CA2481999A1 - Stabilizer mixtures for the protection of polymer substrates - Google Patents
Stabilizer mixtures for the protection of polymer substrates Download PDFInfo
- Publication number
- CA2481999A1 CA2481999A1 CA002481999A CA2481999A CA2481999A1 CA 2481999 A1 CA2481999 A1 CA 2481999A1 CA 002481999 A CA002481999 A CA 002481999A CA 2481999 A CA2481999 A CA 2481999A CA 2481999 A1 CA2481999 A1 CA 2481999A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cycloalkyl
- branched
- linear
- appropriate
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 239000003381 stabilizer Substances 0.000 title claims abstract description 18
- 229920000307 polymer substrate Polymers 0.000 title description 4
- -1 amino- Chemical class 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000006096 absorbing agent Substances 0.000 claims abstract description 25
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 150000008301 phosphite esters Chemical class 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229920006351 engineering plastic Polymers 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims abstract description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000006686 (C1-C24) alkyl 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
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001624 naphthyl group Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004437 phosphorous atom Chemical class 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 7
- 230000007774 longterm Effects 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 2
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 52
- 229920001577 copolymer Polymers 0.000 description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 35
- 229940125782 compound 2 Drugs 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 12
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 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 11
- 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 10
- 238000009472 formulation Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 239000004033 plastic Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 229920006324 polyoxymethylene Polymers 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- 229940099514 low-density polyethylene Drugs 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920001707 polybutylene terephthalate Polymers 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920002857 polybutadiene Polymers 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 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
- 239000000654 additive Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 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
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 239000011732 tocopherol Substances 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 229920000554 ionomer Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 229960001295 tocopherol Drugs 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 3
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 3
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920002480 polybenzimidazole Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 229920006380 polyphenylene oxide Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- 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 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
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- 125000005591 trimellitate group Chemical group 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/145,366 | 2002-05-14 | ||
| US10/145,366 US7081213B2 (en) | 2002-05-14 | 2002-05-14 | Stabilizer mixtures for the protection of polymer substrates |
| PCT/IB2003/001908 WO2003095543A2 (en) | 2002-05-14 | 2003-05-12 | Stabilizer mixtures for the protection of polymer substrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2481999A1 true CA2481999A1 (en) | 2003-11-20 |
Family
ID=29418619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002481999A Abandoned CA2481999A1 (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 |
| WO2008025738A1 (en) * | 2006-09-01 | 2008-03-06 | 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 |
| WO2008145573A1 (en) * | 2007-05-25 | 2008-12-04 | Clariant Finance (Bvi) Limited | Stabilization of polycarbonates and polycarbonate blends |
| JP5399394B2 (ja) * | 2007-09-04 | 2014-01-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 難燃剤としての環状ホスフィン |
| US20090319031A1 (en) * | 2008-06-19 | 2009-12-24 | Yunbing Wang | Bioabsorbable Polymeric Stent With Improved Structural And Molecular Weight Integrity |
| ES2385763T3 (es) * | 2008-12-24 | 2012-07-31 | Airsec S.A.S. | Composiciones poliméricas con mejores propiedades de barrera frente a la permeación de oxígeno |
| KR101175897B1 (ko) | 2009-12-14 | 2012-08-21 | 주식회사 효성 | 폴리아미드 수지 조성물 및 폴리아미드의 제조방법 |
| CN102762746B (zh) | 2010-02-23 | 2015-04-29 | 克里斯托弗·戈登·阿特伍德 | 检测生物相关分子及其相互作用性质的方法 |
| 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 |
| AU2001234164A1 (en) | 2000-02-24 | 2001-09-03 | 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 |
| CA2454080A1 (en) * | 2001-08-13 | 2003-02-27 | Robert Edward Detlefsen | Ultraviolet light absorbers |
-
2002
- 2002-05-14 US US10/145,366 patent/US7081213B2/en not_active Expired - Fee Related
-
2003
- 2003-05-12 WO PCT/IB2003/001908 patent/WO2003095543A2/en not_active Ceased
- 2003-05-12 CN CNB038108062A patent/CN100354351C/zh not_active Expired - Fee Related
- 2003-05-12 CA CA002481999A patent/CA2481999A1/en not_active Abandoned
- 2003-05-12 EP EP03719049A patent/EP1529075B1/en not_active Expired - Lifetime
- 2003-05-12 ES ES03719049T patent/ES2292954T3/es not_active Expired - Lifetime
- 2003-05-12 TW TW092112814A patent/TWI278479B/zh not_active IP Right Cessation
- 2003-05-12 AT AT03719049T patent/ATE377625T1/de not_active IP Right Cessation
- 2003-05-12 AU AU2003223078A patent/AU2003223078A1/en not_active Abandoned
- 2003-05-12 MY MYPI20031772A patent/MY135425A/en unknown
- 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 DE DE60317336T patent/DE60317336T2/de 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 |
| US20060226395A1 (en) | 2006-10-12 |
| ATE377625T1 (de) | 2007-11-15 |
| ES2292954T3 (es) | 2008-03-16 |
| CN1653124A (zh) | 2005-08-10 |
| JP2005530869A (ja) | 2005-10-13 |
| HK1079540A1 (zh) | 2006-04-07 |
| TW200307716A (en) | 2003-12-16 |
| CN100354351C (zh) | 2007-12-12 |
| KR20050006257A (ko) | 2005-01-15 |
| EP1529075B1 (en) | 2007-11-07 |
| WO2003095543B1 (en) | 2005-04-21 |
| AU2003223078A1 (en) | 2003-11-11 |
| TWI278479B (en) | 2007-04-11 |
| MY135425A (en) | 2008-04-30 |
| DE60317336D1 (de) | 2007-12-20 |
| EP1529075A2 (en) | 2005-05-11 |
| DE60317336T2 (de) | 2008-08-28 |
| US7081213B2 (en) | 2006-07-25 |
| US20030234386A1 (en) | 2003-12-25 |
| WO2003095543A2 (en) | 2003-11-20 |
| US7332535B2 (en) | 2008-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |