DE767028C - Process for the production of non-alcoholic rosin pentaerythritol esters - Google Patents
Process for the production of non-alcoholic rosin pentaerythritol estersInfo
- Publication number
- DE767028C DE767028C DEC56135D DEC0056135D DE767028C DE 767028 C DE767028 C DE 767028C DE C56135 D DEC56135 D DE C56135D DE C0056135 D DEC0056135 D DE C0056135D DE 767028 C DE767028 C DE 767028C
- Authority
- DE
- Germany
- Prior art keywords
- rosin
- production
- fuel
- alcoholic
- pentaerythritol esters
- 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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims description 21
- 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 title claims description 19
- 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 title claims description 19
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 230000001476 alcoholic effect Effects 0.000 title 1
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 8
- 239000000446 fuel Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- 239000003973 paint Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012374 esterification agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur. Herstellung von spritlöslichen . Kolophonium-Pentaerythritestern Bei der Veresterung von Kolophonium mit Glycerin in äquivalenten Mengen entstehen praktisch neutrale Harze, die in Kohlenwasserstoffen, Estern, fetten ölen leicht löslich sind, sich aber in Sprit nicht lösen. Dasselbe gilt für die bekannte Veres.terung von Kolophonium mit der äquivalenten Menge Penta.-erythrit, wobei ebenfalls spritunlösliche Esterharze entstehen, die nur für Öllacke, Nitrocelluloselacke, nicht aber für Spritlacke verwendbar sind. Zur Herstellung von Spritlacken muß deshalb Kolophonium in sauer unveränderter Form eingesetzt werden, woraus sich aber erhebliche Verwendungsnachteile für die Spritlacke ergeben. Diese Nachteile bestehen einmal darin, daß das saure Kolophonium mit hasischen Pigmenten, wie z. B. Zinkweiß, nicht verträglich ist und daß es außerdem infolge seines sauren Charakters im Film von alkalischen Reinigungsmitteln, wie Soda, sehr stark angegriffen wird.Procedure for. Manufacture of fuel soluble. Rosin pentaerythritol esters The esterification of rosin with glycerine is produced in equivalent amounts practically neutral resins that are in hydrocarbons, esters, fats oils easily are soluble, but do not dissolve in fuel. The same applies to the well-known fermentation of rosin with the equivalent amount of penta-erythritol, which are also insoluble in fuel Ester resins are produced which are only used for oil varnishes and nitrocellulose varnishes, but not for fuel varnishes are usable. For the production of spray paints, therefore, rosin must be acidic can be used in an unchanged form, but this results in considerable disadvantages in use for the fuel paints. These disadvantages consist in the fact that it is acidic Colophony with hasic pigments, such as B. zinc white, is not tolerated and that, as a result of its acidic character, in the film of alkaline cleaning agents, like soda, is very strongly attacked.
Es wurde nun gefunden, daß man aus Kolophonium und Pentaerythrit neutrale spritlösliche Ester herstellen kann, wenn man Pentaerythrit in größeren Mengen, als es dem äquivalenten Verhältnis zum Kolophonium entspricht, zur Veresterung einsetzt. Die obere Grenze liegt bei Anwendung äquimolekularer Mengen Kolophonium und Pentaerythrit. Die auf diese Weise hergestellten Esterharze sind bei sehr niedriger Säurezahl in Spiritus in den Mengenverhältnissen wie sie zur Herstellung von Spritlacken angewandt «,-erden, klar und restlos löslich. Daneben lösen sie sich leicht in aromatischen. und aliphatischen Kohlenwasserstoffen, fetten Ölen, Estern, so daß sie zur Lackherstellung allgemein anwendbar sind. Als besonderer Vorteil der spritlöslichen Kolophoniumpentaerytliritester ist ihre größere Härte und höhere Viskosität gegenüber dem zugrundeliegenden Kolophonium zu erwähnen, die eine höhere Ausgiebigkeit des Harzes bei der Lackherstellung und Bildung härterer, klebfreier Filme zur Folge haben. Beispiele i. 32oTeileportugiesisches Kolophonium mit Säurezahl 175 (entsprechend i Mol Abietinsäure) werden mit 136 Teilen Pentaerythrit (= i Mol) auf 250 bis 26o° erhitzt. Nach 6stündigem Erhitzen ist die Säurezahl auf etwa 9 heruntergegangen. Das zu Beginn des Erhitzens trübe Harz ist in der Kälte klar und beliebig in Sprit löslich. Nach weiterem istündigem Erhitzen fällt die Säurezahl auf 5,6, und das in der Kälte klare Harz löst sich nur noch in. der Kälte im Verhältnis i : .I in Spiritus.It has now been found that neutral fuel-soluble esters can be prepared from rosin and pentaerythritol if pentaerythritol is used for the esterification in larger amounts than corresponds to the equivalent ratio to the rosin. The upper limit is when using equimolecular amounts of rosin and pentaerythritol. The ester resins produced in this way are clear and completely soluble with a very low acid number in alcohol in the proportions as they are used for the production of spray paints. In addition, they easily dissolve in aromatic ones. and aliphatic hydrocarbons, fatty oils, esters, so that they are generally applicable to paint production. A particular advantage of the petrol-soluble rosin pentaerytlirite esters is their greater hardness and higher viscosity compared to the underlying rosin, which results in a higher yield of the resin in paint production and the formation of harder, tack-free films. Examples i. 32o parts of Portuguese rosin with acid number 175 (corresponding to 1 mole of abietic acid) are heated to 250 to 260 ° with 136 parts of pentaerythritol (= 1 mole). After 6 hours of heating, the acid number has dropped to about 9. The resin, which is cloudy at the beginning of the heating process, is clear in the cold and freely soluble in fuel. After heating for an additional hour, the acid number falls to 5.6, and the resin, which is clear when cold, only dissolves in alcohol in the cold in a ratio of 1: 1.
Das in dieser Weise veresterte Kolophonium hat einen höheren Schmelzpunkt als das zugrundeliegendeKolophonium, und auch die Viskosität ist wesentlich höher als die des Ausgangsprodukts. Die Verbesserung in diesen Eigenschaften steigert die Härte der Filme und die Ausgiebigkeit der Harzlösungen.The rosin esterified in this way has a higher melting point than the underlying rosin, and also the viscosity is much higher than that of the starting product. The improvement in these properties increases the hardness of the films and the yield of the resin solutions.
In gleicher Weise läßt sich ein spritlöslich verestertes Kolophonium unter Anwendung des bisher gebräuchlichsten Veresterungsmittels, des Glycerins, nicht erreichen. Aus diesem Grunde war auch nicht vorauszusehen. daß Pentaery tlirit gerade zur Herstellung solcher neutraler spritlöslicher Harzester verwendet werden kann.In the same way, an esterified rosin which is soluble in fuel can be used using the most common esterification agent to date, glycerine, not reach. For this reason it could not be foreseen. that Pentaery tlirit are used precisely for the production of such neutral, fuel-soluble rosin esters can.
Beim Erhitzen von Kolophonium mit Glycerin in äquimolekularen Mengen entsteht ein trübes Harz, das schon beim Herabsinken der Säurezahl auf 2o in. Sprit praktisch unlöslich ist und das sich bei längerem Erhitzen auf 25o° (bis zu 12 Stunden und darüber) nicht ändert. Es bleibt in der Kälte trüb und in Alkohol unlöslich.When heating rosin with glycerin in equimolecular amounts the result is a cloudy resin which, when the acid number drops to 2o in is practically insoluble and that is when heated for a long time at 25o ° (up to 12 hours and above) does not change. It remains cloudy in the cold and insoluble in alcohol.
2. 32o Teile portugiesisches Kolophonium (entsprechend i Mol Abietinsäure) werden mit 113 Teilen Pentaerythrit (= °la '-\1o1) 61/z Stunden auf 23o° erhitzt. Es entsteht ein in der Kälte klares Harz mit Säurezahl 5, das in Sprit bis zum Verhältnis von i Teil Harzester zu 5 Teilen Alkohole löslich ist.2. 32o parts Portuguese rosin (equivalent to 1 mole of abietic acid) are heated with 113 parts of pentaerythritol (= ° la '- \ 101) 61 / z hours to 23o °. The result is a resin that is clear in the cold and has an acid number of 5, which in fuel up to the ratio from 1 part resin ester to 5 parts alcohols is soluble.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC56135D DE767028C (en) | 1940-11-28 | 1940-11-28 | Process for the production of non-alcoholic rosin pentaerythritol esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC56135D DE767028C (en) | 1940-11-28 | 1940-11-28 | Process for the production of non-alcoholic rosin pentaerythritol esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE767028C true DE767028C (en) | 1951-07-26 |
Family
ID=7028274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC56135D Expired DE767028C (en) | 1940-11-28 | 1940-11-28 | Process for the production of non-alcoholic rosin pentaerythritol esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE767028C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1820265A (en) * | 1928-11-24 | 1931-08-25 | Hercules Powder Co Ltd | Ester gum and method of producing |
| DE580282C (en) * | 1930-03-05 | 1933-07-11 | Louis Blumer Fa | Process for the production of resin acid compounds |
-
1940
- 1940-11-28 DE DEC56135D patent/DE767028C/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1820265A (en) * | 1928-11-24 | 1931-08-25 | Hercules Powder Co Ltd | Ester gum and method of producing |
| DE580282C (en) * | 1930-03-05 | 1933-07-11 | Louis Blumer Fa | Process for the production of resin acid compounds |
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