ES2278783T3 - Masas de moldeo de poli(oximetileno) resistentes al impacto con pequeña emision, su utilizacion y cuerpos moldeados producidos a partir de ellas. - Google Patents
Masas de moldeo de poli(oximetileno) resistentes al impacto con pequeña emision, su utilizacion y cuerpos moldeados producidos a partir de ellas. Download PDFInfo
- Publication number
- ES2278783T3 ES2278783T3 ES01972066T ES01972066T ES2278783T3 ES 2278783 T3 ES2278783 T3 ES 2278783T3 ES 01972066 T ES01972066 T ES 01972066T ES 01972066 T ES01972066 T ES 01972066T ES 2278783 T3 ES2278783 T3 ES 2278783T3
- Authority
- ES
- Spain
- Prior art keywords
- component
- weight
- poly
- oxymethylene
- molding mass
- 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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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 238000000465 moulding Methods 0.000 title claims abstract description 44
- 229920006324 polyoxymethylene Polymers 0.000 claims abstract description 74
- -1 polyoxymethylene Polymers 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000003381 stabilizer Substances 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 31
- 229920001577 copolymer Polymers 0.000 claims description 23
- 229920000578 graft copolymer Polymers 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229920001971 elastomer Polymers 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 10
- 239000005060 rubber Substances 0.000 claims description 10
- 230000000977 initiatory effect Effects 0.000 claims description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 8
- 229920000877 Melamine resin Polymers 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 150000003927 aminopyridines Chemical class 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 claims description 3
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 claims description 3
- 229960000458 allantoin Drugs 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 claims description 3
- 238000011105 stabilization Methods 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- 229940091173 hydantoin Drugs 0.000 claims description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002356 single layer Substances 0.000 claims description 2
- 150000001565 benzotriazoles Chemical class 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940116351 sebacate Drugs 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
- 238000009757 thermoplastic moulding Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000000654 additive Substances 0.000 abstract description 6
- 239000003086 colorant Substances 0.000 abstract description 5
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 4
- 239000000194 fatty acid Substances 0.000 abstract description 4
- 229930195729 fatty acid Natural products 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 150000004665 fatty acids Chemical class 0.000 abstract description 3
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 9
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 7
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000002051 biphasic effect Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229920005601 base polymer Polymers 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 5
- 150000004292 cyclic ethers Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 235000019241 carbon black Nutrition 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 150000001934 cyclohexanes Chemical class 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical class O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229930182556 Polyacetal Natural products 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001279 poly(ester amides) Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- HCITUYXHCZGFEO-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.N=C1NC(=N)NC(=N)N1 HCITUYXHCZGFEO-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/04—Copolyoxymethylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
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- 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
- C08K5/13—Phenols; Phenolates
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/02—Polyacetals containing polyoxymethylene sequences only
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- 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)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10047488 | 2000-09-26 | ||
| DE10047488A DE10047488B4 (de) | 2000-09-26 | 2000-09-26 | Eingefärbte Polyoxymethylen-Formmassen und daraus hergestellte Formteile |
| DE2001126787 DE10126787A1 (de) | 2001-06-01 | 2001-06-01 | Schlagzähe Polyoxymethylen-Formmassen mit geringer Emission, ihre Verwendung und daraus hergestellter Formkörper |
| DE10126787 | 2001-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2278783T3 true ES2278783T3 (es) | 2007-08-16 |
Family
ID=26007159
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01969726T Expired - Lifetime ES2260283T3 (es) | 2000-09-26 | 2001-09-17 | Masas de moldeo teñidas de poli(oximetileno) y piezas moldeadas producidas a partir de ellas. |
| ES01972066T Expired - Lifetime ES2278783T3 (es) | 2000-09-26 | 2001-09-17 | Masas de moldeo de poli(oximetileno) resistentes al impacto con pequeña emision, su utilizacion y cuerpos moldeados producidos a partir de ellas. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01969726T Expired - Lifetime ES2260283T3 (es) | 2000-09-26 | 2001-09-17 | Masas de moldeo teñidas de poli(oximetileno) y piezas moldeadas producidas a partir de ellas. |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20030162912A1 (enExample) |
| EP (2) | EP1325078B1 (enExample) |
| JP (4) | JP5362165B2 (enExample) |
| AT (2) | ATE319774T1 (enExample) |
| AU (2) | AU2001291868A1 (enExample) |
| DE (2) | DE50111709D1 (enExample) |
| ES (2) | ES2260283T3 (enExample) |
| WO (2) | WO2002026884A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19936715A1 (de) * | 1999-08-06 | 2001-02-15 | Ticona Gmbh | Emissionsarme eingefärbte Polyoxymethylen-Formmassen |
| DE10047614C2 (de) | 2000-09-26 | 2003-03-27 | Generis Gmbh | Vorrichtung zum schichtweisen Aufbau von Modellen |
| WO2002026884A1 (de) * | 2000-09-26 | 2002-04-04 | Ticona Gmbh | Schlagzähe polyoxymethylen-formmassen mit geringer emission, ihre verwendung und daraus hergestellte formkörper |
| DE10238518A1 (de) * | 2002-08-21 | 2004-03-04 | Ticona Gmbh | Verschleißfeste Polyoxymethylen Formmassen und deren Verwendung |
| WO2005033201A1 (ja) | 2003-10-01 | 2005-04-14 | Polyplastics Co., Ltd. | ポリアセタール樹脂組成物 |
| US20050080185A1 (en) * | 2003-10-10 | 2005-04-14 | Mhetar Vijay R. | Poly(arylene ether) composition and method of making |
| WO2005040275A1 (ja) * | 2003-10-24 | 2005-05-06 | Asahi Kasei Chemicals Corporation | ポリアセタール樹脂組成物及びその成形品 |
| JP4516301B2 (ja) * | 2003-11-10 | 2010-08-04 | ポリプラスチックス株式会社 | ポリアセタール樹脂組成物 |
| KR100523361B1 (ko) * | 2003-12-22 | 2005-10-24 | 한국엔지니어링플라스틱 주식회사 | 내연료성이 우수한 폴리옥시메틸렌 조성물과 이의 성형품 |
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| JP4815144B2 (ja) * | 2005-04-01 | 2011-11-16 | ジャパンコンポジット株式会社 | ラジカル硬化性樹脂組成物 |
| US7645821B2 (en) | 2005-07-28 | 2010-01-12 | Ticona Gmbh | Low-emission, tribologically modified polyoxymethylene molding compositions and moldings produced therefrom |
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| DE602008003131D1 (en) * | 2007-07-19 | 2010-12-02 | Ticona Llc | Stabilisierte thermoplastische copolyester |
| US20090048388A1 (en) * | 2007-08-16 | 2009-02-19 | Elia Andri E | Wear resistant toughened and reinforced polyacetal compositions |
| JP5297640B2 (ja) * | 2007-11-29 | 2013-09-25 | ポリプラスチックス株式会社 | 耐酸性に優れたポリアセタール樹脂成形品 |
| JP5320222B2 (ja) | 2008-09-03 | 2013-10-23 | 三菱エンジニアリングプラスチックス株式会社 | ポリアセタール樹脂組成物、樹脂成形品、ポリアセタール樹脂原料組成物の改質方法及び改質剤 |
| EP2177155A1 (de) * | 2008-10-20 | 2010-04-21 | F. Hoffmann-Roche AG | Analytisches Testbandinstrument mit Gleichstrommotor und Getriebe |
| US8110632B2 (en) * | 2009-01-15 | 2012-02-07 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether) articles and compositions |
| ATE551389T1 (de) * | 2009-08-07 | 2012-04-15 | Ticona Llc | Polyacetalzusammensetzung mit geringer formaldeyd-emission |
| US9090769B2 (en) | 2011-04-05 | 2015-07-28 | Ticona Llc | Molded articles having a swirl-like or marble-like appearance and compositions for producing same |
| US9296874B2 (en) * | 2011-04-28 | 2016-03-29 | Ticona Llc | Polyacetal compositions and molded products made therefrom |
| EP2760927A1 (en) | 2011-09-29 | 2014-08-06 | Ticona LLC | Polymer composition for producing articles having a metallic appearance |
| WO2013094393A1 (ja) * | 2011-12-21 | 2013-06-27 | 三菱瓦斯化学株式会社 | 樹脂組成物および成形体 |
| US20140179840A1 (en) * | 2012-12-26 | 2014-06-26 | Ticona Llc | Low Emission, UV Stabilized High Strength Acetal Copolymer |
| WO2014105758A2 (en) * | 2012-12-26 | 2014-07-03 | Ticona Llc | Stabilized polymer composition containing an impact modifier |
| CN105793353B (zh) * | 2013-10-21 | 2019-06-18 | 提克纳有限公司 | 固有低摩擦聚甲醛 |
| JP2015101599A (ja) | 2013-11-21 | 2015-06-04 | ポリプラスチックス株式会社 | ポリオキシメチレン樹脂組成物の製造方法 |
| TWI488911B (zh) * | 2014-04-18 | 2015-06-21 | Fdc Lees Chemical Industry Co | 用於聚甲醛之無三聚氰胺複合式添加劑 |
| WO2016034668A1 (en) | 2014-09-05 | 2016-03-10 | Sabic Global Technologies B.V. | Polyoxymethylene compositions, method for manufacture, and articles made therefrom |
| WO2016136726A1 (ja) | 2015-02-25 | 2016-09-01 | 三菱レイヨン株式会社 | 樹脂組成物及びその成形体 |
| JP6853020B2 (ja) * | 2015-12-11 | 2021-03-31 | 旭化成株式会社 | ポリアセタール樹脂用顆粒状組成物、及びポリアセタール樹脂組成物 |
| WO2017156053A1 (en) * | 2016-03-08 | 2017-09-14 | Ticona Llc | Orthopedic device and polymer compositions for making same |
| CN108699321B (zh) * | 2016-04-13 | 2020-11-24 | 株式会社钟化 | 强韧化环氧树脂组合物 |
| WO2018069838A1 (en) | 2016-10-11 | 2018-04-19 | Celanese Sales Germany Gmbh | Wear resistant polymer composition having improved surface appearance |
| CN120966191A (zh) | 2017-05-05 | 2025-11-18 | 提克纳有限责任公司 | 耐化学性的聚甲醛聚合物组合物 |
| KR102474348B1 (ko) | 2017-11-30 | 2022-12-05 | 현대자동차 주식회사 | 폴리 옥시 메틸렌 수지 조성물 및 이로부터 제조된 성형품 |
| CN112236295A (zh) * | 2018-05-03 | 2021-01-15 | 塞拉尼斯销售德国有限公司 | 用于医疗技术应用的整体着色的聚合物组合物 |
| EP3802697A4 (en) * | 2018-06-04 | 2022-02-23 | Celanese International Corporation | COMPOSITION OF POLYOXY METHYLENE IN FOOD HANDLING APPLICATIONS |
| JPWO2021002315A1 (enExample) * | 2019-07-03 | 2021-01-07 | ||
| JPWO2021002314A1 (enExample) * | 2019-07-03 | 2021-01-07 | ||
| WO2021002316A1 (ja) * | 2019-07-03 | 2021-01-07 | 三菱エンジニアリングプラスチックス株式会社 | 樹脂組成物および成形品 |
| JP7257293B2 (ja) * | 2019-08-30 | 2023-04-13 | ポリプラスチックス株式会社 | ポリアセタール樹脂組成物及びその製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3151814A1 (de) * | 1981-12-29 | 1983-07-07 | Hoechst Ag, 6230 Frankfurt | "fuellstoff enthaltende kunststoff-formmasse, verfahren zu ihrer herstellung sowie deren verwendung" |
| JPS5996157A (ja) * | 1982-11-25 | 1984-06-02 | Polyplastics Co | ポリアセタ−ル樹脂組成物 |
| DE3505524A1 (de) | 1984-03-28 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Schlagzaeh modifiziertes polyoxymethylen und daraus hergestellte formkoerper |
| US5183858A (en) * | 1989-03-31 | 1993-02-02 | Takeda Chemical Industries, Ltd. | Core-shell polymer, production and use thereof |
| JP2993062B2 (ja) * | 1990-07-02 | 1999-12-20 | 三菱瓦斯化学株式会社 | オキシメチレン共重合体組成物 |
| JPH0692476B2 (ja) * | 1990-10-05 | 1994-11-16 | 旭化成工業株式会社 | 安定化ポリオキシメチレンの製造法 |
| JP3024802B2 (ja) * | 1991-02-04 | 2000-03-27 | ポリプラスチックス株式会社 | ポリアセタール樹脂着色組成物 |
| JP3088159B2 (ja) * | 1991-12-04 | 2000-09-18 | ポリプラスチックス株式会社 | ポリアセタール成形体 |
| JPH06136234A (ja) * | 1992-10-28 | 1994-05-17 | Polyplastics Co | ポリオキシメチレン組成物 |
| EP0605736A1 (en) * | 1992-06-30 | 1994-07-13 | Polyplastics Co. Ltd. | Polyoxymethylene composition |
| DE4229760A1 (de) * | 1992-09-05 | 1994-03-10 | Basf Ag | UV-stabilisierte Polyoxymethylenformmassen |
| DE4236465A1 (de) * | 1992-10-24 | 1994-04-28 | Degussa | Polyoxymethylen mit verbesserter Stabilität gegen Säuren, Verfahren zu seiner Herstellung sowie Verwendung |
| JP3140618B2 (ja) * | 1993-09-02 | 2001-03-05 | ポリプラスチックス株式会社 | ポリアセタール樹脂組成物 |
| JP3399483B2 (ja) * | 1993-12-21 | 2003-04-21 | 三菱瓦斯化学株式会社 | オキシメチレン共重合体樹脂組成物 |
| EP0668317A1 (en) * | 1994-02-15 | 1995-08-23 | Rohm And Haas Company | Impact modified polyacetal compositions |
| JPH07268180A (ja) * | 1994-03-30 | 1995-10-17 | Polyplastics Co | ポリオキシメチレン組成物 |
| JP3374874B2 (ja) * | 1994-06-07 | 2003-02-10 | 三菱瓦斯化学株式会社 | オキシメチレン共重合体樹脂組成物の製造方法 |
| MY114026A (en) * | 1995-09-01 | 2002-07-31 | Asahi Chemical Ind | Polyacetal resin molded article and process for producing the same |
| JP3808101B2 (ja) * | 1995-09-29 | 2006-08-09 | 旭化成ケミカルズ株式会社 | ポリアセタール樹脂組成物 |
| US6147146A (en) * | 1996-11-13 | 2000-11-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Resin composition |
| DE69727834T2 (de) * | 1996-12-27 | 2005-01-13 | Polyplastics Co. Ltd. | Polyacetalharz-zusammensetzung und pressteile |
| DE19803227B4 (de) * | 1998-01-27 | 2007-06-21 | Ticona Gmbh | Farbmittelzubereitung zur Einfärbung von Polyoxymethylen-Formmassen |
| JP4167341B2 (ja) * | 1998-03-25 | 2008-10-15 | ポリプラスチックス株式会社 | ポリアセタール樹脂組成物およびその製造方法 |
| JP4418553B2 (ja) * | 1998-05-07 | 2010-02-17 | ポリプラスチックス株式会社 | ポリアセタール樹脂組成物 |
| DE19828797A1 (de) * | 1998-06-27 | 1999-12-30 | Basf Ag | Stabilisierte Polyoxymethylen-Formmassen |
| US5962623A (en) * | 1998-09-08 | 1999-10-05 | Ticona Gmbh | Process for the preparation of polyacetal copolymers |
| WO2002026884A1 (de) * | 2000-09-26 | 2002-04-04 | Ticona Gmbh | Schlagzähe polyoxymethylen-formmassen mit geringer emission, ihre verwendung und daraus hergestellte formkörper |
-
2001
- 2001-09-17 WO PCT/EP2001/010710 patent/WO2002026884A1/de not_active Ceased
- 2001-09-17 DE DE50111709T patent/DE50111709D1/de not_active Expired - Lifetime
- 2001-09-17 JP JP2002530653A patent/JP5362165B2/ja not_active Expired - Lifetime
- 2001-09-17 EP EP01969726A patent/EP1325078B1/de not_active Expired - Lifetime
- 2001-09-17 AU AU2001291868A patent/AU2001291868A1/en not_active Abandoned
- 2001-09-17 US US10/381,501 patent/US20030162912A1/en not_active Abandoned
- 2001-09-17 DE DE50109172T patent/DE50109172D1/de not_active Expired - Lifetime
- 2001-09-17 ES ES01969726T patent/ES2260283T3/es not_active Expired - Lifetime
- 2001-09-17 EP EP01972066A patent/EP1339794B1/de not_active Expired - Lifetime
- 2001-09-17 WO PCT/EP2001/010711 patent/WO2002026885A1/de not_active Ceased
- 2001-09-17 AU AU2001289888A patent/AU2001289888A1/en not_active Abandoned
- 2001-09-17 ES ES01972066T patent/ES2278783T3/es not_active Expired - Lifetime
- 2001-09-17 AT AT01969726T patent/ATE319774T1/de not_active IP Right Cessation
- 2001-09-17 JP JP2002530654A patent/JP2004522810A/ja active Pending
- 2001-09-17 AT AT01972066T patent/ATE348860T1/de not_active IP Right Cessation
-
2008
- 2008-05-22 US US12/125,603 patent/US8053499B2/en not_active Expired - Lifetime
-
2012
- 2012-08-10 JP JP2012178198A patent/JP2012237010A/ja active Pending
- 2012-08-10 JP JP2012178174A patent/JP5355763B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20080287580A1 (en) | 2008-11-20 |
| US20030162912A1 (en) | 2003-08-28 |
| EP1325078A1 (de) | 2003-07-09 |
| AU2001289888A1 (en) | 2002-04-08 |
| EP1339794B1 (de) | 2006-12-20 |
| JP2012237010A (ja) | 2012-12-06 |
| JP2004522810A (ja) | 2004-07-29 |
| ATE319774T1 (de) | 2006-03-15 |
| AU2001291868A1 (en) | 2002-04-08 |
| WO2002026884A1 (de) | 2002-04-04 |
| EP1339794A1 (de) | 2003-09-03 |
| JP2004510024A (ja) | 2004-04-02 |
| WO2002026885A1 (de) | 2002-04-04 |
| JP2012237009A (ja) | 2012-12-06 |
| ES2260283T3 (es) | 2006-11-01 |
| US8053499B2 (en) | 2011-11-08 |
| DE50109172D1 (de) | 2006-05-04 |
| EP1325078B1 (de) | 2006-03-08 |
| JP5355763B2 (ja) | 2013-11-27 |
| DE50111709D1 (de) | 2007-02-01 |
| ATE348860T1 (de) | 2007-01-15 |
| JP5362165B2 (ja) | 2013-12-11 |
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