CH194945A - Process for the production of a new textile auxiliary. - Google Patents
Process for the production of a new textile auxiliary.Info
- Publication number
- CH194945A CH194945A CH194945DA CH194945A CH 194945 A CH194945 A CH 194945A CH 194945D A CH194945D A CH 194945DA CH 194945 A CH194945 A CH 194945A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- textile auxiliary
- production
- new textile
- alcohol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000004753 textile Substances 0.000 title claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- -1 carboxylic acid diester Chemical class 0.000 claims description 5
- 229960000541 cetyl alcohol Drugs 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 208000033809 Suppuration Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VJDQIBUPTBGINF-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)OC(=O)C2=C1 VJDQIBUPTBGINF-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005246 galvanizing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-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
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/58—Carboxylic acid groups or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Teztilhilfsstoffes. Es wurde .gefunden, dass man einen neuen Tegtilhilfsstoff erhält, wenn man Phthal- säure-4-sulfonsäure oder ein solches Derivat ,derselben, das durch Behandeln mit einem Alkohol in. einen Carbonsäureester der Phthals,äure-4-sulfonsäure übergehen kann,
mit Cetylalkohol zu einem Carbonsäure- monoester umsetzt und diesen darauf durch Behandeln mit Methylalkohol in einen Car- bonsäurediester umwandelt.
Die Umsetzung zum Carbonsäuremono- ester kann zum Beispiel durch Erhitzen der freien Sulfonsäure bezw. deren Salzen mit dem Cetylalkohol erfolgen, gegebenenfalls in Gegenwart von Lösungsmitteln, wie Pyri- din, Chinolin,
Dimethyl-p-toluidin und dergl. Besonders leicht reagiert das Ca.rbonsäure- anhydrid oder -chlorid. Carbonsäureester der Phthalsäure-4-sulfonsäure lassen sich eben falls als Ausgangsstoffe verwenden und kön nen mit Cetylalkohol umgeestert werden. Die Umwandlung des Carbonsäuremonoesters in den Carbonsäurediester kann durch Erhitzen mit Methylalkohol erfolgen.
Bei der Ver- eiterung können konzentrierte Schwefel säure, Chlorwasserstoffgas oder andere, die Vereiterung beschleunigende Mittel hinzu gefügt werden.
Die Vereiterung wird ex- leichtert, wenn man das bei der Reaktion sich bildende Wasser aus dem Veresterungs- gemiseh in bekannter Weise entfernt, bei- spielsweise mit Hilfe solcher Stoffe, die mit Wasser azeotrope Mischungen bilden.. Das abgespaltene Wasser kann auch durch Ar beiten unter vermindertem Druck oder durch Abdestillieren von überschüssig zugesetztem Alkoholentfernt werden.
Der neue Tegtilhilfsstoff stellt nach dem Neutralisieren und Trocknen eine zähe Masse dar, die von warmem Wasser zu einer kla ren, beim Schütteln schäumenden Lösung aufgenommen wird.
Der gemäss vorliegendem Verfahren her zustellende Tegtilhilfsstoff kann dank seiner kapillaraktiven Eigenschaften beispielsweise als Netz-, Reinigungs-, Wasch-, Dispergier- und E,galisiermittel Verwendung finden. Der neue Hilfsstoff kann allein oder zusammen mit andern geeigneten Stoffen, wie Lösungs mitteln, Salzen ein- und mehrwertiger Me talle, Seifen oder seifenartigen Stoffen oder Schutzkolloiden verwendet werden.
<I>Beispiel:</I> Man erwärmt 137 Gewichtsteile 4-Sulf o- phthalsäureanhydrid auf 6,5 und lässt unter Rühren l44 Gewichtsteile Cetylalko@hol von 6,0 im Laufe einer Stunde hinzufliessen, wobei die Temperatur auf 65 bis 72 gehal ten wird. Man rührt i/4 Stunde bei der ange gebenen Temperatur nach.
Der erhaltene 4-Sulfophthalsäuremonocetylester wird dar auf in der gleichen Menge Methylalkohol gelöst und der überschüssige Methylalkohol aus einem Wasserbad langsam abdestilliert. Um die Vereiterung .der zweiten Karboxyl- gruppe möglichst vollständig zu gestalten, wird der zusammen mit .dem abgespaltenen Wasser übergehende Methylalkohol mehr fach ergänzt.
Zuletzt wird der im Vereste- rungsgemisch verbliebene überschüssige Me thylalkohol unter vermindertem Druck ab destilliert.
Der Rückstand wird in warmem Wasser verteilt, mit Ammoniaklösung unter <B>30'</B> neutralisiert und zur Trockne ver dampft, , zweckmässig unter vermindertem Druck. Das erhaltene Produkt, eine zähe Na,s@e, die von warmem Wasser zu einer beim Schütteln schäumenden Lösung aufge- iiommen wird, kann beispielsweise als Emul- giermittel, insbesondere für Ölsäure, An wendung finden.
Process for the production of a new Teztilhilfsstoffes. It has been found that a new Tegil auxiliary is obtained if phthalic acid-4-sulfonic acid or such a derivative thereof, which can be converted into a carboxylic acid ester of phthalic acid-4-sulfonic acid by treatment with an alcohol,
reacted with cetyl alcohol to form a carboxylic acid monoester and then converted into a carboxylic acid diester by treatment with methyl alcohol.
The conversion to the carboxylic acid monoester can bezw, for example, by heating the free sulfonic acid. the salts of which are carried out with the cetyl alcohol, optionally in the presence of solvents such as pyridine, quinoline,
Dimethyl-p-toluidine and the like. The calcium anhydride or chloride reacts particularly easily. Carboxylic acid esters of phthalic acid-4-sulfonic acid can also be used as starting materials and can be transesterified with cetyl alcohol. The conversion of the carboxylic acid monoester into the carboxylic acid diester can be carried out by heating with methyl alcohol.
Concentrated sulfuric acid, hydrogen chloride gas or other agents which accelerate the suppuration can be added during the suppuration.
The suppuration is eased if the water formed during the reaction is removed from the esterification mixture in a known manner, for example with the aid of substances which form azeotropic mixtures with water. The water which is split off can also be worked by working removed under reduced pressure or by distilling off excess alcohol added.
After neutralization and drying, the new Tegtil auxiliary is a viscous mass that is absorbed by warm water to form a clear solution that foams when shaken.
Thanks to its capillary-active properties, the Tegtil adjuvant to be produced in accordance with the present process can be used, for example, as a wetting agent, cleaning agent, washing agent, dispersing agent and galvanizing agent. The new adjuvant can be used alone or together with other suitable substances, such as solvents, salts of mono- and polyvalent metals, soaps or soap-like substances or protective colloids.
<I> Example: </I> 137 parts by weight of 4-sulfophthalic anhydride are heated to 6.5 and, while stirring, 44 parts by weight of cetyl alcohol at 6.0 are allowed to flow in over the course of one hour, the temperature being 65 to 72 will. The mixture is stirred for 1/4 hour at the specified temperature.
The 4-sulfophthalic acid monocetyl ester obtained is then dissolved in the same amount of methyl alcohol and the excess methyl alcohol is slowly distilled off from a water bath. In order to make the suppuration of the second carboxyl group as complete as possible, the methyl alcohol which passes over together with the split off water is supplemented several times.
Finally, the excess methyl alcohol remaining in the esterification mixture is distilled off under reduced pressure.
The residue is distributed in warm water, neutralized with ammonia solution below 30 'and evaporated to dryness, advantageously under reduced pressure. The product obtained, a viscous Na, s @ e, which is absorbed by warm water to form a solution that foams when shaken, can be used, for example, as an emulsifier, in particular for oleic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194945T | 1936-05-23 | ||
| CH193075T | 1936-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194945A true CH194945A (en) | 1937-12-31 |
Family
ID=25722362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194945D CH194945A (en) | 1936-05-23 | 1936-05-23 | Process for the production of a new textile auxiliary. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194945A (en) |
-
1936
- 1936-05-23 CH CH194945D patent/CH194945A/en unknown
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