AU756097B2 - Stabilization of wood substrates - Google Patents
Stabilization of wood substrates Download PDFInfo
- Publication number
- AU756097B2 AU756097B2 AU21318/99A AU2131899A AU756097B2 AU 756097 B2 AU756097 B2 AU 756097B2 AU 21318/99 A AU21318/99 A AU 21318/99A AU 2131899 A AU2131899 A AU 2131899A AU 756097 B2 AU756097 B2 AU 756097B2
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- hydrogen
- formula
- 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.)
- Ceased
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- 239000002023 wood Substances 0.000 title claims abstract description 37
- 230000006641 stabilisation Effects 0.000 title description 6
- 238000011105 stabilization Methods 0.000 title description 6
- 239000000758 substrate Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 293
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 187
- -1 amine compound Chemical class 0.000 claims abstract description 95
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 238000005470 impregnation Methods 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000015556 catabolic process Effects 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 8
- 238000006731 degradation reaction Methods 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 150000001449 anionic compounds Chemical group 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 150000002891 organic anions Chemical group 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 239000001257 hydrogen Substances 0.000 claims description 99
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 57
- 125000002947 alkylene group Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000011230 binding agent Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 229920000180 alkyd Polymers 0.000 claims description 7
- 150000007942 carboxylates Chemical group 0.000 claims description 7
- 150000002334 glycols Chemical class 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 125000006839 xylylene group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 claims description 5
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229940116351 sebacate Drugs 0.000 claims description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 5
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- QPCDCPDFJACHGM-UHFFFAOYSA-K pentetate(3-) Chemical compound OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QPCDCPDFJACHGM-UHFFFAOYSA-K 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical group OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical group [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000020 Nitrocellulose Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 229920001220 nitrocellulos Polymers 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- QDNPLNOHUNPYHZ-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidine Chemical compound CCCOC1CC(C)(C)N(O)C(C)(C)C1 QDNPLNOHUNPYHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- XQEZPIIANZJBMP-UHFFFAOYSA-N hydrogen sulfate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound OS([O-])(=O)=O.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1 XQEZPIIANZJBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 229910052760 oxygen Chemical group 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 229920001225 polyester resin Polymers 0.000 claims description 2
- 239000004645 polyester resin Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 239000004711 α-olefin Substances 0.000 claims description 2
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 claims 3
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- OEXWWDYOBBQCKD-UHFFFAOYSA-N SSSSSS Chemical compound SSSSSS OEXWWDYOBBQCKD-UHFFFAOYSA-N 0.000 claims 2
- YYTYIUAYFBFKHX-UHFFFAOYSA-N n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 YYTYIUAYFBFKHX-UHFFFAOYSA-N 0.000 claims 2
- OMLXPSWZYGQPCR-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-one;acetate Chemical compound CC([O-])=O.CC1(C)CC(=O)CC(C)(C)[NH+]1O OMLXPSWZYGQPCR-UHFFFAOYSA-N 0.000 claims 1
- KRNWYBIEWUXCOB-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidine Chemical compound COC1CC(C)(C)N(O)C(C)(C)C1 KRNWYBIEWUXCOB-UHFFFAOYSA-N 0.000 claims 1
- WQFZLUAKGBOQEN-UHFFFAOYSA-N 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.CC1(C)CC(=O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O WQFZLUAKGBOQEN-UHFFFAOYSA-N 0.000 claims 1
- VXBXRPKTLUBAHQ-UHFFFAOYSA-N 2-[bis(carboxylatomethyl)amino]acetate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CN(CC([O-])=O)CC([O-])=O VXBXRPKTLUBAHQ-UHFFFAOYSA-N 0.000 claims 1
- ZGDIZLYJGRHLDL-UHFFFAOYSA-N 2-[bis(carboxylatomethyl)amino]acetate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound [O-]C(=O)CN(CC([O-])=O)CC([O-])=O.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1 ZGDIZLYJGRHLDL-UHFFFAOYSA-N 0.000 claims 1
- 101100515513 Arabidopsis thaliana XI-E gene Proteins 0.000 claims 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
- 101800001194 Crustacean hyperglycemic hormone 2 Proteins 0.000 claims 1
- 229910017711 NHRa Inorganic materials 0.000 claims 1
- FSLJQBWNDCKEHA-UHFFFAOYSA-N S.SS Chemical compound S.SS FSLJQBWNDCKEHA-UHFFFAOYSA-N 0.000 claims 1
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 31
- 150000001412 amines Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 10
- 239000004611 light stabiliser Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000012964 benzotriazole Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 7
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 7
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
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- 230000000052 comparative effect Effects 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
- 229920005610 lignin Polymers 0.000 description 5
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 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 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
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- 239000013008 thixotropic agent Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- B27K3/36—Aliphatic compounds
-
- 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
- C09D15/00—Woodstains
-
- 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
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
- B27K3/153—Without in-situ polymerisation, condensation, or cross-linking reactions
-
- 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
- B27K3/343—Heterocyclic compounds
-
- 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
- B27K3/38—Aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
-
- 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
- B27K2240/00—Purpose of the treatment
- B27K2240/90—UV-protection
-
- 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
- B27K5/00—Treating of wood not provided for in groups B27K1/00, B27K3/00
- B27K5/02—Staining or dyeing wood; Bleaching wood
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Forests & Forestry (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Stringed Musical Instruments (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE98810238 | 1998-03-19 | ||
| EP98810238 | 1998-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2131899A AU2131899A (en) | 1999-09-30 |
| AU756097B2 true AU756097B2 (en) | 2003-01-02 |
Family
ID=8236000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU21318/99A Ceased AU756097B2 (en) | 1998-03-19 | 1999-03-19 | Stabilization of wood substrates |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6187387B1 (https=) |
| EP (1) | EP0943665B1 (https=) |
| JP (1) | JP4689778B2 (https=) |
| KR (1) | KR100550811B1 (https=) |
| CN (1) | CN1106919C (https=) |
| AT (1) | ATE253621T1 (https=) |
| AU (1) | AU756097B2 (https=) |
| BR (1) | BR9901022B1 (https=) |
| CA (1) | CA2265990C (https=) |
| DE (1) | DE69912502T2 (https=) |
| DK (1) | DK0943665T3 (https=) |
| ES (1) | ES2209368T3 (https=) |
| TW (1) | TWI224995B (https=) |
| ZA (1) | ZA992175B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030159294A1 (en) * | 1998-01-21 | 2003-08-28 | Whittenbury Clive G. | Laser-assisted joining device |
| JP4259639B2 (ja) * | 1998-04-01 | 2009-04-30 | 株式会社Adeka | 自動車外装用熱硬化性合成樹脂塗料組成物 |
| TW514581B (en) | 1999-09-02 | 2002-12-21 | Ciba Sc Holding Ag | A method of protecting wood against light-induced degradation by treatment with an impregnation which penetrates the surface of the wood |
| US6989449B1 (en) * | 1999-09-15 | 2006-01-24 | Ciba Specialty Chemicals Corporation | Chlorohydrin and cationic compounds having high affinity for pulp or paper |
| PL205847B1 (pl) | 2000-05-11 | 2010-06-30 | Ciba Sc Holding Ag | Sposób bejcowania drewna, wodna bejca drewna, zastosowanie stabilizatora barwnika oraz zastosowanie wodnej bejcy drewna |
| NZ509133A (en) * | 2000-12-22 | 2003-08-29 | Nz Forest Research Inst Ltd | Coating wood surfaces first by delignification followed with a transparent varnish |
| US6527914B1 (en) | 2002-01-30 | 2003-03-04 | Ondeo Nalco Company | Method of enhancing brightness and brightness stability of paper made with mechanical pulp |
| JP4594727B2 (ja) * | 2002-05-02 | 2010-12-08 | チバ ホールディング インコーポレーテッド | 安定化ボディケア製品、家庭用品、織物材料及び織物 |
| EP1507826A4 (en) | 2002-05-17 | 2007-11-07 | Othera Pharmaceuticals Inc | IMPROVING THE EVOLUTION OF CATARACTS AND OTHER OPHTHALMIC DISEASES |
| DE10236741A1 (de) * | 2002-08-09 | 2004-02-19 | Remmers Baustofftechnik Gmbh | Stabilisierung von Polymeren gegenüber lichtinduziertem Abbau |
| ITBO20020599A1 (it) * | 2002-09-20 | 2004-03-21 | Arch Coatings Italia Spa Ora Arch Sayerlack | Vernice, procedimento di preparazione e relativo impiego su di un supporto legnoso. |
| KR100517498B1 (ko) * | 2002-09-28 | 2005-09-28 | 삼성전자주식회사 | 내광성 착색제 및 이를 포함하는 잉크젯 프린터용 잉크조성물 |
| DE10246400A1 (de) * | 2002-10-04 | 2004-08-05 | Georg-August-Universität Göttingen | Verfahren zur Verbesserung der Oberflächenhärte eines Holzkörpers mit einer wässrigen Lösung eines Imprägniermittels |
| DE10246401A1 (de) * | 2002-10-04 | 2004-08-05 | Georg-August-Universität Göttingen | Verfahren zur Verbesserung der Dauerhaftigkeit, Dimensionsstabilität und Oberflächenhärte eines Holzkörpers |
| NZ523249A (en) | 2002-12-16 | 2005-04-29 | Mattersmiths Holdings Ltd | Method of delivering compositions to substrates |
| US7825134B2 (en) | 2003-05-19 | 2010-11-02 | Othera Holding, Inc. | Amelioration of cataracts, macular degeneration and other ophthalmic diseases |
| WO2005005114A1 (en) * | 2003-07-09 | 2005-01-20 | Ciba Specialty Chemicals Holding Inc. | Stabilization of wood with sterically hindered amine-n-oxyls or hydroxyls and transparent inorganic pigments |
| DE112006000348T5 (de) | 2005-02-15 | 2007-12-27 | Ciba Speciality Chemicals Holding Inc. | Stabilisierung von natürlichen Komposit- bzw. Verbundwerkstoffen |
| EP1954457B1 (en) * | 2005-11-04 | 2009-04-15 | Ciba Holding Inc. | Color stabilization of cork and colored woods by the combined use of inorganic and organic uv-absorbers |
| DE102006010347A1 (de) * | 2006-03-03 | 2007-09-06 | Degussa Gmbh | Polymerisationsinhibitor zur Stabilisierung von olefinisch ungesättigten Monomeren |
| FI20085953L (fi) * | 2008-10-09 | 2010-04-10 | Tikkurila Oy | Puun kyllästys |
| US8298675B2 (en) * | 2009-07-17 | 2012-10-30 | Honda Motor Co., Ltd. | Low gloss wood for interior trim |
| CN103911468B (zh) * | 2013-12-27 | 2015-06-03 | 苏州华策纺织科技有限公司 | 一种天然皮革处理剂 |
| SG11201703031PA (en) | 2014-10-14 | 2017-05-30 | Ecolab Usa Inc | Reducing polymer fouling and agglomeration in acrylate/methacrylate processes |
| AU2015215849B2 (en) * | 2014-11-24 | 2016-12-15 | Arch Wood Protection Pty Ltd | Improved wood preservative formulations |
| CA2979828C (en) | 2015-03-18 | 2023-08-29 | Ecolab Usa Inc. | The use of stable lipophilic hydroxylamine compounds for inhibiting polymerization of vinyl monomers |
| US9957209B2 (en) | 2015-03-31 | 2018-05-01 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| CA2982465C (en) | 2015-04-20 | 2024-05-14 | Ecolab Usa Inc. | Sterically hindered hydroquinones as antifoulants for unsaturated monomers |
| WO2017055247A1 (en) * | 2015-09-29 | 2017-04-06 | Teijin Aramid B.V. | Polyarylene fiber with improved hydrolytic stability |
| CN110352068A (zh) | 2016-12-02 | 2019-10-18 | 南加利福尼亚大学 | 合成的免疫受体及其使用方法 |
| US10563083B2 (en) | 2017-04-28 | 2020-02-18 | Bond Distributing, Ltd. | UV curable sealant composition and protector applied to wood and porous substrates |
| US12043756B2 (en) | 2017-04-28 | 2024-07-23 | Bond Distributing, Ltd. | Electron beam irradiation process and polymerizable stain applied to wood planking |
| CN108162112A (zh) * | 2017-12-08 | 2018-06-15 | 德华兔宝宝装饰新材股份有限公司 | 一种三元复配染料及采用该染料制备高色牢度单板层的方法 |
| JP2019177685A (ja) * | 2018-03-30 | 2019-10-17 | 大日本印刷株式会社 | 木質系部材 |
| US20220403201A1 (en) * | 2019-11-27 | 2022-12-22 | Swimc Llc | Low voc coatings including hyper-branched alkylated polymers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831134A (en) * | 1987-09-21 | 1989-05-16 | Ciba-Geigy Corporation | N-hydroxy hindered amine stabilizers |
| EP0434608A1 (en) * | 1989-12-05 | 1991-06-26 | Ciba-Geigy Ag | Stabilized organic material |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE39205B1 (en) * | 1973-04-19 | 1978-08-30 | Ciba Geigy Ag | New stabiliser system and its use for stabilising styrene polymers |
| CH589056A5 (https=) * | 1973-12-10 | 1977-06-30 | Ciba Geigy Ag | |
| US4590231A (en) * | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| EP0309401B2 (en) * | 1987-09-21 | 2002-06-05 | Ciba Specialty Chemicals Holding Inc. | Stabilization of coatings with N-hydroxy hindered amines |
| US5736597A (en) * | 1989-12-05 | 1998-04-07 | Ciba-Geigy Corporation | Stabilized organic material |
| DE4031279A1 (de) * | 1990-10-04 | 1992-04-09 | Basf Ag | Stabilisatoren enthaltende holzbeizen |
| IT1271711B (it) * | 1994-11-09 | 1997-06-04 | Ciba Geigy Spa | Derivati della 2,2,6,6-tetrametilpiperidina utili come stabilizzanti alla luce, al calore e all'ossidazione per materiali organici |
| TW401437B (en) * | 1995-02-10 | 2000-08-11 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
-
1999
- 1999-02-23 TW TW088102605A patent/TWI224995B/zh not_active IP Right Cessation
- 1999-03-10 AT AT99810213T patent/ATE253621T1/de active
- 1999-03-10 DE DE69912502T patent/DE69912502T2/de not_active Expired - Lifetime
- 1999-03-10 ES ES99810213T patent/ES2209368T3/es not_active Expired - Lifetime
- 1999-03-10 JP JP06325499A patent/JP4689778B2/ja not_active Expired - Fee Related
- 1999-03-10 EP EP99810213A patent/EP0943665B1/en not_active Expired - Lifetime
- 1999-03-10 DK DK99810213T patent/DK0943665T3/da active
- 1999-03-11 US US09/267,472 patent/US6187387B1/en not_active Expired - Lifetime
- 1999-03-17 CA CA002265990A patent/CA2265990C/en not_active Expired - Fee Related
- 1999-03-18 CN CN99105965A patent/CN1106919C/zh not_active Expired - Fee Related
- 1999-03-18 ZA ZA9902175A patent/ZA992175B/xx unknown
- 1999-03-18 KR KR1019990009143A patent/KR100550811B1/ko not_active Expired - Fee Related
- 1999-03-19 AU AU21318/99A patent/AU756097B2/en not_active Ceased
- 1999-03-19 BR BRPI9901022-4A patent/BR9901022B1/pt not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831134A (en) * | 1987-09-21 | 1989-05-16 | Ciba-Geigy Corporation | N-hydroxy hindered amine stabilizers |
| EP0434608A1 (en) * | 1989-12-05 | 1991-06-26 | Ciba-Geigy Ag | Stabilized organic material |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2209368T3 (es) | 2004-06-16 |
| CA2265990A1 (en) | 1999-09-19 |
| US6187387B1 (en) | 2001-02-13 |
| ATE253621T1 (de) | 2003-11-15 |
| EP0943665A1 (en) | 1999-09-22 |
| DK0943665T3 (da) | 2004-03-08 |
| BR9901022A (pt) | 1999-12-28 |
| JP4689778B2 (ja) | 2011-05-25 |
| AU2131899A (en) | 1999-09-30 |
| KR19990078005A (ko) | 1999-10-25 |
| CN1106919C (zh) | 2003-04-30 |
| CN1237501A (zh) | 1999-12-08 |
| EP0943665B1 (en) | 2003-11-05 |
| ZA992175B (en) | 1999-09-20 |
| JP2000025010A (ja) | 2000-01-25 |
| CA2265990C (en) | 2008-07-22 |
| BR9901022B1 (pt) | 2011-04-19 |
| DE69912502T2 (de) | 2004-09-23 |
| TWI224995B (en) | 2004-12-11 |
| KR100550811B1 (ko) | 2006-02-10 |
| DE69912502D1 (de) | 2003-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |