CN1142981C - 阻燃聚碳酸酯组合物 - Google Patents
阻燃聚碳酸酯组合物 Download PDFInfo
- Publication number
- CN1142981C CN1142981C CNB008111375A CN00811137A CN1142981C CN 1142981 C CN1142981 C CN 1142981C CN B008111375 A CNB008111375 A CN B008111375A CN 00811137 A CN00811137 A CN 00811137A CN 1142981 C CN1142981 C CN 1142981C
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- CN
- China
- Prior art keywords
- potassium
- salt
- acid
- sodium
- stablizer
- 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 - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 229920000515 polycarbonate Polymers 0.000 title claims description 39
- 239000004417 polycarbonate Substances 0.000 title claims description 36
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title description 9
- 239000003063 flame retardant Substances 0.000 title description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- -1 poly(alkyl methacrylate Chemical compound 0.000 claims abstract description 29
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 16
- 229920000098 polyolefin Polymers 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000004431 polycarbonate resin Substances 0.000 claims abstract description 10
- 229920005668 polycarbonate resin Polymers 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 239000006069 physical mixture Substances 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
- 229910052700 potassium Inorganic materials 0.000 claims description 19
- 239000011591 potassium Substances 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 11
- 229920001169 thermoplastic Polymers 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000206 moulding compound Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
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- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- UBJQWPYKKRPJRP-UHFFFAOYSA-N [Na].CP(O)(O)O Chemical compound [Na].CP(O)(O)O UBJQWPYKKRPJRP-UHFFFAOYSA-N 0.000 claims description 3
- KGKLCLBZRKRFSE-UHFFFAOYSA-N [Na].ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl Chemical compound [Na].ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl KGKLCLBZRKRFSE-UHFFFAOYSA-N 0.000 claims description 3
- FDFKRDOUGFSUGN-UHFFFAOYSA-N [Na].OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl Chemical compound [Na].OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl FDFKRDOUGFSUGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- JMYJVSDYOBBBKY-UHFFFAOYSA-N lithium;phenylphosphonic acid Chemical compound [Li].OP(O)(=O)C1=CC=CC=C1 JMYJVSDYOBBBKY-UHFFFAOYSA-N 0.000 claims description 3
- XZJUCCSDEMXAQU-UHFFFAOYSA-N sodium;1,2,4-trichlorobenzene Chemical compound [Na].ClC1=CC=C(Cl)C(Cl)=C1 XZJUCCSDEMXAQU-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- YIGOASFQWFSGED-UHFFFAOYSA-N [Na].ClC1=CC=CC(=C1)Cl Chemical compound [Na].ClC1=CC=CC(=C1)Cl YIGOASFQWFSGED-UHFFFAOYSA-N 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- BFDYSJCMAFSRDH-UHFFFAOYSA-N 2-phenylethylphosphonic acid Chemical class OP(O)(=O)CCC1=CC=CC=C1 BFDYSJCMAFSRDH-UHFFFAOYSA-N 0.000 claims 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 2
- OWXOWEXYVNQURQ-UHFFFAOYSA-N ClC=1C(=C(C(=C(C1)Cl)Cl)Cl)Cl.[K] Chemical compound ClC=1C(=C(C(=C(C1)Cl)Cl)Cl)Cl.[K] OWXOWEXYVNQURQ-UHFFFAOYSA-N 0.000 claims 2
- OLIBILNCEIVJPN-UHFFFAOYSA-N [K].CP(O)(O)O Chemical compound [K].CP(O)(O)O OLIBILNCEIVJPN-UHFFFAOYSA-N 0.000 claims 2
- KNKHBEWELJVZOI-UHFFFAOYSA-N [K].ClC1=CC=CC(=C1)Cl Chemical compound [K].ClC1=CC=CC(=C1)Cl KNKHBEWELJVZOI-UHFFFAOYSA-N 0.000 claims 2
- XTOGCIYNCOHJAY-UHFFFAOYSA-N [K].OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl Chemical compound [K].OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl XTOGCIYNCOHJAY-UHFFFAOYSA-N 0.000 claims 2
- MMDSSERULWYGSW-UHFFFAOYSA-N methanesulfonic acid;potassium Chemical compound [K].CS(O)(=O)=O MMDSSERULWYGSW-UHFFFAOYSA-N 0.000 claims 2
- 150000003009 phosphonic acids Chemical class 0.000 claims 2
- QPTWOXZOCFKGHH-UHFFFAOYSA-N potassium;1,2,4-trichlorobenzene Chemical compound [K].ClC1=CC=C(Cl)C(Cl)=C1 QPTWOXZOCFKGHH-UHFFFAOYSA-N 0.000 claims 2
- FLFZSGCHLUSTST-UHFFFAOYSA-N [Na].OC(=O)C1=CC=C(Cl)C=C1Cl Chemical compound [Na].OC(=O)C1=CC=C(Cl)C=C1Cl FLFZSGCHLUSTST-UHFFFAOYSA-N 0.000 claims 1
- LYJZNXAVZMEXDH-UHFFFAOYSA-N octadecan-8-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCC(OC(=O)C(C)=C)CCCCCCC LYJZNXAVZMEXDH-UHFFFAOYSA-N 0.000 claims 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 5
- 150000001340 alkali metals Chemical group 0.000 abstract description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 238000009757 thermoplastic moulding Methods 0.000 abstract 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 21
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- 238000000034 method Methods 0.000 description 14
- 229910052728 basic metal Inorganic materials 0.000 description 10
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- 150000001875 compounds Chemical class 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
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- 229910052799 carbon Inorganic materials 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004425 Makrolon Substances 0.000 description 3
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- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 101000648997 Homo sapiens Tripartite motif-containing protein 44 Proteins 0.000 description 2
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- 229920006362 Teflon® Polymers 0.000 description 2
- 102100028017 Tripartite motif-containing protein 44 Human genes 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 1
- XJGTVJRTDRARGO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 XJGTVJRTDRARGO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 229920004042 Makrolon® 2608 Polymers 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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- SXHFVWRWQQGAOF-UHFFFAOYSA-N [SH2]=N.C1(=CC=CC=C1)C Chemical compound [SH2]=N.C1(=CC=CC=C1)C SXHFVWRWQQGAOF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
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- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- IIYFAKIEWZDVMP-UHFFFAOYSA-N linear paraffin C13 Natural products CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
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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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/22—Thermoplastic resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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Abstract
本发明公开了一种热塑性模塑组合物,其包括聚碳酸酯树脂和添加剂量的、确定量的稳定剂和盐。该组合物的特征在于它没有放射纹及其改进的阻燃性能。本发明的稳定剂是聚(甲基丙烯酸烷基酯)和氟化聚烯烃的物理混合物,盐是全氟链烷磺酸、芳族硫酰亚胺或芳族磺酸的碱金属或碱土金属盐。
Description
技术领域
本发明涉及热塑性模塑组合物和更具体地涉及阻燃聚碳酸酯组合物。
背景技术
自从美国专利3,028,365在1962年4月颁发开始,芳族聚碳酸酯已经是公知的和被人们接受为适用于许多用途的热塑性树脂,这些用途包括注塑、挤出和成膜。这些聚碳酸酯的化学、合成、性能和应用在下列文献中得到充分讨论:Schnell的聚碳酸酯的化学和物理,Interscience,1964及Christopher和Fox的聚碳酸酯,Reinhold,1962。
尽管聚碳酸酯有一定的内在阻燃性,是自熄性的,然而对于阻燃性能的更高要求已经引起许多尝试,以提高此性能。已经采用两种通用方法。
一种方法是向聚碳酸酯组合物中加入相当量的卤素,特别是溴或氯。卤素可由聚碳酸酯聚合物链携带,如在美国专利3,751,400和3,334,154中所述,或由单体化合物携带,如在美国专利3,382,207中所述。然而,已经发现相当量卤素的存在对聚碳酸酯的性能是有害的,并且已经建议使用许多添加剂,如在美国专利3,647,747和3,733,295中提出的那些,来克服这些有害影响。
在本领域中,包含聚四氟乙烯(PTFE)的阻燃聚碳酸酯组合物是已知的。美国专利4,391,935公开了这样的组合物,它也包括某些盐。美国专利3,294,871公开了生产包含PTFE和热塑性聚合物的模塑组合物的方法,它包括共混热塑性聚合物和PTFE的胶乳以生产PTFE和热塑性聚合物的分散的、基本均匀的混合物,和通过从其中除去挥发性物质而回收组合物。在聚合物中,聚碳酸酯列于第3栏,第6-8行。据称公开的组合物提供的优点在于冲击强度、熔体指数、摩擦系数、水透过性低和增加的HDT。
美国专利3,005,795公开了包含PTFE树脂的组合物,它的形式是精细分散的微纤维和亚微纤维粒子。聚碳酸酯作为合适的基体公开于第3栏,第18-19行。公开于美国专利3,290,412的PTFE树脂的改进模塑性依赖于向其中加入10-40%的聚碳酸酯。
美国专利3,723,373公开了将PTFE乳液加入到聚对苯二甲酸乙二醇酯中以改进加工性能。法国专利1,412,767解决了与PTFE模塑性有关的问题。
Lontz等人在工业和工程化学,44卷,No.8,1800页(1952)描述了在PTFE成膜特征中的一般分散性能。也公开了通过加入电解质或其它溶剂,或通过其它方法而进行分散体的凝聚。
德国公开说明书DE-OS 33 22 260公开了与ABS共沉淀及加入了聚碳酸酯的PTFE。相关技术公开在EP-OS 0,154,138中,它公开了包括ABS和PTFE的体系,DE-OS 34 17 476公开了聚酰胺和PTFE的体系,DE-OS 34 18 750涉及与PTFE共沉淀的ABS体系。同样相关的是DE-OS 34 20 002、DE-OS 34 22 862、DE-OS 35 12 638(等同于EP-OS0,174,493)、DE-OS 29 48 439和美国专利4,208,489。
美国专利3,940,455公开了通过在溶剂中溶解弹性体聚合物和引入PTFE以形成悬浮液和随后通过混合悬浮液和非溶剂而将两种物质共沉淀而将Teflon引入弹性体烃中的方法。据称共沉淀物显示改进的物理性能。
在本发明中同样相关的是美国专利4,753,994,它公开了阻燃聚碳酸酯组合物,该组合物包含聚碳酸酯和氟聚合物的共沉淀物。同样相关的是EP 899303,它公开了阻燃聚碳酸酯组合物,该组合物包含被热塑性SAN共聚物包封的氟聚合物树脂粒子。在此提及的美国专利5,773,493公开了在热塑性聚合物中分散添加剂如PTFE的方法,和此发明方法的产品在制备模塑组合物中的用途。
发明内容
本发明公开了一种热塑性模塑组合物,它包括聚碳酸酯树脂和添加剂量的、确定量的稳定剂和盐。该组合物的特征在于它没有放射纹(splay)以及其改进的阻燃性能。本发明的稳定剂是聚(甲基丙烯酸烷基酯)和氟化聚烯烃的物理混合物,和所述盐是全氟链烷磺酸、芳族硫酰亚胺或芳族磺酸的碱金属或碱土金属盐。
本发明的热塑性模塑组合物包括聚碳酸酯树脂和添加剂量的、确定量的稳定剂和盐。相对于组合物的重量,该稳定剂和盐的总添加量约为0.65-4.0%,条件是在盐的量是0.1%或更小的情况下,稳定剂的量大于0.5%。本发明组合物特征在于在1/16”厚的试样条件下,根据UL-94标准,它的可燃性等级至少为V-0。本发明组合物进一步的特征在于由该组合物模塑的制品事实上没有放射纹。放射纹表示表面缺陷,它显示为银纹,该银纹一般沿着模塑制品的流动方向。放射纹在黑色或深色组合物模塑的制品表面上特别显著。
用于制备本发明组合物的合适聚碳酸酯树脂是均聚碳酸酯和共聚碳酸酯及其混合物。
聚碳酸酯重均分子量一般为10,000-200,000,优选20,000-80,000,并且它们的熔体流动速率,按照ASTM D-1238在300℃测量,为约1到约65g/10min,优选约2到约15g/10min。例如,它们可以通过已知的两相界面方法从碳酸衍生物,如光气和二羟基化合物由缩聚方法制备(参见德国公开说明书2,063,050;2,063,052;1,570,703;2,211,956;2,211,957和2,248,817;法国专利1,561,518;和H.Schnell的专著,“聚碳酸酯的化学和物理”,Interscience出版社,纽约,纽约,1964,所有这些文献在此引入作为参考)。
在本发明中,适于制备本发明聚碳酸酯的二羟基化合物符合如下的结构通式(1)或(2)。
其中
A表示1-8个碳原子的亚烷基、2-8个碳原子的1,1-亚烷基、5-15个碳原子的亚环烷基、5-15个碳原子的1,1-亚环烷基、羰基、氧原子、硫原子、-SO-或-SO2-或符合下式的基团:
e和g都表示0-1的数;
Z表示F、Cl、Br或C1-C4烷基和如果几个Z基团是在一个芳族基团上的取代基,它们可以相同或彼此不同;
d表示0-4的整数;和
f表示0-3的整数。
适用于本发明的二羟基化合物是对苯二酚、间苯二酚、双-(羟苯基)-烷烃、双-(羟苯基)-醚、双-(羟苯基)-酮、双-(羟苯基)-亚砜、双-(羟苯基)-硫化物、双-(羟苯基)-砜、α,α-双-(羟苯基)-二异丙基-苯,以及它们的核烷基化化合物和二羟基二苯基环烷烃。这些和另外的合适芳族二羟基化合物描述在如下专利中,例如美国专利5,227,458;5,105,004;5,126,428;5,109,076;5,104,723;5,086,157;3,028,356;2,999,835;3,148,172;2,991,273;3,271,367和2,999,846,所有这些专利在此引入作为参考。
合适双酚的其它例子是2,2-双-(4-羟苯基)-丙烷(双酚A)、2,4-双-(4-羟苯基)-2-甲基-丁烷、1,1-双-(4-羟苯基)-环己烷、α,α’-双-(4-羟苯基)-对-二异丙苯、2,2-双-(3-甲基-4-羟苯基)-丙烷、2,2-双-(3-氯-4-羟苯基)-丙烷、双-(3,5-二甲基-4-羟苯基)-甲烷、2,2-双-(3,5-二甲基-4-羟苯基)-丙烷、双-(3,5-二甲基-4-羟苯基)-硫化物、双-(3,5-二甲基-4-羟苯基)-亚砜、双-(3,5-二甲基-4-羟苯基)-砜、二羟基二苯酮、2,4-双-(3,5-二甲基-4-羟苯基)-环己烷、α,α’-双-(3,5-二甲基-4-羟苯基)-对-二异丙苯和4,4’-磺酰二酚。
特别优选的芳族双酚的例子是2,2-双-(4-羟苯基)-丙烷、2,2-双-(3,5-二甲基-4-羟苯基)-丙烷、1,1-双-(4-羟苯基)-环己烷和1,1-双-(4-羟苯基)-3,3,5-三甲基环己烷。
最优选的双酚是2,2-双-(4-羟苯基)-丙烷(双酚A)。
本发明的聚碳酸酯可在它们的结构中包括衍生自一种或多种合适双酚的单元。
适用于本发明的树脂是酚酞基聚碳酸酯、共聚碳酸酯和三元聚碳酸酯,如在美国专利3,036,036和4,210,741中描述的那些,这两个专利在此引入作为参考。
也可以通过在其中缩合少量的,如0.05-2.0mol%(相对于双酚)的多羟基化合物而使本发明聚碳酸酯支化。
这种类型聚碳酸酯已经描述在如下文献中:例如德国公开说明书1,570,533;2,116,974和2,113,374;英国专利885,442和1,079,821和美国专利3,544,514。以下是可用于此目的的多羟基化合物的一些例子:间苯三酚、4,6-二甲基-2,4,6-三-(4-羟苯基)-庚烷、1,3,5-三-(4-羟苯基)-苯、1,1,1-三-(4-羟苯基)-乙烷、三-(4-羟苯基)-苯甲烷、2,2-双-[4,4-(4,4’-二羟基二苯基)]-环己基-丙烷、2,4-双-(4-羟基-1-异亚丙基)-苯酚、2,6-双-(2’-二羟基-5’-甲基苄基)-4-甲基-苯酚、2,4-二羟基苯甲酸、2-(4-羟苯基)-2-(2,4-二羟基-苯基)-丙烷和1,4-双-(4,4’-二羟基三苯基甲基)-苯。其它一些多官能化合物是2,4-二羟基-苯甲酸、1,3,5-苯三酸、氰尿酰氯和3,3-双-(4-羟苯基)-2-氧代-2,3-二氢吲哚。
除上述缩聚方法以外,用于制备本发明聚碳酸酯的方法是在均相中的缩聚和酯交换。合适的方法公开于在此引入作为参考的美国专利3,028,365;2,999,846;3,153,008和2,991,273中。
用于制备聚碳酸酯的优选方法是界面缩聚方法。
也可以使用其它合成方法以形成本发明的聚碳酸酯,如在美国专利3,912,688中公开的那些,该专利在此引入作为参考。
合适的聚碳酸酯树脂是市售的,例如Makrolon 2400、Makrolon2600、Makrolon 2800和Makrolon 3100,所有这些树脂都是双酚基均聚碳酸酯树脂,区别在于它们各自的分子量和特征在于它们按照ASTM D-1238的熔体流动指数(MFR)分别为约16.5-24,13-16,7.5-13.0和3.5-6.5g/10min。这些树脂是在宾夕法尼亚,匹兹堡的Bayer Corporation的产品。
适于本发明的聚碳酸酯树脂是已知的,它们的结构和制备方法已经描述在如下专利中:例如美国专利3,030,331、3,169,121、3,395,119、3,729,447、4,255,556、4,260,731、4,369,303、4,714,746和5,227,458,所有这些专利在此引入作为参考。
根据本发明的稳定剂是聚(甲基丙烯酸烷基酯)和氟化聚烯烃的物理混合物。合适稳定剂的制备包括共混聚(甲基丙烯酸烷基酯)的乳液和氟化聚烯烃的乳液。然后使用本领域技术人员公知的程序,将获得的乳液混合物凝聚或冷冻干燥,或喷雾干燥,以生产稳定剂。
聚(甲基丙烯酸烷基酯)是至少一种甲基丙烯酸C1-C15烷基酯的均聚物或共聚物。在它们的例子中,可以提及的是甲基丙烯酸甲酯、丁酯、癸酯、十二烷酯和十三烷酯。
适于本发明的氟化聚烯烃能形成乳液和在剪切时形成原纤。优选的氟化聚烯烃是聚四氟乙烯(PTFE)。合适的水中PTFE乳液的平均粒子尺寸为0.05-20微米,优选0.08-10微米,固体含量为约30-70wt%,优选50-60wt%。合适的PTFE乳液可从DuPont以Teflon30N购得。
合适的稳定剂包含约5-30wt%,优选10-20wt%的PTFE。适于本发明的稳定剂可从Mitsubishi Rayon Co.Ltd.以产品名MetablenTMA-3000购得。
适于本发明的盐包括全氟链烷磺酸的碱金属盐或碱土金属盐。这样的盐已经公开在美国专利3,775,367、4,469,833、4,626,563、4,626,563和4,649,168中,这些专利在此引入作为参考。
适于本发明的有机酸碱金属盐的例子是全氟丁磺酸钠或钾、全氟甲磺酸钠或钾、2,5-二氯苯磺酸钠或钾、2,4,5-三氯苯磺酸钠或钾、(4-氯苯基)膦酸钠或钾、甲基膦酸钠或钾、(2-苯基乙基)膦酸钠或钾、五氯苯甲酸钠或钾、2,4,6-三氯苯甲酸钠或钾、2,4-二氯苯甲酸钠或钾和苯基膦酸锂。
也包括如下已经在美国专利4,469,833中公开的盐,该专利在此引入作为参考:
(A)芳族硫化物的取代和未取代磺酸的碱金属和碱土金属盐;
(B)卤代环脂族芳族磺酸的碱金属和碱土金属盐;
(C)杂环化合物的磺酸碱金属和碱土金属盐;
(D)芳族酮的取代和未取代磺酸的碱金属和碱土金属盐;
(E)单体或聚合物芳族磺酸的碱金属和碱土金属盐;
(F)单体或聚合物取代的芳族磺酸的碱金属和碱土金属盐;
(G)单体或聚合物芳族酰胺磺酸的碱金属和碱土金属盐;
(H)芳族醚磺酸的碱金属和碱土金属盐;
(I)芳族羧酸的单体或聚合物磺酸的碱金属和碱土金属盐;和
(J)磺酸的单体或聚合物酚酯的碱金属和碱土金属盐。
以及,芳族硫酰亚胺的盐形式,包括如下物质的碱金属盐:糖精、N-(对甲苯磺酰基)-对甲苯硫酰亚胺、N-(N’-苄氨基-羰基)磺亚胺、N-(苯基羧基)磺亚胺、N-(2-嘧啶基)磺亚胺、N-(2-噻唑基)磺亚胺和其它硫酰亚胺的盐,这些盐公开在美国专利4,254,015中,该专利在此引入作为参考。
本发明组合物的制备是常规的和按照本领域公知的程序进行。除对于组合物是必须组分的盐和稳定剂以外,也可以包括其它添加剂,如填料、增强剂、颜料、染料、抗氧剂、热稳定剂、UV光吸收剂和脱模剂,所有这些添加剂的公认功能在本领域都是已知的,和按这样的已知功能量加入所有这些添加剂。
具体实施方式
通过以下实施例进一步说明本发明,而不限制本发明,其中除非另外特别说明,所有的份数和百分比按重量计。
按如下所述制备本发明组合物和评价它们的性能。将表中所示组分,以按百分比所示的量进行常规处理,和根据通常的程序和操作模塑测试样品。用于制备组合物的聚碳酸酯树脂是基于双酚-A的Makrolon 2608聚碳酸酯,它是Bayer的产品,它的熔体流动速率MFR(按照ASTM D 1238)约为10g/10min。如下所述的用于组合物的稳定剂是Metablen A-3000和使用的盐是全氟丁磺酸钾。以百分比所示的组分量是相对于组合物的重量。所有的组合物包含少量的常规脱模剂和炭黑,这两种物质对于本发明组合物都不是关键的。60度光泽值(光泽度)按照ASTM D2457测量,可燃性等级(可燃性)是在1/16”条件下按照UL-94确定。
为了说明本发明,以下所示的组合物包含变化量的稳定剂和盐。表1所示的组合物包含变化量的稳定剂和恒定量,0.1%的盐。
表1
实施例 | 1c | 2 | 3 | 4 | 5 |
组分 | |||||
聚碳酸酯 | 97.95 | 97.45 | 96.95 | 96.45 | 95.95 |
稳定剂 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 |
盐 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
性能: | |||||
MFR | 13.3 | 15.3 | 17.8 | 14.6 | 17 |
光泽度 | 104 | 102 | 103 | 102 | 101 |
可燃性 | V-2 | V-0 | V-0 | V-0 | V-0 |
c表示对比例。
制备了其中都包含0.2wt%盐的相应一套组合物并对它们进行评价,如表2所示。
表2
实施例 | 6 | 7 | 8 | 9 | 10 |
组分 | |||||
聚碳酸酯 | 97.85 | 97.35 | 96.85 | 96.35 | 95.85 |
稳定剂 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 |
盐 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 |
性能: | |||||
MFR | 13.8 | 15.7 | 19.3 | 13.9 | 18.2 |
光泽度 | 103 | 103 | 103 | 102 | 101 |
可燃性 | V-0 | V-0 | V-0 | V-0 | V-0 |
还制备了都包含0.3wt%盐的一套组合物并对它们进行评价,如表3所示。
表3
实施例 | 11 | 12 | 13 | 14 | 15 |
组分 | |||||
聚碳酸酯 | 97.75 | 97.25 | 96.75 | 96.25 | 95.75 |
稳定剂 | 0.5 | 1.0 | 1.5 | 2.0 | 2.5 |
盐 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 |
性能: | |||||
MFR | 13.7 | 15.6 | 14.1 | 13.6 | 13.2 |
光泽度 | 104 | 103 | 101 | 102 | 100 |
可燃性 | V-0 | V-0 | V-0 | V-0 | V-0 |
进行一系列试验以比较本发明组合物和不在本发明范围内的相应组合物,结果如下。聚碳酸酯树脂、稳定剂和盐如上所述,脱模剂和颜料也如上所述。结果见表4。
表4
实施例 | 16 | 17c | 18c | 19c |
组分 | ||||
聚碳酸酯 | 96.3 | 94.3 | 92.3 | 90.3 |
稳定剂 | 2.0 | 4.0 | 6.0 | 8.0 |
盐 | 0.25 | 0.25 | 0.25 | 0.25 |
性能: | ||||
MFR | 15.9 | 11.2 | 12.7 | 10.5 |
光泽度(平均) | 102 | 90 | 79 | 66 |
可燃性 | V-0 | V-1 | F* | F |
c表示对比例。
*F表示失败。
尽管在以上部分中为了说明本发明,已经对本发明进行了详细描述,应当理解这样的详细描述仅是为了说明的目的,其中可由本领域技术人员在不背离本发明精神和范围的情况下作出各种变化,它由权利要求所限定。
Claims (10)
1.一种热塑性模塑组合物,其包括聚碳酸酯树脂和添加剂量的、确定量的稳定剂和盐,其中相对于组合物的重量,该稳定剂和盐的总添加剂量为0.65-4.0%,条件是在盐的量是0.1%或更小的情况下,稳定剂的量大于0.5%,其中该稳定剂是聚(甲基丙烯酸烷基酯)和氟化聚烯烃的物理混合物,其中该氟化聚烯烃构成该物理混合物的5-30%,和其中该盐选自如下物质的至少一种:全氟链烷磺酸的碱金属盐、全氟链烷磺酸的碱土金属盐、芳族硫酰亚胺的碱金属盐、有机芳族磺酸的碱金属盐和芳族磺酸的碱土金属盐。
2.权利要求1的模塑组合物,其中所述氟化聚烯烃构成所述物理混合物的10-20%。
3.权利要求1的模塑组合物,其中所述聚碳酸酯树脂是基于双酚-A的均聚碳酸酯。
4.权利要求1的模塑组合物,其中聚(甲基丙烯酸烷基酯)是至少一种甲基丙烯酸C1-C15烷基酯的均聚物或共聚物。
5.权利要求4的模塑组合物,其中聚(甲基丙烯酸烷基酯)选自如下物质的至少一种:甲基丙烯酸甲酯、甲基丙烯酸丁酯、甲基丙烯酸癸酯、甲基丙烯酸十二烷酯和甲基丙烯酸十三烷酯。
6.权利要求1的热塑性模塑组合物,其中所述物理混合物是聚(甲基丙烯酸烷基酯)乳液和氟化聚烯烃乳液的干燥的共混物。
7.权利要求6的模塑组合物,其中氟化聚烯烃乳液的平均粒子尺寸为0.05-20微米。
8.权利要求6的模塑组合物,其中氟化聚烯烃乳液的平均粒子尺寸为0.08-10微米。
9.权利要求1的模塑组合物,其中所述盐选自如下物质的至少一种:全氟丁磺酸钠、全氟丁磺酸钾、全氟甲磺酸钠、全氟甲磺酸钾、2,5-二氯苯磺酸钠、2,5-二氯苯磺酸钾、2,4,5-三氯苯磺酸钠、2,4,5-三氯苯磺酸钾、(4-氯苯基)膦酸钠、(4-氯苯基)膦酸钾、甲基膦酸钠、甲基膦酸钾、(2-苯基乙基)膦酸钠、(2-苯基乙基)膦酸钾、五氯苯甲酸钠、五氯苯甲酸钾、2,4,6-三氯苯甲酸钠、2,4,6-三氯苯甲酸钾、2,4-二氯苯甲酸钠、2,4-二氯苯甲酸钾和苯基膦酸锂。
10.一种热塑性模塑组合物,其包括基于双酚-A的均聚碳酸酯树脂和添加剂量的、确定量的稳定剂和盐,其中相对于组合物的重量,该稳定剂和盐的总添加剂量为0.65-4.0%,条件是在盐的量是0.1%或更小的情况下,稳定剂的量大于0.5%,其中该稳定剂是至少一种甲基丙烯酸C1-C15烷基酯的均聚物或共聚物和氟化聚烯烃的物理混合物,其中该氟化聚烯烃构成该物理混合物重量的10-20%,和其中该盐选自如下物质的至少一种:全氟丁磺酸钠、全氟丁磺酸钾、全氟甲磺酸钠、全氟甲磺酸钾、2,5-二氯苯磺酸钠、2,5-二氯苯磺酸钾、2,4,5-三氯苯磺酸钠、2,4,5-三氯苯磺酸钾、(4-氯苯基)膦酸钠、(4-氯苯基)膦酸钾、甲基膦酸钠、甲基膦酸钾、(2-苯基乙基)膦酸钠、(2-苯基乙基)膦酸钾、五氯苯甲酸钠、五氯苯甲酸钾、2,4,6-三氯苯甲酸钠、2,4,6-三氯苯甲酸钾、2,4-二氯苯甲酸钠、2,4-二氯苯甲酸钾和苯基膦酸锂。
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US09/371,137 US6180702B1 (en) | 1999-08-09 | 1999-08-09 | Flame retardant polycarbonate composition |
US09/371,137 | 1999-08-09 |
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- 1999-08-09 US US09/371,137 patent/US6180702B1/en not_active Expired - Lifetime
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- 2000-08-04 CN CNB008111375A patent/CN1142981C/zh not_active Expired - Fee Related
- 2000-08-04 WO PCT/US2000/021443 patent/WO2001010957A1/en active IP Right Grant
- 2000-08-04 JP JP2001515756A patent/JP2003506553A/ja active Pending
- 2000-08-04 ES ES00952566T patent/ES2240138T3/es not_active Expired - Lifetime
- 2000-08-04 KR KR1020027001794A patent/KR100612802B1/ko not_active IP Right Cessation
- 2000-08-04 DE DE60019315T patent/DE60019315T2/de not_active Expired - Lifetime
- 2000-08-04 AU AU65240/00A patent/AU6524000A/en not_active Abandoned
- 2000-08-04 BR BR0013111-3A patent/BR0013111A/pt not_active IP Right Cessation
- 2000-08-04 EP EP00952566A patent/EP1214378B1/en not_active Expired - Lifetime
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HK1049495A1 (zh) | 2003-05-16 |
EP1214378A1 (en) | 2002-06-19 |
AU6524000A (en) | 2001-03-05 |
KR20020026569A (ko) | 2002-04-10 |
KR100612802B1 (ko) | 2006-08-18 |
BR0013111A (pt) | 2002-05-07 |
CN1367807A (zh) | 2002-09-04 |
DE60019315D1 (de) | 2005-05-12 |
EP1214378B1 (en) | 2005-04-06 |
ES2240138T3 (es) | 2005-10-16 |
JP2003506553A (ja) | 2003-02-18 |
DE60019315T2 (de) | 2006-03-09 |
CA2381294A1 (en) | 2001-02-15 |
TW527398B (en) | 2003-04-11 |
WO2001010957A1 (en) | 2001-02-15 |
US6180702B1 (en) | 2001-01-30 |
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