GB692022A - Improved body cleansing agents - Google Patents

Improved body cleansing agents

Info

Publication number
GB692022A
GB692022A GB8545/49A GB854549A GB692022A GB 692022 A GB692022 A GB 692022A GB 8545/49 A GB8545/49 A GB 8545/49A GB 854549 A GB854549 A GB 854549A GB 692022 A GB692022 A GB 692022A
Authority
GB
United Kingdom
Prior art keywords
aqueous solution
c2h4nh
solution
brought
addition
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
GB8545/49A
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.)
Evonik Operations GmbH
Original Assignee
TH Goldschmidt AG
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 TH Goldschmidt AG filed Critical TH Goldschmidt AG
Publication of GB692022A publication Critical patent/GB692022A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0047—Other compounding ingredients characterised by their effect pH regulated compositions
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Detergent Compositions (AREA)

Abstract

A cleansing composition having disinfectant properties (see Groups III and VI) is prepared by adjusting to a pH of 5-8 an aqueous solution of a salt formed between an acid and a substance of general formula R1NHR2COOH, where R1 is an aliphatic radicle containing more than 10 carbon atoms and R2 is a divalent aliphatic, aromatic or aliphatic-aromatic radicle. Radicle R1 may consist of a hydrocarbon chain or such a chain interrupted by NH or CONH. Preferred substances of the above general formula are (a) RCONH(C2H4NH)nR2COOH, where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2 or C2H4, and (b) RNH(C2H4NH) nR2COOH, where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2, C6H4, C6H3OH or CH2.C6 H3OH. In the examples: (1) 1 mole of coconut oil fatty acids is heated with 1.5 mole triethylene tetramine and the mono-acrylated triethylene tetramine is removed from the reaction mixture by fractional distillation; this mono-acylated material is reacted with chloracetic acid in aqueous solution to give a solution of the monohydrochloride of RCONH(C2H4NH)3CH2 COOH, where R corresponds to the hydrocarbon radicle of coconut oil fatty acids, and HCl is added to bring the pH to 6-7; (2) a mixture of equal proportions of C12-C16 alkyl chlorides is reacted with a large excess of ethylene diamine, soda lye is added to the reaction product and the monoalkylated ethylene diamine is removed by fractional distillation; this monoalkylated material is condensed in aqueous solution with sodium chloroacetate and HCl is added to the solution to give the monohydrochloride of RNHCH2CH2NHCH2 COOH, where R corresponds to mixed C12-C16 alkyl radicles, in a solution of pH 5-6; (3) dodecyl chloride is reacted with diethylene tetramine, soda lye is added to the reaction product and the mono-alkylated diethylamine tetramine is removed by fractional distillation; this mono-alkylated material is condensed in aqueous solution with sodium chloroacetate and lactic acid is added to the solution to give the monolactate of C12H25NH(C2H4NH)2CH2COOH in a solution of pH 7.5; (4) tetradecyl chloride is reacted with diethylene triamine, soda lye is added to the reaction product and the monoalkylated diethylene triamine is removed by fractional distillation; this mono-alkylated material is reacted in aqueous solution with phenyl monochloroacetic acid and HCl is added to the solution to give the mono-hydrochloride of C14H29NH(C2H4NH)2CH(C6H5 COOH in a solution of pH 6; (5) the monoalkylated material of (4) is reacted in aqueous solution with sodium o-chlorobenzoate and acetic acid is added to the solution to give the monoacetate of C14H29NH(C2H4NH)2C6H4 COOH in a solution of pH 7-8 and (6) hexadecyl chloride is reacted with diethylene triamine, soda lye is added to the reaction product and the mono-alkylated diethylene triamine is removed by fractional distillation; this mono-alkylated material is reacted in aqueous solution with p-chloromethyl salicylic acid and HCl is added to the solution to give the monohydrochloride of C16H33NH(C2H4 NH)2CH2C6H3(OH)COOH in a solution of pH 7.5. The Specification as open to inspection under Sect. 91, refers to the use of the aqueous solutions without adjustment of pH. This subject-matter does not appear in the Specification as accepted. p ALSO:A cleansing composition having disinfectant properties is prepared by adjusting to a pH of 5-8 an aqueous solution of a salt formed between an acid and a substance of general formula R1NHR2COOH, where R1 is an aliphatic radicle containing more than 10 carbon atoms and R2 is a divalent aliphatic, aromatic or aliphatic-aromatic radicle. Radicle R1 may consist of a hydrocarbon chain or such a chain interrupted by NH or CONH. Preferred substances of the above general formula are (a) RCONH(C2H4NH)nR2COOH where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2 or C2H4 and (b) RNH(C2H4NH)nR2COOH where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2, C6H4, C6H3OH or CH2C6H3OH. In the examples, (1) a 10 per cent aqueous solution of the monohydrochloride of RCONH(C2H4NH)3CH2COOH, where R corresponds to the hydrocarbon radicle of coconut oil fatty acids, is brought to a pH of 6-7 by addition of hydrochloric acid, (2) a 15 per cent aqueous solution of the monohydrochloride of RNHCH2CH2NHCH2COOH where R corresponds to mixed C12-C16 alkyl radicles, is brought to a pH of 5-6 by addition of hydrochloric acid, (3) a 15 per cent aqueous solution of the monolactate of C12H25NH(C2H4NH)2CH2COOH is brought to a pH of 7.5 by addition of lactic acid, (4) a 10 per cent aqueous solution of the monohydrochloride of C14H29NH(C2H4 NH)2CH(C6H5)COOH is brought to a pH of 6 by addition of hydrochloric acid, (5) a 15 per cent aqueous solution of the monoacetate of C14H29NH(C2H4NH)2C6H4COO is brought to a pH of 7-8 by addition of acetic acid, and (6) a 15 per cent aqueous solution of the monohydrochloride of C16H33NH(C2H4NH)2CH2C6 H3(OH)COOH is brought to a pH of 7.5 by addition of hydrochloric acid. The Specification as open to inspection under Sect. 91 refers to the use of the aqueous solutions without adjustment of pH. This subject matter does not appear in the Specification as accepted.ALSO:A cleansing composition having disinfectant properties is prepared by adjusting to a pH of 5-8 an aqueous solution of a salt formed between an acid and a substance of general formula R1NHR2COOH, where R1 is an aliphatic radicle containing more than 10 carbon atoms and R2 is a divalent aliphatic, aromatic or aliphatic-aromatic radicle. Radicle R1 may consist of a hydrocarbon chain or such a chain interrupted by NH or CONH. Preferred substances of the above general formula are (a) RCONH(C2H4NH)nR2COOH where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2 or C2H4 and (b) RNH (C2H4NH)nR2COOH where R is a hydrocarbon chain of about 12-18 carbon atoms, n is 1, 2 or 3 and R2 is CH2, C6H4, C6H3OH or CH2.C6H3OH. In the examples (1) a 10 per cent aqueous solution of the monohydrochloride of RCONH (C2H4NH)3CH2COOH, where R corresponds to the hydrocarbon radicle of coconut oil fatty acids is brought to a pH of 6-7 by addition of hydrochloric acid, (2) a 15 per cent aqueous solution of the monohydrochloride of RNHCH2CH2 NHCH2COOH where R corresponds to mixed C12-C16 alkyl radicles, is brought to a pH of 5-6 by addition of hydrochloric acid, (3) a 15 per cent aqueous solution of the monolactate of C12H25NH(C2H4NH)2CH2COOH is brought to a pH of 7.5 by addition of lactic acid, (4) a 10 per cent aqueous addition of the monohydrochloride of <FORM:0692022/VI/1> is brought to a pH of 6 by addition of hydrochloric acid, (5) a 15 per cent aqueous solution of the monoacetate of C14H29NH(C2H4NH) 2C6H4COOH is brought to a pH of 7-8 by addition of acetic acid and (6) a 15 per cent aqueous solution of the monohydrochloride of C16H33NH(C2H4NH)2CH2 C6H3(OH)COOH is brought to a pH of 7.5 by addition of hydrochloric acid. The Specification as open to inspection under Sect. 91, refers to the use of the aqueous solutions without adjustment of pH. This subject-matter does not appear in the Specification as accepted.
GB8545/49A 1949-01-27 1949-03-29 Improved body cleansing agents Expired GB692022A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE862477T 1949-01-27

Publications (1)

Publication Number Publication Date
GB692022A true GB692022A (en) 1953-05-27

Family

ID=6090182

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8545/49A Expired GB692022A (en) 1949-01-27 1949-03-29 Improved body cleansing agents

Country Status (6)

Country Link
BE (1) BE491152A (en)
CH (1) CH295840A (en)
DE (1) DE862477C (en)
FR (2) FR1013537A (en)
GB (1) GB692022A (en)
NL (1) NL71045C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802785A (en) * 1954-08-30 1957-08-13 Union Oil Co Water flooding process
US2802784A (en) * 1954-08-30 1957-08-13 Union Oil Co Water flooding of subterranean formations
US3235457A (en) * 1962-12-07 1966-02-15 Gillette Co Humectant
US3717579A (en) * 1970-10-05 1973-02-20 Goldschmidt Ag Th Biocidal preparation

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2755191A (en) * 1952-07-31 1956-07-17 Goldschmidt Ag Th Manufacture of bactericidal clear ice
DE1024325B (en) * 1952-10-31 1958-02-13 Colgate Palmolive Co Method of preserving food
DE1047975B (en) * 1956-08-06 1958-12-31 Goldschmidt Ag Th Means for simultaneous body cleaning and disinfection
US3093591A (en) * 1957-05-03 1963-06-11 Gen Mills Inc Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
DE1184770C2 (en) * 1961-06-01 1965-09-02 Hoffmann La Roche Process for the production of antibacterially active peptides
DE3528209C2 (en) * 1984-08-07 1993-10-28 Fresenius Ag disinfectant
CN109289696B (en) * 2018-10-29 2022-03-22 天津先光化工有限公司 Preparation method of imidazoline amphoteric surfactant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE714585C (en) * 1935-08-17 1941-12-03 Ig Farbenindustrie Ag Process for the production of nitrogenous products
DE662451C (en) * 1935-08-17 1938-07-13 I G Farbenindustrie Akt Ges Process for the preparation of nitrogen-containing compounds from alkyleneimines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802785A (en) * 1954-08-30 1957-08-13 Union Oil Co Water flooding process
US2802784A (en) * 1954-08-30 1957-08-13 Union Oil Co Water flooding of subterranean formations
US3235457A (en) * 1962-12-07 1966-02-15 Gillette Co Humectant
US3717579A (en) * 1970-10-05 1973-02-20 Goldschmidt Ag Th Biocidal preparation

Also Published As

Publication number Publication date
NL71045C (en) 1952-10-15
FR1000684A (en) 1952-02-14
FR1013537A (en) 1952-07-30
DE862477C (en) 1953-01-12
BE491152A (en) 1949-09-30
CH295840A (en) 1954-01-15

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