JPH0482803A - Substrate for sustained releasing chemical in water - Google Patents
Substrate for sustained releasing chemical in waterInfo
- Publication number
- JPH0482803A JPH0482803A JP2159923A JP15992390A JPH0482803A JP H0482803 A JPH0482803 A JP H0482803A JP 2159923 A JP2159923 A JP 2159923A JP 15992390 A JP15992390 A JP 15992390A JP H0482803 A JPH0482803 A JP H0482803A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- water
- drug
- meth
- crosslinked polymer
- 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.)
- Pending
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000000758 substrate Substances 0.000 title claims abstract description 25
- 239000000126 substance Substances 0.000 title abstract description 6
- 230000002459 sustained effect Effects 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims abstract description 71
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000004711 α-olefin Substances 0.000 claims abstract description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- 238000013269 sustained drug release Methods 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 abstract description 56
- 125000001931 aliphatic group Chemical group 0.000 abstract description 5
- 230000000379 polymerizing effect Effects 0.000 abstract description 5
- 238000004132 cross linking Methods 0.000 abstract description 4
- 239000004615 ingredient Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 122
- 229940079593 drug Drugs 0.000 description 122
- 239000000203 mixture Substances 0.000 description 50
- 238000013268 sustained release Methods 0.000 description 39
- 239000012730 sustained-release form Substances 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 22
- -1 t- Butyl Chemical group 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 12
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000007654 immersion Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 8
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 8
- 239000005642 Oleic acid Substances 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000002265 prevention Effects 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000001954 sterilising effect 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
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- 241000195493 Cryptophyta Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000009333 weeding Methods 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FQKSRGCBHCFRTN-UHFFFAOYSA-N (4-nonylphenyl) prop-2-enoate Chemical compound CCCCCCCCCC1=CC=C(OC(=O)C=C)C=C1 FQKSRGCBHCFRTN-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical group CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- CKQAOGOZKZJUGA-UHFFFAOYSA-N 1-nonyl-4-(4-nonylphenoxy)benzene Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC1=CC=C(CCCCCCCCC)C=C1 CKQAOGOZKZJUGA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003254 anti-foaming effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical group CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-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
- IMCBLSMMFWHLSN-UHFFFAOYSA-N 2-methyl-n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C(C)=C IMCBLSMMFWHLSN-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XUZHQJYDYAASNF-UHFFFAOYSA-N ClCCl.C(COCCOCCOCCO)O Chemical compound ClCCl.C(COCCOCCOCCO)O XUZHQJYDYAASNF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- LSFBQOPXRBJSSI-UHFFFAOYSA-L calcium;tetradecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O LSFBQOPXRBJSSI-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229920001688 coating polymer Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- HEJZJSIRBLOWPD-VHXPQNKSSA-N didodecyl (z)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-VHXPQNKSSA-N 0.000 description 1
- DLBIZQBMDGOEFK-UHFFFAOYSA-N didodecyl 2-methylidenebutanedioate Chemical compound CCCCCCCCCCCCOC(=O)CC(=C)C(=O)OCCCCCCCCCCCC DLBIZQBMDGOEFK-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- MNMYRUHURLPFQW-UHFFFAOYSA-M silver;dodecanoate Chemical compound [Ag+].CCCCCCCCCCCC([O-])=O MNMYRUHURLPFQW-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/20—Controlling water pollution; Waste water treatment
- Y02A20/204—Keeping clear the surface of open water from oil spills
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、水中薬剤徐放用基材に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a substrate for sustained release of drugs in water.
さらに詳しくは、殺虫、殺菌、除草、防錆、浄化、消泡
、防藻、生物の生育促進、集魚などの効力を有する水中
溶出性薬剤を水中に一定速度で放出させることができ、
薬剤の効力を長時間にわたり持続させることができる水
中薬剤徐放用基材に関する。More specifically, it is possible to release a water-soluble agent into water at a constant rate, which has effects such as insecticidal, sterilizing, weeding, rust prevention, purification, antifoaming, algae prevention, promotion of biological growth, and fish collection.
The present invention relates to a substrate for sustained release of drugs in water that can maintain the efficacy of drugs for a long period of time.
（従来の技術）
従来より、農林水産、水処理等の水に関わる分野におい
て殺虫、殺菌、除草、防錆、浄化、消泡、防藻、生物の
生育促進、集魚などの目的で、各種水中溶出性薬剤が用
いられている。これらの薬剤は、従来そのままあるいは
溶液や分散液とし、被処理水系に投入もしくは散布する
ことにより使用されてきた。しかし、この方法は、一過
性の効果しかなく、また余分な薬剤が被処理水系から流
出するため経済的でなく環境や人体などに悪影響を及ぼ
すという問題があった。そこで近年、薬剤を徐放させる
技術への要求が高まっている。(Conventional technology) Traditionally, in water-related fields such as agriculture, forestry and fisheries, and water treatment, various underwater treatments have been used for purposes such as insecticide, sterilization, weeding, rust prevention, purification, defoaming, algae prevention, promotion of biological growth, and fish collection. Eluting drugs are used. Conventionally, these chemicals have been used as they are, or in the form of solutions or dispersions, by being added or sprayed into the water system to be treated. However, this method has only a temporary effect, and since excess chemicals flow out of the water system to be treated, there are problems in that it is not economical and has a negative impact on the environment and the human body. Therefore, in recent years, there has been an increasing demand for technology that allows sustained release of drugs.
このような薬剤の徐放技術として薬剤を基材に担持もし
くは吸収させ水中に徐放させる方法がいくつか報告され
ており、（１）薬剤を無機物や高分子化合物等の基材中
に含有せしめた固形物を水系に投入もしくは散布し徐放
させる方法、（２）非架橋皮膜形成性高分子化合物を基
材とし該基材に薬剤を混合して得たコーテイング材を構
造物に塗布し、これを水系に浸漬し薬剤を徐放させる方
法等が提案されている。As a sustained release technology for such drugs, several methods have been reported in which the drug is supported or absorbed on a base material and then released in water. (2) applying a coating material made of a non-crosslinked film-forming polymer compound as a base material and mixing a drug into the base material to a structure; A method has been proposed in which the drug is immersed in an aqueous system to gradually release the drug.
（１）の方法としては、たとえば粘土や鉱物質を基材と
し薬剤を含有させる方法、セメントや焼き石膏等を基材
とし薬剤を含浸させる方法（特開昭５３−１３８８８５
）、水性ゲル状物中に薬剤を含有さぜる方法（特開昭５
７−１６３３０２）などがあけられる。しかしこれらの
方法は、水中で、固形物の型くずれや溶解を生じたり、
薬剤を保持する能力が低くしかも水温や水流の影響を受
は易いため、薬剤に対する放出速度のコントロール性が
不十分であり、薬剤の効果を長時間持続させることか難
しいなどの欠点を有していた。Method (1) includes, for example, a method in which a clay or mineral material is used as a base material and contains a drug, and a method in which a base material such as cement or calcined gypsum is impregnated with a drug (Japanese Patent Laid-Open No. 53-138885).
), a method of mixing a drug in an aqueous gel (Unexamined Japanese Patent Publication No. 5
7-163302) etc. can be opened. However, these methods may cause the solids to lose their shape or dissolve in water, or
Because they have a low ability to retain drugs and are easily affected by water temperature and water flow, they have drawbacks such as insufficient control over the drug release rate and difficulty in maintaining the drug's effect for a long time. Ta.
（２）の方法としては、（メタ）アクリル酸エステルの
非架橋共重合体をコーティング用高分子化合物として用
いる方法（特開昭５１−７０３４、特開昭５８−１２０
６７８、特公平１−５４３８８）などがあげられる。し
かし、この方法で用いられる高分子化合物は、皮膜形成
能は有しているものの薬剤を保持する能力か低いなめに
、皮膜形成能を保持しながら多量の薬剤成分を含有する
コーテイング材を調製することか難しく、また薬剤に対
する放出速度のコン１〜ロール性も不十分となり長期に
わたって薬剤の効果を持続させることができないなどの
欠点を有していた。Method (2) is a method using a non-crosslinked copolymer of (meth)acrylic acid ester as a coating polymer compound (JP-A-51-7034, JP-A-58-120).
678, Special Publication No. 1-54388), etc. However, although the polymer compound used in this method has film-forming ability, it has a low ability to retain drugs, so it is necessary to prepare a coating material that contains a large amount of drug components while retaining film-forming ability. Moreover, the release rate of the drug is insufficiently controlled, making it impossible to maintain the effect of the drug over a long period of time.
（発明が解決しようとする課題）
本発明は、従来の水中薬剤徐放用基材が有する上記問題
点を解決するものである。(Problems to be Solved by the Invention) The present invention solves the above-mentioned problems of conventional substrates for sustained release of drugs in water.
すなわち、本発明の目的は、殺虫、殺菌、除草、防錆、
浄化、消泡、防藻、生物の生育促進、集魚などの効力を
有する薬剤を水中に一定速度で溶出させることがてき、
薬剤の効力を長時間にわたり持続させることかできる水
中薬剤徐放用基材を提供することにある。That is, the purpose of the present invention is to kill insects, sterilize, weed, prevent rust,
It is possible to elute chemicals with effects such as purification, defoaming, algae prevention, promotion of biological growth, and attracting fish into water at a constant rate.
An object of the present invention is to provide a substrate for sustained release of drugs in water that can maintain the efficacy of drugs for a long period of time.
（課題を解決するための手段および作用）本発明者らは
、特定の単量体を重合して得た架橋重合体が、殺虫、殺
菌、除草、防錆、浄化、消泡、防藻、生物の生育促進、
集魚などの効力を有する水中溶出性薬剤成分を多量に吸
収し、この架橋重合体に薬剤成分を吸収させて得られた
薬剤組成物か水中における薬剤成分の溶出コントロール
性に優れ上記効力を長時間にわたり持続できることを見
いたし、本発明を完成するに至った。(Means and effects for solving the problem) The present inventors have discovered that the crosslinked polymer obtained by polymerizing specific monomers has the following properties: insecticidal, sterilizing, weeding, rust prevention, purification, antifoaming, antialgae Promotion of biological growth,
A drug composition obtained by absorbing a large amount of a water-soluble drug component that has the effect of attracting fish, etc., and allowing the drug component to be absorbed into this crosslinked polymer has excellent controllability of elution of the drug component in water and maintains the above-mentioned efficacy for a long time. We have found that the present invention can be sustained over a long period of time, and have completed the present invention.
すなわち、本発明は、溶解度パラメーター（ＳＰ値）か
９以下の単量体を主成分としてなる分子中に１個の重合
性不飽和基を有する単量体（Ａ）８０〜９９．９９９重
量％および分子中に少なくとも２個の重合性不飽和基を
有する架矯性単量体（Ｂ）０．００１〜２０重量％（た
だし単量体（Ａ）および（Ｂ）の合計は１００重量％で
ある）からなる単量体成分を重合して得られる架橋重合
体（Ｔ）からなる水中薬剤徐放用基材に関する。That is, the present invention uses 80 to 99.999% by weight of a monomer (A) having one polymerizable unsaturated group in the molecule, which is mainly composed of a monomer with a solubility parameter (SP value) of 9 or less. and 0.001 to 20% by weight of a crosslinking monomer (B) having at least two polymerizable unsaturated groups in the molecule (however, the total of monomers (A) and (B) is 100% by weight) The present invention relates to a substrate for sustained release of drugs in water, which is made of a crosslinked polymer (T) obtained by polymerizing a monomer component consisting of (a).
溶解度パラメーター（ＳＰ値）は、化合物の極性を表す
尺度として一般に用いられており、本発明ではＳｍａｌ
ｌの計算式にＨｏｙの凝集エネルギ一定数を代入して導
いた値を適用するものとし、単位は（ｃａｌ／■’ ）
１／２で表わされる。The solubility parameter (SP value) is generally used as a measure of the polarity of a compound, and in the present invention, the solubility parameter (SP value) is
The value derived by substituting Hoy's cohesive energy constant into the formula for l is applied, and the unit is (cal/■')
It is expressed as 1/2.
本発明で用いられる単量体（Ａ）の主成分を構成する単
量体は、溶解度パラメーター（ＳＰ値）が９以下で分子
中に１個の重合性不飽和基を有する単量体である。溶解
度パラメーター（ＳＰ値）が９を超える単量体を単量体
（Ａ）の主成分に用いると、得られる架橋重合体が吸収
できる水中溶出性薬剤の量が著しく低下したり、あるい
は薬剤の溶出コン１−ロール性が著しく劣った架橋重合
体しか得られなくなるため好ましくない。The monomer constituting the main component of the monomer (A) used in the present invention is a monomer having a solubility parameter (SP value) of 9 or less and one polymerizable unsaturated group in the molecule. . If a monomer with a solubility parameter (SP value) exceeding 9 is used as the main component of monomer (A), the amount of water-soluble drug that can be absorbed by the resulting crosslinked polymer may be significantly reduced, or the drug may be This is not preferable because only a crosslinked polymer with extremely poor elution control properties can be obtained.
溶解度パラメーター（ＳＰ値）が９以下で分子中に１個
の重合性不飽和基を有する単量体としては、たとえばメ
チル（メタ）アクリレート、エチル（メタ）アクリレー
ト、ブチル（メタ）アクリレート、ｔ−ブチル（メタ）
アクリレート、２エチルヘキシル（メタ）アクリレート
、ｎ−オクチル（メタ）アクリレート、ドデシル（メタ
）アクリレート、ステアリル（メタ）アクリレート、フ
ェニル（メタ）アクリレート、オクチルフェニル（メタ
）アクリレート、ノニルフェニル（メタ）アクリレート
、ジノニルフェニル（メタ）アクリレート、シクロヘキ
シル（メタ）アクリレート、メンチル（メタ）アクリレ
ート、ジブチルマレエート、ジドデシルマレエート、ド
デシルクロトネート、ジドデシルイタコネートなどの不
飽和カルボン酸エステル：（ジ）ブチル（メタ）アクリ
ルアミド、（ジ）ドデシル（メタ）アクリルアミド、（
ジ）ステアリル（メタ）アクリルアミド、（ジ）ブチル
フェニル（メタ）アクリルアミド、（ジ）オクチルフェ
ニル（メタ）アクリルアミドなどの炭化水素基を有する
（メタ）アクリルアミド；１ヘキセン、１−オクテン、
イソオクテン、１ノネン、１−デセン、■−ドデセンな
どのα−オレフィン；ビニルシクロヘキサンなどの脂環
式ビニル化合物ニドデシルアリルエーテルなどの脂肪族
炭化水素基を有するアリルエーテル；カプロン酸ビニル
、ラウリン酸ビニル、パルミチン酸ビニル、ステアリン
酸ビニルなどの脂肪族炭化水素基を有するビニルエステ
ル：ブチルビニルエーテル、ドデシルビニルエーテルな
どの脂肪族炭化水素基を有するビニルエーテル：スチレ
ン、ｔ−ブチルスチレン、オクチルスチレンなどの芳香
族ビニル化合物などをあげることかでき、これらの単量
体を１種または２種以上用いることかできる。Examples of monomers having a solubility parameter (SP value) of 9 or less and having one polymerizable unsaturated group in the molecule include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and t- Butyl (meth)
Acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate, phenyl (meth)acrylate, octylphenyl (meth)acrylate, nonylphenyl (meth)acrylate, Unsaturated carboxylic acid esters such as nonylphenyl (meth)acrylate, cyclohexyl (meth)acrylate, menthyl (meth)acrylate, dibutyl maleate, didodecyl maleate, dodecyl crotonate, didodecyl itaconate: (di)butyl (meth)acrylate, etc. ) Acrylamide, (di)dodecyl (meth)acrylamide, (
(meth)acrylamide having a hydrocarbon group such as di)stearyl(meth)acrylamide, (di)butylphenyl(meth)acrylamide, (di)octylphenyl(meth)acrylamide; 1-hexene, 1-octene,
α-olefins such as isooctene, 1-nonene, 1-decene, ■-dodecene; alicyclic vinyl compounds such as vinylcyclohexane; allyl ethers with aliphatic hydrocarbon groups such as nidodecyl allyl ether; vinyl caproate, vinyl laurate Vinyl esters with aliphatic hydrocarbon groups such as , vinyl palmitate, and vinyl stearate; Vinyl ethers with aliphatic hydrocarbon groups such as butyl vinyl ether and dodecyl vinyl ether; Aromatic vinyls such as styrene, t-butylstyrene, and octylstyrene. Compounds, etc. can be mentioned, and one type or two or more types of these monomers can be used.
これらの中でも、前記した性能に一層優れた水中薬剤徐
放用基材として有効な架橋重合体を与える単量体として
は、少なくとも１個の炭素数３〜３０の脂肪族炭化水素
基を有し、かつアルキル（メタ）アクリレート、アルキ
ルアリール（メタ）アクリレート、アルキル〈メタ）ア
クリルアミド、アルキルアリール（メタ）アクリルアミ
ド、アルキルスチレンおよびα−オレフィンからなる群
より選ばれる少なくとも１種の不飽和化合物（ａ）を主
成分としてなる単量体（Ａ）が特に好ましい。Among these, monomers having at least one aliphatic hydrocarbon group having 3 to 30 carbon atoms are preferred as monomers that provide crosslinked polymers that are effective as substrates for sustained release of drugs in water and have the above-mentioned properties. , and at least one unsaturated compound (a) selected from the group consisting of alkyl (meth)acrylate, alkylaryl (meth)acrylate, alkyl<meth)acrylamide, alkylaryl (meth)acrylamide, alkylstyrene, and α-olefin. Especially preferred is the monomer (A) containing as a main component.
このような溶解度パラメーター（ＳＰ値）か９以下の単
量体の単量体（Ａ）中における使用量は、単量体（Ａ）
の全体量に対して５０重量％以上、より好ましくは７０
重量％以上となる割合である。The amount of such a monomer with a solubility parameter (SP value) of 9 or less in monomer (A) is
50% by weight or more, more preferably 70% by weight based on the total amount of
This is a ratio of % by weight or more.
該溶解度パラメーター（ＳＰ値）か９以下の単量体の単
量体（Ａ）の中の使用量が５０重量％未満では、得られ
る架橋重合体が吸収できる水中溶出性薬剤の量が著しく
低下したり、溶出コントロール性の低い架橋重合体しか
得られない。If the amount of monomer (A) with a solubility parameter (SP value) of 9 or less is less than 50% by weight, the amount of water-soluble drug that can be absorbed by the resulting crosslinked polymer is significantly reduced. Otherwise, only crosslinked polymers with poor elution controllability can be obtained.
したかって、本発明では、単量体（Ａ）中に溶解度パラ
メーター（ＳＰ値）が９以下の単量体が５０重量％以上
含有される必要があるが、単量体（Ａ）中に５０重量％
以下の割合で溶解度パラメーター（ＳＰ値）か９を越え
る単量体か含有されてもよい。このような単量体として
は、たとえば（メタ）アクリル酸、アクリロニトリル、
無水７レイン酸、フタル酸、ヒドロキシエチル（メタ）
アクリレート、ポリエチレングリコール（メタ）アクリ
レート、メトキシポリエチレンクリコール（メタ）アク
リレートなどをあけることができる。Therefore, in the present invention, it is necessary that the monomer (A) contains 50% by weight or more of a monomer having a solubility parameter (SP value) of 9 or less. weight%
Monomers with a solubility parameter (SP value) exceeding 9 may be contained in the following proportions. Examples of such monomers include (meth)acrylic acid, acrylonitrile,
7 Leicic anhydride, phthalic acid, hydroxyethyl (meth)
Acrylate, polyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, etc. can be used.
本発明で用いられる架橋性単量体（Ｂ）としては、たと
えばエチレングリコールジ（メタ）アクリレート、ジエ
チレングリコールジ（メタ）アクリレート、ポリエチレ
ングリコール（メタ）ジアクリレート、ポリエチレング
リコールーポリプロピレングリコールジ（メタ）アクリ
レ−１〜、プロピレングリコールジ（メタ）アクリレー
ト、ポリエチレングリコールジ（メタ）アクリレート、
１．３−ブチレングリコールジ（メタ）アクリレート、
ネオペンチルグリコールジ（メタ）アクリレ−１へ、１
．６−ヘキサンシオールジ（メタ）アクリレート、Ｎ、
Ｎ−スチレンビスアクリルアミド、Ｎ、Ｎ−プロピレン
ビスアクリルアミド、グリセリントリ（メタ）アクリレ
ート、トリメチロールプロパントリ（メタ）アクリレー
ト、テトラメチロールメタンテトラ（メタ）アクリレ−
１〜、多価アルコール（たとえばグリセリン、トリメチ
ロールプロパンあるいはテトラメチロールメタン）のア
ルキレンオキシド付加物と（メタ）アクリル酸とのエス
テル化によって得られる多官能（メタ）アクリレートや
ジビニルベンゼンなどをあげることができ、これらの架
橋性単量体を１種または２種以上用いることかできる。Examples of the crosslinkable monomer (B) used in the present invention include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol (meth)diacrylate, and polyethylene glycol-polypropylene glycol di(meth)acrylate. -1~, propylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate,
1.3-butylene glycol di(meth)acrylate,
To neopentyl glycol di(meth)acrylate-1, 1
．． 6-hexanethiol di(meth)acrylate, N,
N-styrene bisacrylamide, N,N-propylene bisacrylamide, glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate
1 to polyfunctional (meth)acrylates and divinylbenzene obtained by esterifying an alkylene oxide adduct of a polyhydric alcohol (for example, glycerin, trimethylolpropane or tetramethylolmethane) with (meth)acrylic acid. One type or two or more types of these crosslinkable monomers can be used.
架橋重合体（Ｉ）を製造する際に用いられる単量体成分
中の単量体（Ａ）および架橋性単量体（Ｂ）の比率は、
単量体（Ａ）および架橋性単量体（Ｂ）の合計に対して
、単量体（Ａ）が８０〜９９．９９９重量％の範囲、架
橋性単量体（Ｂ）が０．００１〜２０重量％の範囲であ
る。The ratio of monomer (A) and crosslinkable monomer (B) in the monomer components used when producing crosslinked polymer (I) is:
Monomer (A) is in the range of 80 to 99.999% by weight with respect to the total of monomer (A) and crosslinkable monomer (B), and crosslinkable monomer (B) is 0.001% by weight. -20% by weight.
単量体（Ａ）が８０重量％未満であったり架橋性単量体
（Ｂ）が２０重量％を越えると、得られる架橋重合体の
架橋密度か高くなりすぎて架橋重合体が吸収できる水中
溶出性薬剤の量か著しく低下するなめ好ましくない。ま
た、単量体（Ａ）が９９．９９９重量％を越えると、得
られる重合体の薬剤への可溶性が増大して、溶出コント
ロール性の低い架橋重合体しか得られない。If the monomer (A) is less than 80% by weight or the crosslinkable monomer (B) is more than 20% by weight, the crosslinking density of the resulting crosslinked polymer will be too high and the crosslinked polymer will not be able to absorb water. This is undesirable because the amount of eluted drug is significantly reduced. Furthermore, if the monomer (A) exceeds 99.999% by weight, the solubility of the resulting polymer in drugs increases, resulting in only a crosslinked polymer with poor elution controllability.
架橋重合体（Ｉ）を製造するには、重合開始剤を用いて
前記単量体成分を共重合させればよい。In order to produce the crosslinked polymer (I), the monomer components may be copolymerized using a polymerization initiator.
共重合は、溶媒中での重合、エマルジョン重合、懸濁重
合あるいは塊状重合などの公知の方法により行うことが
できる。Copolymerization can be carried out by known methods such as polymerization in a solvent, emulsion polymerization, suspension polymerization, or bulk polymerization.
溶液重合は、エチルアルコール、イソプロピルアルコー
ルなどのアルコール類、ベンゼン、トルエン、キシレン
、シクロヘキサン、ｎ−ヘキサンなどの芳香族あるいは
脂肪族炭化水素類、メチルエチルゲトンなどのケトン類
、酢酸エチルなどのエステル類などの溶媒中、たとえば
ベンゾイルパーオキシド、ラウロイルパーオキシド、ク
メンハイドロパーオキシドなどの有機過酸化物や、２２
′−アゾビスイソブチロニトリル、２．２′アゾビスジ
メチルバレロニトリルなどのアゾ化合物などの油溶性重
合開始剤の存在下に行うことができる。重合温度は通常
０〜１５０°Ｃの範囲であり、重合装置は撹拌槽を用い
てもよく、ニーターを用いてもよい。このように溶液重
合すると、目的とする架橋重合体（Ｉ）を含有しな粘稠
液状物あるいはゲル状物を得ることができる。Solution polymerization is performed using alcohols such as ethyl alcohol and isopropyl alcohol, aromatic or aliphatic hydrocarbons such as benzene, toluene, xylene, cyclohexane, and n-hexane, ketones such as methyl ethyl getone, and esters such as ethyl acetate. organic peroxides such as benzoyl peroxide, lauroyl peroxide, cumene hydroperoxide, 22
It can be carried out in the presence of an oil-soluble polymerization initiator such as an azo compound such as '-azobisisobutyronitrile or 2.2'azobisdimethylvaleronitrile. The polymerization temperature is usually in the range of 0 to 150°C, and the polymerization apparatus may be a stirring tank or a kneader. By carrying out solution polymerization in this manner, a viscous liquid or gel-like material that does not contain the desired crosslinked polymer (I) can be obtained.
エマルジョン重合は、高ＨＬＢ値を有する乳化剤を用い
、過［酸アンモニウム、過硫酸カリウムなどの水溶性重
合開始剤やこれらと亜硫酸水素ナトリウム等の還元剤を
併用したレドックス系重合開始剤および単量体成分を水
中に供給乳化して０〜１００℃の温度範囲で重合させる
ことにより、０．０１〜１０μｍ程度の微粒状の架橋重
合体（Ｉ）を含有する水性エマルジョン液を得ることが
できる。Emulsion polymerization uses an emulsifier with a high HLB value, a water-soluble polymerization initiator such as ammonium persulfate, potassium persulfate, a redox polymerization initiator and a monomer in combination with these and a reducing agent such as sodium bisulfite. By supplying the components in water, emulsifying them, and polymerizing them at a temperature range of 0 to 100°C, an aqueous emulsion liquid containing crosslinked polymer (I) in the form of fine particles of about 0.01 to 10 μm can be obtained.
懸濁重合は、たとえば、高ＨＬ Ｂ値を有する乳化剤や
、ポリビニルアルコール、ヒドロキシエチルセルロース
、ゼラチンなどの保護コロイド剤を使用し、単量体成分
を水中に懸濁させ、油溶性重合開始剤の存在下で重合す
れはよい。重合温度は０〜１５０℃の範囲が好ましい。Suspension polymerization involves, for example, using an emulsifier with a high HL B value or a protective colloid agent such as polyvinyl alcohol, hydroxyethyl cellulose, gelatin, etc., suspending the monomer components in water, and reducing the presence of an oil-soluble polymerization initiator. Polymerization at the bottom is good. The polymerization temperature is preferably in the range of 0 to 150°C.
得られた１〜１０００μｍ程度の微粒状樹脂の水性懸濁
液をろ過乾燥することにより粒状の架橋重合体（Ｉ＞が
得られる。A granular crosslinked polymer (I>) is obtained by filtering and drying the resulting aqueous suspension of fine resin particles with a diameter of about 1 to 1000 μm.
塊状重合では、たとえば単量体成分を重合開始剤の存在
下で型に流し込み、０〜１５０℃の条件下にて重合を行
うことにより、重合器の形状に成型された架橋重合体（
Ｉ）が得られる。In bulk polymerization, for example, monomer components are poured into a mold in the presence of a polymerization initiator and polymerized under conditions of 0 to 150°C to form a crosslinked polymer (
I) is obtained.
本発明の水中薬剤徐放用基材として有効な架橋重合体（
Ｉ）は、水中溶出性薬剤と混合することにより水中徐放
性薬剤組成物として用いることかできる。水中溶出性薬
剤としては、油溶性であり且つ水中にｉｐｐｍ以上の溶
解度を有し、殺虫、殺菌、除草、防錆、浄化、消泡、防
藻、生物の生育促進、集魚などの効力を有する成分であ
れはよく、目的に応じて選択できる。たとえば、オクタ
ツール、トリデカノールなどのアルコール類：力プロン
酸、オレイン酸、ラウリン酸銀、ミリスチン酸カルシウ
ム、ナンテン酸（塩）などのカルボン酸く塩）類ニドデ
シルメルカプタンなどのチオール類ニブチルアミン、ト
リブチルアミン２、ジフェニルアミン（塩）、ラウリル
アミン（塩）などのアミン（塩）類；ナタネ油、大豆油
、ヒマシ油、鯨油、牛脂などの動植物油類；塩化ベンセ
トニウム、アルキルピリジニウム塩など４級アンモニウ
ム塩類：アルキルフェノール、トリクロロフェノール、
オイゲノールなどのフェノール類；フタル酸ジブチル、
フタル酸ジオクチル、オキシ安息香酸エチルなどのエス
テル類：３−クロロ−２メチルーグロペン、ジクロロベ
ンゼンなどの有機塩素化合物類；塩化トリフェニルスズ
などの有機スズ化合物類ニジアルキルスルフィドなどの
千オニーチル頚：ヒスチジン、グルタミンなどのアミノ
酸類；ケロシン、ベンゼン、トルエン、キシレンなどの
炭化水素類；２−イソプロピルフェニル−Ｎ−メチルカ
ーバメートなどのカーバメート類；４−メチルチオフエ
ニルジプロピルホスフェートなどのホスフェート類：エ
ムペンスリン、アレスリンなどのピレスロイド類：アデ
ニン、アテノシンなどの核酸類；レシチンなどのリン脂
質などをあげることができ、これら中から１種または２
種以上を用いることができる。Cross-linked polymer (
I) can be used as a sustained-release drug composition in water by mixing with a water-soluble drug. As a water-soluble drug, it is oil-soluble and has a solubility in water of IPPM or higher, and has effects such as insecticidal, sterilizing, weeding, rust prevention, purification, defoaming, algae prevention, promoting the growth of living things, and attracting fish. The ingredients can be selected depending on the purpose. For example, alcohols such as octatool and tridecanol; carboxylic acid salts such as hydroproic acid, oleic acid, silver laurate, calcium myristate, and nantenic acid (salts); thiols such as nidodecyl mercaptan; nibutylamine, Amines (salts) such as butylamine 2, diphenylamine (salt), and laurylamine (salt); Animal and vegetable oils such as rapeseed oil, soybean oil, castor oil, whale oil, and beef tallow; Quaternary ammonium salts such as bencethonium chloride and alkylpyridinium salts : Alkylphenol, trichlorophenol,
Phenols such as eugenol; dibutyl phthalate,
Esters such as dioctyl phthalate and ethyl oxybenzoate; Organic chlorine compounds such as 3-chloro-2-methyl-glopene and dichlorobenzene; Organic tin compounds such as triphenyltin chloride; Amino acids such as glutamine; Hydrocarbons such as kerosene, benzene, toluene, and xylene; Carbamates such as 2-isopropylphenyl-N-methyl carbamate; Phosphates such as 4-methylthiophenyl dipropyl phosphate; Empensuline, Allethrin, etc. Pyrethroids: Nucleic acids such as adenine and atenosine; phospholipids such as lecithin; one or two of these
More than one species can be used.
架橋重合体（Ｉ）からなる本発明の水中薬剤徐放用基材
と水中溶出性薬剤とを混合して水中徐放性薬剤組成物と
する際の混合割合は、特に制限はないが、架橋重合体（
Ｉ）か組成物中２〜８０重量％の範囲、水中溶出性薬剤
が２０〜９８重量％の範囲であることが好ましい。架橋
重合体（Ｉ）の使用量か２重量％未満であれは、水中溶
出性薬剤を完全に吸収しきれず遊離した水中溶出性薬剤
が残存するため好ましくない。また、架橋重合体（■）
を８０重量％を越えて使用すると、水中溶出性薬剤の溶
出量か少なく十分な薬剤の効力か得られなくなるため好
ましくない。なお、組成物中には、基材および薬剤以外
に、薬剤としての効力を有しないが薬剤の取扱いを容易
にしたり薬剤放出速度をコントロールするための有機溶
剤等の各種添加物を含有させてもよい。There is no particular restriction on the mixing ratio when mixing the substrate for underwater drug sustained release of the present invention comprising crosslinked polymer (I) and a water-soluble drug to form an underwater sustained release drug composition. Polymer (
I) is preferably in the range of 2 to 80% by weight of the composition, and the water-soluble drug is preferably in the range of 20 to 98% by weight. If the amount of crosslinked polymer (I) used is less than 2% by weight, it is not preferable because the water-soluble drug will not be completely absorbed and the free water-soluble drug will remain. In addition, crosslinked polymer (■)
If more than 80% by weight is used, the elution amount of the water-soluble drug will be too small and sufficient drug efficacy will not be obtained, which is not preferable. In addition to the base material and the drug, the composition may contain various additives such as organic solvents that do not have any medicinal effect but are used to facilitate the handling of the drug or to control the drug release rate. good.
本発明の水中薬剤徐放用基材と水中溶出性薬剤を混合し
て水中徐放性薬剤組成物を得る方法としては、たとえは
架橋重合体（Ｉ）を含有する液状物と水中溶出性薬剤と
を混合した後に溶媒を除去する方法や、水中溶出性薬剤
洛中に粒状あるいは成型された架橋重合体（Ｉ）を浸漬
して一定時間水中溶出性薬剤を架ｇ重合体（Ｉ＞に吸収
させた後に薬剤浴から引き上げて水中徐放性薬剤組成物
とする方法、あるいは架橋重合体（Ｉ）を生成する単量
体成分と水中溶出性薬剤成分とを混合して得た単量体溶
液を用い重合させて水中徐放性薬剤組成物を得る方法な
どを採用することができる。As a method for obtaining a sustained-release drug composition in water by mixing the substrate for sustained release of drugs in water of the present invention and a water-soluble drug, for example, a liquid material containing crosslinked polymer (I) and a water-soluble drug may be mixed. There is a method of removing the solvent after mixing with the water-soluble drug, or a method of immersing the granular or molded cross-linked polymer (I) in the water-soluble drug and allowing the water-soluble drug to be absorbed by the cross-linked polymer (I) for a certain period of time. or a monomer solution obtained by mixing a monomer component that forms the crosslinked polymer (I) and a water-soluble drug component. A method of obtaining a sustained-release drug composition in water by polymerizing the drug can be employed.
また、水中溶出性薬剤を架橋重合体（１）に吸収させる
場合、水中溶出性薬剤が揮散・変質しない範囲で加熱し
たり、水中溶出性薬剤を溶剤に溶解あるいは分散させた
溶液を用いたりして、薬剤の吸収速度を速めることもで
きる。In addition, when a water-soluble drug is absorbed into the crosslinked polymer (1), the water-soluble drug may be heated within a range that does not volatilize or change its quality, or a solution in which the water-soluble drug is dissolved or dispersed in a solvent may be used. It can also speed up the absorption rate of the drug.
本発明の水中薬剤徐放用基材と水中溶出性薬剤を混合し
た組成物を使用する方法としては、目的や使用する場所
などに応じ種々の方法を採用することができる。たとえ
ば架橋重合体（Ｉ）および水中溶出性薬剤からなる組成
物を溶媒に分散させた液状物を、壁面、板、コンクリー
ト、網などの構造物面に塗布した後、溶媒を除去して得
な薬剤組成物の被覆された構造物を水中に浸漬して使用
する方法や、水中溶出性薬剤を架橋重合体（Ｉ＞に吸収
させて得られた薬剤組成物を布や網などで包み込み水中
に浸漬して使用する方法、あるいは薬剤組成物を円筒管
などに充填し、水を該充填管を通して流すことにより使
用する方法などがあけられる。Various methods can be employed to use the composition of the present invention, which is a mixture of the substrate for sustained release of drugs in water and a water-soluble drug, depending on the purpose and place of use. For example, a liquid product in which a composition consisting of crosslinked polymer (I) and a water-soluble drug is dispersed in a solvent is applied to the surface of a structure such as a wall, board, concrete, or net, and then the solvent is removed. There is a method in which a structure coated with a drug composition is immersed in water, and a drug composition obtained by absorbing a water-soluble drug in a crosslinked polymer (I>) is wrapped in cloth or a net and then immersed in water. Possible methods include immersion, or filling a cylindrical tube with the drug composition and flowing water through the filled tube.
さらに、本発明の水中薬剤徐放用基材と水中溶出性薬剤
を混合した組成物には必要に応じて酸化防止剤、色素、
香料その他の添加物を加えてもよい。Furthermore, the composition in which the underwater drug sustained release substrate of the present invention is mixed with the water-soluble drug may optionally contain antioxidants, pigments, etc.
Flavoring agents and other additives may also be added.
〈発明の効果）
本発明の特定の架橋重合体からなる水中薬剤徐放用基材
は、水中溶出性薬剤を高い相互作用により基材中に吸収
して保持することができるため、多量の水中溶出性薬剤
を含有した安定な組成物を形成する。しなかって、本発
明の基材は、−旦吸収して保持した水中溶出性薬剤を有
効な量で水中に一定速度で放出し、高い徐放コン１〜ロ
ール性を発揮するため、長時間にわたり薬剤の効力を持
続することができる。<Effects of the Invention> The substrate for sustained release of drugs in water made of the specific crosslinked polymer of the present invention can absorb and retain water-soluble drugs in the substrate through high interaction. Forming a stable composition containing the elutable drug. However, the base material of the present invention releases an effective amount of the water-soluble drug that has been absorbed and retained into water at a constant rate, and exhibits high sustained release properties, so it can be used for a long time. The efficacy of the drug can be maintained for a long time.
また、使用目的に応じて種々の形態で使用できるなめ、
水に関わる広範な用途に適用でき、しかも経済的である
ばかりでなく環境汚染や人体への悪影響などの弊害か極
めて少ない。In addition, there are various types of licks that can be used in various forms depending on the purpose of use.
It can be applied to a wide range of water-related applications, is not only economical, but also has very few negative effects such as environmental pollution and adverse effects on the human body.
（実施例）
次に、本発明の水中薬剤徐放用基材について、実施例お
よび比較例をあげて詳細に説明するが、本発明はこれだ
けに限定されるものではない。なお、例中詩に断わりの
ない限り部は重量部を表わすものとする。(Example) Next, the substrate for underwater drug sustained release of the present invention will be described in detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. In addition, unless otherwise specified in the poem, parts refer to parts by weight.
実施例１
温度計、撹拌機、オス導入管および還流冷却器を備えた
５ ００ ｍｌフラスコに、ゼラチン３部を水３００部
に溶解して仕込み、撹拌下フラスコ内を窒素置換し、窒
素気流下に４０℃に加熱しな。その後、単量体（Ａ）と
してノニルフェニルアクリレート（ＳＰ値： ８．３）
９９．７９４部、架橋性単量体（Ｂ）として１，６−ヘ
キサンジオールジアクリレート０．２０６部および重合
開始剤としてベンゾイルパーオキシド０．５部からなる
溶液をフラスコ内に一度に加え、４００ｒｐ１１１の条
件１つ
下で激しく撹拌した。Example 1 A 500 ml flask equipped with a thermometer, a stirrer, a male inlet tube, and a reflux condenser was charged with 3 parts of gelatin dissolved in 300 parts of water, and while stirring, the inside of the flask was replaced with nitrogen, and the flask was heated under a nitrogen stream. Heat to 40℃. Then, nonylphenyl acrylate (SP value: 8.3) was used as the monomer (A).
A solution consisting of 99.794 parts, 0.206 parts of 1,6-hexanediol diacrylate as the crosslinkable monomer (B), and 0.5 parts of benzoyl peroxide as a polymerization initiator was added all at once into the flask, and the mixture was heated at 400 rp111. The mixture was stirred vigorously under one condition.
ついで、フラスコ内の温度を８０℃に昇温し、同温度で
２時間維持して重合反応を行い、その後さらにフラスコ
内を９０°Ｃに昇温し、２時間維持して重合を完了させ
た。重合完了後、粒状の生成物をろ別し、水で洗浄した
後６０’Ｃで乾燥させることにより、粒径１００〜１０
００部ｍの架橋重合体（１）を得な。Next, the temperature inside the flask was raised to 80°C and maintained at the same temperature for 2 hours to perform a polymerization reaction, and then the temperature inside the flask was further raised to 90°C and maintained for 2 hours to complete polymerization. . After the polymerization is completed, the granular product is filtered, washed with water, and dried at 60'C to reduce the particle size to 100-10.
Obtain 00 parts m of crosslinked polymer (1).
得られた架橋重合体（１）からなる本発明の水中薬剤徐
放用基材をノニルフェノール（殺菌剤）に常温で２４時
間浸漬し膨潤させることにより、粒状の徐放性薬剤組成
物（１）を得た。この徐放性薬剤組成物（１）のノニル
フェノール含有率は８８．３重量％であった。A granular sustained-release drug composition (1) is prepared by immersing the substrate for sustained drug release in water of the present invention, which is made of the obtained crosslinked polymer (1), in nonylphenol (a disinfectant) at room temperature for 24 hours to swell it. I got it. The nonylphenol content of this sustained release drug composition (1) was 88.3% by weight.
実施例２
実施例１において、単量体（Ａ）としてヘキサデシルメ
タクリレート（ＳＰ値ニア、８）４９９３０部およびＮ
−オクチルメタクリルアミド（ＳＰ値：８．６）４９．
９３０部、架橋性単量体ＣＢ）としてジビニルベンゼン
０．１４０部を代わりに用いた以外は、実施例１と同様
の方法により粒径１００〜１０００μｍの架橋重合体（
２）を得な。Example 2 In Example 1, 49,930 parts of hexadecyl methacrylate (SP value near, 8) and N
-Octyl methacrylamide (SP value: 8.6) 49.
A crosslinked polymer with a particle size of 100 to 1000 μm (
Get 2).
得られた架橋重合体（２）からなる本発明の水中薬剤徐
放用基材をドデシルメルカプタン（防錆剤）に常温で２
４時間浸漬し膨潤させることにより、粒状の徐放性薬剤
組成物（２）を得な。この徐放性薬剤組成物（２）のド
デシルメルカプタン含有率は８７．１重量％であった。The substrate for sustained release of drugs in water of the present invention made of the obtained crosslinked polymer (2) was mixed with dodecyl mercaptan (rust inhibitor) at room temperature for 2 hours.
Granular sustained release drug composition (2) is obtained by soaking and swelling for 4 hours. The dodecyl mercaptan content of this sustained release drug composition (2) was 87.1% by weight.
実施例３
温度計およびガス導入管を備えたカラス製注型重合用型
（１５Ｘ１５ｘ０．５■）に、単量体（Ａ）としてドデ
シルアクリレート（ＳＰ値＝７゜９）９９．８２３部、
架橋性単量体（Ｂ）としてエチレングリコールジアクリ
レート０．１７７部および重合開始剤として２，２′−
アゾビスジメチルバレロニトリル０．１部からなる混合
溶液を注入し、窒素気流下５０℃で２時間加熱して重合
反′応を行い、その後８０’Ｃに昇温し、２時間維持し
て重合を完了させた６放冷後ゲル状物を型から剥離させ
、板状の架橋重合体（３）を得た。Example 3 99.823 parts of dodecyl acrylate (SP value = 7°9) as the monomer (A) was placed in a glass cast polymerization mold (15 x 15 x 0.5 cm) equipped with a thermometer and a gas inlet tube.
0.177 parts of ethylene glycol diacrylate as a crosslinkable monomer (B) and 2,2'- as a polymerization initiator.
A mixed solution consisting of 0.1 part of azobisdimethylvaleronitrile was injected and heated at 50°C for 2 hours under a nitrogen stream to perform a polymerization reaction.Then, the temperature was raised to 80'C and maintained for 2 hours for polymerization. After completion of 6 cooling, the gel-like material was peeled from the mold to obtain a plate-shaped crosslinked polymer (3).
得られた架橋重合体（３）からなる本発明の水中薬剤徐
放用基材をオレイン酸（殺菌剤）に常温で７日間浸漬し
膨潤させることにより、徐放性薬剤組成物（３）を得た
。この徐放性薬剤組成物（３）のオレイン酸含有率は９
１，０重量％であった。The sustained release drug composition (3) of the present invention, which is made of the obtained crosslinked polymer (3), is immersed in oleic acid (a disinfectant) for 7 days at room temperature to swell it. Obtained. The oleic acid content of this sustained release drug composition (3) is 9
It was 1.0% by weight.
実施例４
実施例３において、単量体（Ａ）としてｔ−ブチルスチ
レン（ＳＰ値＋７．９）５４．８８１部および゛１−デ
セン（ＳＰ値ニア、Ｏ＞４４．９０３部、架橋性単量体
（Ｂ）としてジビニルベンゼン０．２１６部を代わりに
用いる以外は、実施例３と同様の方法により架橋重合体
（４）を得た。Example 4 In Example 3, the monomers (A) were 54.881 parts of t-butylstyrene (SP value +7.9) and 1-decene (SP value near, O>44.903 parts, crosslinkable monomer). A crosslinked polymer (4) was obtained in the same manner as in Example 3, except that 0.216 parts of divinylbenzene was used instead as the polymer (B).
得られた架橋重合体（４）からなる本発明の水中薬剤徐
放用基材をトリブチルアミン（殺菌・防錆剤）に７日間
浸漬し膨潤させることより、徐放性薬剤組成物（４）を
得た。この徐放性薬剤組成物（４）のトリブチルアミン
含有率は８９．５重量％であった。A sustained release drug composition (4) is obtained by immersing the substrate for sustained drug release in water of the present invention, which is made of the obtained crosslinked polymer (4), in tributylamine (sterilizing/rusting agent) for 7 days to swell it. I got it. The tributylamine content of this sustained release drug composition (4) was 89.5% by weight.
実施例５
温度計、撹拌機、２本の滴下ロート、カス導入管および
還流冷却器を備えた５ ００ ｍｌフラスコにトルエン
１００重量部を仕込み、フラスコ内を窒素置換し、窒素
気流下に８０℃に加熱しな。その後、窒素気流下に同温
度に維持しながら、単量体（Ａ）としてドデシルアクリ
レート（ＳＰ値＝７゜９）１．８７．１３部、架橋性単
量体（Ｂ）としてテトラエチレングリコールジメタクリ
レート１２゜８６４部およびトルエン５０部からなる単
量体混合溶液を１．２０分かけて滴下し、同時にもう一
方の滴下ロートから２．２′−アゾビスジメチルバレロ
ニトリル１，５部およびトルエン４８．５部からなる重
合開始剤溶液を１８０分かけて滴下した。滴下終了後さ
らに同温度で６０分間維持して重合を完了させた。Example 5 100 parts by weight of toluene was charged into a 500 ml flask equipped with a thermometer, a stirrer, two dropping funnels, a waste introduction pipe, and a reflux condenser, the inside of the flask was replaced with nitrogen, and the temperature was heated to 80°C under a nitrogen stream. Do not heat. Thereafter, while maintaining the same temperature under a nitrogen stream, 1.87.13 parts of dodecyl acrylate (SP value = 7°9) was added as the monomer (A), and tetraethylene glycol dichloromethane was added as the crosslinkable monomer (B). A monomer mixed solution consisting of 12.864 parts of methacrylate and 50 parts of toluene was added dropwise over 1.20 minutes, and at the same time, 1.5 parts of 2.2'-azobisdimethylvaleronitrile and 48 parts of toluene were added from the other dropping funnel. .5 parts of a polymerization initiator solution was added dropwise over 180 minutes. After the dropwise addition was completed, the same temperature was further maintained for 60 minutes to complete the polymerization.
得られた架橋重合体（５）を含む粘稠液中の架橋重合体
（５）の含有量は５０．０重量％であった。The content of crosslinked polymer (5) in the obtained viscous liquid containing crosslinked polymer (5) was 50.0% by weight.
この架橋重合体（５）を含む粘稠液２０部にフタル酸ジ
ブチル（殺菌剤）２０部を添加混合した後、この混合液
を５■Ｘ２ｃ＋ｏのポリエチレン板の片面に厚さ１ｍｍ
に塗布し、次いで乾燥することによりトルエンを除去し
、架橋重合体（５）からなる本発明の水中薬剤徐放用基
材とフタル酸ジブチルからなる徐放性薬剤組成物（５）
で被覆されたポリエチレン板を得た。なお、このときポ
リエチレン板への徐放性薬剤組成物〈５）の塗布量は０
．６５ｇであった。After adding and mixing 20 parts of dibutyl phthalate (bactericide) to 20 parts of the viscous liquid containing this crosslinked polymer (5), spread the mixed solution on one side of a 5cm x 2c+o polyethylene plate to a thickness of 1mm.
The sustained release drug composition (5) is prepared by applying the toluene to the substrate and then drying to remove the toluene, and then forming the sustained release drug composition (5) consisting of the substrate for sustained drug release in water of the present invention made of the crosslinked polymer (5) and dibutyl phthalate.
A polyethylene plate coated with was obtained. At this time, the amount of sustained release drug composition <5) applied to the polyethylene plate was 0.
．． It was 65g.
実施例６
温度＃１、撹拌機、カス導入管、２本の滴下ロートおよ
び還流冷却器を備えた５ ００ ｍｌフラスコにポリオ
キシエチレン〈重合度１７）モノノニルフェニルエーテ
ル３部および水１００部を仕込み、３００ｒｐｌ′Ｎの
条件下に撹拌しながら窒素置換し、窒素気流下τこ７０
℃に加熱した。その後、窒素気流下に同温度を維持しな
がら、単量体（Ａ）としてオクチルメタクリレート（Ｓ
Ｐ値ニア、８）４９．４９７部、ステアリルメタクリレ
ート（ＳＰ値ニア、８）４９．４９７部、架橋性単量体
ＣＢ＞として１．６−ヘキサンジオールジアクリレート
１．００６部からなる単量体をポリオキシエチレン（重
合度１７）モノノニルフェニルエーテル３部を水１５０
部に溶解した水溶液中でホモジナイザーを用いて５００
０ ｒｐｍで１０分間混合して得た単量体水分散液２５
３部のうち５０．６部および過硫酸ナトリウム１部を水
５０部に溶解した過硫酸ナトリウム水溶液５１部のうち
５部をそれぞれ別の滴下ロートから一度に滴下し、重合
を開始した。その後、残りの単量体水分散液を１２０分
かけて滴下し、同時に残りの過硫酸ナトリウム水溶液を
２４０分かけて滴下した。滴下終了後さらに同温度で１
２０分間維持して重合を完結させ、架橋重合体（６）の
水分散体を得た。この架橋重合体（６）の平均粒径は０
．２μｍであり、得られた水分散体中の架橋重合体〈６
）の含有量は２５．３重量％であった。Example 6 3 parts of polyoxyethylene (degree of polymerization 17) monononylphenyl ether and 100 parts of water were placed in a 500 ml flask equipped with temperature #1, a stirrer, a waste inlet tube, two dropping funnels, and a reflux condenser. After charging, replace the nitrogen with stirring under the condition of 300 rpl'N, and heat for 70 minutes under a nitrogen stream.
heated to ℃. Then, while maintaining the same temperature under a nitrogen stream, octyl methacrylate (S) was used as the monomer (A).
P value near, 8) 49.497 parts, stearyl methacrylate (SP value near, 8) 49.497 parts, crosslinkable monomer CB> monomer consisting of 1.6-hexanediol diacrylate 1.006 parts 3 parts of polyoxyethylene (degree of polymerization 17) monononylphenyl ether 150 parts of water
Using a homogenizer in an aqueous solution dissolved in 500
Monomer aqueous dispersion 25 obtained by mixing at 0 rpm for 10 minutes
50.6 parts out of 3 parts and 5 parts out of 51 parts of an aqueous sodium persulfate solution prepared by dissolving 1 part sodium persulfate in 50 parts water were each dropped at once from separate dropping funnels to initiate polymerization. Thereafter, the remaining monomer aqueous dispersion was added dropwise over 120 minutes, and at the same time, the remaining sodium persulfate aqueous solution was added dropwise over 240 minutes. After dropping, continue at the same temperature for 1
The polymerization was maintained for 20 minutes to complete the polymerization, and an aqueous dispersion of crosslinked polymer (6) was obtained. The average particle size of this crosslinked polymer (6) is 0
．． 2 μm, and the crosslinked polymer <6
) content was 25.3% by weight.
この架橋重合体（６）を含む水分散体４０部にＱ−ジク
ロロベンゼン（殺虫・殺菌剤）２０部を添加し激しく混
合した後、この混合液を５ｃＩｎ×２■の塩化ビニル板
の片面に厚さ１ ｍ＋ｎに塗布し、次いで乾燥すること
により水を除去し、架橋重合体（６）からなる本発明の
水中薬剤徐放用基材と０ジクロロベンゼンからなる徐放
性薬剤組成物（６）で被覆された塩化ビニル板を得た。Add 20 parts of Q-dichlorobenzene (insecticide/bactericide) to 40 parts of the aqueous dispersion containing this crosslinked polymer (6), mix vigorously, and spread the mixture on one side of a 5 cIn x 2 cm vinyl chloride plate. It is coated to a thickness of 1 m+n, and then dried to remove water to form a sustained release drug composition (6) consisting of the substrate for underwater drug sustained release of the present invention consisting of a crosslinked polymer (6) and 0 dichlorobenzene. ) was obtained.
このときの塩化ビニル板への徐放性薬剤組成物（６）の
塗布量は０．５ｇであった。At this time, the amount of sustained release drug composition (6) applied to the vinyl chloride plate was 0.5 g.
実施例７
実施例３において、単量体（Ａ）としてノニルフェニル
アクリレート（ＳＰ値：８．３）７４−７９３部および
ヒドロキシエチルアクリレート（ｓｐ値： １０．３）
２４．９３１部、架橋性単量体（Ｂ）として１．６−ヘ
キサンジオールジアクリレート０．２７６部を代わりに
用いた以外は、実施例３と同様の方法により架橋重合体
（７）を得た。Example 7 In Example 3, 74-793 parts of nonyl phenyl acrylate (SP value: 8.3) and hydroxyethyl acrylate (SP value: 10.3) were used as the monomer (A).
A crosslinked polymer (7) was obtained in the same manner as in Example 3, except that 24.931 parts and 0.276 parts of 1.6-hexanediol diacrylate were used as the crosslinkable monomer (B). Ta.
得られた架橋重合体（７）からなる本発明の水中薬剤徐
放用基材をオレイン酸に常温で７日間浸漬し膨潤させる
ことにより、徐放性薬剤組成物（７）を得た。この徐放
性薬剤組成！Ｉ！Ｉ（７）の第レイン酸含有率は８２．
２重量％であった。A sustained release drug composition (7) was obtained by immersing the substrate for sustained drug release in water of the present invention made of the obtained crosslinked polymer (7) in oleic acid at room temperature for 7 days to swell it. This sustained release drug composition! I! The leic acid content of I(7) is 82.
It was 2% by weight.
比較例１
実施例３において、ドデシルアクリレートの量を７７．
９２２部に、エチレンクリコールジアクリレートの量を
２２．０７８部にそれぞれ変更した以外は、実施例３と
同様の方法により比較架橋重合体（１）を得な。Comparative Example 1 In Example 3, the amount of dodecyl acrylate was changed to 77.
Comparative crosslinked polymer (1) was obtained in the same manner as in Example 3, except that the amount of ethylene glycol diacrylate was changed to 922 parts and 22.078 parts.
得られた比較架橋重合体（］）をオレイン酸に常温で７
日間浸漬することにより比較薬剤組成物（１）を得な。The obtained comparative crosslinked polymer (]) was added to oleic acid at room temperature for 7
Comparative drug composition (1) was obtained by soaking for 1 day.
しかし、この浸漬時に比較架橋重合体（１）は膨潤せず
、この比較薬剤組成物（１）のオレイン酸含有率は２．
１重量％であった。However, the comparative crosslinked polymer (1) did not swell during this immersion, and the oleic acid content of this comparative drug composition (1) was 2.
It was 1% by weight.
比較例２
実施例３において、ドデシルアクリレート９９７７８部
のかわりにドデシルアクリレート３９８８４部およびヒ
ドロキシエチルアクリレート（ＳＰ値＋ １０．３＞５
９．８２６部を用い、エチレンクリコールジアクリレー
トの量を０．２９０部に変更した以外は、実施例３と同
様の方法により比較架橋重合体（２）を得な。Comparative Example 2 In Example 3, 39,884 parts of dodecyl acrylate and hydroxyethyl acrylate (SP value + 10.3>5) were used instead of 99,778 parts of dodecyl acrylate.
Comparative crosslinked polymer (2) was obtained in the same manner as in Example 3, except that 9.826 parts of ethylene glycol diacrylate was used and the amount of ethylene glycol diacrylate was changed to 0.290 parts.
得られた比較架橋重合体く２）をオレイン酸に常温で７
日間浸漬することにより比較薬剤組成物く２）を得た。The obtained comparative crosslinked polymer 2) was added to oleic acid at room temperature for 7
Comparative drug composition 2) was obtained by immersion for 1 day.
しかし、この浸漬時に比較架橋重合体（２）は大きく膨
潤せず、この比較薬剤組成物（２）のオレイン酸含有率
は１５，２重量％であった。However, the comparative crosslinked polymer (2) did not swell significantly during this immersion, and the oleic acid content of this comparative drug composition (2) was 15.2% by weight.
比較例３
実施例５においてテトラエヂレンクリ＝７−ルジメタク
リレートを用いなかった以外は、実施例５と同様の方法
により比較重合体（３）を含む溶液を得な。Comparative Example 3 A solution containing comparative polymer (3) was obtained in the same manner as in Example 5, except that tetraethylene chloride-7-yl dimethacrylate was not used.
得られた比較重合体（３）を含む溶液を実施例５と同様
の方法によりフタル酸ジブデルと混合したのちポリエチ
レン板に塗布し、次いで乾燥することによりトルエンを
除去し、比較重合体（３）とフタル酸ジブチルからなる
比較薬剤組成物（３）で被覆されたポリエチレン板を得
た、このときのポリエチレン板への比較薬剤組成物（３
）の塗布量は０．６５ｇであった。A solution containing the obtained comparative polymer (3) was mixed with dibdel phthalate in the same manner as in Example 5, and then applied to a polyethylene plate, and then dried to remove toluene and form a comparative polymer (3). A polyethylene board was obtained which was coated with a comparative drug composition (3) consisting of dibutyl phthalate and dibutyl phthalate.
) was applied in an amount of 0.65 g.
実施例８
実施例１〜２で得られた徐放性薬剤組成物（１）〜（２
）の各々１００ｇを内径３ａｎ長さ２０ａｎのステンレ
ス製カラム内に充填した後、両末端に２００メツシユの
金網を装着し、次いで一方より水を１０ｍ１／Ｆｉｎの
流量でカラム内に流し続けた。Example 8 Sustained release drug compositions (1) to (2) obtained in Examples 1 to 2
) was packed into a stainless steel column with an inner diameter of 3 ann and a length of 20 ann, a wire mesh of 200 mesh was attached to both ends, and then water was continued to flow into the column from one end at a flow rate of 10 ml/Fin.
このときカラム出口より流出する水をサンプリングし、
水中の薬剤濃度を１５日毎３カ月に渡りカスクロマトグ
ラフ法により経時的に定量した。その結果を第１表に示
す。At this time, sample the water flowing out from the column outlet,
The drug concentration in water was quantified over time by a gas chromatography method every 15 days for 3 months. The results are shown in Table 1.
第１表
２つ
実施例９
実施例３，４および７により得られた徐放性薬剤組成物
（３）、（４）および（７）並びに比較例１〜２で得ら
れた比較薬剤組成物（１）〜（２）の各々Ｌｏｇをポリ
エステル製不織布からなる袋中に充填し、各々６個を同
時に海面下１ｍの海水中に浸漬した。浸漬後１５日毎に
各薬剤組成物の入った袋を１個とりだし、薬剤組成物中
の薬剤成分をテトラヒドロフランを用いたソックスレー
抽出により抽出し抽出液中の薬剤成分量をカスクロマト
グラフ法により定量することにより、薬剤組成物中に残
存した薬剤量を定量した。次いで薬剤成分の放出率を下
記の計算式により算出し、その結果を第２表に示した。Table 1 Two Example 9 Sustained release drug compositions (3), (4) and (7) obtained in Examples 3, 4 and 7 and comparative drug compositions obtained in Comparative Examples 1 and 2 Each Log of (1) to (2) was filled into a bag made of polyester nonwoven fabric, and six of each were simultaneously immersed in seawater 1 m below the sea surface. After soaking, one bag containing each drug composition is taken out every 15 days, the drug components in the drug composition are extracted by Soxhlet extraction using tetrahydrofuran, and the amount of drug components in the extract is quantified by Cass chromatography. The amount of drug remaining in the drug composition was quantified. Next, the release rate of the drug component was calculated using the following formula, and the results are shown in Table 2.
放出率（％）−（１−（浸漬後の残存薬剤量／浸漬前の
薬剤成分量） ） Ｘ ｉ ００実施例１０
実施例５〜６により得られな徐放性薬剤組成物（５）〜
（６）および比較例３で得られた比較薬剤組成物（３）
で被覆されたポリエチレンまたは塩化ビニル板の各々６
枚を面積５０ｍＸ２０ｍ深さ１ｍの淡水プール内に浸漬
し、浸漬後１５日毎に各薬剤組成物で被覆された板を１
枚とりだし、薬剤組成物中の薬剤成分をテトラヒドロフ
ランを用いたソックスレー抽出により抽出し抽出溶液中
の薬剤成分量をカスクロマトグラフ法により定量するこ
とにより、薬剤組成物中に残存した薬剤量を定量した。Release rate (%) - (1 - (residual drug amount after immersion/drug component amount before immersion)) X i 00 Example 10 Sustained release drug composition (5) obtained in Examples 5-6
(6) and comparative drug composition (3) obtained in Comparative Example 3
6 each of polyethylene or vinyl chloride plates coated with
The plate was immersed in a freshwater pool with an area of 50 m x 20 m and a depth of 1 m, and every 15 days after immersion, 1 plate coated with each drug composition was removed.
The drug components in the drug composition were extracted by Soxhlet extraction using tetrahydrofuran, and the amount of drug components in the extracted solution was determined by gas chromatography to determine the amount of drug remaining in the drug composition.
次いで薬剤成分の放出率を下記の計算式により算出し、
その結果を第３表に示した。Next, the release rate of the drug component was calculated using the following formula,
The results are shown in Table 3.
放出率（％）−（１−（浸漬後の残存薬剤ｉ／漫浸漬の
薬剤成分量）ｌ Ｘ１００
第２表
第３表Release rate (%) - (1 - (residual drug i after immersion/drug component amount after continuous immersion) l X100 Table 2 Table 3
Claims (1)
主成分としてなる分子中に１個の重合性不飽和基を有す
る単量体（Ａ）８０〜９９．９９９重量％および分子中
に少なくとも２個の重合性不飽和基を有する架橋性単量
体（Ｂ）０．００１〜２０重量％（ただし単量体（Ａ）
および（Ｂ）の合計は１００重量％である）からなる単
量体成分を重合して得られる架橋重合体（ I ）からな
る水中薬剤徐放用基材。 ２、単量体（Ａ）が、少なくとも１個の炭素数３〜３０
の脂肪族炭化水素基を有し、かつアルキル（メタ）アク
リレート、アルキルアリール（メタ）アクリレート、ア
ルキル（メタ）アクリルアミド、アルキルアリール（メ
タ）アクリルアミド、アルキルスチレンおよびα−オレ
フィンからなる群より選ばれる少なくとも１種の不飽和
化合物（ａ）を主成分としてなるものである請求項１記
載の水中薬剤徐放用基材。 ３、単量体（Ａ）が、請求項２記載の不飽和化合物（ａ
）を単量体（Ａ）中に５０重量％以上含有してなるもの
である請求項２記載の水中薬剤徐放用基材。[Scope of Claims] 1. Monomer (A) having one polymerizable unsaturated group in the molecule consisting mainly of a monomer having a solubility parameter (SP value) of 9 or less 80 to 99.999 Weight% and crosslinkable monomer (B) having at least two polymerizable unsaturated groups in the molecule 0.001 to 20% by weight (however, monomer (A)
and (B), the total of which is 100% by weight). 2. Monomer (A) has at least one carbon number of 3 to 30
and at least one selected from the group consisting of alkyl (meth)acrylate, alkylaryl (meth)acrylate, alkyl (meth)acrylamide, alkylaryl (meth)acrylamide, alkylstyrene, and α-olefin. The substrate for sustained drug release in water according to claim 1, which comprises one type of unsaturated compound (a) as a main component. 3. The monomer (A) is the unsaturated compound (a) according to claim 2.
) in the monomer (A) in an amount of 50% by weight or more.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2159923A JPH0482803A (en) | 1990-06-20 | 1990-06-20 | Substrate for sustained releasing chemical in water |
| AU70039/91A AU651567B2 (en) | 1990-01-29 | 1991-01-19 | Oil-absorbent polymer and use therefor |
| AT9191300645T ATE105209T1 (en) | 1990-01-29 | 1991-01-29 | OIL ABSORBENT POLYMER AND ITS USE. |
| DE69101851T DE69101851T2 (en) | 1990-01-29 | 1991-01-29 | Oil absorbing polymer and its use. |
| EP91300645A EP0441512B1 (en) | 1990-01-29 | 1991-01-29 | Oil- absorbent polymer and use therefor |
| US08/126,731 US5374600A (en) | 1990-01-29 | 1993-09-27 | Oil-absorbent polymer and use therefor |
| US08/579,888 US5641847A (en) | 1990-01-29 | 1995-12-28 | Oil-absorbent polymer and use therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2159923A JPH0482803A (en) | 1990-06-20 | 1990-06-20 | Substrate for sustained releasing chemical in water |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0482803A true JPH0482803A (en) | 1992-03-16 |
Family
ID=15704110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2159923A Pending JPH0482803A (en) | 1990-01-29 | 1990-06-20 | Substrate for sustained releasing chemical in water |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0482803A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10287509A (en) * | 1997-04-14 | 1998-10-27 | Rohm & Haas Co | Composition for controlling pest |
| JP2010195782A (en) * | 2002-05-29 | 2010-09-09 | L'air Liquide Sante Internatl | Disinfectant with activity against hepatitis b virus |
| US10070650B2 (en) | 2008-09-25 | 2018-09-11 | Vive Crop Protection Inc. | Methods to produce polymer nanoparticles and formulations of active ingredients |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61236702A (en) * | 1985-04-10 | 1986-10-22 | Nippon Paint Co Ltd | Fine resin particle having resistance to harmful organism |
-
1990
- 1990-06-20 JP JP2159923A patent/JPH0482803A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61236702A (en) * | 1985-04-10 | 1986-10-22 | Nippon Paint Co Ltd | Fine resin particle having resistance to harmful organism |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10287509A (en) * | 1997-04-14 | 1998-10-27 | Rohm & Haas Co | Composition for controlling pest |
| JP2010195782A (en) * | 2002-05-29 | 2010-09-09 | L'air Liquide Sante Internatl | Disinfectant with activity against hepatitis b virus |
| JP2013253081A (en) * | 2002-05-29 | 2013-12-19 | L'air Liquide Sante Internatl | Disinfectant with activity against hepatitis b virus |
| US10070650B2 (en) | 2008-09-25 | 2018-09-11 | Vive Crop Protection Inc. | Methods to produce polymer nanoparticles and formulations of active ingredients |
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