GB532439A - Manufacture of acylated ammonium-diarylmethane compounds - Google Patents
Manufacture of acylated ammonium-diarylmethane compoundsInfo
- Publication number
- GB532439A GB532439A GB24990/39A GB2499039A GB532439A GB 532439 A GB532439 A GB 532439A GB 24990/39 A GB24990/39 A GB 24990/39A GB 2499039 A GB2499039 A GB 2499039A GB 532439 A GB532439 A GB 532439A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- methyl
- aminodiphenylmethane
- dimethylamino
- acylated
- 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
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 abstract 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- GEKHSCVXJBSBJC-UHFFFAOYSA-N 2-[benzhydryl(methyl)amino]ethanol Chemical compound C=1C=CC=CC=1C(N(CCO)C)C1=CC=CC=C1 GEKHSCVXJBSBJC-UHFFFAOYSA-N 0.000 abstract 1
- -1 4 - ethylbenzylamino Chemical group 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- UBNCABDIHVVYRP-UHFFFAOYSA-N dimethylamino(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(O)(N(C)C)C1=CC=CC=C1 UBNCABDIHVVYRP-UHFFFAOYSA-N 0.000 abstract 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 abstract 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B1/00—Film strip handling
- G03B1/02—Moving film strip by pull on end thereof
- G03B1/04—Pull exerted by take-up spool
- G03B1/12—Pull exerted by take-up spool rotated by motor, e.g. spring
-
- G—PHYSICS
- G04—HOROLOGY
- G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS
- G04B1/00—Driving mechanisms
- G04B1/10—Driving mechanisms with mainspring
- G04B1/18—Constructions for connecting the ends of the mainsprings with the barrel or the arbor
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Polyurethanes Or Polyureas (AREA)
- Cosmetics (AREA)
Abstract
532,439. Textile assistants. GEIGY AKT.- GES., J. R. Aug. 31, 1939, No. 24990. Convention date, Sept. 1, 1938. Samples furnished. [Classes 2 (iii) and 15 (ii)] Acylated aminoniumdiarylmetbanes are prepared by re-acting a diarylmethane containing at least one primary, secondary or tertiary amino group and at least one other amino nitrogen or oxygen atom having reactive hydrogen united thereto with a higher aliphatic, cycloaliphatic or hydroaromatic carboxylic acid in such quantity that at least one amino group remains unacylated, and converting at least one amino group of the product into a quaternary ammonium group by treating with an alkylating or aralkylating agent. The higher carboxylic acids should contain at least 12 carbon atoms and may be replaced by derivatives thereof capable of acylation. The products are capillary active and are auxilary agents for the textile industry. In examples (1) 4-amino-41-dimethylaminodiphenylmethane is acylated with stearic acid chloride and then treated with dimethylsulphate : (2) 2:4-diamino-3<SP>1</SP>-methyl-4<SP>1</SP>-dimethylamino-diphenylmethane is acylated with the chlorides of coconut fatty acids and treated with diethylsulphate: (3) 4-dimethylamino-4<SP>1</SP>-(N- methyl - N - hydroxyethyl) - aminodiphenylmethane is acylated with oleic acid chloride and the resulting ester treated with dimethylsulphate ; a bis quaternary salt may be obtained by using increased quantity of alkylating agent: (4) 3 - chlor - 4 - dimethylamino-3<SP>1</SP>-(1V- methyl - N - hydroxyethyl) - amino - 4<SP>1</SP> - amino - diphenylmethane is acylated with lauric acid chloride and treated with diethylsulphate. Products containing one or more ammonium and/or acyl groups are specified derived from the following amino diarylmethanes : N- methyl-N-hydroxyethylaminodiphenylmethane, 4 - (N - methyl - N -hydroxy - ethyl) dimethylamino hydroxydiphenylmethane, aminodiphenylmethane, 4 - (N - aminoethyl) amino- 41 - dimethylaminodiphenylmethane, 4 - hydroxy - 4<SP>1</SP> - dimethylaminodiphenylmethane, 2:4 - dimethylamino - 4<SP>1</SP> - dimethylaminodiphenylmethane, 4:4<SP>1</SP> - diaminoditolylmethane, 4 - dimethylamino - 3<SP>1</SP> - ethyl - 2<SP>1</SP> - aminodiphenylmethane, 4 - dimethylamino - 3<SP>1</SP>- methoxy (or ethoxy) - 4<SP>1</SP> - aminodiphenylmethane, 4 - ethylbenzylamino - 4<SP>1</SP> - aminodiphenylmethane, 4 - diethylamino - 4<SP>1</SP> - aminodiphenylmethane, 4<SP>1</SP> - diethylamino - 2<SP>1</SP> - (or 3<SP>1</SP>-) carboxy - 4<SP>1</SP> - aminodiphenylmethane, 4 - dimethylamino - 3<SP>1</SP> - methyl - 1<SP>1</SP> - ethylaminodiphenylmethane, 4 - diethylamino - 4<SP>1</SP>- (N - methyl - N - dihydroxypropyl) - aminodiphenylmethane, 4 - dimethylamino - 4<SP>1</SP> - N- methyl - N - hydroxylethylaminodiphenylmethane and 4<SP>1</SP> - diethylamino - 2 - (N - methyl- N - hydroxyethyl) amino - 4 - aminodiphenylmethane. The use of diarylmethanes containing a tertiary nitrogen atom which belongs to a heterocyclic nucleus, e.g. a morpholine, piperazine or imidazol ring, and of resin, abietic and naphthenic acids for the acylation is mentioned. Starting materials containing alkylradicles having up to 18 carbon atoms attached to a tertiary nitrogen atom may also be used. Samples have been furnished under Sect. 2 (5) of products prepared by treating first withstearic acid chloride and then with dimethylsulphate (1) 2-hydroxy-5-amyl-4-dimethylaminodiphenylmethane, (2) 3-methyl-4-amino- 4<SP>1</SP> - morpholinyldiphenylmethane and (3) 3- amino - 4:4<SP>1</SP> - bis - dimethylaminodiphenyl methane (prepared from the corresponding nitro or nitroso compound by reduction).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208532T | 1938-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB532439A true GB532439A (en) | 1941-01-23 |
Family
ID=4446108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24990/39A Expired GB532439A (en) | 1938-09-01 | 1939-08-31 | Manufacture of acylated ammonium-diarylmethane compounds |
Country Status (3)
| Country | Link |
|---|---|
| CH (3) | CH208532A (en) |
| FR (1) | FR859698A (en) |
| GB (1) | GB532439A (en) |
-
1938
- 1938-09-01 CH CH208532D patent/CH208532A/en unknown
- 1938-09-01 CH CH210987D patent/CH210987A/en unknown
- 1938-09-01 CH CH210986D patent/CH210986A/en unknown
-
1939
- 1939-08-31 FR FR859698D patent/FR859698A/en not_active Expired
- 1939-08-31 GB GB24990/39A patent/GB532439A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR859698A (en) | 1940-12-24 |
| CH208532A (en) | 1940-02-15 |
| CH210987A (en) | 1940-08-15 |
| CH210986A (en) | 1940-08-15 |
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