GB873862A - Improvements in the dyeing properties of polyethylene terephthalate - Google Patents

Improvements in the dyeing properties of polyethylene terephthalate

Info

Publication number
GB873862A
GB873862A GB15804/59A GB1580459A GB873862A GB 873862 A GB873862 A GB 873862A GB 15804/59 A GB15804/59 A GB 15804/59A GB 1580459 A GB1580459 A GB 1580459A GB 873862 A GB873862 A GB 873862A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
disulphonyl
dicaproate
acid
ester
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
GB15804/59A
Inventor
Christian Friedrich Horn
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 US688394A external-priority patent/US3036995A/en
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Priority to GB15804/59A priority Critical patent/GB873862A/en
Priority to FR795096A priority patent/FR1224703A/en
Publication of GB873862A publication Critical patent/GB873862A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Linear polyethylene terephthalate containing in its molecule 1-20 mol per cent of structural units -OOCRSO2R1-SO2RCOO- where R and R1 are divalent hydrocarbon radicals containing 2-10 carbon atoms are prepared by including in the ester-interchange reaction between ethylene glycol and a lower alkyl terephthalate the appropriate amount of R1(SO2RCOOR11)2 wher R11 is the residue of an alcohol boiling below 200 DEG C. Suitable disulphones are dimethyl 6, 61-(tetramethylene disulphonyl) dicaproate; dimethyl 4, 41-(tetramethylene disulphonyl) dibutyrate; dimethyl 6, 61-(p-xylylene-disulphonyl) dicaproate; dimethyl 4, 41-(tetramethylene disulphonyl) dibenzoate; dimethyl 6, 61- (ethylene disulphonyl) dicaproate; dimethyl, 4, 41-(trimethylenedisulphonyl) ditoluate; dimethyl 6, 61-(pentamethylene disulphonyl) dicaproate; dimethyl 6, 61-(hexamethylene disulphonyl) dicaproate; dimethyl 6, 61-(decamethylene disulphonyl) dicaproate; dimethyl 4, 41-(3-methyl pentamethylene disulphonyl) ditoluate; dimethyl 4, 41-(decamethylene disulphonyl) ditoluate; dimethyl 6, 61-(3-methylpentamethylene disulphonyl) dicaproate; dimethyl 4, 41-(p-xylylene disulphonyl) dibutyrate; dimethyl 5, 51-(p-xylylene disulphonyl) divalerate; dimethyl 6, 61-(trimethylene disulphonyl) dicaproate. Usual ester interchange catalysts e.g. sodium, calcium, dibutyl tin oxide, tributyl tin hydroxide, dilauryl tin oxide, dibutyl tin chloride, or lead borate, salicylate, benzoate, carbonate or acetate may be used in the first stage of reaction. Polycondensation is continued until filaments or films formed from the melt can be cold-drawn. The products have improved dyeing properties. U.S.A. Specification 2,465,319 is referred to.ALSO:Disulphones of formula R1(SO2RCOOR11)2 where R and R1 are divalent hydrocarbon radicals with 2-10 carbon atoms and R11 is H or a residue of an alcohol boiling below 200 DEG C. may be prepared by reacting R1Cl2 with HSRCOOH, oxidising the dithio acid to the disulphone acid and esterifying the latter, or by reacting R1(SH)2 with a butyro, valero or caprolactone or the corresponding o -halogen acids to form a dithiodicarboxylic acid which is then oxidised and esterified. In an example, 1,4-dichlorobutane is reacted with 6-mercaptocaproic acid or its methyl ester to form 6,61-(tetramethylenedithio)-dicaproic acid or its dimethyl ester. Oxidation, e.g. with peracetic acid yields the corresponding disulphone diester or diacid, which latter may be esterified to form the methyl ester.
GB15804/59A 1957-10-07 1959-05-08 Improvements in the dyeing properties of polyethylene terephthalate Expired GB873862A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB15804/59A GB873862A (en) 1957-10-07 1959-05-08 Improvements in the dyeing properties of polyethylene terephthalate
FR795096A FR1224703A (en) 1957-10-07 1959-05-20 Polyethylene terephthalate compositions capable of being dyed

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US688394A US3036995A (en) 1957-10-07 1957-10-07 Sulfone-modified polyethylene terephthalate
GB15804/59A GB873862A (en) 1957-10-07 1959-05-08 Improvements in the dyeing properties of polyethylene terephthalate
FR795096A FR1224703A (en) 1957-10-07 1959-05-20 Polyethylene terephthalate compositions capable of being dyed

Publications (1)

Publication Number Publication Date
GB873862A true GB873862A (en) 1961-07-26

Family

ID=27245270

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15804/59A Expired GB873862A (en) 1957-10-07 1959-05-08 Improvements in the dyeing properties of polyethylene terephthalate

Country Status (2)

Country Link
FR (1) FR1224703A (en)
GB (1) GB873862A (en)

Also Published As

Publication number Publication date
FR1224703A (en) 1960-06-27

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