DE582848C - Process for the production of resinous condensation products - Google Patents
Process for the production of resinous condensation productsInfo
- Publication number
- DE582848C DE582848C DEI41903D DEI0041903D DE582848C DE 582848 C DE582848 C DE 582848C DE I41903 D DEI41903 D DE I41903D DE I0041903 D DEI0041903 D DE I0041903D DE 582848 C DE582848 C DE 582848C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- production
- condensation products
- resinous condensation
- resin
- 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
- 239000007859 condensation product Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000011347 resin Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 4
- 241000218657 Picea Species 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000025 natural resin Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004859 Copal Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000782205 Guibourtia conjugata Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung von harzartigen Kondensationsprodukten Es wurde gefunden, daß man technisch wertvolle Kondensationsprodukte erhält, wenn man die nicht esterartigen Einwirkungsprodukte von Harzen, wie Kolophonium oder Fichtenharz oder der diesen Harzen zugrunde liegenden Harzsäuren, auf Phenole oder deren Substitutionsprodukte oder Analoge, wie man sie z. B. nach dem Verfahren des Patents 581.956 erhält, mit Alkoholen verestert und dann mit Formaldehyd, dessen Polymeren oder anderen Aldehyden gesättigter oder ungesättigter Natur, gegebenenfalls in Gegenwart eines Kondensationsmittels, behandelt.Process for the preparation of resinous condensation products Es it has been found that industrially valuable condensation products are obtained if the non-ester-like action products of resins such as rosin or spruce resin or the resin acids on which these resins are based, phenols or their substitution products or analogs, such as one such. B. obtained by the method of patent 581,956, with Esterified alcohols and then with formaldehyde, its polymers or other aldehydes saturated or unsaturated nature, optionally in the presence of a condensing agent, treated.
Die neuen Produkte unterscheiden sich vom Ausgangsmaterial durch einen erhöhten Erweichungspunkt und eine verminderte Acetylzahl; in fetten Ölen und Kohlenwasserstoffen sind sie leicht löslich.The new products differ from the original material in one increased softening point and decreased acetyl number; in fatty oils and hydrocarbons they are easily soluble.
Beispiel i Zu einer Mischung von 300 Gewichtsteilen Kolophonium (amerikanisches, Säurezahl 16q., Jodzahl 175, Acetylzahl 5, Erwaichungspunkt 79°) und 40o Gewichtsteilen Tetrachlorkohlenstoff werden Zoo Gewichtsteile einer 25prozentigen Lösung von Börfluorid in technischem Rohkresol unter Rühren und Kühlung (1o°) innerhalb 4 Stunden zugegeben. Es entsteht rasch eine dunkelbraune dickflüssige Masse, die dann bei Zimmertemperatur (15 bis 18°) noch weiter etwa 14 Stunden lang verrührt wird. Das anfallende Reaktionsprodukt wird hierauf in kaltes Wasser gegossen und mit Wasserdampf ausgeblasen. Man erhält so eine gelbstichige, ziemlich spröde, harzige Masse, welche mit Wasser ausgekocht wird und nach dem Schmelzen ein klares Harz liefert (325 Gewichtsteile). Das Harz zeigt einen Erweichungspunkt von 1o5°. 4oo Teile des so erhaltenen Kondensationsproduktes werden mit 31 Teilen Glycerin durch Erhitzen auf 25o bis 26o° verestert. Der anfallende Harzester (Säurezahl 2o, Erweichungspunkt r25°) wird innerhalb 31j2 Stunden bei 18o bis 25o° mit 16 bis 17 Gewichtsteilen Paraformaldehyd unter Rühren versetzt. Es entsteht eine dickflüssige klare Masse, die nach dem Erkalten einen Erweichungspunkt von 1q.5° zeigt. Sie ist schwer löslich in kaltem Alkohol, gut löslich dagegen in Benzin und Leinöl.Example i To a mixture of 300 parts by weight of rosin (American acid number 16q., Iodine number 175, acetyl number 5, heating point 79 °) and 40o parts by weight carbon tetrachloride, zoo parts by weight of a 25 percent solution of boron fluoride in technical raw cresol are added with stirring and cooling (10 °) within Added 4 hours. A dark brown viscous mass quickly forms, which is then stirred for another 14 hours at room temperature (15 to 18 °). The resulting reaction product is then poured into cold water and blown out with steam. A yellowish, rather brittle, resinous mass is obtained, which is boiled with water and after melting gives a clear resin (325 parts by weight). The resin shows a softening point of 105 °. 400 parts of the condensation product thus obtained are esterified with 31 parts of glycerol by heating to 25o to 26o °. The resulting rosin ester (acid number 20, softening point 25 °) is mixed with 16 to 17 parts by weight of paraformaldehyde with stirring at 180 to 25 ° within 31/2 hours. The result is a thick, clear mass which, after cooling, shows a softening point of 1q.5 °. It is sparingly soluble in cold alcohol, but readily soluble in gasoline and linseed oil.
Beispiel 2 Eine Lösung von Zoo Teilen ausgeschmolzenem Kopal (Säurezahl 9o, Jodzahl 1o2, Erweichungspunkt 9.8 bis 99°) in Zoo Teilen Solventnaphtha wird mit 7o Teilen einer 25prozentigen Lösung von Borfluorid in technischem Rohkresol unter Rühren und Kühlen (15 °) innerhalb 4 Stunden versetzt. Es bildet sich rasch eine dunkelbraune Masse, die noch 2o Stunden bei Zimmertemperatur verrührt wird. Das anfallende Reaktionsprodukt wird hierauf mit kaltem Wasser zersetzt und mit Wasserdampf ausgeblasen. Aus dem so behandelten Produkt erhält man durch Schmelzen ein gelbbraunes Harz mit einem Erweichungspunkt von 115 bis 116°. Zoo Teile dieses Kondensationsproduktes werden durch-3o- bis 35stündiges Kochen mit 36 Teilen Dodecylalkohol (KP" 145 bis 155°) verestert. Der anfallende Harzester (23o Teile) wird innerhalb 4 Stunden bei igo bis 23o° mit 8 Teilen Paraformaldehyd unter gutem Rühren versetzt. Unter geringer Wasserabspaltung bildet-sich eine dickflüssige Masse, die nach dem Erkalten ein klares Harz mit einem Erweichungspunkt von 134 bis 136° liefert. Beispiel 3 Verwendet man im Beispiel i statt des Paraformaldehyds 25 Teile Acetaldehyd, so erhält man ein klares Harz mit einem Erweichungspunkt von 115°.Example 2 A solution of zoo parts of molten copal (acid number 9o, iodine number 1o2, softening point 9.8 to 99 °) in zoo parts solvent naphtha is with 70 parts of a 25 percent solution of boron fluoride in technical raw cresol added with stirring and cooling (15 °) within 4 hours. It forms quickly a dark brown mass which is stirred for another 20 hours at room temperature will. The resulting reaction product is then decomposed with cold water and with Steam blown out. The product thus treated is obtained by melting a yellow-brown resin with a softening point of 115 to 116 °. Zoo parts of this The condensation product is obtained by boiling for 30 to 35 hours with 36 parts of dodecyl alcohol (KP "145 to 155 °) esterified. The resulting resin ester (23o parts) is within 4 hours at igo to 230 ° with 8 parts of paraformaldehyde with thorough stirring. With little dehydration, a viscous mass forms, which after the Cooling gives a clear resin with a softening point of 134 to 136 °. example 3 If 25 parts of acetaldehyde are used instead of paraformaldehyde in example i, then a clear resin with a softening point of 115 ° is obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41903D DE582848C (en) | 1931-06-25 | 1931-06-25 | Process for the production of resinous condensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41903D DE582848C (en) | 1931-06-25 | 1931-06-25 | Process for the production of resinous condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE582848C true DE582848C (en) | 1933-08-23 |
Family
ID=7190654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI41903D Expired DE582848C (en) | 1931-06-25 | 1931-06-25 | Process for the production of resinous condensation products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE582848C (en) |
-
1931
- 1931-06-25 DE DEI41903D patent/DE582848C/en not_active Expired
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