CA2034952C - Protective coating for wood against damage by light containing undercoating comprising sterically hindered phenols - Google Patents
Protective coating for wood against damage by light containing undercoating comprising sterically hindered phenols Download PDFInfo
- Publication number
- CA2034952C CA2034952C CA002034952A CA2034952A CA2034952C CA 2034952 C CA2034952 C CA 2034952C CA 002034952 A CA002034952 A CA 002034952A CA 2034952 A CA2034952 A CA 2034952A CA 2034952 C CA2034952 C CA 2034952C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- resins
- tert
- butyl
- undercoat
- 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.)
- Expired - Fee Related
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- 239000002023 wood Substances 0.000 title claims abstract description 31
- 239000011253 protective coating Substances 0.000 title claims abstract description 8
- 150000002989 phenols Chemical class 0.000 title claims description 6
- 239000004611 light stabiliser Substances 0.000 claims abstract description 16
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 37
- 230000003078 antioxidant effect Effects 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000180 alkyd Polymers 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical group 0.000 claims description 10
- -1 glycol ethers Chemical class 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 239000000020 Nitrocellulose Substances 0.000 claims description 8
- 229920001568 phenolic resin Polymers 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229920001220 nitrocellulos Polymers 0.000 claims description 7
- 239000005011 phenolic resin Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 5
- 239000003755 preservative agent Substances 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 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 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 4
- 239000004645 polyester resin Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 4
- 239000011118 polyvinyl acetate Substances 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 230000002335 preservative effect Effects 0.000 claims description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 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 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 229940079938 nitrocellulose Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 101710179738 6,7-dimethyl-8-ribityllumazine synthase 1 Proteins 0.000 description 3
- 101710179734 6,7-dimethyl-8-ribityllumazine synthase 2 Proteins 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 101710186608 Lipoyl synthase 1 Proteins 0.000 description 3
- 101710137584 Lipoyl synthase 1, chloroplastic Proteins 0.000 description 3
- 101710090391 Lipoyl synthase 1, mitochondrial Proteins 0.000 description 3
- 101710186609 Lipoyl synthase 2 Proteins 0.000 description 3
- 101710122908 Lipoyl synthase 2, chloroplastic Proteins 0.000 description 3
- 101710101072 Lipoyl synthase 2, mitochondrial Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 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
- 239000008199 coating composition Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
- ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical class CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- LKALLEFLBKHPTQ-UHFFFAOYSA-N 2,6-bis[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=CC(C)=CC=1CC1=CC(C)=CC(C(C)(C)C)=C1O LKALLEFLBKHPTQ-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
- JBYWTKPHBLYYFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JBYWTKPHBLYYFJ-UHFFFAOYSA-N 0.000 description 1
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 1
- SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 1
- UDFARPRXWMDFQU-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanylmethyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CSCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 UDFARPRXWMDFQU-UHFFFAOYSA-N 0.000 description 1
- LBOGPIWNHXHYHN-UHFFFAOYSA-N 2-(2-hydroxy-5-octylphenyl)sulfanyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCC)C=2)O)=C1 LBOGPIWNHXHYHN-UHFFFAOYSA-N 0.000 description 1
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- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/06—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood
- B05D7/08—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood using synthetic lacquers or varnishes
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/002—Priming paints
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A protective coating for wood comprising a) an undercoat which penetrates the surface of the wood and contains a phenolic antioxidant, and b) a conventional top coat.
The top coat preferably contains a light stabiliser.
The top coat preferably contains a light stabiliser.
Description
Protective Coating for Wood a ainst damage by light containing Undercoating comprising Sterically Hindered Phenols The present invention relatca to a method of protecting wood surfaces against damage by light and to a protective coating for wood.
Wood surfaces which are exposed to sunlight are damaged in particular by the UV light present in the sunlight. The polymeric constituents of the wood are degraded, so that the surface undergoes roughening and discolouration. As a consequence, attack by microorganisms, especially fungi, giives rise to further damage.
The conventional method of protecting wood against light-induced degradation, without having to forgo the attractive appearance of the wood surface, is to coat the wood with a colourless varnish which contains a light stabiliser, especially a UV
absorber.
Investigations have also bec,n made to determine whether the addition of an antioxidant to the protective coatings rein:Forces the effect of the light stabiliser in the wood varnish.
According to D.N.S. Hon et al., J. Appl. Polymer Sci. 30 (1985), 1439, no, or only an insignificant effect, is obtained.
The addition of phenolic antioxidanla to wood varnishes is known. For example, US patent specification 3285855 discloses the colour stabilisation of furniture varnishes based on acid-curable urea/formaldehyde alkyd resins by adding 0.2% by weight of a phenolic antioxidant.
Wood protective coatings which contain a UV absorber, an antioxidant and an insecticide are disclosed in the publication of the JF' patent application Sho 59-115 805, published July 4, 1984.
It has now been found that antioxidants of the type of the the sterically hindered phenols have a marked stabilising acaion against light-induced degradation if they are applied, without the addition of a light stabiliser, to an undercoat which penetrates the surface of the wood, and the wood is then provided with a top coat, which top coat may contain a light stabiliser.
Accordingly, the invention ,relates to a method of protecting wood surfaces against light-induced degradation by treatment with a) an undercoat which penetrates thc: surface of the wood and which does not contain a light stabiliser, said undercoat comprising an aqueous or organic solvent, or said solvent containing a binder selecaed frorr~ the group consisting of alkyd resins, modified alkyd resins, acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose resins and mixtures thereof, and b) one or more top coats, comprising a resin selected from the group consisting of nitrocellu-lose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, alkyd resins and mixtures thereof, said undercoat containing 0.05 to 10 % by weight of at least one antioxidant of the type of the sterically hindered phenols.
The antioxidant is preferablly a compound which contains at least one group of formula I
R
HO
~CH3~3C
wherein R is hydrogen, mei:hyl or tert-butyl, preferably wherein R is tert-butyl.
The antioxidant is preferably an ester of b-(3,5-di-tert-butyl-4-hydroxyphenyl~ropionic acid, more particularly a compound of formula II
t-C4H6 HO ~ ~ CFizCHZC00- R~ II
t-CQH9 wherein n is 1, 2 or 4 and, when n =: l, RI is CgH,~, and when n = 2, Rt is -(CH2)6- or -CH2CH20CH2CHZOCH2CH2-, and, when n = 4, R1 is -(CHZ)4C , The antioxidant is also preferably a compound of formula III
H H H
z Rz C Rz III
j~~~~9~~
Wood surfaces which are exposed to sunlight are damaged in particular by the UV light present in the sunlight. The polymeric constituents of the wood are degraded, so that the surface undergoes roughening and discolouration. As a consequence, attack by microorganisms, especially fungi, giives rise to further damage.
The conventional method of protecting wood against light-induced degradation, without having to forgo the attractive appearance of the wood surface, is to coat the wood with a colourless varnish which contains a light stabiliser, especially a UV
absorber.
Investigations have also bec,n made to determine whether the addition of an antioxidant to the protective coatings rein:Forces the effect of the light stabiliser in the wood varnish.
According to D.N.S. Hon et al., J. Appl. Polymer Sci. 30 (1985), 1439, no, or only an insignificant effect, is obtained.
The addition of phenolic antioxidanla to wood varnishes is known. For example, US patent specification 3285855 discloses the colour stabilisation of furniture varnishes based on acid-curable urea/formaldehyde alkyd resins by adding 0.2% by weight of a phenolic antioxidant.
Wood protective coatings which contain a UV absorber, an antioxidant and an insecticide are disclosed in the publication of the JF' patent application Sho 59-115 805, published July 4, 1984.
It has now been found that antioxidants of the type of the the sterically hindered phenols have a marked stabilising acaion against light-induced degradation if they are applied, without the addition of a light stabiliser, to an undercoat which penetrates the surface of the wood, and the wood is then provided with a top coat, which top coat may contain a light stabiliser.
Accordingly, the invention ,relates to a method of protecting wood surfaces against light-induced degradation by treatment with a) an undercoat which penetrates thc: surface of the wood and which does not contain a light stabiliser, said undercoat comprising an aqueous or organic solvent, or said solvent containing a binder selecaed frorr~ the group consisting of alkyd resins, modified alkyd resins, acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose resins and mixtures thereof, and b) one or more top coats, comprising a resin selected from the group consisting of nitrocellu-lose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, alkyd resins and mixtures thereof, said undercoat containing 0.05 to 10 % by weight of at least one antioxidant of the type of the sterically hindered phenols.
The antioxidant is preferablly a compound which contains at least one group of formula I
R
HO
~CH3~3C
wherein R is hydrogen, mei:hyl or tert-butyl, preferably wherein R is tert-butyl.
The antioxidant is preferably an ester of b-(3,5-di-tert-butyl-4-hydroxyphenyl~ropionic acid, more particularly a compound of formula II
t-C4H6 HO ~ ~ CFizCHZC00- R~ II
t-CQH9 wherein n is 1, 2 or 4 and, when n =: l, RI is CgH,~, and when n = 2, Rt is -(CH2)6- or -CH2CH20CH2CHZOCH2CH2-, and, when n = 4, R1 is -(CHZ)4C , The antioxidant is also preferably a compound of formula III
H H H
z Rz C Rz III
j~~~~9~~
wherein R2 is hydrogen, methyl or tert-butyl, preferably wherein R2 is tert-butyl.
The antioxidant is also preferably a compound of formula IV
R3 / Rs IV
CH3 ~ CH3 C4H9-t wherein R3 is a group -CH2 ~ ~ OH
CaHs_t The antioxidant is also preferably a compound of formula V
OH
t-C4H9 /
CH3 - C - CH2C00 ~ R4 V
m C4H9-t OH
wherein either m is 1 and R4 is methyl, or rn is 2 and R4 is -CH2CI-I2-.
The antioxidant is also preferably a compound of formula VI
The antioxidant is also preferably a compound of formula IV
R3 / Rs IV
CH3 ~ CH3 C4H9-t wherein R3 is a group -CH2 ~ ~ OH
CaHs_t The antioxidant is also preferably a compound of formula V
OH
t-C4H9 /
CH3 - C - CH2C00 ~ R4 V
m C4H9-t OH
wherein either m is 1 and R4 is methyl, or rn is 2 and R4 is -CH2CI-I2-.
The antioxidant is also preferably a compound of formula VI
t ~4H9 (~4H9_t HO ~ ~ C ~ ~ OH VI
I
R~
Rs Rs Rs Rio wherein RS and Rto are hydrogen or tert-butyl, R6 and R9 are hydrogen or methyl, R~ is hydrogen or methyl and Rs is hydrogen or Ct-C4alkyl.
The antioxidant is also preferably 3,5-di-tert-butyl-4-hydroxytoluene.
The following compounds are illustrative of antioxidants which are suitable for use in the method of this invention:
1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tri-eyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methyl-phenol.
2. Alkylated hydroduinones, for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-ten-amylhydroquinone, 2,6-diphenyl-4-octadecyloxy-phenol.
3. Hydroxylated thiodiphenyl ethers, for example 2,2'-thiobis(6-tent-butyl-4-methyl-phenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol).
4. Alkylidenebisphenols, for example 2,2'-methylenebis(6-tent-butyl-4-methylphenol), 2,2'-methylenebis(6-tent-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-methyl-eyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tent-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(a-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis(6-(a,a-dimethyl--, benzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methylene-bis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxy-phenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tent-butyl-4methylphenyl]
terephthalate.
5. Benzyl compounds, for example 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis(4-tent-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiolterephthalate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-Iris(4-tent-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, calcium salt of monoethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.
I
R~
Rs Rs Rs Rio wherein RS and Rto are hydrogen or tert-butyl, R6 and R9 are hydrogen or methyl, R~ is hydrogen or methyl and Rs is hydrogen or Ct-C4alkyl.
The antioxidant is also preferably 3,5-di-tert-butyl-4-hydroxytoluene.
The following compounds are illustrative of antioxidants which are suitable for use in the method of this invention:
1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tri-eyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methyl-phenol.
2. Alkylated hydroduinones, for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-ten-amylhydroquinone, 2,6-diphenyl-4-octadecyloxy-phenol.
3. Hydroxylated thiodiphenyl ethers, for example 2,2'-thiobis(6-tent-butyl-4-methyl-phenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol).
4. Alkylidenebisphenols, for example 2,2'-methylenebis(6-tent-butyl-4-methylphenol), 2,2'-methylenebis(6-tent-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(a-methyl-eyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tent-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(a-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis(6-(a,a-dimethyl--, benzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methylene-bis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxy-phenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tent-butyl-4methylphenyl]
terephthalate.
5. Benzyl compounds, for example 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis(4-tent-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiolterephthalate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-Iris(4-tent-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, calcium salt of monoethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.
6. Acylaminophenols, for example 4-hydroxylauranilide, 4-hydroxystearanilide, 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-s-triazine, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.
7. Esters of 13-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono-or polyhydric alcohols, e.g. with methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, thiodiethylene glycal, N,N'-bis(hydroxyethyl)oxalodiamide.
8. Esters of 13-(5-tent-butyl-4-hydroxy-3-methylphen~propionic acid with mono-or polyhydric alcohols, e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexaaediol, pentaerythritol, neopentyl glycol, tris(hydroxyethyl) isocyanurate, thiodiethylene glycol, N,N'-bis(hydroxyethyl)oxalodiamide.
9. Esters of J3-(3 5-dicyclohexyl-4-hydroxyphe~l)propionic acid with mono- or poly-hydric alcohols, e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris(hydroxyethyl) isocyanurate, thiodiethylene glycol, N,N'-bis(hydroxyethyl)oxalodiamide.
10. Amides of B-(3,5-di-tert-but~vdroxyphe~l)propionic acid e.g. N,N'-bas(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine.
In specific cases it may be useful to use two or more antioxidants.
The undercoat shall penetrate the surface of the wood, and should therefore be of relatively low viscosity. In the simplest case, the undercoat is a solution of the antioxidant in an organic solvent. Exemplary of useful solvents for the purpose are aliphatic hydrocarbons such as specific petroleum fractions. Further suitable solvents are aromatic hydrocarbons such as toluene or xylene; alcohols such as methanol, ethanol, isopropanol or butanol; esters such as ethyl acetate or butyl acetate; or ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone. These solvents evaporate at room temperature and therefore do not remain in the wood. It is, however, also possible to add high boiling liquids which remain in the wood, for example higher alkanols, glycols, glycol ethers, glycol esters or polyglycols. The undercoat may also contain a binder conventionaliy used for protective wood coatings. Exemplary of suitable binders are alkyd resins and modified alkyd resins, autocrosslinking or non-autocrosslinking acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose or mixtures thereof.
The undercoat may also contain one or more phosphates which synergise the action of the antioxidants. Illustrative examples of such phosphates are:
triphenyl phosphate, diphenylalkyl phosphate, phenyldialkyl phosphate, tris(nonylphenyl) phosphate, trilauryl phosphate, trioctadecyl phosphate, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphate, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tent-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite.
Tris-(2,4-di-tv;rt-butylphenyl) phosphate is particularly preferred.
The undercoat may also contain preservatives such as fungicides or insecticides.
Exemplary of useful fungicides are tributyltin oxide, phenylmercury salts, copper naphthenate, 1-chloronaphthalene or pentachlorophenol. Exemplary of useful insecticides are DDT, dieldrin, lindane, parathion or phoxime.
Further ingredients which may be present in the undercoat are minor amounts of accelerators (hardeners) for the binders, dyes or pigments.
The undercoat consists mainly of the solvent and contains typically 0.05 to 10 %, preferably 0.1 to 5 %, of the antioxidant. It can further contain 0.1 to 5 %
by weight of a phosphite.
The undercoat can be applied to the wood by conventional techniques, for example by impregnating, spreading or spraying.
The undercoat may also be an aqueous coating. Instead of the organic solvent, the vehicle may then consist of water or a mixture of water and a water-soluble organic solvent. The antioxidant and the other components may be dissolved or dispersed in this vehicle.
Any coating composition suitable for coating wood may be used as top coat. It will normally contain a binder, dissolved or dispersed in an organic solvent or in water or a mixture of water and solvent. The binder may typically be a surface coating resin which dries in the air or hardens at room temperature. Exemplary of such binders are nitrocellulose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, and especially alkyd resins.
The binder may also be a mixture of different surface coating resins. Provided the binders are curable binders, they are normally used together with the hardener and/or accelerator.
Typical examples of organic solvents which may suitably be used for the coating compositions are aliphatic, aromatic or cycloaliphatic hydrocarbons, alcohols, esters, ketones or chlorinated hydrocarbons.
Water/solvent mixtures are typically mixtures of water and lower alcohols, glycols or glycol ethers.
The top coat may also be a radiation-curable, solvent-free formulation of photopolymerisable compounds. Illustrative examples are mixtures of acrylates or methacrylates, unsaturated polyester/styrene mixtures or mixtures of other ethylenically unsaturated monomers or oligomers.
The top coat may contain a soluble dye and/or a pigment and/or a filler. The pigment may be an organic, inorganic or metallic pigment. The filler may be typically kaolin, calcium carbonate or aluminium silicate. Preferably the top coat is a clear varnish, i.e. it contains no undissolved components.
~\
-g-Although the top coat which contains the antioxidant affords good protection against light, it is advantageous to add a light stabiliser to the top coat.111ustrative examples of suitable light stabilisers are the following compounds:
1. 2-(2'-Hydroxvphenyl)benzotriazoles for example the 5'-methyl, 3',5'-di-tert-butyl, 5'-tert-butyl, 5'-(1,1,3,3-tetramethylbutyl), 5-chloro-3',5'-di-tert-butyl, 5-chloro-3'-tert-butyl-5'-methyl, 3'-sec- butyl-5'-tert-butyl, 4'-octoxy, 3',5'-di-tert-amyl and 3',5'-bis(a,a-dimethylbenzyl) derivative, the octyl ester of 3-(5-chlorobenzotriazol-2-yl)-4-hydroxy-5-tert-butylphenylpropionic acid or the polyglycol 300 ester of 3-(benzo-triazol-2-yl)-4-hydroxy-5-tert-butylphenylpropionic acid.
2. 2-Hydrox benzophenones for example the 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivative.
3. Esters of substituted and unsubstituted benzoic acids for example, 4-tent-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tent-butylbenzoyl)-resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxy- benzoate and hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate.
4Acrylates, for example ethyl a-cyano-~i,~3-diphenylacrylate, isooctyl a-cyano-(3,(3-diphenylacrylate, methyl a-carbomethoxycinnamate, methyl a-cyano-~i-methyl-p-methoxy-cinnamate, butyl a-cyano-(3-methyl-p-methoxy- cinnamate, methyl a-carbo-methoxy-p-methoxycinnamate and N-(p-carbomethoxy-~3-cyanovinyl)-2-methylindoline.
5. Nickel compounds for example nickel complexes of 2,2'-thio-bis(4-(1,1,3,3-tetra-methylbutyl)phenol], such as the 1:1 or 1:2 complex, with, or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyl-dithiocarbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzyl-phosphonic acid monoalkyl esters, e.g. of the methyl or ethyl ester, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methyl-phenyl undecyl ketoneoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands. -6. Sterically hindered amines, for example bis(2,2,6,6-tetramethylpiperidyl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) ~~~~,~5 n-butyl-3,5-di-tert-butyl-4-hydroxy-benzylmalonate, the condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the condensation product of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butane-tetraoate, 1,1'-(1,2-ethanediyl)bis-(3,3,5,5-tetramethylpipexazinone).
7. Oxalvl diamides for example 4,4'-dioctyloxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butaxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxalamide, 2-ethoxy-5-tert-butyl-2'-ethyloxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide and mixtures of ortho- and para-methoxy-disubstituted oxanilides and mixtures of o-and p-ethoxydisubstituted oxanilides.
8. 2-(2-Hydroxy>ahenyl)-1 3 5-triazines for example 2,4,6-tris(2-hydraxy-4-octyloxy-phenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octylaxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.
Light stabilisers of classes 1, 6 and 8 are preferred.
The addition of a mixture of a UV absorber of classes 1, 2, 3, 4, 7 and 8, preferably 1 and 8, together with a sterically hindered amine, far example of class 6 above, is particularly effective.
The amount of light stabiliser, or the sum of the light stabilisers, used is preferably 0.1 to % by weight, based on the solids content.
The top coat may further contain conventional additives of coating technology, for example levelling agents, thixotropic agents, flame retardants, antioxidants or soluble dyes.
The application of the top coat is made by conventional techniques of wood coating, for example by spreading, spraying or impregnating.
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The top coat can be applied in several coats so that it has a sufficient layer thickness. How thick the top coat shall be will depend on the intended end use.
The following Examples illustrate the invention in detail. Parts and percentages are by weight.
The following stabilisers are used in the Examples:
AO-1 octadecyl-(3-(3,5-di-tart-butyl-4-hydroxyphenyl)propionate AO-2 [i-(3,S-di-tart-butyl-4-hydroxyphenyl)propionate of pentaerythritol AO-3 bis[(3-(3,5-di-tart-butyl-4-hydroxyphenyl)propionate] of triethylene glycol AO-4 2,4,6-iris(~,5-di-tart-butyl-4-hydroxybenzyl)1,x,5-trimethylbenzene AO-S bis[[i-bis(3-tent-butyl-4-hydroxyphenyl)butyrate] of ethylene glycol AO-6 bis(2-hydroxy-3-tart-butyl-5-methylphenyl)methane LS-1 j3-[3-(benzotriazol-2-yl)-4-hydroxy-5-tent-butylphenyl]propionate of polyethylene glycol 300 LS-2 bis(1,2,2,6,6-pentamethylpiperid-4-yl)sebacate P-1 iris(2,4-di-tart-butylphenyl)phosphite Example 1 An undercoat is prepared from 27 parts of an alkyd resin (Jagalyd Antihydro~, E. Jager KG, 60 % solution in white spirit) .
1 part of an accelerator (Antihydro Trockner~, E. Jager KG) 3 parts of 2-ethoxyethanol 0.5 part of an anti-skinning agent (Ascinin~ P, Bayer AG) of »~x~~~
In specific cases it may be useful to use two or more antioxidants.
The undercoat shall penetrate the surface of the wood, and should therefore be of relatively low viscosity. In the simplest case, the undercoat is a solution of the antioxidant in an organic solvent. Exemplary of useful solvents for the purpose are aliphatic hydrocarbons such as specific petroleum fractions. Further suitable solvents are aromatic hydrocarbons such as toluene or xylene; alcohols such as methanol, ethanol, isopropanol or butanol; esters such as ethyl acetate or butyl acetate; or ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone. These solvents evaporate at room temperature and therefore do not remain in the wood. It is, however, also possible to add high boiling liquids which remain in the wood, for example higher alkanols, glycols, glycol ethers, glycol esters or polyglycols. The undercoat may also contain a binder conventionaliy used for protective wood coatings. Exemplary of suitable binders are alkyd resins and modified alkyd resins, autocrosslinking or non-autocrosslinking acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose or mixtures thereof.
The undercoat may also contain one or more phosphates which synergise the action of the antioxidants. Illustrative examples of such phosphates are:
triphenyl phosphate, diphenylalkyl phosphate, phenyldialkyl phosphate, tris(nonylphenyl) phosphate, trilauryl phosphate, trioctadecyl phosphate, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphate, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tent-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite.
Tris-(2,4-di-tv;rt-butylphenyl) phosphate is particularly preferred.
The undercoat may also contain preservatives such as fungicides or insecticides.
Exemplary of useful fungicides are tributyltin oxide, phenylmercury salts, copper naphthenate, 1-chloronaphthalene or pentachlorophenol. Exemplary of useful insecticides are DDT, dieldrin, lindane, parathion or phoxime.
Further ingredients which may be present in the undercoat are minor amounts of accelerators (hardeners) for the binders, dyes or pigments.
The undercoat consists mainly of the solvent and contains typically 0.05 to 10 %, preferably 0.1 to 5 %, of the antioxidant. It can further contain 0.1 to 5 %
by weight of a phosphite.
The undercoat can be applied to the wood by conventional techniques, for example by impregnating, spreading or spraying.
The undercoat may also be an aqueous coating. Instead of the organic solvent, the vehicle may then consist of water or a mixture of water and a water-soluble organic solvent. The antioxidant and the other components may be dissolved or dispersed in this vehicle.
Any coating composition suitable for coating wood may be used as top coat. It will normally contain a binder, dissolved or dispersed in an organic solvent or in water or a mixture of water and solvent. The binder may typically be a surface coating resin which dries in the air or hardens at room temperature. Exemplary of such binders are nitrocellulose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, and especially alkyd resins.
The binder may also be a mixture of different surface coating resins. Provided the binders are curable binders, they are normally used together with the hardener and/or accelerator.
Typical examples of organic solvents which may suitably be used for the coating compositions are aliphatic, aromatic or cycloaliphatic hydrocarbons, alcohols, esters, ketones or chlorinated hydrocarbons.
Water/solvent mixtures are typically mixtures of water and lower alcohols, glycols or glycol ethers.
The top coat may also be a radiation-curable, solvent-free formulation of photopolymerisable compounds. Illustrative examples are mixtures of acrylates or methacrylates, unsaturated polyester/styrene mixtures or mixtures of other ethylenically unsaturated monomers or oligomers.
The top coat may contain a soluble dye and/or a pigment and/or a filler. The pigment may be an organic, inorganic or metallic pigment. The filler may be typically kaolin, calcium carbonate or aluminium silicate. Preferably the top coat is a clear varnish, i.e. it contains no undissolved components.
~\
-g-Although the top coat which contains the antioxidant affords good protection against light, it is advantageous to add a light stabiliser to the top coat.111ustrative examples of suitable light stabilisers are the following compounds:
1. 2-(2'-Hydroxvphenyl)benzotriazoles for example the 5'-methyl, 3',5'-di-tert-butyl, 5'-tert-butyl, 5'-(1,1,3,3-tetramethylbutyl), 5-chloro-3',5'-di-tert-butyl, 5-chloro-3'-tert-butyl-5'-methyl, 3'-sec- butyl-5'-tert-butyl, 4'-octoxy, 3',5'-di-tert-amyl and 3',5'-bis(a,a-dimethylbenzyl) derivative, the octyl ester of 3-(5-chlorobenzotriazol-2-yl)-4-hydroxy-5-tert-butylphenylpropionic acid or the polyglycol 300 ester of 3-(benzo-triazol-2-yl)-4-hydroxy-5-tert-butylphenylpropionic acid.
2. 2-Hydrox benzophenones for example the 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivative.
3. Esters of substituted and unsubstituted benzoic acids for example, 4-tent-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tent-butylbenzoyl)-resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxy- benzoate and hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate.
4Acrylates, for example ethyl a-cyano-~i,~3-diphenylacrylate, isooctyl a-cyano-(3,(3-diphenylacrylate, methyl a-carbomethoxycinnamate, methyl a-cyano-~i-methyl-p-methoxy-cinnamate, butyl a-cyano-(3-methyl-p-methoxy- cinnamate, methyl a-carbo-methoxy-p-methoxycinnamate and N-(p-carbomethoxy-~3-cyanovinyl)-2-methylindoline.
5. Nickel compounds for example nickel complexes of 2,2'-thio-bis(4-(1,1,3,3-tetra-methylbutyl)phenol], such as the 1:1 or 1:2 complex, with, or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyl-dithiocarbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzyl-phosphonic acid monoalkyl esters, e.g. of the methyl or ethyl ester, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methyl-phenyl undecyl ketoneoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands. -6. Sterically hindered amines, for example bis(2,2,6,6-tetramethylpiperidyl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) ~~~~,~5 n-butyl-3,5-di-tert-butyl-4-hydroxy-benzylmalonate, the condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the condensation product of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butane-tetraoate, 1,1'-(1,2-ethanediyl)bis-(3,3,5,5-tetramethylpipexazinone).
7. Oxalvl diamides for example 4,4'-dioctyloxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butaxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxalamide, 2-ethoxy-5-tert-butyl-2'-ethyloxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide and mixtures of ortho- and para-methoxy-disubstituted oxanilides and mixtures of o-and p-ethoxydisubstituted oxanilides.
8. 2-(2-Hydroxy>ahenyl)-1 3 5-triazines for example 2,4,6-tris(2-hydraxy-4-octyloxy-phenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octylaxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxy-phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.
Light stabilisers of classes 1, 6 and 8 are preferred.
The addition of a mixture of a UV absorber of classes 1, 2, 3, 4, 7 and 8, preferably 1 and 8, together with a sterically hindered amine, far example of class 6 above, is particularly effective.
The amount of light stabiliser, or the sum of the light stabilisers, used is preferably 0.1 to % by weight, based on the solids content.
The top coat may further contain conventional additives of coating technology, for example levelling agents, thixotropic agents, flame retardants, antioxidants or soluble dyes.
The application of the top coat is made by conventional techniques of wood coating, for example by spreading, spraying or impregnating.
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The top coat can be applied in several coats so that it has a sufficient layer thickness. How thick the top coat shall be will depend on the intended end use.
The following Examples illustrate the invention in detail. Parts and percentages are by weight.
The following stabilisers are used in the Examples:
AO-1 octadecyl-(3-(3,5-di-tart-butyl-4-hydroxyphenyl)propionate AO-2 [i-(3,S-di-tart-butyl-4-hydroxyphenyl)propionate of pentaerythritol AO-3 bis[(3-(3,5-di-tart-butyl-4-hydroxyphenyl)propionate] of triethylene glycol AO-4 2,4,6-iris(~,5-di-tart-butyl-4-hydroxybenzyl)1,x,5-trimethylbenzene AO-S bis[[i-bis(3-tent-butyl-4-hydroxyphenyl)butyrate] of ethylene glycol AO-6 bis(2-hydroxy-3-tart-butyl-5-methylphenyl)methane LS-1 j3-[3-(benzotriazol-2-yl)-4-hydroxy-5-tent-butylphenyl]propionate of polyethylene glycol 300 LS-2 bis(1,2,2,6,6-pentamethylpiperid-4-yl)sebacate P-1 iris(2,4-di-tart-butylphenyl)phosphite Example 1 An undercoat is prepared from 27 parts of an alkyd resin (Jagalyd Antihydro~, E. Jager KG, 60 % solution in white spirit) .
1 part of an accelerator (Antihydro Trockner~, E. Jager KG) 3 parts of 2-ethoxyethanol 0.5 part of an anti-skinning agent (Ascinin~ P, Bayer AG) of »~x~~~
1.3 parts of a preservative (Traetex~ 293, Acima AG) 67.2 parts of white spirit.
This undercoat has a solids content of ca. 17 %. To this undercoat is added a solution of each of the antioxidants listed in Table 1 in 10 parts of xylene.
The undercoat is applied with a brush to pinewood boards (30x10x1.5 cm) and dried for 24 hours at room temperature.
The top coat is an alkyd resin based glaze of the following composition:
53 parts of an alkyd resin as 60% solution in white spirit (Jagalyd~
Antihydro) 11 parts of a thixotropic agent as 50% solution in white spirit (Jagalyd~
Antihydro Thix N) 1.9 parts of an accelerator (Antihydro Trockner ~, Jager) 33.4 parts of white spirit K 60 0.3 part of an anti-skinning agent (Ascinin~ P, Bayer AG) 0.4 part of a preservative (Exkin~ II, Servo BV) This glaze contains no pigment and has a solids content (binder) of ca. 38 %.
If the top coat contains light stabilisers, these are predissolved in a small amount of xylene.
The top coat is applied with a brush in three layers to the boaxds treated with the undercoat. Between the application of each layer, the specimen is allowed to dry for 24 hours at room temperature.
The specimens are exposed to weathering near Zurich in the open at 45°
south. The surface gloss and fungus infestation of the surface are assessed after 11 months.
This undercoat has a solids content of ca. 17 %. To this undercoat is added a solution of each of the antioxidants listed in Table 1 in 10 parts of xylene.
The undercoat is applied with a brush to pinewood boards (30x10x1.5 cm) and dried for 24 hours at room temperature.
The top coat is an alkyd resin based glaze of the following composition:
53 parts of an alkyd resin as 60% solution in white spirit (Jagalyd~
Antihydro) 11 parts of a thixotropic agent as 50% solution in white spirit (Jagalyd~
Antihydro Thix N) 1.9 parts of an accelerator (Antihydro Trockner ~, Jager) 33.4 parts of white spirit K 60 0.3 part of an anti-skinning agent (Ascinin~ P, Bayer AG) 0.4 part of a preservative (Exkin~ II, Servo BV) This glaze contains no pigment and has a solids content (binder) of ca. 38 %.
If the top coat contains light stabilisers, these are predissolved in a small amount of xylene.
The top coat is applied with a brush in three layers to the boaxds treated with the undercoat. Between the application of each layer, the specimen is allowed to dry for 24 hours at room temperature.
The specimens are exposed to weathering near Zurich in the open at 45°
south. The surface gloss and fungus infestation of the surface are assessed after 11 months.
Table 1 Antioxidant Light stabiliser60 glossfungus infestation in the in the top coat on the surface undercoat t~ 1>
none none no longer100 %
measurable none 1 % LS-1 40 % 70 %
1 % LS-2 1 % AO-1 none 73 % 20 %
1 % AO-1 1 % LS-1 73 % 5 %
1 % LS-2 1) Amount based on solids content of the coat Example 2 An undercoat (impregnation) is prepared from 2 parts of an alkyd resin (Jagalyd~ Antihydro, 60% solution in white spirit) 1 part of accelerator (Jagalyd~ Antihydro Trockner) 3 parts of 2-ethoxyethanol 0.2 part of an anti-skinning agent (Luactim~ M, BASF AG) 1.3 parts of a preservative (Traetex~ 293, Acima AG) 52:5 parts of white spirit 1~5 parts of xylene.
This undercoat has a solids content of ca. 17 %. To the undercoat is added a solution of each of the antioxidants listed in Table 2 in an amount of 1 %, based on solids (= 0.17 part, based on the undercoat).
The undercoat is applied with a brush to pinewood boards and dried for 24 hours at room temperature. The glaze described in Example 1 is used as top coat and is applied in 3 layers with a brush as described in Example 1.
The specimens are exposed to weathering in the open for 4.5 months in Basel at 45° south.
none none no longer100 %
measurable none 1 % LS-1 40 % 70 %
1 % LS-2 1 % AO-1 none 73 % 20 %
1 % AO-1 1 % LS-1 73 % 5 %
1 % LS-2 1) Amount based on solids content of the coat Example 2 An undercoat (impregnation) is prepared from 2 parts of an alkyd resin (Jagalyd~ Antihydro, 60% solution in white spirit) 1 part of accelerator (Jagalyd~ Antihydro Trockner) 3 parts of 2-ethoxyethanol 0.2 part of an anti-skinning agent (Luactim~ M, BASF AG) 1.3 parts of a preservative (Traetex~ 293, Acima AG) 52:5 parts of white spirit 1~5 parts of xylene.
This undercoat has a solids content of ca. 17 %. To the undercoat is added a solution of each of the antioxidants listed in Table 2 in an amount of 1 %, based on solids (= 0.17 part, based on the undercoat).
The undercoat is applied with a brush to pinewood boards and dried for 24 hours at room temperature. The glaze described in Example 1 is used as top coat and is applied in 3 layers with a brush as described in Example 1.
The specimens are exposed to weathering in the open for 4.5 months in Basel at 45° south.
Before and after weathering, the Yellowness Index (YI) of the surface of the specimens is measured in accordance with ASTM D 1 925. The increase in the YI after weathering is indicated in Table 2.
Table 2 Antioxidant Increase in the YI after in the undercoat *~ 4.5 months weathering none 38.5 1 % AO-2 32.5 1 % AO-3 33.2 0.5 % AO-2 + 0.5 % P-1 34.2 0.5%AO-4+0.5%P-1 35.2 *> Amount based on the solids content of the undercoat Example 3 A 0.5 % solution of the antioxidant in xylene is used as undercoat (impregnation). This undercoat is applied with a brush to the wood and then the specimens are dried for 24 hours at room temperature.
The glaze described in Example 1 is used as top coat and applied as in Example 1.
The specimens are exposed to weathering in the open for 4.5 months in Basel at 45° south.
The Yellowness Index (YI) is measured before and after weathering.
Table 2 Antioxidant Increase in the YI after in the undercoat *~ 4.5 months weathering none 38.5 1 % AO-2 32.5 1 % AO-3 33.2 0.5 % AO-2 + 0.5 % P-1 34.2 0.5%AO-4+0.5%P-1 35.2 *> Amount based on the solids content of the undercoat Example 3 A 0.5 % solution of the antioxidant in xylene is used as undercoat (impregnation). This undercoat is applied with a brush to the wood and then the specimens are dried for 24 hours at room temperature.
The glaze described in Example 1 is used as top coat and applied as in Example 1.
The specimens are exposed to weathering in the open for 4.5 months in Basel at 45° south.
The Yellowness Index (YI) is measured before and after weathering.
Table 3 Antioxidant in Increase in YI
the undercoat after 4.S months none 37.1 AO-2 32.8 AO-S 34.8 AO-6 33.4 AO-4 + O.S % P-1 32.1 Example 4 The undercoats and top coats described in Example 1 are used and applied to pinewood boards as described therein.
The specimens are exposed to weathering in a xenon light accelerated weathering test (cycle: 102 min. dry exposure, 18 min. sprinkling). The 60° gloss of the surface of the specimens is measured according to DIN 67 S30 at specific intervals. The results are reported in Table 4.
Antioxidant in % gloss after exposure time of the undercoat *> 262 h S33 h 1039 h 1302 h none 43 S1 22 10 1 % AO-1 S3 64 S9 . 30 1 % AO-3 62 68 70 51 *> Amount based on the solids content of the undercoat
the undercoat after 4.S months none 37.1 AO-2 32.8 AO-S 34.8 AO-6 33.4 AO-4 + O.S % P-1 32.1 Example 4 The undercoats and top coats described in Example 1 are used and applied to pinewood boards as described therein.
The specimens are exposed to weathering in a xenon light accelerated weathering test (cycle: 102 min. dry exposure, 18 min. sprinkling). The 60° gloss of the surface of the specimens is measured according to DIN 67 S30 at specific intervals. The results are reported in Table 4.
Antioxidant in % gloss after exposure time of the undercoat *> 262 h S33 h 1039 h 1302 h none 43 S1 22 10 1 % AO-1 S3 64 S9 . 30 1 % AO-3 62 68 70 51 *> Amount based on the solids content of the undercoat
Claims (21)
1. A method of protecting wood surfaces against light-induced degradation by treatment with a) an undercoat which penetrates tile surface of the wood and which does not contain a light stabiliser, said undercoat comprising an aqueous or organic solvent, or said solvent containing a binder selected from the group consisting of alkyd resins, modified alkyd resins, acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose resins and mixtures thereof, and b) one or more top coats, comprising a resin selected from the group consisting of nitrocellulose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, alkyd resins and mixtures thereof, said undercoat containing 0.05 to 10 % by weight of at least one antioxidant of the type of the sterically hindered phenols.
2. A method according to claim 1 wherein the antioxidant is a compound which contains at least one group of formula I
wherein R is hydrogen, methyl or tert-butyl.
wherein R is hydrogen, methyl or tert-butyl.
3. A process according to claim 2, wherein the antioxidant contains a group of formula I, wherein R is tert-butyl.
4. A process according to claim 1, wherein the antioxidant is an ester of b-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.
5. A process according to claim 4, wherein the antioxidant is a compound of formula II
wherein n is 1, 2 or 4 and, when n = 1, R1 is C8H17, and when n = 2, R1 is -(CH2)6- or -CH2CH2OCH2CH2OCH2CH2-, and, when n = 4, R1 is ---(CH2)4C.
wherein n is 1, 2 or 4 and, when n = 1, R1 is C8H17, and when n = 2, R1 is -(CH2)6- or -CH2CH2OCH2CH2OCH2CH2-, and, when n = 4, R1 is ---(CH2)4C.
6. A process according to claim 1, wherein the antioxidant is a compound of formula III
wherein R2 is hydrogen, methyl or tert-butyl.
wherein R2 is hydrogen, methyl or tert-butyl.
7. A process according to claim 6, wherein R2 is tert-butyl.
8. A process according to claim 1, wherein the antioxidant is a compound of formulaIV
wherein R3 is a group
wherein R3 is a group
9. A process according to claim 1, wherein the antioxidant is a compound of formulaV
wherein either m is 1 and R4 is methyl, or m is 2 and R4 is -CH2CH2-.
wherein either m is 1 and R4 is methyl, or m is 2 and R4 is -CH2CH2-.
10. A process according to claim 1, wherein the antioxidant is a compound of formulaVI
wherein R5 and R10 are hydrogen or tert-butyl, R6 and R9 are hydrogen or methyl, R7 is hydrogen or methyl and R8 is hydrogen or C1-C4alkyl.
wherein R5 and R10 are hydrogen or tert-butyl, R6 and R9 are hydrogen or methyl, R7 is hydrogen or methyl and R8 is hydrogen or C1-C4alkyl.
11. A process according to claim 1, wherein the antioxidant is 3,5-di-tert-butyl-4-hydroxytolu-ene.
12. A process according to claim 1, wherein the undercoat contains a binder and/or a high boiling liquid, selected from the group consisting of the higher alkanols, glycols, glycol ethers, glycol esters,and polygylcols, or a mixture thereof.
13. A process according to claim 1, wherein the undercoat contains a phosphite.
14. A process according to claim 1, wherein the undercoat contains tris(2,4-di-tert-butylphenyl)phosphite.
15. A process according to claim 1, wherein the undercoat contains a preservative.
16. A process according to claim 1, wherein the top coat is a clear varnish.
17. A process according to claim 1, wherein the top coat contains an alkyd resin based binder.
18. A process according to claim 1, wherein the top coat contains one or more light stabilisers.
19. A process according to claim 1, wherein the top coat contains a UV
absorber and a sterically hindered amine as light stabilisers.
absorber and a sterically hindered amine as light stabilisers.
20. A protective coating for wood comprising a) an undercoat which penetrates the surface of the wood and which does not contain a light stabiliser, said undercoat comprising an aqueous or organic solvent, or said solvent containgin a binder selected from the group consisting of alkyd resins, modified alkyd resins, acrylic resins, polyester resins, drying oils, phenolic resins, nitrocellulose resins and mixtures thereof, and b) one or more top coats, comprising a resin selected from the group consisting of nitrocellulose, polyvinyl acetate, polyvinyl chloride, unsaturated polyester resins, polyacrylates, polyurethanes, epoxy resins, phenolic resins, alkyd resins and mixtures thereof, said undercoat containing 0.05 to 10% by weight of at least one antioxidant of the type of the sterically hindered phenols.
21. A protective coating for wood, wherein the undercoat is a solution of a phenolic antioxidant in an organic solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH265/90-0 | 1990-01-29 | ||
| CH26590 | 1990-01-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2034952A1 CA2034952A1 (en) | 1991-07-30 |
| CA2034952C true CA2034952C (en) | 2001-07-03 |
Family
ID=4183070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002034952A Expired - Fee Related CA2034952C (en) | 1990-01-29 | 1991-01-25 | Protective coating for wood against damage by light containing undercoating comprising sterically hindered phenols |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0440580B1 (en) |
| JP (1) | JP3143751B2 (en) |
| CA (1) | CA2034952C (en) |
| DE (1) | DE59104830D1 (en) |
| ES (1) | ES2069258T3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005046345B4 (en) * | 2004-09-21 | 2009-08-06 | Institut für Holztechnologie Dresden gGmbH | Wood materials, process for their preparation |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI93431C (en) * | 1990-12-05 | 1995-04-10 | Aho Jyrki | Parquet structure and process for its preparation |
| EP0897958B1 (en) * | 1997-08-19 | 2003-06-18 | Ciba SC Holding AG | Stabilisers for powder coatings |
| DE10030658C1 (en) | 2000-06-23 | 2002-01-03 | Trespa Int Bv | Flame retardant resin coating |
| DE102005041214A1 (en) * | 2005-08-31 | 2007-03-01 | Votteler Lackfabrik Gmbh & Co. Kg | Production of veneered mouldings involves press-moulding a combination of base material and a face veneer coated with a coherent layer of viscous impregnating material which hardens during moulding |
| ATE428549T1 (en) * | 2005-11-04 | 2009-05-15 | Ciba Holding Inc | COLOR STABILIZATION OF CORK AND DYED WOODS THROUGH THE COMBINED USE OF INORGANIC AND ORGANIC UV ABSORBERS |
| EP2181818A3 (en) | 2008-10-28 | 2012-08-22 | IHD Institut für Holztechnologie Dresden gGmbH | Method for manufacturing wood fibre substances and wood fibre substances with lower emissions of volatile VOC |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3285855A (en) * | 1965-03-11 | 1966-11-15 | Geigy Chem Corp | Stabilization of organic material with esters containing an alkylhydroxy-phenyl group |
| GB1419768A (en) * | 1972-04-27 | 1975-12-31 | Ici Ltd | Polyurethanes |
-
1991
- 1991-01-21 EP EP91810047A patent/EP0440580B1/en not_active Expired - Lifetime
- 1991-01-21 ES ES91810047T patent/ES2069258T3/en not_active Expired - Lifetime
- 1991-01-21 DE DE59104830T patent/DE59104830D1/en not_active Expired - Fee Related
- 1991-01-25 CA CA002034952A patent/CA2034952C/en not_active Expired - Fee Related
- 1991-01-29 JP JP03047269A patent/JP3143751B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005046345B4 (en) * | 2004-09-21 | 2009-08-06 | Institut für Holztechnologie Dresden gGmbH | Wood materials, process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59104830D1 (en) | 1995-04-13 |
| JPH05253539A (en) | 1993-10-05 |
| EP0440580B1 (en) | 1995-03-08 |
| JP3143751B2 (en) | 2001-03-07 |
| EP0440580A3 (en) | 1992-07-01 |
| EP0440580A2 (en) | 1991-08-07 |
| CA2034952A1 (en) | 1991-07-30 |
| ES2069258T3 (en) | 1995-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |