DE573192C - Process for the preparation of detergents, wetting agents and dispersants - Google Patents
Process for the preparation of detergents, wetting agents and dispersantsInfo
- Publication number
- DE573192C DE573192C DEI43470D DEI0043470D DE573192C DE 573192 C DE573192 C DE 573192C DE I43470 D DEI43470 D DE I43470D DE I0043470 D DEI0043470 D DE I0043470D DE 573192 C DE573192 C DE 573192C
- Authority
- DE
- Germany
- Prior art keywords
- dispersants
- detergents
- preparation
- wetting agents
- acids
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 239000003599 detergent Substances 0.000 title claims description 5
- 239000002270 dispersing agent Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000080 wetting agent Substances 0.000 title claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 10
- -1 alkyl isocyanates Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N Taurine Natural products NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical group CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IPRSYPLQDZLFFB-UHFFFAOYSA-N 2-(butylamino)ethanesulfonic acid Chemical compound CCCCNCCS(O)(=O)=O IPRSYPLQDZLFFB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Description
Verfahren zur Darstellung von Wasch-, Netz- und Dispergiermitteln Durch das Hauptpatent 566 603 ist u. a. die Darstellung von Wasch-, Emulgier-, Netz- und Dispergiermitteln geschützt, die man erhält, indem man Alkylcarbamins,äurechIoride mit Aminogruppen tragenden aliphatischen, aromatischen oder hydroaromatischen echten Sulfons.äuren umsetzt.Process for the preparation of detergents, wetting agents and dispersants The main patent 566 603 protects, inter alia, the preparation of detergents, emulsifiers, wetting agents and dispersants which are obtained by adding alkyl carbamines, acid chlorides with aliphatic, aromatic or hydroaromatic ones bearing amino groups real sulfonic acids.
Es wurde nun gefunden, daß man zu diesen Verbindungen in guter Ausbeute auch gelangen kann, wenn man an Stelle der Alkylcarbaminsäurechloride die entsprechenden Isocyanate mit Aminogruppen tragenden aliphatischen oder aromatischen echten Sulfons,äuren umsetzt.It has now been found that these compounds can be obtained in good yield can also be achieved if, instead of the alkylcarbamic acid chlorides, the corresponding Isocyanates with aliphatic or aromatic true sulfonic acids carrying amino groups implements.
Ein Vorzug des Verfahrens besteht darin, daß bei der Kondensation keine störende Abspaltung von Salzsäure stattfindet, so daß. man zu fast salzfreien Produkten gelangen kann.., Die Isocyanate sind u. a. in sehr guter Ausbeute zugänglich, wenn män Fettsäurechloride mit Alkaliaziden in indifferenten Lösungsmitteln bei erhöhter Temperatur umsetzt, wobei unter Stickstoffentwicklung die Isocyanate entstehen.One advantage of the process is that during the condensation no disruptive elimination of hydrochloric acid takes place, so that. one to almost salt-free Products .., The isocyanates are inter alia. accessible in very good yield, if there are fatty acid chlorides with alkali azides in inert solvents Reacts at an elevated temperature, the isocyanates being formed with evolution of nitrogen.
Es ist zwar bekannt, Isocyanate mit Aminosulfonverbindungen umzusetzen. Nach dem vorliegenden Verfahren werden aber im Gegensatz zu dem bisher bekannten Verfahren hochmolekulare Isocyanate, d. h. ,also solche mit mehr als 8 Kohlenstoffatomen, benutzt-Bei der bekannten Reaktionsträgheit hochmolekularer Verbindungen war jedoch die glatte und schnell verlaufende Umsetzung dieser hochmolekularen Isocyanate mit aliphatischen oder aromatischen Aminosulfonsäuren, wie sie im vorliegenden Falle tatsächlich erfolgt, keineswegs zu erwarten. B eis p i@eLe i. Zu einer schwach sodaalkalischen Lösung von 18,5 Gewichtsteilen Butyltaurin in ioo GewichtsteilenWasser läßt man bei 70° C 2o Gewiclitsteile des aus Laurins,äurechlorid und Alkaliazid erhältlichen Isocyanats unter gutem Umrühren langsam zufließen. Dann rührt man noch i/2 Stunde bei 70°C nach. Eine Probe ist in Wasser klar löslich. Die erhaltene dünnflüssige Paste kann direkt als Waschmittel verwendet werden. Eine o, i %ige Lösung besitzt ein sehr starkes Schaumvermögen und eine sehr gute Waschwirkung auch in 30° hartem Wasser. An Stelle von Butyltaurin können andere Aminosulfons,äuren, wie z. B. Taurin, Methyltaurin, Phenyltaurin oder Anilinsulfonsäuren, an Stelle des Isocyanats aus Laurinsäure können z. B. die aus Ölsäure oder Stearinsäure erhältlichen Isocyanate verwendet werden.It is known to react isocyanates with aminosulfone compounds. According to the present process, however, in contrast to the previously known process, high molecular weight isocyanates, i.e. those with more than 8 carbon atoms, are used as it actually takes place in the present case, is by no means to be expected. B eis pi @ eLe i. To a weak sodaalkalischen solution of 1 8.5 parts by weight Butyltaurin in ioo part by weight of water is allowed to flow in slowly at 70 ° C 2o Gewiclitsteile the isocyanate available from lauric, äurechlorid alkali metal azide and stirring well. The mixture is then stirred for a further 1/2 hour at 70.degree. A sample is clearly soluble in water. The liquid paste obtained can be used directly as a detergent. A 0.1% solution has a very strong foaming power and a very good washing effect even in 30 ° hard water. Instead of butyl taurine, other aminosulfonic acids, such as. B. taurine, methyl taurine, phenyl taurine or anilinesulfonic acids, instead of the isocyanate from lauric acid can, for. B. the isocyanates obtainable from oleic acid or stearic acid can be used.
2. Zu einer soloalkalischen Lösung von 7,5 Gewichtsteilen Methyltaurin in 5o Gewichtsteilen Wasser läßt man bei 7o° C 15 Gewichtsteile des aus Olsäurechlorid und Alkaliazid erhältlichen Isocyanats zufließen. Dann rührt man noch 1%2 Stunde bei 7o° C nach. Eine herausgenommene Probe ist dann fast klar wasserlöslich. Die Eigenschaften der Verbindung sind ähnlich den im Beispiel r erwähnten.2. To a solo alkaline solution of 7.5 parts by weight of methyl taurine in 5o parts by weight of water is allowed to flow to at 7o ° C 1 5 parts by weight of the isocyanate available from Olsäurechlorid and alkali metal azide. The mixture is then stirred for a further 1% at 70 ° C. for 2 hours. A sample removed is then almost completely soluble in water. The properties of the compound are similar to those mentioned in example r.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI43470D DE573192C (en) | 1932-01-14 | 1932-01-14 | Process for the preparation of detergents, wetting agents and dispersants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI43470D DE573192C (en) | 1932-01-14 | 1932-01-14 | Process for the preparation of detergents, wetting agents and dispersants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE573192C true DE573192C (en) | 1933-03-29 |
Family
ID=7191044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI43470D Expired DE573192C (en) | 1932-01-14 | 1932-01-14 | Process for the preparation of detergents, wetting agents and dispersants |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE573192C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6785657B2 (en) * | 1999-11-29 | 2004-08-31 | Matsushita Electric Industrial Co., Ltd. | Digital signal processor |
-
1932
- 1932-01-14 DE DEI43470D patent/DE573192C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6785657B2 (en) * | 1999-11-29 | 2004-08-31 | Matsushita Electric Industrial Co., Ltd. | Digital signal processor |
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