DE605688C - Process for the production of condensation products from phenols and natural resins - Google Patents
Process for the production of condensation products from phenols and natural resinsInfo
- Publication number
- DE605688C DE605688C DEI44379D DEI0044379D DE605688C DE 605688 C DE605688 C DE 605688C DE I44379 D DEI44379 D DE I44379D DE I0044379 D DEI0044379 D DE I0044379D DE 605688 C DE605688 C DE 605688C
- Authority
- DE
- Germany
- Prior art keywords
- phenols
- production
- natural resins
- condensation products
- acid
- 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 5
- 239000000025 natural resin Substances 0.000 title claims description 4
- 239000007859 condensation product Substances 0.000 title claims description 3
- 150000002989 phenols Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Kondensationsprodukten aus Phenolen und Naturharzen Nach dem Verfahren des Patents 581 956 werden Pheiiole- mit Naturharzen in Gegenwart von Kondensationsmitteln bei einer niedrigen, die gewöhnliche Raumtemperatur nicht wesentlich übersteigenden Reaktionstemperatur kondensiert.Process for the preparation of condensation products from phenols and natural resins According to the method of the patent 581 956 Pheiiole- with natural resins in the presence of condensing agents at a low, ordinary room temperature not significantly exceeding the reaction temperature condensed.
Es wurde nun gefunden, daß diese Kondensation auch bei Temperaturen, die wesentlich über der gewöhnlichen Raumtemperatur liegen, mit Vorteil durchgeführt werden kann, wenn man als Kondensationsmittel B,orfluoridoder Verbindungen des Borfluorids, wie Acidatofluorborsäure, Formiatofluorborsäure usw., benutzt. Die Anwendung von höheren Temperaturen bietet bei dieser Reaktion, abgesehen von der höheren Reaktiionsgeschwindigkeit, den Vorteil, daß man im allgemeinen geringere Mengen Kondensationsmittel benötigt als bei Temperaturen, die die Raumtemperatur nicht wesentlich übierschreiteal. Beispiel i Bei einer Temperatur von ungefähr 50° werden 6o Teile Addatofluorborsäure im Verlauf von i bis 2 Stunden zu- einer Mischung von 3oo Teilen Kolophonium (Säurezahl 168, Jodzahl 170, Erweichungspunkt 69o), i 5o Teilen Benzol und 7 5 Teilen technischem Rohkresol unter Rühren zugegeben. Nach 2o Stunden wird das Reaktionsprodukt in kaltes Wasser gegossen und das Lösungsmittel mit Wasserdampf verjagt; dann wird die Reaktionsmasse durch Waschen mit Wasser von der Säure befreit. Nach dem Schmelzen der so erhaltenen Reaktionsmasse erhält man ein klares Harz, das die folgenden Kennzahlen besitzt: Säurezahl 13q., Acetylzahl 68, Erweichungspunkt io6-bis 107°. Beispiel-In eine auf 7o bis 8o° jerhitzte Lösung von 3o Teilen Kolophonium in 15 Teilen Phenol wird während 8 Stunden ein kräftiger Strom Borfiuorid eingeleitet. Dann wird das unveränderte Phenol durch Abtreiben im. Dampfstrom entfernt. Als Reaktionsprodukt erhält man eine klare, gelbbraune, harzige, Masse mit folgenden Kennzahlen: Säurezahl 87,5, Acetylzahl 62,9, Jodzahl. 77,7, Verseifungszahl 113,6, Erweichungspunkt 117 bis i 18°. Eine Lösung dieser Masse in Essigsäureanhydrid zeigt nach Zusatz eines Tropfens konzentrierter Schwefelsäure eine gelbbraune Färbung.It has now been found that this condensation can also be carried out with advantage at temperatures which are substantially above normal room temperature if B, orfluoride or compounds of boron fluoride, such as acidatofluoroboric acid, formiatofluoroboric acid, etc., are used as the condensing agent. The use of higher temperatures in this reaction, apart from the higher reaction rate, has the advantage that, in general, smaller amounts of condensing agent are required than at temperatures which do not significantly exceed room temperature. EXAMPLE i At a temperature of about 50 °, 60 parts of addatofluoroboric acid are added over the course of 1 to 2 hours to a mixture of 300 parts of colophony (acid number 1 68, iodine number 170, softening point 69 °), 15 parts of benzene and 75 parts of technical crude cresol added with stirring. After 20 hours the reaction product is poured into cold water and the solvent is driven off with steam; then the reaction mass is freed from the acid by washing with water. After the reaction mass thus obtained has melted, a clear resin is obtained which has the following characteristics: acid number 13q., Acetyl number 68, softening point from 10 ° to 107 °. EXAMPLE A vigorous stream of boron fluoride is passed over 8 hours into a solution, heated to 70 to 80 °, of 30 parts of colophony in 15 parts of phenol. Then the unchanged phenol is driven off in the. Steam flow removed. The reaction product obtained is a clear, yellow-brown, resinous mass with the following parameters: acid number 87.5, acetyl number 62.9, iodine number. 77.7, saponification number 113.6, softening point 117 to 18 °. A solution of this mass in acetic anhydride shows a yellow-brown color after adding a drop of concentrated sulfuric acid.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44379D DE605688C (en) | 1932-05-07 | 1932-05-07 | Process for the production of condensation products from phenols and natural resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44379D DE605688C (en) | 1932-05-07 | 1932-05-07 | Process for the production of condensation products from phenols and natural resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE605688C true DE605688C (en) | 1934-11-16 |
Family
ID=7191272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI44379D Expired DE605688C (en) | 1932-05-07 | 1932-05-07 | Process for the production of condensation products from phenols and natural resins |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE605688C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE867914C (en) * | 1939-10-27 | 1953-02-19 | Albert Ag Chem Werke | Process for lightening fusible and non-hardenable, resinous condensation and polymerization products |
-
1932
- 1932-05-07 DE DEI44379D patent/DE605688C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE867914C (en) * | 1939-10-27 | 1953-02-19 | Albert Ag Chem Werke | Process for lightening fusible and non-hardenable, resinous condensation and polymerization products |
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