JP4500450B2 - 被覆組成物 - Google Patents
被覆組成物 Download PDFInfo
- Publication number
- JP4500450B2 JP4500450B2 JP2000591080A JP2000591080A JP4500450B2 JP 4500450 B2 JP4500450 B2 JP 4500450B2 JP 2000591080 A JP2000591080 A JP 2000591080A JP 2000591080 A JP2000591080 A JP 2000591080A JP 4500450 B2 JP4500450 B2 JP 4500450B2
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- composition
- methacrylate
- reaction
- free radical
- 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
Links
- 239000008199 coating composition Substances 0.000 title claims description 7
- 239000000178 monomer Substances 0.000 claims abstract description 63
- 239000003999 initiator Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000000654 additive Substances 0.000 claims abstract description 11
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 50
- 150000003254 radicals Chemical class 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 239000012972 dimethylethanolamine Substances 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- NQRFAUVGDLHPGH-UHFFFAOYSA-N 2-bromoheptanoic acid Chemical compound CCCCCC(Br)C(O)=O NQRFAUVGDLHPGH-UHFFFAOYSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 24
- 239000008346 aqueous phase Substances 0.000 abstract description 4
- 239000012084 conversion product Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- -1 thiocarbonylthio compound Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- ALXUOLQRSSGTMU-UHFFFAOYSA-N 6-(diethylamino)-2-methylhex-2-enamide Chemical compound CCN(CC)CCCC=C(C)C(N)=O ALXUOLQRSSGTMU-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- PJANXHGTPQOBST-QXMHVHEDSA-N cis-stilbene Chemical compound C=1C=CC=CC=1/C=C\C1=CC=CC=C1 PJANXHGTPQOBST-QXMHVHEDSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- NRYGCICLBPJWHA-KHPPLWFESA-N (z)-n'-decylbut-2-enediamide Chemical compound CCCCCCCCCCNC(=O)\C=C/C(N)=O NRYGCICLBPJWHA-KHPPLWFESA-N 0.000 description 1
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-O 1-ethenylimidazole;hydron Chemical class C=CN1C=C[NH+]=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-O 0.000 description 1
- WDRZVZVXHZNSFG-UHFFFAOYSA-N 1-ethenylpyridin-1-ium Chemical class C=C[N+]1=CC=CC=C1 WDRZVZVXHZNSFG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- BDKSYBXVYUGXIG-UHFFFAOYSA-N 2-(ethylamino)ethyl prop-2-enoate Chemical compound CCNCCOC(=O)C=C BDKSYBXVYUGXIG-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 1
- VETIYACESIPJSO-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOC(=O)C=C VETIYACESIPJSO-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- KAKQRSZHYGBPGR-UHFFFAOYSA-N 2-methylpropoxymethyl 2-methylprop-2-enoate Chemical compound CC(C)COCOC(=O)C(C)=C KAKQRSZHYGBPGR-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 1
- BQQGVSONEPNPAB-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound CCOC(OCC)[SiH2]CCCOC(=O)C(C)=C BQQGVSONEPNPAB-UHFFFAOYSA-N 0.000 description 1
- UIVRRNUEJAYDMX-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propyl prop-2-enoate Chemical compound CCOC(OCC)[SiH2]CCCOC(=O)C=C UIVRRNUEJAYDMX-UHFFFAOYSA-N 0.000 description 1
- HHHPYRGQUSPESB-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propyl prop-2-enoate Chemical compound COC(OC)[SiH2]CCCOC(=O)C=C HHHPYRGQUSPESB-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- OVORMUHCQPCYIW-UHFFFAOYSA-N 3-(propan-2-yloxymethylsilyl)propyl prop-2-enoate Chemical compound C(C=C)(=O)OCCC[SiH2]COC(C)C OVORMUHCQPCYIW-UHFFFAOYSA-N 0.000 description 1
- KIUQKRVLTQTVDR-UHFFFAOYSA-N 3-di(propan-2-yloxy)silylpropyl prop-2-enoate Chemical compound CC(C)O[SiH](OC(C)C)CCCOC(=O)C=C KIUQKRVLTQTVDR-UHFFFAOYSA-N 0.000 description 1
- DACWUGOLTNQROR-UHFFFAOYSA-N 3-diethoxysilylpropyl prop-2-enoate Chemical compound CCO[SiH](OCC)CCCOC(=O)C=C DACWUGOLTNQROR-UHFFFAOYSA-N 0.000 description 1
- HNVMCAHOYIOFAQ-UHFFFAOYSA-N 3-dimethoxysilylpropyl prop-2-enoate Chemical compound CO[SiH](OC)CCCOC(=O)C=C HNVMCAHOYIOFAQ-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- SDYYWRBMQSZLOC-UHFFFAOYSA-N 3-methyloxetane-2,4-dione Chemical compound CC1C(=O)OC1=O SDYYWRBMQSZLOC-UHFFFAOYSA-N 0.000 description 1
- NYUTUWAFOUJLKI-UHFFFAOYSA-N 3-prop-2-enoyloxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC(=O)C=C NYUTUWAFOUJLKI-UHFFFAOYSA-N 0.000 description 1
- ZJWCURYIRDLMTM-UHFFFAOYSA-N 3-tributoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOC(=O)C(C)=C ZJWCURYIRDLMTM-UHFFFAOYSA-N 0.000 description 1
- YFISHOAHNLGUEL-UHFFFAOYSA-N 3-tributoxysilylpropyl prop-2-enoate Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOC(=O)C=C YFISHOAHNLGUEL-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/06—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D157/00—Coating compositions based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D157/04—Copolymers in which only the monomer in minority is defined
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998160011 DE19860011A1 (de) | 1998-12-23 | 1998-12-23 | Beschichtungsmittel |
| DE19860011.9 | 1998-12-23 | ||
| DE1999109752 DE19909752A1 (de) | 1999-03-05 | 1999-03-05 | Beschichtungsmittel |
| DE19909752.6 | 1999-03-05 | ||
| PCT/EP1999/010335 WO2000039169A1 (de) | 1998-12-23 | 1999-12-22 | Beschichtungsmittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002533534A JP2002533534A (ja) | 2002-10-08 |
| JP2002533534A5 JP2002533534A5 (enExample) | 2006-12-14 |
| JP4500450B2 true JP4500450B2 (ja) | 2010-07-14 |
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| JP2000591080A Expired - Fee Related JP4500450B2 (ja) | 1998-12-23 | 1999-12-22 | 被覆組成物 |
Country Status (12)
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|---|---|
| US (1) | US6716905B1 (enExample) |
| EP (1) | EP1144462B1 (enExample) |
| JP (1) | JP4500450B2 (enExample) |
| KR (1) | KR100705531B1 (enExample) |
| AT (1) | ATE273325T1 (enExample) |
| AU (1) | AU771459B2 (enExample) |
| BR (1) | BR9916513A (enExample) |
| CA (1) | CA2355620A1 (enExample) |
| DE (1) | DE59910229D1 (enExample) |
| ES (1) | ES2228157T3 (enExample) |
| PL (1) | PL197702B1 (enExample) |
| WO (1) | WO2000039169A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19930067A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Beschichtungsstoff und seine Verwendung zur Herstellung von Füllerschichten und Steinschlagschutzgrundierungen |
| DE19930066A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Farb- und/oder effektgebende Mehrschichtlackierung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19930664A1 (de) | 1999-07-02 | 2001-01-11 | Basf Coatings Ag | Klarlack und seine Verwendung zur Herstellung von Klarlackierungen und farb- und/oder effektgebenden Mehrschichtlackierungen |
| DE19959923A1 (de) | 1999-12-11 | 2001-06-28 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19959927A1 (de) | 1999-12-11 | 2002-02-07 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10005819A1 (de) | 2000-02-10 | 2001-08-23 | Basf Coatings Ag | Wäßrige Primärdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10018078A1 (de) | 2000-04-12 | 2001-11-08 | Basf Coatings Ag | Formmassen und Verfahren zur Herstellung von Formkörpern |
| DE10018601A1 (de) | 2000-04-14 | 2001-10-25 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10029694A1 (de) | 2000-06-16 | 2001-12-20 | Basf Ag | Verwendung eines polymeren Umsetzungsprodukts |
| DE10029695A1 (de) * | 2000-06-16 | 2001-12-20 | Basf Ag | Verfahren zur Herstellung eines polymeren Umsetzungsprodukts |
| DE10106543A1 (de) * | 2001-02-13 | 2002-08-22 | Basf Ag | Beschichtungsmittelzusammensetzungen |
| DE10126651A1 (de) * | 2001-06-01 | 2002-12-12 | Basf Coatings Ag | Pulverlacksuspensionen (Pulverslurries) und Pulverlacke, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10206983A1 (de) * | 2002-02-20 | 2003-09-04 | Basf Coatings Ag | Verfahren zur Herstellung wässriger Dispersionen von Blockmischpolymerisaten |
| DE10235696B4 (de) * | 2002-08-03 | 2005-09-15 | Degussa Construction Chemicals Gmbh | Verfahren zur Herstellung von Homo-, Co- und Blockpolymeren |
| FR2846973B1 (fr) | 2002-11-07 | 2004-12-17 | Rhodia Chimie Sa | Composition d'antifroissage comprenant un copolymere a architecture controlee, pour articles en fibres textiles |
| DE102006053291A1 (de) * | 2006-11-13 | 2008-05-15 | Basf Coatings Ag | Lackschichtbildendes Korrosionsschutzmittel mit guter Haftung und Verfahren zu dessen stromfreier Applikation |
| FR2923487B1 (fr) * | 2007-11-09 | 2009-12-04 | Rhodia Operations | Copolymere ampholyte a architecture controlee |
| FR2917415B1 (fr) * | 2007-06-14 | 2012-10-12 | Rhodia Recherches Et Tech | Microgel polymerique comprenant des unites cationiques |
| FR2934154B1 (fr) * | 2008-07-23 | 2010-08-13 | Rhodia Operations | Emulsions thermosensibles |
| FR2937336B1 (fr) | 2008-10-22 | 2011-06-10 | Rhodia Operations | Composition pour les soins menagers comprenant un nanogel cationique |
| FR2987837B1 (fr) | 2012-03-09 | 2014-03-14 | Rhodia Operations | Polymerisation radicalaire controlee en dispersion eau-dans-l'eau |
| EP2896637A1 (en) | 2014-01-21 | 2015-07-22 | Rhodia Operations | Copolymer comprising units of type A deriving from carboxylic acid monomers and units of type B deriving from sulfonic acid monomers |
| US9840807B2 (en) | 2015-03-10 | 2017-12-12 | Charles Francis Luzon | Process for dyeing textiles, dyeing and fortifying rubber, and coloring and revitalizing plastics |
| KR102164100B1 (ko) | 2018-08-31 | 2020-10-12 | 주식회사 포스코 | Mg 함유 아연도금강판의 표면처리용 조성물 및 이를 이용하여 표면처리된 Mg 함유 아연도금강판 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656226A (en) | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
| ATE166363T1 (de) | 1991-02-06 | 1998-06-15 | Commw Scient Ind Res Org | Polymerisationsregelung |
| JP3080700B2 (ja) * | 1991-08-01 | 2000-08-28 | 三井化学株式会社 | 有芯多層構造エマルション粒子の製造方法 |
| JP3135151B2 (ja) * | 1991-12-12 | 2001-02-13 | 旭化成工業株式会社 | 共重合体ラテックスの製造方法 |
| JP3144874B2 (ja) * | 1992-03-03 | 2001-03-12 | 旭化成株式会社 | 共重合体ラテックス |
| US5264530A (en) * | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| CA2134868C (en) | 1992-05-01 | 2002-10-08 | Michael J. Darmon | Preparing crosslinkable polymers employing macromonomer chain transfer agents |
| FR2697840B1 (fr) | 1992-11-10 | 1994-12-02 | Rhone Poulenc Chimie | Utilisation de diènes comme agent de transfert lors de la préparation de polymères. |
| JPH083208A (ja) * | 1994-06-20 | 1996-01-09 | Nippon Steel Chem Co Ltd | 分子量調節剤 |
| AUPM930394A0 (en) * | 1994-11-09 | 1994-12-01 | Commonwealth Scientific And Industrial Research Organisation | Block copolymer synthesis |
| DE19508935A1 (de) * | 1995-03-13 | 1996-09-19 | Basf Ag | Flammgeschützte thermoplastische Formmassen, enthaltend als wesentliche Komponenten |
| AUPN585595A0 (en) | 1995-10-06 | 1995-11-02 | Commonwealth Scientific And Industrial Research Organisation | Control of molecular weight and end-group functionality in polymers |
| DE69709110T2 (de) | 1996-07-10 | 2002-04-25 | Commonwealth Scientific And Industrial Research Organisation, Clayton | Polymerisation mit "living" kennzeichen |
| US5723273A (en) * | 1996-09-11 | 1998-03-03 | Eastman Kodak Company | Protective overcoat for antistatic layer |
| US6316519B1 (en) | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| JPH1192509A (ja) * | 1997-09-18 | 1999-04-06 | Nippon Zeon Co Ltd | 共役ジエン系共重合体ラテックス、その製造方法およびこれを用いた紙塗工用組成物 |
| JPH11217409A (ja) * | 1997-11-21 | 1999-08-10 | Jsr Corp | 共重合体ラテックス |
| JPH11279336A (ja) * | 1998-01-29 | 1999-10-12 | Jsr Corp | 共重合体ラテックス |
| DE19930066A1 (de) * | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Farb- und/oder effektgebende Mehrschichtlackierung, Verfahren zu ihrer Herstellung und ihre Verwendung |
-
1999
- 1999-12-22 PL PL349439A patent/PL197702B1/pl not_active IP Right Cessation
- 1999-12-22 US US09/868,769 patent/US6716905B1/en not_active Expired - Lifetime
- 1999-12-22 CA CA002355620A patent/CA2355620A1/en not_active Abandoned
- 1999-12-22 WO PCT/EP1999/010335 patent/WO2000039169A1/de not_active Ceased
- 1999-12-22 KR KR1020017007772A patent/KR100705531B1/ko not_active Expired - Fee Related
- 1999-12-22 EP EP99965543A patent/EP1144462B1/de not_active Expired - Lifetime
- 1999-12-22 ES ES99965543T patent/ES2228157T3/es not_active Expired - Lifetime
- 1999-12-22 AT AT99965543T patent/ATE273325T1/de not_active IP Right Cessation
- 1999-12-22 DE DE59910229T patent/DE59910229D1/de not_active Expired - Lifetime
- 1999-12-22 AU AU21017/00A patent/AU771459B2/en not_active Ceased
- 1999-12-22 JP JP2000591080A patent/JP4500450B2/ja not_active Expired - Fee Related
- 1999-12-22 BR BR9916513-9A patent/BR9916513A/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002533534A (ja) | 2002-10-08 |
| EP1144462A1 (de) | 2001-10-17 |
| EP1144462B1 (de) | 2004-08-11 |
| AU771459B2 (en) | 2004-03-25 |
| ES2228157T3 (es) | 2005-04-01 |
| ATE273325T1 (de) | 2004-08-15 |
| WO2000039169A1 (de) | 2000-07-06 |
| KR100705531B1 (ko) | 2007-04-09 |
| BR9916513A (pt) | 2001-09-04 |
| CA2355620A1 (en) | 2000-07-06 |
| AU2101700A (en) | 2000-07-31 |
| DE59910229D1 (de) | 2004-09-16 |
| KR20010101308A (ko) | 2001-11-14 |
| PL349439A1 (en) | 2002-07-29 |
| PL197702B1 (pl) | 2008-04-30 |
| US6716905B1 (en) | 2004-04-06 |
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