GB949249A - Sulphonation products of epoxidised higher molecular weight compounds - Google Patents

Sulphonation products of epoxidised higher molecular weight compounds

Info

Publication number
GB949249A
GB949249A GB35022/61A GB3502261A GB949249A GB 949249 A GB949249 A GB 949249A GB 35022/61 A GB35022/61 A GB 35022/61A GB 3502261 A GB3502261 A GB 3502261A GB 949249 A GB949249 A GB 949249A
Authority
GB
United Kingdom
Prior art keywords
weight
oil
sulphonating
oils
agents
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
GB35022/61A
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.)
Boehme Fettchemie GmbH
Original Assignee
Boehme Fettchemie GmbH
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 Boehme Fettchemie GmbH filed Critical Boehme Fettchemie GmbH
Publication of GB949249A publication Critical patent/GB949249A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G99/00—Subject matter not provided for in other groups of this subclass
    • C07G99/002—Compounds of unknown constitution containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • C14C3/14—Fat tanning; Oil tanning
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613—Polyethers without nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6136—Condensation products of esters, acids, oils, oxyacids with oxiranes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2219/042—Sulfate esters
    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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
    • C10N2050/10—Semi-solids; greasy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Paper (AREA)
  • Lubricants (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Epoxidised unsaturated organic compounds containing 10 to 26 carbon atoms per molecule, and an epoxy oxygen content of up to 3% by weight, are sulphonated with sulphuric acid, of another sulphonating agent, present in an amount of more than 20% by weight of the epoxy compound. Preferably the epoxy starting material contains 0.1-3, especially 0.8-1.5% of epoxy oxygen. Indicated sulphonating agents are sulphuric acid, with or without a dehydrating agent such as acetic anhydride, phosphoric acid or phosphorus pentoxide, sulphur trioxide and pyridine sulphuric acid adduct. Amounts of sulphonating agent specified are 20 to 40, preferably 25 to 35%. The washed product is neutralised with e.g. ammonia, sodium or potassium hydroxide or an alkanolamine. Indicated unsaturated compounds are alcohols, ether, carboxylic acids, esters and amides and especially animal, vegetable or synthetic oils, fatty acid derivatives thereof, or waxes, especially teaseed, rape, olive, neats' foot, sperm, seal sardine and shak oils, glycerine trioleate, esters, of fatty acids with fatty alcohols e.g. dioleyl adipate, linseed oil alcohol phthalate and interesterification products from castor oil with unsaturated alcohols. Epoxidation is effected as in the parent Specification. The products are wetting, dispersing, emulsifying, washing, cleaning and rinsing agents and may also be used as tanning, bleaching and fat-liquoring oils for leather and artificial leather, and in the manufacture of paper, pasteboard and cardboard (see Divisions C5, C6 and D1). Examples are provided of the preparation of the sulphonates and their use in textile, leather and paper treatments.ALSO:Surface-active compounds made by sulphonating epoxidized unsaturated organic compounds having from 10 to 26 carbon atoms per molecule, and an epoxy oxygen content of up to 3% by weight, with more than 20% by weight of a sulphonating agent (see Division C2), are neutralized, e.g. with ammonia, NaOH, KOH or an alkanolamine, and used, alone or together with ethylene oxide condensation products, as emulsifying agents for mineral oil greases. Example (4) shows soluble and cutting oils containing, based on mineral oil, 0.3-20% by weight of sulphonated epoxidized neat's foot oil, and Examples (8), (9) and (11) show water-emulsifiable compositions containing respectively sulphonated castor, rape and shark oils added in the proportion of 6 to 4 by weight to mineral oils.ALSO:Surface active compounds made by sulphonating an epoxidized unsaturated organic compound having from 10 to 26 carbon atoms per molecule, and an epoxy oxygen content of up to 3% by weight, with more than 20% by weight of a sulphonating agent (see Division C2) are used in the treatment of leather. The compounds may be used in amounts of 4-6% by weight of fat-liquoring agents, tanning and bleaching oils in conjunction with vegetable tanning and also as plasticizing and thickening agents in leather finishing compositions. Examples show the use of products from sperm oil, glycerine trioleate, teaseed oil, a wax made from oleic acid and cetyl alcohol, castor oil, herring oil and shark oil as fat-liquoring, softening, plasticizing and dispersing agents in the leather industry.ALSO:A glazed coating is obtained on paper by using, in the coating colour, a surface active compound made by sulphonating an epoxidation product of an unsaturated organic compound having 10 to 26 carbon atoms per molecule, and an epoxy oxygen content of up to 3% by weight, the sulphonating agent being employed in an amount of more than 20% by weight, calculated on the epoxidation product; and neutralizing the acidic product. Example 7 shows the use of a sulphonated castor oil epoxide.ALSO:Surface active compounds made by sulphonating epoxidised unsaturated organic compounds having from 10 to 26 carbon atoms per molecule, and an epoxy oxygen content of up to 3% by weight, with more than 20% of a sulphonating agent (see Division C2) are used, after neutralisation, in dyeing natural and regenerated cellulose as wetting and levelling agents and finishing textiles, in sizes based on starch, albumen or cellulose derivatives, and in the manufacture of paper, cardboard and pasteboard. Indicated unsaturated compounds are mainly animal, vegetable and synthetic oils, or fatty acid derivatives thereof, or waxes. In Example 1 sulphonated epoxidised sperm oil is used in the bath liquor in dyeing artificial silk and cotton and in Example 7 a product from castor oil is used as a 5 to 10% by weight addition to a coating colour used to produce a glazed paper.
GB35022/61A 1960-05-04 1961-09-29 Sulphonation products of epoxidised higher molecular weight compounds Expired GB949249A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1960B0057714 DE1198815C2 (en) 1960-05-04 1960-05-04 PROCESS FOR THE PRODUCTION OF SURFACE-ACTIVE SULFUR ACID ESTERS AND THEIR SALT
DE1418650A DE1418650B2 (en) 1960-05-04 1960-12-24 Process for the production of surface-active sulfuric acid esters or their salts

Publications (1)

Publication Number Publication Date
GB949249A true GB949249A (en) 1964-02-12

Family

ID=25965640

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9751/61A Expired GB932300A (en) 1960-05-04 1961-03-17 Process for the preparation of surface-active esters of inorganic polybasic acids
GB35022/61A Expired GB949249A (en) 1960-05-04 1961-09-29 Sulphonation products of epoxidised higher molecular weight compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB9751/61A Expired GB932300A (en) 1960-05-04 1961-03-17 Process for the preparation of surface-active esters of inorganic polybasic acids

Country Status (6)

Country Link
CH (2) CH388935A (en)
DE (2) DE1198815C2 (en)
GB (2) GB932300A (en)
IT (1) IT649680A (en)
NL (1) NL271858A (en)
SE (1) SE310361B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110055754A (en) * 2019-05-07 2019-07-26 四川丝玛帛科技有限公司 Softness lubrication graft modification silk and preparation method thereof and fat liquor

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3617657C2 (en) * 1986-05-26 1994-08-18 Stockhausen Chem Fab Gmbh Room temperature liquid derivatives of natural fats or oils, process for their preparation, and their use
DE4231073A1 (en) * 1992-09-17 1994-03-24 Rhein Chemie Rheinau Gmbh Phosphorylation of epoxides
CN116103451A (en) * 2023-03-30 2023-05-12 精艺裘皮制品股份有限公司 Multi-working-procedure effective synergistic beach sheepskin harmless tanning method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE969930C (en) * 1954-05-06 1958-07-31 Henkel & Cie Gmbh Process for the production of higher molecular weight compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110055754A (en) * 2019-05-07 2019-07-26 四川丝玛帛科技有限公司 Softness lubrication graft modification silk and preparation method thereof and fat liquor
CN110055754B (en) * 2019-05-07 2021-08-10 四川丝玛帛科技有限公司 Soft lubricating grafted modified silk, preparation method thereof and grease emulsion

Also Published As

Publication number Publication date
DE1198815C2 (en) 1975-12-04
GB932300A (en) 1963-07-24
DE1198815B (en) 1965-08-19
NL271858A (en)
DE1418650B2 (en) 1978-05-03
CH412865A (en) 1966-05-15
CH388935A (en) 1965-03-15
DE1418650A1 (en) 1969-10-09
IT649680A (en)
SE310361B (en) 1969-04-28

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