CN1196740C - 滚塑法用稳定剂组合 - Google Patents
滚塑法用稳定剂组合 Download PDFInfo
- Publication number
- CN1196740C CN1196740C CN00103708.0A CN00103708A CN1196740C CN 1196740 C CN1196740 C CN 1196740C CN 00103708 A CN00103708 A CN 00103708A CN 1196740 C CN1196740 C CN 1196740C
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl
- carbon atoms
- cycloalkyl
- butyl
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000003381 stabilizer Substances 0.000 title claims abstract description 53
- 238000001175 rotational moulding Methods 0.000 title claims description 24
- 150000001412 amines Chemical class 0.000 claims abstract description 66
- 229920000098 polyolefin Polymers 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 47
- 230000008569 process Effects 0.000 claims abstract description 11
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 229920003023 plastic Polymers 0.000 claims abstract description 7
- 239000004033 plastic Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- -1 4Be hydrogen Chemical class 0.000 claims description 132
- 229910052757 nitrogen Inorganic materials 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 20
- 150000001721 carbon Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 150000008301 phosphite esters Chemical group 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 239000005864 Sulphur Substances 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 9
- 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 9
- 230000006641 stabilisation Effects 0.000 claims description 9
- 238000011105 stabilization Methods 0.000 claims description 9
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 239000003760 tallow Substances 0.000 claims description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- GXELTROTKVKZBQ-UHFFFAOYSA-N n,n-dibenzylhydroxylamine Chemical compound C=1C=CC=CC=1CN(O)CC1=CC=CC=C1 GXELTROTKVKZBQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001421 myristyl 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])C([H])([H])[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 230000004927 fusion Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- DHXOCDLHWYUUAG-UHFFFAOYSA-N n,n-didodecylhydroxylamine Chemical compound CCCCCCCCCCCCN(O)CCCCCCCCCCCC DHXOCDLHWYUUAG-UHFFFAOYSA-N 0.000 claims description 2
- WQAJFRSBFZAUPB-UHFFFAOYSA-N n,n-dioctylhydroxylamine Chemical compound CCCCCCCCN(O)CCCCCCCC WQAJFRSBFZAUPB-UHFFFAOYSA-N 0.000 claims description 2
- RNUUDKLGODSCNO-UHFFFAOYSA-N n-dodecylhydroxylamine Chemical class CCCCCCCCCCCCNO RNUUDKLGODSCNO-UHFFFAOYSA-N 0.000 claims description 2
- JQARHBQLKPQLRB-UHFFFAOYSA-N n-heptadecyl-n-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC JQARHBQLKPQLRB-UHFFFAOYSA-N 0.000 claims description 2
- ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 claims description 2
- WGCBLWIBXXQTAW-UHFFFAOYSA-N n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC WGCBLWIBXXQTAW-UHFFFAOYSA-N 0.000 claims description 2
- IUMKEVRMAYGUGZ-UHFFFAOYSA-N n-hexadecyl-n-tetradecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCC IUMKEVRMAYGUGZ-UHFFFAOYSA-N 0.000 claims description 2
- HQYHEBGVNAJVAA-UHFFFAOYSA-N n-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCNO HQYHEBGVNAJVAA-UHFFFAOYSA-N 0.000 claims description 2
- TWHQPVYYDWEGRT-UHFFFAOYSA-N n-octadecylhydroxylamine Chemical class CCCCCCCCCCCCCCCCCCNO TWHQPVYYDWEGRT-UHFFFAOYSA-N 0.000 claims description 2
- KISSZQOBOUCLMH-UHFFFAOYSA-N n-tetradecylhydroxylamine Chemical class CCCCCCCCCCCCCCNO KISSZQOBOUCLMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 abstract description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 20
- 229960003742 phenol Drugs 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 14
- 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
- 238000002360 preparation method Methods 0.000 description 11
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole 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
- 229920001903 high density polyethylene Polymers 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 229940059574 pentaerithrityl Drugs 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 229920000092 linear low density polyethylene Polymers 0.000 description 6
- 239000004707 linear low-density polyethylene Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
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- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002530 phenolic antioxidant Substances 0.000 description 5
- 150000003008 phosphonic acid esters Chemical class 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 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
- DLQCHXZREIWMSD-UHFFFAOYSA-N C(COCCO)O.[S] Chemical compound C(COCCO)O.[S] DLQCHXZREIWMSD-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
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000002704 decyl group Chemical group [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])* 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 239000000945 filler Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 125000001400 nonyl 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])[H] 0.000 description 4
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- 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 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
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- 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 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
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- 239000006096 absorbing agent Substances 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
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- 229960000452 diethylstilbestrol Drugs 0.000 description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
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- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
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- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 2
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- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- CSWFWSPPZMEYAY-UHFFFAOYSA-N octadecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)O CSWFWSPPZMEYAY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- BCIKIEREBOMXRL-UHFFFAOYSA-N phosphocine Chemical compound C1=CC=CP=CC=C1 BCIKIEREBOMXRL-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C08K5/16—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
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C41/00—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor
- B29C41/02—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor for making articles of definite length, i.e. discrete articles
- B29C41/04—Rotational or centrifugal casting, i.e. coating the inside of a mould by rotating the mould
- B29C41/06—Rotational or centrifugal casting, i.e. coating the inside of a mould by rotating the mould about two or more axes
-
- 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
- C08K5/32—Compounds containing nitrogen bound to oxygen
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Moulding By Coating Moulds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Paper (AREA)
- Vehicle Body Suspensions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25972499A | 1999-03-01 | 1999-03-01 | |
| US09/259724 | 1999-03-01 | ||
| US09/259,724 | 1999-03-01 | ||
| US09/455,143 US6444733B1 (en) | 1999-03-01 | 1999-12-06 | Stabilizer combination for the rotomolding process |
| US09/455,143 | 1999-12-06 | ||
| US09/455143 | 1999-12-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1269378A CN1269378A (zh) | 2000-10-11 |
| CN1196740C true CN1196740C (zh) | 2005-04-13 |
Family
ID=26947499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00103708.0A Expired - Lifetime CN1196740C (zh) | 1999-03-01 | 2000-03-01 | 滚塑法用稳定剂组合 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20020156162A1 (enExample) |
| JP (1) | JP5221828B2 (enExample) |
| CN (1) | CN1196740C (enExample) |
| AU (1) | AU773507B2 (enExample) |
| BE (1) | BE1013624A5 (enExample) |
| BR (1) | BR0000971B1 (enExample) |
| CA (1) | CA2299712C (enExample) |
| DE (1) | DE10009416B9 (enExample) |
| ES (1) | ES2170639B1 (enExample) |
| FR (1) | FR2791063B1 (enExample) |
| GB (1) | GB2347426B (enExample) |
| IT (1) | IT1317865B1 (enExample) |
| NL (1) | NL1014465C2 (enExample) |
| TW (1) | TW500751B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002121333A (ja) * | 2000-10-13 | 2002-04-23 | Daiwabo Co Ltd | ポリオレフィン樹脂成形物及びそれからなるフィルム |
| JP2003292688A (ja) * | 2002-03-29 | 2003-10-15 | Daiwabo Co Ltd | 難燃性ポリオレフィン樹脂成形物およびこれを用いた積層体とエアフィルター |
| JP4437417B2 (ja) * | 2004-03-15 | 2010-03-24 | 株式会社Ａｄｅｋａ | ポリプロピレンの安定化方法 |
| GB2413331B (en) * | 2004-03-19 | 2008-10-29 | Pvaxx Res & Dev Ltd | Load-carrying apparatus and methods of manufacture |
| CA2557933A1 (en) * | 2004-03-19 | 2005-09-29 | Pvaxx Research And Development Limited | Load-carrying apparatus and methods of manufacture |
| US7241437B2 (en) * | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| US20060204745A1 (en) * | 2005-03-14 | 2006-09-14 | Jones Clint L | Light management films with zirconia particles |
| EP1869509A2 (en) * | 2005-03-11 | 2007-12-26 | 3M Innovative Properties Company | Light management films with zirconia particles |
| GB2425506B (en) | 2005-04-26 | 2010-11-10 | Pvaxx Res & Dev Ltd | Load carrying apparatus and method of manufacture |
| SA07280006B1 (ar) * | 2006-02-01 | 2011-05-14 | سيبا سبشيالتي كيميكالز هولدينج انك | استخدام امينات ثنائية معاقة فراغياً كإضافات معالجة في عمليات التشكيل الدوراني |
| US8880410B2 (en) * | 2008-07-11 | 2014-11-04 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Apparatus and method for generating a bandwidth extended signal |
| US8067490B2 (en) * | 2008-09-24 | 2011-11-29 | Chemtura Corporation | Blended phosphite or phosphonite compositions having improved hydrolytic stability |
| JP2010159396A (ja) | 2008-12-12 | 2010-07-22 | Sumitomo Chemical Co Ltd | 回転成形体用ポリオレフィン組成物 |
| CA2651514C (en) * | 2009-01-29 | 2016-05-03 | Nova Chemicals Corporation | Stabilized rotomolded parts |
| SG165299A1 (en) * | 2009-04-06 | 2010-10-28 | Sumitomo Chemical Co | Amorphous compound and production method thereof |
| WO2010123810A2 (en) * | 2009-04-21 | 2010-10-28 | Basf Performance Products Llc | Rotomolding process for polyethylene articles |
| CA2821278C (en) * | 2010-12-13 | 2019-06-18 | Cytec Technology Corp. | Processing additives and uses of same in rotational molding |
| US11267951B2 (en) | 2010-12-13 | 2022-03-08 | Cytec Technology Corp. | Stabilizer compositions containing substituted chroman compounds and methods of use |
| US9046196B2 (en) | 2011-01-11 | 2015-06-02 | Fina Technology, Inc. | Polyethylene composition for large diameter pipe stability |
| EP2729523B1 (en) * | 2011-07-07 | 2015-09-16 | Dow Global Technologies LLC | Ethylene-based polymers compositions |
| ITMI20112343A1 (it) * | 2011-12-21 | 2013-06-22 | Ifs License B V | Composizione addittivante per polimeri termoplastici |
| EP2864310B1 (en) * | 2012-06-13 | 2022-10-26 | Cytec Technology Corp. | Stabilizer compositions containing substituted chroman compounds and methods of use |
| TWI637017B (zh) * | 2012-06-13 | 2018-10-01 | 美商氰特科技股份有限公司 | 含經取代之唍化合物的安定劑組合物及使用方法 |
| TWI637018B (zh) * | 2012-06-13 | 2018-10-01 | 氰特科技股份有限公司 | 產生模製物件之方法 |
| CN104231408A (zh) * | 2014-08-07 | 2014-12-24 | 浙江瑞堂塑料科技有限公司 | 一种高耐候滚塑聚乙烯材料及其制备方法 |
| WO2016081823A1 (en) | 2014-11-20 | 2016-05-26 | Cytec Industries Inc. | Stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation |
| WO2018094085A1 (en) | 2016-11-18 | 2018-05-24 | Equistar Chemicals, Lp | Polyolefin materials for rotational molding applications having improved impact properties and color stability |
| GB2567456B (en) | 2017-10-12 | 2021-08-11 | Si Group Switzerland Chaa Gmbh | Antidegradant blend |
| CA3089890A1 (en) | 2018-02-27 | 2019-09-06 | Basf Se | Flame retardant rotomolded polyolefin |
| EP3578599A1 (en) | 2018-06-08 | 2019-12-11 | Cytec Industries Inc. | Granular stabilizer compositions for use in polymer resins and methods of making same |
| GB201807302D0 (en) | 2018-05-03 | 2018-06-20 | Addivant Switzerland Gmbh | Antidegradant blend |
| EP3841166B2 (en) | 2018-08-22 | 2025-05-07 | Basf Se | Stabilized rotomolded polyolefin |
| CN109134928B (zh) * | 2018-10-31 | 2020-05-19 | 天集化工助剂（沧州）有限公司 | N-取代的三嗪受阻胺光稳定剂及其制备方法和应用 |
| JP7343150B2 (ja) * | 2019-07-24 | 2023-09-12 | スイコー株式会社 | 回転成形用成形材料及び成形体 |
| WO2024083872A1 (en) | 2022-10-18 | 2024-04-25 | Cytec Industries Inc. | Synergistic stabilizer compositions and methods for using same for protecting organic materials from uv light and thermal degradation |
| WO2025056330A1 (en) | 2023-09-13 | 2025-03-20 | Cytec Industries Inc. | Stabilized polymer compositions with improved color resistance |
| WO2025219501A1 (en) | 2024-04-17 | 2025-10-23 | Cytec Industries Inc. | Stabilizing compositions for polymeric materials |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59150719A (ja) * | 1983-02-16 | 1984-08-29 | Sumitomo Chem Co Ltd | ポリプロピレンの粉末成形法 |
| US4703073A (en) | 1983-10-11 | 1987-10-27 | Ciba-Geigy Corporation | Alkylated N,N-dibenzylhydroxylamines and polyolefin compositions stabilized therewith |
| US4590231A (en) | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| CA1230271A (en) * | 1983-12-12 | 1987-12-15 | Ahmed A. Alim | Rotational molding grade lldpe resin |
| US4649221A (en) | 1984-07-23 | 1987-03-10 | Ciba-Geigy Corporation | Polyhydroxylamines |
| US4691015A (en) | 1984-07-23 | 1987-09-01 | Ciba-Geigy Corporation | Hydroxylamines derived from hindered amines |
| US4668721A (en) * | 1984-07-23 | 1987-05-26 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| US4668727A (en) * | 1985-11-21 | 1987-05-26 | Ciba-Geigy Corporation | Ester substituted benzylhydroxylamines and stabilized polyolefin compositions |
| US5013510A (en) | 1986-12-29 | 1991-05-07 | Ciba-Geigy Corporation | Process for preparing long chain N,N-dialkylhydroxylamines by direct oxidation |
| US4782105A (en) | 1987-04-10 | 1988-11-01 | Ciba-Geigy Corporation | Long chain N,N,-dialkylhydroxylamines and stabilized compositions |
| US4876300A (en) * | 1987-12-30 | 1989-10-24 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines |
| US5149774A (en) | 1990-07-31 | 1992-09-22 | Ciba-Geigy Corporation | Method for recycling discolored polyolefins |
| JPH0621205B2 (ja) * | 1990-10-24 | 1994-03-23 | チッソ株式会社 | 結晶性ポリプロピレン組成物 |
| JP3131599B2 (ja) * | 1990-10-25 | 2001-02-05 | 三菱化学株式会社 | 積層体の製造方法 |
| US5260381A (en) * | 1991-10-08 | 1993-11-09 | Neeco, Inc. | Crosslinkable polyethylene-based composition for rotational molding |
| GB2275473B (en) * | 1993-02-26 | 1996-08-07 | Victaulic Plc | Rotational moulding of fibre-reinforced thermoplastics particles |
| US5596033A (en) | 1993-04-15 | 1997-01-21 | Ciba-Geigy Corporation | Gas fade resistant stabilizer system for polypropylene fiber |
| TW268052B (enExample) * | 1993-04-15 | 1996-01-11 | Ciba Geigy | |
| US5844029A (en) | 1995-09-25 | 1998-12-01 | General Electric Company | Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions |
| DE59702969D1 (de) | 1996-10-30 | 2001-03-08 | Ciba Sc Holding Ag | Stabilisatorkombination für das Rotomolding-Verfahren |
| US5834541A (en) * | 1997-05-02 | 1998-11-10 | Montell North America Inc. | Olefin polymer composition having low smoke generation and fiber and film prepared therefrom |
-
2000
- 2000-02-22 NL NL1014465A patent/NL1014465C2/nl not_active IP Right Cessation
- 2000-02-24 GB GB0004230A patent/GB2347426B/en not_active Expired - Lifetime
- 2000-02-28 AU AU19522/00A patent/AU773507B2/en not_active Expired
- 2000-02-28 CA CA002299712A patent/CA2299712C/en not_active Expired - Lifetime
- 2000-02-28 DE DE10009416.3A patent/DE10009416B9/de not_active Expired - Lifetime
- 2000-02-29 TW TW089103466A patent/TW500751B/zh not_active IP Right Cessation
- 2000-02-29 ES ES200000477A patent/ES2170639B1/es not_active Expired - Fee Related
- 2000-02-29 FR FR0002509A patent/FR2791063B1/fr not_active Expired - Lifetime
- 2000-02-29 JP JP2000053525A patent/JP5221828B2/ja not_active Expired - Lifetime
- 2000-02-29 BR BRPI0000971-7A patent/BR0000971B1/pt not_active IP Right Cessation
- 2000-02-29 BE BE2000/0163A patent/BE1013624A5/fr not_active IP Right Cessation
- 2000-03-01 IT IT2000MI000398A patent/IT1317865B1/it active
- 2000-03-01 CN CN00103708.0A patent/CN1196740C/zh not_active Expired - Lifetime
-
2002
- 2002-01-08 US US10/041,151 patent/US20020156162A1/en not_active Abandoned
-
2004
- 2004-01-22 US US10/762,601 patent/US6902695B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2347426A (en) | 2000-09-06 |
| DE10009416B9 (de) | 2015-01-22 |
| TW500751B (en) | 2002-09-01 |
| FR2791063A1 (fr) | 2000-09-22 |
| US6902695B2 (en) | 2005-06-07 |
| DE10009416B4 (de) | 2014-10-30 |
| US20040152807A1 (en) | 2004-08-05 |
| ES2170639A1 (es) | 2002-08-01 |
| AU1952200A (en) | 2000-09-07 |
| US20020156162A1 (en) | 2002-10-24 |
| BR0000971A (pt) | 2000-10-03 |
| CN1269378A (zh) | 2000-10-11 |
| CA2299712C (en) | 2008-07-29 |
| GB0004230D0 (en) | 2000-04-12 |
| IT1317865B1 (it) | 2003-07-15 |
| JP5221828B2 (ja) | 2013-06-26 |
| NL1014465A1 (nl) | 2000-09-04 |
| NL1014465C2 (nl) | 2002-01-29 |
| ES2170639B1 (es) | 2003-11-16 |
| GB2347426B (en) | 2001-10-10 |
| DE10009416A1 (de) | 2000-09-07 |
| CA2299712A1 (en) | 2000-09-01 |
| ITMI20000398A1 (it) | 2001-09-03 |
| ITMI20000398A0 (it) | 2000-03-01 |
| JP2000248075A (ja) | 2000-09-12 |
| AU773507B2 (en) | 2004-05-27 |
| BR0000971B1 (pt) | 2009-05-05 |
| BE1013624A5 (fr) | 2002-05-07 |
| FR2791063B1 (fr) | 2003-03-28 |
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