CH339188A - Process for the production of cross-linked cellulose esters - Google Patents
Process for the production of cross-linked cellulose estersInfo
- Publication number
- CH339188A CH339188A CH339188DA CH339188A CH 339188 A CH339188 A CH 339188A CH 339188D A CH339188D A CH 339188DA CH 339188 A CH339188 A CH 339188A
- Authority
- CH
- Switzerland
- Prior art keywords
- cellulose
- esters
- products
- production
- fatty acid
- Prior art date
Links
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
- D21H17/25—Cellulose
- D21H17/27—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/10—Crosslinking of cellulose
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/05—Cellulose or derivatives thereof
- D06M15/07—Cellulose esters
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Verfahren zur Herstellung von vernetzten Zelluloseestern
Die Ester der Zellulose mit ungesättigten Fettsäuren bzw. die Mischester der Zellulose mit gesättigten und ungesättigten Fettsäuren, z. B. Zelluloseacetocrotonate besitzen eine mannigfaltige Reaktionsfähigkeit.
So ist es z. B. leicht möglich, verschiedene Verbindungen, wie Halogene, Amine oder dergleichen, an die Doppelbindung der an die Zellulose gebundenen ungesättigten Fettsäuren anzulagern.
Weiterhin neigen die ungesättigten Fettsäureester bzw. -mischester der Zellulose zur Bildung unlöslicher Produkte z. B. bei der Einwirkung von Hitze, Sauerstoff und Sauerstoff abspaltenden Verbindungen sowie bei Ultraviolett-Bestrahlung. Derartige Produkte sind jedoch meist ziemlich spröde und für den praktischen Gebrauch nicht verwendbar.
Es wurde nun die Beobachtung gemacht, dass sich derartige Ester bzw. Mischester der Zellulose, z. B.
Zelluloseacetocrotonate, sehr leicht mit Diaminen in vernetzte, stickstoffhaltige Kondensationsprodukte überführen lassen, die in den gebräuchlichen Lösungsmitteln unlöslich sind, einen erhöhten Erweichungspunkt haben und sich mit Wollfarbstoffen anfärben lassen. Diese Produkte sind nicht spröder als die Ausgangsprodukte, sondern besitzen im Gegenteil eine erhöhte Dehnung und Elastizität.
Gegenstand des vorliegenden Patentes ist nun ein Verfahren zur Herstellung von vernetzten Zelluloseestern, welches dadurch gekennzeichnet ist, dass man Zellulosefettsäureester, deren Fettsäureester mindestens zum Teil ungesättigt sind, mit Diaminen umsetzt.
Zur Herstellung der vernetzten Ester kann man z. B.
Lösungen von Zelluloseacetocrotonaten in Aceton oder Methylenchlorid mit wässrigen Lösungen von Diaminen bei normaler oder erhöhter Temperatur behandeln. Bei dieser Behandlungsweise werden die Acetocrotonate nicht oder nur sehr wenig verseift und besitzen neben den oben angeführten Eigenschaften eine kaum erhöhte Wasserempfindlichkeit und somit gute Nassfestigkeit. Sie enthalten je nach der Behandlungsdauer, der Temperatur und der Menge an gebundener, ungesättigter Fettsäure bis zu 2% Stickstoff. Die Verfahrenserzeugnisse dienen zur Herstellung von lösungsmittelfesten, leicht färbbaren Artikeln, wie z. B. Papier, Kunststoffartikeln, Textilfasern.
Beispiel
Einer 20-25% igen Lösung von Zelluloseacetocrotonat in Aceton oder Methylenchlorid werden 10% einer 10% igen Lösung von Hexamethylendiamin in demselben Lösungsmittel zugesetzt. Nach dem Verdunsten des Lösungsmittels und Wässern ist das Acetocrotonat in den gebräuchlichen Lösungsmitteln nicht mehr löslich und hat einen Stickstoffgehalt bis zu 2%.
PATENTANSPRUCH
Verfahren zur Herstellung von vernetzten Zelluloseestern, dadurch gekennzeichnet, dass man Zellulosefettsäureester, deren Fettsäurereste mindestens zum Teil ungesättigt sind, mit Diaminen umsetzt.
UNTERANSPRÜCHE
1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in Aceton ausführt.
2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in Methylenchlorid ausführt.
3. Verfahren nach Patentanspruch und Unteransprüchen 1 und 2, dadurch gekennzeichnet, dass man als Diamin Hexamethylendiamin verwendet.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the production of cross-linked cellulose esters
The esters of cellulose with unsaturated fatty acids or the mixed esters of cellulose with saturated and unsaturated fatty acids, e.g. B. Cellulose acetocrotonates have a diverse reactivity.
So it is e.g. B. easily possible to attach various compounds, such as halogens, amines or the like, to the double bond of the unsaturated fatty acids bound to the cellulose.
Furthermore, the unsaturated fatty acid esters or mixed esters of cellulose tend to form insoluble products such. B. in the action of heat, oxygen and oxygen-releasing compounds as well as in ultraviolet radiation. However, such products are usually quite brittle and not usable for practical use.
It has now been observed that such esters or mixed esters of cellulose, e.g. B.
Cellulose acetocrotonates can be converted very easily with diamines into crosslinked, nitrogen-containing condensation products, which are insoluble in the common solvents, have a high softening point and can be colored with wool dyes. These products are not more brittle than the starting products, but on the contrary have increased elongation and elasticity.
The subject matter of the present patent is a process for the production of crosslinked cellulose esters, which is characterized in that cellulose fatty acid esters, the fatty acid esters of which are at least partially unsaturated, are reacted with diamines.
To prepare the crosslinked esters, for. B.
Treat solutions of cellulose acetocrotonates in acetone or methylene chloride with aqueous solutions of diamines at normal or elevated temperature. With this method of treatment, the acetocrotonates are not saponified or only very little saponified and, in addition to the properties listed above, have hardly any increased water sensitivity and thus good wet strength. Depending on the duration of treatment, the temperature and the amount of bound, unsaturated fatty acids, they contain up to 2% nitrogen. The process products are used for the production of solvent-resistant, easily colored articles such. B. paper, plastic articles, textile fibers.
example
To a 20-25% solution of cellulose acetocrotonate in acetone or methylene chloride is added 10% of a 10% solution of hexamethylenediamine in the same solvent. After the solvent has evaporated and watered, the acetocrotonate is no longer soluble in the common solvents and has a nitrogen content of up to 2%.
PATENT CLAIM
Process for the production of crosslinked cellulose esters, characterized in that cellulose fatty acid esters, the fatty acid residues of which are at least partially unsaturated, are reacted with diamines.
SUBCLAIMS
1. The method according to claim, characterized in that the reaction is carried out in acetone.
2. The method according to claim, characterized in that the reaction is carried out in methylene chloride.
3. The method according to claim and dependent claims 1 and 2, characterized in that the diamine used is hexamethylenediamine.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH339188T | 1955-04-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH339188A true CH339188A (en) | 1959-06-30 |
Family
ID=4504923
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH339188D CH339188A (en) | 1955-04-07 | 1955-04-07 | Process for the production of cross-linked cellulose esters |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH339188A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0814093A2 (en) * | 1996-06-19 | 1997-12-29 | Canon Kabushiki Kaisha | Polymeric compound comprising glycopolymer and a method for decomposing the same |
-
1955
- 1955-04-07 CH CH339188D patent/CH339188A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0814093A2 (en) * | 1996-06-19 | 1997-12-29 | Canon Kabushiki Kaisha | Polymeric compound comprising glycopolymer and a method for decomposing the same |
EP0814093A3 (en) * | 1996-06-19 | 1999-03-17 | Canon Kabushiki Kaisha | Polymeric compound comprising glycopolymer and a method for decomposing the same |
US6316606B1 (en) | 1996-06-19 | 2001-11-13 | Canon Kabusiki Kaisha | Polymeric compound comprising glycopolymer and a method for decomposing the same |
US6900295B2 (en) | 1996-06-19 | 2005-05-31 | Canon Kabushiki Kaisha | Polymeric compound comprising glycopolymer and a method for decomposing the same |
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