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 PDFInfo
- Publication number
- 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
- Authority
- US
- United States
- Prior art keywords
- bactericidal
- fungicidal
- parts
- dicyandiamide
- detergent compositions
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives 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
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
- C07C279/265—X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General 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
- D06P1/44—General 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
- D06P1/64—General 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
- D06P1/642—Compounds containing nitrogen
- D06P1/6429—Compounds containing nitrogen bound to a six-membered aromatic carbocyclic ring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General 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
- D06P1/44—General 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
- D06P1/64—General 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
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
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.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8366/53A GB745064A (en) | 1953-03-26 | 1953-03-26 | Fungicidal and bactericidal compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US2830006A true US2830006A (en) | 1958-04-08 |
Family
ID=9851162
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US416715A Expired - Lifetime US2830006A (en) | 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 |
Country Status (3)
Country | Link |
---|---|
US (1) | US2830006A (en) |
FR (1) | FR1159174A (en) |
GB (1) | GB745064A (en) |
Cited By (10)
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)
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)
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 |
-
1953
- 1953-03-26 GB GB8366/53A patent/GB745064A/en not_active Expired
-
1954
- 1954-03-15 FR FR1159174D patent/FR1159174A/en not_active Expired
- 1954-03-16 US US416715A patent/US2830006A/en not_active Expired - Lifetime
Patent Citations (3)
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)
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 |
Also Published As
Publication number | Publication date |
---|---|
FR1159174A (en) | 1958-06-24 |
GB745064A (en) | 1956-02-22 |
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