GB1087413A - Improvements in or relating to amines - Google Patents

Improvements in or relating to amines

Info

Publication number
GB1087413A
GB1087413A GB23484/64A GB2348464A GB1087413A GB 1087413 A GB1087413 A GB 1087413A GB 23484/64 A GB23484/64 A GB 23484/64A GB 2348464 A GB2348464 A GB 2348464A GB 1087413 A GB1087413 A GB 1087413A
Authority
GB
United Kingdom
Prior art keywords
alkylolamine
alkyl
formula
amine
reacting
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
GB23484/64A
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
Priority to CA721771A priority Critical patent/CA721771A/en
Application filed by Marchon Products Ltd filed Critical Marchon Products Ltd
Priority to GB23486/63A priority patent/GB1087415A/en
Priority to GB23484/64A priority patent/GB1087413A/en
Priority claimed from GB25137/63A external-priority patent/GB1084739A/en
Priority to GB23485/64A priority patent/GB1087414A/en
Publication of GB1087413A publication Critical patent/GB1087413A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • 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
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Landscapes

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

Abstract

Amines of the formula <FORM:1087413/C3/1> where Z is a C8- 18 alkyl or alkenyl group or an alkylphenyl group possessing an alkyl substituent having from 6 to 16 carbons, R is -(CqH2qO)xH, Z(OCpH2p)n- or C1- 4 alkyl, p is 2 or 3, q is 2 or 3, n is 2-9 and x is 1-20, provided that when Z is alkylphenyl, the amine contains at least one hydroxy-propyl or condensed hydroxypropyl group, may be obtained by reacting an organic sulphate ester of the formula Z(OCpH2p)nOSO3M, where M is a cation, with an alkylolamine of the formula <FORM:1087413/C3/2> where R1 is the same as R or a hydrogen atom, in the presence of a solvolytic medium and a base at a temperature of at least 100 DEG C., and optionally reacting the tertiary amine product with ethylene and/or propylene oxide to increase the value of x to not more than 20. The solvolytic medium employed in the process is a highly polar liquid which is a solvent for the organic sulphate; it is preferably an excess of the alkylolamine reactant, but an aqueous medium containing a dissolved base, e.g. a tertiary amine or an alkali metal hydroxide or carbonate, or dimethyl sulphoxide, sulpholane or C10- 20 alcohols may also be used. The cation M in the monosulphate is preferably an alkylolammonium ion derived from the reactant alkylolamine. The optional second stage of the process may be effected by reacting the tertiary amine product from the first stage with the required molar amount of ethylene or propylene oxide or a mixture thereof, preferably under superatmospheric pressure and generally at 50-200 DEG C. in the presence of a catalyst, e.g. a Lewis acid or a base.ALSO:Amines of the formula <FORM:1087413/C2/1> where Z is C8- 18 alkyl or alkenyl or an alkylphenyl group possessing an alkyl substituent having from 6 to 16 carbons, R is -(CqH2qO)xH, Z(OCpH2p)n- or C1- 4 alkyl, p is 2 or 3, q is 2 or 3, n is 2 to 9, x is 1-20, provided that when Z is alkyl phenyl, the amine contains at least one hydroxy propyl or condensed hydroxypropyl group, may be obtained by reacting an organic sulphate ester of the formula Z(OCpH2p)nOSO3M, where M is a cation, with an alkylolamine of the formula <FORM:1087413/C2/2> where R1 is the same as R or a hydrogen atom, in the presence of a solvolytic medium and a base at a temperature of at least 100 DEG C., and optionally reacting the tertiary amine product with ethylene and/or propylene oxide to increase the value of x to not more than 20. The solvolytic medium employed in the process is a highly polar liquid which is a solvent for the organic sulphate; it is preferably an excess of the alkylolamine reactant, but an aqueous medium containing a dissolved base, e.g. a tertiary amine or an alkali metal hydroxide or carbonate, or dimethyl sulphoxide, sulpholane and C10- 20 alcohols may also be used. The cation M in the monosulphate is preferably an alkylolammonium ion derived from the reactant alkylolamine. The optional second stage of the process may be effected by reacting the tertiary amine product from the first stage with the required molar amount of ethylene oxide, propylene oxide or mixture thereof, preferably under superatmospheric pressure and generally at 50-200 DEG C. in the presence of a catalyst, e.g. a Lewis acid or a base. In examples, lauryltrioxyethylene bis - (2 - hydroxy ethyl)amine, p - nonyl phenyltetraoxyethylenebis - (2 - hydroxyethyl)amine, lauryl-trioxyethylene bis-(2 - hydroxypropy)amine and lauryl - trioxypropylene bis - (2 - hydroxyethyl)amine are prepared; other compounds of the invention are also specified.
GB23484/64A 1963-06-25 1963-06-25 Improvements in or relating to amines Expired GB1087413A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA721771A CA721771A (en) 1963-06-25 Surface-active agents and preparation and use thereof
GB23486/63A GB1087415A (en) 1963-06-25 1963-06-25 Novel surface-active betaines and preparation and use thereof
GB23484/64A GB1087413A (en) 1963-06-25 1963-06-25 Improvements in or relating to amines
GB23485/64A GB1087414A (en) 1963-06-25 1963-07-22 Improvements in or relating to amine oxides as surfaceactive agents

Applications Claiming Priority (3)

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

Publications (1)

Publication Number Publication Date
GB1087413A true GB1087413A (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 After (2)

Application Number Title Priority Date Filing Date
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

Country Status (2)

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

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0190708A1 (en) 1985-02-08 1986-08-13 Henkel Kommanditgesellschaft auf Aktien Process for the preparation of tertiary ether amines
GB2175597A (en) * 1982-12-23 1986-12-03 Procter & Gamble Ethoxylated mono-amines
EP0252441A2 (en) * 1986-07-10 1988-01-13 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds and their application
EP0253275A1 (en) * 1986-07-14 1988-01-20 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds and their use
US4820436A (en) * 1985-06-22 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Detergents for low laundering temperatures
US5292954A (en) * 1990-05-17 1994-03-08 Ethyl Corporation Amine oxide composition and process
WO2001017946A1 (en) * 1999-09-03 2001-03-15 The Procter & Gamble Company Tertiary alkyl alkoxylate derivatives and the composition thereof

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2807130A1 (en) * 1977-03-01 1978-09-07 Sandoz Ag AMPHOTIC AND ANIONIC SURFACTANTS, THEIR PRODUCTION AND USE
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
IE55226B1 (en) * 1982-04-13 1990-07-04 Albright & Wilson Amine oxide formulations
JPS6089458A (en) * 1983-10-22 1985-05-20 Toho Chem Ind Co Ltd Ampholytic surface-active betaine compound and production thereof
FR2574791A1 (en) * 1984-12-14 1986-06-20 Sandoz Sa FATTY AMINO ACID SULFATES, THEIR PREPARATION AND THEIR USE AS AUXILIARY PRODUCTS
DE4225619A1 (en) * 1992-08-03 1994-02-10 Basf Ag Alkoxylation products
WO1997038968A1 (en) * 1996-04-18 1997-10-23 The Procter & Gamble Company Syntheses of substituted amines
JP2007529612A (en) * 2004-03-19 2007-10-25 ザ プロクター アンド ギャンブル カンパニー Method for sulfating selected polymers
US9567628B2 (en) 2011-06-08 2017-02-14 Life Technologies Corporation Polymerization of nucleic acids using proteins having low isoelectric points
EP3461807B1 (en) 2011-06-08 2023-07-12 Life Technologies Corporation Design and development of novel detergents for use in pcr systems
CN106458885B (en) 2013-10-25 2019-12-10 生命技术公司 Novel compounds for use in polymerase chain reaction systems and uses thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2175597A (en) * 1982-12-23 1986-12-03 Procter & Gamble Ethoxylated mono-amines
EP0190708A1 (en) 1985-02-08 1986-08-13 Henkel Kommanditgesellschaft auf Aktien Process for the preparation of tertiary ether amines
US4650865A (en) * 1985-02-08 1987-03-17 Henkel Kommanditgesellschaft Auf Aktien Process for preparing tertiary ether amines
US4820436A (en) * 1985-06-22 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Detergents for low laundering temperatures
EP0252441A2 (en) * 1986-07-10 1988-01-13 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds and their application
EP0252441A3 (en) * 1986-07-10 1988-11-30 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds and their application
US4874554A (en) * 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
EP0253275A1 (en) * 1986-07-14 1988-01-20 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds and their use
US5292954A (en) * 1990-05-17 1994-03-08 Ethyl Corporation Amine oxide composition and process
WO2001017946A1 (en) * 1999-09-03 2001-03-15 The Procter & Gamble Company Tertiary alkyl alkoxylate derivatives and the composition thereof

Also Published As

Publication number Publication date
GB1087414A (en) 1967-10-18
GB1087415A (en) 1967-10-18
CA721771A (en) 1965-11-16

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