CN1237058C - 合成聚合物的稳定方法 - Google Patents
合成聚合物的稳定方法 Download PDFInfo
- Publication number
- CN1237058C CN1237058C CNB021315973A CN02131597A CN1237058C CN 1237058 C CN1237058 C CN 1237058C CN B021315973 A CNB021315973 A CN B021315973A CN 02131597 A CN02131597 A CN 02131597A CN 1237058 C CN1237058 C CN 1237058C
- Authority
- CN
- China
- Prior art keywords
- butyl
- compound
- phenyl
- hydroxyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 15
- 229920001059 synthetic polymer Polymers 0.000 title abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000003381 stabilizer Substances 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 67
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 39
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 35
- 229920000570 polyether Polymers 0.000 claims description 19
- 239000000654 additive Substances 0.000 claims description 15
- 125000002347 octyl 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])[H] 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 11
- 230000000996 additive effect Effects 0.000 claims description 11
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 238000000354 decomposition reaction Methods 0.000 claims description 11
- 229920001169 thermoplastic Polymers 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 229920000098 polyolefin Polymers 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- -1 isobutyl- Chemical group 0.000 description 120
- 229910052757 nitrogen Inorganic materials 0.000 description 43
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 38
- 239000000126 substance Substances 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 24
- 239000005056 polyisocyanate Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- 229960003742 phenol Drugs 0.000 description 19
- 229920001228 polyisocyanate Polymers 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 229920002554 vinyl polymer Polymers 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 13
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000004700 high-density polyethylene Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 239000004033 plastic Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229920001903 high density polyethylene Polymers 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 7
- 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 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 229920002396 Polyurea Polymers 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 150000001565 benzotriazoles Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000003351 stiffener Substances 0.000 description 5
- PMNGNPRHPYYVNM-UHFFFAOYSA-N 1-hydroxyundecane-3-sulfonic acid Chemical compound CCCCCCCCC(CCO)S(O)(=O)=O PMNGNPRHPYYVNM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- GXFQBBOZTNQHMW-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(NCCCCCCN)CC(C)(C)N1 GXFQBBOZTNQHMW-UHFFFAOYSA-N 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000011496 polyurethane foam Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 3
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
- 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
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 3
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229920000554 ionomer Polymers 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000003019 stabilising effect Effects 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
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- 239000013638 trimer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- SQKUFYLUXROIFM-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-2-methyl-5-(phosphonooxymethyl)pyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(COP(O)(O)=O)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2COP(O)(O)=O)O)CC(O)=O)=C1O SQKUFYLUXROIFM-UHFFFAOYSA-N 0.000 description 2
- ZFABKRKKUNPJSL-UHFFFAOYSA-N 2-octylphenol 2H-thiazine Chemical compound S1NC=CC=C1.C(CCCCCCC)C1=C(C=CC=C1)O ZFABKRKKUNPJSL-UHFFFAOYSA-N 0.000 description 2
- SXGXVOZDLWXVKM-UHFFFAOYSA-N 3-dodecylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)NC1=O SXGXVOZDLWXVKM-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MSGFMKMFGGXSTO-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC Chemical compound C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC MSGFMKMFGGXSTO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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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
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- 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)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
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| EP01810876.1 | 2001-09-11 | ||
| EP01810876 | 2001-09-11 |
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| CN1407005A CN1407005A (zh) | 2003-04-02 |
| CN1237058C true CN1237058C (zh) | 2006-01-18 |
Family
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| CNB021315973A Expired - Lifetime CN1237058C (zh) | 2001-09-11 | 2002-09-10 | 合成聚合物的稳定方法 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968339A (zh) * | 2015-03-10 | 2016-09-28 | 赢创德固赛有限公司 | 用于制备低排放pur 体系的抗氧化剂 |
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| CN1976986B (zh) * | 2004-06-30 | 2011-11-16 | 西巴特殊化学品控股有限公司 | 聚醚多元醇、聚酯多元醇或者聚氨酯组合物的稳定 |
| US20090076198A1 (en) | 2004-10-25 | 2009-03-19 | Thomas Giesenberg | Functionalized nanoparticles |
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- 2002-08-09 MY MYPI20022971A patent/MY129373A/en unknown
- 2002-09-02 CO CO02077628A patent/CO5270026A1/es not_active Application Discontinuation
- 2002-09-03 DK DK02405759T patent/DK1291384T3/da active
- 2002-09-03 EP EP02405759A patent/EP1291384B1/en not_active Expired - Lifetime
- 2002-09-03 AT AT02405759T patent/ATE299911T1/de active
- 2002-09-03 PT PT02405759T patent/PT1291384E/pt unknown
- 2002-09-03 ES ES02405759T patent/ES2246008T3/es not_active Expired - Lifetime
- 2002-09-03 DE DE60205071T patent/DE60205071T2/de not_active Expired - Lifetime
- 2002-09-06 SG SG200205419A patent/SG125905A1/en unknown
- 2002-09-06 PL PL355901A patent/PL205846B1/pl unknown
- 2002-09-06 MX MXPA02008708A patent/MXPA02008708A/es active IP Right Grant
- 2002-09-09 KR KR1020020054145A patent/KR100849947B1/ko not_active Expired - Lifetime
- 2002-09-09 US US10/237,313 patent/US6881774B2/en not_active Expired - Lifetime
- 2002-09-09 AR ARP020103402A patent/AR036500A1/es active IP Right Grant
- 2002-09-09 CA CA2401927A patent/CA2401927C/en not_active Expired - Lifetime
- 2002-09-10 HU HU0202991A patent/HU229128B1/hu not_active IP Right Cessation
- 2002-09-10 BR BRPI0203538-3A patent/BR0203538B1/pt not_active IP Right Cessation
- 2002-09-10 RU RU2002123926/04A patent/RU2286361C2/ru not_active IP Right Cessation
- 2002-09-10 CN CNB021315973A patent/CN1237058C/zh not_active Expired - Lifetime
- 2002-09-11 AU AU2002300979A patent/AU2002300979B2/en not_active Ceased
- 2002-09-11 JP JP2002265357A patent/JP4314610B2/ja not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968339A (zh) * | 2015-03-10 | 2016-09-28 | 赢创德固赛有限公司 | 用于制备低排放pur 体系的抗氧化剂 |
| CN105968339B (zh) * | 2015-03-10 | 2020-03-27 | 赢创运营有限公司 | 用于制备低排放pur体系的抗氧化剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2246008T3 (es) | 2006-02-01 |
| EP1291384A1 (en) | 2003-03-12 |
| AR036500A1 (es) | 2004-09-15 |
| KR100849947B1 (ko) | 2008-08-01 |
| US20030109611A1 (en) | 2003-06-12 |
| MXPA02008708A (es) | 2003-03-27 |
| DE60205071D1 (de) | 2005-08-25 |
| HUP0202991A2 (en) | 2003-05-28 |
| US6881774B2 (en) | 2005-04-19 |
| PL355901A1 (en) | 2003-03-24 |
| AU2002300979B2 (en) | 2007-11-01 |
| SG125905A1 (en) | 2006-10-30 |
| DE60205071T2 (de) | 2006-05-24 |
| EP1291384B1 (en) | 2005-07-20 |
| BR0203538A (pt) | 2003-06-03 |
| BR0203538B1 (pt) | 2011-09-06 |
| CA2401927A1 (en) | 2003-03-11 |
| PL205846B1 (pl) | 2010-06-30 |
| DK1291384T3 (da) | 2005-09-19 |
| ATE299911T1 (de) | 2005-08-15 |
| JP4314610B2 (ja) | 2009-08-19 |
| HUP0202991A3 (en) | 2006-02-28 |
| CN1407005A (zh) | 2003-04-02 |
| HU0202991D0 (cg-RX-API-DMAC7.html) | 2002-10-28 |
| RU2286361C2 (ru) | 2006-10-27 |
| MY129373A (en) | 2007-03-30 |
| CA2401927C (en) | 2010-08-03 |
| JP2003176417A (ja) | 2003-06-24 |
| KR20030022708A (ko) | 2003-03-17 |
| CO5270026A1 (es) | 2003-04-30 |
| PT1291384E (pt) | 2005-11-30 |
| TW593303B (en) | 2004-06-21 |
| HU229128B1 (en) | 2013-08-28 |
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