DE889666C - Process for the production of paint raw materials - Google Patents
Process for the production of paint raw materialsInfo
- Publication number
- DE889666C DE889666C DEF1549A DEF0001549A DE889666C DE 889666 C DE889666 C DE 889666C DE F1549 A DEF1549 A DE F1549A DE F0001549 A DEF0001549 A DE F0001549A DE 889666 C DE889666 C DE 889666C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- raw materials
- production
- paint raw
- 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
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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/773—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Description
Verfahren zur Herstellung von Lackrohstoffen Es wurde gefunden, daß man durch Umsetzung von hydroxylgruppenhaltigen Estern aus Polyalkoholen und ungesättigten Carbonsäuren mit Isocyanaten und monomeren aromatischen Vinylverbindungen wertvolle Lackrohstoffe erhalten kann.Process for the production of paint raw materials It has been found that by reacting hydroxyl-containing esters of polyalcohols and unsaturated ones Carboxylic acids with isocyanates and monomeric aromatic vinyl compounds are valuable Can get paint raw materials.
Die Umsetzung der gekennzeichneten Ester mit den Isocyanaten und den aromatischen Vinylverbindungen kann in der Weise vorgenommen werden, daß man zunächst durch Umsetzung der hydroxylgruppenhaltigen Ester mit Isocyanaten die entsprechenden Urethane herstellt und diese dann mit den monomeren aromatischen Vinylverbindungen umsetzt. Man kann aber auch zunächst die hydroxylgruppenhaltigen Ester ungesättigter Carbonsäuren mit den monomeren aromatischen Vinylverbindungen umsetzen und diese Verbindungen dann durch Einwirkung von Isocyanaten zu den entsprechenden Urethanen umwandeln. Unter den hydroxylgruppenhaltigen Estern aus Polyalkoholen und ungesättigten Carbonsäuren, die als Ausgangsstoffe für das vorliegende Verfahren dienen können, seien insbesondere die durch Umesterung von natürlichen ungesättigten Ölen, wie z. B. Leinöl, Holzöl, Ricinusöl und Oiticicaöl mit Polyalkoholen, wie z. B. Glycerin, Pentaerythrit oder Trimethyloläthan, erhältlichen Mono- oder Diester genannt, fernerhin hydroxylgruppenhaltige Ester dieser Art vom Alkydharztyp, d. h. also solche, in denen die Reste mehrbasischer Carbonsäuren, wie z. B. der Phthalsäure, Bernsteinsäure, Adipinsäure oder Maleinsäure, enthalten sind.The implementation of the identified esters with the isocyanates and the aromatic vinyl compounds can be made in such a way that one first by reacting the hydroxyl-containing esters with isocyanates the corresponding Manufactures urethanes and then these with the monomeric aromatic vinyl compounds implements. But you can also first the hydroxyl-containing esters of unsaturated React carboxylic acids with the monomeric aromatic vinyl compounds and these Compounds then form the corresponding urethanes through the action of isocyanates convert. Among the hydroxyl-containing esters made from polyalcohols and unsaturated Carboxylic acids that can be used as starting materials for the present process, are in particular those by transesterification of natural unsaturated oils, such as z. B. linseed oil, wood oil, castor oil and oiticica oil with polyalcohols, such as. B. glycerine, Pentaerythritol or trimethylolethane, called available mono- or diesters, furthermore hydroxyl-containing esters of this type of the alkyd resin type, d. H. so those in which the residues of polybasic carboxylic acids, such as. B. phthalic acid, succinic acid, Adipic acid or maleic acid.
Als Isocyanate eignen sich für das vorliegende Verfahren z. B. Phenylisocyanat, Dichlorphenylisocyanat, Cyclohexylisocyanat, das Isocyanat aus dem Palmfettamingemisch, ß-Dekalylisocyanat, i-Chlorphenylen -2, 4-diisocyanat, Toluylendiisocyanat und 1, 6-Hexämethylendiisocyanat. Statt der Isocyanate kann man auch Stoffe anwenden, die wie diese reagieren: so z. B. Urethane oder Additionsprodukte aus Isocyanaten und Verbindungen, die aktiven -Wasserstoff enthalten, die unter den Umsetzungsbedingungen unter Bildung von Isocyanat spaltbar sind, so z. B. die Additionsprodukte aus Isocyanaten und Acetessigester oder Malonester.As isocyanates are suitable for the present process, for. B. phenyl isocyanate, Dichlorophenyl isocyanate, cyclohexyl isocyanate, the isocyanate from the palm fatty amine mixture, ß-decalyl isocyanate, i-chlorophenylene -2, 4-diisocyanate, tolylene diisocyanate and 1,6-hexaemethylene diisocyanate. Instead of isocyanates, you can also use substances who react like this: B. urethanes or addition products of isocyanates and compounds containing active hydrogen, which under the reaction conditions are cleavable with the formation of isocyanate, e.g. B. the addition products of isocyanates and acetoacetic ester or malonic ester.
Die nach dem vorliegenden Verfahren erhältlichen Lackrohstoffe zeichnen sich vor allem durch eine besonders hohe Härte und Wasserfestigkeit der daraus hergestellten Filme aus.Draw the paint raw materials obtainable according to the present process mainly due to the particularly high hardness and water resistance of the products made from it Movies from.
Beispiel i Zu 15o Gewichtsteilen eines in bekannter Weise aus 78 Gewichtsteilen Leinöl, 5 Gewichtsteilen Glycerin und 18 Gewichtsteilen i-Chlorphenylen-2, 4-diisocyanat hergestellten Urethanleinöls wird bei 140 bis 15o° eine Lösung aus 15o Gewichtsteilen Styrol in ioo Gewichtsteilen Xylol im Verlauf von 2o Stunden zugegeben. Die Lösung wird nach beendeter Styrolzugabe noch io Stunden auf 14o bis 15o° erhitzt. Man erhält eine klare Lösung mit einem Festgehalt von 63,8 %. Die aus dieser Lösung erhaltenen Filme trocknen innerhalb i/2 Stunde klebfrei auf und zeichnen sich durch große Härte und Widerstandsfähigkeit gegen Chemikalien aus.EXAMPLE i A solution of 150 parts by weight of styrene in 100 parts by weight of xylene is added at 140 to 150 parts by weight of a urethane linseed oil prepared in a known manner from 78 parts by weight of linseed oil, 5 parts by weight of glycerol and 18 parts by weight of i-chlorophenylene-2,4-diisocyanate Added 20 hours. After the addition of styrene has ended, the solution is heated to 140 to 150 ° for a further 10 hours. A clear solution with a solids content of 63.8 % is obtained . The films obtained from this solution dry tack-free within 1/2 hour and are characterized by great hardness and resistance to chemicals.
Beispiel 2 292 Gewichtsteile Leinöl werden mit 15,2 Gewichtsteilen Glycerin in bekannter Weise umgeestert. Zu dem auf 20o° erhitzten Umesterungsproduht werden innerhalb 15 Stunden 225 Gewichtsteile Styrol zugegeben. Dann wird die Temperatur noch 16 Stunden auf 200' gehalten. Nach dem Abkühlen auf 140' werden 42 Gewichtsteile Toluylendiisocyanat hinzugefügt. Dann wird 4 Stunden auf i4o° erhitzt. Das Reaktionsprodukt stellt ein klares zähflüssiges Harz dar, das sich in aromatischen Kohlenwasserstoffen oder Lackbenzin löst. Die 5o°/oige Lösung in Xylol besitzt eine Viskosität von 2o Sekunden, gemessen im DIN-Becher Nr. 4 bei 2o°. Die aus dieser Lösung hergestellten pigmentierten Lacke trocknen zu Filmen, die hohen Glanz, ausgezeichnete Wasserfestigkeit sowie eine vorzügliche Härte besitzen. Auch bei mehrtägiger Alterung bei 7o° verspröden diese, Filme nicht.Example 2 292 parts by weight of linseed oil are combined with 15.2 parts by weight Glycerine transesterified in a known manner. To the transesterification product heated to 20o ° 225 parts by weight of styrene are added within 15 hours. Then the temperature held at 200 'for another 16 hours. After cooling to 140 'it is 42 parts by weight Toluylene diisocyanate added. Then it is heated to 140 ° for 4 hours. The reaction product is a clear, viscous resin that turns into aromatic hydrocarbons or white spirit dissolves. The 50% solution in xylene has a viscosity of 20 Seconds, measured in DIN cup no. 4 at 20 °. Those made from this solution pigmented paints dry into films that have high gloss, excellent water resistance and have an excellent hardness. They become brittle even after aging at 7o ° for several days these, films not.
Beispiel 3 292 Gewichtsteile Leinöl werden mit 19,2 Gewichtsteilen Glycerin in bekannter Weise umgeestert. Das Umesterungsprodukt wird in der in Beispiel 2 beschriebenen Weise mit 25o Gewichtsteilen Styrol und hierauf mit 48,3 Gewichtsteilen Hexamethylendiisocyanat zur Umsetzung gebracht. Das Reaktionsprodukt stellt ein klares zähflüssiges Harz dar, aus dem sich mit Lackbenzin oder aromatischen Kohlenwasserstoffen Lösungen von 50 °/o Festgehalt herstellen lassen. Die Lösungen trocknen innerhalb 4 Stunden klebfrei auf; die erhaltenen Filme zeichnen sich durch hohen Glanz und gute Härte aus.Example 3 292 parts by weight of linseed oil are combined with 19.2 parts by weight Glycerine transesterified in a known manner. The transesterification product is in the example 2 with 25o parts by weight of styrene and then with 48.3 parts by weight Hexamethylene diisocyanate brought to implementation. The reaction product ceases clear viscous resin, made up of mineral spirits or aromatic hydrocarbons Prepare solutions with a solids content of 50%. The solutions dry inside 4 hours tack-free; the films obtained are characterized by high gloss and good hardness.
Beispiel 4 3oo Gewichtsteile eines in bekannter Weise aus 255 Gewichtsteilen Leinöl, 8o Gewichtsteilen Glycerin und 155 Gemzchtsteilen Phthalsäureanhydrid gewonnenen Alkydharzes mit der Säurezahl ii und der Viskosität einer 4o°/oigen Lösung in Lackbenzin von 7o Sekunden, gemessen im DIN-Becher Nr. 4 bei 2o' werden in 35o Gewichtsteilen Xylol gelöst. Dann werden bei iio bis i2o° allmählich 51 Gewichtsteile Phenylisocyanat zugesetzt. Nach Zugabe von 135 Gewichtsteilen Styrol wird sodann 30 Stunden auf 14o° erhitzt. Der Styrolgehalt des von flüchtigen Bestandteilen befreiten Reaktionsproduktes beträgt etwa 25 °/o. In 5o°/Qiger Xylollösung liegt die Viskosität bei 5o Sekunden, gemessen im DIN-Becher Nr. 4 bei 2o°. Die daraus gewonnenen Lacke zeichnen sich durch schnelle Trocknung aus und ergeben klare, harte Filme von guter Wasserfestigkeit.Example 4 300 parts by weight of an alkyd resin obtained in a known manner from 255 parts by weight of linseed oil, 80 parts by weight of glycerol and 155 parts by weight of phthalic anhydride with the acid number ii and the viscosity of a 40% solution in mineral spirits of 70 seconds, measured in DIN beaker no 2o 'are dissolved in 35o parts by weight of xylene. Then 51 parts by weight of phenyl isocyanate are gradually added at 110 to 120 °. After adding 135 parts by weight of styrene, the mixture is then heated to 140 ° for 30 hours. The styrene content of the reaction product freed from volatile constituents is about 25%. In 50 ° / qiger xylene solution the viscosity is 50 seconds, measured in DIN cup no. 4 at 20 °. The varnishes obtained from this are characterized by fast drying and result in clear, hard films with good water resistance.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF1549A DE889666C (en) | 1950-05-27 | 1950-05-28 | Process for the production of paint raw materials |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE295399X | 1950-05-27 | ||
DEF1549A DE889666C (en) | 1950-05-27 | 1950-05-28 | Process for the production of paint raw materials |
Publications (1)
Publication Number | Publication Date |
---|---|
DE889666C true DE889666C (en) | 1953-09-14 |
Family
ID=25782728
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF1549A Expired DE889666C (en) | 1950-05-27 | 1950-05-28 | Process for the production of paint raw materials |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE889666C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1052111B (en) * | 1956-08-30 | 1959-03-05 | Beck & Co G M B H Dr | Process for the production of elastic to tough plastics with shaping |
DE1098709B (en) * | 1958-08-20 | 1961-02-02 | Hoechst Ag | Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB573809A (en) * | 1942-07-28 | 1945-12-07 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of aromatic vinyl hydrocarbons with other polymerisable organic compounds and of coating compositions obtained therefrom |
GB609750A (en) * | 1946-02-15 | 1948-10-06 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of styrene with polyhydric alcoholic mixed esters and of coating compositions obtained therefrom |
-
1950
- 1950-05-28 DE DEF1549A patent/DE889666C/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB573809A (en) * | 1942-07-28 | 1945-12-07 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of aromatic vinyl hydrocarbons with other polymerisable organic compounds and of coating compositions obtained therefrom |
GB609750A (en) * | 1946-02-15 | 1948-10-06 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of styrene with polyhydric alcoholic mixed esters and of coating compositions obtained therefrom |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1052111B (en) * | 1956-08-30 | 1959-03-05 | Beck & Co G M B H Dr | Process for the production of elastic to tough plastics with shaping |
DE1098709B (en) * | 1958-08-20 | 1961-02-02 | Hoechst Ag | Process for accelerating the peroxide-induced curing of mixtures of unsaturated polyester resins and phosphorus-containing monomeric vinyl and allyl compounds |
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