GB1087415A - Novel surface-active betaines and preparation and use thereof - Google Patents

Novel surface-active betaines and preparation and use thereof

Info

Publication number
GB1087415A
GB1087415A GB23486/63A GB2348663A GB1087415A GB 1087415 A GB1087415 A GB 1087415A GB 23486/63 A GB23486/63 A GB 23486/63A GB 2348663 A GB2348663 A GB 2348663A GB 1087415 A GB1087415 A GB 1087415A
Authority
GB
United Kingdom
Prior art keywords
alkyl
chx
aqueous
agents
ocph2p
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
GB23486/63A
Inventor
Adolf Koebner
Herbert Alexander Potts
Brodie David Proudfoot
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.)
Marchon Products Ltd
Original Assignee
Marchon Products Ltd
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 Marchon Products Ltd filed Critical Marchon Products Ltd
Priority claimed from GB25137/63A external-priority patent/GB1084739A/en
Publication of GB1087415A publication Critical patent/GB1087415A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/75Amino oxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/90Betaines

Landscapes

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

Abstract

Detergent compositions comprise 1-25% by weight of a compound of formula <FORM:1087415/C4-C5/1> where Z is C8- 18 alkyl or alkenyl, or alkylphenyl of 6-16 carbon atoms in the alkyl substituent, p in each oxyalkylene group is 2 or 3, x is 2-20, R1 is C1- 4 alkyl or -(CqH2qO)yH (where q in each oxyalkylene group is 2 or 3 and y is 1-20), R2 is as R1 or Z(OCpH2p)x-, or R1 and R2 together with the nitrogen atom form a 5- or 6-membered heterocyclic ring, and B is -(CHX)2CO2-, (CHX)2SO3-or -(CHX)2OSO3-(where X is hydrogen or one may be CH2 or OH, and z is 1-4); except that when Z is alkyl-phenyl B is not -CH2CO2- (see Division C2); together with at least one anionic or non-ionic surface-active agent. A liquid detergent composition also consists of or contains an essential mixture comprising 5-90% by weight of a compound as defined above, and 10-95% by weight of water-soluble anionic surface-active agents, which are of formula RC6H4SO3M and/or ROSO3M and/or R(OC2H4)nOSO3M and/or R1C6H4(OC2H4)nOSO3M, where R is C8- 18 alkyl, R1 is C6- 16 alkyl, n has an average value of 1-10, and M is a cation. An aqueous or aqueous-alcoholic medium may be present, the essential mixture comprising 8-20% by weight of the total compositions. The compositions may also contain as foam stabilizer an alkylolamide of a C8- 18 fatty acid and/or a compound of formula <FORM:1087415/C4-C5/2> where Z, R1, R2 and p are as defined above, m is 0-10, in total amount not more than 30% by weight of the essential mixture. The compositions may also contain colouring agents, perfumes, hair-conditioning agents such as lanolin, germicidal or medication agents such as hexachlorophene or 2,2,4-trichlorocarbanilide, opacifying agents such as ethylene or propylene gylcol monostearates, thickening agents such as a colloidal or a water-soluble salt of a fatty acid of at least 10 carbon atoms, boosters such as alkylolamides; sodium tripolyphosphate, tetrapotassium pyrophosphate, soda ash, sodium sulphate, sodium metasilicate, sequestering agents such as salts of aminopolycarboxylic acids; hydrotropes such as sodium toluene or xylene sulphonate, and solvents such as alcohols. Inorganic sulphates will be present as impurities in organic sulphates used.ALSO:The invention comprises compounds of the formula <FORM:1087415/C2/1> where Z is C8- 18 alkyl or alkenyl, or alkylphenyl of 6-16 carbon atoms in the alkyl substituent, p in each oxyalkylene group is 2 or 3, x is 2-20, R1 is C1- 4 alkyl or -(CpH2pO)zH (where q in each oxyalkylene group is 2 or 3 and y is 1-20), R2 is as R1 or is Z(OCpH2p)x-, or R1 and R2 together with the nitrogen atom form a 5- or 6-membered heterocyclic ring, and B is -(CHX)2CO2-(CHX)2SO3- or -(CHX)2OSO3-, where X is hydrogen or one of the X's present may be CH3 or OH and z is 1-4; with the proviso that when Z is alkylphenyl, B is not -CH2CO2-; and their preparation by (i) reacting Z(OCpH2p)xNR1R2 with Cl(CHX)2CO2M, Cl(CHX)xSO3M or Cl(CHX)zOSO3M, where M is a cation, by heating in an aqueous or aqueous-alcoholic medium at up to 100 DEG C., e.g. at pH 7.5-9.0; (ii) (for B as -(CH2)zSO3-, where z is 3 or 4) reacting Z(OCpH2p)xNR1R2 with propane or butane sultone in aqueous, alcoholic or aqueous-alcoholic medium at up to 100 DEG C.; (iii) (for B as -CqH2qOSO3-, R1 as C1- 4 alkyl, R2 the same as R1 or -CqH2qOH) monosulphating Z(OCpH2p)xN(R12)CqH2qOH (where R1 is H or an R2 group, neutralizing the product with a non-nitrogenous base, and reacting the resulting ester with a quaternating agent. Lauryl dioxyethylene 2 - hydroxyethylamine is prepared from lauryl dioxyethylene sulphate and monoethanolamine. The compounds of the invention are surfaceactive (see Division C5).
GB23486/63A 1963-06-25 1963-06-25 Novel surface-active betaines and preparation and use thereof Expired GB1087415A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB23484/64A GB1087413A (en) 1963-06-25 1963-06-25 Improvements in or relating to amines
GB25137/63A GB1084739A (en) 1963-06-25 1963-06-25 Surface-active compositions
GB2330464 1964-06-04

Publications (1)

Publication Number Publication Date
GB1087415A true GB1087415A (en) 1967-10-18

Family

ID=48608396

Family Applications (3)

Application Number Title Priority Date Filing Date
GB23484/64A Expired GB1087413A (en) 1963-06-25 1963-06-25 Improvements in or relating to amines
GB23486/63A Expired GB1087415A (en) 1963-06-25 1963-06-25 Novel surface-active betaines and preparation and use thereof
GB23485/64A Expired GB1087414A (en) 1963-06-25 1963-07-22 Improvements in or relating to amine oxides as surfaceactive agents

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB23484/64A Expired GB1087413A (en) 1963-06-25 1963-06-25 Improvements in or relating to amines

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB23485/64A Expired GB1087414A (en) 1963-06-25 1963-07-22 Improvements in or relating to amine oxides as surfaceactive agents

Country Status (2)

Country Link
CA (1) CA721771A (en)
GB (3) GB1087413A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208345A (en) * 1977-03-01 1980-06-17 Sandoz Ltd. 2-Hydroxy-n-propylamine derivatives useful as surface active agents
JPS6089458A (en) * 1983-10-22 1985-05-20 Toho Chem Ind Co Ltd Ampholytic surface-active betaine compound and production thereof
GB2168364A (en) * 1984-12-14 1986-06-18 Sandoz Ltd Sulphates of oxyalkylated amines and their use as dyeing assistants
EP0582209A1 (en) * 1992-08-03 1994-02-09 BASF Aktiengesellschaft Alkoxylation products and their use as dispesion agents
WO2005092952A1 (en) * 2004-03-19 2005-10-06 The Procter & Gamble Company Process of sulfating select polymers
WO2012170908A1 (en) * 2011-06-08 2012-12-13 Life Technologies Corporation Design and development of novel detergents for use in pcr systems
US9914964B2 (en) 2013-10-25 2018-03-13 Life Technologies Corporation Compounds for use in PCR systems and applications thereof
US10378050B2 (en) 2011-06-08 2019-08-13 Life Technologies Corporation Polymerization of nucleic acids using proteins having low isoelectric points

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2942156A1 (en) * 1979-10-18 1981-04-30 Hoechst Ag, 6000 Frankfurt SLIMING AGENT
DE3028016A1 (en) * 1980-07-24 1982-02-25 Hoechst Ag, 6000 Frankfurt PREPARATION AGENTS FOR SYNTHESIS FIBERS AND THE USE THEREOF
ZA832561B (en) * 1982-04-13 1983-12-28 Albright & Wilson Amine oxide formulations
EP0112593B1 (en) * 1982-12-23 1989-07-19 THE PROCTER &amp; GAMBLE COMPANY Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
DE3504242A1 (en) 1985-02-08 1986-08-14 Henkel KGaA, 4000 Düsseldorf METHOD FOR PRODUCING TERTIAL ETHERAMINES
EP0227720A1 (en) * 1985-06-22 1987-07-08 Henkel Kommanditgesellschaft auf Aktien Washing agent for low washing temperatures
DE3623215A1 (en) * 1986-07-10 1988-01-21 Henkel Kgaa NEW QUARTERS OF AMMONIUM COMPOUNDS AND THEIR USE
DE3623730A1 (en) * 1986-07-14 1988-01-21 Henkel Kgaa NEW QUARTERS OF AMMONIUM COMPOUNDS AND THEIR USE
US5292954A (en) * 1990-05-17 1994-03-08 Ethyl Corporation Amine oxide composition and process
EP0898560A1 (en) * 1996-04-18 1999-03-03 The Procter & Gamble Company Syntheses of substituted amines
WO2001017945A1 (en) * 1999-09-03 2001-03-15 The Procter & Gamble Company Cationic alkyl alkoxylate derivatives

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208345A (en) * 1977-03-01 1980-06-17 Sandoz Ltd. 2-Hydroxy-n-propylamine derivatives useful as surface active agents
JPS6089458A (en) * 1983-10-22 1985-05-20 Toho Chem Ind Co Ltd Ampholytic surface-active betaine compound and production thereof
JPH0460102B2 (en) * 1983-10-22 1992-09-25 Toho Chem Ind Co Ltd
GB2168364A (en) * 1984-12-14 1986-06-18 Sandoz Ltd Sulphates of oxyalkylated amines and their use as dyeing assistants
EP0582209A1 (en) * 1992-08-03 1994-02-09 BASF Aktiengesellschaft Alkoxylation products and their use as dispesion agents
US5424445A (en) * 1992-08-03 1995-06-13 Basf Aktiengesellschaft Alkoxylation products
WO2005092952A1 (en) * 2004-03-19 2005-10-06 The Procter & Gamble Company Process of sulfating select polymers
US7550621B2 (en) 2004-03-19 2009-06-23 The Procter & Gamble Company Process of sulfating select polymers
US9493414B2 (en) 2011-06-08 2016-11-15 Life Technologies Corporation Development of novel detergents for use in PCR systems
US10202639B2 (en) 2011-06-08 2019-02-12 Life Technologies Corporation Development of novel detergents for use in PCR systems
US8980333B2 (en) 2011-06-08 2015-03-17 Life Technologies Corporation Development of novel detergents for use in PCR systems
CN103796987B (en) * 2011-06-08 2016-09-21 生命技术公司 The design of novel detergent and exploitation for PCR system
WO2012170908A1 (en) * 2011-06-08 2012-12-13 Life Technologies Corporation Design and development of novel detergents for use in pcr systems
CN106518696A (en) * 2011-06-08 2017-03-22 生命技术公司 Design and development of novel detergents for use in pcr systems
US11697841B2 (en) 2011-06-08 2023-07-11 Life Technologies Corporation Development of novel detergents for use in PCR systems
CN103796987A (en) * 2011-06-08 2014-05-14 生命技术公司 Design and development of novel detergents for use in pcr systems
EP3461807A1 (en) * 2011-06-08 2019-04-03 Life Technologies Corporation Design and development of novel detergents for use in pcr systems
CN106518696B (en) * 2011-06-08 2019-06-14 生命技术公司 The design and exploitation of novel detergent for PCR system
US10378050B2 (en) 2011-06-08 2019-08-13 Life Technologies Corporation Polymerization of nucleic acids using proteins having low isoelectric points
US10676785B2 (en) 2011-06-08 2020-06-09 Life Technologies Corporation Development of novel detergents for use in PCR systems
US11365443B2 (en) 2011-06-08 2022-06-21 Life Technologies Corporation Polymerization of nucleic acids using proteins having low isoelectric points
US10683539B2 (en) 2013-10-25 2020-06-16 Life Technologies Corporation Compounds for use in PCR systems and applications thereof
US11479814B2 (en) 2013-10-25 2022-10-25 Life Technologies Corporation Compounds for use in PCR systems and applications thereof
US9914964B2 (en) 2013-10-25 2018-03-13 Life Technologies Corporation Compounds for use in PCR systems and applications thereof

Also Published As

Publication number Publication date
GB1087414A (en) 1967-10-18
CA721771A (en) 1965-11-16
GB1087413A (en) 1967-10-18

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