US2830006A - Process of making fungicidal, bactericidal, and detergent compositions by reacting an aromatic amine and a dicyandiamide in the presence of a nonionic solvent - Google Patents

Process of making fungicidal, bactericidal, and detergent compositions by reacting an aromatic amine and a dicyandiamide in the presence of a nonionic solvent Download PDF

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US2830006A
US2830006A US416715A US41671554A US2830006A US 2830006 A US2830006 A US 2830006A US 416715 A US416715 A US 416715A US 41671554 A US41671554 A US 41671554A US 2830006 A US2830006 A US 2830006A
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Prior art keywords
bactericidal
fungicidal
parts
dicyandiamide
detergent compositions
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US416715A
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Birtwell Stanley
Rose Francis Leslie
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24Y being a hetero atom
    • C07C279/26X and Y being nitrogen atoms, i.e. biguanides
    • C07C279/265X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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 without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/6429Compounds containing nitrogen bound to a six-membered aromatic carbocyclic ring
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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 without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/645Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters

Definitions

  • a and B stand for aromatic nuclei, the same or different, optionally substituted by oneor more halogen, nitro, alkyl or alkoxy radicals
  • X stands for a hydrocarbon or a dialkoxybenzene radical of not more than '15 carbon atoms, preferably in the form of their salts, and for each 100 parts by weight of the said bisb'iguanide between 50 parts and 20,000 parts by weight of one ,,or more substances of known wetting and/or detergent properties.
  • compositions can conveniently and advantageously be made by conducting a process for the manufacture of a bisbiguanide in a non-ionic wetting agent I or detergent as solvent.
  • the so-manufactured compositions contain the bis-biguanides used in making the compositions of copending U. S. application S. N. 295,122.
  • hexamethylenediamine hydrochloride may be caused to react with p-chlorophenyldicyandiamide in the presence of, as reaction solvent, a condensation product of ethylene oxide and octylcresol.
  • the reaction. product possesses fungicidal, bactericidal and detergent properties and it contains 1:6-di(N :N -pchlorophenyldiguanido-N :N hexane dihydrochloride.
  • diamines of the formula NH XNH there may also be used, besides hexamethylenediamine, for example the following: trimethylenediamine, tetramethylenediamine,
  • p-tolyldicyandiamide .2:4-dimethylphenyldicyandiamide, p-anisyldicyandiamidq; ochlorophenyldicyandiamide, mchlorophenyldicyandiamide, 2 5-dichlorophenyldicyandiamide, 3:4-dichlorophenyld-icyandiamide, m-nitrophenyl-.
  • the formula ANH may for example be aniline, p-tolui dine, 2:4-dimethylaniline, p-anisidine, o-chloroaniline, m-
  • the amine in the react-ion is used in the form of a salt thereof.
  • Suitable salts include for example the hydrochloride, the hydrobromide and the sulphate.
  • Example 1 77.8 parts;of p-chlorophenyldicyandiamide, 37.8 parts of hexamethylenediamine dihydrochloride and 300 parts of the condensation product of octyl cresol with 9.5
  • Example 2 In a manner similar to that described in Example 1,
  • Example 5 2.59 parts of p-chlorophenyldicyandiamide, 126 parts of hexamethylenediamiue dihydrochloride, and 10 parts of the condensation product of stearic acid with 16.3 molecular proportions of ethylene oxide, are heated to- Partner Apr. 8,1958" 1:4-bis 7 aminopropyloxybenzene,
  • the reaction product is treated with 67 parts of water at 80 C., and the mixture is cooled and filtered.
  • the filtrate is a clear liquid which possesses valuable fungicidal, bactericidal and detergent properties.
  • Example 4 By working in a manner similar to that described in Example 3, of hexamethylenediamine dihydrochloride and 21.2 parts of a condensation product of octyl cresol with 9.5 molecular proportions of ethylene oxide are heated together at 140-l50, C. and there is obtained a liquid composition which possesses valuable fungicidal, bactericidal and detergent properties.

Description

Uni-ted States ump v H PROCESS OF MAKINGFUNGICIDAL, BACTERI- CIDAL, AND DETERGENT COMPOSITIONS BY REACTING AN AROMATIC AMINE AND A DICYANDIAMIDE IN THE PRESENCE OF A NONIONIC SOLVENT Stanley Birtwell and Francis Leslie Rose, Blackley, Manchester, England, assignors to Imperial Chemical Industries'Limited, a corporation of Great Britain No Drawing. Application March 16, 1954 Serial No. 416,715
Claims priority, application Great Britain March 26, 1953 i wherein A and B stand for aromatic nuclei, the same or different, optionally substituted by oneor more halogen, nitro, alkyl or alkoxy radicals, and X stands for a hydrocarbon or a dialkoxybenzene radical of not more than '15 carbon atoms, preferably in the form of their salts, and for each 100 parts by weight of the said bisb'iguanide between 50 parts and 20,000 parts by weight of one ,,or more substances of known wetting and/or detergent properties.
We have now found that useful fungicidal, bactericidal and detergent compositions can conveniently and advantageously be made by conducting a process for the manufacture of a bisbiguanide in a non-ionic wetting agent I or detergent as solvent. The so-manufactured compositions contain the bis-biguanides used in making the compositions of copending U. S. application S. N. 295,122.
Thus according to the invention we provide a process for the manufacture of fungicidal, bactericidal and detergent compositions which comprises interaction of a diamine of the formula:
in the form of a salt thereof, with a dicyandiamide of the X in the above formulae having the meaning stated above.
Thus for example hexamethylenediamine hydrochloride may be caused to react with p-chlorophenyldicyandiamide in the presence of, as reaction solvent, a condensation product of ethylene oxide and octylcresol. The reaction. product possesses fungicidal, bactericidal and detergent properties and it contains 1:6-di(N :N -pchlorophenyldiguanido-N :N hexane dihydrochloride.
As diamines of the formula NH XNH there may also be used, besides hexamethylenediamine, for example the following: trimethylenediamine, tetramethylenediamine,
pentamethylenediamine, heptamethylenediamine, decamethylenediamine, 4:4-diaminodiphenylmethane and p-phenylenediamine. As dicyandiamides of the formula ANHC(=NH)-NHCN there may also be used, besides p-chlorophenyldicyandiamide, for example the following, phenyldicyandiamide,
p-tolyldicyandiamide, .2:4-dimethylphenyldicyandiamide, p-anisyldicyandiamidq; ochlorophenyldicyandiamide, mchlorophenyldicyandiamide, 2 5-dichlorophenyldicyandiamide, 3:4-dichlorophenyld-icyandiamide, m-nitrophenyl-.
the formula ANH may for example be aniline, p-tolui dine, 2:4-dimethylaniline, p-anisidine, o-chloroaniline, m-
chloroaniline, p-chloroaniline, 2:5-dichloroaniline, 314-.
dichloroaniline, m-nitroani1ine, u-naphthylamine and ,9-
naphthylamine.
As said, in the react-ion the amine is used in the form of a salt thereof. Suitable salts include for example the hydrochloride, the hydrobromide and the sulphate.
- As non-ionic substances Example 1 77.8 parts;of p-chlorophenyldicyandiamide, 37.8 parts of hexamethylenediamine dihydrochloride and 300 parts of the condensation product of octyl cresol with 9.5
molecular proportions of ethylene oxide are mixed and the mixture is stirred at 140-150 C. for 18 hours. The reaction product is then boiled with 860 parts of water and there is obtained a homogeneous liquid composition which possesses valuable fungicidal, bactericidal and detergent properties.
. Example 2 In a manner similar to that described in Example 1,
2.59 parts of p-chlorophenyldicyandiamide are caused to react with 1.26 parts of hexamethylenediamine dihydrochloride in 10 parts of a condensation product of cetyl alcohol with 17 molecular proportions of ethylene oxide. The reaction mixture is then dissolved in 28.4 parts of water at C. and a detergent solution is obtained which possesses valuable fungicidal, bactericidal and detergent properties. I
Example 5 2.59 parts of p-chlorophenyldicyandiamide, 126 parts of hexamethylenediamiue dihydrochloride, and 10 parts of the condensation product of stearic acid with 16.3 molecular proportions of ethylene oxide, are heated to- Partner Apr. 8,1958" 1:4-bis 7 aminopropyloxybenzene,
those wherein X stands for possessing wetting and/or der. tergent properties there may be mentioned for example ethylene oxide with for ,eX-
gether with agitation for 18 hours at 140450? ICL The reaction product is treated with 67 parts of water at 80 C., and the mixture is cooled and filtered. The filtrate is a clear liquid which possesses valuable fungicidal, bactericidal and detergent properties.
Example 4 By working in a manner similar to that described in Example 3, of hexamethylenediamine dihydrochloride and 21.2 parts of a condensation product of octyl cresol with 9.5 molecular proportions of ethylene oxide are heated together at 140-l50, C. and there is obtained a liquid composition which possesses valuable fungicidal, bactericidal and detergent properties.
Example 6 3.3 parts of p-chloraniline hydrochloride, 3.5 parts of hexamethylene-bis-dicyandiamide and 17.5 parts of the condensation product of octylcresol with 9.5 molecular proportions of ethylene oxide are stirred together at 146- 150 C. for 18 hours. The mixture is then cooled to 80 C. and 50 parts of water are added. It is then filtered and the filtrate is a homogenous liquid composition which possesses valuable fungicidal, bactericidal and detergent properties.
What we claimis:
1. Process for the manufacture of fungicidal, bactericidal and detergent compositions which comprises interaction of a hexamethylenediamine salt with pchlorophenyldicyandiamide in the presence of a non-ionic detergent as a solvent for said reactants, said detergent being a condensation product of ethylene oxide and octylcresol.
6.4 parts of phenyldicyandiarnide, 3.78 parts.
i In a process for the manufacture of fungicidal, bac
tericidal and detergent compositions wherein the salt of an'amine selected from the group consisting of diamines of the formula NH XNH and monoamines of the formula ANH is reacted with a dicyandiamide selected .from the group consisting of dicyandiamides of the formula A-NH-C(:NH)-NH-CN and dicyandiamides of the formula CNNIICNHXNH%-NHCN NH I NH wherein X is selected from the group consisting of hydrocarbon and dialkoxybenzene radicals of not more than 15 carbon atoms; A is selected from the group consisting of aromatic hydrocarbon and halo, nitro, alkyl and alkoxy substituted aromatic hydrocarbons, said amine is a diamine when said-dicyandiarnide is A-NHC(=NH)NHCN and said amine is a monoamine when said dicyandiamide CNNHC-NH-XNH-(lfNH-CN i a NH the improvement wherein said reaction is carried out in the presence of a non-ionic substance as a solvent for said reactants, said substance being selected from the group consistingof non-ionic detergents and non-ionic weting agents formed from higher polyoxyethylene ether condensation products with long-chain alkyl phenols, fatty alcohols and fatty acids.
3. The process of claim 2 wherein said salt is the hydrochloride and said condensation product is the condensation product of octylcresol with 9.5 molecular proportions of ethylene oxide.
- References Cited in the file of this patent UNITED STATES PATENTS 216L431 Schoeller. July 4, 1939 2,643,232 Rose et a1. June 23, 1953 Rose et al July 27, 1954

Claims (1)

1. PROCESS FOR THE MANUFACTURE OF FUNGICIDAL, BACTERICIDAL AND DETERGENT COMPOSITIONS WHICH COMPRISES INTERACTION OF A HEXAMETHYLENEDIAMINE SALT WITH P-CHLOROPHENYLDICYANDIAMIDE IN THE PRESENCE OF A NON-IONIC DETERGENT AS A SOLVENT FOR SAID REACTANTS, SAID DETERGENT BEING A CONDENSATION PRODUCT OF ETHYLENE OXIDE AND OCTYLCRESOL.
US416715A 1953-03-26 1954-03-16 Process of making fungicidal, bactericidal, and detergent compositions by reacting an aromatic amine and a dicyandiamide in the presence of a nonionic solvent Expired - Lifetime US2830006A (en)

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GB8366/53A GB745064A (en) 1953-03-26 1953-03-26 Fungicidal and bactericidal compositions

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408384A (en) * 1963-08-08 1968-10-29 Shell Oil Co 4-methoxy-3, 5-dimethylphenyl methylcarbamate
US3909200A (en) * 1967-05-22 1975-09-30 Petrolite Corp Use of guanidine derived compounds as corrosion inhibitors
US4456543A (en) * 1982-06-17 1984-06-26 The Buckeye Cellulose Corporation Bisbiguanide based antibacterial cleansing products
US4842593A (en) * 1987-10-09 1989-06-27 The Procter & Gamble Company Disposable absorbent articles for incontinent individuals
US4886658A (en) * 1988-12-14 1989-12-12 The Procter & Gamble Company Oral treatment method for reducing plaque with reduced staining
US4919837A (en) * 1984-09-26 1990-04-24 Gluck Bruno A Antiseptic cleansing composition comprising a water-soluble salt of chlorhexidine
WO2007053053A1 (en) * 2005-11-07 2007-05-10 Sergei Alexeevich Balekhov Disinfecting agent producing method
DE102009060249A1 (en) 2009-12-23 2011-06-30 Lipovich, Vladimir, 30459 Preparing disinfectant, useful e.g. in medicine, comprises mixing polyhexamethylene guanidine base with its derivatives containing phosphate anions and iodine by condensing in melt flow of hexamethylenediamine and guanidine derivative
RU2487118C2 (en) * 2006-09-29 2013-07-10 Частное акционерное общество "Научно-технологический Центр "Укрводбэзпэка" Method of producing polyguanidines
RU2500667C1 (en) * 2012-10-25 2013-12-10 Общество с ограниченной ответственностью "Компания Вереск" Method of producing highly purified disinfectant

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1338003A (en) * 1971-06-18 1973-11-21 Ici Ltd Cleaning compositions
US4478821A (en) * 1982-01-26 1984-10-23 The Gillette Company Inhibition of body odor
FR2579979B1 (en) * 1985-04-05 1987-06-26 Pf Cosmetique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2164431A (en) * 1939-07-04 Production of etherg suitable as dis
US2643232A (en) * 1949-08-22 1953-06-23 Ici Ltd Polymeric diguanides
US2684924A (en) * 1951-02-05 1954-07-27 Ici Ltd Nu-chlorophenyldiguanidino compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2164431A (en) * 1939-07-04 Production of etherg suitable as dis
US2643232A (en) * 1949-08-22 1953-06-23 Ici Ltd Polymeric diguanides
US2684924A (en) * 1951-02-05 1954-07-27 Ici Ltd Nu-chlorophenyldiguanidino compounds

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408384A (en) * 1963-08-08 1968-10-29 Shell Oil Co 4-methoxy-3, 5-dimethylphenyl methylcarbamate
US3909200A (en) * 1967-05-22 1975-09-30 Petrolite Corp Use of guanidine derived compounds as corrosion inhibitors
US4456543A (en) * 1982-06-17 1984-06-26 The Buckeye Cellulose Corporation Bisbiguanide based antibacterial cleansing products
US4919837A (en) * 1984-09-26 1990-04-24 Gluck Bruno A Antiseptic cleansing composition comprising a water-soluble salt of chlorhexidine
EP0197968B1 (en) * 1984-09-26 1993-11-18 GLUCK, Bruno Anthony Antiseptic cleansing compositions
US4842593A (en) * 1987-10-09 1989-06-27 The Procter & Gamble Company Disposable absorbent articles for incontinent individuals
US4886658A (en) * 1988-12-14 1989-12-12 The Procter & Gamble Company Oral treatment method for reducing plaque with reduced staining
WO2007053053A1 (en) * 2005-11-07 2007-05-10 Sergei Alexeevich Balekhov Disinfecting agent producing method
US20090275663A1 (en) * 2005-11-07 2009-11-05 Sergei Alexeevich Balekhov Method for Producing a Disinfecting Agent
EA014841B1 (en) * 2005-11-07 2011-02-28 Сергей Алексеевич Балехов Disinfecting agent producing method
US8431616B2 (en) 2005-11-07 2013-04-30 Sergei Alexeevich Balekhov Method for producing a disinfecting agent
RU2487118C2 (en) * 2006-09-29 2013-07-10 Частное акционерное общество "Научно-технологический Центр "Укрводбэзпэка" Method of producing polyguanidines
DE102009060249A1 (en) 2009-12-23 2011-06-30 Lipovich, Vladimir, 30459 Preparing disinfectant, useful e.g. in medicine, comprises mixing polyhexamethylene guanidine base with its derivatives containing phosphate anions and iodine by condensing in melt flow of hexamethylenediamine and guanidine derivative
RU2500667C1 (en) * 2012-10-25 2013-12-10 Общество с ограниченной ответственностью "Компания Вереск" Method of producing highly purified disinfectant

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FR1159174A (en) 1958-06-24
GB745064A (en) 1956-02-22

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