DE1196868B - Process for hardening polyester molding compositions containing unsaturated nitrogen-containing polyesters - Google Patents
Process for hardening polyester molding compositions containing unsaturated nitrogen-containing polyestersInfo
- Publication number
- DE1196868B DE1196868B DEC28604A DEC0028604A DE1196868B DE 1196868 B DE1196868 B DE 1196868B DE C28604 A DEC28604 A DE C28604A DE C0028604 A DEC0028604 A DE C0028604A DE 1196868 B DE1196868 B DE 1196868B
- Authority
- DE
- Germany
- Prior art keywords
- polyesters
- compounds
- polyester
- molding compositions
- polyester molding
- 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
- 229920000728 polyester Polymers 0.000 title claims description 20
- 238000000465 moulding Methods 0.000 title claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 title description 8
- 229920006305 unsaturated polyester Polymers 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000012933 diacyl peroxide Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- -1 1-dimethylaminobenzene - 3,5 - dicarboxylic acid (dimethylamino-isophthalic acid) Chemical compound 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KNXVOGGZOFOROK-UHFFFAOYSA-N trimagnesium;dioxido(oxo)silane;hydroxy-oxido-oxosilane Chemical compound [Mg+2].[Mg+2].[Mg+2].O[Si]([O-])=O.O[Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O KNXVOGGZOFOROK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 238000004383 yellowing 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6858—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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0442—Catalysts
- C08F299/0457—Nitrogen containing compounds
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6928—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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)
- Compositions Of Macromolecular Compounds (AREA)
Description
Verfahren zum Härten von ungesättigte stickstoffhaltige Polyester enthaltende Polyester-Formmassen Es ist bekannt, Formmassen, die ungesättigte Polyester, monomere Vinyl- und/oder Allylverbindungen und neben Diacylperoxyden tertiäre Amine, vornehmlich Dimethylanilin, als Beschleuniger enthalten, bei Raumtemperatur auszuhärten. Die aus diesen Massen hergestellten Formteile verfärben sich insbesondere bei Bewitterung alsbald gelb bis braungelb, d. h., sie sind nicht vergilbungsbeständig. Zudem verfärben sich Dimethylanilin enthaltende Polyester-Formmassen beim Lagern in Gefäßen aus beispielsweise Weißblech dunkelblauviolett, was ihre Verwendbarkeit unter Umständen beschränkt.Method for curing unsaturated nitrogen-containing polyesters containing polyester molding compositions It is known molding compositions containing unsaturated polyester, monomeric vinyl and / or allyl compounds and, in addition to diacyl peroxides, tertiary amines, mainly dimethylaniline, contained as an accelerator, to cure at room temperature. The moldings made from these compositions discolor, especially when exposed to weathering soon yellow to brownish yellow, d. i.e., they are not resistant to yellowing. Also discolor polyester molding compositions containing dimethylaniline when stored in vessels for example, tinplate dark blue-violet, which indicates its usability under certain circumstances limited.
Nach der deutschen Patentschrift 919 431 werden tertiäre Amine der allgemeinen Formel worin R = Alkyl, Aryl, Aralkyl, Y und Z = OH, NH2, COOH, x= 1 bis 6 bedeutet, in ungesättigte Polyester einkondensiert und so mit organischen Peroxyden, vornehmlich Benzoylperoxyd, kalt härtende Polyester-Formmassen erhalten. Die daraus hergestellten Formteile sind jedoch dunkelgelb bis braun verfärbt und können nur dort verwendet werden, wo diese Eigenfarbe nicht stört.According to German patent specification 919 431, tertiary amines of the general formula where R = alkyl, aryl, aralkyl, Y and Z = OH, NH2, COOH, x = 1 to 6, condensed into unsaturated polyester and thus obtained with organic peroxides, primarily benzoyl peroxide, cold-curing polyester molding compounds. However, the molded parts made from it are discolored from dark yellow to brown and can only be used where this intrinsic color does not interfere.
Es ist ferner aus der belgischen Patentschrift 584487 bekannt, Polyester aus mehrwertigen Alkoholen und Säuren oder deren veresterbaren Derivaten herzustellen, wobei als Säurekomponenten Benzoll-amino- bzw. -l-alkylamino-3,5-dicarbonsäuren bzw. deren niedere Alkylester verwendet werden. Man erhält so in Kresolen, Xylolen oder Dimethylformamid lösliche Produkte, die nach dem Einbrennen lösungsmittel- und hitzebeständige, auf Metall fest haftende Uberzüge für beispielsweise elektrische Isolationen ergeben. It is also known from Belgian patent 584487, polyester to produce from polyhydric alcohols and acids or their esterifiable derivatives, where the acid components are benzene-amino- or -l-alkylamino-3,5-dicarboxylic acids or their lower alkyl esters can be used. This gives xylenes in cresols or dimethylformamide soluble products, which after stoving are solvent- and heat-resistant coatings that adhere firmly to metal, for example for electrical applications Isolations result.
Erfindungsgegenstand ist ein Verfahren zum Härten von Polyester-Formmassen, die ungesättigte stickstoffhaltige Polyester, an diese anpolymerisierbare monomere Vinyl- und/oder Allylverbindungen, organische Diacylperoxyde sowie gegebenenfalls Füll-und Farbstoffe enthalten, bei Raumtemperatur. Das Verfahren ist dadurch gekennzeichnet, daß man Massen aushärtet, die als stickstoffhaltige ungesättigte Polyester solche enthalten, in die tertiäre Aminoverbindungen der allgemeinen Formel wobei R1 = Wasserstoffatom oder Alkylgruppe, R2 und R3=Alkylgruppe bedeuten, in einer Menge von 0,5 bis 250/0, bezogen auf das Gewicht Polyester + Monomeren, durch Veresterung einkondensiert worden sind.The subject of the invention is a process for curing polyester molding compositions which contain unsaturated nitrogen-containing polyesters, monomeric vinyl and / or allyl compounds which can be polymerized onto them, organic diacyl peroxides and, if appropriate, fillers and dyes, at room temperature. The process is characterized in that compounds containing, as nitrogen-containing unsaturated polyesters, are cured into the tertiary amino compounds of the general formula where R1 = hydrogen atom or alkyl group, R2 and R3 = alkyl group, have been condensed in by esterification in an amount of 0.5 to 250/0, based on the weight of polyester + monomers.
Diese Aminoverbindungen werden in einen aus a,ß-ungesättigten Dicarbonsäuren bzw. deren Anhydriden sowie gegebenenfalls gesättigten Dicarbonsäuren und mehrwertigen Alkoholen in bekannter Weise hergestellten ungesättigten Polyester einkondensiert. These amino compounds are converted into one of α, β-unsaturated dicarboxylic acids or their anhydrides and optionally saturated dicarboxylic acids and polyvalent ones Alcohols in a known manner produced unsaturated polyester condensed.
Derartige Aminoverbindungen sind beispielsweise 1 - Dimethylaminobenzol - 3,5 - dicarbonsäure (Dimethylamino-isophthalsäure), deren Dimethyl- bzw. Such amino compounds are, for example, 1-dimethylaminobenzene - 3,5 - dicarboxylic acid (dimethylamino-isophthalic acid), its dimethyl or
Diäthylester, p-Dimethylamino-benzoesäuremethylester, p-Diäthylamino-benzoesäureäthylester.Diethyl ester, methyl p-dimethylamino-benzoate, ethyl p-diethylamino-benzoate.
Auf die Herstellung der verwendeten ungesättigten Polyester wird an dieser Stelle kein Schutz begehrt. On the production of the used unsaturated polyester is no protection is sought at this point.
Formmassen aus ungesättigten Polyestern, die die bezeichneten Aminoverbindungen enthalten, besitzen die eingangs erwähnten Nachteile nicht. Sie härten bereits bei Raumtemperatur zu hellgefärbten, widerstandsfähigen Formköpern aus. Molding compounds made from unsaturated polyesters containing the designated amino compounds contain, do not have the disadvantages mentioned at the beginning. They are already hardening Room temperature to light-colored, resistant moldings.
Die Eigenschaften der Formmassen werden hauptsächlich von den darin enthaltenen stickstoffhaltigen Polyestern bestimmt. Die günstigen Eigenschaften der erfindungsgemäß einkondensierten Aminocarbonsäuren in bezug auf die Härtung bei Raumtemperatur waren nicht vorauszusehen. The properties of the molding compounds are mainly determined by the properties in them contained nitrogenous Polyester. The cheap ones Properties of the aminocarboxylic acids condensed according to the invention in relation to curing at room temperature could not be foreseen.
Die Formmassen können ferner in bekannter Weise Füllstoffe, Farbstoffe oder faserige Verstärkungsmittel sowie erforderlichenfalls ultraviolettes Licht absorbierende Zusatzstoffe enthalten. The molding compositions can also contain fillers and dyes in a known manner or fibrous reinforcing agents and, if necessary, ultraviolet light contain absorbent additives.
Die Härtungsgeschwindigkeit kann durch die Menge des zugesetzten Peroxyds in gewissen Grenzen verändert werden. Sie kann einige Minuten oder mehrere Stunden betragen. Andererseits kann auch die Menge der erfindungsgemäß zu verwendenden Aminoverbindungen dem Verwendungszweck angepaßt werden. Dieses geschieht insbesondere bei der Herstellung von Zweikomponenten - Spachtelmassen, wobei die Füllstoffkomponente lediglich das Peroxyd, die Polyesterkomponente aber den das Amin enthaltenden Polyester enthält. The curing speed can be determined by the amount of added Peroxyds can be changed within certain limits. It can take a few minutes or several Hours. On the other hand, the amount to be used according to the invention can also be used Amino compounds are adapted to the intended use. This happens in particular in the production of two-component putties, with the filler component only the peroxide, the polyester component but the polyester containing the amine contains.
Beispiel 1 A. Herstellung des ungesättigten Polyesters (ohne Schutzanspruch) 24 g Dimethylamino-isophthalsäuredimethylester (Schmp. 124"C) werden zunächst mit 170 g 1,2-Propylenglykol unter Rühren und Schutzgas bei 170 bis 175"C in bekannter Weise umgeestert, bis ein Tropfen des Reaktionsgemisches klar abkühlt. Dann werden 148 g Phthalsäureanhydrid und 98 g Maleinsäureanhydrid zugegeben und die Schmelze wie üblich bei 190 bis 205"C zu einem ungesättigten Polyester mit der Säurezahl 35 bis 40 kondensiert und mit 0,07 g Hydrochinon stabilisiert. Example 1 A. Production of the unsaturated polyester (without protection claim) 24 g of dimethylamino-isophthalic acid dimethyl ester (melting point 124 "C) are initially with 170 g of 1,2-propylene glycol with stirring and protective gas at 170 to 175 "C in known Interesterified wise until a drop of the reaction mixture cools clear. Then will 148 g of phthalic anhydride and 98 g of maleic anhydride were added and the melt as usual at 190 to 205 "C to an unsaturated polyester with the acid number 35 to 40 condensed and stabilized with 0.07 g hydroquinone.
B. Erfindungsgemäßes Aushärten einer Polyester-Formmasse 65 g des nach A erhaltenen, ungesättigten Polyesters werden in 35g handelsüblichem Monostyrol gelöst. Die viskose Lösung wird mit 1 g Benzoylperoxyd homogen vermischt und in eine Form gegossen. B. According to the invention curing a polyester molding compound 65 g of the Unsaturated polyester obtained according to A are in 35g of commercially available monostyrene solved. The viscous solution is mixed homogeneously with 1 g of benzoyl peroxide and poured into poured a mold.
Die Formmasse geliert bei Raumtemperatur innerhalb einer Stunde und ist nach einigen weiteren Stunden zu einem klaren hellgelben Formkörper ausgehärtet.The molding compound gels at room temperature within an hour and has hardened to a clear, light yellow shaped body after a few more hours.
Beispiel 2 A. Herstellung des ungesättigten Polyesters (ohne Schutzanspruch) 134 g Phthalsäureanhydrid, 29 g Adipinsäure, 128 g Maleinsäureanhydrid und 152 g 1,2-Propylenglykol werden unter Rühren und Inertgas bei 185"C verestert, bis etwa die Hälfte des Kondensationswassers abdestilliert ist. Dem Ansatz wird das Reaktionsprodukt aus 48 g Dimethylamino-isophthalsäuredimethylester und 60 g 1,2-Propylenglykol, das zuvor bei 170 bis 175°C mit Hilfe von 1 ml 100/obiger Na- triummethylatlösung in Methanol umgeestert worden war, hinzugefügt, die Polykondensation der Mischung bei 200 bis 205"C und einer Säurezahl von etwa 35 beendet und der erhaltene Polyester mit 0,08 g Hydrochinon stabilisiert. Example 2 A. Production of the unsaturated polyester (without protection claim) 134 g of phthalic anhydride, 29 g of adipic acid, 128 g of maleic anhydride and 152 g 1,2-Propylene glycol are esterified with stirring and inert gas at 185 "C until about half of the condensation water has been distilled off. The reaction product is added to the batch from 48 g of dimethylamino-isophthalic acid dimethyl ester and 60 g of 1,2-propylene glycol, the previously at 170 to 175 ° C with the help of 1 ml 100 / above Na- trium methylate solution had been transesterified in methanol, added, the polycondensation of the mixture at 200 to 205 "C and an acid number of about 35 and the resulting polyester stabilized with 0.08 g hydroquinone.
B. Erfindungsgemäßes Aushärten einer Polyester-Formmasse Teil I 70 Gewichtsteile des ungesättigten Polyesters gemäßA, 30 Gewichtsteile Monostyrol. B. According to the invention, curing of a polyester molding compound Part I 70 Parts by weight of the unsaturated polyester according to A, 30 parts by weight of monostyrene.
Teil II 35 Gewichtsteile Kaolin, 8 Gewichtsteile Asbestine, 45 Gewichtsteile Eisenglimmer, 4.6 Gewichtsteile Benzoylperoxyd [85 0/oig] (inhibiert mit 1 15°/n Wasser), 7,4 Gewichtsteile Titandioxyd RN.Part II 35 parts by weight of kaolin, 8 parts by weight of asbestine, 45 parts by weight Iron mica, 4.6 parts by weight benzoyl peroxide [85%] (inhibited at 1 15% / n Water), 7.4 parts by weight of titanium dioxide RN.
Teil II wird mit Teil I bis zu einer spachtelfähigen Masse homogen vermischt, die auf getiefte Eisenbleche aufgestrichen wird. Die Masse erhärtet innerhalb 20 bis 30 Minuten und kann nach 2 bis 3 Stunden geschliffen und überlackiert werden. Part II becomes homogeneous with part I up to a level that can be troweled mixed, which is painted on deepened iron sheets. The mass hardens within 20 to 30 minutes and can be sanded and painted over after 2 to 3 hours.
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL297153D NL297153A (en) | 1962-12-07 | ||
| DEC28604A DE1196868B (en) | 1962-12-07 | 1962-12-07 | Process for hardening polyester molding compositions containing unsaturated nitrogen-containing polyesters |
| FR954364A FR1389482A (en) | 1962-12-07 | 1963-11-20 | Special amine compounds used in particular for the hardening of unsaturated polyester moldings |
| SE1356263A SE322626B (en) | 1962-12-07 | 1963-12-06 | |
| BE640930D BE640930A (en) | 1962-12-07 | 1963-12-06 | |
| GB4856263A GB985750A (en) | 1962-12-07 | 1963-12-09 | Improvements in or relating to hardening of unsaturated polyester compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28604A DE1196868B (en) | 1962-12-07 | 1962-12-07 | Process for hardening polyester molding compositions containing unsaturated nitrogen-containing polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1196868B true DE1196868B (en) | 1965-07-15 |
Family
ID=7018689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC28604A Pending DE1196868B (en) | 1962-12-07 | 1962-12-07 | Process for hardening polyester molding compositions containing unsaturated nitrogen-containing polyesters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE640930A (en) |
| DE (1) | DE1196868B (en) |
| GB (1) | GB985750A (en) |
| NL (1) | NL297153A (en) |
| SE (1) | SE322626B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0643088A1 (en) * | 1993-09-10 | 1995-03-15 | Xerox Corporation | Amino functional polyesters |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR70498E (en) * | 1955-11-24 | 1959-05-06 | Kodak Pathe | New photosensitive macromolecular compounds and their applications, in particular in photography |
| US2891929A (en) * | 1954-03-31 | 1959-06-23 | Eastman Kodak Co | Polyesters of a glycol, a dicarboxylic acid and an aminoacid |
| BE584487A (en) * | 1958-11-10 | 1960-03-01 | Bayer Ag | Polyester type coating compositions. |
-
0
- NL NL297153D patent/NL297153A/xx unknown
-
1962
- 1962-12-07 DE DEC28604A patent/DE1196868B/en active Pending
-
1963
- 1963-12-06 BE BE640930D patent/BE640930A/xx unknown
- 1963-12-06 SE SE1356263A patent/SE322626B/xx unknown
- 1963-12-09 GB GB4856263A patent/GB985750A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891929A (en) * | 1954-03-31 | 1959-06-23 | Eastman Kodak Co | Polyesters of a glycol, a dicarboxylic acid and an aminoacid |
| FR70498E (en) * | 1955-11-24 | 1959-05-06 | Kodak Pathe | New photosensitive macromolecular compounds and their applications, in particular in photography |
| BE584487A (en) * | 1958-11-10 | 1960-03-01 | Bayer Ag | Polyester type coating compositions. |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0643088A1 (en) * | 1993-09-10 | 1995-03-15 | Xerox Corporation | Amino functional polyesters |
Also Published As
| Publication number | Publication date |
|---|---|
| BE640930A (en) | 1964-04-01 |
| SE322626B (en) | 1970-04-13 |
| NL297153A (en) | |
| GB985750A (en) | 1965-03-10 |
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