TWI278479B - Stabilizer mixtures for the protection of polymer substrates - Google Patents
Stabilizer mixtures for the protection of polymer substrates Download PDFInfo
- Publication number
- TWI278479B TWI278479B TW092112814A TW92112814A TWI278479B TW I278479 B TWI278479 B TW I278479B TW 092112814 A TW092112814 A TW 092112814A TW 92112814 A TW92112814 A TW 92112814A TW I278479 B TWI278479 B TW I278479B
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- Taiwan
- Prior art keywords
- group
- alkyl
- cycloalkyl
- aryl
- branched
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000003381 stabilizer Substances 0.000 title claims abstract description 18
- 229920000307 polymer substrate Polymers 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 239000006096 absorbing agent Substances 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 3
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims abstract 2
- 150000008301 phosphite esters Chemical class 0.000 claims abstract 2
- -1 methylene (3,5 -di-t-butyl-4-hydroxyphenyl)-hydrocinnamate Chemical compound 0.000 claims description 99
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 32
- 229910052698 phosphorus Inorganic materials 0.000 claims description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229960003742 phenol Drugs 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 241000208340 Araliaceae Species 0.000 claims description 9
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 9
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 9
- 235000008434 ginseng Nutrition 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- ATWSCPDAMWVWLN-UHFFFAOYSA-N 2,6-ditert-butyl-4-octadecylphenol;propanoic acid Chemical compound CCC(O)=O.CCCCCCCCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 ATWSCPDAMWVWLN-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 235000015170 shellfish Nutrition 0.000 claims 1
- 239000013638 trimer Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 12
- 229920006351 engineering plastic Polymers 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 description 35
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 32
- 229940125782 compound 2 Drugs 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 13
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 13
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 13
- 229940125904 compound 1 Drugs 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229920001707 polybutylene terephthalate Polymers 0.000 description 11
- 229920000768 polyamine Polymers 0.000 description 9
- 229920006324 polyoxymethylene Polymers 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 7
- 239000005062 Polybutadiene Substances 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 7
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 7
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 7
- QNAPYKYKJNQLOF-UHFFFAOYSA-N 2-phenylpropane-1,1,3,3-tetracarboxylic acid Chemical class OC(=O)C(C(O)=O)C(C(C(O)=O)C(O)=O)C1=CC=CC=C1 QNAPYKYKJNQLOF-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
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- 150000005846 sugar alcohols Polymers 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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- 229920000877 Melamine resin Polymers 0.000 description 4
- 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 description 4
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- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
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- 150000003568 thioethers Chemical class 0.000 description 4
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- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 3
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
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- CPAJUXUFVYLYLX-UHFFFAOYSA-N [1-(hydroxymethyl)-3,5,8-trioxabicyclo[2.2.2]octan-4-yl]phosphonic acid Chemical compound C1OC2(P(O)(O)=O)OCC1(CO)CO2 CPAJUXUFVYLYLX-UHFFFAOYSA-N 0.000 description 2
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- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
- 229920001345 ε-poly-D-lysine Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- 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
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- 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
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Insulating Materials (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/145,366 US7081213B2 (en) | 2002-05-14 | 2002-05-14 | Stabilizer mixtures for the protection of polymer substrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200307716A TW200307716A (en) | 2003-12-16 |
| TWI278479B true TWI278479B (en) | 2007-04-11 |
Family
ID=29418619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092112814A TWI278479B (en) | 2002-05-14 | 2003-05-12 | Stabilizer mixtures for the protection of polymer substrates |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7081213B2 (enExample) |
| EP (1) | EP1529075B1 (enExample) |
| JP (1) | JP2005530869A (enExample) |
| KR (1) | KR20050006257A (enExample) |
| CN (1) | CN100354351C (enExample) |
| AT (1) | ATE377625T1 (enExample) |
| AU (1) | AU2003223078A1 (enExample) |
| CA (1) | CA2481999A1 (enExample) |
| DE (1) | DE60317336T2 (enExample) |
| ES (1) | ES2292954T3 (enExample) |
| MY (1) | MY135425A (enExample) |
| TW (1) | TWI278479B (enExample) |
| WO (1) | WO2003095543A2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1462478A1 (en) * | 2003-03-26 | 2004-09-29 | Clariant International Ltd. | Improved long term dimensional stability of pigmented polymer articles |
| MY139524A (en) | 2004-06-30 | 2009-10-30 | Ciba Holding Inc | Stabilization of polyether polyol, polyester polyol or polyurethane compositions |
| DE102006014118A1 (de) * | 2006-03-24 | 2007-09-27 | Bayer Materialscience Ag | Formkörper mit hoher Lichtstreuung und hoher Lichttransmission zur Verwendung als Diffuser-Sheet in Flachbildschirmen |
| EP2061834B1 (en) | 2006-09-01 | 2017-07-19 | Clariant International Ltd | Stabilizer compositions for improved protection against degradation of organic substrates by light |
| US8147769B1 (en) | 2007-05-16 | 2012-04-03 | Abbott Cardiovascular Systems Inc. | Stent and delivery system with reduced chemical degradation |
| HUE031014T2 (en) * | 2007-05-25 | 2017-06-28 | Clariant Int Ltd | Stabilization of polycarbonates and polycarbonate mixtures |
| EP2190903B1 (en) * | 2007-09-04 | 2012-04-04 | Basf Se | Cyclic phosphines as flame retardants |
| US20090319031A1 (en) * | 2008-06-19 | 2009-12-24 | Yunbing Wang | Bioabsorbable Polymeric Stent With Improved Structural And Molecular Weight Integrity |
| EP2204404B1 (en) * | 2008-12-24 | 2012-04-25 | Airsec S.A.S. | Polymer compositions with improved barrier properties against the permeation of oxygen |
| KR101175897B1 (ko) | 2009-12-14 | 2012-08-21 | 주식회사 효성 | 폴리아미드 수지 조성물 및 폴리아미드의 제조방법 |
| WO2011106198A1 (en) | 2010-02-23 | 2011-09-01 | Christopher Gordon Atwood | Methods for the detection of biologically relevant molecules and their interaction characteristics |
| US8598257B2 (en) * | 2010-12-30 | 2013-12-03 | Cheil Industries Inc. | Polycarbonate resin composition |
| JP2017218563A (ja) * | 2016-06-10 | 2017-12-14 | 旭化成株式会社 | ポリアセタール樹脂組成物及び成形体 |
| CN108034385B (zh) * | 2017-12-29 | 2019-08-23 | 天津利安隆新材料股份有限公司 | 一种用于光伏eva胶膜的光稳定剂组合物 |
| US11110688B2 (en) * | 2018-07-05 | 2021-09-07 | Toray Plastics (America), Inc. | Anti-blush and chemical resistant polyester film |
| CN111393355A (zh) * | 2020-04-13 | 2020-07-10 | 宿迁联盛科技股份有限公司 | 一种新型高效端基受阻胺光稳定剂的制备方法 |
| CN114409960B (zh) * | 2022-01-21 | 2023-05-09 | 深圳市那鸿科技有限公司 | 一种阻燃/抗氧协同助剂及其合成方法和在回收pet中的应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH491991A (de) | 1968-10-04 | 1970-06-15 | Bayer Ag | Verwendung von Tetracarbonsäureestern zum Schützen organischer Stoffe gegen UV-Strahlung |
| US3637907A (en) * | 1969-02-26 | 1972-01-25 | Phillips Petroleum Co | Polyolefins stabilized with diphosphines |
| DE2718458A1 (de) * | 1976-05-04 | 1977-11-24 | Ciba Geigy Ag | Neue stabilisatoren |
| FR2540380B1 (fr) | 1983-02-03 | 1986-02-07 | Oreal | Composition cosmetique pour la protection contre le rayonnement ultraviolet et son utilisation a cet effet |
| US5380774A (en) * | 1989-11-28 | 1995-01-10 | Hoechst Celanese Corporation | Nylon molding compositions exhibiting improved protection against UV-light degradation |
| US6153676A (en) | 1992-08-17 | 2000-11-28 | Clariant Finance (Bvi) Limited | Stabilized polyolefins |
| US6369140B1 (en) * | 1993-03-25 | 2002-04-09 | Clariant Finance (Bvi) Limited | Phosphorus compounds |
| JPH0952975A (ja) | 1995-08-18 | 1997-02-25 | Clariant Internatl Ltd | 顔料の安定化方法及びこの方法に用いる組成物 |
| EP0892828B1 (en) | 1996-04-12 | 2001-05-30 | Clariant Finance (BVI) Limited | Stabilization of polyolefins |
| US5969014A (en) | 1997-09-23 | 1999-10-19 | Clariant Finance (Bvi) Limited | Synergistic polyamide stabilization method |
| US5965261A (en) * | 1998-11-16 | 1999-10-12 | Clariant Finance (Bvi) Limited | Polyester |
| EP1270728B1 (en) | 2000-02-24 | 2007-04-18 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing avermectin derivative |
| GB0004437D0 (en) | 2000-02-25 | 2000-04-12 | Clariant Int Ltd | Synergistic combinations of phenolic antioxidants |
| US7173128B2 (en) * | 2001-08-13 | 2007-02-06 | Ciba Specialty Chemicals Corporation | Ultraviolet light absorbers |
-
2002
- 2002-05-14 US US10/145,366 patent/US7081213B2/en not_active Expired - Fee Related
-
2003
- 2003-05-12 JP JP2004503549A patent/JP2005530869A/ja active Pending
- 2003-05-12 KR KR10-2004-7018329A patent/KR20050006257A/ko not_active Ceased
- 2003-05-12 TW TW092112814A patent/TWI278479B/zh not_active IP Right Cessation
- 2003-05-12 ES ES03719049T patent/ES2292954T3/es not_active Expired - Lifetime
- 2003-05-12 AU AU2003223078A patent/AU2003223078A1/en not_active Abandoned
- 2003-05-12 DE DE60317336T patent/DE60317336T2/de not_active Expired - Fee Related
- 2003-05-12 CA CA002481999A patent/CA2481999A1/en not_active Abandoned
- 2003-05-12 WO PCT/IB2003/001908 patent/WO2003095543A2/en not_active Ceased
- 2003-05-12 MY MYPI20031772A patent/MY135425A/en unknown
- 2003-05-12 EP EP03719049A patent/EP1529075B1/en not_active Expired - Lifetime
- 2003-05-12 AT AT03719049T patent/ATE377625T1/de not_active IP Right Cessation
- 2003-05-12 CN CNB038108062A patent/CN100354351C/zh not_active Expired - Fee Related
-
2006
- 2006-06-08 US US11/449,049 patent/US7332535B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003095543A3 (en) | 2005-03-10 |
| CA2481999A1 (en) | 2003-11-20 |
| HK1079540A1 (zh) | 2006-04-07 |
| US7332535B2 (en) | 2008-02-19 |
| WO2003095543A2 (en) | 2003-11-20 |
| ATE377625T1 (de) | 2007-11-15 |
| US7081213B2 (en) | 2006-07-25 |
| DE60317336T2 (de) | 2008-08-28 |
| WO2003095543B1 (en) | 2005-04-21 |
| US20030234386A1 (en) | 2003-12-25 |
| EP1529075B1 (en) | 2007-11-07 |
| US20060226395A1 (en) | 2006-10-12 |
| AU2003223078A1 (en) | 2003-11-11 |
| CN1653124A (zh) | 2005-08-10 |
| DE60317336D1 (de) | 2007-12-20 |
| TW200307716A (en) | 2003-12-16 |
| ES2292954T3 (es) | 2008-03-16 |
| EP1529075A2 (en) | 2005-05-11 |
| MY135425A (en) | 2008-04-30 |
| CN100354351C (zh) | 2007-12-12 |
| JP2005530869A (ja) | 2005-10-13 |
| KR20050006257A (ko) | 2005-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |