JP2009501076A - 乳化剤 - Google Patents
乳化剤 Download PDFInfo
- Publication number
- JP2009501076A JP2009501076A JP2008521339A JP2008521339A JP2009501076A JP 2009501076 A JP2009501076 A JP 2009501076A JP 2008521339 A JP2008521339 A JP 2008521339A JP 2008521339 A JP2008521339 A JP 2008521339A JP 2009501076 A JP2009501076 A JP 2009501076A
- Authority
- JP
- Japan
- Prior art keywords
- starch
- emulsifier
- emulsifier according
- alkyl
- succinated
- 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
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 58
- 229920002472 Starch Polymers 0.000 claims abstract description 100
- 235000019698 starch Nutrition 0.000 claims abstract description 100
- 239000008107 starch Substances 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000006260 foam Substances 0.000 claims abstract description 11
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 235000013305 food Nutrition 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- 239000000839 emulsion Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 230000002209 hydrophobic effect Effects 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- -1 alkenyl succinic anhydride Chemical compound 0.000 claims description 16
- 108010043797 4-alpha-glucanotransferase Proteins 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229920000856 Amylose Polymers 0.000 claims description 11
- 102000051366 Glycosyltransferases Human genes 0.000 claims description 11
- 108700023372 Glycosyltransferases Proteins 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 10
- 102100040894 Amylo-alpha-1,6-glucosidase Human genes 0.000 claims description 8
- 102000003925 1,4-alpha-Glucan Branching Enzyme Human genes 0.000 claims description 7
- 108090000344 1,4-alpha-Glucan Branching Enzyme Proteins 0.000 claims description 7
- 229920000945 Amylopectin Polymers 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 240000003183 Manihot esculenta Species 0.000 claims description 3
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 claims description 3
- 244000061456 Solanum tuberosum Species 0.000 claims description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 230000002862 amidating effect Effects 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 235000021374 legumes Nutrition 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 240000004713 Pisum sativum Species 0.000 claims description 2
- 235000010582 Pisum sativum Nutrition 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 244000098338 Triticum aestivum Species 0.000 claims description 2
- 125000002704 decyl 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])* 0.000 claims description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 125000001400 nonyl 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])[H] 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 abstract description 37
- 108090000790 Enzymes Proteins 0.000 abstract description 37
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- 229940088598 enzyme Drugs 0.000 description 36
- 239000000243 solution Substances 0.000 description 23
- 239000012071 phase Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229920001592 potato starch Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229920002245 Dextrose equivalent Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001165 hydrophobic group Chemical group 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- YZUMRMCHAJVDRT-UHFFFAOYSA-N 2-(hexadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCOCC1CO1 YZUMRMCHAJVDRT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YOWKKGPNCDIFFB-UHFFFAOYSA-N 3-decyloxolane-2,5-dione Chemical compound CCCCCCCCCCC1CC(=O)OC1=O YOWKKGPNCDIFFB-UHFFFAOYSA-N 0.000 description 2
- PMSSUODTFUHXHO-UHFFFAOYSA-N 3-nonyloxolane-2,5-dione Chemical compound CCCCCCCCCC1CC(=O)OC1=O PMSSUODTFUHXHO-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical class CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- LGZMUUBPTDRQQM-UHFFFAOYSA-N 10-Bromo-1-decanol Chemical compound OCCCCCCCCCCBr LGZMUUBPTDRQQM-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-UHFFFAOYSA-N 0.000 description 1
- CWNOEVURTVLUNV-UHFFFAOYSA-N 2-(propoxymethyl)oxirane Chemical compound CCCOCC1CO1 CWNOEVURTVLUNV-UHFFFAOYSA-N 0.000 description 1
- IGDUBEZMULCNAF-UHFFFAOYSA-N 2-[(2-dodecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 IGDUBEZMULCNAF-UHFFFAOYSA-N 0.000 description 1
- BJWUSAVNSDYMNC-UHFFFAOYSA-N 3-oxotetradecanoyl 3-oxotetradecanoate Chemical compound CCCCCCCCCCCC(=O)CC(=O)OC(=O)CC(=O)CCCCCCCCCCC BJWUSAVNSDYMNC-UHFFFAOYSA-N 0.000 description 1
- BUKIFWZDTSHEEO-UHFFFAOYSA-N CC(C)CCCCCCCCCCCCC(NC(C(C)O)Cl)=O Chemical class CC(C)CCCCCCCCCCCCC(NC(C(C)O)Cl)=O BUKIFWZDTSHEEO-UHFFFAOYSA-N 0.000 description 1
- GDRMZVPUMQQHPZ-UHFFFAOYSA-N CCCCCCCCCC.C(C1CO1)OCCCC Chemical compound CCCCCCCCCC.C(C1CO1)OCCCC GDRMZVPUMQQHPZ-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000193385 Geobacillus stearothermophilus Species 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 1
- 102100022624 Glucoamylase Human genes 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
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CKMNPXWFAZLBNK-QOFYEYOWSA-N OC[C@H]1O[C@@H]2O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]1[C@H](O)[C@H]2O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O Chemical class OC[C@H]1O[C@@H]2O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]1[C@H](O)[C@H]2O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O CKMNPXWFAZLBNK-QOFYEYOWSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 241001148570 Rhodothermus marinus Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 241000204666 Thermotoga maritima Species 0.000 description 1
- 241000589499 Thermus thermophilus Species 0.000 description 1
- WJRFQBPIMGRYOY-UHFFFAOYSA-N acetyl decanoate Chemical compound CCCCCCCCCC(=O)OC(C)=O WJRFQBPIMGRYOY-UHFFFAOYSA-N 0.000 description 1
- ADCQBLMDYBHFGK-UHFFFAOYSA-N acetyl octanoate Chemical compound CCCCCCCC(=O)OC(C)=O ADCQBLMDYBHFGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 108010019077 beta-Amylase Proteins 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- XSXBDHLZDMGJGA-UHFFFAOYSA-N dimethyl-(oxiran-2-ylmethyl)-tetradecanoylazanium Chemical class CCCCCCCCCCCCCC(=O)[N+](C)(C)CC1CO1 XSXBDHLZDMGJGA-UHFFFAOYSA-N 0.000 description 1
- RGSUZYPDANFDCI-UHFFFAOYSA-N dimethyl-octadecyl-(oxiran-2-ylmethyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1CO1 RGSUZYPDANFDCI-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JJNQYHPVRMBMBC-UHFFFAOYSA-N dodecyl-dimethyl-(oxiran-2-ylmethyl)azanium Chemical class CCCCCCCCCCCC[N+](C)(C)CC1CO1 JJNQYHPVRMBMBC-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- XYGITPUCOKWCFN-UHFFFAOYSA-N hexadecyl-dimethyl-(oxiran-2-ylmethyl)azanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)CC1CO1 XYGITPUCOKWCFN-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- TUFJPPAQOXUHRI-KTKRTIGZSA-N n'-[(z)-octadec-9-enyl]propane-1,3-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCN TUFJPPAQOXUHRI-KTKRTIGZSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008256 whipped cream Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/212—Starch; Modified starch; Starch derivatives, e.g. esters or ethers
- A23L29/219—Chemically modified starch; Reaction or complexation products of starch with other chemicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/732—Starch; Amylose; Amylopectin; 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/02—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/02—Esters
- C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01014—Sucrose-phosphate synthase (2.4.1.14)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01018—1,4-Alpha-glucan branching enzyme (2.4.1.18), i.e. glucan branching enzyme
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01025—4-Alpha-glucanotransferase (2.4.1.25)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/14—Carboxylic acids; Derivatives thereof
- D21H17/15—Polycarboxylic acids, e.g. maleic acid
- D21H17/16—Addition products thereof with hydrocarbons
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/17—Ketenes, e.g. ketene dimers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Cosmetics (AREA)
- General Preparation And Processing Of Foods (AREA)
- Polymerisation Methods In General (AREA)
- Paper (AREA)
Abstract
Description
欧州特許出願第0913406号明細書において、グルコアミラーゼの使用が提案されている。この酵素を用いることによって、乳化剤ではなくカプセル化剤が得られる程度まで好適に澱粉が分解されることが述べられている。本発明によれば、このような分解は望ましくない。
疎水性基をエーテル結合を介して澱粉に結合させるときには、疎水性試薬は、好ましくはハロゲン化物、ハロヒドリン、エポキシドまたはグリシジル基を反応性部位として含む。この薬剤のアルキル鎖は4〜24個の炭素原子、好ましくは7〜20個の炭素原子の間で変化することができる。エーテル結合を提供するための適当な疎水性試薬の例は、臭化セチル、臭化ラウリル、ブチレンオキシド、エポキシド化大豆脂肪アルコール、エポキシド化アマニ脂肪アルコール、アリルグリシジルエーテル、プロピルグリシジルエーテル、ブチルグリシジルエーテル、デカングリシジルエーテル、ラウリルグリシジルエーテル、ラウリルフェニルグリシジルエーテル、ミリストイルグリシジルエーテル、セチルグリシジルエーテル、パルミチルグリシジルエーテル、ステアリルグリシジルエーテル、リノリルグリシジルエーテルおよびそれらの混合物である。本発明により澱粉と反応させる目的で用いることができる他のエーテル化剤は、少なくとも4個の炭素原子を含むハロゲン化アルキル、例えば、1-ブロモデカン、10-ブロモ-1-デカノール、および1-ブロモドデカンである。
実施例1: オクテニルコハク酸化(succinilated)し更に分岐した澱粉の調製
水中5モルの通常のジャガイモ澱粉 (20%乾燥分)を、160℃の温度で噴射加熱(jet cook)した。250 g澱粉(乾燥物質)に相当する溶液の量を、5リットルの二重壁付ガラス反応装置に移し、温度を65℃に設定した。pHを6.5に調整し、澱粉1g当たり200 Uの酵素(Rhodothermus Marinus分岐酵素, 供給業者: TNO Food - Groningen)を加えた。一定の混合を加えながら、反応を65℃で48時間進行させた。
水中10モルの通常のジャガイモ澱粉を含む懸濁液(20%乾燥分)を、160℃の温度で噴射加熱した。次いで、溶液中の乾燥物質の量を、質量および溶液の濃度(ブリックス%)を測定することによって計算した。溶液を10リットルの二重壁付ガラス反応装置に移し、温度を70℃に設定した。pHを6.2に調整し、澱粉1g当たり2 Uの酵素(アミロマルターゼ, 供給業者: TNO Food - Groningen)を加えた。一定の混合を加えながら、反応を70℃で24時間進行させた。次に、溶液を160℃の温度で噴射加熱することによって酵素を失活させた。再度、溶液中の乾燥物質の量を、質量と溶液の濃度(ブリックス%)を測定することによって計算した。
アミロース含量が36重量%であるジャガイモ澱粉15モルを含む39%(W/W)澱粉懸濁液を水道水で調製し、4.4重量% NaOH水溶液を加えて懸濁液のpHを8.5に設定した。温度を20℃に設定し、オクテニルコハク酸無水物をDsmaxが0.02となる量で溶液に徐々に加えた。反応中に、pHは4.4% NaOH (W/V)を用いて8.5に保持した。4時間の反応後、混合物をpH 6.2まで中和し、ブッフナー漏斗を用いて15リットルの水道水で洗浄した。生成物を36% (W/W)懸濁液として8バールおよび6 rpm (4ロール, スリット幅 0.3 mm)でドラム乾燥し、粉砕した (Peppink, 250 μm篩)。
生成物を実施例1- 3に記載の方法で調製した。澱粉6 gをヒマワリ油10 mlに懸濁させ、0.02%アジ化ナトリウム溶液190 mlを加えた。プレエマルションを、Silverstonホモジナイザーを1分間最高速度で用いて調製した。これらのエマルションを、表1のスキームに準じて微小流動化装置(micro-fluidiser)を用いて調製した。結果を、表2にまとめた。
実施例1〜3に記載の生成物40 gと脱イオン水(demi water) 160 gとを、泡立て器を用いてHobartミキサーで最高速度にて2〜3分間泡立てた。混合時間は2〜3分間の間で変化し、生成物の泡の発達状態によって変化する。
Claims (21)
- 澱粉を、疎水性試薬を用いてエーテル化、エステル化またはアミド化し、グリコシルトランスフェラーゼ(E.C.2.4)を用いて酵素変換することによって得られる、疎水性澱粉を含んでなる乳化剤であって、前記疎水性試薬が、7〜24個の炭素原子を有するアルキルまたはアルケニル鎖を含んでなる、乳化剤。
- 前記疎水性澱粉が、アルキルまたはアルケニルスクシネート化澱粉である、請求項1に記載の乳化剤。
- 前記アルキルまたはアルケニルスクシネート化澱粉が、オクテニルスクシネート化、ノニルスクシネート化、デシルスクシネート化、またはドデセニルスクシネート化澱粉である、請求項2に記載の乳化剤。
- 澱粉がオクテニルスクシネート化澱粉である、請求項3に記載の乳化剤。
- 前記アルキルまたはアルケニルスクシネート化澱粉の置換度(DS)が、0.005〜0.5であり、好ましくは0.01〜0.1である、先行するいずれかの請求項に記載の乳化剤。
- 前記グリコシルトランスフェラーゼが、4-α-グルカノトランスフェラーゼ(E.C.2.4.1.25)である、先行するいずれかの請求項に記載の乳化剤。
- 前記グリコシルトランスフェラーゼが、シクロマルトデキストリングルカノトランスフェラーゼ (E.C.2.4.1.19)である、請求項1〜5のいずれか一項に記載の乳化剤。
- 前記グリコシルトランスフェラーゼが、1,4-α-グルカン分岐酵素 (E.C.2.4.1.18)である、請求項1〜5のいずれか一項に記載の乳化剤。
- 前記澱粉が、ジャガイモ、キャッサバ、小麦、大麦、トウモロコシ、コメ、エンドウ、またはマメ澱粉である、先行するいずれかの請求項に記載の乳化剤。
- 前記澱粉のアミロース含量が、前記澱粉の乾燥重量に対して20-〜70重量%であり、好ましくは 30〜50重量%である、請求項9に記載の乳化剤。
- 前記澱粉のアミロペクチン含量が、前記澱粉の乾燥重量に対して80重量%を上回り、好ましくは95重量%を上回る、請求項9に記載の乳化剤。
- 澱粉を、7〜24個の炭素原子を有するアルキル鎖を含む疎水性試薬を用いてエーテル化、エステル化またはアミド化し、グリコシルトランスフェラーゼ(E.C.2.4)を用いて酵素変換することを含んでなる、先行するいずれかの請求項に記載の乳化剤の製造方法。
- 澱粉を、7〜24個の炭素原子を有するアルキルまたはアルケニル基を含んでなる疎水性試薬を用いてエステル化する、請求項12に記載の方法。
- 澱粉を、最初にグリコシルトランスフェラーゼ(E.C.2.4)を用いて酵素変換した後、アルキルまたはアルケニルコハク酸無水物を用いてエステル化する、請求項12または13に記載の方法。
- 澱粉を、最初にアルキルまたはアルケニルコハク酸無水物を用いてエステル化した後、グリコシルトランスフェラーゼ(E.C.2.4)による酵素変換を行う、請求項12または13に記載の方法。
- 請求項1〜11のいずれか一項に記載の乳化剤が乳化剤として含まれている、エマルションを含んでなるかまたは該エマルションの形態である、食品または化粧品。
- エマルションを安定化させるための、請求項1〜11のいずれか一項に記載の乳化剤の使用。
- 弾性ゲル化フォームの製造のための、請求項1〜11のいずれか一項に記載の乳化剤の使用。
- アルケニルコハク酸無水物(ASA)および/またはアルケニルケテン二量体(AKD)エマルションを安定化させるための、請求項1〜11のいずれか一項に記載の乳化剤の使用。
- ビニルモノマーの乳化重合における、請求項1〜11のいずれか一項に記載の乳化剤の使用。
- 請求項1〜11のいずれか一項に記載の乳化剤を含んでなる、フォーム。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05076605.4 | 2005-07-12 | ||
EP05076605.4A EP1743693B1 (en) | 2005-07-12 | 2005-07-12 | Emulsifier |
PCT/NL2006/000347 WO2007008066A1 (en) | 2005-07-12 | 2006-07-10 | Emulsifier |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009501076A true JP2009501076A (ja) | 2009-01-15 |
JP5936802B2 JP5936802B2 (ja) | 2016-06-22 |
Family
ID=35431247
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008521339A Expired - Fee Related JP5936802B2 (ja) | 2005-07-12 | 2006-07-10 | 乳化剤、乳化剤の製造方法、食品または化粧品、乳化剤の使用、またはフォーム |
Country Status (10)
Country | Link |
---|---|
US (1) | US8178323B2 (ja) |
EP (1) | EP1743693B1 (ja) |
JP (1) | JP5936802B2 (ja) |
CN (1) | CN101222973B (ja) |
AU (1) | AU2006267170B8 (ja) |
BR (1) | BRPI0613448B1 (ja) |
CA (1) | CA2615120C (ja) |
ES (1) | ES2625898T3 (ja) |
MX (1) | MX2008000444A (ja) |
WO (1) | WO2007008066A1 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011529696A (ja) * | 2008-08-05 | 2011-12-15 | ディーエスエム アイピー アセッツ ビー.ブイ. | 新しいデンプン組成物およびベークド製品を製造する方法 |
JP2014505673A (ja) * | 2010-12-15 | 2014-03-06 | スペキシモ アクティエボラーグ | 粒子に安定化された新規のエマルション及び泡 |
JP2015517815A (ja) * | 2012-05-30 | 2015-06-25 | ジボダン エス エー | 組成物 |
JP2017519637A (ja) * | 2015-05-06 | 2017-07-20 | スンシル ユニバーシティー リサーチ コンソーシアム テクノ−パーク | 多様な範囲の疎水性を持つヒドロコロイドの製造方法 |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10080373B2 (en) * | 2006-12-13 | 2018-09-25 | Coöperatie Avebe U.A. | Cream substitute |
FR2923832B1 (fr) * | 2007-11-20 | 2011-01-07 | Roquette Freres | Composition anionique aqueuse contenant au moins un amidon anionique gelatinise, soluble et, de preference, un amidon anionique insoluble, non gelatinise ou partiellement gonfle. |
CN101319053B (zh) * | 2008-07-08 | 2010-08-25 | 江南大学 | 一种脂肪酸多孔淀粉酯的制备方法与应用 |
EP2172489A1 (en) * | 2008-09-15 | 2010-04-07 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Method for altering starch using a microbial branching enzyme |
EP2199462A1 (en) * | 2008-12-18 | 2010-06-23 | Coöperatie Avebe U.A. | A process for making paper |
EP2419078B1 (en) * | 2009-04-15 | 2017-11-01 | Akzo Nobel Chemicals International B.V. | Deposition of hydrophobic active ingredeints from surfactant systems |
US8258250B2 (en) * | 2009-10-07 | 2012-09-04 | Johnson & Johnson Consumer Companies, Inc. | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
US8399590B2 (en) | 2009-10-07 | 2013-03-19 | Akzo Nobel Chemicals International B.V. | Superhydrophilic amphiphilic copolymers and processes for making the same |
US20110081310A1 (en) * | 2009-10-07 | 2011-04-07 | Fevola Michael J | Compositions comprising superhydrophilic amphiphilic copolymers and methods of use thereof |
ES2745987T3 (es) * | 2009-10-07 | 2020-03-04 | Johnson & Johnson Consumer Inc | Composiciones que comprenden copolímeros anfifílicos superhidrófilos y métodos de uso de los mismos |
BR112012007486B1 (pt) * | 2009-10-07 | 2022-08-02 | Akzo Nobel Chemicals International B.V. | Co-polímero anfifílico super-hidrofílico e processo para fazer um co-polímero anfifílico super-hidrofílico |
US11173106B2 (en) | 2009-10-07 | 2021-11-16 | Johnson & Johnson Consumer Inc. | Compositions comprising a superhydrophilic amphiphilic copolymer and a micellar thickener |
CN101716476B (zh) * | 2009-11-13 | 2012-08-08 | 华南理工大学 | 一种淀粉烷基苷表面活性剂的制备方法 |
WO2011062999A2 (en) * | 2009-11-17 | 2011-05-26 | Purdue Research Foundation | Dendritic emulsifiers and methods for their use and preparation |
US20110124746A1 (en) | 2009-11-25 | 2011-05-26 | National Starch & Chemical Company | Alkenyl succinic acid anhydride half ester emulsifier |
KR20120137361A (ko) * | 2010-02-09 | 2012-12-20 | 인테벡, 인코포레이티드 | 태양 전지 제조용의 조정가능한 섀도우 마스크 어셈블리 |
CN101891830B (zh) * | 2010-07-06 | 2012-05-30 | 华南理工大学 | 一种淀粉基高分子表面活性剂及其制备方法 |
JP6131558B2 (ja) * | 2012-06-21 | 2017-05-24 | 不二製油株式会社 | マメ科種子多糖類コハク酸誘導体エステル及びその製造方法 |
WO2015091652A1 (en) * | 2013-12-20 | 2015-06-25 | Akzo Nobel Chemicals International B.V. | Hair fixatives including cellulose ether based polyglucose polymers |
US11135148B2 (en) * | 2013-12-20 | 2021-10-05 | Nouryon Chemicals International B.V. | Hair fixatives including starch ester based polyglucose polymers |
CA2947948C (en) * | 2014-05-08 | 2021-09-14 | Cooperatie Avebe U.A. | Chewy candy comprising a highly branched starch (hbs) and method for providing the same |
US10400105B2 (en) | 2015-06-19 | 2019-09-03 | The Research Foundation For The State University Of New York | Extruded starch-lignin foams |
KR101849928B1 (ko) | 2015-11-25 | 2018-04-18 | 서울대학교 산학협력단 | 유중 수적형 에멀젼을 이용한 나노-마이크로 전분 젤 입자 제조 방법 |
CN110885403B (zh) * | 2018-09-11 | 2022-08-30 | 上海东升新材料有限公司 | 一种改性淀粉乳化剂及采用该乳化剂制备的akd乳液 |
WO2020080947A1 (en) | 2018-10-18 | 2020-04-23 | Coöperatie Avebe U.A. | Milk substitute |
CN113402623B (zh) * | 2021-04-20 | 2022-03-29 | 佛山市南海华昊华丰淀粉有限公司 | 一种大分子淀粉基乳化剂及其制备方法与应用 |
CN117229428B (zh) * | 2023-11-10 | 2024-01-16 | 广东海天创新技术有限公司 | 辛烯基琥珀酸淀粉及其制备方法和应用 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3565887A (en) * | 1968-05-15 | 1971-02-23 | Corn Products Co | Unsaturated and long chain esters of cyclodextrin |
JPH0255702A (ja) * | 1988-08-18 | 1990-02-26 | Natl Starch & Chem Corp | 保存安定性を有する化工でんぷん乳化剤 |
JPH0481403A (ja) * | 1990-07-25 | 1992-03-16 | Kao Corp | 新規シクロデキストリン誘導体及びその製造方法 |
JPH09169802A (ja) * | 1995-11-13 | 1997-06-30 | L'oreal Sa | シクロデキストリンから誘導された新規化合物 |
JPH10262560A (ja) * | 1997-03-28 | 1998-10-06 | Kao Corp | 乳化組成物及びその製造法 |
JPH1146780A (ja) * | 1997-05-13 | 1999-02-23 | Ezaki Glico Co Ltd | 耐熱性アミロマルターゼ |
JPH11236338A (ja) * | 1997-10-31 | 1999-08-31 | Natl Starch & Chem Investment Holding Corp | 封入剤としての酵素転化澱粉誘導体の使用 |
JP2002534566A (ja) * | 1999-01-15 | 2002-10-15 | コーオペラティーベ、ベルコープ‐アン、プロドゥクティーベレニギング、バン、アルダペルメール、アン、デリバーテン、アベベ、ベー.アー. | 疎水性デンプン誘導体 |
JP2002539822A (ja) * | 1999-03-29 | 2002-11-26 | ノボザイムス アクティーゼルスカブ | 分枝酵素活性を有するポリペプチド及びそれをコードする核酸 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238064A (en) * | 1963-10-09 | 1966-03-01 | Staley Mfg Co A E | Method for purifying amylose |
US4035235A (en) * | 1973-03-12 | 1977-07-12 | Anheuser-Busch, Incorporated | Method of making lipophilic starch derivatives |
HU194939B (en) * | 1983-12-22 | 1988-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing alpha- beta- and gamma cyclodextrine of high yield capacity |
US4663159A (en) | 1985-02-01 | 1987-05-05 | Union Carbide Corporation | Hydrophobe substituted, water-soluble cationic polysaccharides |
WO1989001043A1 (en) | 1987-07-28 | 1989-02-09 | Genetics Institute, Inc. | Process and enzyme for preparing cyclodextrins, especially alpha-cyclodextrin |
US4977252A (en) * | 1988-03-11 | 1990-12-11 | National Starch And Chemical Investment Holding Corporation | Modified starch emulsifier characterized by shelf stability |
NL8902128A (nl) | 1989-08-23 | 1991-03-18 | Avebe Coop Verkoop Prod | Vertakkingsenzym en gebruik daarvan. |
JPH06505149A (ja) | 1991-01-31 | 1994-06-16 | ノボ ノルディスク アクティーゼルスカブ | グルコシドのグルコシル化のための酵素処理 |
JPH08508538A (ja) | 1993-04-15 | 1996-09-10 | アクゾ ノーベル ナムローゼ フェンノートシャップ | アミド変性されたカルボキシル含有多糖類を作る方法およびそのようにして得られる脂肪族アミド変性した多糖類 |
US5482704A (en) | 1994-06-28 | 1996-01-09 | National Starch And Chemical Investment Holding Corporation | Cosmetic compositions containing amino-multicarboxylate modified starch |
NL9401090A (nl) | 1994-06-29 | 1996-02-01 | Avebe Coop Verkoop Prod | Werkwijze voor het oppervlaktelijmen of strijken van papier. |
DE4428654A1 (de) * | 1994-08-12 | 1996-02-15 | Consortium Elektrochem Ind | Wasserlösliche Cyclodextrinderivate mit lipophilen Substituenten und Verfahren zu ihrer Herstellung |
DE19610995C2 (de) | 1996-03-21 | 2002-12-19 | Betzdearborn Inc | Papierleimungsmittel und -verfahren |
US6054302A (en) * | 1996-05-06 | 2000-04-25 | National Starch And Chemical Investment Holding Corporation | High solids, single phase process for preparing enzyme-converted starches |
NL1004214C2 (nl) | 1996-10-07 | 1998-04-10 | Avebe Coop Verkoop Prod | Toepassing van gemodificeerd zetmeel als middel voor het vormen van een thermoreversibele gel. |
US5776476A (en) | 1997-02-28 | 1998-07-07 | National Starch And Chemical Investment Holding Corporation | Cosmetic compositions containing hydrophobic starch derivatives |
AU745133B2 (en) * | 1997-10-31 | 2002-03-14 | Corn Products Development, Inc. | Glucoamylase converted starch derivatives and their use as emulsifying and encapsulating agents |
US5935826A (en) * | 1997-10-31 | 1999-08-10 | National Starch And Chemical Investment Holding Corporation | Glucoamylase converted starch derivatives and their use as emulsifying and encapsulating agents |
EP1214441A1 (en) * | 1999-09-01 | 2002-06-19 | Novozymes A/S | Maltogenic amylase-modified starch derivatives |
DE59907971D1 (de) | 1999-10-19 | 2004-01-15 | Suedzucker Ag | Emulsionspolymerisationsverfahren |
DE10008930A1 (de) * | 2000-02-25 | 2001-08-30 | Basf Ag | Antiknitterausrüstung von cellulosehaltigen Textilien und Wäschenachbehandlungsmittel |
CA2344121A1 (en) | 2000-04-28 | 2001-10-28 | Takaaki Otera | Substantially sediment-free beverage emulsion stabilizer |
NL1018426C2 (nl) * | 2001-06-29 | 2003-01-07 | Tno | Preventie van retrogradatie van zetmeel. |
JP4081403B2 (ja) | 2002-09-24 | 2008-04-23 | 株式会社コーセー | O/w/o型乳化化粧料 |
-
2005
- 2005-07-12 ES ES05076605.4T patent/ES2625898T3/es active Active
- 2005-07-12 EP EP05076605.4A patent/EP1743693B1/en active Active
-
2006
- 2006-07-10 US US11/995,131 patent/US8178323B2/en not_active Expired - Fee Related
- 2006-07-10 AU AU2006267170A patent/AU2006267170B8/en not_active Ceased
- 2006-07-10 JP JP2008521339A patent/JP5936802B2/ja not_active Expired - Fee Related
- 2006-07-10 MX MX2008000444A patent/MX2008000444A/es active IP Right Grant
- 2006-07-10 BR BRPI0613448-3A patent/BRPI0613448B1/pt not_active IP Right Cessation
- 2006-07-10 WO PCT/NL2006/000347 patent/WO2007008066A1/en active Application Filing
- 2006-07-10 CN CN2006800254815A patent/CN101222973B/zh not_active Expired - Fee Related
- 2006-07-10 CA CA2615120A patent/CA2615120C/en not_active Expired - Fee Related
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3565887A (en) * | 1968-05-15 | 1971-02-23 | Corn Products Co | Unsaturated and long chain esters of cyclodextrin |
JPH0255702A (ja) * | 1988-08-18 | 1990-02-26 | Natl Starch & Chem Corp | 保存安定性を有する化工でんぷん乳化剤 |
JPH0481403A (ja) * | 1990-07-25 | 1992-03-16 | Kao Corp | 新規シクロデキストリン誘導体及びその製造方法 |
JPH09169802A (ja) * | 1995-11-13 | 1997-06-30 | L'oreal Sa | シクロデキストリンから誘導された新規化合物 |
JPH10262560A (ja) * | 1997-03-28 | 1998-10-06 | Kao Corp | 乳化組成物及びその製造法 |
JPH1146780A (ja) * | 1997-05-13 | 1999-02-23 | Ezaki Glico Co Ltd | 耐熱性アミロマルターゼ |
JPH11236338A (ja) * | 1997-10-31 | 1999-08-31 | Natl Starch & Chem Investment Holding Corp | 封入剤としての酵素転化澱粉誘導体の使用 |
JP2002534566A (ja) * | 1999-01-15 | 2002-10-15 | コーオペラティーベ、ベルコープ‐アン、プロドゥクティーベレニギング、バン、アルダペルメール、アン、デリバーテン、アベベ、ベー.アー. | 疎水性デンプン誘導体 |
JP2002539822A (ja) * | 1999-03-29 | 2002-11-26 | ノボザイムス アクティーゼルスカブ | 分枝酵素活性を有するポリペプチド及びそれをコードする核酸 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011529696A (ja) * | 2008-08-05 | 2011-12-15 | ディーエスエム アイピー アセッツ ビー.ブイ. | 新しいデンプン組成物およびベークド製品を製造する方法 |
JP2014505673A (ja) * | 2010-12-15 | 2014-03-06 | スペキシモ アクティエボラーグ | 粒子に安定化された新規のエマルション及び泡 |
JP2015517815A (ja) * | 2012-05-30 | 2015-06-25 | ジボダン エス エー | 組成物 |
JP2017519637A (ja) * | 2015-05-06 | 2017-07-20 | スンシル ユニバーシティー リサーチ コンソーシアム テクノ−パーク | 多様な範囲の疎水性を持つヒドロコロイドの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20100029928A1 (en) | 2010-02-04 |
EP1743693B1 (en) | 2017-03-29 |
MX2008000444A (es) | 2008-03-10 |
US8178323B2 (en) | 2012-05-15 |
BRPI0613448B1 (pt) | 2017-07-04 |
CN101222973A (zh) | 2008-07-16 |
EP1743693A1 (en) | 2007-01-17 |
CA2615120A1 (en) | 2007-01-18 |
AU2006267170B8 (en) | 2010-09-23 |
JP5936802B2 (ja) | 2016-06-22 |
ES2625898T3 (es) | 2017-07-20 |
AU2006267170A1 (en) | 2007-01-18 |
WO2007008066A1 (en) | 2007-01-18 |
AU2006267170B2 (en) | 2010-07-29 |
CA2615120C (en) | 2013-12-31 |
CN101222973B (zh) | 2013-03-27 |
BRPI0613448A2 (pt) | 2012-11-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5936802B2 (ja) | 乳化剤、乳化剤の製造方法、食品または化粧品、乳化剤の使用、またはフォーム | |
ES2208268T3 (es) | Derivados de almidon hidrofobos. | |
EP1584370B1 (en) | Emulsifier | |
Bhosale et al. | Process optimization for the synthesis of octenyl succinyl derivative of waxy corn and amaranth starches | |
JP5912012B2 (ja) | 無水アルケニルコハク酸ハーフエステル乳化剤 | |
KR920010521B1 (ko) | 저장안정성의 개질전분유화제 및 그 제조방법 | |
EP2247204B1 (en) | Preparation of enzymatically hydrolysed starch | |
JP3943335B2 (ja) | アグロバクテリウム・ラジオバクターによって産生されるヘテロ多糖類 | |
JP2004510065A (ja) | 選択したカチオン性デンプン材料を含有するデンプン組成物の製紙における使用または製紙以外の使用 | |
MXPA01007101A (es) | Derivados de almidon hidrofobico | |
WO2023192471A1 (en) | Octenylsuccinylated waxy tapioca starches, emulsions including them and methods for making same | |
KR20220080105A (ko) | 홈 케어 및 퍼스널 케어를 위한 변성 전분 | |
MXPA01004362A (en) | Substantially sediment-free beverage emulsion stabilizer |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090525 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120629 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120928 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20121005 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20121029 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20121105 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20121129 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20121206 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130104 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20131029 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140227 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20140228 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140324 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140509 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140806 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140813 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140909 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20141205 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150618 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150717 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150820 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150918 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160127 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160225 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160511 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5936802 Country of ref document: JP 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 |
|
LAPS | Cancellation because of no payment of annual fees |