JP5580599B2 - 2−ヒドロキシフェニルトリアジンで紫外線安定化された色付きクリヤコーティング - Google Patents
2−ヒドロキシフェニルトリアジンで紫外線安定化された色付きクリヤコーティング Download PDFInfo
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- JP5580599B2 JP5580599B2 JP2009545127A JP2009545127A JP5580599B2 JP 5580599 B2 JP5580599 B2 JP 5580599B2 JP 2009545127 A JP2009545127 A JP 2009545127A JP 2009545127 A JP2009545127 A JP 2009545127A JP 5580599 B2 JP5580599 B2 JP 5580599B2
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- 238000000576 coating method Methods 0.000 title claims description 77
- 239000011248 coating agent Substances 0.000 title claims description 73
- HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 title claims description 26
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000000049 pigment Substances 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 47
- 239000008199 coating composition Substances 0.000 claims description 41
- 239000011230 binding agent Substances 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 239000006096 absorbing agent Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 17
- 239000011247 coating layer Substances 0.000 claims description 15
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 14
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 14
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
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- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 4
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 3
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- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 3
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 3
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 claims description 2
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
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- 239000001257 hydrogen Substances 0.000 description 21
- 125000002947 alkylene group Chemical group 0.000 description 18
- 239000003973 paint Substances 0.000 description 17
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- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005627 triarylcarbonium group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical class CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical class O=C([*])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
- 125000005065 undecenyl group Chemical class C(=CCCCCCCCCC)* 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
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical class O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
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- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
(a)少なくとも1種の2−ヒドロキシフェニルトリアジン紫外線吸収剤、
(b)キナクリドン、ジケト−ピロロ−ピロール、キナクリドン/ジケト−ピロロ−ピロール、イソインドリノン、フタロシアニン、BiV、ペリレン、アントラキノンレッド、インダントロンブルー、アゾメチンCu錯体、モノアゾNi錯体、キノフタロン、イソインドリンおよびナフトールAS、並びにこれらの混合物(例えば結晶混合物)および固溶体よりなる群から選択される少なくとも1種の顔料、および
(c)少なくとも1種のバインダー
を含む、色付きクリヤコーティング組成物に関する。
X、X’、YおよびY’は、同一または異なり、XおよびYに対する定義の通りであり;
R1は、水素、炭素原子数1〜24の直鎖状もしくは分岐状鎖アルキル、炭素原子数5〜12のシクロアルキル、炭素原子数7〜15のフェニルアルキル、ハロゲン、−SR3、−SOR3または−SO2R3;あるいは1〜3個のハロゲン、−R4、−OR5、−N(R5)2、−COR5、−COOR5、−OCOR5、−CN、−NO2、−SR5、−SOR5、−SO2R5または−P(O)(OR5)2、モルホリニル、ピペリジニル、2,2,6,6−テトラメチルピペリジニル、ピペラジニルまたはN−メチルピペリジニル基またはこれらの組合せで置換された該アルキル、該シクロアルキルまたは該フェニルアルキル;あるいは1〜4個のフェニレン、−O−、−NR5−、−CONR5−、−COO−、−OCO−または−CO基またはこれらの組合せで中断された該アルキルまたは該シクロアルキル;あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルまたは該シクロアルキルであり;
R1、R1’およびR1”は、同一または異なり、R1に対する定義の通りであり;
R2は、水素、炭素原子数1〜24の直鎖状もしくは分岐鎖のアルキル、または炭素原子数5〜12のシクロアルキル;あるいは1〜4個のハロゲン、エポキシ、グリシジルオキシ、フリルオキシ、−R4、−OR5、−N(R5)2、−CON(R5)2、−COR5、−COOR5、−OCOR5、−OCOC(R5)=C(R5)2、−C(R5)=CCOOR5、−CN、−NCO、または
R2、R2’およびR2”は、同一または異なり、R2に対する定義の通りであり;
R3は、炭素原子数1〜20のアルキル、炭素原子数3〜18のアルケニル、炭素原子数5〜12のシクロアルキル、炭素原子数7〜15のフェニルアルキル、炭素原子数6〜10のアリール、または1もしくは2個の炭素原子数1〜4のアルキルで置換された該アリールであり;
R4は、炭素原子数6〜10のアリール、あるいは1〜3個のハロゲン、炭素原子数1〜8のアルキル、炭素原子数1〜8のアルコキシまたはこれらの組合せで置換された該アリール;炭素原子数5〜12のシクロアルキル;炭素原子数7〜15のフェニルアルキル、あるいはフェニル環が1〜3個のハロゲン、炭素原子数1〜8のアルキル、炭素原子数1〜8のアルコキシまたはこれらの組合せで置換された該フェニルアルキル;あるいは炭素原子数2〜18の直鎖状もしくは分岐鎖のアルケニルであり;
R5は、R4と定義されるか;あるいはR5はまた、水素、または炭素原子数1〜24の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜24のアルケニルであるか;またはR5は、式:
Tは、水素、オキシル、ヒドロキシル、−OT1、炭素原子数1〜24のアルキル、1〜3個のヒドロキシで置換された該アルキル;ベンジルまたは炭素原子数2〜18のアルカノイルであり;
T1は、炭素原子数1〜24のアルキル、炭素原子数5〜12のシクロアルキル、炭素原子数2〜24のアルケニル、炭素原子数5〜12のシクロアルケニル、炭素原子数7〜15のフェニルアルキル、炭素原子数7〜12の飽和もしくは不飽和の二環もしくは三環系炭化水素基、または炭素原子数6〜10のアリール、または1〜3個の炭素原子数1〜4のアルキルで置換された該アリールであり;
R6は、炭素原子数1〜18の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜12の直鎖状もしくは分岐鎖のアルケニル、フェノキシ、炭素原子数1〜12のアルキルアミノ、炭素原子数6〜12のアリールアミノ、−R7COOHまたは−NH−R8−NCOであり;
R7は、炭素原子数2〜14のアルキレンまたはフェニレンであり;
R8は、炭素原子数2〜24のアルキレン、フェニレン、トリレン、ジフェニルメタンまたは基:
tは、0〜9であり;
Lは、炭素原子数1〜12の直鎖状もしくは分岐状アルキレン、炭素原子数5〜12のシクロアルキレン、またはシクロヘキシレンもしくはフェニレンで置換または中断されたアルキレンであるか;またはLは、ベンジリデンであるか;またはLは、−S−、−S−S−、−S−E−S−、−SO−、−SO2−、−SO−E−SO−、−SO2−E−SO2−、−CH2−NH−E−NH−CH2−または
Eは、炭素原子数2〜12のアルキレン、炭素原子数5〜12のシクロアルキレン、または炭素原子数5〜12のシクロアルキレンで中断もしくは停止されたアルキレンであり;
nは、2、3または4であり;
nが2である場合;Qは、炭素原子数2〜16の直鎖状もしくは分岐状アルキレン;または1〜3個のヒドロキシ基で置換された該アルキレン;または1〜3個の−CH=CH−もしくは−O−で中断された該アルキレン;または上述した基の組合せで置換および中断の両方がなされた該アルキレンであるか;またはQは、キシリレンもしくは基−CONH−R8−NHCO−、−CH2CH(OH)CH2O−R9−OCH2CH(OH)CH2−、−CO−R10−CO−、もしくは−(CH2)m−COO−R11−OOC−(CH2)m−(式中、mは1〜3である)であるか;またはQは、
R10は、炭素原子数2〜10のアルキレン、または1〜4個の−O−、−S−または−CH=CH−で中断された該アルキレンであるか;またはR10は、炭素原子数6〜12のアリーレンであり;
R11は、炭素原子数2〜20のアルキレン、または1〜8個の−O−で中断された該アルキレンであり;
nが3である場合、Qは、基−[(CH2)mCOO]3−R12(式中、mは1〜3であり、R12は、炭素原子数3〜12のアルカントリイルである)であり;
nが4である場合、Qは、基−[(CH2)mCOO]4−R13(式中、mは1〜3であり、R13は、炭素原子数4〜12のアルカンテトライルである)であり;
Z1は、式:
Z2は、式:
R14、R15、R16、R17、R18、R19、R20、R21、R22およびR23は、互いに独立に、水素、ヒドロキシ、シアノ、炭素原子数1〜20のアルキル、炭素原子数1〜20のアルコキシ、炭素原子数7〜15のフェニルアルキル、炭素原子数5〜12のシクロアルキル、炭素原子数5〜12のシクロアルコキシ、ハロゲン、炭素原子数1〜5のハロアルキル、スルホ、カルボキシ、炭素原子数2〜12のアシルアミノ、炭素原子数2〜12のアシルオキシ、炭素原子数2〜12のアルコキシカルボニル、またはアミノカルボニルであるか;あるいはR17とR18、またはR22とR23は、これらが結合したフェニル基と一緒になって、1〜3個の−O−または−NR5−で中断された環状基である)の基である]である。
R1は、水素であり;
R1’およびR1”は、R1に対する定義の通りであり;
R2は、水素、炭素原子数1〜24の直鎖状もしくは分岐鎖のアルキル;あるいは1〜4個の−R4、−OR5、−N(R5)2、−CON(R5)2、−COR5、−COOR5、−OCOR5、−OCOC(R5)=C(R5)2、−C(R5)=CCOOR5、またはこれらの組合せで置換された該アルキル;あるいは1〜4個の−O−、−NR5−、−CONR5−、−COO−、−OCO−、−CO−、−C(R5)=C(R5)COO−、−OCOC(R5)=C(R5)−、−C(R5)=C(R5)−、またはこれらの組合せで中断された該アルキル、あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルであるか;あるいはR2は、−COR6であり;
R2、R2’およびR2”は、同一または異なり、R2に対する定義の通りであり;
R4は、炭素原子数2〜18の直鎖状もしくは分岐鎖のアルケニルであり;
R5は、R4と定義されるか;あるいはR5はまた、水素、または炭素原子数1〜24の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜24のアルケニルであり;
R6は、炭素原子数1〜18の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜12の直鎖状もしくは分岐鎖のアルケニル、炭素原子数1〜12のアルキルアミノであり;
Z1は、式:
Z2は、式:
R14、R15、R16、R17、R18、R19、R20、R21、R22およびR23は、互いに独立に、水素、ヒドロキシ、炭素原子数1〜20のアルキル、炭素原子数1〜20のアルコキシ、カルボキシ、炭素原子数2〜12のアシルアミノ、炭素原子数2〜12のアシルオキシ、炭素原子数2〜12のアルコキシカルボニルまたはアミノカルボニルである)の基である]である。
R1は、水素であり;
R1’およびR1”は、R1に対する定義の通りであり;
R2は、水素、炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル;あるいは1または2個の−R4、−OR5、−COOR5、−OCOR5、−OCOC(R5)=C(R5)2、−C(R5)=CCOOR5、またはこれらの組合せで置換された該アルキル;あるいは1または2個の−O−、−COO−、−OCO−、またはこれらの組合せで中断された該アルキル、あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルであるか;あるいはR2は、−COR6であり;
R2、R2’およびR2”は、同一または異なり、R2に対する定義の通りであり;
R4は、炭素原子数2〜3の直鎖状もしくは分岐状鎖アルケニルであり;
R5は、R4と定義されるか;あるいはR5はまた、水素、または炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜3のアルケニルであり;
R6は、炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜3の直鎖状もしくは分岐鎖のアルケニルであり;
Z1は、式:
Z2は、式:
R14、R15、R16、R17、R18、R19、R20、R21、R22およびR23は、水素である)の基である]である。
R1は、水素であり;
R1’およびR1”は、R1に対する定義の通りであり;
R2は、水素、炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル;あるいは1または2個の−OR5、−COOR5、−OCOR5、−OCOC(R5)=C(R5)2、またはこれらの組合せで置換された該アルキル;あるいは1個の−O−、−COO−または−OCO−で中断された該アルキル、あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルであるか;あるいはR2は、−COR6であり;
R2、R2’およびR2”は、同一または異なり、R2に対する定義の通りであり;
R5は、水素、または炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル、炭素原子数2〜3のアルケニルであり;
R6は、炭素原子数2〜3の直鎖状もしくは分岐鎖のアルケニルであり;
Z1は、式:
Z2は、式:
R14、R15、R16、R17、R18、R19、R20、R21、R22およびR23は、水素である)の基である]である。
XおよびYは、独立に、フェニル、あるいは1〜2個の炭素原子数1のアルキルで置換された該フェニルであるか;あるいは独立に、Z1またはZ2であり;
R1は、水素であり;
R2は、炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル;あるいは1個の−OR5、−COOR5または−OCOR5で置換された該アルキル;あるいは1個の−O−、−COO−または−OCO−で中断された該アルキル、あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルであり;
R5は、水素、または炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキルであり;
Z1およびZ2は、前記定義の通りである)である。
R1は、水素であり;
R2は、炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキル;あるいは1個の−OR5または−COOR5で置換された該アルキル;あるいは1個の−O−または−COO−で中断された該アルキル、あるいは上述した基の組合せで置換および中断の両方がなされた該アルキルであり;
R5は、水素、または炭素原子数1〜15の直鎖状もしくは分岐鎖のアルキルであり;
Z1およびZ2は、前記定義の通りである)である。
1)G1=G2=CH(CH3)−COO−C8H17、G3=G4=H;
2)G1=G2=G3=CH(CH3)−COO−C8H17、G4=H;
3)G1=G2=G3=G4=CH(CH3)−COO−C8H17;
HPT−18 2−(2,4−ジヒドロキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、
HPT−19 2,4−ビス(2−ヒドロキシ−4−プロピルオキシフェニル)−6−(2,4−ジメチルフェニル)−1,3,5−トリアジン、
HPT−20 2−(2−ヒドロキシ−4−オクチルオキシフェニル)−4,6−ビス(4−メチルフェニル)−1,3,5−トリアジン、
HPT−21 2−(2−ヒドロキシ−4−ドデシルオキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、
HPT−22 2−(2−ヒドロキシ−4−トリデシルオキシフェニル)−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、
HPT−23 2−[2−ヒドロキシ−4−(2−ヒドロキシ−3−ブチルオキシプロポキシ)フェニル]−4,6−ビス(2,4−ジメチル)−1,3,5−トリアジン、
HPT−24 2−[2−ヒドロキシ−4−(2−ヒドロキシ−3−オクチルオキシプロピルオキシ)フェニル]−4,6−ビス(2,4−ジメチル)−1,3,5−トリアジン、
HPT−25 2−[2−ヒドロキシ−4−(2−ヒドロキシ−3−ドデシルオキシプロポキシ)フェニル]−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン、
HPT−26 2−(2−ヒドロキシ−4−ヘキシルオキシ)フェニル−4,6−ジフェニル−1,3,5−トリアジン、
HPT−27 2−(2−ヒドロキシ−4−メトキシフェニル)−4,6−ジフェニル−1,3,5−トリアジン、
HPT−28 2,4,6−トリス[2−ヒドロキシ−4−(3−ブトキシ−2−ヒドロキシプロポキシ)フェニル]−1,3,5−トリアジン、
HPT−29 2−(2−ヒドロキシフェニル)−4−(4−メトキシフェニル)−6−フェニル−1,3,5−トリアジン、
HPT−30 2,4−ビス(4−[2−エチルヘキシルオキシ]−2−ヒドロキシフェニル)−6−(4−メトキシフェニル)−1,3,5−トリアジン。
1.必要ならば硬化触媒の添加を伴う、常温または熱架橋性のアルキド樹脂、アクリレート樹脂、ポリエステル樹脂、エポキシ樹脂またはメラミン樹脂またはこれらの樹脂の混合物をベースとするペイント;
2.ヒドロキシル含有アクリレート、ポリエステルまたはポリエーテル樹脂および脂肪族または芳香族イソシアネート、イソシアヌレートまたはポリイソシアネートをベースとする2成分ポリウレタンペイント;
3.必要ならばメラミン樹脂の添加を伴う、ベーキングの間に脱ブロックするブロックトイソシアネート、イソシアヌレートまたはポリイソシアネートをベースとする1成分ポリウレタンペイント;
4.トリスアルコキシカルボニルトリアジン架橋剤およびヒドロキシル基含有樹脂、例えばアクリレート、ポリエステルまたはポリエーテル樹脂をベースとする1成分ポリウレタンペイント;
5.必要ならば硬化触媒を伴う、ウレタン構造内に遊離アミノ基を有する脂肪族または芳香族ウレタンアクリレートまたはポリウレタンアクリレート、およびメラミン樹脂またはポリエーテル樹脂をベースとする1成分ポリウレタンペイント;
6.(ポリ)ケチミンおよび脂肪族または芳香族イソシアネート、イソシアヌレートまたはポリイソシアネートをベースとする2成分ペイント;
7.(ポリ)ケチミンおよび不飽和アクリレート樹脂またはポリアセトアセテート樹脂またはメタクリルアミドグリコレートメチルエステルをベースとする2成分ペイント;
8.カルボキシルまたはアミノ含有ポリアクリレートおよびポリエポキシドをベースとする2成分ペイント;
9.無水物基を含有するアクリレート樹脂を、およびポリヒドロキシまたはポリアミノ成分をベースとする2成分ペイント;
10.アクリレート含有無水物およびポリエポキシドをベースとする2成分ペイント;
11.(ポリ)オキサゾリン、および無水物基を含有するアクリレート樹脂、または不飽和アクリレート樹脂、または脂肪族もしくは芳香族イソシアネート、イソシアヌレートまたはポリイソシアネートをベースとする2成分ペイント;
12.不飽和ポリアクリレートおよびポリマロネートをベースとする2成分ペイント;
13.エーテル化メラミン樹脂を併用する熱可塑性アクリレート樹脂または外部的架橋(externally crosslinking)アクリレート樹脂をベースとする熱可塑性ポリアクリレートペイント;
14.シロキサン−変性またはフッ素−変性アクリレート樹脂をベースとするペイント系。
1.1. アルキル化モノフェノール類、例えば、2,6−ジ−tert−ブチル−4−メチルフェノール、2−tert−ブチル−4,6−ジメチルフェノール、2,6−ジ−tert−ブチル−4−エチルフェノール、2,6−ジ−tert−ブチル−4−n−ブチルフェノール、2,6−ジ−tert−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−tert−ブチル−4−メトキシメチルフェノール、側鎖において直鎖状又は分岐したノニルフェノール類、例えば、2,6−ジ−ノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルトリデカ−1’−イル)フェノール及びその混合物。
2.1. 2−(2’−ヒドロキシフェニル)−ベンゾトリアゾール類、例えば、2−(2’−ヒドロキシ−5’−メチルフェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(5’−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1,1,3,3−テトラメチルブチル)フェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−メチルフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−sec−ブチル−5’−tert−ブチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクチルオキシフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−アミル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’,5’−ビス−(α,α−ジメチルベンジル)−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)−カルボニルエチル]−2’−ヒドロキシフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−ドデシル−2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−イソオクチルオキシカルボニルエチル)フェニルベンゾトリアゾール、2,2’−メチレン−ビス[4−(1,1,3,3−テトラメチルブチル)−6−ベンゾトリアゾール−2−イルフェノール];2−[3’−tert−ブチル−5’−(2−メトキシカルボニルエチル)−2’−ヒドロキシフェニル]−2H−ベンゾトリアゾールとポリエチレングリコール300とのエステル交換生成物;
(ここで、R=3’−tert−ブチル−4’−ヒドロキシ−5’−2H−ベンゾトリアゾール−2−イルフェニルである)、2−[2’−ヒドロキシ−3’−(α,α−ジメチルベンジル)−5’−(1,1,3,3−テトラメチルブチル)−フェニル]ベンゾトリアゾール;2−[2’−ヒドロキシ−3’−(1,1,3,3−テトラメチルブチル)−5’−(α,α−ジメチルベンジル)−フェニル]ベンゾトリアゾール。
DE−A−4316622;DE−A−4316876;EP−A−0589839、EP−A−0591102;EP−A−1291384で開示されているもの又は3−[4−(2−アセトキシエトキシ)フェニル]−5,7−ジ−tert−ブチルベンゾフラン−2−オン、5,7−ジ−tert−ブチル−3−[4−(2−ステアロイルオキシエトキシ)フェニル]ベンゾフラン−2−オン、3,3’−ビス[5,7−ジ−tert−ブチル−3−(4−[2−ヒドロキシエトキシ]フェニル)ベンゾフラン−2−オン]、5,7−ジ−tert−ブチル−3−(4−エトキシフェニル)ベンゾフラン−2−オン、3−(4−アセトキシ−3,5−ジメチルフェニル)−5,7−ジ−tert−ブチルベンゾフラン−2−オン、3−(3,5−ジメチル−4−ピバロイルオキシフェニル)−5,7−ジ−tert−ブチルベンゾフラン−2−オン、3−(3,4−ジメチルフェニル)−5,7−ジ−tert−ブチルベンゾフラン−2−オン、3−(2,3−ジメチルフェニル)−5,7−ジ−tert−ブチルベンゾフラン−2−オン、3−(2−アセチル−5−イソオクチルフェニル)−5−イソオクチルベンゾフラン−2−オン。
(d)金属基材に付着する、陰極析出されたコーティング;
(e)陰極析出されたコーティングに付着する、少なくとも1層の後続コーティング層;
(f)顔料または顔料の混合物を含有する、少なくとも1層のベースコーティング層;および
(g)本明細書で定義の色付きクリヤコーティング
を含む、自動車のコーティングである。
(d)金属基材に付着する、陰極析出されたコーティング;
(e)陰極析出されたコーティングに付着する、少なくとも1層の後続コーティング層;および
(f)顔料または顔料の混合物を含有する、少なくとも1層のベースコーティング層
を含む方法が好ましい。
”:インチ
C.I.:カラーインデックス
DFT:乾燥フィルム厚さ
P/B:顔料対バインダーの比
実施例1
着色ベースコーティング配合物(以下を参照)を、バッキング(Q−パネルタイプ:Special QTY 125:コイルコーティングアルミニウム0.025"×4"×12")上にスプレーし、空気中で30分乾燥させた。顔料着色ベースコーティングの得られた乾燥フィルム厚さは約16μmであった。色付きクリヤコーティング配合物(発明による)または未着色のクリヤコーティング配合物(比較;すなわちクリヤコーティング)を、顔料着色ベースコーティングの上にスプレーし、空気中で30分およびストーブ中130℃で30分乾燥させた。色付きまたは未着色のクリヤコーティングの得られた乾燥フィルム厚さは、35μm〜40μmであった。
1)Maprenal MF 900:メラミン樹脂HMMM
2)Surfynol 104E:アセチレンジオール、消泡剤/湿潤剤
3)EnviroGem AE02:Tenside、消泡剤/湿潤剤
4)Proglyde DMM:ジプロピレン−グリコール−ジメチル−エーテル、非プロトン性融合助剤
5)DOWANOL PnP:プロピレングリコール−n−プロピルエーテル、高速蒸発カップリング剤
6)DOWANOL DPnP:ジプロピレングリコールn−プロピルエーテル、蒸発融合助剤またはカップリング剤
7)VISCALEX HV 30:アクリルコポリマー水中エマルション、増粘剤およびレオロジー剤(rheology agent)
8)APU 10120 VP アクリル−ポリウレタンコポリマー、バインダー
9)ACTICIDE MBS:メチル−4−イソチアコリン、殺生物剤
各顔料を、個々に水平型ビーズミルで分散させた。分散したミルベースを一緒に混合し、ベースコーティング配合物に加えた。顔料対固体バインダーの比を1/3.6に調節した。
1)Macrynal SM 510n:アクリルポリオール樹脂(固体樹脂に基づくヒドロキシル含量約4.5%);供給業者:Solutia(元Vianova Resins)
2)Solvesso 100:芳香族炭化水素;供給業者:Exxon
3)BYK 300:レベリング剤;供給業者:BYK - Chemie
4)Desmodur N 75:イソシアネート成分;供給業者:Bayer AG
色付きおよび未着色のクリヤコーティングパネルを、色付きおよび未着色のクリヤコーティングの安定剤を変更したほかは(詳細については表6参照)、実施例1と同様に製造した。
Claims (15)
- 成分(b)が、C.I.ピグメントレッド170、177、179、202、254、264、C.I.ピグメントバイオレッド19、23、C.I.ピグメントブルー15、15:1、15:2、15:3、15:4、15:6、16、60、C.I.ピグメントイエロー109、110、129、138、139、150、184、C.I.ピグメントグリーン7、36、C.I.ピグメントオレンジ48、73、ジケト−ピロロ−ピロール顔料、キナクリドン顔料、キナクリドン/ジケト−ピロロ−ピロール顔料;並びにこれらの混合物または固溶体である、請求項1記載の色付きクリヤコーティング組成物。
- 成分(c)が、アルキド樹脂、ポリエステル樹脂、アクリル樹脂、エポキシ樹脂、ポリウレタン樹脂、メラミン/ホルムアルデヒド樹脂、尿素/ホルムアルデヒド樹脂、ブロックトイソシアネート樹脂またはこれらの組合せである、請求項1又は2記載の色付きクリヤコーティング組成物。
- コーティング組成物が自動車のコーティング組成物である、請求項1〜3のいずれか1項記載の色付きクリヤコーティング組成物。
- 成分(a)が、固体バインダー(c)の0.2〜20重量%の量で含まれる、請求項1〜4のいずれか1項記載の色付きクリヤコーティング組成物。
- 成分(b)が、固体バインダー(c)の0.2〜10重量%の量で含まれる、請求項1〜5のいずれか1項記載の色付きクリヤコーティング組成物。
- 成分(a)対成分(b)の比が、重量で、10:1〜1:1である、請求項1〜6のいずれか1項記載の色付きクリヤコーティング組成物。
- さらなる添加剤を含む、請求項1〜7のいずれか1項記載の色付きクリヤコーティング組成物。
- さらなる添加剤として、フェノールおよび/またはアミン酸化防止剤、請求項1記載のものと異なる紫外線吸収剤、ホスファイト類、ホスホナイト類、ベンゾフラノン類、金属ステアレート、金属酸化物、有機リン化合物、ヒドロキシルアミン類および/または難燃剤を含む、請求項8記載の色付きクリヤコーティング組成物。
- さらなる添加剤として、オキサミド類、2−ヒドロキシベンゾフェノン類、ベンゾエート、アクリレートおよび2−(2’−ヒドロキシフェニル)ベンゾトリアゾール類よりなる群から選択される紫外線吸収剤を含む、請求項9記載の色付きクリヤコーティング組成物。
- 請求項1〜10のいずれか1項の色付きクリヤコーティング組成物を、基材上に適用することにより得られる、色付きクリヤコーティング。
- 自動車のコーティングである、請求項11記載の色付きクリヤコーティング。
- 自動車のコーティングが、次の層:
(d)金属基材に付着する、陰極析出されたコーティング;
(e)陰極析出されたコーティングに付着する、少なくとも1層の後続コーティング層;
(f)顔料または顔料の混合物を含有する、少なくとも1層のベースコーティング層;
(g)請求項11記載の色付きクリヤコーティング
を含む、請求項12記載の色付きクリヤコーティング。 - 請求項1〜10のいずれか1項の色付きクリヤコーティング組成物を、基材に適用することを含む、色付きクリヤコーティングの製造方法。
- 基材が、次の層:
(d)金属基材に付着する、陰極析出されたコーティング;
(e)陰極析出されたコーティングに付着する、少なくとも1層の後続コーティング層;および
(f)顔料または顔料の混合物を含有する、少なくとも1層のベースコーティング層
を含む、請求項14記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07100511 | 2007-01-15 | ||
| EP07100511.0 | 2007-01-15 | ||
| PCT/EP2007/064020 WO2008086929A1 (en) | 2007-01-15 | 2007-12-17 | Tinted clear coatings uv stabili zed with 2-hydroxy phenyl triazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010515791A JP2010515791A (ja) | 2010-05-13 |
| JP5580599B2 true JP5580599B2 (ja) | 2014-08-27 |
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| EP (1) | EP2104716B1 (ja) |
| JP (1) | JP5580599B2 (ja) |
| KR (1) | KR101541431B1 (ja) |
| CN (2) | CN103819960A (ja) |
| ES (1) | ES2670436T3 (ja) |
| PL (1) | PL2104716T3 (ja) |
| WO (1) | WO2008086929A1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1746445B1 (en) | 2004-05-12 | 2012-02-22 | Adeka Corporation | Optical film |
| WO2009112425A1 (en) * | 2008-03-12 | 2009-09-17 | Basf Se | An optical film for a flat panel display |
| WO2014118251A1 (de) * | 2013-02-01 | 2014-08-07 | Bayer Materialscience Ag | Uv-härtbare beschichtungszusammensetzung |
| US9969864B2 (en) | 2013-07-08 | 2018-05-15 | Basf Se | Light stabilizers |
| WO2015030864A1 (en) * | 2013-08-30 | 2015-03-05 | Sdc Technologies, Inc. | Formable aminoplast resin-based coating compositions |
| CN106537255A (zh) * | 2014-04-18 | 2017-03-22 | 陶氏环球技术有限责任公司 | 用于lcd的彩色滤光片的蒽醌化合物 |
| WO2016097311A1 (en) * | 2014-12-19 | 2016-06-23 | Basf Se | Combination of uv absorber and pigment for protection of substrates from uv/vis-radiation |
| CN104591655A (zh) * | 2015-01-18 | 2015-05-06 | 浙江泰升节能科技有限公司 | 一种仿真贴面砖材料及其制备方法 |
| CN105838230A (zh) * | 2016-04-29 | 2016-08-10 | 李强 | 一种木器用水性聚氨酯涂料及其制备方法 |
| CN107746389B (zh) * | 2017-09-14 | 2019-10-22 | 江苏丹霞新材料有限公司 | 将傅克法制备芳基均三嗪类紫外光吸收剂中的催化剂再循环利用的方法 |
| KR20220037804A (ko) | 2020-09-18 | 2022-03-25 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (18)
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|---|---|---|---|---|
| AU572887B2 (en) * | 1983-11-28 | 1988-05-19 | Basf Corporation | Colour tinted clear coat coating system |
| US5556973A (en) * | 1994-07-27 | 1996-09-17 | Ciba-Geigy Corporation | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
| DK0704560T3 (da) * | 1994-09-30 | 1999-09-06 | Ciba Sc Holding Ag | Stabilisering af pigmenterede fibre med en synergistisk blanding af sterisk hindret amin og UV-absorberende middel |
| AU703967B2 (en) * | 1994-10-10 | 1999-04-01 | Ciba Specialty Chemicals Holding Inc. | Bisresorcinyltriazines |
| TW434296B (en) * | 1994-10-12 | 2001-05-16 | Ciba Sc Holding Ag | Process for the preparation of diaryldiketopyrrolopyrrole pigments |
| BE1012529A3 (fr) * | 1996-09-13 | 2000-12-05 | Ciba Sc Holding Ag | Melange de triaryltriazines et son utilisation pour la stabilisation de materiaux organiques. |
| DE19723504C1 (de) * | 1997-06-05 | 1998-10-15 | Basf Coatings Ag | Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung als Decklack oder Klarlack, insbesondere zur Beschichtung von Kunststoffen |
| MXPA02006120A (es) * | 1999-12-23 | 2002-12-05 | Ciba Sc Holding Ag | Mezcla de estabilizador. |
| JP4843852B2 (ja) * | 2001-02-28 | 2011-12-21 | 旭硝子株式会社 | 塗料用組成物 |
| ZA200301683B (en) * | 2002-03-04 | 2004-09-06 | Ciba Sc Holding Ag | Synergistic combinations of UV absorbers for pigmented polyolefins. |
| AU2003226258A1 (en) * | 2002-04-05 | 2003-10-27 | Ppg Industries Ohio, Inc. | Process for applying automotive quality effect coatings to metal substrates |
| US20040028823A1 (en) * | 2002-08-08 | 2004-02-12 | Wilfried Dutt | Multi-layer coating process to achieve a highly saturated color appearance on a vehicle |
| EP1308084A1 (en) * | 2002-10-02 | 2003-05-07 | Ciba SC Holding AG | Synergistic UV absorber combination |
| JP2004256802A (ja) * | 2003-02-04 | 2004-09-16 | Kansai Paint Co Ltd | 水性クリヤ塗料 |
| DE602004014517D1 (de) * | 2003-09-30 | 2008-07-31 | Kansai Paint Co Ltd | Lack und markierungsverfahren |
| US7288582B2 (en) * | 2004-04-05 | 2007-10-30 | Ppg Industries Ohio, Inc. | Colored compositions with substrate-hiding materials |
| EP1893707B1 (en) * | 2005-06-10 | 2014-12-10 | Basf Se | Automotive coating compositions comprising tris(hydroxyphenyl) triazines |
| JP5038893B2 (ja) * | 2005-06-21 | 2012-10-03 | 日本板硝子株式会社 | 透明物品およびその製造方法 |
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2007
- 2007-12-17 PL PL07857654T patent/PL2104716T3/pl unknown
- 2007-12-17 ES ES07857654.3T patent/ES2670436T3/es active Active
- 2007-12-17 US US12/520,617 patent/US20100062270A1/en not_active Abandoned
- 2007-12-17 KR KR1020097013107A patent/KR101541431B1/ko not_active Expired - Fee Related
- 2007-12-17 CN CN201410096869.0A patent/CN103819960A/zh active Pending
- 2007-12-17 JP JP2009545127A patent/JP5580599B2/ja not_active Expired - Fee Related
- 2007-12-17 EP EP07857654.3A patent/EP2104716B1/en not_active Not-in-force
- 2007-12-17 CN CNA2007800479048A patent/CN101611101A/zh active Pending
- 2007-12-17 WO PCT/EP2007/064020 patent/WO2008086929A1/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2670436T3 (es) | 2018-05-30 |
| EP2104716B1 (en) | 2018-02-21 |
| US20150079412A1 (en) | 2015-03-19 |
| KR101541431B1 (ko) | 2015-08-03 |
| KR20090110828A (ko) | 2009-10-22 |
| EP2104716A1 (en) | 2009-09-30 |
| US20100062270A1 (en) | 2010-03-11 |
| CN101611101A (zh) | 2009-12-23 |
| CN103819960A (zh) | 2014-05-28 |
| PL2104716T3 (pl) | 2018-07-31 |
| JP2010515791A (ja) | 2010-05-13 |
| WO2008086929A1 (en) | 2008-07-24 |
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