GB1016396A - Improvements in or relating to polyester resins - Google Patents

Improvements in or relating to polyester resins

Info

Publication number
GB1016396A
GB1016396A GB3779462A GB3779462A GB1016396A GB 1016396 A GB1016396 A GB 1016396A GB 3779462 A GB3779462 A GB 3779462A GB 3779462 A GB3779462 A GB 3779462A GB 1016396 A GB1016396 A GB 1016396A
Authority
GB
United Kingdom
Prior art keywords
acid
diol
maleic anhydride
dimethylpropane
anhydride
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
GB3779462A
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.)
Hoechst AG Werk Kalle Albert
Original Assignee
Chemische Werke Albert
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 Chemische Werke Albert filed Critical Chemische Werke Albert
Publication of GB1016396A publication Critical patent/GB1016396A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6828—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Polyesters are made by reacting a high molecular weight polyester of terephthalic acid and a dihydric alcohol with (a) a dicarboxylic acid (other than terephthalic acid) or an anhydride, monoester, diester or oligomeric ester thereof and (except where reactant (a) is an ester which contains at least an equivalent amount of polyhydric alcohol units in relation to dicarboxylic acid units) (b) a polyhydric alcohol. Preferably the terephthalic acid polyester is first heated with one of the reactants to effect solution thereof and the other reactant is then added and heating continued. The reaction mixture may also include a monohydric alcohol, a monocarboxylic acid (e.g. a resinic acid, a fatty acid containing 12-22 carbon atoms, or benzoic acid) or a polycarboxylic acid containing more than two carboxyl groups (e.g. pyromellitic acid) or a hydroxycarboxylic acid (e.g. ricinoleic or hydryxoystearic acid). The reaction may be effected in the presence of a solvent, e.g. an aliphatic, aromatic or terpenic hydrocarbon. Specified dicarboxylic acids are maleic, fumaric, itaconic, citraconic, mesaconic, tetrahydrophthalic, endomethylene tetrahydrophthalic, chlorendic, endomethylene hexahydrophthalic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, phthalic, imphthalic, hexahydro-, ortho-, iso- or tere-phthalic, tri- or tetra-chlorophthalic or tetrachlorosuccinic acids. Specified polyhydric alcohols are ethylene, 1:2- or 1:3-propylene-, diethylene- or triethylene-glycol; a butanediol, pentanedial or hexanediol; 2:2-dimethylpropane-1:3-diol, 2-ethyl - 2 - butyl - propane - 1:3 - diol, 1:4-butenediol, hydrogenated bis-phenol A, partially etherified or acetalized products of alcohol containing at least three hydroxy groups; dimethylol benzene, toluene or xylene; and addition products of ethylene oxide, propylene oxide or butylene oxide with the above dihydric alcohols or with dihydric phenols. In addition to the above dihydric alcohols small amounts of higher polyhydric alcohols may be used, e.g. glycerol, trimethylol ethane, trimethylol propane or hexanetriol. The polyesters containing residues from unsaturated dicarboxylic acid may be copolymerized with unsaturated monomers, e.g. styrene and its substitution products, vinyl esters, allyl esters, vinyl pyrrolidone, divinyl benzene, esters of acrylic or methacrylic acid, or acrylonitrile. Copolymerization may be effected in the presence of the usual catalysts and accelerators. Examples describe the manufacture of polyesters by reacting polyethylene terephthalate with (1) maleic anhydride and 1:2-propanediol; (2) maleic anhydride, phthalic anhydride and 1:2-propanediol; (3) dibutyl maleate and 2:2 - dimethylpropane - 1:3 - diol; (4) 2:2-dimethylpropane - 1:3 - diol, fumaric acid and phthalic anhydride; (5) 2:2-dimethylpropane-1:3-diol, phthalic anhydride and maleic anhydride; (6) 1:3-butanediol, phthalic anhydride and maleic anhydride; (7) 2:2-dimethyl-propane-1:3-diol, chlorendic anhydride and maleic anhydride; (8) adipic acid, 2:2-dimethylpropane-1:3-diol and maleic anhydride; (9) and (10) maleic anhydride and 1:2-propane-diol; (11) and (12) 2:2-dimethylpropane-1:3-diol, maleic anhydride and either pentaerythritol diallyl ether or trimethylolpropane monallyl ether; (13) and (14) 2:2-dimethylpropane-1:3-diol, ricinoleic acid or hydroxystearic acid and maleic anhydride; (15) 2:2-dimethylpropane-1:3-diol, phthalic anhydride and maleic anhydride. The polyesters of Example (1) are dissolved in a mixture of ethylene glycol monethyl ether and ethylene glycol monoethyl ether acetate to form a coating composition. The polyesters of Examples (1), (2), (7), (8), (9), (10), (12) and (14) (possibly after stabilization with hydroquinone) were copolymerized with styrene using as a catalyst either benzoyl peroxide or a mixture of cyclohexanone peroxide and cobalt napthenate. In Examples (1) and (14) copolymerization was effected in the presence of glass fibres. The polyester of Example (15) could be used as a plasticizer for unsaturated polyesters.
GB3779462A 1961-10-12 1962-10-05 Improvements in or relating to polyester resins Expired GB1016396A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEC0025265 1961-10-12
DEC0027791 1962-08-27
DE1962C0027792 DE1495251B2 (en) 1961-10-12 1962-08-27 PROCESS FOR THE PROCESSING OF WASTE FROM DIFFICULT, HIGH MOLECULAR TEREPHTHALIC ACID DIOLESTERN
DE1963C0029117 DE1495282B2 (en) 1961-10-12 1963-02-09 PROCESS FOR THE PROCESSING OF WASTE FROM DIFFICULT, HIGH MOLECULAR ISOPHTHALIC ACID DIOLESTERS

Publications (1)

Publication Number Publication Date
GB1016396A true GB1016396A (en) 1966-01-12

Family

ID=27436693

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3779462A Expired GB1016396A (en) 1961-10-12 1962-10-05 Improvements in or relating to polyester resins
GB549464A Expired GB1022270A (en) 1961-10-12 1964-02-10 Improvements in or relating to polyester resins

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB549464A Expired GB1022270A (en) 1961-10-12 1964-02-10 Improvements in or relating to polyester resins

Country Status (7)

Country Link
US (1) US3427267A (en)
CH (1) CH438734A (en)
DE (3) DE1495251B2 (en)
GB (2) GB1016396A (en)
LU (2) LU42884A1 (en)
NL (2) NL130565C (en)
SE (1) SE332076C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009223A2 (en) * 1978-09-14 1980-04-02 Mitsubishi Kasei Corporation Photosensitive composition
WO2000024802A1 (en) * 1998-10-26 2000-05-04 Sun Chemical Corporation Reclaimed poly(ethylene terephthalate) coating

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1720424A1 (en) * 1967-12-08 1971-09-23 Albert Ag Chem Werke Process for the multi-stage production of curable fatty acid-modified polycondensates based on telomerizates
US3761434A (en) * 1971-04-30 1973-09-25 Cities Service Oil Co Petroleum hydrocarbon compositions
US3866373A (en) * 1972-07-06 1975-02-18 Westinghouse Electric Corp Pultruded shapes containing hollow glass or ceramic spheres
JPS5029953B2 (en) * 1972-08-31 1975-09-27
US3947423A (en) * 1973-06-11 1976-03-30 Fmc Corporation Polyesters containing bicyclic phosphate flame retardant
US4054713A (en) * 1973-12-28 1977-10-18 Kao Soap Co., Ltd. Process for preparing glass fiber mats
BR7600329A (en) * 1975-01-20 1976-08-31 Hooker Chemicals Plastics Corp FUSION POLYMERIZATION PROCESS FOR PREPARATION OF LINEAR AROMATIC POLYESTERS AND POLYESTERES PREPARED BY THE SAME
US4096102A (en) * 1975-01-27 1978-06-20 Owens-Corning Fiberglas Corporation Moldable compositions comprising thermosetting polyester resin and thermoplastic resin
US4054561A (en) * 1975-01-27 1977-10-18 Owens-Corning Fiberglas Corporation Thermoplastic additives for molding compounds
US4113704A (en) * 1976-06-24 1978-09-12 Monsanto Company Polyester filament-forming polymer and its method of production
US4158083A (en) * 1976-07-02 1979-06-12 Basf Wyandotte Corporation Fibrous article sized with a branched water-dispersible polyester
US4193896A (en) * 1977-04-04 1980-03-18 Kemerica, Incorporated Process for modifying linear polymer resins
US4205115A (en) * 1978-04-19 1980-05-27 Ppg Industries, Inc. Polyester coating composition
US4215026A (en) * 1979-01-02 1980-07-29 Basf Wyandotte Corp. Aqueous dispersion of a branched polyester
US4259478A (en) * 1979-12-14 1981-03-31 Eastman Kodak Company Process for preparing high molecular weight copolyesters
US4539341A (en) * 1984-02-22 1985-09-03 Jim Walter Resources, Inc. Digestion products of polyalkylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom
US4873268A (en) * 1984-02-22 1989-10-10 Sloss Industries Corporation Digestion products of polyalkylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom
US4758607A (en) * 1985-07-18 1988-07-19 Sloss Industries Corporation Distilled products of polyethylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom
US4853419A (en) * 1985-07-18 1989-08-01 Sloss Industries Corporation Distilled products of polyethylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom
DE4019087C3 (en) * 1989-06-29 2001-01-18 Frische Gmbh Novel plastics based on fatty acids
JPH04501124A (en) * 1989-08-09 1992-02-27 ドクトル　フリッシェ　ゲーエムベーハー Novel monomer suitable for plastic production
US5756554A (en) * 1996-02-02 1998-05-26 Ashland Inc. Low profile additives for polyester resin systems based on asymmetric glycols and aromatic diacids
WO2006113175A2 (en) * 2005-04-13 2006-10-26 INVISTA TECHNOLOGIES, S.à r.l. Oxygen scavenging compositions and method of preparation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA490032A (en) * 1953-01-27 Lewis Heath Royden Degradation of aromatic polyesters
US2933476A (en) * 1955-09-30 1960-04-19 Du Pont Polymerization process
NL239840A (en) * 1958-06-16
BE583950A (en) * 1958-10-24
US3039980A (en) * 1959-07-17 1962-06-19 American Cyanamid Co Process for preparing resinous materials
US3160679A (en) * 1959-11-09 1964-12-08 California Research Corp Unsaturated polyester flexible films
US3196131A (en) * 1960-09-22 1965-07-20 Staudard Oil Company Process of preparing unsaturated polyester resins
NL301426A (en) * 1962-12-06

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009223A2 (en) * 1978-09-14 1980-04-02 Mitsubishi Kasei Corporation Photosensitive composition
EP0009223A3 (en) * 1978-09-14 1980-09-03 Mitsubishi Chemical Industries Limited Photosensitive composition
WO2000024802A1 (en) * 1998-10-26 2000-05-04 Sun Chemical Corporation Reclaimed poly(ethylene terephthalate) coating

Also Published As

Publication number Publication date
SE332076B (en) 1971-01-25
NL284022A (en) 1900-01-01
DE1495251A1 (en) 1969-01-16
LU45369A1 (en) 1964-08-06
DE1495251B2 (en) 1976-12-02
LU42884A1 (en) 1963-02-18
DE1495250A1 (en) 1969-03-13
CH438734A (en) 1967-06-30
SE332076C (en) 1976-06-14
DE1495282B2 (en) 1977-05-12
NL130565C (en) 1900-01-01
GB1022270A (en) 1966-03-09
DE1495282A1 (en) 1969-03-27
US3427267A (en) 1969-02-11

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