DE3116995C2 - - Google Patents
Info
- Publication number
- DE3116995C2 DE3116995C2 DE3116995A DE3116995A DE3116995C2 DE 3116995 C2 DE3116995 C2 DE 3116995C2 DE 3116995 A DE3116995 A DE 3116995A DE 3116995 A DE3116995 A DE 3116995A DE 3116995 C2 DE3116995 C2 DE 3116995C2
- Authority
- DE
- Germany
- Prior art keywords
- core
- polymer
- shell
- polymer latices
- latices
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000126 latex Polymers 0.000 claims abstract description 143
- 239000004816 latex Substances 0.000 claims abstract description 85
- 229920000642 polymer Polymers 0.000 claims abstract description 60
- 239000002245 particle Substances 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000011258 core-shell material Substances 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 10
- 239000002861 polymer material Substances 0.000 claims abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 61
- 239000006185 dispersion Substances 0.000 claims description 35
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 108090000790 Enzymes Proteins 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 3
- 239000007850 fluorescent dye Substances 0.000 claims description 3
- 229920006037 cross link polymer Polymers 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 230000006855 networking Effects 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 230000003100 immobilizing effect Effects 0.000 claims 1
- 229920002521 macromolecule Polymers 0.000 claims 1
- 239000011162 core material Substances 0.000 abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 40
- 238000000034 method Methods 0.000 abstract description 19
- 239000013543 active substance Substances 0.000 abstract description 10
- 125000000524 functional group Chemical group 0.000 abstract description 5
- 229940088623 biologically active substance Drugs 0.000 abstract 2
- 238000010276 construction Methods 0.000 abstract 1
- 239000011257 shell material Substances 0.000 description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- -1 thiocarbonyldioxy Chemical group 0.000 description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 239000008363 phosphate buffer Substances 0.000 description 11
- HMHYBQHINBJJGL-UHFFFAOYSA-N 4-[(4-carboxy-4-cyanobutan-2-yl)diazenyl]-2-cyanopentanoic acid Chemical class N#CC(C(O)=O)CC(C)N=NC(C)CC(C#N)C(O)=O HMHYBQHINBJJGL-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 8
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 7
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 7
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 7
- 102000004142 Trypsin Human genes 0.000 description 6
- 108090000631 Trypsin Proteins 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 239000012588 trypsin Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 230000004520 agglutination Effects 0.000 description 5
- 239000012876 carrier material Substances 0.000 description 5
- 239000005018 casein Substances 0.000 description 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
- 235000021240 caseins Nutrition 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000000466 oxiranyl group Chemical group 0.000 description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000008105 immune reaction Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- AYFACLKQYVTXNS-UHFFFAOYSA-M sodium;tetradecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCS([O-])(=O)=O AYFACLKQYVTXNS-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-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
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 102000011022 Chorionic Gonadotropin Human genes 0.000 description 2
- 108010062540 Chorionic Gonadotropin Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ICCKYZGDUAOTHD-UHFFFAOYSA-L disodium;4-[(4-carboxylato-2-cyanobutan-2-yl)diazenyl]-4-cyanopentanoate Chemical compound [Na+].[Na+].[O-]C(=O)CCC(C)(C#N)N=NC(C)(CCC([O-])=O)C#N ICCKYZGDUAOTHD-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LADVVLNKOIYKBB-UHFFFAOYSA-N (2,4,5-trichlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC(Cl)=C(Cl)C=C1Cl LADVVLNKOIYKBB-UHFFFAOYSA-N 0.000 description 1
- FXERIFIBVKHTHC-UHFFFAOYSA-N (4-methylsulfinylphenyl) 2-methylprop-2-enoate Chemical compound CS(=O)C1=CC=C(C=C1)OC(C(=C)C)=O FXERIFIBVKHTHC-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- VZZPYUKWXDLMGI-UHFFFAOYSA-N 1,6-diisothiocyanatohexane Chemical compound S=C=NCCCCCCN=C=S VZZPYUKWXDLMGI-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- FYNMFSNWQPJEDO-UHFFFAOYSA-N 2-(2,4,6-tribromophenoxy)butyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCC(CC)OC1=C(C=C(C=C1Br)Br)Br FYNMFSNWQPJEDO-UHFFFAOYSA-N 0.000 description 1
- UBDUTFCZTZGGCC-UHFFFAOYSA-N 2-(2,4,6-tribromophenoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=C(Br)C=C(Br)C=C1Br UBDUTFCZTZGGCC-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- XNQDKIWPZVPVQD-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)ethanesulfonic acid Chemical class CC(=C)C(=O)NCCS(O)(=O)=O XNQDKIWPZVPVQD-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical class CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Pathology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813116995 DE3116995A1 (de) | 1981-04-29 | 1981-04-29 | Latex zur immobilisierung von biologisch wirksamen substanzen |
| AT82100784T ATE19524T1 (de) | 1981-04-29 | 1982-02-04 | Latex zur immobilisierung von biologisch wirksamen substanzen. |
| EP82100784A EP0065069B1 (de) | 1981-04-29 | 1982-02-04 | Latex zur Immobilisierung von biologisch wirksamen Substanzen |
| DK144382A DK163668C (da) | 1981-04-29 | 1982-03-30 | Polymerpartikler med kerne-skal-opbygning, der er redispergerbare i en vaeske til dannelse af en latex til brug ved immobilisering af biologisk aktive stoffer |
| JP57070541A JPH0613611B2 (ja) | 1981-04-29 | 1982-04-28 | 水性媒体と抗体又は酵素を固定するための核―外皮構造を有するポリマー粒子とからなるポリマーラテックス |
| MX192489A MX160019A (es) | 1981-04-29 | 1982-04-29 | Un proceso para la produccion de particulas de polimero,redispersable en un liquido para formar una dispersion y capaz de unirse covalentemente a substancias bilogicas por si mismo |
| US06/930,023 US4710525A (en) | 1981-04-29 | 1986-11-07 | Polymer particles and latices thereof for the immobilization of biologically active substances |
| US07/075,416 US4829101A (en) | 1981-04-29 | 1987-07-20 | Polymer particles and latices thereof for the immobilization of biologically active substances |
| JP2263967A JPH0723893B2 (ja) | 1981-04-29 | 1990-10-03 | 抗体の固定法 |
| JP4125759A JP2536995B2 (ja) | 1981-04-29 | 1992-05-19 | 酵素固定法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813116995 DE3116995A1 (de) | 1981-04-29 | 1981-04-29 | Latex zur immobilisierung von biologisch wirksamen substanzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3116995A1 DE3116995A1 (de) | 1982-11-25 |
| DE3116995C2 true DE3116995C2 (en, 2012) | 1990-08-09 |
Family
ID=6131085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813116995 Granted DE3116995A1 (de) | 1981-04-29 | 1981-04-29 | Latex zur immobilisierung von biologisch wirksamen substanzen |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4710525A (en, 2012) |
| EP (1) | EP0065069B1 (en, 2012) |
| JP (3) | JPH0613611B2 (en, 2012) |
| AT (1) | ATE19524T1 (en, 2012) |
| DE (1) | DE3116995A1 (en, 2012) |
| DK (1) | DK163668C (en, 2012) |
| MX (1) | MX160019A (en, 2012) |
Families Citing this family (69)
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|---|---|---|---|---|
| DE3145082A1 (de) * | 1981-11-13 | 1983-05-19 | Behringwerke Ag, 3550 Marburg | "ein latex, biologisch aktive latexkonjugate und verfahren zu ihrer herstellung" |
| US4828996A (en) * | 1983-01-04 | 1989-05-09 | Rolf Siegel | Materials and method for immobilizing biologically active substances |
| EP0164889A3 (en) * | 1984-05-07 | 1986-12-17 | HSC Research Development Corporation | Surface-treated polymeric substrates |
| US5225279A (en) * | 1985-04-30 | 1993-07-06 | Rohm And Haas Company | Solvent core encapsulant composition |
| US4677003A (en) * | 1985-04-30 | 1987-06-30 | Rohm And Haas Company | Microsuspension process for preparing solvent core sequential polymer dispersion |
| DE3530312A1 (de) * | 1985-08-24 | 1987-02-26 | Guenther Dr Sawatzki | Traeger fuer die photometrische immunspezifische bestimmung von antigenen oder antikoerpern, verfahren zu ihrer herstellung und verwendung |
| DE3621719A1 (de) * | 1986-06-28 | 1988-01-14 | Roehm Gmbh | Verfahren zur ausloesung der bildung von antikoerpern |
| DE3622993A1 (de) * | 1986-07-09 | 1988-01-21 | Behringwerke Ag | Dispersionspolymere, biologisch aktive dispersionspolymere, verfahren zu ihrer herstellung und verwendung als diagnostisches mittel |
| DE3850981T2 (de) * | 1987-02-27 | 1995-03-30 | Eastman Kodak Co | Wasserunlösliches Teilchen und immunoreaktives Reagens, analytische Elemente und Verfahren zu ihrer Verwendung. |
| US4997772A (en) * | 1987-09-18 | 1991-03-05 | Eastman Kodak Company | Water-insoluble particle and immunoreactive reagent, analytical elements and methods of use |
| JPH01104621A (ja) * | 1987-09-18 | 1989-04-21 | Eastman Kodak Co | ポリマーラテックス組成物の製造方法 |
| US4810763A (en) * | 1987-12-23 | 1989-03-07 | Avery International Corporation | Suspension polymerization in an organic medium |
| DE3811042A1 (de) * | 1988-03-31 | 1989-10-19 | Merck Patent Gmbh | Ionenaustauscher |
| US5258454A (en) * | 1988-09-01 | 1993-11-02 | Riso National Laboratory | Peptide synthesis method and solid support for use in the method |
| EP0406404B1 (fr) * | 1989-01-20 | 1994-06-22 | Diagnostica Stago | Particules sumicroniques, preparation et utilisation dans l'immunodiagnostic |
| US4990279A (en) * | 1989-04-21 | 1991-02-05 | Hercules Incorporated | Electrorheological fluids |
| EP0397439B1 (en) * | 1989-05-10 | 1995-03-15 | Nippon Zeon Co., Ltd. | Vinyl chloride resin for safety glass and process for preparation of the resin |
| US6120805A (en) * | 1990-04-06 | 2000-09-19 | Rhone-Poulenc Rorer Sa | Microspheres, process for their preparation and their use |
| US5216130A (en) * | 1990-05-17 | 1993-06-01 | Albany Medical College | Complex for in-vivo target localization |
| US5086143A (en) * | 1990-07-25 | 1992-02-04 | Eastman Kodak Company | Copolymers containing polyoxyalkylene side chains |
| US5200315A (en) * | 1990-07-25 | 1993-04-06 | Eastman Kodak Company | Particulate biologically active reagent containing polyoxyalkylene side chains, analytical element and methods for use of the reagent |
| DE4026992A1 (de) * | 1990-08-25 | 1992-02-27 | Roehm Gmbh | Verfahren zur herstellung von traegersystemen fuer biologisch aktive materialien |
| US5200471A (en) * | 1990-11-05 | 1993-04-06 | Minnesota Mining And Manufacturing Company | Biomolecules covalently immobilized with a high bound specific biological activity and method of preparing same |
| US5308749A (en) * | 1991-01-25 | 1994-05-03 | Eastman Kodak Company | Method of preparing biologically active reagents from succinimide-containing polymers, analytical element and methods of use |
| US5200462A (en) * | 1991-01-25 | 1993-04-06 | Eastman Kodak Company | Succinimide containing polymers and lattices prepared from same |
| US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
| US5385959A (en) * | 1992-04-29 | 1995-01-31 | Lever Brothers Company, Division Of Conopco, Inc. | Capsule which comprises a component subject to degradation and a composite polymer |
| DK168670B1 (da) * | 1993-03-09 | 1994-05-16 | Niro Separation As | Apparat til fordeling af fibre |
| US5461125A (en) * | 1993-04-30 | 1995-10-24 | Minnesota Mining And Manufacturing Company | Waterborne core-shell latex polymers |
| EP0708919B1 (de) * | 1993-07-16 | 1998-09-16 | MERCK PATENT GmbH | Trennmaterialien für die hydrophobe chromatographie |
| DE4333674A1 (de) * | 1993-10-02 | 1995-04-06 | Merck Patent Gmbh | Nukleotidhaltiges Sorbens für die Affinitätschromatographie |
| DE4333821A1 (de) * | 1993-10-04 | 1995-04-06 | Merck Patent Gmbh | Ionenaustauscher |
| DE4334353A1 (de) * | 1993-10-08 | 1995-04-13 | Merck Patent Gmbh | Verfahren und Träger für die Gelpermeationschromatographie |
| US5432210A (en) * | 1993-11-22 | 1995-07-11 | Rohm And Haas Company | Polymer particles and method for preparing by polymerization of encapsulated monomers |
| US5776651A (en) * | 1996-01-31 | 1998-07-07 | Minnesota Mining & Manufacturing Company | Laminable proofing elements |
| EP2290364A1 (en) | 1996-04-25 | 2011-03-02 | BioArray Solutions Ltd. | Light-controlled electrokinetic assembly of particles near surfaces |
| US6057384A (en) | 1997-10-31 | 2000-05-02 | Hewlett-Packard Company | Latex polymer blends for improving the permanence of ink-jet inks |
| US6417249B1 (en) | 1997-10-31 | 2002-07-09 | Hewlett-Packard Company | Ink-jet printing ink compositions having superior smear-fastness |
| US5990202A (en) * | 1997-10-31 | 1999-11-23 | Hewlett-Packard Company | Dual encapsulation technique for preparing ink-jets inks |
| AU5154000A (en) * | 1999-05-19 | 2000-12-05 | Brigham Young University | Stabilization and acoustic activation of polymeric micelles for drug delivery |
| EP1311839B1 (en) | 2000-06-21 | 2006-03-01 | Bioarray Solutions Ltd | Multianalyte molecular analysis using application-specific random particle arrays |
| US9709559B2 (en) | 2000-06-21 | 2017-07-18 | Bioarray Solutions, Ltd. | Multianalyte molecular analysis using application-specific random particle arrays |
| AU2001296480A1 (en) * | 2000-10-02 | 2002-04-15 | Kimberly-Clark Worldwide, Inc. | Recording medium with nanoparticles and methods of making the same |
| US7262063B2 (en) * | 2001-06-21 | 2007-08-28 | Bio Array Solutions, Ltd. | Directed assembly of functional heterostructures |
| CA2741049C (en) | 2001-10-15 | 2019-02-05 | Bioarray Solutions, Ltd. | Multiplexed analysis of polymorphic loci by probe elongation-mediated detection |
| US6792019B2 (en) * | 2002-02-28 | 2004-09-14 | Texas Instruments Incorporated | Driver with tail currents in discrete subranges |
| US7526114B2 (en) | 2002-11-15 | 2009-04-28 | Bioarray Solutions Ltd. | Analysis, secure access to, and transmission of array images |
| US6964747B2 (en) * | 2003-01-21 | 2005-11-15 | Bioarray Solutions, Ltd. | Production of dyed polymer microparticles |
| US7255895B2 (en) * | 2003-01-21 | 2007-08-14 | Bioarray Solutions, Ltd. | Method for controlling solute loading of polymer microparticles |
| JP3954522B2 (ja) * | 2003-04-18 | 2007-08-08 | 日清紡績株式会社 | 生物学的活性物質を固定化した素子 |
| US7927796B2 (en) | 2003-09-18 | 2011-04-19 | Bioarray Solutions, Ltd. | Number coding for identification of subtypes of coded types of solid phase carriers |
| PT1664722E (pt) | 2003-09-22 | 2011-12-28 | Bioarray Solutions Ltd | Polielectrólito imobilizado à superfície com grupos funcionais múltiplos capazes de se ligarem covalentemente às biomoléculas |
| CA2544041C (en) | 2003-10-28 | 2015-12-08 | Bioarray Solutions Ltd. | Optimization of gene expression analysis using immobilized capture probes |
| WO2005045060A2 (en) | 2003-10-29 | 2005-05-19 | Bioarray Solutions, Ltd. | Multiplexed nucleic acid analysis by fragmentation of double-stranded dna |
| ES2292116T3 (es) * | 2004-04-05 | 2008-03-01 | Basf Aktiengesellschaft | Particulas polimeras que contienen productos activos. |
| US7848889B2 (en) | 2004-08-02 | 2010-12-07 | Bioarray Solutions, Ltd. | Automated analysis of multiplexed probe-target interaction patterns: pattern matching and allele identification |
| EP1789796B1 (en) * | 2004-09-02 | 2011-05-11 | Abbott Point Of Care, Inc. | Blood urea nitrogen (bun) sensor |
| WO2006044577A1 (en) * | 2004-10-13 | 2006-04-27 | Ilypsa, Inc. | Pharmaceutical compositions comprising a toxin-binding oligosaccharide and a polymeric particle |
| US20060078534A1 (en) * | 2004-10-13 | 2006-04-13 | Dominique Charmot | Toxin binding compositions |
| US8486629B2 (en) | 2005-06-01 | 2013-07-16 | Bioarray Solutions, Ltd. | Creation of functionalized microparticle libraries by oligonucleotide ligation or elongation |
| JP5200425B2 (ja) * | 2006-06-23 | 2013-06-05 | 住友化学株式会社 | 農薬活性微生物製剤 |
| US9733242B2 (en) | 2012-10-07 | 2017-08-15 | Sevident, Inc. | Devices for capturing analyte |
| US9910040B2 (en) | 2012-07-09 | 2018-03-06 | Sevident, Inc. | Molecular nets comprising capture agents and linking agents |
| EP2712877B1 (en) * | 2012-09-28 | 2015-04-01 | Rohm and Haas Company | Curable formaldehyde free compositions as binders having solvent resistance |
| EP2972343A4 (en) * | 2013-03-14 | 2016-08-24 | Sevident Inc | MOLECULAR NETS ON SOLID PHASES |
| JP7091128B2 (ja) * | 2018-04-27 | 2022-06-27 | キヤノン株式会社 | 粒子、及びその製造方法 |
| GB201907468D0 (en) * | 2019-05-28 | 2019-07-10 | Univ Loughborough | Dispersion |
| CN114073789A (zh) * | 2020-08-18 | 2022-02-22 | 华中科技大学同济医学院附属协和医院 | 一种自动固化的无定形水凝胶压疮敷料及其制备方法 |
| CN113416267B (zh) * | 2021-07-28 | 2022-09-20 | 万华化学(四川)有限公司 | 一种改善工艺污水可生化性的abs接枝胶乳的凝聚方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2046898B2 (de) * | 1969-09-26 | 1977-09-22 | The Japanese Geon Co, Ltd, Tokio | Verfahren zur herstellung von propfmischpolymerisaten und deren verwendung in polyvinylchlorid enthaltenden formkoerpern |
| US3661994A (en) * | 1969-11-14 | 1972-05-09 | Stauffer Chemical Co | Graft polymers of rubber for reinforcing plastics |
| US3787522A (en) * | 1972-11-01 | 1974-01-22 | Ford Motor Co | Acrylate polymer particles comprising a core,an outer shell,and an intermediate layer |
| US3856883A (en) * | 1973-05-29 | 1974-12-24 | Ford Motor Co | Graded rubber particles having hydroxy functionality and a polymeric crosslinking agent |
| US4138383A (en) * | 1975-11-24 | 1979-02-06 | California Institute Of Technology | Preparation of small bio-compatible microspheres |
| US4107120A (en) * | 1976-06-17 | 1978-08-15 | Rohm And Haas Company | Heteropolymer acrylic latices and textiles treated therewith |
| US4210723A (en) * | 1976-07-23 | 1980-07-01 | The Dow Chemical Company | Method of coupling a protein to an epoxylated latex |
| US4140662A (en) * | 1977-03-25 | 1979-02-20 | Ortho Diagnostics, Inc. | Attachment of proteins to inert particles |
| CH628738A5 (de) * | 1977-08-03 | 1982-03-15 | Hoffmann La Roche | Immunologisches diagnose-reagenz. |
| FR2399448A1 (fr) * | 1977-08-03 | 1979-03-02 | Rhone Poulenc Ind | Latex de polymeres vinyliques stables aux electrolytes |
| CA1101330A (en) * | 1977-09-19 | 1981-05-19 | Ernst A. Fischer | Immunological material bonded to carboxylated latex polymer and process for making it |
| EP0001223A3 (en) * | 1977-09-19 | 1979-12-12 | F.Hoffmann-La Roche & Co. Aktiengesellschaft | Latex coated with a polyhydroxy compound, process for the preparation of this latex, immunological reagent containing this latex, process for the preparation of this reagent, application of this reagent, testing procedure utilising this reagent and reagent kit containing this reagent |
| GB2005275B (en) * | 1977-09-19 | 1982-03-10 | Hoffmann La Roche | Immunological reagent |
| GB2041940B (en) * | 1979-02-17 | 1982-12-22 | Dow Chemical Co | Method of coupling a protein to an epoxylated latex and the products formed therefrom |
| JPS55110118A (en) * | 1979-02-20 | 1980-08-25 | Dow Chemical Co | Method of combining epoxylated latex with protein and product formed therefrom |
| DE2907794A1 (de) * | 1979-02-28 | 1980-09-11 | Dow Chemical Co | Protein-latex-konjugat und verfahren zu seiner herstellung |
| JPS5655414A (en) * | 1979-10-11 | 1981-05-16 | Japan Synthetic Rubber Co Ltd | Polymer particle |
-
1981
- 1981-04-29 DE DE19813116995 patent/DE3116995A1/de active Granted
-
1982
- 1982-02-04 AT AT82100784T patent/ATE19524T1/de not_active IP Right Cessation
- 1982-02-04 EP EP82100784A patent/EP0065069B1/de not_active Expired
- 1982-03-30 DK DK144382A patent/DK163668C/da not_active IP Right Cessation
- 1982-04-28 JP JP57070541A patent/JPH0613611B2/ja not_active Expired - Lifetime
- 1982-04-29 MX MX192489A patent/MX160019A/es unknown
-
1986
- 1986-11-07 US US06/930,023 patent/US4710525A/en not_active Expired - Fee Related
-
1987
- 1987-07-20 US US07/075,416 patent/US4829101A/en not_active Expired - Lifetime
-
1990
- 1990-10-03 JP JP2263967A patent/JPH0723893B2/ja not_active Expired - Lifetime
-
1992
- 1992-05-19 JP JP4125759A patent/JP2536995B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4710525A (en) | 1987-12-01 |
| DK144382A (da) | 1982-10-30 |
| EP0065069A2 (de) | 1982-11-24 |
| JPH0613611B2 (ja) | 1994-02-23 |
| US4829101A (en) | 1989-05-09 |
| DK163668B (da) | 1992-03-23 |
| ATE19524T1 (de) | 1986-05-15 |
| DK163668C (da) | 1992-08-17 |
| EP0065069A3 (en) | 1983-04-27 |
| EP0065069B1 (de) | 1986-04-30 |
| JPH05346430A (ja) | 1993-12-27 |
| JPS585302A (ja) | 1983-01-12 |
| JP2536995B2 (ja) | 1996-09-25 |
| JPH03210476A (ja) | 1991-09-13 |
| JPH0723893B2 (ja) | 1995-03-15 |
| MX160019A (es) | 1989-11-07 |
| DE3116995A1 (de) | 1982-11-25 |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SIOL, WERNER, DR., 64297 DARMSTADT, DE |
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| 8339 | Ceased/non-payment of the annual fee |