GB853440A - Detergent sulphonic acid and sulphate salts of certain amphoteric detergents - Google Patents

Detergent sulphonic acid and sulphate salts of certain amphoteric detergents

Info

Publication number
GB853440A
GB853440A GB3692156A GB3692156A GB853440A GB 853440 A GB853440 A GB 853440A GB 3692156 A GB3692156 A GB 3692156A GB 3692156 A GB3692156 A GB 3692156A GB 853440 A GB853440 A GB 853440A
Authority
GB
United Kingdom
Prior art keywords
carboxymethyl
dodecyl
acid
hydroxyethyl
aliphatic
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
GB3692156A
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.)
JOHN JOSEPH MCCABE JR
Original Assignee
JOHN JOSEPH MCCABE JR
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 JOHN JOSEPH MCCABE JR filed Critical JOHN JOSEPH MCCABE JR
Priority to GB3692156A priority Critical patent/GB853440A/en
Publication of GB853440A publication Critical patent/GB853440A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention comprises certain water-soluble detergent salts in which the anion is an alkali metal salt of an amino-acid containing five or more carbon atoms and a tertiary or quaternary nitrogen atom, and the cation is an organic sulphate ester or sulphonate having six or more carbon atoms ; the ions are as defined below, but the compounds of Specification 803,119 are excluded. The salts may have one of the five formulae: <FORM:0853440/IV(b)/1> where G is the cation (defined below), M is an alkali metal and the other groups are as follows :-R is a C4-C18 hydrocarbon radical ; Rb is an aliphatic or aralkyl hydrocarbon radical of 6-18 carbon atoms, the aliphatic part of the aralkyl group having at least 3 carbon atoms ; Rc is an aliphatic or aralkyl hydrocarbon radical of 4-18 carbon atoms ; Rd is a hydrocarbon group of 1-12 carbon atoms (optionally substituted, if aliphatic by hydroxy, keto or an ether linkage); Re is a C1-C4 aliphatic hydrocarbon radical (optionally substituted by hydroxyl if not C1); R1 is H or a C1-C4 aliphatic hydrocarbon radical (optionally substituted by hydroxy, keto or an ether linkage) ; R2 is as R1 (but nos H) ; R5 is as R2 (but not keto substituted); D it CH2-or-CONHRe- ; Q is R2OH, R2COOM or R2OR2COOM, or is R6 below ; Q1 is H or as for Q ; Y is H, RdCOOM or is R8 below ; Y1 is H or R5 COOM, or is R7 below ; T is RdCOOM or is R8 below ; R6 is as for R2 (but not hydroxy substituted) : R7 is as for R5 ; R8 is as for Rd ; y is 1-5 ; z is 0-5 ; and p is 0 or 1 (but p and z are never both zero). The anion G may be one of the following : R,CO,NRg-Rh,X, Rf,X, Rf,COORk,X, or Rf,Z,(C2H4O)x,SO3, where R is as before, Rf is a C6-C20 aliphatic or aralkyl hydrocarbon radical ; Rg is H or a C1-C8 aliphatic hydrocarbon radical (optionally substituted by hydroxyl or an ether linkage) ; Rh is as for Ra but may contain a CONH or NHCO linkage ; Rk is as for Rh but must be aliphatic, X is SO3 or OSO3, Z is O or S, and x is 1-5. The products which are quaternary salts are made by reacting the corresponding quaternary hydroxide or halide with an alkali metal salt of the appropriate sulphonic acid or sulphate ester at 100-140 DEG F. in the presence of a strong mineral acid to bring the pH down to 7-9. The mixture is then evaporated to dryness and the desired product extracted with an organic solvent, or the aqueous solution (containing inorganic salts) can be used directly as a wetting agent or detergent. The products which are salts of tertiary bases are made similarly by using the free base as starting material. Many examples are given, in which the various groups are as follows :-R1 Rb and Rc are undecyl, dodecyl, tridecyl or nonylphenyl ; Rd R2 and R5 are CH2, C2H4, CH2CHOH, C2H4OCH2, C2H4OCH2CHOH, (C2H4O)3 CH2, C6H4 and CH2C6H4 ; Re is C2H4 ; R6 is C2H5 ; R8 is CH3, (C2H4O)1-3 H, C6 H5 and CH2, C6H5 ; R5 is hexyl, nonyl, decyl, undecyl, dodecyl, octylphenyl, nonylphenyl and undecylphenyl ; Rg is methyl ; Rh and Rk are C2H4, C4H8, CH2CHOHCH2, C2H4NHCOCH2, C2H4OC2H4OC2H4 and C6H4. Many other suitable reactants are mentioned, of the types given below. Starting materials: (a) Amides and cyclic amidines. A diamine NH2R2NH2 is reacted with and acid RCOOH to produce an amide or a cyclic amidine (depending on the conditions) and this is further treated with Hal-Q, Hal-Q1 or Hal-R2 COOM. If Q is to contain a terminal hydroxy group it is possible to start with a hydroxydiamine NH2R2NHR2OH. Specific products obtained are N-lauroylamidoethyl-glycine, N-ethyl-N-lauroylamido-ethyl-glycine and the corresponding N-hydroxyethyl and N-carboxymethoxyethyl compounds ; N-lauroylamidoethyl-imino-bis-acetic acid, N-nonylbenzoylamidoethoxyethyl-imino-bis-acetic acid ; the 1 : 1-disubstituted-2-undecyl-imidazolinium hydroxides where one substituent is carboxymethyl and the other is carboxymethyl, ethyl, hydroxyethyl or carboxymethoxyethyl ; and a cyclic amidine with a larger ring by condensing nonylbenzoic acid with diamino-diethylether and reacting with chloracetic acid. Other suitable reactants are mentioned. (b) Amines containing an Rb group are made from RbNH2 by reaction wtith Hal-Y, Hal-T and Hal-Rd-COOM (or acrylonitrile and subsequent hydrolysis) ; and in the case of a hydroxy-substituted product ethylene oxide may be used instead of the chlorhydrin. Specified amines are dodecyl-methyl-amine, dodecyl-di-methyl-amine, dodecyl-di-triglycol-amine (after-reacted at the OH groups with 1 or 2 mols of chloracetic acid), hexyl-benzyl-(b - carboxy -b hydroxyethyl)-amine, dodecyl-phenyl-(carboxymethoxyethyl)-amine N-(nonylphenyl)-ethanolamine, and dodecyl-(hydroxyethoxyethyl)- (carboxyethyl)-amine. The last four can be quaternated with chloracetic acid, and other similar betaines are dodecyl-dimethyl, dodecyl-carboxyethyl-carboxyphenyl and dodecyl-carboxyethyl-carboxybenzyl. Betaines derived from imino-bis acetic acid are nonyl-carboxyethyl, nonyldihydroxypropyl and nonylphenyl-hydroxyethyl. The preparation of N-dodecylglycine and N-dodecyl-imino-bis-acetic acid is also described. Other suitable reactants are mentioned, and are disclosed in U.S.A. Specification 2,528,378. (c) Compounds containing an Rc group. Various polyamines are obtained by reacting ammonia with ethylene oxide, propylene oxide or epichlorhydrin, and are further alkylated with RcCH2Cl or acylated with RcCOOH. Alternatively butylene diamine can be reacted with butylene dichloride in the presence of caustic soda to give N:N1-di-(aminobutyl)-butylene diamine. Finally the acid group is introduced with Hal-R5-COOH. There are made this way (1) N-dodecyl-ethylene-diamines further substituted as follows: N1-carboxymethyl; N-(b -carboxy-b -hydroxyethyl)-N1-carboxymethyl; N1-(b -carboxy-b -hydroxyethyl)-N1-carboxymethyl; N : N1-di-(hydroxyethyl)-N1-carboxymethyl; and N:N1:N1-tri-(carboxymethyl); (2) N1-lauroyl-diethylene triamines further substituted as follows: N3-carboxymethyl, N2:N3-di-(carboxymethyl); N2:N3:N3-tri-(carboxymethyl), N2-hydroxyethyl-N3-carboxymethyl; N2: N3-di (hydroxyethyl)-N3-(carboxymethyl); N2: N3-di-(carboxymethoxyethyl)-N3-carboxymethyl; and N2: N3-di [(b -carboxy-b -hydroxy)-ethoxyethyl]-N3 - carboxymethyl; (3) 1-monylbenzylamino-3-carboxyethylamino-2-propanol; (4) 1-[(nonylbenzyl)-(carboxyethyl)-amino]-3-[di-(carboxyethyl) -amino]-2- propanol. In addition, epichlorhydrin is reacted with 2 mols of 1:3-diamino-propanol and the product acylated at one end with amylbenzoic acid and reacted at the other end with chloracetic acid. Other suitable reactants are mentioned. Some of these starting materials are covered by Specification 853,441.
GB3692156A 1956-12-03 1956-12-03 Detergent sulphonic acid and sulphate salts of certain amphoteric detergents Expired GB853440A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3692156A GB853440A (en) 1956-12-03 1956-12-03 Detergent sulphonic acid and sulphate salts of certain amphoteric detergents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3692156A GB853440A (en) 1956-12-03 1956-12-03 Detergent sulphonic acid and sulphate salts of certain amphoteric detergents

Publications (1)

Publication Number Publication Date
GB853440A true GB853440A (en) 1960-11-09

Family

ID=10392256

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3692156A Expired GB853440A (en) 1956-12-03 1956-12-03 Detergent sulphonic acid and sulphate salts of certain amphoteric detergents

Country Status (1)

Country Link
GB (1) GB853440A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304932A (en) * 1977-08-18 1981-12-08 Albright & Wilson Limited Process for producing novel carboalkylated surface active agents and product

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4304932A (en) * 1977-08-18 1981-12-08 Albright & Wilson Limited Process for producing novel carboalkylated surface active agents and product

Similar Documents

Publication Publication Date Title
GB818362A (en) Detergent preparations for the hair
GB930296A (en) The preparation of acylamino compounds
BR112020002466B1 (en) Process for producing a cyclic alkylene urea product
GB853440A (en) Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781389A (en) Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
GB768309A (en) Process for the production of amides of alginic acid
JPS6338343B2 (en)
Fuchigami et al. N-Halogen Compounds of Cyanamide Derivatives. I. Rearrangement of N-Alkylhaloamidines
US3258474A (en) Amphoteric alpha-sulfo fatty amides and a method of producing them
US2781375A (en) Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
GB938053A (en) Process for the preparation of aminoalkyl hydrogen sulphates and their conversion toalkylene amines
GB692413A (en) Improvements in or relating to methods of cleaning ferrous metal surfaces and to baths for use therein
GB834227A (en) Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof
US3352918A (en) Diamine oxyalkyl compounds
US2451432A (en) High molecular guanamines and a
GB897163A (en) New aminoalcohols and process for their manufacture
GB584914A (en) Process for the manufacture of new sulphamic acid derivatives
JPS5553251A (en) Polymerizable amino acid compound
GB717903A (en) Improvements in the manufacture of synthetic detergents
GB735098A (en) Improvements relating to guanidinium salts of mercapto-sulphonic acids and the preparation thereof
GB728660A (en) Process for the preparation of amines of the naphthostyril series
GB454320A (en) Manufacture of oxyalkylated nitrogen bases
GB919727A (en) Nitrogen derivatives of alkylene oxide condensates and their application to textiles
GB835802A (en) Process for the production of new anilides and salts thereof
GB834411A (en) Quaternary ammonium compounds