062A (en) * 1953-11-13 1957-07-02 Monsanto Chemicals Low molecular weight heteropolymers of styrene and alkyl esters of maleic acid and process for preparing the same
US2717247A (en) * 1953-12-21 1955-09-06 Mensanto Chemical Company Interpolymers of styrene, allyl acetate and alkyl half esters of maleic acid and process for preparing the same
US3331886A (en) * 1963-01-28 1967-07-18 Dow Chemical Co Thermosettable coating comprising (1) an organic polycarboxylic polymeric material and (2) a resinous polyepoxide-alkanol amine adduct
EP1396576A1 (en) * 2002-09-04 2004-03-10 Raisio Chemicals Oy Coating composition

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