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GB1007819A - Improvements in and relating to sulfophenoxy, sulfophenylthio and sulfophenyl-sulfonyl-substituted alkanoic acids, salts and esters and their use in dyeable polyesters - Google Patents

Improvements in and relating to sulfophenoxy, sulfophenylthio and sulfophenyl-sulfonyl-substituted alkanoic acids, salts and esters and their use in dyeable polyesters

Info

Publication number
GB1007819A
GB1007819A GB4092862A GB4092862A GB1007819A GB 1007819 A GB1007819 A GB 1007819A GB 4092862 A GB4092862 A GB 4092862A GB 4092862 A GB4092862 A GB 4092862A GB 1007819 A GB1007819 A GB 1007819A
Authority
GB
United Kingdom
Prior art keywords
sulpho
acid
methyl
acetate
sulphonyl
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
GB4092862A
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 US149196A external-priority patent/US3116321A/en
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB1007819A publication Critical patent/GB1007819A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

A dyeable linear polyester is made from an aromatic dicarboxylic acid or dialkyl ester thereof, a diol or a diester thereof, and 0.1-5 mole per cent of a compound of formula <FORM:1007819/C3/1> in which M is an alkali metal, Y is an oxygen or sulphur atom or a sulphonyl group, n is an integer of from 1 to 12, and R is a hydrogen or alkyl radical containing from 1 to 8 carbon atoms. Suitable dicarboxylic acid compounds are monocyclic aromatic dicarboxylic acids and their di-alkyl esters containing 1-8 carbon atoms in each alkyl group. Aromatic diacids specified include phthalic and terephthalic acids. Suitable diols are acyclic and alicyclic aliphatic glycols containing 2-10 carbon atoms, aliphatic/aromatic diols and aromatic diols. Diols specified include ethylene glycol, 1,4-bis-(hydroxymethyl) cyclohexane, ethylene oxide and 2,2,4,4-tetra-methyl-cyclobutane-1,3-diol. Up to 10 moles of diol may be used per mole of acid. Sulphonated compounds specified include methyl (4 - [sodium sulpho]phenoxy) acetate, methyl 6 - (4 - [sodium sulpho]phenoxy) hexanoate, methyl 6-(4-[sodium sulpho]phenyl thio) hexanoate, methyl 8 - (4 - [potassium sulpho]phenyl thio] octanoate, butyl (4 - [lithium sulpho]phenyl thio) acetate, butyl (4-[potassium sulpho]phenoxy) acetate, ethyl 8-(4-[lithium sulpho]phenoxy) octanoate, methyl (4 - [lithium sulpho]phenyl sulphonyl) octanoate, methyl 6 - (4 - [sodium sulpho]phenyl sulphonyl) hexanoate, methyl 8 - (4 - [lithium sulpho] sulphonyl) octanoate, butyl 6 - (4-[potassium sulpho] phenyl sulphonyl) hexanoate, ethyl (4 - [potassium sulpho] phenyl sulphonyl) acetate, ethyl (4 - [potassium sulpho] phenyl thio) acetate. Up to 10 mole per cent of the dicarboxylic acid or diol may be replaced by another monomer of similar difunctionality or by a hydroxycarboxylic acid. Copolymerizable acids specified include: azelaic, sebacic and 3,6-dimethyl sebacic. As comonomers there can also be used compounds of formula: <FORM:1007819/C3/2> where p = 1-12 and Y1 is H or MSO3, e.g. dimethyl 2-(potassium sulpho) fluorene-9,9-dipropionate or dimethyl 2,7-di-(lithium sulpho) fluorene-9,9-dipropionate. Another class of comonomer is represented by the formula: <FORM:1007819/C3/3> where Ar1 is aromatic, e.g. dimethyl 5-(4-[sodium sulpho] phenoxy ethoxy) iso-phthalate. 0.001-1% of a catalyst, e.g. zinc acetate sodium hexabutyl titanate or Sb2O3, may be present during the reaction. Other additives may be colour inhibitors, pigments, delustrants, and viscosity stabilizers. The polyester may be made either by heating the reactants in an inert atmospher (a) at 150-270 DEG C., (b) at 300 DEG C. under reduced pressure to remove the excess diol and (c) at 225-325 DEG C./0.1-5 mm. Hg to polymerize or by carrying out all three stages at atmospheric pressure in an inert gas stream. The products may be made into fibres, films, textile and moulded articles. Specifications 1,006,578 and 1,007,820 are referred to.ALSO:The invention comprises compounds of the formula <FORM:1007819/C2/1> wherein X is an -SO3H or an -SO3M radical, M being an alkali metal atom, Y is an oxygen atom, sulphur atom or a sulphonyl radical, n is an integer from 1 to 12, and R is a hydrogen atom or an alkyl radical of 1 to 8 carbon atoms. The novel compounds may be made by reacting a compound of the general formula <FORM:1007819/C2/2> with a sulphonating agent comprised of a mixture of sulphuric acid and acetic anhydride, preferably in the ratio of from 0.1 : 1 to 1 : 1. The ratio of sulphuric acid to starting material is preferably from 0.5 : 1 to 5 : 1. Suitable temperatures are in the range from -15 DEG to 50 DEG C. An inert solvent such as methylene dichloride, ethylene dichloride or ethyl acetate may be used. The compound in which Y is -SO2- can also be made by oxidizing the corresponding sulphonated phenylthioalkanoic acid or ester, e.g. with peracetic acid or hydrogen peroxide, preferably in dimethylformamide, acetone or ethyl acetate, at temperatures from 30 DEG to 100 DEG C. The metallosulpho derivatives may be obtained by reacting the sulphonated compounds with an alkali metal hydroxide or alkoxide, or an alkali metal salt of an acid weaker than sulphonic acid to form the corresponding alkali metal salt, for example at 5-110 DEG C. in alcoholic or aqueous solution. The phenylthioalkanoic acids and esters can be obtained by the reaction of an alkali metal thiophenolate with a haloalkanoic acid or ester. Specifications 1,006,578 and 1,007,820 are referred to.
GB4092862A 1961-11-01 1962-10-30 Improvements in and relating to sulfophenoxy, sulfophenylthio and sulfophenyl-sulfonyl-substituted alkanoic acids, salts and esters and their use in dyeable polyesters Expired GB1007819A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14923361A 1961-11-01 1961-11-01
US149196A US3116321A (en) 1961-11-01 1961-11-01 Sulfoaromatic-substituted alkanoic acids and derivatives thereof

Publications (1)

Publication Number Publication Date
GB1007819A true GB1007819A (en) 1965-10-22

Family

ID=26846541

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4092862A Expired GB1007819A (en) 1961-11-01 1962-10-30 Improvements in and relating to sulfophenoxy, sulfophenylthio and sulfophenyl-sulfonyl-substituted alkanoic acids, salts and esters and their use in dyeable polyesters

Country Status (1)

Country Link
GB (1) GB1007819A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2339593A1 (en) * 1976-02-02 1977-08-26 Diamond Shamrock Corp NEW ALKYLPHENOXY-ALCANOIC SULPHONIC ACIDS AND THEIR APPLICATION AS UNIFORMISING AGENTS FOR COLORING
EP0177014A3 (en) * 1984-10-03 1987-05-27 Teijin Limited Modified polyester fiber and process for preparation thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2339593A1 (en) * 1976-02-02 1977-08-26 Diamond Shamrock Corp NEW ALKYLPHENOXY-ALCANOIC SULPHONIC ACIDS AND THEIR APPLICATION AS UNIFORMISING AGENTS FOR COLORING
EP0177014A3 (en) * 1984-10-03 1987-05-27 Teijin Limited Modified polyester fiber and process for preparation thereof

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