MXPA98009410A - Coating composition and method for reducing ultraviolet light degradation - Google Patents
Coating composition and method for reducing ultraviolet light degradationInfo
- Publication number
- MXPA98009410A MXPA98009410A MXPA/A/1998/009410A MX9809410A MXPA98009410A MX PA98009410 A MXPA98009410 A MX PA98009410A MX 9809410 A MX9809410 A MX 9809410A MX PA98009410 A MXPA98009410 A MX PA98009410A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- hydroxyl
- formula
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 41
- 230000015556 catabolic process Effects 0.000 title abstract description 7
- 230000004059 degradation Effects 0.000 title abstract description 7
- 238000006731 degradation reaction Methods 0.000 title abstract description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 245
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 27
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical compound C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 claims description 14
- 150000001565 benzotriazoles Chemical class 0.000 claims description 13
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000006096 absorbing agent Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- -1 methyl halogen Chemical class 0.000 claims description 12
- HTTGVORJOBRXRJ-UHFFFAOYSA-N OC1=CC=CC=C1C1=CC=NN=N1 Chemical class OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 10
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 10
- 125000004429 atoms Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- 239000004793 Polystyrene Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229920002223 polystyrene Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N N,N'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical class NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- 229920000180 Alkyd Polymers 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Chemical class 0.000 claims description 3
- 229920000570 polyether Chemical class 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N Benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 230000002745 absorbent Effects 0.000 claims 5
- 239000002250 absorbent Substances 0.000 claims 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims 3
- 239000004721 Polyphenylene oxide Chemical class 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 239000003822 epoxy resin Substances 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical class CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical class CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 2
- 229920000647 polyepoxide Polymers 0.000 claims 2
- YHCGGLXPGFJNCO-UHFFFAOYSA-N OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 Chemical compound OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 239000002952 polymeric resin Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 230000000996 additive Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004434 sulfur atoms Chemical group 0.000 description 2
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Abstract
The present invention relates to a coating composition containing a combination of ultraviolet light absorbing compounds, one or more of which is bound to a polymer, and a method for reducing degradation of coating compositions due to ultraviolet light exposure.
Description
COATING COMPOSITION AND METHOD TO REDUCE DEGRADATION BY ULTRAVIOLET LIGHT
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION The present invention describes a coating composition containing a combination of ultraviolet light absorbing compounds attached to polymers.
DESCRIPTION OF THE PRIOR ART Ultraviolet light absorbers are used in coating compositions to reduce the degradation of the coating resulting from the effects of atmospheric oxygen, moisture and ultraviolet light. The degradation manifests in fracture, loss of gloss, changes in shade, lamination and bubble formation in the cured or hardened coating films. It is known that stabilizers, such as ultraviolet (UV) absorbers substantially prevent or minimize such damage in coatings. Examples of ultraviolet light absorbers include benzotriazoles, 2-hydroxybenzophenones, oxanilide [sic], and 2-hydroxyphenyltriazines. Benzotriazoles are highly effective ultraviolet light absorbers over a broad spectrum, but these compounds are often not stable and may migrate to other coating layers in a multilayer coating system or may be chemically degraded in the coating composition, thus losing efficiency as an ultraviolet light absorber. The triazine compounds, ultraviolet light absorbers, are more chemically stable but do not have the range of ultraviolet light absorption that benzotriazoles have. An object of the present invention is to improve stability of the ultraviolet light absorbers in a coating composition to improve the absorption of ultraviolet light and to reduce the degradation of a coating composition due to ultraviolet light exposure.
SUMMARY OF THE INVENTION In accordance with the present invention, a benzotriazole bound to polymer or triazine bound to polymer is incorporated in a coating composition in combination with at least one other ultraviolet light absorber to improve the strength of the coating composition at the degradation by ultraviolet light. The benzotriazole bound to bound polymer or triazine prevents the migration of benzotriazole or triazine from the surface coating and increases its chemical stability in a coating composition, thereby providing greater protection to enduring ultraviolet light. The polymer-bonded benzotriazole and the polymer-bound triazine can be used in combination with one another, or any can be used in combination with other ultraviolet absorbers such as non-polymeric benzotriazoles, non-polymeric triazines, 2-hydroxybenzophenone, oxanilide and mixtures thereof. same. The benzotriazole and triazine can be added as separate polymers or can be polymerized on a simple polymeric compound. The benzotriazole or triazine can be polymerized on a polymeric component of the coating composition, either in a main resin, a pigmented resin powder, crosslinking agent, reoiogy modifier, flow modifying additives or other polymer components of the composite coatings. . In a preferred embodiment, the benzotriazole or benzotriazine is polymerized on the main crosslinkable resin.
DETAILED DESCRIPTION OF THE INVENTION Polymer bound triazine and polymer bound benzothiazole are incorporated into a coating composition combined together or used individually with one or more additional ultraviolet light absorbers, to provide more durable ultraviolet protection in a coating composition. . When a benzotriazole bound to polymers is used as a UV absorber. It is combined with compounds selected from the group consisting of triazines which may be polymeric or non-polymeric compounds, non-polymeric benzotriazoles, 2-hydroxybenzophenone compounds, oxanilides and mixtures thereof. When a triazine bound to a polymer is used it is combined with a benzotriazole bound to a polymer or not bound to polymer, the triazines not bound to polymer or other UV absorbers, such as 2-hydroxybenzophenone compounds, oxanilide, and mixtures thereof. same. The preferred combinations of U.V. include benzotriazole bound to polymer and triazine which can be polymer bound or non-polymer bound. A compound containing a benzotriazole bound to polymer useful for the present invention is shown in formula (la):
(the),
where, in the compounds of the formula (Ia), Ri, R2 and R3 can be hydrogen, but at least one of the radicals Ri and R2 must be different from hydrogen. Additionally R R2 and R3 can be halogen, hydroxy halogen methyl [sic], alkyl, having 1 to 18 carbons, phenyl alkyl having 1 to 4 carbon atoms in the alkyl, hydroxyalkyl moiety having 1 to 24 carbon atoms in the alkyl chain such as methyl, ethyl, propyl, butyl, hexyl, octyl, nonyl, dodecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl and eicosyl and also corresponding branched isomers, alkyl substituted by COOH, -COOY3, -CONH2, CONHY9, - CONYqY10, NH2, NHY9, -NY9Y10 -NHCOYn, -CN, and / or -OCOYu, having from 4 to 20 carbon atoms, is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy which have 1 to 12 carbon atoms, alkenyl having 3 to 6 carbon atoms, glycidyl, cyclohexyl, which is unsubstituted or substituted by hydroxyl, alkyl having 1 to 4 carbon atoms and / or -OCOYu, phenylalkyl having 1 to 5 carbon atoms in the alkyl fraction and is unsubstituted or substituted by hydroxyl, chlorine and / or methyl, -COY-; or --SO2Y -; ,, or if u is 2, Y; is alkylene having 2 to 16 carbon atoms, alkylene having 4 to 12 carbon atoms, xylylene, alkylene having 3 to 20 carbon atoms, is interrupted by 1 or more atoms -O- and / or substituted by hydroxyl, -CH-CH (OH) CH2-0-Y:;, -0CH; CH (OH) CH, -CO-Yi-CO, -CO-NH-Y; -NH-CO- O- (CH2) m- C02-Y18-OCO- (CH), in which m is 1, 2 or 3, and Y? is alkyl having 1 to 18 carbon atoms, amine, alkylamine or cycloalkylamine, wherein the alkyl or cycloalkyl has up to 6 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl having 3 to 20 carbon atoms, 'is interrupted by one or more oxygen or sulfur atoms or NT6- and / or is replaced by hydroxyl, alkyl having 1 to 4 carbon atoms and is substituted by -P (0) (0Yi4) 2 - Y9Y10 or -OCOYu and / or hydroxyl, alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y-, and Y-, 0 independent of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cyclohexyl having 5 to 12 carbon atoms, or Y? and Y-_; together they are alkylene, oxalkylene or azaalkylene having in each case 3 to 9 carbon atoms, Yn is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, Y 12 is alkyl having 1 to 18 carbon atoms. Alkenyl having 2 to 18 carbon atoms or, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms, or phenylamino, Y 3 is alkyl having 1 to 18 carbon atoms. carbon, phenyl or aliphenyl [sic] having 1 to 18 carbon atoms in the alkyl radical, Yi is alkyl having 1 to 12 carbon atoms or phenyl, Y15 is alkylene having 2 to 10 carbon atoms, phenylene or group-phenylene-M-phenylene-, in which M is -0-, -S-, -S02-, -CH- or -C (CH:.) 2- and Yie is alkylene, oxaalkylene or thiaalkylene having in each case 2 to 10 carbon atoms, phenylene or alkenylene having 2 to 6 carbon atoms, Yi7 is alkylene having 2 to 10 carbon atoms, phenylene or alkylphenlene [sic] having 1 to 11 carbon atoms, alkyl fraction, and Y? 8 is alkylene having 2 to 10 carbon atoms or alkylene having 4 to 20 carbon atoms and one or several times for oxygen. Ri can be phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, for example benzyl, and can also be cycloalkyl having 5 to 8 carbon atoms, for example, cyclopentyl, cyclohexeyl and cyclooctyl, or a radical of the formula
R4 I
wherein R4 and R5 independent from each other are alkyl having in each case 1 to 5 carbon atoms, in particular methyl or R4 together with the radical CnH2n +? -m, form a cycloalkyl radical having 5 to 12 carbon atoms, for example, cyclohexyl, cyclooctyl and cyclodecyl. M is a radical of the formula -COOR ,, in which R ,. is hydrogen, or alkyl having 1 to 12 carbon atoms, or alkoxyalkyl having 1 to 20 carbon atoms in each of the alkyl and alkoxy moieties. Suitable R6 alkyl radicals are those mentioned for Ri. Examples of suitable alkoxyalkyl groups are: C2H4OC2H5, -C2H4OC8H17 and -C4H8OC4H9. As phenylalkyl having 1 to 4 carbon atoms, R6 is, for example, benzyl, cumyl, a-methylbenzyl or phenylbutyl. At least one of the radicals R-x and R may be different from hydrogen. Alternatively, a benzotriazole useful in the present invention has the following formula:
In the compounds of the formula (Ib) T is hydrogen or alkyl having 1 to 6 carbon atoms, such as methyl and butyl, Ti is hydrogen, chloro or alkyl or alkoxy having in each case 1 to 4 carbon atoms, for example, methyl, methoxy and butoxy, and n is 1 or 2. If n is 1, T; is chlorine or a radical of the formula OT3 or
N and if n is 2, T is a radical of the formula
- Tlß -N -
Lß.
or, -0-T9-0-, where T3 is hydrogen, alkyl having 1 to 18 carbon atoms and is unsubstituted or substituted by one to three hydroxyl groups or by -OCOT, alkyl having 3 to 18 atoms of carbon, is interrupted once or several times by -O- or NT6 and is substituted not substituted by hydroxyl or -OCOT6. Examples of T 3 as cycloalkyl include cycloalkyl having 5 to 12 carbon atoms, such as cyclopentyl, cyclohexyl or cyclooctyl and is unsubstituted or substituted by hydroxyl and / or alkyl having 1 to 4 carbon atoms in the alkyl moiety, for example , benzyl or phenyl butyl. T5 can also be alkenyl having 2 to 18 carbon atoms. Suitable alkenyl radicals are derivatives of the alkyl radicals listed in the definitions of Ra. These alkenyl radicals can be substituted by hydroxyl. Examples of T3 such as phenylalkyl such as phenylethyl, cumyl, a-methylbenzyl or benzyl .. T3 can also be a radical of the formula -CH2C-H (0H) -T7 or
-CH2éH NCH2
T.? and T5 independently of one another are hydrogen, alkyl having 1 to 18 carbon atoms, alkyl which has 3 to 18 carbon atoms, and is interrupted one or more times by -O- or NTV-, cycloalkyl having 5 to 12 carbon atoms, for example, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenylalkyl having 1 to 4 carbon atoms, in the alkyl or hydroxyalkyl having 2 to 4 carbon atoms, T is hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, Ti is hydrogen, alkyl having 1 to 18 carbon atoms, phenyl substituted or unsubstituted by hydroxyl, phenylalkyl which has 1 to 4 carbon atoms in the alkyl moiety, or CH2OT9, T1 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 8 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl. The 2-hydroxyphenyltriazine has the formula:
In the compounds of the formula (II), u is 1 to 2 and r is an integer of 1 to 3, the Yi independently substituted one of the other are hydrogen, hydroxyl halogen methyl [sic], alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 19 carbon atoms, phenoxy which is unsubstituted or substituted by hydroxyl, alkoxy having 1 to 18 carbon atoms, or halogen or is substituted by alkyl or alkoxy having in each case 1 to 18 carbon atoms or halogen, alkyl having 1 to 12 carbon atoms and is substituted by COOH, COOY, -CONH2, CONHY3, -CONY3Y10, NH2, NHY9, -NY9Y10 -NHCOY ?: , -CN, and / or -OCOYn, having from 4 to 20 carbon atoms, is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxy or alkoxy having 1 to 12 carbon atoms, alkenyl which has from 3 to 6 carbon atoms, glycidyl, cyclohexyl which is unsubstituted or substituted by hydroxyl, alkyl having 1 to 4 carbon atoms and / or -OCOYn, phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety and is substituted or not substituted by hydroxyl, chlorine and / or methyl, -COY 12 or -SO2Y13, or if u is 2, Y2 is alkylene having 2 to 16 carbon atoms, alkylene having 4 to 12 carbon atoms, xylene, alkylene having 3 to 20 carbon atoms, is interrupted by 1. or more atoms -0- and / or substituted by hydroxyl. -CH2CH, (OH) CH2-0-Yij, -OCH2CH (OH) CH2, -CO-Yif-CO, -CO-NH-Y17-NH-CO-, O- (CH2) p.-C02-Yi3- OCO- (CH2) n, in which it is 1, 2 or 3, and Y is alkyl having 1 to 18 carbon atoms, amine, alkylamine or cycloalkylamine, wherein the alkyl or cycloalkyl group has up to 6 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl having 3 to 20 carbon atoms, is interrupted by one or more oxygen or sulfur atoms or -NT6- and / or is replaced by hydroxyl, alkyl having 1 to 4 atoms of carbon and is substituted by -P (O) (OY? 4) 2, -NY9Y-; or -OCOYi. and / or hydroxyl, alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y9 and Y10 independent of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cyclohexyl having 5 to 12 carbon atoms, or Y9 and Yio together are alkylene, oxalkylene azaalkylene having in each case 3 to 9 atoms, and;: is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, YX2 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms, or phenylamino, Y 3 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the radica alkyl, Y is alkyl having 1 to 12 carbon atoms or phenyl, Yis is alkylene having 2 to 10 carbon atoms, phenylene or a group -phenylene-M-phenylene-, wherein M is -O- -S-, -S02-, -CH2- or -C (CH3) 2- and Y16 is alkylene, oxalkylene or thiaalkylene having in each case 2 to 10 carbon atoms, phenylene or alkenylene having 2 to 6 carbon atoms , Y- is alkylene having 2 to 10 carbon atoms, phenylene and alkylphenylene having 1 to 11 carbon atoms in the alkyl moiety, and Y-3 is alkylene having 2 to 10 carbon atoms or alkylene having 4 up to 20 carbon atoms and is interrupted once or several times by oxygen. -
The 2-h droxybenzophenone has the formula:
In the formula, v is an integer from 1 to 3 and w is 1 or 2 and the substituents Z independently of one another are hydrogen, alkyl, alkoxy or alkylthio having in each case 1 to 22 carbon atoms, phenoxy or phenylthio . The ultraviolet light-absorbing compounds bound to polymer are reacted on the polymers by addition polymerization, condensation or rearrangement or grafting reactions. The AUV compounds can react with the same separated polymers or polymers. Examples of polymers in which these can be incorporated are: polyolefins, polyacrylates, polymethacrylates, polystyrene, polystyrenes derivatives, polyurethanes, epoxy, polyesters, polyethers, alkyd [sic] and carbamate polymers and mixtures thereof. The polymer-bound benzotriazole is effective to absorb UV light in the range of about 200 nm to about 400 nm, particularly in the range of 240 nm to 420 nn. In the preferred embodiment, the benzotriazole is polymerized on the main resin or crosslinker used in the coating composition. As an alternative, the benzotriazole is polymerized on a powdered pigment resin or other compound used in the coating composition. The ultraviolet light absorber bonded to the polymer is incorporated in the coating composition in an amount between 0.1 and 30.0% by weight, preferably between 1.0 and 10.0% by weight, based on the total weight of the coating composition. The invention is illustrated by the following non-limiting examples.
Examples
Example 1 Benzotriazole bound to acrylic polymer United polymer absorbing ultraviolet light. An ultraviolet light absorber bonded to polymer containing 2.0% benzotriazole, based on the total solids of the coating was prepared by polymerization of 28.4 grams of benzotriazole, marketed under the trademark Norbloc® 7966, available from Noramco, Inc. on 1514.3 grams of a hydroxyl-functional carbamate resin under the Ureclear® trademark, commercially available from BASF Corporation. The carbamate resin with functional hydroxyl had a hydroxyl equivalency of 1650 g / equivalent at 95% non-volatile content.
Example 2: Coating composition containing benzotriazole attached to a polymer
Ingredient Quantity * Acrylic resin of Example 1 75.51 2 Resi ine 747 Aminoplast 20.66 Acid catalyst 1.00 Fuming silica additive for control of 1.31 rheology Additive for fluid control 0.20 Adhesion promoter 1.32 Total 100.00 * All weights are in weight percent in based on the total solids content of the coating.
Example 3 Coating composition containing a mixture of benzotriazole and triazine bound to polymer To the coating composition of Example 2 were added 2.1 grams of 2-hydroxyphenyltriazine. Triazine was used in a 72% triazine and solvent solution. The composition of the resulting coating contains 1% by weight based on the solids content in the coating composition.
EXAMPLE 4 Coating composition containing benzotriazole bound to polymer, triazine and hindered amine light stabilizer (HALS) To the coating composition of example 2 was added 2-hydroxyphenyltriazine in an amount of 2.1 grams and a hindered amine light stabilizer (HALS) sold under the trademark Sandivar 3058 and available by Sandoz, in an amount of 1.5% based on the total solids content in the coating composition. HALLS [sic] is used in a 95% solution, where the solution contains HALS and solvent.
Claims (19)
1. A coating composition comprising: a) a main crosslinkable resin and b) a combination of ultraviolet light absorbing compounds, wherein at least one ultraviolet light absorber is an ultraviolet light absorber attached to a polymer selected from the group consisting of benzotriazoles attached to polymer that have the formula. (the), and
2-hydroxyphenyltraizines bound to polymer having the formula (II) And mixtures thereof, Used in combination with ultraviolet light absorbers not bound to a polymer selected from the group consisting of non-polymeric 2-hydroxyphenyltriazines, non-polymeric benzotriazoles, 2-hydroxyphenones, oxanilide and mixtures thereof. wherein the compounds of the formula (la), R: is selected from the group consisting of hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and R 2 is selected of the group consisting of hydrogen, halogen, alkyl having 1 to 18 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, R < it is selected from the group consisting of hydrogen, chloro, having 1 to 4 carbon atoms; with at least one of the radicals Ri and R2 being different from hydrogen; in the formula (Ib) T is hydrogen or alkyl having 1 to 6 carbon atoms, T is hydrogen, chloro or alkyl having 1 to 4 carbon atoms, and n is 1 or 2, when n equals 1, T2 is chlorine or a radical of the formula -OT3, where T3 is hydrogen, alkyl having 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups; alkenyl having from 2 to 18 carbon atoms and is unsubstituted or substituted after hydrixyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula CH: CH (OH) -T- or glycidyl; where T- is hydrogen, or alkyl having 1 to 18, phenyl which is unsubstituted or substituted by hydroxyl; and if n is 2, T2 is a radical of the formula -0-T9-0-, T ^ is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene having 2. up to 18 carbon atoms and this, interrupted once or several times by -O-, in the formula (bundle) u is 1 to 2, r is an integer from 1 to 3, the substituents Yi independently of one another are hydrogen, hydroxyl, halogen, methyl halogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms, when u is one, Y 2 is alkyl having 1 to 18 carbon atoms, alkyl having 1 to 12 carbon atoms and is substituted by COOH, -COOY8, -CONH2, CONHYg, -ONY3Y? 0, -CN, -OCOYn, or mixtures thereof; alkyl having 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms; alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety and unsubstituted or substituted by hydroxyl, chloro and or methyl; -COY- or SO2Y3, wherein it is alkyl having 1 to 18 carbon atoms, amine, alkylamine or cycloalkylamine wherein the alkyl or cycloalkyl group have up to 6 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl which it has 3 to 20 carbon atoms and is interrupted by one or more oxygen atoms, or said alkyl substituted by substituted [sic] by hydroxyl; alkenyl having 3 to 18 carbon atoms, glycidyl or phenyl alkyl having 1 to 5 carbon atoms in the alkyl moiety, Y9 and Y10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 atoms, carbon or cyclohexyl having 5 to 12 carbon atoms, Y ?? is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, Y 2 is alkyl having 1 to 18 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, YL3 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical; and when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkylene having 4 to 12 carbon atoms and is interrupted by one or more atoms -O- and / or is substituted by hydroxyl; -CH2CH (OH) CH2 -O- Y? 5-OCH2CH (OH) CH2, OR- (CH2) m-C02-Y? 8-OCO- (CH2) m, in which m is 1, 2 or 3, and Yi? is alkylene having 2 to 10 carbon atoms, phenylene or a group -phenylene-M-phenylene- in which M is -O- -S-, -S02-, - CH2- or -C (CH3) 2-, Y :; it is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen. 2. The coating composition according to claim * 1 wherein the combination of ultraviolet absorbent compounds further comprises a polymeric benzothiazole in combination with polymer-bound 2-hydroxyphenyl triazines.
3. The coating composition according to claim 2, wherein the combination of ultraviolet absorbent compounds further comprises compounds selected from the group consisting of non-polymeric 2-hydroxyphenyl triazines, non-polymeric benzotriazoles, non-polymeric oxaniline, non-polymeric 2-hydroxybenzophenones and mixtures of the same.
4. The coating composition according to claim 1, wherein the combination of ultraviolet absorbent compounds further comprises a polymeric light absorbing compound having the formula: where v is an integer from 1 to 3 and w is l or 2 and substituents Z independently of one another are hydrogen, halogen, hydroxy or alkoxy having from 1 to 12 carbon atoms.
5. The coating composition according to claim 1 wherein the ultraviolet light absorbing compounds are polymerized onto components of the coating composition, selected from the group consisting of a main resin, a crosslinker and mixtures thereof.
6. The coating composition according to claim 1 wherein the main polymer resin is selected from the group consisting of acrylate, methacrylate, urethane, carbamate, polyester, polyether, polystyrene, polystyrene derivatives, polyolefins, alkyd [sic], and polymeric epoxy resins and mixtures thereof.
7. The coating composition according to claim 1 further comprises a cross-linker selected from the group consisting of isocyanates, ureas, aminoplasts, carbamates and mixtures thereof.
8. The coating composition according to claim 1 or 2, wherein the 2-hydroxyphenylbenzotriazole or triazine is copolymerized with a main acrylate resin having functional hydroxyl and the coating composition includes an aminoplast crosslinker.
9. The coating composition according to claim 1 wherein the coating is a clear coating composition. A method for improving the ultraviolet radiation absorption of a coating composition, which consists in the step of: adding to a coating composition, a combination of ultraviolet light absorbing compounds, wherein at least one ultraviolet light absorber is bonded a polymer is selected from the group consisting of benzotriazoles attached to polymer having the formula: (la), Y the 2-hydroxyphenyltraizines bound to polymer having formula (lia). and mixtures thereof, used in combination with a non-polymer bound ultraviolet light absorber selected from the group consisting of benzotriazoles, 2-hydroxyphenyl triazines, 2-hydroxybenzophenones, oxanilide and mixtures thereof, wherein in the compounds of formula (la): Ri is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, R 2 is H, halogen or alkyl having 1 to 18 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl portion, R3 is H, chloro, alkyl or alkoxy having in each case 1 up 4 carbon atoms, in formula (Ib) T is hydrogen or alkyl having 1 to 6 carbon atoms, Ti is hydrogen, chloro or alkyl having 1 to 4 carbon atoms, and n is 1 or 2, when n is 1, T2 is chloro or a radical of the formula -OT, where T3 is hydrogen, alkyl having 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups; alkyl having 3 to 18 carbon atoms interrupted once or several times by -0- and unsubstituted or substituted by hydroxyl; alkenyl that has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula -CH 2 CH (OH) -T 7 or glycidyl; where T7 is hydrogen, alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl; and if n is 2, T2 is a radical of the formula -O-Tg-0-, T9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene having 2 to 18 carbon atoms and is interrupted once or several times by -0-, in the formula (bundle) u is 1 to 2, r is an integer from 1 to 3, the substituents Y-- independent of one another are hydrogen, hydroxyl, halogen, methyl halogen, alkyl having L up to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms, when u is 1, Y 2 is alkyl having 1 to 18 carbon atoms, alkyl having 1 to 12 carbon atoms and is substituted by -COOH -C00Y8, -C0NH2, CONHYg, -ONY = .Y10, -CN, -OCOYu, or mixtures thereof; alkyl having 4 to 20 carbon atoms and is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having from 1 to 12 carbon atoms; alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety and unsubstituted or substituted by hydroxyl, chloro and / or methyl; where Y8 is alkyl having 1 to 18 carbon atoms, amine, alkylamine or cycloalkylamine wherein the alkyl or cycloalkyl portion has up to 6 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl having 3 to 20 carbon atoms, carbon and is interrupted by one or more oxygen atoms, or said alkyl substituted by [sic] hydroxyl; alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y9 and Y10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cyclohexyl having 5 to 12 carbon atoms, Yn is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, Y 12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, Y 3 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical; and when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkylene having 4 to 12 carbon atoms and is interrupted by one or more atoms -0- and / or is substituted by hydroxyl; -CH2CH (OH) CH2-0-Y? S -OCH2CH (OH) CH2, or - (CH2) m-C02-Y? E-0C0- (CH2) Mra? ~, In which m is 1, 2 or 3, Yis is alkylene having 2 to 10 carbon atoms, phenylene or a group -phenylene-M-phenylene- in which M is -0-, -S-, -S02-, -CH2- or -C (CH3 2-, and Yis is alkylene having 2 to 10 carbon atoms or alkylene having 4 to 20 carbon atoms and is interrupted once or several times by oxygen. 11. A method for improving the ultraviolet radiation absorption of the transparent layer of one color plus the transparent composite coating comprising the addition step to the transparent layer, a combination of ultraviolet light absorbing compounds, wherein at least one light absorber Ultraviolet is an ultraviolet light absorber attached to polymer selected from the group consisting of benzotriazoles attached to polymer having the formula (la), 2-hydroxyphenyltraizine bound to polymer having the formula (Ha). and mixtures thereof, used in combination with a non-polymer bound ultraviolet light absorber selected from the group consisting of benzotriazoles, 2-hydroxyphenyltriazine, 2-hydroxybenzophenones, oxanilides, and mixtures thereof, wherein in formula (Ia) Ri is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the fraction alkyl, R 2 is H, halogen, or alkyl having 1 to 18 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl fraction R 3 is H, chloro, alkyl or alkoxy, which in each case has 1 to 4 carbon atoms, in formula (Ib) T is hydrogen or alkyl having 1 to 6 carbon atoms, Ti is hydrogen, chloro or alkyl having 1 to 4 carbon atoms, and n is 1 or 2, when n is 1, T? is chlorine or a radical of the formula -0T ~., where T3 is hydrogen, alkyl having 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups; alkyl having 3 to 18 carbon atoms interrupted one or more times by -O- and substituted or unsubstituted by hydroxyl; alkenyl having 2 to 18 carbon atoms and substituted or unsubstituted by hydroxyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula CH 2 CH (OH) -T 7 or glycidyl; where T7 is hydrogen, alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl; and if n is 2, T2 is a radical of the formula -O-T? -0-, T9 is alkylene having 2 to 8 carbon atoms, alkenylene which. has 4 to 8 carbon atoms, cyclohexylene, alkylene having 2 to 18 carbon atoms and is interrupted once or several times by -0-; in the formula Ha u is 1 to 2 r is an integer from 1 to 3, the substituents Y i independent of one another are hydrogen, hydroxyl, halogen, halogen methyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 up to 18 carbon atoms, when u is 1, Y2 is alkyl having 1 to 18 carbon atoms, alkyl having 1 to 12 carbon atoms and is substituted by -COOH -COOY8, -CONH;, CONHY-, -ONY -.Yi, -CN, -OCOY:?, Or mixtures thereof; alkyl having 4 to 20 carbon atoms and is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having from 1 to 12 carbon atoms; alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety and unsubstituted or substituted by hydroxyl, chloro and / or methyl; where Y8 is alkyl having 1 to 18 carbon atoms, amine, alkylamine or cycloalkylamine wherein the alkyl or cycloalkyl portion has up to 6 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl having 3 to 20 carbon atoms, carbon and is interrupted by one or more oxygen atoms, or said alkyl substituted by [sic] hydroxyl; alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y9 and Y: 0 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cyclohexyl having 5 to 12 carbon atoms, Yu is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl , Y12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, Y3 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical; and when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkylene having 4 to 12 carbon atoms and is interrupted by one or more atoms -O- and / or is substituted by hydroxyl; -CH2CH (OH) CH -0-Y? S -OCH2CH (OH) CH2, or - (CH2) m-C02-Y? 8-OCO- (CH2) m? Rai- / in which m is 1, 2 or 3, Y15 is alkylene having 2 to 10 carbon atoms, phenylene or a group -phenylene-M-phenylene- in which M is -0-, -S-, -SO2-, -CH2- or -C ( CH3) 2-, and Yis is alkylene having 2 to 10 carbon atoms or alkylene having 4 to 20 carbon atoms and is interrupted once or several times by oxygen 12. The method according to claim 10 or 11 wherein the combination of Ultraviolet absorbent compounds contain a polymeric benzotriazole encompassing polymer bound 2-hydroxyphenyl triazines. The method according to claim 12 wherein the combination of ultraviolet absorbent compounds further contain compounds selected from the group consisting of non-polymeric 2-hydroxyphenyl triazine, non-polymeric benzotriazoles, non-polymeric oxaniline, non-polymeric 2-hydroxybenzophenones and mixtures thereof . The method according to claim 10 or 11 wherein the combination of ultraviolet light absorbing compounds further contains a polymeric light absorbing compound having the formula: wherein v is integer from 1 to 3 and w is 1 or 2 and substituents Z independently of one another are hydrogen, halogen, hydroxy or alkoxy having 1 to 12 carbon atoms. The method according to claim 10 or 11 wherein the ultraviolet light absorbing compounds are polymerized onto a component of the coating composition, selected from the group consisting of a master resin, crosslinker and mixtures thereof. 16. The method according to claims 10 or 11 wherein the benzotriazole is polymerized on a main resin selected from the group consisting of acrylate, methacrylate, urethane, carbamate, polyester, polyether, polystyrene, polystyrene derivatives, polyolefins, alkyd [sic] and polymeric epoxy resins and mixtures thereof. 17. The method according to claim 11 wherein the benzotriazole is polymerized on a main resin containing an acrylate resin with a hydroxyl function. 18. The method according to claim 10 or 11 further contains a cross-linker selected from the group consisting of isocyanates, ureas, aminoplasts, carbamates and mixtures thereof. 19. The method according to claim 16 wherein the coating mixture is crosslinked with an aminoplast cross-linking resin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08768829 | 1996-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA98009410A true MXPA98009410A (en) | 1999-04-06 |
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