CH200928A - Process for the production of a synthetic resin suitable for paint preparation. - Google Patents
Process for the production of a synthetic resin suitable for paint preparation.Info
- Publication number
- CH200928A CH200928A CH200928DA CH200928A CH 200928 A CH200928 A CH 200928A CH 200928D A CH200928D A CH 200928DA CH 200928 A CH200928 A CH 200928A
- Authority
- CH
- Switzerland
- Prior art keywords
- formaldehyde
- resin
- synthetic resin
- production
- dibutylphenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000003973 paint Substances 0.000 title claims description 7
- 229920003002 synthetic resin Polymers 0.000 title claims description 6
- 239000000057 synthetic resin Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- HLMLWEGDMMDCDW-UHFFFAOYSA-N 2-butylphenol;formaldehyde Chemical compound O=C.CCCCC1=CC=CC=C1O HLMLWEGDMMDCDW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 Ko balt Chemical compound 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung eines zur Lackbereitung geeigneten Kunstharzes. Das Hauptpatent Nr. 198722 betrifft ein Verfahren zur Herstellung eines zur Lack bereitunggeeignetenKunstharzes, das dadurch gekennzeichnet ist, dass man Butylphenol- Formaldehydharz soweit hydriert, dass die aromatischen Reste in hydroaromatische Reste übergeführt werden.
Die vorliegende Erfindung hat ein Ver fahren zur Herstellung eines zur Lackberei tung geeigneten Kunstharzes zum Gegen stande, das dadurch gekennzeichnet ist, dass man Dibatylphenol-Formaldebydharz soweit hydriert, dass die aromatischen Reste in hy- droaromatische Reste übergeführt werden.
Das Dibutylphenol-Formaldebydbarz kann als solches oder, was technisch zweckmässiger ist, in Gemischen verwendet werden, wie man sie durch Kondensation von Dibutylphenol mit Formaldehyd oder formaldehydabgeben- den Substanzen, wie Triogymethylen, Poly- ogymethylenen oder Paraformaldebyd oder Derivaten, wie He$amethylentetramin und dergl. erhält.
Die Kondensation des Dibutylphenols mit Formaldehyd usw. kann in Gegenwart eines sauer, neutral oder alkalisch reagierenden Kondensationsmittels, ferner in Anwesenheit von andern an sich bekannten Zusatzstoffen, gegebenenfalls in mehreren Stufen und unter nachträglichem Erhitzen stattfinden.
Das Dibutylphenol-Formaldehydharz kann nach an sich bekannten Hydrierungsverfahren hydriert werden. Die Hydrierung erfolgt vor teilhaft auf katalytischem Wege durch Ein wirkung von Wasserstoff bei erhöhten Tem peraturen und Überdruck in Anwesenheit von an sich bekannten Hydrierungskatalysatoren, wie Edelmetallen, ferner Nickel, Kupfer, Ko balt, Chrom bezw. von aus diesen Metallen oder deren Verbindungen bestehenden Misch katalysatoren. Man kann z. B. bei Tempera turen von 150-3000 und Drucken von 20-300 atü arbeiten.
Die Hydrierung des Dibutylphenol-Formaldehydharzes kann man vorzugsweise nach dessen Lösung in einem Lösungsmittel vornehmen. Das nach dem vorliegenden Verfahren gewonnene Harz ist besonders widerstands fähig gegen die verschiedensten Chemikalien, beispielsweise gegen Einwirkung von Alkalien. Es können sehr helle und lichtbeständige Harze gewonnen werden. Sie sind im allge meinen in den verschiedensten organischen Lösungsmitteln, beispielsweise in Kohlen- wasserstoffen und in Ölen löslich.
Ihre Eigen schaften machen sie zu wertvollen Lackroh- stoffen; sie finden als Weichmacher, filmbil- dendeMittelund Harzersatzstoffe Verwendung. Weiterhin lassen sich mit ihrer Hilfe wert volle Klebstoffe herstellen.
Beispiel: In 940 Gewichtsteile Phenol werden in Gegenwart von 167 ,Gewichtsteilen 60 %iger Perchlorsäure bei 70-$00 in einer mit Rück flusskühler versehenen Apparatur 1122 Ge wichtsteile a-Butylen eingeleitet.
206 Ge wichtsteile des so erhaltenen Di-sek.-Butyl- phenots werden in Gegenwart von 75 Ge- wichtsteilen 20%iger Schwefelsäure mit 75 Gewichtsteilen 40%iger Formaldehydlösung während 16 Stunden unter Rühren auf 1000 hitzt. Die zähe Masse wird in Anwesenheit eines Nickel enthaltenden Mischkatalysators bei einer ,
Temperatur von 2000 und einem Druck von 120 atü mittels Wasserstoff hy driert. Es wird ein sehr zähes, gelbliches Harz gewonnen, das in den üblichen Lack lösungsmitteln löslich ist.
Process for the production of a synthetic resin suitable for paint preparation. The main patent No. 198722 relates to a process for the production of a synthetic resin suitable for paint preparation, which is characterized in that butylphenol-formaldehyde resin is hydrogenated to such an extent that the aromatic residues are converted into hydroaromatic residues.
The present invention relates to a method for producing a synthetic resin suitable for paint preparation, which is characterized in that dibatylphenol-formaldehyde resin is hydrogenated to such an extent that the aromatic residues are converted into hydroaromatic residues.
The dibutylphenol-Formaldebydbarz can be used as such or, which is technically more expedient, in mixtures, such as can be obtained by condensation of dibutylphenol with formaldehyde or formaldehyde-releasing substances such as triogymethylene, poly-ogymethylenes or paraformaldebyd or derivatives such as He $ amethylenetetramine and like. Receives.
The condensation of the dibutylphenol with formaldehyde etc. can take place in the presence of an acidic, neutral or alkaline condensing agent, and also in the presence of other additives known per se, optionally in several stages and with subsequent heating.
The dibutylphenol-formaldehyde resin can be hydrogenated by hydrogenation processes known per se. The hydrogenation takes place before geous on the catalytic route by an action of hydrogen at elevated temperatures and overpressure in the presence of known hydrogenation catalysts, such as noble metals, also nickel, copper, Ko balt, chrome and respectively. of these metals or their compounds consisting of mixed catalysts. You can z. B. work at temperatures of 150-3000 and pressures of 20-300 atü.
The hydrogenation of the dibutylphenol-formaldehyde resin can preferably be carried out after it has been dissolved in a solvent. The resin obtained by the present process is particularly resistant to a wide variety of chemicals, for example to the action of alkalis. Very light and lightfast resins can be obtained. They are generally soluble in a wide variety of organic solvents, for example in hydrocarbons and in oils.
Their properties make them valuable paint raw materials; they are used as plasticizers, film-forming agents and resin substitutes. They can also be used to produce valuable adhesives.
Example: 1122 parts by weight of a-butylene are introduced into 940 parts by weight of phenol in the presence of 167 parts by weight of 60% strength perchloric acid at 70- $ 00 in an apparatus equipped with a reflux condenser.
206 parts by weight of the di-sec-butylphenot thus obtained are heated to 1000 for 16 hours with stirring in the presence of 75 parts by weight of 20% strength sulfuric acid with 75 parts by weight of 40% strength formaldehyde solution. The viscous mass is in the presence of a nickel-containing mixed catalyst at a,
Temperature of 2000 and a pressure of 120 atü using hydrogen hydrogenated. A very tough, yellowish resin is obtained that is soluble in the usual paint solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200928X | 1936-05-30 | ||
| CH198722T | 1937-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200928A true CH200928A (en) | 1938-10-31 |
Family
ID=25723174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200928D CH200928A (en) | 1936-05-30 | 1937-03-19 | Process for the production of a synthetic resin suitable for paint preparation. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200928A (en) |
-
1937
- 1937-03-19 CH CH200928D patent/CH200928A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE576177C (en) | Process for the production of resinous products from phenol condensation products and polyhydric alcohols | |
| CH200928A (en) | Process for the production of a synthetic resin suitable for paint preparation. | |
| EP0019151B1 (en) | Use of phenol-isobutyraldehyde-polycondensation products as laking agents for basic colorants | |
| EP0402743B1 (en) | Process for the production of di-(p-glycidoxycyclohexyl)-methane | |
| AT155968B (en) | Process for the production of synthetic resins. | |
| DE594197C (en) | Process for the production of resinous masses and lacquers | |
| DE973417C (en) | Process for the production of curable basic, nitrogen-containing phenolic resins | |
| DE720759C (en) | Process for the production of synthetic resins | |
| CH198722A (en) | Process for the production of a synthetic resin suitable for paint preparation. | |
| DE372855C (en) | Process for the preparation of synthetic resins | |
| DE552264C (en) | Process for the production of condensation products from urea or thiourea with aldehydes, in particular formaldehyde | |
| DE916465C (en) | Process for the production of condensation products | |
| DE848815C (en) | Process for the production of drying oils | |
| DE387836C (en) | Process for the preparation of resins | |
| DE836100C (en) | Process for the production of synthetic resins from polynuclear hydrocarbons | |
| DE671750C (en) | Process for the production of synthetic resins | |
| DE712701C (en) | Process for the production of phenol aldehyde resins suitable as paint base | |
| DE560604C (en) | Process for the production of paints from phenol-formaldehyde condensation products | |
| DE664648C (en) | Process for the production of polyvinyl acetals | |
| DE582847C (en) | Process for the production of condensation products from phenols, natural resins and aldehydes | |
| AT100564B (en) | Process for the production of condensation products. | |
| DE388795C (en) | Process for the preparation of condensation products from phenols and aldehydes | |
| DE387687C (en) | Method of making an adhesive | |
| DE615933C (en) | Lacquers or varnishes made from phenol-formaldehyde resitols | |
| AT226439B (en) | Process for the production of resins |