GB498090A - Process for the production of water-soluble, nitrogenous compounds - Google Patents
Process for the production of water-soluble, nitrogenous compoundsInfo
- Publication number
- GB498090A GB498090A GB30629/37A GB3062937A GB498090A GB 498090 A GB498090 A GB 498090A GB 30629/37 A GB30629/37 A GB 30629/37A GB 3062937 A GB3062937 A GB 3062937A GB 498090 A GB498090 A GB 498090A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- treated
- dimethylsulphate
- amidine
- dodecylbromide
- 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
Links
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title 1
- 150000001409 amidines Chemical class 0.000 abstract 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 6
- -1 imide chloride Chemical class 0.000 abstract 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000003141 primary amines Chemical class 0.000 abstract 3
- 150000003335 secondary amines Chemical class 0.000 abstract 3
- JDFOIACPOPEQLS-UHFFFAOYSA-N 1,2,2,3-tetramethylcyclopentane-1-carboxylic acid Chemical compound CC1CCC(C)(C(O)=O)C1(C)C JDFOIACPOPEQLS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 150000001408 amides Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 abstract 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 abstract 1
- JKOTZBXSNOGCIF-UHFFFAOYSA-N 1-bromopentadecane Chemical compound CCCCCCCCCCCCCCCBr JKOTZBXSNOGCIF-UHFFFAOYSA-N 0.000 abstract 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 abstract 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 abstract 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 abstract 1
- FSNJJTYNVHJCDD-UHFFFAOYSA-N 2-cyclohexyl-3,4-dimethylbenzenecarboximidamide Chemical compound CC1=C(C(=C(C(=N)N)C=C1)C1CCCCC1)C FSNJJTYNVHJCDD-UHFFFAOYSA-N 0.000 abstract 1
- LAGJUAWOXWWBME-UHFFFAOYSA-N 3,4-dimethyl-2-pentadecylbenzenecarboximidamide Chemical compound CC1=C(C(=C(C(=N)N)C=C1)CCCCCCCCCCCCCCC)C LAGJUAWOXWWBME-UHFFFAOYSA-N 0.000 abstract 1
- WCTRIPCAGUWVHQ-UHFFFAOYSA-N 3,4-dimethyl-2-phenylbenzenecarboximidamide Chemical compound CC1=C(C(=C(C(=N)N)C=C1)C1=CC=CC=C1)C WCTRIPCAGUWVHQ-UHFFFAOYSA-N 0.000 abstract 1
- ZKBWKIQWUUSCIJ-UHFFFAOYSA-N 3-ethyl-2-phenylbenzenecarboximidamide Chemical compound C(C)C=1C(=C(C(=N)N)C=CC1)C1=CC=CC=C1 ZKBWKIQWUUSCIJ-UHFFFAOYSA-N 0.000 abstract 1
- MVDJPCNXIHJNEK-UHFFFAOYSA-N 3-ethyl-2-piperidin-1-ylbenzenecarboximidamide Chemical compound C(C)C=1C(=C(C(=N)N)C=CC1)N1CCCCC1 MVDJPCNXIHJNEK-UHFFFAOYSA-N 0.000 abstract 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 abstract 1
- JFMNMSAPWXWEID-UHFFFAOYSA-N 3-phenyl-2-piperidin-1-ylbenzenecarboximidamide Chemical compound C1(=CC=CC=C1)C=1C(=C(C(=N)N)C=CC1)N1CCCCC1 JFMNMSAPWXWEID-UHFFFAOYSA-N 0.000 abstract 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- BUGJLCKBDQBYHE-UHFFFAOYSA-N C(CCCCCCCCCCC)Br.C(C1=CC=CC=C1)Cl Chemical compound C(CCCCCCCCCCC)Br.C(C1=CC=CC=C1)Cl BUGJLCKBDQBYHE-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 241000276484 Gadus ogac Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 235000021314 Palmitic acid Nutrition 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 abstract 1
- 150000005524 benzylchlorides Chemical class 0.000 abstract 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 abstract 1
- 239000003026 cod liver oil Substances 0.000 abstract 1
- 235000012716 cod liver oil Nutrition 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 1
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000009967 direct dyeing Methods 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 abstract 1
- VENJCACPSJGPCM-UHFFFAOYSA-N n-phenylhexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 VENJCACPSJGPCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amidines having the formula RC(NR2R3): NR1 wherein R is an alkyl, aralkyl, aryl or hydroaryl radicle, R1 the same radicles as R and also a heterocyclic radicle, the alkyl and aralkyl radicles possibly containing a hetero atom, e.g. S,O or NH and R2 and R3 are hydrogen or an alkyl, aralkyl, aryl or hydroaryl radicle, R1 and R3 possibly belonging to the same hydroaromatic ring, are treated with alkylating or aralkylating agents to convert them into water soluble form. In examples: (1) dimethylphenylbenzamidine is treated with dimethylsulphate, benzylchloride dodecylbromide, pentadecylbromide and octodecyl bromide; (2) ethylphenylbenzamidine is treated with dimethylsulphate; (3) benzoylchloride is condensed with pentadecylamine and dimethyl pentadecylbenzamidine is formed by treating with dimethylamine the imide chloride obtained by reacting the condensation product with thionylchloride; the amidine is alkylated with dimethyl or diethylsulphate; benzoylchloride may be replaced by campholic or fencholic acid chlorides; (4) phenylpiperidylbenzamidine or a derivative thereof halogenated in the acid or amide residue is treated with dimethylsulphate; (5) cetyl or dodecylbromide is used to alkylate dimethyl cyclohexylbenzamidine; (6) dimethylsulphate is used to alkylate a : a -dichlorpalmitic acid dimethylphenyl amidine which is prepared by reacting dimethyl amine with the chloride obtained by treating palmitic acid anilide with phosphoruspentachloride; (7) palmitic acid o-toluyldimethylamidine is alkylated with dimethylsulphate; (8) benzanilide is converted into the imide-chloride and the latter reacted with diethylethylenediamine; the resulting amidine or the corresponding amidine derived from the imide chloride from campholic acid butylamide is treated with dodecyl or octadecylbromide; (9) dodecylbromide is reacted with the amidine from dimethylamine and ethylbenzimide chloride; (10) ethylpiperidylbenzamidine is treated with dodecylbromide. The amidines besides being made from the imide halides and ammonia or any primary or secondary amine, may be made by decomposing the corresponding cyanides or thioamides with ammonia or primary or secondary amines. Carboxylic acid amides of secondary amines may also be transformed into the ketochlorides and then reacted with primary amines. Specified components for producing the amidines include: a -chlorisobutyric acid, hexahydrobenzoic acid, dichloracetic acid, amines derived by Hofmann's reaction from amides of fatty acids, e.g. cod liver oil acid, amines derived from ammonia by reaction with alcohols such as those obtained by hydrogenation of fats, resins and naphthenic acids or benzylphenols, unsym: diethyl-p-phenylenediamine, 4-chlor or 3 : 4-dichloraniline, cyclohexylaniline and 2-aminobenzthiazole. For the alkylation and aralkylation are specified: methylchloride, laurylchloride, nuclear halogenated benzyl chlorides, glycerinechlorhydrin and chloracetic ester. The phosphates, silicofluorides, formates and oxalates of the amidines are mentioned. The products are stated to be textile assistants and may be used for wetting, improving the fastness of direct dyeings, stripping naphthol AS dyeings, imparting a mat appearance to regenerated cellulose, softening textiles and combating animal pests, e.g. mothproofing. They also have bactericidal and fungicidal properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH498090X | 1937-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB498090A true GB498090A (en) | 1939-01-03 |
Family
ID=4516808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30629/37A Expired GB498090A (en) | 1937-07-08 | 1937-11-08 | Process for the production of water-soluble, nitrogenous compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB498090A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084192A (en) * | 1958-12-19 | 1963-04-02 | Du Pont | Alpha-halo-formamidines |
| US3218147A (en) * | 1959-07-10 | 1965-11-16 | Ici Ltd | Pesticides |
| US3284289A (en) * | 1962-03-08 | 1966-11-08 | Duerr Dieter | Method for protecting plants from fungi |
-
1937
- 1937-11-08 GB GB30629/37A patent/GB498090A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084192A (en) * | 1958-12-19 | 1963-04-02 | Du Pont | Alpha-halo-formamidines |
| US3218147A (en) * | 1959-07-10 | 1965-11-16 | Ici Ltd | Pesticides |
| US3284289A (en) * | 1962-03-08 | 1966-11-08 | Duerr Dieter | Method for protecting plants from fungi |
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