GB859489A - Improvements in and relating to modified polyethylene terephthalate - Google Patents

Improvements in and relating to modified polyethylene terephthalate

Info

Publication number
GB859489A
GB859489A GB31644/58A GB3164458A GB859489A GB 859489 A GB859489 A GB 859489A GB 31644/58 A GB31644/58 A GB 31644/58A GB 3164458 A GB3164458 A GB 3164458A GB 859489 A GB859489 A GB 859489A
Authority
GB
United Kingdom
Prior art keywords
formula
give
polyethylene terephthalate
dimethyl
acid
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
GB31644/58A
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 US688431A external-priority patent/US3032534A/en
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB859489A publication Critical patent/GB859489A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6886—Dicarboxylic acids and dihydroxy 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
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used

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)

Abstract

A polyethylene terephthalate is modified to give it improved dyeability by including in its molecule a minor proportion of structural units having the formula: <FORM:0859489/IV(a)/1> where R is an alkylene radical containing 1-5 carbon atoms. The modified polyethylene terephthalate is made by heating a mixture of ethylene glycol, a dialkyl terephthalate and a sulphone dicarboxylic ester of formula: <FORM:0859489/IV(a)/2> (where R1 is an alkyl radical) at 100 DEG -200 DEG C. to effect ester interchange and then polymerizing the resulting glycol esters by heating at 200 DEG -300 DEG C. Catalysts for the reaction are calcium, sodium, magnesium acetate, dibutyl tin oxide, tributyl tin hydroxide, dilauryl tin oxide, dibutyl tin dichloride or the borate, salicylate, benzoate, carbonate or acetate of lead. Examples describe the manufacture of modified polyethylene terephthalates from ethylene glycol, dimethyl terephthalate and either dimethyl 4, 41-[sulphonylbis-(trimethylene)] dibenzoate or dimethyl 4, 41-sulphonylditoluate. Specification 578,079 is referred to.ALSO:Diesters of formula : <FORM:0859489/IV(b)/1> where R is an alkylene radical containing 1-5 carbon atoms and R1 is an alkyl radical which forms an alcohol boiling at below about 200 DEG C. are made by the following series of reactions :-(1) An aralkyl chloride of formula Cl R C6 H5 is reacted with acetyl chloride in the presence of aluminium chloride as a catalyst and carbon disulphide as the reaction medium to give (2) the corresponding acetophenone of formula Cl R C6H4CO CH3 which is oxidised with alkaline hyporbromite solution and acidified with hydrochloric acid to give (3) the corresponding benzoic acid of formula Cl R C6H4 COOH which is reacted with sodium sulphide to form (4) the 4, 41-(thiodialkylene) dibenzoic acid of formula HOOC C6H4RSR C6H4COOH which is oxidised with peracetic acid to give (5) the sulphonyl dibenzoic acid formula HOOC C6H4R SO2 R C6 H4COOH which is esterified with an alcohol of formula R1OH to give (6) the desired product. The diesters are used to modify polyethylene terephthalate, (see Group IV(a)).
GB31644/58A 1957-10-07 1958-10-03 Improvements in and relating to modified polyethylene terephthalate Expired GB859489A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US859489XA 1957-10-07 1957-10-07
US1215665XA 1957-10-07 1957-10-07
US688431A US3032534A (en) 1957-10-07 1957-10-07 Sulfone-modified polyethylene terephthalate

Publications (1)

Publication Number Publication Date
GB859489A true GB859489A (en) 1961-01-25

Family

ID=27375165

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31644/58A Expired GB859489A (en) 1957-10-07 1958-10-03 Improvements in and relating to modified polyethylene terephthalate

Country Status (2)

Country Link
FR (1) FR1215665A (en)
GB (1) GB859489A (en)

Also Published As

Publication number Publication date
FR1215665A (en) 1960-04-20

Similar Documents

Publication Publication Date Title
US2319576A (en) Peroxidized ester
GB849109A (en) Method of preparing esters
GB793907A (en) Linear polyesters of terephthalic acid and a process of producing them
GB1130387A (en) Ester interchange reactions
US2393327A (en) Esters
GB949085A (en) Catalyst system for use in the manufacture of linear fibre and film-forming polyesters
GB997398A (en) Phosphorus-containing fibre-forming polyesters
GB859489A (en) Improvements in and relating to modified polyethylene terephthalate
GB955232A (en) Improvements in or relating to the preparation of macromolecular polymethylene terephthalates
GB978172A (en) Improvements in or relating to the preparation of diesters of phthalic acids
GB1024487A (en) A new bicyclic glycol and polyesters made therefrom
GB835442A (en) Glycol esters of terephthalic acid
GB747031A (en) Process for preparing polyester amides
GB775316A (en) Polyglycol terephthalates and isophthalates
GB1416446A (en) Sperm oil
GB1100753A (en) Improvements in polyesterification catalysts
GB1107234A (en) Production of acrylate and methacrylate esters
US3255236A (en) Ester-ester interchange in the presence of an aluminum alkyl catalyst
US2867650A (en) Process for the preparation of monodiol esters of terephthalic acid
GB873862A (en) Improvements in the dyeing properties of polyethylene terephthalate
GB651762A (en) Improvements in and relating to the production of polymeric esters
GB1006579A (en) Polyester of improved dyeability
GB773538A (en) Improvements in the production of linear polyesters
GB1005996A (en) Process for the production of optically brightened polyesters of terephthalic acid
GB795782A (en) Manufacture of highly polymeric polymethylene terephthalates