DE2245110A1 - IR hardenable unsatd polyester coating compsns - contg polyesters from bicycloheptane dimethanol or tricyclodecane dimethnaol - Google Patents
IR hardenable unsatd polyester coating compsns - contg polyesters from bicycloheptane dimethanol or tricyclodecane dimethnaolInfo
- Publication number
- DE2245110A1 DE2245110A1 DE19722245110 DE2245110A DE2245110A1 DE 2245110 A1 DE2245110 A1 DE 2245110A1 DE 19722245110 DE19722245110 DE 19722245110 DE 2245110 A DE2245110 A DE 2245110A DE 2245110 A1 DE2245110 A1 DE 2245110A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- polyesters
- polyester
- dimethnaol
- bicycloheptane
- 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.)
- Granted
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 13
- 229920000728 polyester Polymers 0.000 title abstract description 20
- 239000011248 coating agent Substances 0.000 title abstract description 4
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 title 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 title 1
- 150000002009 diols Chemical class 0.000 claims abstract description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
- 239000012190 activator Substances 0.000 claims abstract description 3
- 239000000654 additive Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 11
- 229920006305 unsaturated polyester Polymers 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 5
- 239000008096 xylene Substances 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- -1 ether groups Diols Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-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
- KTVZZJJSXSGJSX-UHFFFAOYSA-N carbonic acid;2-propan-2-ylperoxypropane Chemical compound OC(O)=O.CC(C)OOC(C)C KTVZZJJSXSGJSX-UHFFFAOYSA-N 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000465 moulding 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
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FWLKKPKZQYVAFR-LVEZLNDCSA-N (e)-but-2-enedioic acid;1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.N=1C2=CC=CC=C2N(CCOCC)C=1N1CCCN(C)CC1 FWLKKPKZQYVAFR-LVEZLNDCSA-N 0.000 description 1
- RAQPZQAQMHUKTB-ODZAUARKSA-N (z)-but-2-enedioic acid;methanol Chemical compound OC.OC(=O)\C=C/C(O)=O RAQPZQAQMHUKTB-ODZAUARKSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical group OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229960000325 emedastine Drugs 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004611 light stabiliser Substances 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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
- C08G63/02—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
-
- 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
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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)
Abstract
Description
Verwendung von ungesättigten Polyestermassen zur Herstellung von Überzügen Gegenstand der Erfindung ist die Verwendung von ungesättigten Polyestermassen besthend aus 1. einem ungesättigten Polyester 2. einem mit 1, mischpolymerisierbaren Vinylmonomeren 3. einem Aktivatorsystem 4. üblichen Hilfs- und Zusatzstoffen zur Horstellungs von Überzügen, welche durch Aushärtungmit Infrarostrahles mit einer Wellenlänge von 1 bis 5 w erhalten werden. Use of unsaturated polyester compositions for the production of Coatings The invention relates to the use of unsaturated polyester compositions consisting of 1. an unsaturated polyester 2. one with 1, copolymerizable Vinyl monomers 3. an activator system 4. customary auxiliaries and additives for Production of coatings, which by curing with infrared rays with a Wavelength of 1 to 5 w can be obtained.
Es ist bekarnt, daß ungesättigte Polyesterharze ais Form- und Überzugsma@ken nach Zusatz geeigneter Initiatoren und Beschleunigor bei Räumtemperatur zum Härten und Beschichten von Holz, Glas sowie Steinplatten eingesetzt werden können Die Polyestermassen konnen forner nach Zusatz von Füllstoffen als Spachtelmassen verwendet werden. Eine wesentliche Verkürzung der Härtungszeiten bis zur Stapel- und Schleiffähigkeit der beschichteten Flächen wird durch die Verwendung von UV-Strahlen und durch den Zusatz geeigneter UV-Sensibilisatoren möglich. Mittels UV-Strahlen können insbesondere Klarcke oder lasierend gefärbte Lacke gehärtet werden.It is known that unsaturated polyester resins are used as molding and coating materials after the addition of suitable initiators and accelerators at the room temperature for hardening and coating of wood, glass and stone slabs can be used The polyester masses can be used as fillers after the addition of fillers. One Significant reduction in curing times until the coated surfaces is made through the use of UV rays and through the addition suitable UV sensitizers possible. By means of UV rays, in particular Clear or translucent colored lacquers can be hardened.
Die mit UV-Strahlen gehärteten ungesättigten Polyesterharze zeigen allerdings den Nachteil, daß hellfarbig pigmentierte Lacke vergilben können, wofür die Anwesenheit des UV-Sensibilisators verantwortlich gemacht wird. Ein weiterer Nachteil ist es, daß füllstoffhaltige Spachtelmassen, besonders mit größeren Schichtdicken als 100 g, unvollständig aushärten, so daß beim Gebrauch Mängel wie Eißbildung oder Ablöserscheidungen Auftreten.The unsaturated polyester resins hardened with UV rays show however, the disadvantage that light-colored pigmented paints can yellow, for which reason the presence of the UV sensitizer is held responsible. Another The disadvantage is that filler-containing fillers, especially those with thick layers than 100 g, cure incompletely, so that defects such as pitting or Detachment distinctions occur.
Es ist bekannt, daß diese Nachteile mittels der Härtung durch Infrartostrahlen vermieden werden können (DT-OS 2 029 657).It is known that these disadvantages can be overcome by curing by infrared rays can be avoided (DT-OS 2 029 657).
Diese Art der Härtung ist besonders für Klarlacke, pigmentierte Lacke und hochgefüllte Spachtelmassen geeignet. Die Trocknungszeiten sind aber länger als bei der UV-Särtung.This type of hardening is especially useful for clear lacquers, pigmented lacquers and highly filled leveling compounds are suitable. However, the drying times are longer than with UV curing.
Diese längeren Bestrahlungszeiten verursachen in unerwünschtem Maße eine Erwärmung des Entergrundes, was häufig zur Bildung von Spannungsrissen führt. Es zeigte sich daß bei Verwendung herkömlicher Polyester die Bestrahlungszeiten nicht verkürzt werden können. Die Lackfilme härten dann gar nicht oder nur unvollständig aus Dies hat zur Folge, daß die Filme bei Behandlung mit Xylol anquellen oder sogar aufgelöst werden.These longer exposure times cause undesirable levels a heating of the boarding ground, which often leads to the formation of stress cracks. It was found that the irradiation times when using conventional polyesters cannot be shortened. The paint films then do not harden at all or only partially This has the consequence that the films swell or even swell on treatment with xylene to be resolved.
Als den DT-PSS 953 117 und 934 889 ist es bekannt. Diole der allgemeinen Formel für die Polyesterherstellung einzusetzen. Jedoch kann diesen Patentschriften nicht entnommen werden, daß gerade solche Polyester besonders gut für die Härtung mit Hilfe von Infrarotstrahlen geeignet sind.It is known as DT-PSS 953 117 and 934 889. Diols of the general formula to be used for polyester production. However, it cannot be inferred from these patents that precisely such polyesters are particularly suitable for curing with the aid of infrared rays.
Aufgabe der Erfindung war es, durch Verwendung von Polyestern geeigneter Zusammensetzung, Überzüge mit guten Eigenschaften herzustellen, welche durch Aushärtung durch Infrarotstrahlen erhalten werden können, und webei die oben aufgeführten Nachteile des Standes der Technik vermieden werden.The object of the invention was to make it more suitable by using polyesters Composition to produce coatings with good properties, which by curing can be obtained by infrared rays, and have the disadvantages listed above of the prior art can be avoided.
Diese Aufgabe wurde dadurch gelöst, daß die Diolkomponente des ungesättigien Polyesters 1 zu 40 bis 100 Molprozent aus einem Diol der allgomeinen Formel besteht.This object was achieved in that the diol component of the unsaturated polyester 1 consists of 40 to 100 mol percent of a diol of the general formula consists.
Die erfindungsgemäßen diole werden bevorzugt in Mengen von 70 bis 100 Molprozent eingesetzt.The diols according to the invention are preferably used in amounts from 70 to 100 mole percent used.
Für die erfindungsgemäßen ungesättigten Polyester werden für die Säurekomponente üblicherweise Fur@arsäure, Maleknsäure oder Maleinsäureanhydrid, ferner auch Itaconsäure oder Citraconsäure verwendet. Bis zu 50% der α,ß-ungesättigten, copolymerisationsfähigen Dicarbonsäuren können durch gesättigte Dicarbonsäuren, wie vor allem o-Phtalsäure oder o-Phthalsäureanhydrid, ferner Isophthalsäure, Bornstein- und Adipinsäure, Tetrachlor- oder Tetrabromphthalsäure oder Hexachlorrendomethylentetrahydrophthalsäure oder deren Anhydride ersetzt sein.For the unsaturated polyesters according to the invention, for the acid component usually fur @ aric acid, maleic acid or maleic anhydride, also itaconic acid or citraconic acid is used. Up to 50% of the α, ß-unsaturated, copolymerizable Dicarboxylic acids can be replaced by saturated dicarboxylic acids, especially o-phthalic acid or o-phthalic anhydride, also isophthalic acid, boron acidic and adipic acid, tetrachloro or tetrabromophthalic acid or hexachlororendomethylenetetrahydrophthalic acid or their anhydrides be replaced.
Neben den erfindungsgemäßen Diolen gignen sich zusätzlich die nachfolgend aufgeführten Diole für die Polyesterherstellung: Äthylenglykol-(1.2), Propandiol-(1.3), Butandiol-(1.4) oder Hexandiol-(1.69 als unverzweigtkettige, äthergruppenfreie Diole; Propandiol-(1.2), Butandiol-(1 .2) oder Butandiol-(1 .3), ferner Neopentylglykol als verzweigtkettige ätnergruppenfreie Diole; als äthergruppenhaltige unverzweigtkettige Diole eignen sich vor allem Diäthylen-, ferner auch Triäthylen- oder Tetra-Nitrylenglykol; als verzweigtkettige äthergruppenhaltige, vor allem Dipropylenglykol oder auch Tripropylenglykol.In addition to the diols according to the invention, the following also appear listed diols for polyester production: Ethylene glycol (1.2), Propanediol (1.3), butanediol (1.4) or hexanediol (1.69 as unbranched, ether group-free Diols; Propanediol (1.2), butanediol (1 .2) or butanediol (1 .3), also neopentyl glycol as branched-chain diols free from ether groups; as unbranched chain containing ether groups Diols are particularly suitable for diethylene glycol, and also triethylene glycol or tetra-nitrylene glycol; as branched chain containing ether groups, especially dipropylene glycol or tripropylene glycol.
Als ungesättigte, m@chpolymerisationsfähige Vinalmonomere eigneu sich die üblichen wie Styrol, substituierte Styrole, wie tert.-Butylstyrol oder α-Methylstyrol; ebenfalls auch Mischungen der letzteren mit Styrol. Andere äthylenisch ungesättigte Monomere, die in Kombination mit Styrol in Menge von weniger als 50 Gewichtsprozent, bezogen auf das Monomerengemisch, verwendet werden können, sind niedere (C1-C4)-Alkylester von Acrylsäure oder Methacrylsäure sowie halogenierte Styrole wie Chiorstyrol, Dichlorstyrol, ferner auch Diallylphthalat.Suitable as unsaturated, polymerizable vinyl monomers are the usual ones such as styrene, substituted styrenes such as tert-butylstyrene or α-methylstyrene; also mixtures of the latter with styrene. Other ethylenically unsaturated Monomers which, in combination with styrene in an amount of less than 50 percent by weight, Based on the monomer mixture, which can be used are lower (C1-C4) -alkyl esters of acrylic acid or methacrylic acid and halogenated styrenes such as chlorostyrene, dichlorostyrene, also diallyl phthalate.
Die Herstellung der ungesättigten Polyester erfolgt bei Temperaturen von 150 bis etwa 250°C durch übliche azeotrope oder Schmelzkondensation der Komponenten. Im allgemeinen werden die Diole in eimen etwa 2 bis 10 %igen molaren Überschuß gegenüber den Dicarbonsäuren eingesetzt. Das Molverhältnis Diole und Dicarbonsäuren ist jedoch nicht kritisch.The unsaturated polyesters are produced at temperatures from 150 to about 250 ° C. by customary azeotropic or melt condensation of the components. In general, the diols are used in about a 2 to 10% molar excess the dicarboxylic acids used. However, the molar ratio of diols and dicarboxylic acids is not critical.
Die Säurerahlen der ungesättigten Polyester liegen in allgerneinen zwischen 10 und 70, vorzugsweise bei 20 bis 50, insbesondere bei 25 bis 40. Dementsprechend liegt das Molekulargewicht, das nicht kritisch für die F,rfindung ist, zwischen 5500 und 800> vorzugsweise zwischen 3000 und 1000, insbesondere bei 2500 und 1500.The acid numbers of the unsaturated polyesters are in general between 10 and 70, preferably 20 to 50, in particular 25 to 40. Accordingly the molecular weight, which is not critical to the invention, is between 5500 and 800> preferably between 3000 and 1000, in particular at 2500 and 1500.
Zur Durchhärtung der Überzuge können Radikale bildende Satalysatoren wie Diacylperoxide z. B. Dibezoylperoxid, Dilaurylperoxid, Perester wie tert. -Buthylperbenzoat Hydroperoxide wie Cumly oder tert, -uthylroperoxid Ketonperoxide wie Methyläthylketon oder Cyclohexanonperoxide besonders geeignet sind die peroxycicarbonate, vor allem solche mit 3 bis 6 C-Atomen im Alkylrest wie zu Diisopropylperoxidicarbonat Di-tert -Buthylpertoxidicarbonat oder Dicyclohexylporoxidicarbonat in Mengem von 0,1 bis 3 gewichtprozent eingesetzt worden. Ebenso ist der Zuzatz von Härtungsbescheuigern wie totiärten aromatischen Aminen oder kobaltsalzen möglich.Catalysts which form free radicals can be used to harden the coatings such as diacyl peroxides e.g. B. dibezoyl peroxide, dilauryl peroxide, peresters such as tert. -Butyl perbenzoate Hydroperoxides such as Cumly or tert-butyl peroxide, ketone peroxides such as methyl ethyl ketone or cyclohexanone peroxides, the peroxycicarbonates are particularly suitable, above all those with 3 to 6 carbon atoms in the alkyl radical such as diisopropyl peroxidicarbonate di-tert -Butyl pertoxidicarbonate or dicyclohexylporoxidicarbonate in amounts from 0.1 to 3 percent by weight has been used. Likewise is the addition of hardening criminals such as hardened aromatic amines or cobalt salts are possible.
Die Polyesteemassen könen ferner übliche polymerisation pitoren beispielweise Hydrachinon, tert. -Buthilcatechol, Benzochion Di-tert-buthylbenzochinon und dergleichen imallge meinen etwa 0,001 bis etwa 0,1 Gewichtprozent, bezongen auf die Gesamtmiscfhung, enthalten.The polyester compositions can also pitor the usual polymerization, for example Hydroquinone, tert. -Buthilcatechol, benzochione di-tert-buthylbenzoquinone and the like generally mean about 0.001 to about 0.1 percent by weight, based on the total mixture, contain.
Weitere Hilfs und zusatzsteffe könen Fulstöffe pigmente, Paraffin Thixotropielmittel und/oder Lichtstabilisatoren sein.Other auxiliary and additional stiff filler pigments, paraffin Be thixotropic games and / or light stabilizers.
Die erfindungsgemäßen Polyestermassen zeichnet sich durch eine Peihe von guten Eigenschaften aus: Neben guten Allgemeineigenschaften wird bei der IR-Härtzug in kurzer Zeit eine schnelle Trockung und gute Derchhärtung der Überzüge erreicht. Die Trocknungzeit hängt dabei wesentlich von der eingesetzten Menge an erfindunggemäßen Diolen ab.The polyester compositions according to the invention are distinguished by a row from good properties: In addition to good general properties, the IR hardening tensile A quick drying and good hardening of the coatings achieved in a short time. The drying time depends essentially on the amount of material according to the invention used Diolen from.
Bie der Härtung hängen die Trocktungszeiten vom Anteil der erfindungsgemäßen plycycliscen Diohe im Ployester ab: Bei Verwendung von 0,5 Gewichtsprozent Paroxid bezongen auf die Polyeserformmasse, könen bei einem Diolanteil von 40 Molprozent an Tricyclodecandimethanol Troclrnungszeiten von ca. 3 Minuten, bei einem Anteil von ca. 60 Molprozent sogar Trocknungszeiten von weniger als 1 Minute erzielt werden. Es ist sogar möglich, diese uzen Trocknungszeiten durch zusätzliche Verwendung von Kobaltsalzen noch weiter zu senken.During the hardening, the drying times depend on the proportion of those according to the invention plycycliscen Diohe in Ployester from: When using 0.5 weight percent paroxide based on the polyester molding compound, with a diol content of 40 mol percent of tricyclodecanedimethanol drying times of about 3 minutes a proportion of approx. 60 mol percent even drying times of less than 1 minute be achieved. It is even possible to use these additional drying times Reduce the use of cobalt salts even further.
Wie die Ausführungen zeigen, können die erfindungsgemäßen Poly estermassen mit Hilfe von IR-Strahlen einfach und schnell verarbeitet wrden. Die Durchhärtung ist sehr gut, so daß erindungsgemäß hergestellte Überzüge bei einer Lagerung in Xylol nicht beeinträchtigt werden. Demgegenüber werden entsprechend gehärtete Polyesterüberzusgsmassen, daren polyester lediglich Propanidol-1 2 als Diol enthalten, nach Xylolbehandlung voll ständig aufgelöst.As the statements show, the polyester compositions according to the invention can processed easily and quickly with the help of IR rays. The hardening is very good, so that coatings produced according to the invention when stored in Xylene will not be affected. In contrast, suitably hardened polyester overlays, daren polyester only contain propanidol-1 2 as a diol, after xylene treatment fully resolved constantly.
Beispiele Ein Polyesterharz wurde auf Glasplatten (17 am x 7.3 cm) mit einem Filmaufziehgerät in einer Schichtdicke von 100µ aufgebracht, eine Stunde bei Raumtemperatur vorgetrocknet un: anschießend mit einem IR-Strahler Typ H 8 der Firma HERRAEUS gehärtet. Der Abstand zwischen Strahler und Lackfilm war 45 cm.Examples A polyester resin was applied to glass plates (17 am x 7.3 cm) applied with a film applicator in a layer thickness of 100μ, one hour predried at room temperature and then with an IR radiator type H 8 der HERRAEUS company hardened. The distance between the radiator and the paint film was 45 cm.
Der Versuch a enthält 0,5 Gewichtsprozent Isopropylperoxidcarbonat, Versuch b enthält 0,5 Gewichtsprozent Isopropoylperoxidcarbonat mit 1 Gewichtsprozent einer Kobaltoctoat-Lösung deren Kobaltgehalt 1% beträgt.Experiment a contains 0.5 percent by weight isopropyl peroxide carbonate, Experiment b contains 0.5 percent by weight of isopropyl peroxide carbonate with 1 percent by weight a cobalt octoate solution whose cobalt content is 1%.
Mit den nchfolgend aufgeführten Polyestern I bis IV bzw. A wurden die in der Tabelle I und II erhaltenen Ergebnisse er zielt. Die Zahlenwerte in den Tabellen geben die Pendellörte in sec. nach DIN 53 157 an. hierbei bedeutet der Wert v), daß die Probe direkt nach der Härtung gemessen wird, während der Wert n) die Pendelhärte angibt, nachdem die gehärtete Probe 15 Minuten in ein Xylolbad getaucht und anschließend eine Stunde lang bei Raumtemperatur getroclcnet worden war.The polyesters I to IV and A listed below were used the results obtained in Tables I and II he aims. The numerical values in the Tables give the pendulum marks in seconds according to DIN 53 157. here the value v) means that the sample is measured directly after curing, while the value n) indicates the pendulum hardness after the cured sample has been in a 15 minutes Immersed in a xylene bath and then dried for one hour at room temperature had been.
II 1 Mol Fumarsäure 1 Mol Fumarsäure 1 Mol Phthalsäureanhydr n d 1
Mol Phthalsäureanhydrid 0,83 Mol Tricydodecandi- 1,25 Mol Tricydodecandiethanol
methanol 1,85 Mol Diglykol 0,83 Mol Diglykol 33 % Styrol 33 % Styrol III IV 1 Mol
Fumarsäure 1 Mol Fumarsäure 1 Mol Phthalsäureanhydrid 4 Mol Phthalsäureanhydrid
1,66 Mol Tricydodecandi- 1 Mol Maleinsäure methanol 0,42 Mol Diglykol 6,18 Mol Tricydodecandimethanol
33 % Styrol 35 % Styrol
Tabelle I
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722245110 DE2245110C3 (en) | 1972-09-14 | Use of unsaturated polyester compounds for the production of coatings |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722245110 DE2245110C3 (en) | 1972-09-14 | Use of unsaturated polyester compounds for the production of coatings |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2245110A1 true DE2245110A1 (en) | 1974-03-21 |
| DE2245110B2 DE2245110B2 (en) | 1977-05-12 |
| DE2245110C3 DE2245110C3 (en) | 1977-12-22 |
Family
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538040A1 (en) * | 1974-08-29 | 1976-05-13 | Hoechst Ag | Curable unsaturated polyester mixture - contg polyester derived from polycarboxylic acid and or alcohol having norbornene or norbornane ring |
| EP0774492A3 (en) * | 1995-11-17 | 1999-04-21 | Kansai Paint Co., Ltd. | Putty composition |
| WO2003080703A1 (en) * | 2002-03-21 | 2003-10-02 | Degussa Ag | Unsaturated, amorphous polyesters based on determined dicidol isomers |
| EP1398337A3 (en) * | 2002-09-12 | 2004-05-19 | Degussa AG | Adhesion promoting additive from an unsaturated, amorphous polyester |
| EP1433805A1 (en) * | 2002-12-24 | 2004-06-30 | Degussa AG | Dispersions of amorphous, unsaturated polyester resins based on certain dicidol isomers |
| WO2006003044A1 (en) * | 2004-07-01 | 2006-01-12 | Degussa Ag | Radiation curable composition consisting of unsaturated amorphous polyesters and reactive dilutant agents |
| WO2006045661A1 (en) * | 2004-10-26 | 2006-05-04 | Degussa Gmbh | Use of an aqueous dispersion based on an unsaturated, amorphous polyester based on defined dicidol isomers |
| WO2006076974A1 (en) * | 2005-01-19 | 2006-07-27 | Degussa Gmbh | Aqueous, unsaturated, amorphous polyesters that are modified so as to be radiation curable |
| DE102007034866A1 (en) | 2007-07-24 | 2009-01-29 | Evonik Degussa Gmbh | Unsaturated polyester |
| DE102007034865A1 (en) | 2007-07-24 | 2009-01-29 | Evonik Degussa Gmbh | Coating compositions |
| DE102007057057A1 (en) | 2007-11-27 | 2009-05-28 | Evonik Degussa Gmbh | Uretdione group-containing polyurethane compositions which are curable at low temperature and contain adhesion-improving resins |
| WO2010118349A1 (en) * | 2009-04-09 | 2010-10-14 | Valspar Sourcing, Inc. | Polyester coating composition |
| US8367171B2 (en) | 2008-11-26 | 2013-02-05 | Valspar Sourcing, Inc. | Polymer having polycyclic groups and coating compositions thereof |
| US8449960B2 (en) | 2009-04-09 | 2013-05-28 | Valspar Sourcing, Inc. | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538040A1 (en) * | 1974-08-29 | 1976-05-13 | Hoechst Ag | Curable unsaturated polyester mixture - contg polyester derived from polycarboxylic acid and or alcohol having norbornene or norbornane ring |
| EP0774492A3 (en) * | 1995-11-17 | 1999-04-21 | Kansai Paint Co., Ltd. | Putty composition |
| US7144975B2 (en) | 2002-03-21 | 2006-12-05 | Degussa Ag | Unsaturated amorphous polyesters based on certain dicidol isomers |
| WO2003080703A1 (en) * | 2002-03-21 | 2003-10-02 | Degussa Ag | Unsaturated, amorphous polyesters based on determined dicidol isomers |
| EP1398337A3 (en) * | 2002-09-12 | 2004-05-19 | Degussa AG | Adhesion promoting additive from an unsaturated, amorphous polyester |
| US6794482B2 (en) | 2002-09-12 | 2004-09-21 | Degussa Ag | Adhesion promoter additive comprising an unsaturated, amorphous polyester |
| SG120936A1 (en) * | 2002-09-12 | 2006-04-26 | Degussa | Adhesion promoter additive comprising an unsaturated, amorphous polyester |
| EP1433805A1 (en) * | 2002-12-24 | 2004-06-30 | Degussa AG | Dispersions of amorphous, unsaturated polyester resins based on certain dicidol isomers |
| US6881785B2 (en) | 2002-12-24 | 2005-04-19 | Degussa Ag | Dispersions of amorphous unsaturated polyester resins based on particular Dicidol isomers |
| CN1324066C (en) * | 2002-12-24 | 2007-07-04 | 德古萨公司 | Dispersion of amorphous unsaturated polyester based on tricyclononane dimethanol isomeride |
| US7687569B2 (en) | 2004-07-01 | 2010-03-30 | Evonik Degussa Gmbh | Radiation curable composition consisting of unsaturated amorphous polyesters and reactive dilutant agents |
| CN1976972B (en) * | 2004-07-01 | 2011-08-03 | 赢创德固赛有限责任公司 | Radiation curable composition consisting of unsaturated amorphous polyesters and reactive dilutant agents |
| WO2006003044A1 (en) * | 2004-07-01 | 2006-01-12 | Degussa Ag | Radiation curable composition consisting of unsaturated amorphous polyesters and reactive dilutant agents |
| WO2006045661A1 (en) * | 2004-10-26 | 2006-05-04 | Degussa Gmbh | Use of an aqueous dispersion based on an unsaturated, amorphous polyester based on defined dicidol isomers |
| WO2006076974A1 (en) * | 2005-01-19 | 2006-07-27 | Degussa Gmbh | Aqueous, unsaturated, amorphous polyesters that are modified so as to be radiation curable |
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| DE102007034865A1 (en) | 2007-07-24 | 2009-01-29 | Evonik Degussa Gmbh | Coating compositions |
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| US8449960B2 (en) | 2009-04-09 | 2013-05-28 | Valspar Sourcing, Inc. | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
| US9187673B2 (en) | 2009-04-09 | 2015-11-17 | Valspar Sourcing, Inc. | Polyester coating composition |
| WO2010118349A1 (en) * | 2009-04-09 | 2010-10-14 | Valspar Sourcing, Inc. | Polyester coating composition |
| US9200176B2 (en) | 2009-04-09 | 2015-12-01 | Valspar Sourcing, Inc. | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
| CN102388080A (en) * | 2009-04-09 | 2012-03-21 | 威士伯采购公司 | Polyester coating composition |
| US10253138B2 (en) | 2009-04-09 | 2019-04-09 | The Sherwin-Williams Company | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
| US10563010B2 (en) | 2009-04-09 | 2020-02-18 | The Sherwin-Williams Company | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
| US10961344B2 (en) | 2009-04-09 | 2021-03-30 | The Sherwin-Williams Company | Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom |
| EP2853551A1 (en) | 2013-09-27 | 2015-04-01 | Evonik Industries AG | Additive for improving liquid adhesion and method for producing the same |
| DE102013219555A1 (en) | 2013-09-27 | 2015-04-02 | Evonik Industries Ag | Liquid adhesion-improving additive and process for its preparation |
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