DE4010444A1 - USE OF NECK CONNECTIONS IN VARNISHES - Google Patents
USE OF NECK CONNECTIONS IN VARNISHESInfo
- Publication number
- DE4010444A1 DE4010444A1 DE4010444A DE4010444A DE4010444A1 DE 4010444 A1 DE4010444 A1 DE 4010444A1 DE 4010444 A DE4010444 A DE 4010444A DE 4010444 A DE4010444 A DE 4010444A DE 4010444 A1 DE4010444 A1 DE 4010444A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- formula
- compound
- resin
- 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.)
- Withdrawn
Links
- 239000002966 varnish Substances 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 18
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 17
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 16
- 239000004922 lacquer Substances 0.000 claims abstract description 15
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 9
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Chemical group 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims description 16
- 229920005749 polyurethane resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 9
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 238000000643 oven drying Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 230000003019 stabilising effect Effects 0.000 abstract 1
- 239000003973 paint Substances 0.000 description 19
- 239000010410 layer Substances 0.000 description 11
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- -1 aromatic isocyanates Chemical class 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 4
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CEAWIMABVSITMV-YEJXKQKISA-N Desmodin Chemical compound CC1(C=CC2=C(C3=C(C=C2O1)OC[C@@H]4[C@H]3OC5=CC(=C(C=C45)OC)O)OC)C CEAWIMABVSITMV-YEJXKQKISA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WQDBUDHEWXLHSA-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-3-methylphenol Chemical compound C=1C=C(O)C(C(C)(C)C)=C(C)C=1C(CCC)C1=CC=C(O)C(C(C)(C)C)=C1C WQDBUDHEWXLHSA-UHFFFAOYSA-N 0.000 description 1
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
- LZMVPEUISJTHGP-UHFFFAOYSA-N 4-[3,3-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-2-tert-butyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1CCC(C)(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C LZMVPEUISJTHGP-UHFFFAOYSA-N 0.000 description 1
- OJJXZHYAPVFDRX-UHFFFAOYSA-N 6-tert-butyl-3-[[5-[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-3H-dithiol-3-yl]methyl]-2,4-dimethylphenol terephthalic acid Chemical compound C(C1=CC=C(C(=O)O)C=C1)(=O)O.C(C)(C)(C)C1=C(C(=C(CC2=CC(SS2)CC2=C(C(=C(C=C2C)C(C)(C)C)O)C)C(=C1)C)C)O OJJXZHYAPVFDRX-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 240000009125 Myrtillocactus geometrizans Species 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SAMOITCGMRRXJU-UHFFFAOYSA-N [3-(2-hydroxybenzoyl)phenyl]-(2-hydroxyphenyl)methanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC(C(=O)C=2C(=CC=CC=2)O)=C1 SAMOITCGMRRXJU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000005001 aminoaryl group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- KXZXLEYRSHQNCR-UHFFFAOYSA-N methane 2-methylidenenonanethioic S-acid Chemical compound C.CCCCCCCC(=C)C(O)=S.CCCCCCCC(=C)C(O)=S.CCCCCCCC(=C)C(O)=S.CCCCCCCC(=C)C(O)=S KXZXLEYRSHQNCR-UHFFFAOYSA-N 0.000 description 1
- AOGLBNCAHFLQDZ-UHFFFAOYSA-N methane 2-methylidenepentadecanethioic S-acid Chemical compound C.CCCCCCCCCCCCCC(=C)C(O)=S.CCCCCCCCCCCCCC(=C)C(O)=S.CCCCCCCCCCCCCC(=C)C(O)=S.CCCCCCCCCCCCCC(=C)C(O)=S AOGLBNCAHFLQDZ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000005623 oxindoles Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
Abstract
Description
Die Erfindung betrifft gehinderte Amin-Lichtstabilisatoren (HALS) zur Verwendung beim Stabilisieren von wärmehärtbaren Acryllacken (TSA), Alkyd-Melamin-Lacken (A/MF), 2-Komponenten-Polyurethan-Lacken (2C-PUR) und thermoplastischen Acryl-(TPA)-Lacken.The invention relates to hindered amine light stabilizers (HALS) for use in stabilizing thermosetting acrylic paints (TSA), Alkyd melamine paints (A / MF), 2-component polyurethane paints (2C-PUR) and thermoplastic acrylic (TPA) lacquers.
Gemäß der Erfindung wird ein Lack geschaffen, enthaltend ein wärmehärtbares Acrylharz, ein Alkyd-Melamin-Formaldehydharz, ein 2-Komponenten- Polyurethanharz (oder Harze, die ein 2-Komponenten-Polyurethanharz bilden) oder ein thermoplastisches Acrylharz und eine U.V.-stabilisierende Menge einer Verbindung der Formel IAccording to the invention, a lacquer is created containing a thermosetting Acrylic resin, an alkyd-melamine-formaldehyde resin, a 2-component Polyurethane resin (or resins that form a 2-component polyurethane resin) or a thermoplastic acrylic resin and a UV stabilizing amount a compound of formula I.
worin jedes R₁ unabhängig voneinander -CH₃ oder -CH₂(C1-4-Alkyl) ist
oder beide Gruppen R₁ eine Gruppe -(CH₂)₅- bilden;
jedes R₂ unabhängig voneinander -CH₃ oder -CH₂(C1-4-Alkyl) ist oder
beide Gruppen R₂ eine Gruppe -(CH₂)₅- bilden;
R Wasserstoff, Sauerstoff, C1-8-Alkyl oder -COR₅ ist;
wobei R₅ -C(R₁₃)=CH₂, C1-6-Alkyl, Phenyl, -NR₇R₈, -CO-C₆H₅,
-CH₂-C₆H₅, -COOC1-12-Alkyl oder -COOH ist; R₇ Wasserstoff, C1-12-Alkyl,
C5-6-Cycloalkyl, Phenyl, Phenyl-C1-4-alkyl oder C1-12-Alkylphenyl ist und
R₈ Wasserstoff oder C1-12-Alkyl ist; und R₁₃ die unten angegebene
Bedeutung hat;
R₄ -NR₁₃R₁₄ ist oder eine Gruppe der Formel α wherein each R₁ is independently -CH₃ or -CH₂ (C 1-4 alkyl) or both groups R₁ form a group - (CH₂) ₅-;
each R₂ is independently -CH₃ or -CH₂ (C 1-4 alkyl) or both groups R₂ form a group - (CH₂) ₅-;
R is hydrogen, oxygen, C 1-8 alkyl or -COR₅;
wherein R₅ is -C (R₁₃) = CH₂, C 1-6 alkyl, phenyl, -NR₇R₈, -CO-C₆H₅, -CH₂-C₆H₅, -COOC 1-12 alkyl or -COOH; R₇ is hydrogen, C 1-12 alkyl, C 5-6 cycloalkyl, phenyl, phenyl-C 1-4 alkyl or C 1-12 alkylphenyl and R₈ is hydrogen or C 1-12 alkyl; and R₁₃ has the meaning given below; R₄ is -NR₁₃R₁₄ or a group of the formula α
worin R₁₃ Wasserstoff oder unsubstituiertes oder durch OH monosubstituiertes
C1-6-Alkyl ist;
R₁₄ Wasserstoff oder unsubstituiertes oder durch OH monosubstituiertes
C1-6-Alkyl ist; und
X C1-12-Alkylen ist.wherein R₁₃ is hydrogen or C 1-6 alkyl unsubstituted or monosubstituted by OH;
R₁₄ is hydrogen or unsubstituted or C 1-6 alkyl monosubstituted by OH; and
XC is 1-12 alkylene.
In dieser Beschreibung wird ein ein wärmehärtbares Acrylharz enthaltender Lack als TSA-Lack, ein ein Alkyd-Melamin-Formaldehydharz enthaltender Lack als A/MF-Lack, ein Lack, der ein 2-Komponenten-Polyurethanharz oder Harze, die ein 2-Komponenten-Polyurethanharz bilden, enthalten, als 2C-PUR-Lack und ein ein thermoplastisches Acrylharz enthaltender Lack als TPA-Lack bezeichnet.In this specification, a thermosetting acrylic resin is used Lacquer as TSA lacquer, an alkyd-melamine-formaldehyde resin containing Paint as an A / MF paint, a paint that is a 2-component polyurethane resin or resins that form a 2-component polyurethane resin, as 2C-PUR lacquer and a lacquer containing a thermoplastic acrylic resin as Designated TPA lacquer.
Falls in dieser Beschreibung auf ein Polyurethanharz Bezug genommen wird, umfaßt dies Harze, die ein Polyurethanharz bilden.If reference is made to a polyurethane resin in this description this includes resins that form a polyurethane resin.
Vorzugsweise sind R₁₃ und R₁₄ unabhängig voneinander Wasserstoff oder C1-4-Alkyl.Preferably R₁₃ and R₁₄ are independently hydrogen or C 1-4 alkyl.
Bevorzugte Verbindungen der Formel I sind solche der Formeln II bisPreferred compounds of the formula I are those of the formulas II to
worin R′ Wasserstoff, -CH₃ oder -COCH₃ ist und R₁₆ C1-6-Alkyl (vorzugsweise n-C₄H₉) ist.wherein R 'is hydrogen, -CH₃ or -COCH₃ and R₁₆ C 1-6 alkyl (preferably n-C₄H₉).
In den Formeln II bis IV ist R′ vorzugsweise Wasserstoff.In the formulas II to IV, R 'is preferably hydrogen.
Gemäß der Erfindung wird außerdem ein ofentrocknender TSA-Lack geschaffen, der ein wärmehärtbares Acrylharz und ein U. V. stabilisierende Menge einer Verbindung einer der oben definierten Formeln II bis IV enthält.According to the invention, an oven drying TSA varnish is also used created a stabilizing acrylic resin and a UV stabilizing Contains amount of a compound of one of the formulas II to IV defined above.
Gemäß der Erfindung wird außerdem noch ein Überzug geschaffen, der von einem Lack abgeleitet ist, der ein wärmehärtbares Acrylharz, ein Alkyd-Melamin-Formaldehydharz, ein 2-Komponenten-Polyurethanharz oder Harze, die ein 2-Komponenten-Polyurethanharz bilden, oder ein thermoplastisches Acrylharz und eine U. V.-stabilisierende Menge einer Verbindung der oben definierten Formel I enthält.According to the invention, a coating is also created which is derived from a paint that is a thermosetting acrylic resin Alkyd-melamine-formaldehyde resin, a 2-component polyurethane resin or Resins that form a 2-component polyurethane resin or a thermoplastic Acrylic resin and a UV stabilizing amount of a compound contains the formula I defined above.
Mit Vorteil ist ein Überzug gemäß der Erfindung nicht säuregehärtet, obwohl er säuregehärtet sein kann.Advantageously, a coating according to the invention is not acid-hardened, although it can be acid hardened.
Wämrehärtbare Acrylharze, die in einem TSA-Lack benützt werden können, sind solche, die von Melamin-Formaldehyd-Polyacrylat-Lacken abgeleitet sind, noch besser solche, die von einem Hydroxy-Gruppen enthaltenden Polyacrylatharz und Melamin-Formaldehyd abgeleitet sind.Heat-curable acrylic resins that can be used in a TSA varnish are those of melamine formaldehyde polyacrylate paints are derived, even better, those derived from a hydroxy group containing polyacrylate resin and melamine formaldehyde are derived.
Alkyd-Melamin-Formaldehyd-(A/MF)-Harze (vorzugsweise 30 : 70 Melamin/Formaldehyd (1 : 1) zu Alkyd), die in einem A/MF-Lack gemäß der Erfindung verwendet werden können, werden aus solchen ausgewählt, die von ölmodifizierten Polyesterharzen (Öl-Alkydharze) und Melaminharzen abgeleitet sind; vernetzte Polyacrylat- und Melaminharze; gesättigte Polyester- und Melaminharze oder selbstvernetzende Polyacrylatharze.Alkyd melamine formaldehyde (A / MF) resins (preferably 30:70 Melamine / formaldehyde (1: 1 to alkyd), which is in an A / MF varnish according to the Invention can be used are selected from those of derived from oil-modified polyester resins (oil-alkyd resins) and melamine resins are; cross-linked polyacrylate and melamine resins; saturated polyester and melamine resins or self-crosslinking polyacrylate resins.
Polyurethanharze, die in 2C-PUR-Lacken verwendet werden können, werden ausgewählt aus Hydroxy-Gruppen-enthaltenden Polyester- und/oder Polyacrylatharzen, gehärtet mit aliphatischen oder aromatischen Isocyanaten.Polyurethane resins that can be used in 2C-PUR lacquers selected from hydroxy group-containing polyester and / or polyacrylate resins, hardened with aliphatic or aromatic isocyanates.
Thermoplastische Acrylharze, die in TPA-Lacken verwendet werden können, werden ausgewählt aus thermoplastischen Acrylatharzen.Thermoplastic acrylic resins that can be used in TPA paints are selected from thermoplastic acrylic resins.
Die Lacke gemäß der Erfindung können verwendet werden, um metallische Ein- oder Zweischicht-Überzüge oder Uni-, Ein- oder Zweischichtüberzüge herzustellen. Vorzugsweise werden TSA- und 2C-PUR-Lacke verwendet, um Zweischicht-Überzüge herzustellen, und Melamin-Alkydharze und Acryl-Melaminharze werden vorzugsweise verwendet, um Einschicht-Überzüge herzustellen.The paints according to the invention can be used to metallic One- or two-layer coatings or plain, one- or two-layer coatings to manufacture. TSA and 2C PUR coatings are preferably used, to make two-layer coatings, and melamine alkyd resins and Acrylic melamine resins are preferably used to make single layer coatings to manufacture.
Falls die Lacke gemäß der Erfindung für Zweischicht-Überzüge verwendet werden, ist der Lack, der die Verbindung der Formel I enthält, vorzugsweise die Deckschicht, die vorzugsweise eine Klarschicht ist.If the paints according to the invention are used for two-layer coatings are, the paint containing the compound of formula I is preferred the top layer, which is preferably a clear layer.
Bevorzugte metallische Lacke sind solche, die von TSA-Harzen abgeleitet sind, insbesonder solche, die abgeleitet sind von vernetzten Polyacrylatharzen mit Melamin-Formaldehydharzen, verethert mit Butanol, wie auch 2C-PUR-Harze, wie Hydroxygruppen-enthaltende Polyacrylatharze, gehärtet mit aliphatischen Isocyanaten.Preferred metallic paints are those derived from TSA resins are, in particular those which are derived from crosslinked polyacrylate resins with melamine-formaldehyde resins, etherified with butanol, such as also 2C-PUR resins, such as hydroxy group-containing polyacrylate resins, hardened with aliphatic isocyanates.
Die TSA-, A/MF-, 2C-PUR- und TPA-Harze werden beschrieben in "Lehrbuch der Lacke und Beschichtungen", H. Kittel, (Berlin) Band I, Teil 2 2 und im US-Patent 30 62 763; der Inhalt beider wird hier als Referenz eingebracht.The TSA, A / MF, 2C-PUR and TPA resins are described in "Textbook of paints and coatings", H. Kittel, (Berlin) Volume I, Part 2 2 and in U.S. Patent 3,062,763; the content of both is here for reference brought in.
Die Verbindungen der Formel I können allein oder in Kombination mit anderen Stabilisatoren, zum Beispiel Antioxidantien verwendet werden. Beispiele umfassen sterisch gehinderte Phenole, Schwefel- oder Phosphor-enthaltende Verbindungen oder deren Mischungen, Benzofuran-2-one, Indolin-2-one und sterisch gehinderte Phenole, wie β-(4-Hydroxy-3,5- ditert.butylphenyl)-propionyl-stearat, Methan-tetrakis-(methylen-3-(3′,5′- ditert.butyl-4′-hydroxy-phenyl)propionat), 1,3,3-Tris-(2-methyl-4-hydroxy- 5-tert.butyl-phenyl)butan, 1,3,5-Tris-(4-tert.butyl-3-hydroxy-2,6- dimethylbenzyl)-1,3,5-triazinyl-2,4,6-(1H,3H,5H)-trion, Bis-(4-tert.butyl- 3-hydroxy-2,6-dimethylbenzyl)dithiol-terephthalat, Tris-(3,5-ditert.butyl- 4-hydroxy-benzyl)-isocyanurat, der Triester von β-(4-Hydroxy-3,5- ditert.butylphenyl)-propionsäure mit 1,3,4-Tris-(2-hydroxyethyl)-5- triazinyl-2,4,6-(1H,3H,5H)-trion, Bis-(3,3-bis-(4′-hydroxy-3′- tert.butylphenyl)-buttersäure)glykol-ester, 1,3,5-Trimethyl-2,4,6-tris- (3,5-ditert.butyl-4-hydroxybenzyl)-benzol, 2,2′-Methylen-bis-(4-methyl-6- tert.butylphenyl)-terephthalat, 4,4-Methylen-bis-(2,6-ditert.butylphenol), 4,4′-Butyliden-bis-(tert.butylmetakresol), 2,2′-Methylen-bis-(4-methyl-6- tert.butyl)-phenol.The compounds of formula I can be used alone or in combination with other stabilizers, for example antioxidants. Examples include sterically hindered phenols, sulfur- or phosphorus-containing compounds or mixtures thereof, benzofuran-2-ones, indolin-2-ones and sterically hindered phenols such as β - (4-hydroxy-3,5-ditert.butylphenyl) - propionyl stearate, methane tetrakis (methylene-3- (3 ', 5'-ditert.butyl-4'-hydroxy-phenyl) propionate), 1,3,3-tris- (2-methyl-4-hydroxy - 5-tert-butyl-phenyl) butane, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) -1,3,5-triazinyl-2,4,6 - (1H, 3H, 5H) -trione, bis- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol terephthalate, tris- (3,5-ditert.butyl-4-hydroxy-benzyl ) -isocyanurate, the triester of β - (4-hydroxy-3,5-ditert.butylphenyl) propionic acid with 1,3,4-tris (2-hydroxyethyl) -5-triazinyl-2,4,6- ( 1H, 3H, 5H) -trione, bis- (3,3-bis- (4'-hydroxy-3'-tert.butylphenyl) butyric acid) glycol ester, 1,3,5-trimethyl-2,4, 6-tris (3,5-ditert.butyl-4-hydroxybenzyl) benzene, 2,2'-methylene bis (4-methyl-6-tert.butylphenyl) terephthalate, 4,4-methylene bis - (2,6-ditert.buty lphenol), 4,4'-butylidene-bis- (tert-butylmetacresol), 2,2'-methylene-bis- (4-methyl-6-tert.butyl) -phenol.
Schwefel-enthaltende antioxidative Costabilisatoren, die verwendet werden können, umfassen zum Beispiel Distearylthiodipropionat, Dilaurylthiodipropionat, Methan-tetrakis-(methylen-3-hexylthiopropionat), Methan-tetrakis-(methylen-3-dodecylthiopropionat) und Diocatadecyldisulfid.Sulfur-containing antioxidant costabilizers used can include, for example, distearyl thiodipropionate, Dilauryl thiodipropionate, methane tetrakis (methylene-3-hexylthiopropionate), Methane tetrakis (methylene-3-dodecylthiopropionate) and diocatadecyl disulfide.
Phosphor-enthaltende Costabilisatoren umfassen zum Beispiel Trinonylphenyl-phosphit, 4,9-Distearyl-3,5,8,10-Tetraoxadiphosphaspiro- undecan, Tris-(2,4-Ditert.butylphenyl)phosphit und Tetrakis-(2,4- ditert.butylphenyl)-4,4′-biphenylen-diphosphonit.For example, phosphorus-containing costabilizers include Trinonylphenyl phosphite, 4,9-distearyl-3,5,8,10-tetraoxadiphosphaspiro- undecane, tris (2,4-ditert.butylphenyl) phosphite and tetrakis (2,4- ditert.butylphenyl) -4,4'-biphenylene-diphosphonite.
Weitere Zusätze, wie Aminoaryl-Verbindungen und U. V.-Absorber und Lichtstabilisatoren, z. B. substituiertes 2-(2′-Hydroxyphenyl)-benzotriazol, 2-Hydroxy-benzophenon, 1,3-Bis-(2′-hydroxybenzoyl)-benzol, Salicylate, Cinnamate, Benzoate und substituierte Benzoate und andere sterisch gehinderte Amine (HALS) und Oxalsäurediamide können verwendet werden. Andere bekannte Arten von Zusätzen können ebenfalls zugesetzt werden, z. B. Flammschutzmittel und antistatische Mittel.Other additives such as aminoaryl compounds and U.V. absorbers and Light stabilizers, e.g. B. substituted 2- (2'-hydroxyphenyl) benzotriazole, 2-hydroxy-benzophenone, 1,3-bis (2'-hydroxybenzoyl) benzene, Salicylates, cinnamates, benzoates and substituted benzoates and others hindered amines (HALS) and oxalic acid diamides can be used will. Other known types of additives can also be added be, e.g. B. Flame retardants and antistatic agents.
Vorzugsweise wird eine Verbindung der Formel XXPreferably a compound of formula XX
worin R₃₀ C6-22-Alkyl oder C6-22-Alkoxy ist;
R₃₁ und R₃₂ unabhängig voneinander Wasserstoff, C1-8-Alkyl, C1-12-
Alkoxy, C1-12-Alkylthio, Phenoxy oder Phenylthio bedeuten, mit der
Maßgabe, daß nur eines von R₃₁ und R₃₂ Alkylthio, Phenoxy oder Phenylthio
ist und
R₃₃ Wasserstoff oder C1-8-Alkyl ist, zu einer Verbindung der Formel
I zugesetzt.wherein R₃₀ is C 6-22 alkyl or C 6-22 alkoxy;
R₃₁ and R₃₂ independently represent hydrogen, C 1-8 alkyl, C 1-12 alkoxy, C 1-12 alkylthio, phenoxy or phenylthio, with the proviso that only one of R₃₁ and R₃₂ is alkylthio, phenoxy or phenylthio and
R₃₃ is hydrogen or C 1-8 alkyl, added to a compound of formula I.
Vorzugsweise beträgt die Menge einer Verbindung der Formel I, die in einem Lack gemäß der Erfindung verwendet werden kann, 0.1 bis 8 Gew.-% der Feststoffe im Lack, noch besser 0.5 bis 5%.The amount of a compound of the formula I which is in a paint according to the invention can be used, 0.1 to 8 wt .-% of Solids in the paint, even better 0.5 to 5%.
Die Erfindung wird nun durch die folgenden Beispiele erläutert, wobei sich alle Teile und Prozentzahlen auf Gewicht und alle Temperaturen auf °C beziehen, außer es ist das Gegenteil angegeben. Die Menge des Lichtstabilisators ist auf das Feststoffgewicht in den Lacken bezogen.The invention will now be illustrated by the following examples, wherein all parts and percentages by weight and all temperatures to ° C unless the contrary is stated. The amount of light stabilizer is based on the solids weight in the paints.
Ein metallischer Zweischichtüberzug, enthaltend einen Grundüberzug und einen klaren Decküberzug kann aus den folgenden Lacken hergestellt werden.A metallic two-layer coating containing a basic coating and a clear top coat can be made from the following paints.
18.75% klarer Überzugslack 1, nachstehend definiert (50% Feststoff)
51.75% Cellulose-Acetobutyrat-Lösung (20%), im Handel erhältlich
als Cellit BP 500
13.54% n-Butylacetat
6.45% Xylol
5.15% Ethylenglykolacetat
0.26% Anti-Sedimentationsmedium : Aerosil 200
3.85% einer 65%igen Aluminiumpaste in Ethylenglykolacetat, im Handel
erhältlich als Alcoci 7530
0.25% 18.75% clear top coat 1, defined below (50% solids)
51.75% cellulose acetobutyrate solution (20%), commercially available as Cellit BP 500
13.54% n-butyl acetate
6.45% xylene
5.15% ethylene glycol acetate
0.26% anti-sedimentation medium: Aerosil 200
3.85% of a 65% aluminum paste in ethylene glycol acetate, commercially available as Alcoci 7530
0.25%
Phthalocyanin-Blau (C. I. Pigment Blue 15 : 1)
100.00% (das Verhältnis von Pigment zu Aluminium ist etwa 1 : 10)Phthalocyanine Blue (CI Pigment Blue 15: 1)
100.00% (the ratio of pigment to aluminum is about 1:10)
Klarer Überzugslack 1 wird wie folgt formuliert:Clear top coat 1 is formulated as follows:
80.00% eines Acrylharzes, im Handel erhältlich als Viacryl SC344 -
50%ig in einer Lösung von Xylol und n-Butanol (4 : 1-Verhältnis)
13.90% Melaminharz
4.10% n-Butanol und
2.00% eines Verdünnungsmittels, im Handel erhältlich als Byketol OK.80.00% of an acrylic resin, commercially available as Viacryl SC344 - 50% in a solution of xylene and n-butanol (4: 1 ratio)
13.90% melamine resin
4.10% n-butanol and
2.00% of a diluent, commercially available as Byketol OK.
Ein grundiertes 10 × 30 cm Aluminiumstück wird naß in naß mit dem Grundüberzugslack und dann dem klaren Überzugslack, dem 1% einer Verbindung der Formel 1aA primed 10 × 30 cm piece of aluminum gets wet in wet with the Base coat and then the clear coat, the 1% one Compound of formula 1a
zugesetzt wurde, überzogen, was einen 15 µ-Grundüberzug und einen 35 µ-Klarüberzug ergibt.Was added, which was a 15 micron base coat and a 35 micron clear coat results.
Das so behandelte Aluminiumstück wird dann 35 Minuten bei 140°C ofengetrocknet. The aluminum piece treated in this way is then 35 minutes at 140 ° C. oven dried.
Beispiel 1 wird wiederholt, wobei anstelle der Verbindung der Formel 1a 1% einer der Verbindungen der Formel 2a bis 3a verwendet werden.Example 1 is repeated, using instead of the compound of formula 1a 1% of one of the compounds of the formula 2a to 3a can be used.
Die Beispiele 1, 2 und 3 können wiederholt werden, wobei 2.2% (aktives Material) des Monobutylesters von Maleinsäure zum Klarlack zugesetzt werden und anstelle der Ofentrocknung bei 140°C während 35 Minuten der Lack 30 Minuten lang bei 90°C säuregehärtet wird.Examples 1, 2 and 3 can be repeated, 2.2% (active material) of the monobutyl ester from maleic acid to the clear coat be added and instead of oven drying at 140 ° C for 35 Minutes, the varnish is acid-cured at 90 ° C for 30 minutes.
Ein Zweischichtenüberzug, bei dem die Deckschicht 2C-PUR ist, kann wie folgt hergestellt werden:A two-layer coating in which the top layer is 2C-PUR can can be produced as follows:
Ein Grundüberzugslack wird wie in Beispiel 1 hergestellt.A base coat varnish is produced as in Example 1.
Ein Klarlack wird wie folgt hergestellt:A clear coat is made as follows:
Die erste Komponente des 2C-PUR enthältThe first component of the 2C-PUR contains
44.1% eines Hydroxygruppen-enthaltenden Acrylharzes (OH-Zahl etwa
150), im Handel erhältlich als Macrynal SM 510 N, eine 60%ige Lösung in
Xylol und Ethylenglykolacetat (Verhältnis 4 : 1)
35.2% einer Verdünnungsmischung aus Methylethylketon und Xylol (1 : 1)
3.0% Byketol spezial: im Handel erhältliches Verlaufmittel
(Silicon-enthaltend)44.1% of an hydroxy resin-containing acrylic resin (OH number about 150), commercially available as Macrynal SM 510 N, a 60% solution in xylene and ethylene glycol acetate (ratio 4: 1)
35.2% of a dilution mixture of methyl ethyl ketone and xylene (1: 1)
3.0% Byketol special: commercially available leveling agent (containing silicone)
Die zweite Komponente enthältThe second component contains
17.7% eines aliphatischen Polyisocyanats, im Handel erhältlich als Desmodin N (das eine 75%ige Lösung in Xylol/Ethylenglykolacetat 4 : 1 ist).17.7% of an aliphatic polyisocyanate, commercially available as Desmodin N (which is a 75% solution in 4: 1 xylene / ethylene glycol acetate).
Die zweite Komponente wird dann zu der ersten Komponente zugesetzt und (wie oben angegeben) naß gemischt. Zu dem so gebildeten 2C-PUR wird 1% der Verbindung von Formel 1a zugesetzt.The second component is then added to the first component and (as stated above) wet mixed. 1% is added to the 2C-PUR thus formed added to the compound of formula 1a.
Die Grund- und die Klarschichten (in der gleichen Dicke, wie in Beispiel 1 angegeben) werden wie in Beispiel 1 beschrieben auf ein Aluminiumstück naß in naß aufgebracht. Die Lacke werden dann 35 Minuten lang bei 80°C ofengetrocknet.The base and clear layers (in the same thickness as in Example 1 given) are as described in Example 1 Aluminum piece applied wet on wet. The paints are then 35 minutes long oven dried at 80 ° C.
Beispiel 5 kann wiederholt werden, wobei 1% eine der Verbindungen der Formeln 2a-3a (oben definiert) verwendet wird.Example 5 can be repeated, with 1% being one of the compounds of formulas 2a-3a (defined above) is used.
Claims (8)
jedes R₂ unabhängig voneinander -CH₃ oder -CH₂(C1-4-Alkyl) ist oder beide Gruppen R₂ eine Gruppe -(CH₂)₅- bilden;
R Wasserstoff, Sauerstoff, C1-8-Alkyl oder -COR₅ ist;
wobei R₅ -C(R₁₃)=CH₂, C1-6-Alkyl, Phenyl, -NR₇R₈, -CO-C₆H₅, -CH₂-C₆H₅, -COOC1-12-Alkyl oder -COOH ist; R₇ Wasserstoff, C1-12-Alkyl, C5-6-Cycloalkyl, Phenyl, Phenyl-C1-4-Alkyl ist;
R₁₃ die unten angegebene Bedeutung hat;
R₄ -NR₁₃R₁₄ ist oder eine Gruppe der Formel α worin R₁₃ Wasserstoff oder unsubstituiertes oder durch OH monosubstituiertes C1-6-Alkyl ist;
R₁₄ Wasserstoff oder unsubstituiertes oder durch OH monosubstituiertes C1-6-Alkyl ist; und
X C1-12-Alkylen ist.1. Lacquer, characterized by a thermosetting acrylic resin, an alkyd-melamine-formaldehyde resin, a two-component polyurethane resin (or resins which form a two-component polyurethane resin) or a thermoplastic acrylic resin and a UV-stabilizing amount of a compound of the formula I wherein each R₁ is independently -CH₃ or -CH₂ (C 1-4 alkyl) or both groups R₁ form a group - (CH₂) ₅-;
each R₂ is independently -CH₃ or -CH₂ (C 1-4 alkyl) or both groups R₂ form a group - (CH₂) ₅-;
R is hydrogen, oxygen, C 1-8 alkyl or -COR₅;
wherein R₅ is -C (R₁₃) = CH₂, C 1-6 alkyl, phenyl, -NR₇R₈, -CO-C₆H₅, -CH₂-C₆H₅, -COOC 1-12 alkyl or -COOH; R₇ is hydrogen, C 1-12 alkyl, C 5-6 cycloalkyl, phenyl, phenyl-C 1-4 alkyl;
R₁₃ has the meaning given below;
R₄ is -NR₁₃R₁₄ or a group of the formula α wherein R₁₃ is hydrogen or C 1-6 alkyl unsubstituted or monosubstituted by OH;
R₁₄ is hydrogen or unsubstituted or C 1-6 alkyl monosubstituted by OH; and
XC is 1-12 alkylene.
Applications Claiming Priority (1)
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|---|---|---|---|
| GB898907595A GB8907595D0 (en) | 1989-04-04 | 1989-04-04 | Improvements in or relating to organic compounds |
Publications (1)
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| DE4010444A1 true DE4010444A1 (en) | 1990-10-11 |
Family
ID=10654453
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| DE4010444A Withdrawn DE4010444A1 (en) | 1989-04-04 | 1990-03-31 | USE OF NECK CONNECTIONS IN VARNISHES |
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| CH (1) | CH680667A5 (en) |
| DE (1) | DE4010444A1 (en) |
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| GB (2) | GB8907595D0 (en) |
| IT (1) | IT1240814B (en) |
Cited By (2)
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|---|---|---|---|---|
| EP0839845A1 (en) * | 1996-11-02 | 1998-05-06 | Hüls Aktiengesellschaft | Blocked polyisocyanates with built-in HALS-stabilizer |
| EP0839844A1 (en) * | 1996-11-02 | 1998-05-06 | Hüls Aktiengesellschaft | Lacquers polyisocyanates with built-in HALS-stabilizer |
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| GB9511486D0 (en) * | 1995-06-07 | 1995-08-02 | Sandoz Ag | Organic compounds |
| US20220356155A1 (en) * | 2021-04-30 | 2022-11-10 | Exxonmobil Research And Engineering Company | Fuel high temperature antioxidant additive |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2963604D1 (en) * | 1978-06-21 | 1982-10-28 | Ciba Geigy Ag | Light stabilization of acid catalysed stoving enamels |
| BR8007463A (en) * | 1979-11-21 | 1981-06-02 | Du Pont | IMPROVEMENT IN COMPOSITION FOR COATING WITH HIGH CONTENT IN SOLID AND SUBSTRATE WITH FINISHING A TOP LAYER OF TRANSPARENT COATING |
| EP0052073B1 (en) * | 1980-11-10 | 1987-08-19 | Ciba-Geigy Ag | Light stabilization of acid catalysed storing enamels |
| JPS5892660A (en) * | 1981-11-27 | 1983-06-02 | Adeka Argus Chem Co Ltd | Piperidylamine compound |
| FR2543151B1 (en) * | 1983-03-21 | 1986-11-07 | Sandoz Sa | LIQUID COMPOSITIONS BASED ON STABILIZERS AGAINST ULTRAVIOLET RADIATION |
| JPS60197775A (en) * | 1984-03-21 | 1985-10-07 | Adeka Argus Chem Co Ltd | Thermosetting synthetic resin paint composition |
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- 1989-04-04 GB GB898907595A patent/GB8907595D0/en active Pending
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- 1990-03-30 FR FR9004222A patent/FR2645165A1/en active Pending
- 1990-03-31 DE DE4010444A patent/DE4010444A1/en not_active Withdrawn
- 1990-04-02 CH CH1091/90A patent/CH680667A5/de not_active IP Right Cessation
- 1990-04-03 JP JP2087631A patent/JPH0354267A/en active Pending
- 1990-04-03 GB GB9007447A patent/GB2230014B/en not_active Expired - Lifetime
- 1990-04-04 IT IT47830A patent/IT1240814B/en active IP Right Grant
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6204351B1 (en) | 1996-02-11 | 2001-03-20 | Huels Aktiengesellschaft | Blocked polyisocyanates with built-in hals stabilizer |
| EP0839845A1 (en) * | 1996-11-02 | 1998-05-06 | Hüls Aktiengesellschaft | Blocked polyisocyanates with built-in HALS-stabilizer |
| EP0839844A1 (en) * | 1996-11-02 | 1998-05-06 | Hüls Aktiengesellschaft | Lacquers polyisocyanates with built-in HALS-stabilizer |
| US5955558A (en) * | 1996-11-02 | 1999-09-21 | Huels Aktiengesellschaft | Blocked polyisocyanates with built-in HALS stabilizer |
Also Published As
| Publication number | Publication date |
|---|---|
| CH680667A5 (en) | 1992-10-15 |
| GB2230014B (en) | 1992-05-20 |
| GB9007447D0 (en) | 1990-05-30 |
| FR2645165A1 (en) | 1990-10-05 |
| GB8907595D0 (en) | 1989-05-17 |
| GB2230014A (en) | 1990-10-10 |
| IT9047830A0 (en) | 1990-04-04 |
| IT9047830A1 (en) | 1991-10-04 |
| IT1240814B (en) | 1993-12-17 |
| JPH0354267A (en) | 1991-03-08 |
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