JP2005336166A - 貼付剤用粘着剤及びその製造方法 - Google Patents
貼付剤用粘着剤及びその製造方法 Download PDFInfo
- Publication number
- JP2005336166A JP2005336166A JP2005114586A JP2005114586A JP2005336166A JP 2005336166 A JP2005336166 A JP 2005336166A JP 2005114586 A JP2005114586 A JP 2005114586A JP 2005114586 A JP2005114586 A JP 2005114586A JP 2005336166 A JP2005336166 A JP 2005336166A
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- Prior art keywords
- acid
- adhesive
- acrylate polymer
- acrylate
- salt
- 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.)
- Granted
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 22
- 239000007933 dermal patch Substances 0.000 title abstract 3
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims abstract description 117
- -1 alkali metal salt Chemical class 0.000 claims abstract description 92
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 85
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 229920000642 polymer Polymers 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 33
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 239000012530 fluid Substances 0.000 claims description 77
- 239000000853 adhesive Substances 0.000 claims description 67
- 230000001070 adhesive effect Effects 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 33
- 238000001035 drying Methods 0.000 claims description 30
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 17
- 239000001569 carbon dioxide Substances 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 20
- 239000003814 drug Substances 0.000 abstract description 20
- 230000014759 maintenance of location Effects 0.000 abstract description 7
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 235000002639 sodium chloride Nutrition 0.000 description 59
- 238000006116 polymerization reaction Methods 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 238000004132 cross linking Methods 0.000 description 38
- 239000002253 acid Substances 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 21
- 229940048053 acrylate Drugs 0.000 description 19
- 239000000499 gel Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 229920001223 polyethylene glycol Polymers 0.000 description 18
- 229940079593 drug Drugs 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002202 Polyethylene glycol Substances 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003431 cross linking reagent Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 235000002906 tartaric acid Nutrition 0.000 description 9
- 239000011975 tartaric acid Substances 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229940083542 sodium Drugs 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 235000014655 lactic acid Nutrition 0.000 description 7
- 239000004310 lactic acid Substances 0.000 description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- 229960004889 salicylic acid Drugs 0.000 description 7
- 229940047670 sodium acrylate Drugs 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 6
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 6
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 6
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 6
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 5
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
- 241000723346 Cinnamomum camphora Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004166 Lanolin Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 229960000846 camphor Drugs 0.000 description 5
- 229930008380 camphor Natural products 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
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- 235000015165 citric acid Nutrition 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
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- 239000002245 particle Substances 0.000 description 5
- 239000004584 polyacrylic acid Substances 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 4
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- 229920002126 Acrylic acid copolymer Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
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- 108010010803 Gelatin Proteins 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
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- 239000001273 butane Substances 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
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- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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- 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
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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Images
Abstract
【解決手段】構成単位として、(1)アクリル酸塩(アンモニウム塩又はアルカリ金属塩)単量体、(2)アクリル酸単量体、(3)(1)及び(2)以外の不飽和単量体、を含み、(1)のアクリル酸塩単量体単位を5モル%以上含有しているアクリル酸塩系重合体からなり、β−ヒドロキシプロピオン酸(塩)含有量が重合体固形分当たり5000ppm以下である貼付剤用粘着剤、その製造方法及びその貼付剤用粘着剤とアルミニウム化合物と水を含む貼付剤用粘着剤組成物。
【選択図】なし
Description
1.アクリル酸(塩)を単量体単位として5モル%以上含有しているアクリル酸塩系重合体からなり、β−ヒドロキシプロピオン酸(塩)含有量が重合体固形分当たり5000ppm以下であることを特徴とする貼付剤用粘着剤。
2.繰り返し単位が、一般式(1)、(2)及び(3)
3.前記Mがナトリウムで、かつ前記繰り返し単位(1)及び(2)の割合が(1)/(2)=20/80〜80/20(モル比)の範囲にあり、前記繰り返し単位(3)を含まない前記2記載の貼付剤用粘着剤。
4.アクリル酸塩系重合体が分子内架橋されている前記1記載の貼付剤用粘着剤。
5.アクリル酸塩系重合体がアクリル酸ナトリウム−N−ビニルアセトアミド共重合体である前記1記載の貼付剤用粘着剤。
6.前記1乃至5のいずれか1項に記載の貼付剤用粘着剤を製造する方法において、アクリル酸塩系重合体を40〜160℃以下の温度に管理する乾燥工程を含むことを特徴とする貼付剤用粘着剤の製造方法。
7.前記1乃至5のいずれか1項に記載の貼付剤用粘着剤を製造する方法において、アクリル酸塩系重合体乾燥工程を含み、前記乾燥工程前のアクリル酸塩系重合体中の含水率を40%以下に管理することを特徴とする貼付剤用粘着剤の製造方法。
8.前記乾燥工程の前にアクリル酸塩系重合体を予め水溶性有機溶媒にて脱水する脱水工程を含む前記7記載の貼付剤用粘着剤の製造方法。
9.さらに亜臨界流体及び/または超臨界流体と接触させてβ−ヒドロキシプロピオン酸(塩)含有量を低減する工程を含む前記6乃至8のいずれか1項に記載の貼付剤用粘着剤の製造方法。
10.亜臨界流体及び/または超臨界流体が二酸化炭素である前記9記載の貼付剤用粘着剤の製造方法。
11.前記1乃至5のいずれか1項に記載の貼付剤用粘着剤を0.1〜20質量%、アルミニウム化合物を0.01〜20質量%及び水を1〜99.89質量%含むことを特徴とする貼付剤用粘着剤組成物。
本発明の貼付剤用粘着剤において、アクリル酸塩系重合体中のβ−ヒドロキシプロピオン酸(塩)の含有量は、固形分あたり5000ppm以下であることが必須であり、好ましくは1000ppm以下、更に好ましくは500ppm以下、最も好ましくは100ppm以下である(なお、本発明でβ−ヒドロキシプロピオン酸(塩)の含有量とは、β−ヒドロキシプロピオン酸及びβ−ヒドロキシプロピオン酸塩の合計含有量を指す。)。β−ヒドロキシプロピオン酸(塩)の含有量が5000ppmを越える場合、得られた貼付剤用粘着剤は架橋が不十分もしくは過度に行われてしまい、粘着層の硬さが不安定になるため、結果として、粘着力や薬物の吸収性も不安定になってしまう。
また、アクリル酸がナトリウム塩で、かつ前記繰り返し単位(1)及び(2)の割合が(1)/(2)=20/80〜80/20(モル比)の範囲にあり、前記繰り返し単位(3)を含まない重合体であることが好ましい。
使用後のエントレーナーは、精製操作(例えば、蒸留操作、吸着操作等)を経て再使用することができる。また、精製操作を経ること無く再使用してもよい。
例えば、アクリル酸塩系重合体、不純物、エントレーナー、亜臨界流体及び/または超臨界流体を、所望の成分及び/または成分群に分離してもよい。具体的な分離方法としては、例えば、温度及び/または圧力の調節によって、アクリル酸塩系重合体、β−ヒドロキシプロピオン酸(塩)、β−ヒドロキシプロピオン酸(塩)以外の不純物、エントレーナー、亜臨界流体及び/または超臨界流体のうち、少なくとも一部が実質的に分離される条件に設定する方法が挙げられる。設定温度条件及び/または圧力条件は、複数段階であってもよい。分離された成分及び/または成分群は、その少なくとも一部を再度使用してもよい。また再使用前に、さらなる分離操作(例えば、蒸留操作、吸着操作等)を行ってもよい。
(I)医薬品:例えば経皮吸収用製剤、経粘膜吸収用製剤。
(II)医療用具:例えば発熱時の患部の冷却剤、創傷治癒剤、治療用パット、手術用吸液剤、やけど治癒剤。
(III)化粧品、医薬部外品:例えばフェイスマスク、パック剤、サンタン用品、ニキビ用品。
(IV)雑貨:例えば熱さまし用冷却シート。
アルミニウム化合物の量を変化させることで粘着性を自由にコントロールすることができる。アルミニウム化合物は組成物全量に対して0.01〜20%の範囲で添加され、さらに好ましくは0.1〜10%の範囲がよい。添加量が0.01%未満の場合には架橋が不十分となって基剤に糸引きが生じる。20%を超えるとゲルが硬くなりすぎ、組成物の粘着性が劣ってくる。
(e)催眠鎮静剤:フェノバルビタール、アモバルビタール、シクロバルビタール、ロラゼパム、ハロペリドール等。
(f)精神安定剤:フルフェナジン、テオリダジン、ジアゼパム、フルニトラゼパム、クロルプロマジン等。
(h)降圧利尿剤:ハイドロサイアザイド、シクロペンチアザイド等。
(i)抗生物質:ペニシリン、テトラサイクリン、オキシテトラサイクリン、硫酸フラジオマイシン、エリスロマイシン、クロラムフェニコール等。
(k)抗菌性物質:塩化ベンザルコニウム、ニトロフラゾン、ナイスタチン、アセトスルフアミン、クロトリマゾール等。
(l)ビタミン剤:ビタミンA、エルゴカルシフェロール、コレカルシフェロール、オクトチアミン、リボフラビン酪酸エステル等。
(n)冠血管拡張剤:ニトログリセリン、ニトログリコール、イソソルビジナイトレート、エリスルトールテトラナイトレート、ペンタエリスリトールテトラナイトレート、プロパチルナイトレート等。
(o)抗ヒスタミン剤:塩酸ジフェンヒドラミン、クロルフェニラミン、ジフェニルイミダゾール等。
塩酸エフェドリン等。
(q)性ホルモン:プロゲステロン、エストラジオール等。
(r)抗うつ剤:ドキセピン等。
(t)麻薬性鎮痛剤:塩酸モルヒネ、塩酸エチルモルヒネ、硫酸モルヒネ、塩酸コカイン、塩酸ペチジン、リン酸コデイン、リン酸ジヒドロコデイン、クエン酸フェンタニール、スフェンタニール、塩酸メペリジン等。
(2)収れん剤:クエン酸、酒石酸、乳酸、塩化アルミニウム、硫酸アルミニウム、アラントインクロルヒドロキシアルミニウム、アラントインジヒドロキシアルミニウム、アルミニウムフェノールスルホン酸、パラフェノールスルホン酸亜鉛、硫酸亜鉛、アルミニウムクロロヒドロオキシド等。
(3)保湿剤:グリセリン、プロピレングリコール、1,3−ブチレングリコール、ソルビトール、ポリグリセリン、ポリエチレングリコール、ジプロピレングリコール等の多価アルコール類、乳酸ナトリウム等のNMF成分、ヒアルロン酸、コラーゲン、ムコ多糖類、コンドロイチン硫酸等の水溶性高分子等。
(6)止痒剤:カンフル、チモール、メントール、ポリオキシエチレンラウリルエーテル、抗ヒスタミン剤、アミノ安息香酸エチル等。
(7)角質軟化剥離剤:イオウ、チオキソロン、硫化セレン、サリチル酸、レゾルシン等。
(8)誤食防止物質:唐辛子粉、トウガラシエッセンス等。
(9)粉体原料:モンモリロラート、無水ケイ酸、石コウ、カーボンブラック、珪藻土、ベンガラ、炭酸カルシウム、ヒドロタルサイト、タルク、ガラス、カオリン、ベントナイト、金属石鹸、エーロジル、雲母チタン、オキシ塩化ビスマス、魚鱗箔等、亜鉛華、二酸化チタン等。
(13)香料:芥子油、オレンジ油、胡椒油、ジャスミン油、杉油、ショウブ油、テルピン油、橙花油、バラ油、ユーカリ油、ライム油、レモン油、和種ハッカ油、ローズマリー油等の植物性香料、ムスク、レイビョウコウ、カイリコウ、リュウゼンコウ等の動物性香料、ブロモスチロール、ピネン、リモネン等の炭化水素系香料、ベンジルアルコール、l−メントール等のアルコール系香料、酢酸エチル、サリチル酸メチル等のエステル類系香料、ベンズアルデヒド、サリチルアルデヒド等のアルデヒド類系香料、カンファー、ムスコン、ムスクケトン、l−メントン等のケトン類系香料、サフロール等のエーテル類系香料、チモール等のフェノール類系香料、ラクトン類系香料、フェニル酢酸等の酸系香料、インドール等の窒素化合物系香料等。
(17)キレート剤:エデト酸塩、ピロリン酸塩、ヘキサメタリン酸塩、クエン酸、酒石酸、グルコン酸等。
(18)紫外線散乱剤:酸化チタン、カオリン、タルク等。
本発明の貼付剤用粘着剤を用いて貼付剤を製造するには、各種原料を混合後、ゾル状態で適当な型に流し込み、そこで架橋させて成形するか、架橋後のゲルを直接適当な成形機、打錠機等を用いて各種成形物に調製する。原料の混合は、例えばニーダー、コニーダー、ニーダールーダー、アジホモミキサー、プラネタリーミキサー、ダブルプラネタリーミキサー等を適宜に選択使用することにより行うことができる。
実施例1:
2Lのセパラブルフラスコにアクリル酸、アクリル酸ナトリウム及び水を仕込んだ。なお、アクリル酸/アクリル酸ナトリウム比は50/50(モル比)とした。重合開始剤として、過硫酸アンモニウム、重合促進剤として重亜硫酸カリウム、連鎖移動剤として次亜リン酸ナトリウムを加え、重合開始温度20度で10時間重合した。得られた寒天状のゲル体をミンチし、エタノールで脱水し(エタノール脱水後のミンチ中の含水率35%)、窒素気流下210℃にて丸一日熱風乾燥した。
ポリマー中のβ−ヒドロキシプロピオン酸をアセトニトリル水溶液で抽出し、HPLCで定量した。溶離液として0.1%のリン酸水溶液、カラムとしてSHODEX KC−811(昭和電工(株))を用い、カラム温度40℃、218nmでUV検出した。その結果、β−ヒドロキシプロピオン酸は30ppmであった。
2Lのセパラブルフラスコにアクリル酸、アクリル酸ナトリウム及び水を仕込んだ。なお、アクリル酸/アクリル酸ナトリウム比は50/50(モル比)とした。重合開始剤として、過硫酸アンモニウム、重合促進剤として重亜硫酸カリウム、連鎖移動剤として次亜リン酸ナトリウムを加え、重合開始温度20度で10時間重合した。得られた寒天状のゲル体をミンチし、210℃にて丸一日熱風乾燥した。
ポリマー中のβ−ヒドロキシプロピオン酸の含有量を上記と同様に定量したところ、7800ppmであった。
2Lのセパラブルフラスコにアクリル酸ナトリウム及び水を仕込んだ。重合開始剤として、過硫酸ナトリウム、重合促進剤として亜硫酸ナトリウム、連鎖移動剤として次亜リン酸カリウムを加え、重合開始温度10℃で15時間重合した。得られた寒天状のゲル体をミンチし、50℃にて丸一日熱風乾燥した。
ポリマー中のβ−ヒドロキシプロピオン酸の含有量を上記と同様に定量したところ、110ppmであった。
2Lのセパラブルフラスコにアクリル酸ナトリウム及び水を仕込んだ。重合開始剤として、過硫酸ナトリウム、重合促進剤として亜硫酸ナトリウム、連鎖移動剤として次亜リン酸カリウムを加え、重合開始温度10℃で15時間重合した。得られた寒天状のゲル体をミンチし、200℃にて丸一日熱風乾燥した。
ポリマー中のβ−ヒドロキシプロピオン酸の含有量を上記と同様に定量したところ、8600ppmであった。
アクリル酸ナトリウム−N−ビニルアセトアミド共重合体(共重合比:アクリル酸ナトリウム/N−ビニルアセトアミド=40/60質量比)を水溶液重合した。得られた寒天状のゲル(水分75%)を200℃で丸一日熱風乾燥し、粉砕して得た粉末を、炭酸ガス超臨界流体を用い精製した。精製には昭和炭酸(株)の超臨界CO2抽出装置(標準型)を用いた。なお、精製前のβ−ヒドロキシプロピオン酸濃度は6700ppmであった。
処理条件は500mLの抽出器に重合体100gを仕込み、1000NLの炭酸ガスを1時間流通した。条件は40℃、30M・Paとし、一回のみの流通とした。なお共重合体が微細粉体であるため、昇圧時に抽出器内でのサンプルの拡散を抑制するため、炭酸ガスを抽出器上下から流通し、圧力は10M・Paまで昇圧した。10M・Pa以上では下部経路からのみ炭酸ガスを流通した。減圧条件は4M・Paまで10〜12分(500〜1000NL/h)かけて落とし、4M・Paから大気圧まで5分(500NL/h以下)かけて落とした。処理後のサンプルの膨張は見られなかった。
ポリマー中のβ−ヒドロキシプロピオン酸の含有量を上記と同様に定量したところ、10ppmであった。
ポリアクリル酸架橋体(カーボポール934,NOVEON社,粉末)を、炭酸ガス超臨界流体を用い精製した。精製には昭和炭酸(株)の超臨界CO2抽出装置(標準型)を用いた。なお、精製前のβ−ヒドロキシプロピオン酸濃度は5600ppmであった。
処理条件は500mLの抽出器に重合体30gを仕込み、1000NLの炭酸ガスを5時間流通した。条件は40℃、15M・Paとし、エントレーナーとしてエタノールを添加した。流通は二回行った。なお重合体が微細粉体であるため、昇圧時に抽出器内でのサンプルの拡散を抑制するため、炭酸ガスを抽出器上下から流通し、圧力は10M・Paまで昇圧した。10M・Pa以上では下部経路からのみ炭酸ガスを流通した。なお減圧条件は4M・Paまで10〜12分(500〜1000NL/h)かけて落とし、4M・Paから大気圧まで5分(500NL/h以下)かけて落とした。処理後のサンプルの膨張は見られなかった。
ポリマー中のβ−ヒドロキシプロピオン酸の含有量を上記と同様に定量したところ、350ppmであった。
実施例1で得られたアクリル酸−アクリル酸ナトリウム共重合体(0.2%水溶液粘度450mPa・s)及び比較例1で得られたアクリル酸−アクリル酸ナトリウム共重合体(0.2%水溶液粘度463mPa・s)を用い以下の配合及び処方で架橋実験を行った。
[配合]
アクリル酸−アクリル酸ナトリウム共重合体 16部
グリセリン 120部
酒石酸 0.8部
乾燥水酸化アルミニウムゲル 1.6部
水 240部
[処方]
水(240g)及び酒石酸(0.8g)の混合液に、ポリアクリル酸ナトリウム重合体(16g)とグリセリン(120g)及び乾燥水酸化アルミニウムゲル(1.6g)の分散液を加え混合し、均一になるまで練合した。得られたゾルを成形し密封したのち約20℃下10日間熟成した。架橋の度合いを評価するパラメーターとして、ゲル強度を測定した。すなわち、デジタルフォースゲージ(日本電産シンポ DFG−0.2K)及びその専用スタンドを用い、カードテンションメーターの原理で測定した。官能軸(アルミニウム製)は直径10mm、高さ12mmの円柱とし、移動距離は30mm、移動速度は5mm/secとした。またゲルは樹脂製サンプル瓶にゾル状態の時に流し込み、測定はn=3で実施した。
なお、本測定法によるゲル強度の測定値と触指による感応テストとの相関は以下の通りである。
実施例2で得られたポリアクリル酸ナトリウム(0.2%水溶液粘度560mPa・s)及び比較例2で得られたポリアクリル酸ナトリウム(0.2%水溶液粘度551mPa・s)を用い以下の配合及び処方で架橋実験を行った。
[配合]
ポリアクリル酸ナトリウム 16部
グリセリン 120部
乳酸 1.6部
グリシナール 0.4部
水 240部
[処方]
水(240g)及び乳酸(1.6g)の混合液に、ポリアクリル酸ナトリウム(16g)とグリセリン(120g)及びグリシナール(0.4g)の分散液を加え混合し、均一になるまで練合した。得られたゾルを成形し密封したのち約20℃下10日間熟成した。ゲル強度を架橋実験1と同様にして測定した。結果を図2に示す。β−ヒドロキシプロピオン酸(塩)含有量の多い比較例2のポリマーはゲル化の速度(架橋の度合いの進行度)が遅いことが分かる。
Claims (11)
- アクリル酸(塩)を単量体単位として5モル%以上含有しているアクリル酸塩系重合体からなり、β−ヒドロキシプロピオン酸(塩)含有量が重合体固形分当たり5000ppm以下であることを特徴とする貼付剤用粘着剤。
- 前記Mがナトリウムで、かつ前記繰り返し単位(1)及び(2)の割合が(1)/(2)=20/80〜80/20(モル比)の範囲にあり、前記繰り返し単位(3)を含まない請求項2記載の貼付剤用粘着剤。
- アクリル酸塩系重合体が分子内架橋されている請求項1記載の貼付剤用粘着剤。
- アクリル酸塩系重合体がアクリル酸ナトリウム−N−ビニルアセトアミド共重合体である請求項1記載の貼付剤用粘着剤。
- 請求項1乃至5のいずれか1項に記載の貼付剤用粘着剤を製造する方法において、アクリル酸塩系重合体を40〜160℃以下の温度に管理する乾燥工程を含むことを特徴とする貼付剤用粘着剤の製造方法。
- 請求項1乃至5のいずれか1項に記載の貼付剤用粘着剤を製造する方法において、アクリル酸塩系重合体乾燥工程を含み、前記乾燥工程前のアクリル酸塩系重合体中の含水率を40%以下に管理することを特徴とする貼付剤用粘着剤の製造方法。
- 前記乾燥工程の前にアクリル酸塩系重合体を予め水溶性有機溶媒にて脱水する脱水工程を含む請求項7記載の貼付剤用粘着剤の製造方法。
- さらに亜臨界流体及び/または超臨界流体と接触させてβ−ヒドロキシプロピオン酸(塩)含有量を低減する工程を含む請求項6乃至8のいずれか1項に記載の貼付剤用粘着剤の製造方法。
- 亜臨界流体及び/または超臨界流体が二酸化炭素である請求項9記載の貼付剤用粘着剤の製造方法。
- 請求項1乃至5のいずれか1項に記載の貼付剤用粘着剤を0.1〜20質量%、アルミニウム化合物を0.01〜20質量%及び水を1〜99.89質量%含むことを特徴とする貼付剤用粘着剤組成物。
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