CH235189A - Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. - Google Patents
Process for the preparation of a water-soluble, higher molecular weight acyl biguanide.Info
- Publication number
- CH235189A CH235189A CH235189DA CH235189A CH 235189 A CH235189 A CH 235189A CH 235189D A CH235189D A CH 235189DA CH 235189 A CH235189 A CH 235189A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- soluble
- biguanide
- preparation
- molecular weight
- Prior art date
Links
- -1 acyl biguanide Chemical compound 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940123208 Biguanide Drugs 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VWSBHCBEGMABIO-UHFFFAOYSA-N N-carbamimidoyl-N-cyanododecanamide Chemical compound C(CCCCCCCCCCC)(=O)N(C(=N)N)C#N VWSBHCBEGMABIO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004048 vat dyeing Methods 0.000 description 1
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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/13—Fugitive dyeing or stripping dyes
- D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Darstellung eines wasserlöslichen, höhenmolekularen Acylbiguanids. Gegenstand vorliegenden Zusatzpatentes ist ein Verfahren zur Darstellung .eines wasserlöslichen, höhenmolekularen Acylbi- guanids, welches dadurch gekennzeichnet ist.
dass Lauroylcyanguanidhn me@thyliert, das 22ethyllauroyl-cyanguanidin mit Anilin zum lYIethyllauroyl - phenylbiguanid kondensiert und das gendensationsprodukt sulfiert wird.
Die Alkalisalze -des neuen Produktes sind helle Pulver, die in Wasser ,leicht löslich sind. Beispiel:
140 Teile Lauroylcyanguanidin, darge stellt aus Palmkernfettsäure und Dicyan- diamid, werden in 600 Volumteilen Chlor benzol angesichlemmt, bei 40-50 126 Teile Dimethylsulfat und 106 Teile wasserfreie Soda zugegeben und 16 Stunden bei 110 bis 120 methyliert.
30,5 Teile dieses methylierten Lauroyl- cyanguanidins erhitzt man mit 10 eTeilen Anilin während 18 Stunden auf 140' (in CO,- Atmosphäre). Es entsteht eine wachsartige bräunliche Masse.
30 Teile dieses gondensationsproduktcs werden in 60 Teilen Monohydrat gelöst und bei 0-10 30 Teile Oleum 26 % ig zugegeben. Sobald alles eingetropft ist, wird bei 20-30 bis zur Sodalöslichkeit weitergerührt. Dann wird auf Eiswasser gegessen, die ausigesche- d,ene Sulfosäure abfiltriert, mit Natronlauge neutralisiert,
und das Na-Salz zur Trockne eingedampft. Es wird ein hellgelbes Pulver erhalten, welches sich als Egalisier- und Ab- ziehmittel in der Küpenfärberei eignet.
Process for the preparation of a water-soluble, high molecular weight acyl biguanide. The subject of the present additional patent is a method for the preparation of a water-soluble, high molecular weight acylbiguanide, which is characterized.
that lauroylcyanguanidhn methylates, the 22ethyllauroylcyanguanidin condenses with aniline to lYIethyllauroyl - phenylbiguanid and the gene is sulfated.
The alkali salts of the new product are light-colored powders that are easily soluble in water. Example:
140 parts of lauroylcyanguanidine, which is made from palm kernel fatty acid and dicyanodiamide, are added to benzene in 600 parts by volume of chlorine, 126 parts of dimethyl sulfate and 106 parts of anhydrous soda are added at 40-50 and methylated at 110 to 120 for 16 hours.
30.5 parts of this methylated lauroylcyanguanidine are heated with 10 parts of aniline to 140 'for 18 hours (in a CO 2 atmosphere). A waxy, brownish mass is created.
30 parts of this condensation product are dissolved in 60 parts of monohydrate and, at 0-10, 30 parts of 26% oleum are added. As soon as everything has dripped in, stirring is continued at 20-30 until soda is soluble. Then it is eaten on ice water, the separated sulfonic acid is filtered off, neutralized with sodium hydroxide solution,
and the Na salt evaporated to dryness. A light yellow powder is obtained which is suitable as a leveling and stripping agent in vat dyeing.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH225155T | 1939-12-21 | ||
| CH232822T | 1940-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235189A true CH235189A (en) | 1944-11-15 |
Family
ID=34137166
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH232283D CH232283A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232282D CH232282A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232281D CH232281A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232285D CH232285A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH225155D CH225155A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232279D CH232279A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232280D CH232280A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232277D CH232277A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232278D CH232278A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232284D CH232284A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232822D CH232822A (en) | 1939-12-21 | 1940-04-11 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH235190D CH235190A (en) | 1939-12-21 | 1940-04-11 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH235189D CH235189A (en) | 1939-12-21 | 1940-04-11 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
Family Applications Before (12)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH232283D CH232283A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232282D CH232282A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232281D CH232281A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232285D CH232285A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH225155D CH225155A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232279D CH232279A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232280D CH232280A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232277D CH232277A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232278D CH232278A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232284D CH232284A (en) | 1939-12-21 | 1939-12-21 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH232822D CH232822A (en) | 1939-12-21 | 1940-04-11 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
| CH235190D CH235190A (en) | 1939-12-21 | 1940-04-11 | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. |
Country Status (3)
| Country | Link |
|---|---|
| AT (2) | AT163430B (en) |
| CH (13) | CH232283A (en) |
| GB (1) | GB546027A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2431644A (en) * | 1943-01-15 | 1947-11-25 | American Cyanamid Co | Preparation of guanides |
| US2446421A (en) * | 1944-11-03 | 1948-08-03 | Ici Ltd | Manufacture of arylbiguanide hydrochlorides |
| US2479498A (en) * | 1946-08-08 | 1949-08-16 | American Cyanamid Co | Preparation of 1,2-disubstituted-3-cyanoguanidines |
| US2622075A (en) * | 1946-12-03 | 1952-12-16 | Sandoz Ltd | Polyamine-cyanamide resins |
| DE1049587B (en) * | 1955-03-21 | 1959-01-29 | Rohm & Haas Company, Philadelphia, Pa. (V. St. A.) | Process for the production of polymers and copolymers |
-
1939
- 1939-12-21 CH CH232283D patent/CH232283A/en unknown
- 1939-12-21 CH CH232282D patent/CH232282A/en unknown
- 1939-12-21 CH CH232281D patent/CH232281A/en unknown
- 1939-12-21 CH CH232285D patent/CH232285A/en unknown
- 1939-12-21 CH CH225155D patent/CH225155A/en unknown
- 1939-12-21 CH CH232279D patent/CH232279A/en unknown
- 1939-12-21 CH CH232280D patent/CH232280A/en unknown
- 1939-12-21 CH CH232277D patent/CH232277A/en unknown
- 1939-12-21 CH CH232278D patent/CH232278A/en unknown
- 1939-12-21 CH CH232284D patent/CH232284A/en unknown
-
1940
- 1940-04-11 CH CH232822D patent/CH232822A/en unknown
- 1940-04-11 CH CH235190D patent/CH235190A/en unknown
- 1940-04-11 CH CH235189D patent/CH235189A/en unknown
- 1940-12-20 GB GB17941/40A patent/GB546027A/en not_active Expired
-
1947
- 1947-12-31 AT AT163430D patent/AT163430B/en active
- 1947-12-31 AT AT165059D patent/AT165059B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH232277A (en) | 1944-05-15 |
| AT165059B (en) | 1950-01-10 |
| CH232285A (en) | 1944-05-15 |
| CH232284A (en) | 1944-05-15 |
| CH232282A (en) | 1944-05-15 |
| CH232278A (en) | 1944-05-15 |
| AT163430B (en) | 1949-07-11 |
| CH232281A (en) | 1944-05-15 |
| CH232283A (en) | 1944-05-15 |
| CH232280A (en) | 1944-05-15 |
| CH225155A (en) | 1943-01-15 |
| CH235190A (en) | 1944-11-15 |
| GB546027A (en) | 1942-06-24 |
| CH232279A (en) | 1944-05-15 |
| CH232822A (en) | 1944-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH235189A (en) | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. | |
| AT160858B (en) | Process for the production of bodies containing sulfuric acid residues | |
| DE702833C (en) | ||
| AT220145B (en) | Process for the production of light colored long chain alkylbenzenesulfochlorides | |
| AT106981B (en) | Process for the production of acid-free, pure, resinous condensation products from phenols and aldehydes. | |
| DE887342C (en) | Process for the preparation of cycloaliphatic ketones | |
| DE839940C (en) | Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids | |
| CH240357A (en) | Process for the production of a water-soluble, higher molecular weight guanamine. | |
| CH212785A (en) | Process for the preparation of an aminoarylsulfonic acid derivative. | |
| CH240358A (en) | Process for the production of a water-soluble, higher molecular weight guanamine. | |
| CH180402A (en) | Process for the production of a textile auxiliary. | |
| CH240355A (en) | Process for the production of a water-soluble, higher molecular weight guanamine. | |
| CH233100A (en) | Process for the production of a tanning agent. | |
| CH167375A (en) | Process for the production of a new textile auxiliary. | |
| CH106407A (en) | Process for the production of a new intermediate product in the tar color industry. | |
| CH106116A (en) | Process for the production of a new intermediate product. | |
| CH175166A (en) | Process for the preparation of triethanolamine calcium bromide. | |
| CH214096A (en) | Process for the production of a new textile auxiliary. | |
| CH179087A (en) | Process for the preparation of a disulfation product of 2-aminoanthraquinone. | |
| CH198705A (en) | Process for the preparation of a water-soluble aromatic series compound. | |
| CH173736A (en) | Process for the production of a new textile auxiliary. | |
| CH338464A (en) | Process for the preparation of a 2-amino-imidazoline | |
| CH175677A (en) | Process for producing a diazoamido compound. | |
| CH106076A (en) | Process for the production of a new intermediate product. | |
| CH233345A (en) | Process for the preparation of a higher molecular weight, water-soluble condensation product. |