CH397239A - Process for the production of polymers from monomeric vinyl compounds and unsaturated linear polyester resins - Google Patents
Process for the production of polymers from monomeric vinyl compounds and unsaturated linear polyester resinsInfo
- Publication number
- CH397239A CH397239A CH7231859A CH7231859A CH397239A CH 397239 A CH397239 A CH 397239A CH 7231859 A CH7231859 A CH 7231859A CH 7231859 A CH7231859 A CH 7231859A CH 397239 A CH397239 A CH 397239A
- Authority
- CH
- Switzerland
- Prior art keywords
- unsaturated
- polyester resins
- linear polyester
- vinyl compounds
- monomeric vinyl
- Prior art date
Links
- 229920001225 polyester resin Polymers 0.000 title claims description 10
- 239000004645 polyester resin Substances 0.000 title claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 9
- 229920000642 polymer Polymers 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- -1 tetrahydrophenyl Chemical group 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940093476 ethylene glycol Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- IGDCJKDZZUALAO-UHFFFAOYSA-N 2-prop-2-enoxypropane-1,3-diol Chemical compound OCC(CO)OCC=C IGDCJKDZZUALAO-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- OCNZHGHKKQOQCZ-CLFAGFIQSA-N [(z)-octadec-9-enoyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(=O)CCCCCCC\C=C/CCCCCCCC OCNZHGHKKQOQCZ-CLFAGFIQSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Verfahren zur Herstellung von Polymerisaten aus monomeren Vinylverbindungen und ungesättigten linearen Polyesterharzen
Es ist bekannt, Filme und gehärtete, geformte Gebilde durch Additionspolymeris ation monomerer Vinylverbindungen mit ungesättigten Polyesterharzen herzustellen. Als monomere Vinylverbindungen werden dabei vorzugsweise Styrol und Homologe des Styrols, wie Vinyltoluol, verwendet. Die ungesättigten linearen Polyesterharze werden durch Umsetzung von gesättigten zweiwertigen Alkoholen mit ss-ungesättig- ten Dicarbonsäuren oder deren Anhydriden, z. B. Ma leinsäureanhydrid oder Gemischen derselben mit gesättigten Dicarbonsäuren oder deren Anhydriden, z. B. Phthalsäureanhydrid, hergestellt. Bevorzugt werden dabei Gemische von Maleinsäureanhydrid und Phthalsäureanhydrid verwendet.
Als zweiwertige Alkohole werden z. B. Äthylenglykol oder Propylenglykol verwendet.
Es wurde nun gefunden, dass man glänzend und klebfrei trocknende Polymerisate aus monomeren Vinylverbindungen und ungesättigten Polyesterharzen erhält, wenn man als Ausgangsprodukte für die Herstellung der Polymerisate ungesättigte lineare Polyesterharze verwendet, die in ihrem Molekül
Endomethylentetrahydrophenyl-,
Endomethylenhexahydrophenyl-,
2,5 -Methylen-bicyclo-[O, 3, 4]-nonyl und/oder
2,5-Methylen-bicyclo-[0,3,4]-nonenyl-Reste enthalten und in der monomeren Vinylverbindung noch genügend löslich sind.
Die vorliegende Erfindung hat ein Verfahren zur Herstellung von glänzend und klebfrei trocknenden Polymerisaten aus monomeren Vinylverbindungen und ungesättigten, linearen Polyesterharzen zum Gegenstand, welches dadurch gekennzeichnet ist, dass die monomeren Vinylverbindungen polymerisiert werden mit ungesättigten linearen bis zu einer Säurezahl von 30 bis 50 kondensierten Polyesterharzen von Dicarbonsäuren, die mindestens teilweise a,ss-unge- sättigt sind, und zweiwertigen Alkoholen, von denen mindestens 20% mindestens einen der Reste Endomethylentetrahydrophenyl,
Endomethylenhexahydrophenyl, 2,5-Methylenbicyclo-[0,3 ,4]-nonyl und 2,5 -Methylenbicyclo-[O 3 ,4]-nonenyl aufweisen.
Der Endomethylentetrahydrophenyl-Rest besitzt die Formel I und der 2,5-Methylen-bicyclo-[0,3,4]nonenyl-Rest die Formel II:
EMI1.1
Der Endomethylenhexahydrophenyl-Rest und der 2, 5-Methylen-bicyclo-[0, 3, 4]-nonyl-Rest ergeben sich durch Hydrierung der Reste 1 bzw. II.
Die Reste der vorerwähnten Art können unmittelbar an die lineare Kette gebunden sein. Gemäss einer zweckmässigen Ausführungsform der Erfindung können die Reste über eine 1 bis 4 C-Atome enthaltende Kette, die durch Sauerstoff unterbrochen sein kann, an die lineare Polyesterkette gebunden sein.
Die ungesättigten linearen bis zu einer Säurezahl von 30 bis 50 kondensierten Polyesterharze sind erhältlich aus a, ss-ungesättigten Dicarbonsäuren, deren Anhydriden und/oder Estern und zweiwertigen Al koholen, von denen mindestens 20% mindestens einen der Reste Endomethylentetrahydrophenyl,
Endomethylenhexahydrophenyl,
2,5-Methylenbicyclo-[0,3,4]-nonyl und
2,5 -Methylenbicyclo-[0, 3 4]-nonenyl aufweisen.
Geeignete zweiwertige Alkohole dieser Art erhält man beispielsweise durch Anlagerung von Cyclopentadien an ungesättigte zweiwertige Alkohole wie Glycerin-monoallyläther, durch Umsetzung von Epichlorhydrin mit der Anlagerungsverbindung von Wasser an Dicyclopentadien unter Zusatz von Borfluorid und anschliessende Verseifung, durch Hydrierung der vorerwähnten, ungesättigten ASagerungs- produkte oder durch Verätherung von Pentaerythrit oder Trimethylolpropan mit dem Additionsprodukt von Cyclopentadien an Allylalkohol oder Crotylalkohol oder mit Dicyclopentadienylalkohol bzw. dessen Hydrierungsprodukt. Derartige Äther lassen sich auch direkt aus z. B.
Dicyclopentadien und Glycerin oder Pentaerythrit herstellen, wenngleich hierbei die nebeneinander entstehenden Mono-, Die und Triäther getrennt werden müssen.
Die erhaltenen Polymerisate trocknen glänzend und klebfrei, wenn man mindestens 20% der Glykole durch die gemäss dem erfindungsgemässen Verfahren anzuwendenden substituierten Glykole ersetzt.
Die nachfolgenden Beispiele erläutern die Erfindung:
Beispiel 1
196 g Maleinsäureanhydrid, 222 g Glycerinmono (2,5-methylenbicyclo-[0,3,4]-nonenyl)-äther und 62 g Äthylenglykol werden unter Zusatz von 200 cm3 Xylol bis zum Erreichen einer Säurezahl (SZ) von 39 mg KOH/g Polyesterlösung unter Auskreisen des Wassers verestert, das Lösungsmittel im Vakuum von 100 mm Hg bei 1600 C abgezogen, 0,015 % Hydrochinon als Stabilisator zugegeben und der Polyester mit 208 g Styrol bei 1200 C unter kräftigem Rühren verdünnt. Die auf Zimmertemperatur heruntergekühlte Polyesterlösung wird unter Zusatz von 1,6 % Methyläthylketonhydroperoxyd in Methyläthylketon und 0, % Kobaltnaphthenat in Styrol zu einem Film ausgehärtet, der nach 20 Minuten staubtrocken ist und sich nach 5 Stunden schleifen und polieren lässt.
Beispiel 2
196 g Maleinsäureanhydrid, 198 g GIycerinmono- (endomethylentetrahydrobenzyl)-äther, 62 g Äthylenglykol und 200 cm3 XyloI werden azeotrop wie im Beispiel 1 angegeben auf eine SZ von 40 mg KOH/g Polyesterlösung verestert, das Xylol im Vakuum abgezogen, 0, 0I5 % Hydrochinon zugegeben und mit 208 g Styrol verdünnt. Der nach Zusatz von Katalysator und Beschleuniger ausgehärtete Film war nach 4 Stunden schleif- und polierbar.
Beispiel 3
147 g Maleinsäureanhydrid, 74 g Pthalsäureanhydrid, 31 g Äthylenglykol, 38 g Propylenglykol und 156 g Endomethylenhexahydrophenylglykol werden mit 200 cm3 Xylol, wie im Beispiel 1 angegeben, bis zur SZ 38 mg KOH/g Polyesterlösung azeotrop verestert, 0,01% Hydrochinon zugegeben und mit 210 g Styrol bei 1200 C verdünnt. Der ausgehärtete Film war nach 20 Minuten staubtrocken und liess sich nach 5 Stunden schleifen und polieren.
Beispiel 4
196 g Maleinsäureanhydrid, 83 g Äthylenglykol, 214 g des Adduktes von Cyclopentadien an Pentaerythritdiallyläther werden mit 200 cm3 Xylol, wie im Beispiel 1 angegeben, bis zur SZ 43 mg KOH/g Polyesterlösung verestert, 0,015 % Hydrochinon zugegeben und mit 208 g Styrol bei 1200 C verdünnt.
Der ausgehärtete Film war nach 25 Minuten staubtrocken und nach 4 Stunden schleif- und polierbar.
Process for the production of polymers from monomeric vinyl compounds and unsaturated linear polyester resins
It is known to produce films and cured, shaped structures by addition polymerisation of monomeric vinyl compounds with unsaturated polyester resins. The monomeric vinyl compounds used are preferably styrene and homologues of styrene, such as vinyl toluene. The unsaturated linear polyester resins are made by reacting saturated dihydric alcohols with β-unsaturated dicarboxylic acids or their anhydrides, eg. B. Ma oleic anhydride or mixtures thereof with saturated dicarboxylic acids or their anhydrides, e.g. B. phthalic anhydride produced. Mixtures of maleic anhydride and phthalic anhydride are preferably used.
As dihydric alcohols, for. B. ethylene glycol or propylene glycol is used.
It has now been found that glossy and tack-free drying polymers are obtained from monomeric vinyl compounds and unsaturated polyester resins if the starting materials used for the preparation of the polymers are unsaturated linear polyester resins which have in their molecule
Endomethylenetetrahydrophenyl,
Endomethylene hexahydrophenyl,
2,5 -Methylene-bicyclo- [O, 3, 4] -nonyl and / or
Contain 2,5-methylenebicyclo- [0,3,4] -nonenyl radicals and are still sufficiently soluble in the monomeric vinyl compound.
The present invention relates to a process for the production of glossy and tack-free drying polymers from monomeric vinyl compounds and unsaturated, linear polyester resins, which is characterized in that the monomeric vinyl compounds are polymerized with unsaturated linear polyester resins condensed up to an acid number of 30 to 50 of Dicarboxylic acids which are at least partially a, ss-unsaturated, and dihydric alcohols, of which at least 20% of at least one of the radicals endomethylenetetrahydrophenyl,
Endomethylene hexahydrophenyl, 2,5-methylenebicyclo- [0.3, 4] -nonyl and 2,5-methylenebicyclo- [O3, 4] -nonenyl.
The endomethylenetetrahydrophenyl radical has the formula I and the 2,5-methylenebicyclo- [0,3,4] nonenyl radical has the formula II:
EMI1.1
The endomethylenehexahydrophenyl radical and the 2,5-methylenebicyclo- [0, 3, 4] -nonyl radical result from the hydrogenation of radicals 1 and II, respectively.
The residues of the type mentioned above can be linked directly to the linear chain. According to an expedient embodiment of the invention, the radicals can be attached to the linear polyester chain via a chain containing 1 to 4 carbon atoms which can be interrupted by oxygen.
The unsaturated linear polyester resins condensed up to an acid number of 30 to 50 are obtainable from α, β-unsaturated dicarboxylic acids, their anhydrides and / or esters and dihydric alcohols, of which at least 20% of at least one of the radicals endomethylenetetrahydrophenyl,
Endomethylene hexahydrophenyl,
2,5-methylenebicyclo- [0,3,4] -nonyl and
2,5-methylenebicyclo- [0, 3 4] -nonenyl.
Suitable dihydric alcohols of this type are obtained, for example, by adding cyclopentadiene to unsaturated dihydric alcohols such as glycerol monoallyl ether, by reacting epichlorohydrin with the addition compound of water to dicyclopentadiene with addition of boron fluoride and subsequent saponification, by hydrogenation of the aforementioned unsaturated products by etherification of pentaerythritol or trimethylolpropane with the addition product of cyclopentadiene with allyl alcohol or crotyl alcohol or with dicyclopentadienyl alcohol or its hydrogenation product. Such ethers can also be extracted directly from z. B.
Produce dicyclopentadiene and glycerol or pentaerythritol, although the mono-, die and triether that are formed next to one another must be separated.
The polymers obtained dry glossy and tack-free if at least 20% of the glycols are replaced by the substituted glycols to be used according to the process according to the invention.
The following examples explain the invention:
example 1
196 g of maleic anhydride, 222 g of glycerol mono (2,5-methylenebicyclo- [0,3,4] -nonenyl) -ether and 62 g of ethylene glycol are added with 200 cm3 of xylene until an acid number (AN) of 39 mg KOH / g polyester solution esterified with removal of the water, the solvent stripped off in a vacuum of 100 mm Hg at 1600 C, 0.015% hydroquinone added as stabilizer and the polyester diluted with 208 g styrene at 1200 C with vigorous stirring. The polyester solution, cooled down to room temperature, is cured with the addition of 1.6% methyl ethyl ketone hydroperoxide in methyl ethyl ketone and 0,% cobalt naphthenate in styrene to form a film which is dust-dry after 20 minutes and can be sanded and polished after 5 hours.
Example 2
196 g maleic anhydride, 198 g glycerol mono- (endomethylenetetrahydrobenzyl) ether, 62 g ethylene glycol and 200 cm3 xyloI are esterified azeotropically as indicated in Example 1 to an AN of 40 mg KOH / g polyester solution, the xylene is removed in vacuo, 0.015% Hydroquinone added and diluted with 208 g of styrene. The film hardened after the addition of catalyst and accelerator could be sanded and polished after 4 hours.
Example 3
147 g of maleic anhydride, 74 g of phthalic anhydride, 31 g of ethylene glycol, 38 g of propylene glycol and 156 g of endomethylene hexahydrophenylglycol are azeotropically esterified with 200 cm3 of xylene, as indicated in Example 1, up to 38 mg of KOH / g of polyester solution, 0.01% of hydroquinone is added and diluted with 210 g of styrene at 1200 C. The cured film was dust-dry after 20 minutes and could be sanded and polished after 5 hours.
Example 4
196 g of maleic anhydride, 83 g of ethylene glycol, 214 g of the adduct of cyclopentadiene with pentaerythritol diallyl ether are esterified with 200 cm3 of xylene, as indicated in Example 1, up to 43 mg of KOH / g of polyester solution, 0.015% of hydroquinone is added and 208 g of styrene at 1200 C diluted.
The cured film was dust-dry after 25 minutes and could be sanded and polished after 4 hours.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH0033062 | 1958-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH397239A true CH397239A (en) | 1965-08-15 |
Family
ID=7152043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7231859A CH397239A (en) | 1958-04-22 | 1959-04-21 | Process for the production of polymers from monomeric vinyl compounds and unsaturated linear polyester resins |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH397239A (en) |
-
1959
- 1959-04-21 CH CH7231859A patent/CH397239A/en unknown
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