DE1035900B - Process for the production of copolymers for paints - Google Patents
Process for the production of copolymers for paintsInfo
- Publication number
- DE1035900B DE1035900B DEB40753A DEB0040753A DE1035900B DE 1035900 B DE1035900 B DE 1035900B DE B40753 A DEB40753 A DE B40753A DE B0040753 A DEB0040753 A DE B0040753A DE 1035900 B DE1035900 B DE 1035900B
- Authority
- DE
- Germany
- Prior art keywords
- oil
- paints
- parts
- production
- 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.)
- Pending
Links
- 239000003973 paint Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229920001577 copolymer Polymers 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims description 9
- ASFYWNCRQAWPEL-UHFFFAOYSA-N ethenylcyclooctatetraene Chemical compound C=CC1=CC=CC=CC=C1 ASFYWNCRQAWPEL-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- KDUIUFJBNGTBMD-UHFFFAOYSA-N cyclooctatetraene Chemical compound C1=CC=CC=CC=C1 KDUIUFJBNGTBMD-UHFFFAOYSA-N 0.000 claims 1
- 238000011161 development Methods 0.000 claims 1
- 230000018109 developmental process Effects 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 150000001993 dienes Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 241000396377 Tranes Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002023 wood 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
- C09F7/00—Chemical modification of drying oils
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verf ahren zur Herstellung von Mischpolymerisaten für Lacke Es ist bekannt, daß manche Eigenschaften von Lacken durch Umsetzung mit Dienen, z, B. Cyclooctatetraen verbessert werden können. Solche Lacke trocknen nicht immer genügend schnell und klebfrei.Process for the production of copolymers for paints It is known that some properties of paints by reaction with dienes, such as cyclooctatetraene can be improved. Such varnishes do not always dry quickly enough tack free.
Es wurde nun gefunden, daß man wertvolle Lacke erhält, wenn man Ester aus mehrwertigen Alkoholen und ungesättigten, trocknenden Fettsäuren mit Vinylcyclooctatetraen bei erhöhter Temperatur umsetzt. Alle natürlichen trocknenden und halbtrocknenden Ester aus mehrwertigen Alkoholen und ungesättigten Fettsäuren können verwendet werden, z. B. vegetabilische oder tierische Öle, wie Leinöl, Rizinusöl, Soiaöl, Holzöl, Mohnöl, Sonnenblumenöl, Baumwollsaatöl, Oiticicaöl, Perillaöl, Spermöl, Sardinenöl und Trane. Ferner sind z. B. einfache und gemischte Ester der den natürlichen Ölen zugrunde liegenden ungesättigten Fettsäuren auch mit anderen mehrwertigen Alkoholen, z. B. Trimethylolpropan oder Pentaerythrit, geeignet. Sie können außerdem mehrbasische gesättigte oder ungesättigte Carbonsäuren, wie Phthalsäure, Adipinsäure, Pimelinsäure, Korksäure, Azelainsäure und Sebaeinsäure oder Maleinsäure, enthalten.It has now been found that valuable paints are obtained if esters are used from polyhydric alcohols and unsaturated, drying fatty acids with vinylcyclooctatetraene Reacts at elevated temperature. All natural drying and semi-drying Esters from polyhydric alcohols and unsaturated fatty acids can be used z. B. vegetable or animal oils, such as linseed oil, castor oil, soia oil, wood oil, Poppy seed oil, sunflower oil, cottonseed oil, oiticica oil, perilla oil, sperm oil, sardine oil and Trane. Furthermore, z. B. simple and mixed esters of the natural oils underlying unsaturated fatty acids also with other polyhydric alcohols, z. B. trimethylolpropane or pentaerythritol, suitable. You can also use polybasic saturated or unsaturated carboxylic acids, such as phthalic acid, adipic acid, pimelic acid, Suberic acid, azelaic acid and sebaic acid or maleic acid.
Außer Vinvlcyclooctatetraen können auch seine Gemische mit bekannten Dienen verwendet werden, beispielsweise mit Phenylbutadien, wie sie z. B. bei der Herstellung von Cyclooctatetraen erhalten werden. Der Gehalt solcher Mischungen an Vinylcyclooctatetraen soll jedoch etwa 100j', nicht unterschreiten, weil sonst die Eigenschaften der erhaltenen Überzüge schlechter werden. je nach den gewünschten Eigenschaften der Lacke können etwa 10 bis 30 Teile Vinylcyclooctatetraen auf 100 Teile des trocknenden Öles angewandt werden, gegebenenfalls aber auch größere Mengen.In addition to Vinvlcyclooctatetraen its mixtures with known dienes can be used, for example with phenylbutadiene, as they are, for. B. obtained in the production of cyclooctatetraene. However, the vinylcyclooctatetraene content of such mixtures should not be less than about 100%, because otherwise the properties of the coatings obtained deteriorate. Depending on the desired properties of the paints, about 10 to 30 parts of vinylcyclooctatetraene can be used per 100 parts of the drying oil, but also larger amounts if necessary.
Die Reaktion wird zweckmäßig zwischen etwa 120 und 375'C und besonders vorteilhaft bei etwa 150 bis 280'C unter Rühren durchgeführt und erfordert dann im allgemeinen 2 bis 10 Stunden. Hierauf erwärmt man noch etwa 1 bis 3 Stunden bei etwa den gleichen Temperaturen, insbesondere auf etwa 280 bis 320'C. In manchen Fällen ist es günstig, Polymerisationskatalysatoren, insbesondere peroxydischer Konstitution, oder Sikkative, z. B. Kobaltnaphthenat oder Nickelenolat, oder auch Chinone oder Sauerstoff zuzugeben. Hierdurch läßt sich häufig die Reaktionstemperatur herabsetzen.The reaction is expediently carried out between about 120 and 375 ° C. and particularly advantageously at about 150 to 280 ° C. with stirring and then generally requires 2 to 10 hours. This is followed by heating for about 1 to 3 hours at about the same temperatures, in particular to about 280 to 320.degree. In some cases it is advantageous to use polymerization catalysts, in particular peroxide constitution, or siccatives, e.g. B. cobalt naphthenate or nickel enolate, or add quinones or oxygen. This often allows the reaction temperature to be reduced.
Man erhält klare Öle oder Harze, die viskoser als das Ausgangsprodukt sind. Sie enthalten keine im Hochvakuum flüchtigen Anteile.Clear oils or resins are obtained which are more viscous than the starting product are. They do not contain any volatile components in a high vacuum.
Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.
Beispiel 1
Eine Mischung aus 108Teilen Standöl und 20Teilen
eines Gemisches aus einem Teil Vinylcyclooctatetraen und 2 Teilen Phunylbutadien
wird im Verlauf von 15 Minuten unter Rühre#i zum Sic,#dc-i i#.-hitzt. A-.-,schließend
erhöht man die Temperatur während 4 Stunden auf 270 bis 275'C und erwärmt
danach noch 1 Stunde auf 300'C.
Das erhaltene Reaktionsprodukt ist
ein klares, viskoses 01 mit folzenden Kennzahlen:
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB40753A DE1035900B (en) | 1956-06-22 | 1956-06-22 | Process for the production of copolymers for paints |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB40753A DE1035900B (en) | 1956-06-22 | 1956-06-22 | Process for the production of copolymers for paints |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1035900B true DE1035900B (en) | 1958-08-07 |
Family
ID=6966179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB40753A Pending DE1035900B (en) | 1956-06-22 | 1956-06-22 | Process for the production of copolymers for paints |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE1035900B (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE713697C (en) * | 1939-03-01 | 1941-11-13 | Albert Ag Chem Werke | Process for improving the drying properties of oil-containing alkyd resins |
US2581413A (en) * | 1952-01-08 | Production of drying oils |
-
1956
- 1956-06-22 DE DEB40753A patent/DE1035900B/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2581413A (en) * | 1952-01-08 | Production of drying oils | ||
DE713697C (en) * | 1939-03-01 | 1941-11-13 | Albert Ag Chem Werke | Process for improving the drying properties of oil-containing alkyd resins |
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