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GB446568A - Processes for improving the wetting properties of aqueous liquids used for treating textiles and other fibrous materials - Google Patents

Processes for improving the wetting properties of aqueous liquids used for treating textiles and other fibrous materials

Info

Publication number
GB446568A
GB446568A GB21908/34A GB2190834A GB446568A GB 446568 A GB446568 A GB 446568A GB 21908/34 A GB21908/34 A GB 21908/34A GB 2190834 A GB2190834 A GB 2190834A GB 446568 A GB446568 A GB 446568A
Authority
GB
United Kingdom
Prior art keywords
acid
sulphonated
bisulphite
esters
esterified
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
GB21908/34A
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.)
Selden Co
Original Assignee
Selden Co
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 Selden Co filed Critical Selden Co
Publication of GB446568A publication Critical patent/GB446568A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/46—Textile oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/04—Protein or carboxylic compound containing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

Esters having the formula <FORM:0446568/IV/1> in which R is an aliphatic carbon chain, Me is hydrogen or a metal or a basic group, X is hydrogen or an alcohol or phenol residue and Y is an alcohol or phenol residue, are used in the treatment of textiles and other fibrous materials with aqueous liquids. The esters may be prepared by treating the ester of an unsaturated aliphatic dicarboxylic acid with an alkali bisulphite or by esterification of the sulphonated saturated acids. Mixtures of esters and mixed esters derived from maleic acid and other acids with mono or polyhydric alcohols or alkylene oxides, e.g. propylene or butylene oxide may be used. Mixed octylamyl and ethoxyethylamyl esters are mentioned. Sulphochlorsuccinic, sulphosebacic, sulphodimethylsuccinic, sulphomethylglutaric, sulphopimelic sulphopropylsuccinic, sulphooctyl glutaric acids are suitable starting materials for the esterification. The products are stated to be wetting, detergent, dispersing and lubricating agents, and may be used in dye preparations, emulsions of fats, oils, shellac, gums and natural and synthetic resins, in finishing, saponaceous, waterproofing, coating, lubricating and mordanting compositions, in rosin, casein and starch compositions and in preparations for treating paper and pulp products. Their use in mercerizing lyes and baths for degumming silk and impregnating wood is mentioned. In examples: (1) esters derived from the following alcohols and maleic acid or anhydride are sulphonated by treatment with sodium bisulphite: amyl, capryl, octyl, tetrahydrofurfuryl, stearyl and oleyl alcohols, ethyleneglycolmonobutylether, glycerine, and ethylene glycol; (2) fumaric acid is esterified with 2-ethylhexanol and sulphonated with sodium bisulphite to give dioctylsulphosuccinate; (3) glutaconic acid is esterified with cyclohexanol and sulphonated with sodium bisulphite; (4) mesoconic acid dichloride is treated with sodium phenolate in toluene and the mesoconic acid diphenylester sulphonated with bisulphite to give sodium diphenylsulphopyrotartrate; (5) an ester product prepared from ethyleneoxide and maleic acid is sulphonated with bisulphite; (6) mixed esters derived from glycerine and maleic and acetic acid anhydrides are sulphonated with bisulphite; (7) a mixed ester derived from maleic anhydride, oleic acid, glycerine and amyl alcohol is sulphonated with bisulphite; the product, on drying, is a soft resin; (8) an acid ester obtained from amyl alcohol and phthalic anhydride or succinic, chlormalic or tartaric acid is esterified with glycerine and the product further esterified with maleic anhydride and finally sulphonated with bisulphite; (9) glycerine is esterified with phthalic anhydride or benzoic or benzoylbenzoic acid and the product further esterified in tetrahydronaphthalene with maleic anhydride; (10) a neutral ester obtained from castor oil and maleic anhydride is sulphonated with bisulphite; (11) an acid ester of maleic acid and castor oil is prepared and sulphonated with bisulphite; to increase its solubility it may be treated with caustic alkali or further sulphonated with sulphuric acid. The following alcohols and phenols may be used in the preparation of the esters: methyl, ethyl and propyl alcohols, the amyl alcohol obtained by hydrolysis of the halogenated pentane fraction of natural gas, methylcyclohexanol, borneol, menthyl alcohol, furfuryl alcohol, cresols, xylenols and naphthols, polyglycerols, pentaerythrite and propylene and butyleneglycols. The esters may be used in the form of their soluble salts. The following bases are mentioned: alkali metals, ammonia, mono-, di-and tri-methyl and ethylamine, triethanolamine, pyridine, nicotine, cinchona alkaloids and basic dyes. The fact that the salts of the esters with alkaloids give dispersions in aqueous media facilitates their use as mothproofing agents; the nicotine and pyridine salts are useful as insecticides. The production of the following esters by direct esterification of the sulphodicarboxylic acids with the alcohols is described: dimethylsulphomaleate, dilaurylsulpho succinate, difenchylsulphosuccinate, diethoxyethyl sulphopyrotartrate, dibenzylsulphoadipate, the sulphosuberate of methylisobutylcarbinol and dibutylsulphosebacate. The Specification as open to inspection under Sect. 91 comprises also the use of the esters in colour lakes, solvents for fats, printing and writing inks, automobile, metal, furniture and shoe creams, in carbonizing and fat liquoring and in emulsions of perfumes, cosmetics, shaving creams, shampoos, petroleum (kerosene and naphtha), rubber, asphaltic paints, varnishes, shellac, pigments, germicides and in fire extinguishing emulsions and emulsions of boring, wire-drawing and cutting (lathe) oils. This subject-matter does not appear in the Specification as accepted.ALSO:Esters having the formula <FORM:0446568/III/1> in which R is an aliphatic carbon chain, Me is hydrogen or a metal or a basic group, X is hydrogen or an alcohol or phenol residue and Y is an alcohol or phenol residue, are used as emulsifying agents in the treatment of textiles and other fibrous materials. Mixtures of esters and mixed esters derived from maleic acid and other acids with mono- or polyhydric alcohols or alkylene oxides, e.g. propylene or butylene oxide may be used. Mixed octylamyl and ethoxyethylamyl esters are mentioned. Sulphochlorsuccinic, sulphosebasic, sulphodimethylsuccinic, sulphomethylglutaric, sulphopimelic, sulphopropylsuccinic and sulphooctyl glutaric acid are suitable starting materials for the esterification. The products may be used in emulsions of fats, oils, shellac, gums and natural and synthetic resins and in rosin, casein and starch compositions. In examples: (1) esters derived from the following alcohols and maleic acid or anhydride are sulphonated by treatment with sodium bisulphite amyl, capryl, octyl, tetrahydrofurfuryl, stearyl and oleyl alcohols, ethyleneglycolmonobutylether, glycerine, and ethylene glycol; (2) fumaric acid is esterified with 2-ethylhexanol and sulphonated with sodium bisulphite to give dioctylsulphosuccinate; (3) glutaconic acid is esterified with cyclohexanol and sulphonated with sodium bisulphite; (4) mesoconic acid dichloride is treated with sodium phenolate and the mesoconic acid diphenylester sulphonated with bisulphite to give sodium diphenylsulphopyrotartrate; (5) an ester product prepared from ethyleneoxide and maleic acid is sulphonated with bisulphite; (6) mixed esters derived from glycerine and maleic and acetic acid anhydrides are sulphonated with bisulphite; (7) a mixed ester derived from maleic anhydride, oleic acid, glycerine and amylalcohol is sulphonated with bisulphite; the product, on drying is a soft resin; (8) an acid ester obtained from amyl alcohol and phthalic anhydride or succinic, chlormalic or tartaric acid is esterified with glycerine and the product further esterified with maleic anhydride and finally sulphonated with bisulphite; (9) glycerine is esterified with phthalic anhydride or benzoic or benzoylbenzoic acid and the product further esterified with maleic anhydride; (10) a neutral ester obtained from castor oil and maleic anhydride is sulphonated with bisulphite; (11) an acid ester of maleic acid and castor oil is sulphonated with bisulphite; to increase its solubility it may be treated with caustic alkali or further sulphonated with sulphuric acid. The following alcohols and phenols may be used in the preparation of the esters: methyl, ethyl and propyl alcohols, the amyl alcohol obtained by hydrolysis of the halogenated pentane fraction of natural gas, methylcyclohexanol, borneol, menthyl p alcohol, furfuryl alcohol, cresols, xylenols and naphthols, polyglycerols, pentaerythrite and propylene and butyleneglycols. The esters may be used in the form of their soluble salts. The following bases are mentioned: alkali metals, ammonia, monodi- and tri-methyl and ethylamine, triethanolamine, pyridine, nicotine, cinchona alkaloids and basic dyes. The production of the following esters by direct esterification of the sulphodicarboxylic acids with the alcohols is described: dimethylsulphomaleate, dilaurylsulphosuccinate, difenchylsulphosuccinate, diethoxyethyl sulphopyrotartrate, dibenzylsulphoadipate, the sulphosuberate of methylisobutylcarbinol and dibutylsulphosebacate. The Specification as open to inspection under Sect. 91 comprises also the use of the esters in colour lakes, solvents for fats, printing and writing inks, automobile metal, furniture and shoe creams, in carbonizing and fat liquoring and in emulsions of perfumes, cosmetics, shaving creams, shampoos, petroleum (kerosene and naphtha), rubber, asphatic paints, varnishes, shellac pigments, germicides and in fire extinguishing emulsions and emulsions of boring, wire-drawing and cutting (lathe) oils. This subject-matter does not appear in the Specification as accepted.
GB21908/34A 1933-07-28 1934-07-26 Processes for improving the wetting properties of aqueous liquids used for treating textiles and other fibrous materials Expired GB446568A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US682629A US2028091A (en) 1933-07-28 1933-07-28 Esters of sulphodicarboxylic acids

Publications (1)

Publication Number Publication Date
GB446568A true GB446568A (en) 1936-04-27

Family

ID=24740498

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21908/34A Expired GB446568A (en) 1933-07-28 1934-07-26 Processes for improving the wetting properties of aqueous liquids used for treating textiles and other fibrous materials

Country Status (3)

Country Link
US (1) US2028091A (en)
FR (1) FR776495A (en)
GB (1) GB446568A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0054191A2 (en) * 1980-12-12 1982-06-23 Allied Corporation Wetting solution for use in continuous dyeing of polyamide fabric
EP0054191A3 (en) * 1980-12-12 1982-11-03 Allied Corporation Wetting solution for use in continuous dyeing of polyamide fabric

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US2028091A (en) 1936-01-14
FR776495A (en) 1935-01-26

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