DE2500308A1 - Low-viscosity sprayable cross-linkable coating compsns - contg. liquid ester diols, polyisocyanates, opt diluents or solvents binders and pigments - Google Patents
Low-viscosity sprayable cross-linkable coating compsns - contg. liquid ester diols, polyisocyanates, opt diluents or solvents binders and pigmentsInfo
- Publication number
- DE2500308A1 DE2500308A1 DE19752500308 DE2500308A DE2500308A1 DE 2500308 A1 DE2500308 A1 DE 2500308A1 DE 19752500308 DE19752500308 DE 19752500308 DE 2500308 A DE2500308 A DE 2500308A DE 2500308 A1 DE2500308 A1 DE 2500308A1
- Authority
- DE
- Germany
- Prior art keywords
- coating composition
- polyisocyanates
- pigments
- solvents
- diluents
- 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
- -1 ester diols Chemical class 0.000 title claims abstract description 20
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 10
- 239000007788 liquid Substances 0.000 title claims abstract description 5
- 239000000049 pigment Substances 0.000 title claims description 8
- 239000003085 diluting agent Substances 0.000 title claims description 5
- 239000002904 solvent Substances 0.000 title claims description 4
- 238000000576 coating method Methods 0.000 title abstract description 10
- 239000011248 coating agent Substances 0.000 title abstract description 8
- 239000011230 binding agent Substances 0.000 title description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000008199 coating composition Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 238000005507 spraying Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 230000001680 brushing effect Effects 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 239000002023 wood Substances 0.000 abstract description 2
- 238000007654 immersion Methods 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 101150038956 cup-4 gene Proteins 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 2
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical class OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical class O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 230000003678 scratch resistant effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- METJRNPZJAUAGA-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpentanoic acid Chemical compound CCCC(C)(CO)C(O)=O METJRNPZJAUAGA-UHFFFAOYSA-N 0.000 description 1
- GOYVCPYTLIOSLQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)hexanoic acid Chemical compound CCCCC(CC)(CO)C(O)=O GOYVCPYTLIOSLQ-UHFFFAOYSA-N 0.000 description 1
- ZQWVBNYTPYVDQZ-UHFFFAOYSA-N 2-ethyl-3-hydroxyhexanoic acid Chemical compound CCCC(O)C(CC)C(O)=O ZQWVBNYTPYVDQZ-UHFFFAOYSA-N 0.000 description 1
- MANYTUDMEOGHHX-UHFFFAOYSA-N C(CCCCCCCC)C(CN=C=O)CCCCCCCCN=C=O Chemical compound C(CCCCCCCC)C(CN=C=O)CCCCCCCCN=C=O MANYTUDMEOGHHX-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OTNZTUMXZJDUOD-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1CC1CCCCC1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1CC1CCCCC1 OTNZTUMXZJDUOD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3221—Polyhydroxy compounds hydroxylated esters of carboxylic acids other than higher fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Vernetzbare tiberzugsmasse Die Errindung betrifft eine vernetzbare Uberzugsmasse aus einer Esterdiolkomponente A und einer Polyisocyanatkomponente B. Crosslinkable coating compound The invention relates to a crosslinkable Coating composition composed of an ester diol component A and a polyisocyanate component B.
Aus der DT-AS 2 304 893 sind lösungsmittelfreie Beschichtungsmittel bekannt, die ein aliphatisches oder cycloaliphatisches Polyisocyanat und eine äthergruppenfreie Polyhydroxylverbindung mit einem Molekulargewicht zwischen 200 und 2000 enthalten. Als Polyhydroxylverbindungen werden bevorzugt Polyesterpolyole eingesetzt. Derartige Beschichtungsmittel sind sehr hochviskos, so daß im allgemeinen ein- oder mehrwertige Alkohole als reaktive Verdünnter zugesetzt werden müssen. Trotzdem ist die Verspritzbarkeit dieser Beschichtungsmittel unbefriedigend. Außerdem läßt die Härte, Chemikalienfestigkeit und Temperaturbeständigkeit der ausgehärteten Uberzüge zu wünschen übrig. Setzt man sehr niedermolekulare Polyesterpolyole ein, so ergibt sich eine schlechte Benetzung der Pigmente, was zu einem geringen Glanz der Uberzüge führt. Die gleiche Erscheinung tritt auf, wenn man einfache Diole, wie z.B. Hexandiol oder Neopentylglykol, verwendet. Außerdem zeigen Uberzüge, die auf dieser Basis hergestellt werden, eine starke Feuchtigkeltsaufnahme Der Erfindung lag also die Aufgabe zugrunde, vernetzbare Uberzugsmassen herzustellen, welche niedrigviskos und damit gut spritzbar sind und harte, beständige Ueberzüge mit hohem Glanz ergeben.From DT-AS 2 304 893 are solvent-free coating agents known that an aliphatic or cycloaliphatic polyisocyanate and an ether group-free Contain polyhydroxyl compound with a molecular weight between 200 and 2000. Polyester polyols are preferably used as polyhydroxyl compounds. Such Coating agents are very viscous, so that they are generally monovalent or polyvalent Alcohols have to be added as reactive diluents. Nevertheless, the sprayability is this coating agent is unsatisfactory. Also leaves the hardness, chemical resistance and temperature resistance of the cured coatings leave something to be desired. Puts if very low molecular weight polyester polyols are used, poor wetting results the pigments, which leads to a poor gloss of the coatings. Same appearance occurs when using simple diols such as hexanediol or neopentyl glycol. In addition, coatings that are produced on this basis show a strong absorption of moisture The invention was therefore based on the object of producing crosslinkable coating compositions, which are of low viscosity and therefore easy to spray and have hard, permanent coatings result in high gloss.
Gegenstand der Erfindung ist eine vernetzbare Uberzugsmasse, enthaltend A) ein Esterdiol der allgemeinen Formel I mit einem Molekulargewicht zwischen 204 und 500 oder Gemische solcher Esterdiole, wobei die Komponente A einen Schmelzbereich unterhalb von 350C hat, und B) ein Polyisocyanat, wobei das Äquivalenzverhältnis der Isocyanat- zu den Hydroxylgruppen zwischen 0,7 : 1 und 1,3 : 1 liegt.The invention relates to a crosslinkable coating composition containing A) an ester diol of the general formula I with a molecular weight between 204 and 500 or mixtures of such ester diols, component A having a melting range below 350C, and B) a polyisocyanate, where the equivalence ratio the isocyanate to the hydroxyl groups is between 0.7: 1 and 1.3: 1.
Die Esterdiole haben die allgemeine Formel wobei R, R1 bis R7 Wasserstoff oder Alkylreste mit 1 bis 4 Kohlenstoffatomen sein können und R2 mit R3 sowie R5 mit R6 auch in Form eines Cycloalkylrings mit 5 bis 8 Kohlenstoffatomen verbunden sein können, mit der Maßgabe, daß in den Gruppen R1 bis R3 einerseits und R4 bis R7 andererseits Seweils mindestens zwei Reste Alkylreste sind.The ester diols have the general formula where R, R1 to R7 can be hydrogen or alkyl radicals with 1 to 4 carbon atoms and R2 with R3 and R5 with R6 can also be connected in the form of a cycloalkyl ring with 5 to 8 carbon atoms, with the proviso that in the groups R1 to R3 on the one hand and R4 to R7, on the other hand, are Seweils at least two groups alkyl groups.
Die Komponente A besteht aus Esterdiolen aus einem substituierten 1,3-Propandiol und einer substituierten 3-Hydroxypropionsäure oder Mischungen solcher Esterdiole. Diese können beispielsweise hergestellt werden durch disproportionierende Dimerisation entsprechender 3-Hydroxyaldehyde. NShere Einzelheiten finden sich in den deutschen Patentanmeldungen p (o.z. 31 071), P (O.Z. 31 082) und P (O.Z. 31 o83) , auf die hier ausdrücklich Bezug genommen wird. Das Molekulargewicht der Esterdiole liegt zwischen 204 und 500, vorzugsweise zwischen 204 und 400.Component A consists of a substituted ester diol 1,3-propanediol and a substituted 3-hydroxypropionic acid or mixtures thereof Ester diols. These can be produced, for example, by disproportionating Dimerization of the corresponding 3-hydroxyaldehydes. N For details, see the German patent applications p (o.z. 31 071), P (O.Z. 31 082) and P (O.Z. 31 o83), to which reference is expressly made here. The molecular weight of the ester diols is between 204 and 500, preferably between 204 and 400.
Wesentlich ist, daß die Komponente A bei Temperaturen unterhalb von 350C flüssig ist. Liegt der Schmelzbereich bei höheren Temperaturen, so ergeben sich Schwierigkeiten bei der Pigmentzubereitung, da höherschmelzende Esterdiole nach dem Anrelben mit Pigment auskristallisieren können und dann wieder Entmischung eintritt.It is essential that component A at temperatures below 350C is liquid. If the melting range is at higher temperatures, so result difficulties in pigment preparation, since higher melting ester diols Can crystallize out after tanning with pigment and then separate again entry.
Die Esterdiole liegen im allgemeinen nicht in reiner Form, sondern als Gemisch von Stereoisomeren vor.The ester diols are generally not in pure form, but rather as a mixture of stereoisomers.
Bevorzugte Esterdiole sind: Esterdiol 260 (2-Methyl-2-propylpropandiol-(1,3)-mono-(2-methyl-2-propyl-3-hydroxypropionat) Siedepunktl: 1540C Esterdiol 316 (2-Äthyl-2-butylpropandiol-(1,3)-mono-(2-äthyl-2-butyl-3-hydroxypropionat) Siedepunkt1-2: 180°C Esterdiol 288 (2-Äthylhexandiol-1,3-(2-äthyl-3-hydroxyhexanoat) Siedepunkt1: 148 bis 1500C Esterdiol 232 (2,2-Dimethylpropandiol-1,3-mono-(2-methyl-2-propyl-3.hydroxypropionat) Siedepunkt2: 140°C Esterdiol 284 Siedepunkt3: 196 bis 198"C Esterdiol 204 (2,2-Dimethylolpropandiol-(1,3)-mono-(2,2'-dimethyl-3-hydroxypropionat) Das Esterdiol 204 hat einen Schmelzpunkt von 51 0C und ist daher für sich allein nicht geeignet, wohl aber in flüssigen Gemischen mit anderen Esterdiolen.Preferred ester diols are: Esterdiol 260 (2-methyl-2-propylpropanediol- (1,3) -mono- (2-methyl-2-propyl-3-hydroxypropionate) Boiling point: 1540C Esterdiol 316 (2-ethyl-2-butylpropanediol- (1,3) -mono- (2-ethyl-2-butyl-3-hydroxypropionate) Boiling point 1-2: 180 ° C Esterdiol 288 (2-ethylhexanediol-1,3- (2-ethyl-3-hydroxyhexanoate) Boiling point 1: 148 to 1500C Esterdiol 232 (2,2-dimethylpropanediol-1,3-mono- (2-methyl-2-propyl-3rd hydroxypropionate) Boiling point 2: 140 ° C Esterdiol 284 Boiling point3: 196 to 198 "C Esterdiol 204 (2,2-dimethylolpropanediol- (1,3) -mono- (2,2'-dimethyl-3-hydroxypropionate) The ester diol 204 has a melting point of 51 ° C. and is therefore not suitable on its own, but it is suitable in liquid mixtures with other ester diols.
Die Komponente B besteht aus Polyisocyanaten, z.B. aromatischen Diisocyanaten, wie 1,5-Naphthylendiisocyanat, 2,4- oder 2,6-Toluylendiisocyanat; cycloaliphatisch-aromatischen Diisocyanaten, wie Phenylcyclohexylmethandiisocyanat; cycloaliphatisch/aliphatischen Diisocyanaten, wie 3-Isocyanatomethyl-3,5,5-aminoäthylcyclohexylisocyanat; aliphatischen Diisocyanaten, wie 2,2,4-Trimethylhexamethylendiisocyanat, 2-Nonyldecamethylendiisocyanat, l-Methyl-2,4-diisocyanatocyclohexan, Diisocyanatocyclohexan, Xylylendiisocyanat. Bevorzugt sind aliphatische bzw. cycloaliphatische Tri- und Tetraisocyanate, z.B. Derivate des Hexamethylendiisocyanats, wie Tris-(isocyanatohexyl)-biuret oder ein Gemisch aus Tris-(isocyanatohexyl).isocyanurat mit Bis-(isocyanatohexyl)-uretdion.Component B consists of polyisocyanates, e.g. aromatic diisocyanates, such as 1,5-naphthylene diisocyanate, 2,4- or 2,6-tolylene diisocyanate; cycloaliphatic-aromatic Diisocyanates such as phenylcyclohexylmethane diisocyanate; cycloaliphatic / aliphatic Diisocyanates such as 3-isocyanatomethyl-3,5,5-aminoethylcyclohexyl isocyanate; aliphatic Diisocyanates, such as 2,2,4-trimethylhexamethylene diisocyanate, 2-nonyldecamethylene diisocyanate, 1-methyl-2,4-diisocyanatocyclohexane, diisocyanatocyclohexane, xylylene diisocyanate. Aliphatic or cycloaliphatic tri- and tetraisocyanates, e.g. Derivatives of hexamethylene diisocyanate, such as tris (isocyanatohexyl) biuret or a Mixture of tris (isocyanatohexyl) isocyanurate with bis (isocyanatohexyl) uretdione.
Die Komponenten A und B werden in solchen Mengen eingesetzt, daß das Verhältnis der Isocyanat- zu den Hydroxylgruppen zwischen 0,7 : i und 1,3 : 1, vorzugsweise zwischen 0,8 : 1 und 1,2 : 1 liegt.Components A and B are used in such amounts that the Ratio of isocyanate to hydroxyl groups between 0.7: 1 and 1.3: 1, preferably is between 0.8: 1 and 1.2: 1.
Bei der erfindungsgemäßen Uberzugsmasse handelt-es sich um ein Zweikomponentensystem. Die beiden Komponenten A und B werden also getrennt gelagert und erst,kurz vor der Applikation zusammengegeben.The coating composition according to the invention is a Two-component system. The two components A and B are stored separately and only put together shortly before application.
Außer diesen beiden Komponehten kann die Überzugsmasse noch O bis 50, vorzugsweise 5 bis 15 Gewichtsprozent inerter Lösungsmittel enthalten, wie n-Butylacetat, Äthylglykolacetat, Methyläthylketon oder Xylol; oder reaktive Verdünner, z.B.In addition to these two components, the coating composition can also be from 0 to 50, preferably 5 to 15 percent by weight of inert solvents, such as n-butyl acetate, Ethyl glycol acetate, methyl ethyl ketone or xylene; or reactive diluents, e.g.
ein- oder mehrwertige Alkohole mit einem Siedepunkt über 120°C, wie Butandiol-1 4, Butyldiglykol oder Neopentylglykol. Die,se Lösungsmittel oder Verdünnungsmittel dienen - falls erforderlich - zur Erniedrigungder Viskosität zwei Lösungsmittel können in beiden Komponenten A oder B gleichermaßen enthalten sein. Die reaktiven Verdünner sind zweckmäßigerweise in der Komponente A enthalten, da ihre Hydroxylgruppen ebenfalls mit den Isocyanatgruppen der Komp'onente B reagieren können. Diese Hydroxylgruppen müssen daher bei der Einstellung des NCO : OH-Verhältnisses mit berücksichtigt werden. Die Uberzugsmasse kann außerdem zusätzlich bis zu 50 Gewichtsprozent, üblicher Bindemittel auf Basis; von hydroxylgruppenhaltigen Polymerisaten, Polykondensaten und Polyaddukten enthalten,-vorzugsweise in Mengen zwischen 10 und 30 Gewichtsprozent.monohydric or polyhydric alcohols with a boiling point above 120 ° C, such as Butanediol-1 4, butyl diglycol or neopentyl glycol. These solvents or diluents If necessary, two solvents are used to lower the viscosity can be contained in both components A or B equally. The reactive ones Thinners are expediently contained in component A, as their hydroxyl groups can also react with the isocyanate groups of component B. These hydroxyl groups must therefore be taken into account when setting the NCO: OH ratio. The coating composition can also contain up to 50 percent by weight of conventional binders based; of hydroxyl-containing polymers, polycondensates and polyadducts contain, -preferably in amounts between 10 and 30 percent by weight.
Auch deren Hydroxylgruppen müssen der Komponente A zugeschlagen werden. Durch Einbau derartiger hochmolekularer Polyole kann die Viskosität erhöht werden, es ergeben sich weitere Vernetzungsmöglichkeiten. Ferner sind die üblichen Zusätze an anderen Lackrohstoffen oder Lackhilfsmitteln, z.B.Their hydroxyl groups must also be added to component A. Incorporation of such high molecular weight polyols can increase the viscosity, there are further networking possibilities. There are also the usual additives on other paint raw materials or paint auxiliaries, e.g.
Celluloseester, Verlaufsmittel, Siliconöle, Weichmacher, Thixotropiermittel und Harze in üblichen Mengen möglich.Cellulose esters, leveling agents, silicone oils, plasticizers, thixotropic agents and resins possible in customary amounts.
Zur Einstellung der Reaktivität der Lacke können bekannte Katalysatoren, wie Zinnverbindungen, mitverwendet werden.To adjust the reactivity of the paints, known catalysts, such as tin compounds, are also used.
Die erfindungsgemäßen Überzugsmassen enthalten gewöhnlich Pigmente, wie Titandioxid, Ruß, organische oder anonganische Buntpigmente und Füllstoffe, wie Talkum oder Schwerspat, in Mengen von bis zu 100, vorzugsweise 3 bis 50 Gewichtsprozent.The coating compositions according to the invention usually contain pigments, such as titanium dioxide, carbon black, organic or inorganic colored pigments and fillers, such as talc or barite, in amounts of up to 100, preferably 3 to 50 percent by weight.
Die Pigmente und Füllstoffe werden zweckmäßigerweise mit der Komponente A vermischt.The pigments and fillers are expediently with the component A mixed.
Mit den Uberzugsmassen können beliebige Substrate, wie Metall, Holz oder Kunststoff nach üblichen Methoden, beispielsweise durch Sprühen, Streichen, Tauchen oder Airless-Spritzen beschichtet werden.Any substrates, such as metal, wood or plastic by conventional methods, for example by spraying, brushing, Dipping or airless spraying can be coated.
Die Aushärtung der Uberzugsmasse auf dem Substrat erfolgt im allgemeinen thermisch bei Temperaturen zwischen 50 und 250°C, besonders bevorzugt zwischen 80 und 1800C. Bei Verwendung sehr reaktionsfähiger Polyisocyanate oder bei Verwendung von Katalysatoren kann die Härtung auch bei Zimmertemperatur durchgeführt werden.The curing of the coating composition on the substrate generally takes place thermally at temperatures between 50 and 250 ° C., particularly preferably between 80 and 1800C. When using very reactive polyisocyanates or when using The curing of catalysts can also be carried out at room temperature.
Die in den Beispielen genannten Teile und Prozente beziehen sich auf das Gewicht.The parts and percentages given in the examples relate to the weight.
Beispiel 1 Komponente A: 100 Teile Esterdiol 260 247 Teile Titandioxid 10 Teile n-Butylacetat Komponente B: 196 Teile Tris-(isocyanatohexyl)-biuret, 75 Xig in Xylol/ Äthylglykolacetat 1 : 1-Lösung (DESMODUR# N) 19,5 Teile n-Butylacetat. Example 1 Component A: 100 parts ester diol 260 247 parts titanium dioxide 10 parts of n-butyl acetate component B: 196 parts of tris (isocyanatohexyl) biuret, 75 Xig in xylene / ethyl glycol acetate 1: 1 solution (DESMODUR # N) 19.5 parts of n-butyl acetate.
Die Viskosität der Mischung A + B beträgt etwa 100 Sekunden im Ford-Auslaufbecher 4 mm (DIN 53 211). Der Festkörpergehalt liegt bei 86,5 %. Die Lacklösung -wird auf entfettete Eisenbleche gespritzt. Nach dem Einbrennen bei 1200C bzw. 150°C jeweils 30 Minuten werden folgende Eigenschaften des Lackfilms (Schichtdicke 60µm) erhalten: Tabelle 30 1200C 302 1500C Pendelhärte nach König (DIN 53 157): 74 8ek. 147 Sek.The viscosity of mixture A + B is about 100 seconds in the Ford flow cup 4 mm (DIN 53 211). The solids content is 86.5%. The paint solution -will be on degreased iron sheets sprayed. After baking at 1200C and 150 ° C respectively The following properties of the paint film (layer thickness 60 µm) are obtained for 30 minutes: Tabel 30 1200C 302 1500C König pendulum hardness (DIN 53 157): 74 8ek. 147 sec.
Erichsentiefung (DIN 53 156): 11,0 10,7 Glanz nach Gardner 600 (ASTM D 523-67): 95 95 Biegeprobe + Kratzfestigkeit i. 0. i. 0.Erichsen depression (DIN 53 156): 11.0 10.7 gloss according to Gardner 600 (ASTM D 523-67): 95 95 bending test + scratch resistance i. 0. i. 0.
Beispiel 2 Komponente A: 100 Teile Esterdiol 316 221 Teile Titandioxid 10 Teile n-Butylacetat. Example 2 Component A: 100 parts ester diol 316 221 parts titanium dioxide 10 parts of n-butyl acetate.
Komponente B: 161 Teile DESMODUR N 0,02 Teile Dibutylzinn-dilaurat 21 Teile n-Butylacetat.Component B: 161 parts DESMODUR N 0.02 parts dibutyltin dilaurate 21 parts of n-butyl acetate.
Die Auslaufzeit der Mischung im Fordbecher 4 beträgt etwa 100 Sekunden, der Feststoffgehalt 86,2 %.The flow time of the mixture in the Ford cup 4 is about 100 seconds, the solids content 86.2%.
Eigenschaften des Lackfilms nach halbstündigem Einbrennen bei 120°C: Pendelhärte: 104 Sekunden Erlchsenwert: 11 Biegeprobe und Kratzfestigkeit; in Ordnung Glanz; 87.Properties of the paint film after stoving for half an hour at 120 ° C: Pendulum hardness: 104 seconds Erlchsenwert: 11 Bending test and scratch resistance; in order Shine; 87.
Beispiel 3 Komponente A: 100 Teile Esterdiol 316 215 Teile Titandioxid 10 Teile. n-Butylacetat. Example 3 Component A: 100 parts of ester diol 316, 215 parts of titanium dioxide 10 parts. n-butyl acetate.
Komponente Bt 115 Telie biuretgruppenhaltiges Polyisocyanat auf Basis von Hexamethylendiisocyanat und Diaminodicyclohexylmethan mit einem Isocyanatgehalt von 23,2 % und einer Viskosität bei 75°C von 183 cP 24 Teile n-Butylacetat.Component Bt 115 Telie based on polyisocyanate containing biuret groups of hexamethylene diisocyanate and diaminodicyclohexylmethane with an isocyanate content of 23.2% and a viscosity at 75 ° C. of 183 cP 24 parts of n-butyl acetate.
Die Auslaufzeit im Fordbecher 4 beträgt etwa 100 Sekunden, der Feststoffgehalt 99 %.The flow time in the Ford cup 4 is about 100 seconds, the solids content 99%.
Eigenschaften des Lackfilms nach halbstündigem Erhitzen bei 1500C: Pendelhärte: 111 Sekunden Erichsenwert: 10 Glanz: 86 Biegeprobe: in Ordnung fast kratzfest.Properties of the paint film after heating at 1500C for half an hour: Pendulum hardness: 111 seconds Erichsen value: 10 Gloss: 86 Bending test: OK, almost scratch resistant.
Beispiel 4 40 Teile Esterdiol 260 10 Teile Butandiol-1,4 137 Teile DESMODUR N, 75 %ig ergeben einen Klarlack mit einerViskosität von 80 Sekunden (DIN-Becher, 4 mm Düse). Der Lack ist in dieser Form gut spritzbar. Nach einer Einbrennzeit von 30 Sekunden bei 150°C erhält man einen hochelastischen Überzug mit folgenden Eigenschaften: Pendelhärte: 76 Sekunden Erichsenwert: 211 biegefest, fast kratzfest. Example 4 40 parts Esterdiol 260 10 parts 1.4-butanediol 137 parts DESMODUR N, 75% gives a clear lacquer with a viscosity of 80 seconds (DIN cup, 4 mm nozzle). The paint is easy to spray in this form. After a burn-in time of A highly elastic coating with the following properties is obtained for 30 seconds at 150 ° C: Pendulum hardness: 76 seconds. Erichsen value: 211 rigid, almost scratch-resistant.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500308 DE2500308A1 (en) | 1975-01-07 | 1975-01-07 | Low-viscosity sprayable cross-linkable coating compsns - contg. liquid ester diols, polyisocyanates, opt diluents or solvents binders and pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500308 DE2500308A1 (en) | 1975-01-07 | 1975-01-07 | Low-viscosity sprayable cross-linkable coating compsns - contg. liquid ester diols, polyisocyanates, opt diluents or solvents binders and pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2500308A1 true DE2500308A1 (en) | 1976-07-15 |
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ID=5936002
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752500308 Pending DE2500308A1 (en) | 1975-01-07 | 1975-01-07 | Low-viscosity sprayable cross-linkable coating compsns - contg. liquid ester diols, polyisocyanates, opt diluents or solvents binders and pigments |
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| Country | Link |
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| DE (1) | DE2500308A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996023016A1 (en) * | 1995-01-24 | 1996-08-01 | Eastern Michigan University | Water thinned polymeric vehicle for coating compositons with low amounts of volatile organic compounds |
| US5587428A (en) * | 1994-01-25 | 1996-12-24 | Eastern Michigan University | Polymeric vehicle effective for providing solventless coating compositions |
| US5641854A (en) * | 1994-01-25 | 1997-06-24 | Eastern Michigan University | Polymeric vehicle for high solids coatings |
| US5910563A (en) * | 1994-01-25 | 1999-06-08 | Exxon Chemical Patents, Inc. | Water thinned polymeric vehicle for coating compositions with low amounts of volatile organic compounds |
| US5955550A (en) * | 1994-01-25 | 1999-09-21 | Exxon Chemical Patents, Inc. | Polymeric vehicle for providing solventless coating compositions |
| US5969085A (en) * | 1994-01-25 | 1999-10-19 | Exxon Chemical Patents, Inc. | Polymeric vehicle for high solids coatings |
-
1975
- 1975-01-07 DE DE19752500308 patent/DE2500308A1/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5587428A (en) * | 1994-01-25 | 1996-12-24 | Eastern Michigan University | Polymeric vehicle effective for providing solventless coating compositions |
| US5610263A (en) * | 1994-01-25 | 1997-03-11 | Eastern Michigan University | Water thinned polymeric vehicle for coating compositions with low amounts of volatile oragnic compounds |
| US5641854A (en) * | 1994-01-25 | 1997-06-24 | Eastern Michigan University | Polymeric vehicle for high solids coatings |
| US5910563A (en) * | 1994-01-25 | 1999-06-08 | Exxon Chemical Patents, Inc. | Water thinned polymeric vehicle for coating compositions with low amounts of volatile organic compounds |
| US5955550A (en) * | 1994-01-25 | 1999-09-21 | Exxon Chemical Patents, Inc. | Polymeric vehicle for providing solventless coating compositions |
| US5969085A (en) * | 1994-01-25 | 1999-10-19 | Exxon Chemical Patents, Inc. | Polymeric vehicle for high solids coatings |
| WO1996023016A1 (en) * | 1995-01-24 | 1996-08-01 | Eastern Michigan University | Water thinned polymeric vehicle for coating compositons with low amounts of volatile organic compounds |
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