GB806730A - Improvements in the production of unsaturated polyester resins and of copolymers therefrom - Google Patents

Improvements in the production of unsaturated polyester resins and of copolymers therefrom

Info

Publication number
GB806730A
GB806730A GB38799/56A GB3879956A GB806730A GB 806730 A GB806730 A GB 806730A GB 38799/56 A GB38799/56 A GB 38799/56A GB 3879956 A GB3879956 A GB 3879956A GB 806730 A GB806730 A GB 806730A
Authority
GB
United Kingdom
Prior art keywords
acid
unsaturated
vinyl
esters
compounds
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
GB38799/56A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB806730A publication Critical patent/GB806730A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/553Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

An unsaturated polyester resin is the polycondensation product of (a) an alpha-unsaturated polycarboxylic acid, (b) a polyhydric alcohol, and (c) at least 30 per cent with reference to the total weight of the reactable materials of a reaction product of colophony or abietic acid and an alpha-ethylenically unsaturated monocarboxylic acid (e.g. acrylic or chloracrylic acid). Specified unsaturated polycarboxylic acids are maleic, fumaric, itaconic, aconitic, citraconic, monochloromaleic and dichloromaleic acids. Specified polyhydric alcohols are ethylene, 1 : 2 - propylene, 1 : 3 - propylene, 1 : 4-butylene, 1 : 5-pentylene, 1 : 6-hexylene, diethylene, triethylene and tetraethylene glycols; also 2 : 2-dimethylpropanediol-1 : 3, 1 : 4-butene diol, 1 : 2-butene diol, glycerine, butanetriol, trimethylol propane, pentaerythritol, terephthalic alcohol or halogensubstituted derivatives thereof. Part of the unsaturated polycarboxylic acid may be replaced by a saturated polycarboxylic acid (e.g. phthalic, terephthalic, phenylene dibutyric, succinic, glutaric, alpha-methylglutaric, adipic, oxadibutyric, sulphonyl dibutyric or tetrachlorophthalic acid) or by a saturated or unsaturated hydroxyacid. Part of the polyhydric alcohol may be replaced by an amino alcohol (e.g. ethanolamine). Polycondensation may be effected by reacting together all the components simultaneously or by reacting a known unsaturated polyester resin (e.g. from maleic acid, phthalic acid and ethylene glycol) with an unsaturated polyester modified with the reaction product of colophony or abietic acid and an alpha-unsaturated monocarboxylic acid. Reaction may be effected in presence of a solvent, catalyst or inhibitor (e.g. quinone, hydroquinone, pyrocatechol, or tert.-butyl p-cresol). The polyesters may be compounded with oils, alkyd resins, urea-formaldehyde resins, phenol-formaldehyde resins, coumarone resins, polyvinyl esters, polyacrylic esters and polystyrene. Those polyesters containing terminal hydroxyl groups may be chain-lengthened by reaction with polyisocyanates. Examples disclose unsaturated polyesters made from (1), (2), (3) and (4) maleic anhydride, a diene adduct of colophony and acrylic acid and 1 : 2-propylene glycol; (9) fumaric acid, itaconic acid, phthalic anhydride, a diene adduct of colophony and acrylic acid, 1 : 2-propylene glycol and ethylene glycol; (10) maleic anhydride, succinic acid, a diene adduct of colophony and acrylic acid, 1 : 2-propylene glycol and 1 : 4-butylene glycol. Unsaturated polyester copolymers.-The unsaturated polyesters may be copolymerized with unsaturated compounds of formula <FORM:0806730/IV (a)/1> where R1 is an aromatic, isocyclic or heterocyclic radical or a carboxylic, halogen, acyloxy, carbalkoxy or alkoxy radical or an aldehyde, ketone, nitrile, lactam or sulphonic group and R2 is halogen, alkyl or hydrogen. Specified vinyl compounds are styrene and its derivatives and homologues, divinyl benzene, N-vinyl carbazole, acrylic or methacrylic acids or their esters, amides or nitriles (e.g. acrylamide, methacrylamide, methylene - bis - methacrylamide, methyl methacrylate or ethyl acrylate), also triacyloyl perhydrotriazine, alpha-chloracrylic esters, vinyl ethers, vinyl esters (e.g. vinyl propionate), N-vinyl lactams, vinyl ketone or vinyl sulphones. Specified allyl compounds are the allyl esters of saturated mono- or polycarboxylic acids or other organic or inorganic acids (e.g. phthalic, maleic, succinic, cyanuric or phosphosphoric), also the allyl ethers of mono-or poly-hydric alcohols and the esters of chloroallyl alcohol or methallyl alcohol. In Example 8, a mixture of unsaturated polyester, N-vinylcarbazole and methacrylamide is copolymerized. Preferably the polyester has a monomer content of 20-50 per cent. Copolymerization may be effected with the aid of light (especially ultra-violet), azo compounds or peroxy compounds (with or without compounds of Pb, Mn, Co, Fe or Cr or amines as accelerators). Copolymerization may be effected in presence of cork flour, quartz flour, kieselguhr, heavy spar, graphite, antimony trioxide, glass fibres or calico fabrics.
GB38799/56A 1955-12-21 1956-12-20 Improvements in the production of unsaturated polyester resins and of copolymers therefrom Expired GB806730A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE806730X 1955-12-21

Publications (1)

Publication Number Publication Date
GB806730A true GB806730A (en) 1958-12-31

Family

ID=6722682

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38799/56A Expired GB806730A (en) 1955-12-21 1956-12-20 Improvements in the production of unsaturated polyester resins and of copolymers therefrom

Country Status (1)

Country Link
GB (1) GB806730A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3194794A (en) * 1960-01-27 1965-07-13 Eastman Kodak Co Process of preparing polymers of nuclearly polychlorinated aromatic dicarboxylic acids and diamines having at least 4 carbons
US3218274A (en) * 1961-02-13 1965-11-16 Archer Daniels Midland Co Two-package coating system comprising a polyester having an acid number of at least 50 in one of the packages thereof
WO2010108966A1 (en) * 2009-03-25 2010-09-30 Dsm Ip Assets B.V. Process for preparing unsaturated polyester
CN106519135A (en) * 2016-12-03 2017-03-22 安徽富丽华化工有限公司 Modified unsaturated polyester resin with low viscosity and corrosion resistance and preparation method of modified unsaturated polyester resin
CN106589749A (en) * 2016-12-03 2017-04-26 安徽富丽华化工有限公司 Modified unsaturated polyester resin having excellent acid and alkali resistance, and preparation method thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3194794A (en) * 1960-01-27 1965-07-13 Eastman Kodak Co Process of preparing polymers of nuclearly polychlorinated aromatic dicarboxylic acids and diamines having at least 4 carbons
US3218274A (en) * 1961-02-13 1965-11-16 Archer Daniels Midland Co Two-package coating system comprising a polyester having an acid number of at least 50 in one of the packages thereof
US8470926B2 (en) 2009-03-05 2013-06-25 Dsm Ip Assets B.V. Unsaturated polyester resin
CN102361905A (en) * 2009-03-25 2012-02-22 帝斯曼知识产权资产管理有限公司 Unsaturated polyester resin
WO2010108965A1 (en) 2009-03-25 2010-09-30 Dsm Ip Assets B.V. Unsaturated polyester resin
CN102361909A (en) * 2009-03-25 2012-02-22 帝斯曼知识产权资产管理有限公司 Process for preparing unsaturated polyester
WO2010108962A1 (en) 2009-03-25 2010-09-30 Dsm Ip Assets B.V. Unsaturated polyester resin composition
US20120157618A1 (en) * 2009-03-25 2012-06-21 Marian Henryk Szkudlarek Unsaturated polyester resin
WO2010108966A1 (en) * 2009-03-25 2010-09-30 Dsm Ip Assets B.V. Process for preparing unsaturated polyester
CN102361905B (en) * 2009-03-25 2013-11-06 帝斯曼知识产权资产管理有限公司 Unsaturated polyester resin
CN102361909B (en) * 2009-03-25 2013-11-06 帝斯曼知识产权资产管理有限公司 Process for preparing unsaturated polyester
CN106519135A (en) * 2016-12-03 2017-03-22 安徽富丽华化工有限公司 Modified unsaturated polyester resin with low viscosity and corrosion resistance and preparation method of modified unsaturated polyester resin
CN106589749A (en) * 2016-12-03 2017-04-26 安徽富丽华化工有限公司 Modified unsaturated polyester resin having excellent acid and alkali resistance, and preparation method thereof

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