DE943258C - Process for the polymerization of vinyl compounds - Google Patents
Process for the polymerization of vinyl compoundsInfo
- Publication number
- DE943258C DE943258C DEF1959A DEF0001959A DE943258C DE 943258 C DE943258 C DE 943258C DE F1959 A DEF1959 A DE F1959A DE F0001959 A DEF0001959 A DE F0001959A DE 943258 C DE943258 C DE 943258C
- Authority
- DE
- Germany
- Prior art keywords
- vinyl compounds
- polymerization
- oil
- esters
- vinyl
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 9
- 238000006116 polymerization reaction Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 239000010775 animal oil Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-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
- 240000003085 Quassia amara Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- IUEMQUIQAPPJDL-UHFFFAOYSA-M sodium;2,3-dihydroxypropanoate Chemical compound [Na+].OCC(O)C([O-])=O IUEMQUIQAPPJDL-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 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
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Chemical class 0.000 description 1
- 239000008096 xylene 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
- 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
- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C08F242/00—Copolymers of drying oils with other monomers
-
- 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
- C09F7/08—Chemical modification of drying oils by isomerisation
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(WiGBI. S. 175)(WiGBI. P. 175)
AUSGEGEBEN AM 17. MAI 1956ISSUED MAY 17, 1956
Bekanntlich liefert die Polymerisation von Gemischen aus monomeren Vinylverbindungen, insbesondere aromatischen Vinylverbindungen, namentlich Styrol, und Estern mehrwertiger Alkohole mit Fettsäuren, die isolierte Doppelbindungen enthalten, trübe Produkte mit lacktechnisch unbefriedigenden Eigenschaften.It is known that the polymerization of mixtures of monomeric vinyl compounds, in particular aromatic vinyl compounds, namely styrene, and esters of polyhydric alcohols with Fatty acids that contain isolated double bonds, cloudy products with unsatisfactory paintwork Properties.
Es wurde nun gefunden, daß derartige Mischungen in technisch einfacher Weise in Gegenwart von Isomerisierungsmitteln zu klaren Produkten von lacktechnisch wertvollen Eigenschaften polymerisiert werden können. Unter den als Ausgangsstoffe für das vorliegende Verfahren geeigneten Estern von mehrwertigen Alkoholen, wie Glycerin, Trimethylolpropan oder Pentaerythrit, mit Fettsäuren, die isolierte Doppelbindungen enthalten, mögenIt has now been found that such mixtures in a technically simple manner in the presence of Isomerizing agents polymerized to give clear products with valuable properties in terms of paint technology can be. Among the esters suitable as starting materials for the present process of polyhydric alcohols, such as glycerine, trimethylolpropane or pentaerythritol, with fatty acids, containing isolated double bonds
z. B. vegetabilische oder tierische Öle, wie Leinöl, Sojaöl, Perillaöl, Sonnenblumenkernöl, Mohnöl und Tran genannt sein, ferner können auch Ester der gekennzeichneten Art vom Alkydharztyp, ao d. h. solche, die die Reste mehrbasischer Carbonsäuren, wie ζ. B. der Phthalsäure, Adipinsäure oder Maleinsäure enthalten, Verwendung rinden.z. B. vegetable or animal oils, such as linseed oil, soybean oil, perilla oil, sunflower seed oil, poppy seed oil and Tran may also be mentioned, and esters of the type indicated of the alkyd resin type, ao d. H. those that contain the residues of polybasic carboxylic acids, such as ζ. B. phthalic acid, adipic acid or Contain maleic acid, use bark.
Die lacktechnischen Eigenschaften der Polymerisationsprodukte lassen sich dadurch abwandein, daß man die vorerwähnten Ester im Gemisch mit anderen vegetabilischen oder tierischen Ölen, so z. B. Holzöl, Oiticicaöl, Menhaden- und Sardinenöl, verwendet.The coating properties of the polymerisation products can be altered by that the aforementioned esters are mixed with other vegetable or animal oils, so z. B. wood oil, oiticica oil, menhaden and sardine oil are used.
Als Vinylverbindungen können namentlich aromatische Vinylverbindungen, wie Styrol, α-Methylstyrol,-im Kern halogenierte Styrole und Vinyl-As vinyl compounds, in particular aromatic vinyl compounds such as styrene, α-methylstyrene, -im Core halogenated styrenes and vinyl
naphthalin, ferner aliphatisch^ Vinylverbindungen, . wie Vinylester, z. B. Vinylacetat, Acrylsäureester und Methacrylsäureester, Halogen- und Cyanvinylverbindungen, wie Vinylchlorid, Vinylidenchlorid und Arcylnitril, Vinyläther und Vinylketone, schließlich auch Mischungen der vorgenannten Verbindungen, eingesetzt werden.naphthalene, also aliphatic ^ vinyl compounds. such as vinyl esters, e.g. B. vinyl acetate, acrylic acid ester and methacrylic acid esters, halogen and vinyl cyanide compounds such as vinyl chloride, vinylidene chloride and acrylonitrile, vinyl ethers and vinyl ketones, finally also mixtures of the aforementioned compounds, can be used.
Gegebenenfalls kann die Polymerisation in Gegenwart eines Lösungsmittels, wie z. B. Benzol,Optionally, the polymerization in the presence of a solvent, such as. B. benzene,
ίο Chlorbenzol, Toluol, Xylol, Äthylbenzol und Terpentinöl, sowie Mischungen der vorgenannten aromatischen Kohlenwasserstoffe mit Benzin vorgenommen werden. Als Isomerisierungsmittel können im Rahmen der vorliegenden Erfindung die zur Isomerisierung von Ölen mit isolierten Doppelbindungen gebräuchlichen Stoffe Verwendung finden, so z. B. oberflächenaktive Stoffe, wie aktive Kohle, Aluminiumoxyd, isomerisierend wirkende Metalle in fein verteilter Form, wie Raney-Nickel und -Kobalt, auf Träger aufgebrachtes Nickel und Kobalt, alkalische Isomerisierungsmittel, wie Kaliumhydroxyd,, Magnesiumoxyd, Calciumoxyd, Alkoholate, wie Natriumalkoholat, Natriumglycerat, quaternäre Ammoniumverbindungen, wie Tetramethylammoniumhydroxyd, ferner Schwefeldioxyd. Im übrigen wird die Polymerisation in Gegenwart der Isomerisierungsmittel unter den für die Isomerisierung der vorliegenden Ester gebräuchlichen Bedingungen vorgenommen.ίο chlorobenzene, toluene, xylene, ethylbenzene and turpentine oil, and mixtures of the aforementioned aromatic hydrocarbons with gasoline will. As isomerizing agents in the context of the present invention, the for Isomerization of oils with isolated double bonds common substances are used, so z. B. surface-active substances such as active charcoal, aluminum oxide, isomerizing Metals in finely divided form, such as Raney nickel and cobalt, supported nickel and Cobalt, alkaline isomerizing agents such as potassium hydroxide, Magnesium oxide, calcium oxide, alcoholates such as sodium alcoholate, sodium glycerate, quaternary ammonium compounds, such as tetramethylammonium hydroxide, also sulfur dioxide. In addition, the polymerization in the presence of the isomerizing agent is among those for Isomerization of the present ester common conditions made.
Nach einem älteren Vorschlag kann man monomere Vinylverbindungen im Gemisch mit ungesättigte Fettsäuren enthaltenden Estern mehrwertiger Alkohole in Gegenwart eines aktivierten SiIikatkatalysators erhitzen. Die Verwendung solcher Silikatkatalysatoren wird hier nicht beansprucht.According to an older proposal, monomeric vinyl compounds can be mixed with unsaturated Esters of polyhydric alcohols containing fatty acids in the presence of an activated silica catalyst heat. The use of such silicate catalysts is not claimed here.
In 292 Gewichtsteile gereinigtes Leinöl werden bei, 1700 unter Rühren und Einleiten eines 'kräftigen Schwefeldioxydstromes im Laufe von 20 Stunden 250 Gewichtsteile Styrol eingetragen. Dann wird die Reaktionsmischung noch 10 Stunden unter Durchleiten von Schwefeldioxyd auf 1700 erhitzt. Nach dem Austreiben des Schwefeldioxyds mit Hilfe eines Stromes von Kohlendioxyd hinterbleibt ein hochviskoses, gelbes Öl, das nach dem Zusatz von Trockenstoff in einigen Stunden zu einem klären durchsichtigen Film klebfrei auftrocknet.250 parts by weight of styrene are introduced into 292 parts by weight of purified linseed oil at 170 ° while stirring and passing in a vigorous stream of sulfur dioxide over the course of 20 hours. Then, the reaction mixture is heated for 10 hours under passage of sulfur dioxide to 170 0th After the sulfur dioxide has been driven off with the aid of a stream of carbon dioxide, a highly viscous, yellow oil remains which, after the addition of dry matter, dries up to a clear, transparent film in a few hours without tackiness.
Verfährt man in der oben beschriebenen Weise ohne Durchleiten von Schwefeldioxyd, so erhält man ein Reaktionsprodukt, das trübe, lacktechnisch unbrauchbare Filme liefert.If one proceeds in the manner described above without passing through sulfur dioxide, so is obtained a reaction product which gives cloudy films which cannot be used for lacquer technology.
In 292 Gewichtsteile Leinöl, dem 30 Gewichtsteile Raney-Nickel zugesetzt wurden, werden bei 1700 innerhalb von 15 Stunden 250 Gewichtsteile Styrol unter Durchleiten von Kohlendioxyd eingetragen. Dann wird das Gemisch noch 16 Stunden auf 170° erhitzt. Das Reaktionsgemisch wird durch eine geheizte Filternutsche filtriert. Man erhält so ein gelbes, viskoses Öl, das nach Zusatz von Trokkenstoff in einigen Stunden klebfrei zu klaren durchsichtigen Filmen auftrocknet.In 292 parts by weight of linseed oil, the 30 parts by weight of Raney nickel were added, are entered at 170 0 within 15 hours of 250 parts by weight styrene, while passing carbon dioxide. The mixture is then heated to 170 ° for a further 16 hours. The reaction mixture is filtered through a heated suction filter. This gives a yellow, viscous oil which, after the addition of dry matter, dries tack-free to form clear, transparent films in a few hours.
Verwendet man bei dem oben beschriebenen Verfahren an Stelle des Raney-Nickels 50 Gewichtsteile aktive Kohle, so erhält man ebenfalls ein Öl, das nach Zusatz von Trockenstoff in wenigen Stunden klare durchsichtige Filme liefert.If, in the process described above, 50 parts by weight of active charcoal are used instead of Raney nickel, an oil is also obtained which after the addition of dry matter produces clear, transparent films in a few hours.
292 Gewichtsteile Sojaöl werden in Gegenwart von 30 Gewichtsteilen Raney-Nickel auf 2000 erhitzt. Dann gibt man innerhalb 15 Stunden 250 Gewichtsteile Styrol zu und erhitzt noch 16 Stunden auf 200°. Man erhält ein hochviskoses öl, das einen klaren homogenen Film liefert, der in einigen Tagen klebfrei auftrocknet.292 parts by weight of soybean oil are heated in the presence of 30 parts by weight of Raney nickel at 200 0th 250 parts by weight of styrene are then added over the course of 15 hours and the mixture is heated to 200 ° for a further 16 hours. A highly viscous oil is obtained which gives a clear, homogeneous film which dries up tack-free in a few days.
Verfährt man in der^ oben beschriebenen Weise jedoch ohne Zusatz von Raney-Nickel, so erhält man ein Reaktionsprodukt, das trübe, heterogene Filme liefert.If one proceeds in the manner described above but without the addition of Raney nickel, a reaction product is obtained that is cloudy, heterogeneous Films supplies.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF1959A DE943258C (en) | 1950-06-28 | 1950-06-29 | Process for the polymerization of vinyl compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1033898X | 1950-06-28 | ||
| DEF1959A DE943258C (en) | 1950-06-28 | 1950-06-29 | Process for the polymerization of vinyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE943258C true DE943258C (en) | 1956-05-17 |
Family
ID=25973670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF1959A Expired DE943258C (en) | 1950-06-28 | 1950-06-29 | Process for the polymerization of vinyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE943258C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB616044A (en) * | 1946-08-22 | 1949-01-14 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of aromatic vinyl hydrocarbons and oils |
-
1950
- 1950-06-29 DE DEF1959A patent/DE943258C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB616044A (en) * | 1946-08-22 | 1949-01-14 | Lewis Berger & Sons Ltd | Improvements in or relating to the manufacture of interpolymers of aromatic vinyl hydrocarbons and oils |
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