JPWO2008143136A1 - オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 - Google Patents
オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 Download PDFInfo
- Publication number
- JPWO2008143136A1 JPWO2008143136A1 JP2009515191A JP2009515191A JPWO2008143136A1 JP WO2008143136 A1 JPWO2008143136 A1 JP WO2008143136A1 JP 2009515191 A JP2009515191 A JP 2009515191A JP 2009515191 A JP2009515191 A JP 2009515191A JP WO2008143136 A1 JPWO2008143136 A1 JP WO2008143136A1
- Authority
- JP
- Japan
- Prior art keywords
- trehalose
- succinic acid
- ester salt
- octenyl succinic
- composition
- 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
Links
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 title claims abstract description 77
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 title claims abstract description 76
- -1 octenyl succinic acid trehalose ester salt Chemical class 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 239000003599 detergent Substances 0.000 title description 13
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims abstract description 45
- 238000004140 cleaning Methods 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- GUOCOOQWZHQBJI-UHFFFAOYSA-N 4-oct-7-enoxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OCCCCCCC=C GUOCOOQWZHQBJI-UHFFFAOYSA-N 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 239000002280 amphoteric surfactant Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000002537 cosmetic Substances 0.000 abstract description 6
- 238000005187 foaming Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 239000012459 cleaning agent Substances 0.000 abstract description 3
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 abstract description 3
- 230000007794 irritation Effects 0.000 abstract description 2
- 238000011086 high cleaning Methods 0.000 abstract 1
- 238000011156 evaluation Methods 0.000 description 11
- 239000006260 foam Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 235000011044 succinic acid Nutrition 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002307 Dextran Polymers 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- 229960005137 succinic acid Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 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 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- OLZDNUXWSVTBBV-UHFFFAOYSA-M sodium;4-dodec-1-enoxy-4-oxobutanoate Chemical compound [Na+].CCCCCCCCCCC=COC(=O)CCC([O-])=O OLZDNUXWSVTBBV-UHFFFAOYSA-M 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical group CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- XACKAZKMZQZZDT-MDZDMXLPSA-N 2-[(e)-octadec-9-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCC(C(O)=O)CC(O)=O XACKAZKMZQZZDT-MDZDMXLPSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical group CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- AACHVWXCVWWMSI-UHFFFAOYSA-N 3-hydroxypropyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCCO AACHVWXCVWWMSI-UHFFFAOYSA-N 0.000 description 1
- VFKZECOCJCGZQK-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCO VFKZECOCJCGZQK-UHFFFAOYSA-M 0.000 description 1
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- YPOGAMDNDKPXIL-UHFFFAOYSA-M C(CCC(=O)[O-])(=O)OC=CCCCCCC.[K+] Chemical compound C(CCC(=O)[O-])(=O)OC=CCCCCCC.[K+] YPOGAMDNDKPXIL-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 1
- 240000000912 Macadamia tetraphylla Species 0.000 description 1
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000745768 Pluchea carolinensis Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 230000003700 hair damage Effects 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004482 other powder Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000013441 quality evaluation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KMPHTYSTEHXSTL-UHFFFAOYSA-M sodium;2-hydroxypropanoate;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O.CC(O)C([O-])=O KMPHTYSTEHXSTL-UHFFFAOYSA-M 0.000 description 1
- XDLYMKFUPYZCMA-UHFFFAOYSA-M sodium;4-oct-1-enoxy-4-oxobutanoate Chemical compound [Na+].CCCCCCC=COC(=O)CCC([O-])=O XDLYMKFUPYZCMA-UHFFFAOYSA-M 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000647 trehalose group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/221—Mono, di- or trisaccharides or derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Description
一般式(I):
トレハロース(株式会社 林原生物化学研究所:登録商標「トレハ」)300gを水350gに溶解し、オクテニルコハク酸無水物180gを添加し、40℃で攪枠しながら水酸化ナトリウムの20%水溶液でpHを7.5〜8.0に調整し8時間反応した後、オクテニルコハク酸トレハロースエステル塩組成物1を得た。この組成物1はオクテニルコハク酸トレハロースナトリウム塩が30.5質量%、オクテニルコハク酸ナトリウムが8.0質量%、トレハロースが11.4質量%、水が50.1質量%であった。
トレハロース(株式会社 林原生物化学研究所:登録商標「トレハ」)300gを水350gに溶解し、オクテニルコハク酸無水物240gを添加し、40℃で攪枠しながらトリエタノールアミンでpHを7.5〜8.0に調整し8時間反応した。反応後、固形分が50%になるように水で調整しオクテニルコハク酸トレハロースエステル塩組成物2を得た。この組成物2はオクテニルコハク酸トレハローストリエタノールアミン塩34.7質量%、オクテニルコハク酸トリエタノールアミンが11.7質量%、トレハロースが3.6質量%、水が50.0質量%であった。
トレハロース(株式会社 林原生物化学研究所:登録商標「トレハ」)300gを水350gに溶解し、オクテニルコハク酸無水物210gを添加し、40℃で攪枠しながら水酸化カリウムの20%水溶液でpHを7.5〜8.0に調整し8時間反応した後、オクテニルコハク酸トレハロースエステル塩組成物3を得た。この組成物3はオクテニルコハク酸トレハロースカリウム塩が34.1質量%、オクテニルコハク酸カリウムが9.3質量%、トレハロースが7.6質量%、水が49質量%からなっている。
トレハロース(株式会社 林原生物化学研究所:登録商標「トレハ」)300gを水350gに溶解し、ドデセニルコハク酸無水物150gを添加し、40℃で攪枠しながら水酸化ナトリウムの20%水溶液でpHを8.0〜8.5に調整し8時間反応した後、固形分が50%になるように水で調整しドデセニルコハク酸トレハロースエステル塩組成物4を得た。この組成物4はドデセニルコハク酸トレハロースナトリウム塩、ドデセニルコハク酸ナトリウム、トレハロース、水からなっている。
トレハロース(株式会社 林原生物化学研究所:登録商標「トレハ」)300gを水350gに溶解し、オクタデセニルコハク酸無水物200gを添加し、50℃で攪枠しながらトリエタノールアミンでpHを8.0〜8.5に調整し8時間反応した。反応後、固形分が50%になるように水で調整しオクタデセニルコハク酸トレハロースエステル塩組成物5を得た。この組成物5はオクタデセニルコハク酸トレハローストリエタノールアミン塩、オクタデセニルコハク酸トリエタノールアミン、トレハロース、水からなっている。
製造例および製造比較例で製造したオクテニルコハク酸トレハロースエステル塩組成物およびアルケニルコハク酸トレハロースエステル塩組成物をガラス瓶に詰め、50℃で一ヶ月保存し変化を観察した。観察項目は色(組成物の420nmおよび700nmの吸収の差)、臭い(官能試験)について製造直後と50℃一ヶ月保存後で調べた。結果を表1に示した。なお官能試験については、5人のパネラーによって臭いの強さを官能的に評価し、以下のように4段階に評価した。
+++:油の酸化臭が非常に強い。
++:油の酸化臭が強い。
+:油の酸化臭がやや強い。
±:油の酸化臭がないが、他の臭い(糖の甘い香り)がある
−:臭いがほとんどない。
表2および表3に示す処方例に従って洗顔フォームを作成し、肌荒れの強いパネラー5名に、試料を通常使用するのと同じように使用してもらい、官能評価で判定した。評価項目については、使用感、肌のつや、保水性で評価した。評価基準は使用感、肌のつや、保水性を効果の高い順に5〜1点で採点してもらい、5名の平均点を求めた。
A:3項目すべてが4点以上
B:3項目のうち2つが4点以上
C:3項目のうち1つが4点以上、あるいは3項目全てが2点以上
4点未満
X:3項目すべてが2点未満
表4および表5に示す処方例に従ってボディシャンプーを作成し、肌荒れの強いパネラー5名に、試料を通常使用するのと同じように使用してもらい、官能評価で判定した。評価項目、評価基準は洗顔フォームと同様に行った。
表6および表7に示す処方例に従ってクレンジングウォッシュを作成し、パネラー5名に、試料を通常使用するのと同じように使用してもらい、官能評価で判定した。評価項目、評価基準は洗顔フォームに準じて行った。
Claims (4)
- オクテニルコハク酸トレハロースエステル塩組成物を含有する、洗髪用途以外の用途に用いる洗浄剤組成物。
- さらに、カチオン化ポリマー;およびアニオン界面活性剤、両性界面活性剤、非イオン界面活性剤およびカチオン界面活性剤よりなる群から選択される1種以上の界面活性剤を含有することを特徴とする請求項1記載の洗浄剤組成物。
- 該オクテニルコハク酸トレハロースエステル塩組成物が、オクテニルコハク酸トレハロースエステル塩、オクテニルコハク酸塩、トレハロースおよび水を含むことを特徴とする請求項1記載の洗浄剤組成物。
- 該オクテニルコハク酸トレハロースエステル塩組成物が、水酸化ナトリウム、水酸化カリウムおよびトリエタノールアミンよりなる群から選択されるアルカリ性物質の存在下、pH7.5〜8.0にて、トレハロースとオクテニルコハク酸無水物とを反応させることによって得られることを特徴とする請求項1記載の洗浄剤組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009515191A JP5427033B2 (ja) | 2007-05-15 | 2008-05-15 | オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007128731 | 2007-05-15 | ||
JP2007128731 | 2007-05-15 | ||
PCT/JP2008/058956 WO2008143136A1 (ja) | 2007-05-15 | 2008-05-15 | オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 |
JP2009515191A JP5427033B2 (ja) | 2007-05-15 | 2008-05-15 | オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2008143136A1 true JPWO2008143136A1 (ja) | 2010-08-05 |
JP5427033B2 JP5427033B2 (ja) | 2014-02-26 |
Family
ID=40031842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009515191A Active JP5427033B2 (ja) | 2007-05-15 | 2008-05-15 | オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP5427033B2 (ja) |
WO (1) | WO2008143136A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114106062B (zh) * | 2021-12-03 | 2023-04-28 | 山东福洋生物科技股份有限公司 | 一种海藻糖基乳化剂的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3107850B2 (ja) * | 1991-02-27 | 2000-11-13 | 日澱化學株式会社 | 化粧品基材 |
JP3352722B2 (ja) * | 1992-08-26 | 2002-12-03 | 日澱化學株式会社 | 糖類のアルケニルコハク酸エステルを含有する化粧料 |
EP0828809A4 (en) * | 1995-05-27 | 1998-12-30 | Procter & Gamble | BODY CARE |
GB9510838D0 (en) * | 1995-05-27 | 1995-07-19 | Procter & Gamble | Cleansing compositions |
JPH10279449A (ja) * | 1997-04-07 | 1998-10-20 | Nichiden Kagaku Kk | アルケニルコハク酸トレハロースエステル塩を含有する組成物およびそれを用いた洗髪剤組成物 |
JPH10287897A (ja) * | 1997-04-11 | 1998-10-27 | Nichiden Kagaku Kk | 洗浄剤組成物およびそれを含有する化粧料 |
JP3545372B2 (ja) * | 2001-09-04 | 2004-07-21 | カネボウ株式会社 | 皮膚洗浄剤組成物 |
JP4019268B2 (ja) * | 2002-12-26 | 2007-12-12 | サンスター株式会社 | 洗浄剤組成物 |
JP2004203801A (ja) * | 2002-12-26 | 2004-07-22 | Sunstar Inc | 洗浄剤組成物 |
-
2008
- 2008-05-15 JP JP2009515191A patent/JP5427033B2/ja active Active
- 2008-05-15 WO PCT/JP2008/058956 patent/WO2008143136A1/ja active Application Filing
Also Published As
Publication number | Publication date |
---|---|
WO2008143136A1 (ja) | 2008-11-27 |
JP5427033B2 (ja) | 2014-02-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2656697C (en) | Alkyl lactyllactates and processes of making the same | |
JP3922299B2 (ja) | 増粘組成物 | |
JP7084165B2 (ja) | 洗浄剤組成物 | |
KR102410538B1 (ko) | 비-석유화학적으로 유도되는 양이온 유화제, 관련 조성물 및 방법 | |
JP6467414B2 (ja) | 身体用洗浄剤およびそのための界面活性剤ブレンド | |
CA2840145C (en) | Personal care composition for reducing surface friction of hair fibres | |
TW200400052A (en) | Hair cleansing compositions | |
JP2011057647A (ja) | 化粧料 | |
JPH0794674B2 (ja) | 洗浄剤組成物 | |
JP2023008894A (ja) | アミノ酸系界面活性剤を含むクレンジングフォーム化粧料組成物 | |
JP2006298916A (ja) | 毛髪洗浄剤組成物 | |
JP2013163658A (ja) | 皮膚洗浄剤組成物 | |
JP2008094724A (ja) | 皮膚洗浄剤組成物 | |
JP5616609B2 (ja) | 毛髪化粧料 | |
JP2012250994A (ja) | 洗浄剤組成物 | |
JP6603030B2 (ja) | クレンジング組成物 | |
KR20120084724A (ko) | 화장료용 오일 조성물 | |
JP2010180182A (ja) | 洗浄剤組成物 | |
JP2009035520A (ja) | 洗浄剤組成物 | |
JP5427033B2 (ja) | オクテニルコハク酸トレハロースエステル塩組成物を含有する洗浄剤組成物 | |
JP6999288B2 (ja) | 毛髪洗浄剤用組成物 | |
JP6407839B2 (ja) | 化粧料の抗菌方法 | |
JP7326728B2 (ja) | 固形石鹸組成物 | |
JP2005154286A (ja) | 毛髪化粧料 | |
JP2020033278A (ja) | 刺激緩和剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20110927 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130423 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130624 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20131105 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131129 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5427033 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |