CH207344A - Process for the production of a basic condensation product. - Google Patents
Process for the production of a basic condensation product.Info
- Publication number
- CH207344A CH207344A CH207344DA CH207344A CH 207344 A CH207344 A CH 207344A CH 207344D A CH207344D A CH 207344DA CH 207344 A CH207344 A CH 207344A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- condensation product
- basic condensation
- sodium hydroxide
- hydroxide solution
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/10—Polythioethers from sulfur or sulfur-containing compounds and aldehydes or ketones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung eines basischen Kondensationsproduktes. Es wurde gefunden, dass die nach üblichen Verfahren geschwefelten Phenole, erhalten durch Umsetzung von Phenolen mit Schwe fel oder schwefelabgebenden Verbindungen in wässriger alkalischer oder organischer Lö sung, zur Herstellung von basischen Kon densationsprodukten, deren Salze in Wasser leicht löslich sind, verwendet werden kön nen. Dazu sind auch die Reaktionsprodukte geschwefelter Phenole mit Aldehyden brauch bar.
Zur Herstellung der neuen Kondensations produkte werden aromatische Oxyverbindun- gen zuerst mit Schwefel oder schwefelab gebenden Verbindungen zur Reaktion gebracht und die geschwefelten Verbindungen dann mit sekundären alipbatischen Aminen und Formaldehyd kondensiert, was entweder in wässrig-alkalischer Lösung oder aber in orga nischen Lösungsmitteln, die auch mit Was ser verdünnt sein können, erfolgen kann. Als aromatische Oxyverbindungen können auch Kondensationsprodukte von Phenolen mit Aldehydera verwende werden.
Wie dies für die Phenole bekannt ist, werden durch diese Reaktion sehr wahrscheinlich eine oder
EMI0001.0013
Gruppen mit Ri und R2 als Alkyl- und Clycloalkylgruppen in die durch Schwefelatome und gegebenenfalls Alde- hydrestbrücken verknüpften Phenole einge führt.
Als Phenole eignen sich alle für die Herstel lung von Schwefelverbindungen, insbesondere Schwefelharze der Phenole schon verwendeten aromatischen Oxyverbindungen. Technisch kommen vor allem in Frage:
Phenol, Kresole, deren Gemische, p-sek. oder -tert. Butylphenol, p-tert. Amylphenol, p-sek. Hexylphenol, Di- amylphenol, Mono-, Di- und Polychlorphenole, Bromphenole, Dioxydiarylmethane und die ent sprechenden -dimethylmethane,Cyclohexylphe- nol, Dioxydiarylsulfone,
Oxydiphenyle, Oxy- benzoesäuren, Novolak usw.
Als sekundäre aliphatische Amine, die in Frage kommen, seien genannt: Dimetbyl- und Diäthylamin, Methyläthylamin, Di-n- und -iso-propylamirr, Di-rr-butylarnirr, Diamylamin, Piperidin, Piperazin, Diäthanolamin usw.
Die neuen Verbindungen sind als Salze anorganischer und organischer Säuren in Was ser leicht löslich und sollen zur Erhöhung der Wasserfestigkeit direktgefärbter nativer und umgefällter Cellulose verwendet werden. Diese Möglichkeit der Verwendung ist sehr über raschend, dies im Hinblick auf die schwefel reifen, analogen bekannten Verbindungen aus Phenolen, Formaldehyd und sekundären ali- phatischen Aminen, welche überhaupt kehre Verbesserung der Wasserechtheit von Fär bungen bewirken.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines basischen Kondensationsproduktes, dadurch gekennzeich net, dass man Phenol mit Chlorschwefel er hitzt, das erhaltene Produkt mit Formaldehyd und Dimethylamin, zuletzt unter Zugabe von Natronlauge, umsetzt und das Reaktionspro dukt durch Neutralisieren der Natronlauge abscheidet. Die neue Verbindung, ein gelb liches Harz, ist in Säuren mit bräunlicher Farbe löslich und eignet sich zum Wasser- echtmachen von mit Direktfarbstoffen erhal tenen Färbungen auf nativer oder umgefällter Cellulose.
<I>Beispiel:</I> Zu 100 Teilen Phenol gibt man zwischen <B>60'</B> und<B>70' 0</B> 70 Teile Chlorschwefel und erhitzt 1 Stunde auf 100 C. Nachdem die Salzsäureentwicklung beendigt ist, fügt man 300 Teile Alkohol oder ein anderes, mit Wasser mischbares organisches Lösungsmittel wie zum Beispiel Aceton zu, dann trägt man 100 Teile Formaldehyd 30o/oig und langsam 240 Teile Dirnethylamin 19o/oig ein und er hitzt 3 Stunden zum Sieden.
Nach Zugabe von 80 Teilen Natronlauge 30o/oig erhitzt man eine weitere Stunde und destilliert dann den Alkohol ab. Stellt man die Reaktions masse neutral, so fällt ein Harz aus, das sich in Säuren löst und schon in ganz ge ringer Menge mit Direktfarbstoffen gefärbte Baumwolle wasserecht macht.
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Process for the production of a basic condensation product. It has been found that the phenols sulphurized by conventional processes, obtained by reacting phenols with sulfur or sulfur-releasing compounds in aqueous alkaline or organic solutions, can be used for the production of basic condensation products, the salts of which are readily soluble in water . The reaction products of sulphurized phenols with aldehydes are also useful.
To produce the new condensation products, aromatic oxy compounds are first reacted with sulfur or sulfur-releasing compounds and the sulphurized compounds are then condensed with secondary aliphatic amines and formaldehyde, either in an aqueous-alkaline solution or in organic solvents can be diluted with what water. Condensation products of phenols with aldehydes can also be used as aromatic oxy compounds.
As is known for the phenols, this reaction is very likely to produce an or
EMI0001.0013
Groups with R 1 and R 2 as alkyl and cycloalkyl groups in the phenols linked by sulfur atoms and optionally aldehyde bridges are introduced.
Suitable phenols are all aromatic oxy compounds already used for the production of sulfur compounds, in particular sulfur resins of the phenols. Technically, the following are particularly suitable:
Phenol, cresols, their mixtures, p-sec. or tert. Butylphenol, p-tert. Amylphenol, p-sec. Hexylphenol, di- amylphenol, mono-, di- and polychlorophenols, bromophenols, dioxydiarylmethanes and the corresponding dimethylmethanes, cyclohexylphenol, dioxydiarylsulfones,
Oxydiphenyls, oxybenzoic acids, novolak, etc.
Secondary aliphatic amines that may be used include: dimethylamine and diethylamine, methylethylamine, di-n- and iso-propylamine, di-r-butylamine, diamylamine, piperidine, piperazine, diethanolamine, etc.
The new compounds are easily soluble in water as salts of inorganic and organic acids and should be used to increase the water resistance of directly colored native and reprecipitated cellulose. This possibility of use is very surprising, with regard to the sulfur-ripe, analogous known compounds of phenols, formaldehyde and secondary aliphatic amines, which generally improve the waterfastness of dyeings.
The present patent relates to a process for the production of a basic condensation product, characterized in that phenol is heated with chlorosulfur, the product obtained is reacted with formaldehyde and dimethylamine, finally with the addition of sodium hydroxide solution, and the reaction product is separated off by neutralizing the sodium hydroxide solution. The new compound, a yellowish resin, is soluble in acids with a brownish color and is suitable for making dyes obtained with direct dyes on native or reprecipitated cellulose waterfast.
<I> Example: </I> Add between <B> 60 '</B> and <B> 70' 0 </B> 70 parts of chlorosulphur to 100 parts of phenol and heat for 1 hour at 100 C. After the development of hydrochloric acid is complete, add 300 parts of alcohol or another water-miscible organic solvent such as acetone, then add 100 parts of 30% formaldehyde and slowly 240 parts of 19% diethylamine and heat it to the boil for 3 hours.
After adding 80 parts of 30% sodium hydroxide solution, the mixture is heated for a further hour and then the alcohol is distilled off. If the reaction mass is rendered neutral, a resin precipitates which dissolves in acids and makes cotton dyed with direct dyes waterfast even in very small quantities.
,
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH207344T | 1938-07-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH207344A true CH207344A (en) | 1939-10-31 |
Family
ID=4445486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH207344D CH207344A (en) | 1938-07-18 | 1938-07-18 | Process for the production of a basic condensation product. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH207344A (en) |
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1938
- 1938-07-18 CH CH207344D patent/CH207344A/en unknown
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