DE369536C - Process for plasticizing cellulose derivatives - Google Patents
Process for plasticizing cellulose derivativesInfo
- Publication number
- DE369536C DE369536C DEF48536D DEF0048536D DE369536C DE 369536 C DE369536 C DE 369536C DE F48536 D DEF48536 D DE F48536D DE F0048536 D DEF0048536 D DE F0048536D DE 369536 C DE369536 C DE 369536C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- cellulose derivatives
- plasticizing
- plasticizing cellulose
- derivatives
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 229920002678 cellulose Polymers 0.000 title description 3
- 239000001913 cellulose Substances 0.000 title description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PEHXKUVLLWGBJS-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)ethyl]phenol Chemical class C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1O PEHXKUVLLWGBJS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- -1 Oxy fatty acids Chemical class 0.000 description 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DZVRIIUGDPGKMO-UHFFFAOYSA-N (1,2-dimethoxy-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(OC)(COC)C1=CC=CC=C1 DZVRIIUGDPGKMO-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
Verfahren zum Plastischmachen von Zellulosederivaten. In dem Hauptpatent 36756o ist ein Verfahren zum Plastischmachen von Zellulosederivaten beschrieben, darin bestehend, daß man Äthylidendiphenole an Stelle von Kampfer verwendet.Process for plasticizing cellulose derivatives. In the main patent 36756o describes a process for plasticizing cellulose derivatives, consisting in using ethylidene diphenols in place of camphor.
Es wurde nun gefunden, daß sich in gleichem bzw. erhöhtem Maße die Alkylderivate der Äthylidendiphenole (Dioxydiphenyläthan) für die genannten Zwecke eignen. Und zwar sind geeignet sowohl einfache Alkylderivate, wie z. B. das Dimethoxydiphenyläthan oder das entsprechende Benzylderivat, als auch solche Derivate, welche im Alkyl noch Oxy- bzw. Karboxylgruppen enthalten, z. B. das Glycolderivat des Dioxydiphenyläthan oder sein Glycolsäurederivat. Man erhält diese Körper in einfacher Weise, indem man die Äthylidendiphenole in alkalischer Lösung mit Alkylierungsmitteln, wie Diätylsulfat, Benzylchlorid, Chlorhydrin oder Halogenfettsäure umsetzt, wobei man Äthylidendiphenol zur Alkylkomponente im Verhältnis z : i oder auch i : 2 zur Anwendung bringen kann. Beispiele: Z. ioo Teile Azetylzellulose werden mit qo Teilen Dimethoxydiphenyläthan und 16o Teilen Benzolalkohol so lange verrührt, bis eine gleichmäßige Masse entstanden ist. Nach Verdunsten des Lösungsmittels hinterbleibt ein klarer, farbloser Film von hoher Elastizität. Dimethoxydiphenyläther wird dargestellt durch Umsetzung einer alkalischen Lösung von i Mol. Dioxydiphenyläthan mit z Mol. Dimethylsulfat. Es kristallisiert in weißen Nadeln und schmilzt bei 82 bis 83°. Es ist löslich in fast allen organischen Lösungsmitteln.It has now been found that the Alkyl derivatives of ethylidenediphenols (dioxydiphenylethane) for the purposes mentioned suitable. Both simple alkyl derivatives, such as. B. Dimethoxydiphenyläthan or the corresponding benzyl derivative, as well as those derivatives which are in the alkyl still contain oxy or carboxyl groups, e.g. B. the glycol derivative of dioxydiphenylethane or its glycolic acid derivative. One gets these bodies in a simple way by the ethylidenediphenols in alkaline solution with alkylating agents such as dietyl sulfate, Reacts benzyl chloride, chlorohydrin or halogenated fatty acid, with ethylidenediphenol to the alkyl component in the ratio z: i or also i: 2 can be used. Examples: 100 parts of acetyl cellulose are mixed with qo parts of dimethoxydiphenylethane and 16o parts of benzene alcohol are stirred until the mixture is uniform is. After the solvent has evaporated, a clear, colorless film remains of high elasticity. Dimethoxydiphenyläther is represented by implementing a alkaline solution of 1 mole. Dioxydiphenyläthan with z mole. Dimethyl sulfate. It crystallizes in white needles and melts at 82 to 83 °. It is soluble in almost all organic Solvents.
2. 6o Teile Nitrozellulose werden mit 25 Teilen des durch Umsetzung von Dioxydikresyläthan in alkalischer Lösung mit Äthylenchlorhydrin erhaltenen Glycolderivates, einem bei gewöhnlicher Temperatur durchsichtigen viskosen 051e, und .einer Mischung von 2o Teilen Benzol mit 5o Teilen Alkohol verrieben, bis die Masse gleichmäßig gelatinös geworden ist. Der nach Verdampfen des Lösungsmittels erhaltene Film ist klar und ausgezeichnet biegsam.2. 6o parts of nitrocellulose are reacted with 25 parts of the glycol derivatives obtained from dioxydicresylethane in alkaline solution with ethylene chlorohydrin, a viscous 051e, transparent at ordinary temperature, and a mixture of 20 parts of benzene and 50 parts of alcohol rubbed in until the mass is uniform has become gelatinous. The film obtained after evaporation of the solvent is clear and extremely flexible.
3. 6o Teile Azetylzelluldse und 2o Teile des durch Umsetzung von z Mol. Dioxydiphenyläthan mit i Mol. Chloressigsäure entstandenen bei etwa i2o° schmelzenden Oxyfettsäure werden mit der zur gleichmäßigen Aufquellung genügenden Menge Amylazetat gemischt. Nach Verdampfendes Lösungsmittels erhält man einen elastischen klaren Film.3. 6o parts of Acetylzelluldse and 2o parts of the reaction of z Mol. Dioxydiphenyläthan with 1 Mol. Chloracetic acid formed at about 12 ° melting Oxy fatty acids are made with amylacetate in the amount sufficient to swell evenly mixed. After evaporation of the solvent, an elastic one is obtained clear film.
4. 8o Teile Azetylzellulose werden mit qo Teilen Dibenzyldioxydiphenyläthan und der genügenden Menge Azeton vermischt und so lange evtl. unter Erwärmen digeriert, bis gleichmäßige Lösung entstanden ist. Nachdem das Lösungsmittel verdunstet ist, hinterbleibt ein klarer, für die Technik gut brauchbarer Film.4. 80 parts of acetyl cellulose are mixed with qo parts of dibenzyldioxydiphenylethane and the sufficient amount of acetone mixed and digested for as long, possibly with heating, until a uniform solution is obtained. After the solvent has evaporated, What remains is a clear film that is useful for the technology.
Man erhält die Dibenzylverbindung des Dioxydiphenyläthan, indem man dieses in alkalischer Lösung mit der berechneten Menge Benzylchlorid unter Rückfluß so lange kocht, bis der Geruch nach Benzvlchlorid verschwunden ist. Geringe Spuren werden mit Wasserdampf vollends ausgetrieben. Der alkaliunlösliche Rückstand wird aus Sprit oder Eisessig umkristallisiert. Er schmilzt bei etwa 85 bis 87°. Das Dibenzyldioxydiphenyläthan ist löslich in Alkohol, Azeton, Eisessig.The dibenzyl compound of dioxydiphenylethane is obtained by this in alkaline solution with the calculated amount of benzyl chloride under reflux simmer until the smell of benzyl chloride has disappeared. Minor traces are completely expelled with steam. The alkali-insoluble residue becomes recrystallized from spirit or glacial acetic acid. It melts at around 85 to 87 °. The dibenzyldioxydiphenylethane is soluble in alcohol, acetone, glacial acetic acid.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF48536D DE369536C (en) | 1921-02-08 | 1921-02-08 | Process for plasticizing cellulose derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF48536D DE369536C (en) | 1921-02-08 | 1921-02-08 | Process for plasticizing cellulose derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE369536C true DE369536C (en) | 1923-02-20 |
Family
ID=7102308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF48536D Expired DE369536C (en) | 1921-02-08 | 1921-02-08 | Process for plasticizing cellulose derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE369536C (en) |
-
1921
- 1921-02-08 DE DEF48536D patent/DE369536C/en not_active Expired
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