DE867995C - Process for the production of amide-like conversion products of earth wax acids - Google Patents
Process for the production of amide-like conversion products of earth wax acidsInfo
- Publication number
- DE867995C DE867995C DEF2657D DEF0002657D DE867995C DE 867995 C DE867995 C DE 867995C DE F2657 D DEF2657 D DE F2657D DE F0002657 D DEF0002657 D DE F0002657D DE 867995 C DE867995 C DE 867995C
- Authority
- DE
- Germany
- Prior art keywords
- amide
- production
- earth wax
- acids
- conversion products
- 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
- 239000002253 acid Substances 0.000 title claims description 12
- 150000007513 acids Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 239000012084 conversion product Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 239000001993 wax Substances 0.000 description 15
- 239000007859 condensation product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- MAGMAMZGOLLUAU-UHFFFAOYSA-N octacosanoyl chloride Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(Cl)=O MAGMAMZGOLLUAU-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von amidartigen Umwandlungsprodukten der Erdwachssäuren Gegenstand der Erfindung ist ein Verfahren zur Herstellung von. amidarti:gen Umwandlungsprodukten der Erdwachssäuren, welche darin besteht, daß man die Erdwachssäuren oder ihre Säurechloride mit Aminocarbonsäuren kondensiert. Die Kondensation erfolgt in. an sich bekannter Weise, wie sie z. B. in H o u b e n, »Die Methoden der organischen Chemie«, z. $Bd., 3. Aufl. (19a5), S. 734 ff, 'beschrieben ist.Process for the preparation of amide-like conversion products of Earth wax acids The invention relates to a process for the production of. amidarti: gen Conversion products of the earth wax acids, which consists in the fact that one the earth wax acids or their acid chlorides condensed with aminocarboxylic acids. The condensation takes place in. Per se known manner, as z. B. in H o u b e n, »The methods of organic Chemistry «, e.g. $ Bd., 3rd ed. (19a5), pp. 734 ff, 'is described.
Dies erfindungsgiemäß hergestellten amidartigen Kondensationsprodukte der Erdwachssäuren mit den Aminocarbonsäuren besitzen wertvolle Eigenschaften, die ihren technischen Anwendungsbereich gegenüber .den Erdwachssäuren selbst oder ihren Salzen beträchtlich erweitern. So zeigen die Produkte beispielsweise die Eigenschaften, daß sie als freie Säuren. weitgehend wasserlöslich sind; hierdurch ist es erstmalig möglich, Wachse im sauren p11-Bereich technisch zu verwenden. Dies ist wichtig für verschiedene Imprägnierverfahren und auch für die kosmetische Industrie, da bekanntlich saure fett- bzw. wachsähnliche Substanzen in Form wäßriger Dispersionen oder Lösungen die Haut weit weniger angreifen und besser resorbiert werden a1$ neutrale oder alkalisch verseifte Produkte, wie auch beispielsweise die Haftfestigkeit solcher sauren Wachse auf tierischen Fasern weit höher ist als die der neutralen oder alkalischen Wachse.This amide-like condensation products produced according to the invention the earth wax acids with the aminocarboxylic acids have valuable properties that their technical field of application compared to the earth wax acids themselves or their Extend salts considerably. For example, the products show the properties that they are considered free acids. are largely water-soluble; this is the first time possible to use waxes in the acidic p11 range technically. This is important for various impregnation processes and also for the cosmetic industry, as is well known acidic fat or wax-like substances in the form of aqueous dispersions or solutions attack the skin far less and are better absorbed a1 $ neutral or alkaline saponified products, as well as, for example, the adhesive strength of such acidic waxes on animal fibers is far higher than that of the neutral or alkaline waxes Waxes.
Die Kondensationsprodukte von Erdwachssäuren mit Aminocar'bonsäuren können, da sie selbst Wachskörper darstellen, ohne weiteres mit anderen Fetten bzw. Paraffinen, Fettglyceriden oder Wachsen verschnitten werden, wobei ,die erhaltenen Mischungen ,sich durch eine hohe Emulgierfähigkeit auszeichnen. Die Produkte der vorliegenden Erfindung eignen sich deshalb vorteilhaft für die Herstellung von Textilwachsen, die selbst bei Mitverwendung von Paraffinen noch ohne weiteres in alkalischen Lösungen auswaschhar sind. Auch die Schuhkremindustrie und die Industrie der Schmier-und Staufferfette kann sich vorteilhaft der neuen Wachse als Emulsionsträger bedienen, da- sie den Komponenten der jeweiligen Mischung feinste Verteilung und den Verpastungsprodukten eine hohe Konsistenz vermitteln. Beispiel Man läßt i Mol in Benzol gelöste Montansäurechloride in eine wäßrige Lösung i Mols des Natriumsalzes der Butylaminoessigsäure bei einem px= ir -eintropfen. .Nach Beendigung der Umsetzung wird das. Reaktionsgemisch eingeengt.The condensation products of earth wax acids with aminocarboxylic acids can, since they are wax bodies themselves, easily with other fats or Paraffins, fatty glycerides or waxes are blended, the obtained Mixtures are characterized by a high emulsifiability. The products of the present invention are therefore advantageously suitable for the production of textile waxes, even if paraffins are also used, they are still readily available in alkaline solutions are washed out. Also the shoe polish industry and the lubricant and industry Staufferfette can advantageously use the new waxes as emulsion carriers, that the components of the respective mixture are finely distributed and the paste products convey a high consistency. EXAMPLE One mole of montanic acid chlorides dissolved in benzene is left in an aqueous solution of one mole of the sodium salt of butylaminoacetic acid at one px = ir -drops. After the reaction has ended, the reaction mixture is concentrated.
Das erhaltene amidartige Kondensationsprodukt kann beispielsweise mit der gleichen Gewichtsmenge Paraffin vom Schmelzpunkt 5q.° zu einem homogenen Wachskörper mit hohen glättenden Eigenschaften verschmolzen werden, &r u. a. als Kettenglätte für die Weberei zu verwenden ist und bei Gegenwart von Alkali trotz der hohen Menge an unverseifbarem Paraffin ohne weiteres aus dem Textilgut auszuwaschen ist.The amide-like condensation product obtained can, for example with the same amount by weight of paraffin with a melting point of 5q. ° to a homogeneous one Wax bodies with high smoothing properties are fused, & r u. is to be used as a chain smoothness for weaving and in spite of the presence of alkali the high amount of unsaponifiable paraffin can easily be washed out of the textile material is.
Löst man das erhaltene amidartige Kondensationsprodukt von Montansäurechloriden mit Butylaminoessigsäure in der gleichen Gewichtsmenge kochend heißem Wasser, so erhält man eine kremähnliche Masse, die die Haut zu glätten und zu fetten vermag; ohne ihr eine fettige Oberfläche zu geben.The amide-like condensation product obtained from montanic acid chlorides is dissolved with butylaminoacetic acid in the same amount by weight of boiling water, like that a cream-like mass is obtained, which is able to smooth the skin and make it greasy; without giving it a greasy surface.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2657D DE867995C (en) | 1942-03-14 | 1942-03-14 | Process for the production of amide-like conversion products of earth wax acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2657D DE867995C (en) | 1942-03-14 | 1942-03-14 | Process for the production of amide-like conversion products of earth wax acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE867995C true DE867995C (en) | 1953-02-23 |
Family
ID=7083381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF2657D Expired DE867995C (en) | 1942-03-14 | 1942-03-14 | Process for the production of amide-like conversion products of earth wax acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE867995C (en) |
-
1942
- 1942-03-14 DE DEF2657D patent/DE867995C/en not_active Expired
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