JP2579843B2 - 澱粉エステルの製造方法、澱粉エステル、及び澱粉エステル組成物 - Google Patents
澱粉エステルの製造方法、澱粉エステル、及び澱粉エステル組成物Info
- Publication number
- JP2579843B2 JP2579843B2 JP7142029A JP14202995A JP2579843B2 JP 2579843 B2 JP2579843 B2 JP 2579843B2 JP 7142029 A JP7142029 A JP 7142029A JP 14202995 A JP14202995 A JP 14202995A JP 2579843 B2 JP2579843 B2 JP 2579843B2
- Authority
- JP
- Japan
- Prior art keywords
- starch
- ester
- starch ester
- vinyl
- organic solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920002472 Starch Polymers 0.000 title claims abstract description 149
- 235000019698 starch Nutrition 0.000 title claims abstract description 148
- 239000008107 starch Substances 0.000 title claims abstract description 147
- 150000002148 esters Chemical class 0.000 title claims abstract description 113
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 41
- 238000005886 esterification reaction Methods 0.000 claims abstract description 30
- 230000032050 esterification Effects 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 239000011356 non-aqueous organic solvent Substances 0.000 claims abstract description 16
- 238000006467 substitution reaction Methods 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 31
- 239000004014 plasticizer Substances 0.000 claims description 25
- -1 amino compound Chemical class 0.000 claims description 23
- 239000003153 chemical reaction reagent Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004185 ester group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229920002301 cellulose acetate Polymers 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000012766 organic filler Substances 0.000 claims description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 4
- 229920000229 biodegradable polyester Polymers 0.000 claims description 3
- 239000004622 biodegradable polyester Substances 0.000 claims description 3
- 150000004679 hydroxides Chemical group 0.000 claims description 3
- 239000011229 interlayer Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- 239000004952 Polyamide Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229920001290 polyvinyl ester Polymers 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 3
- 238000000465 moulding Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 15
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 12
- 229920002261 Corn starch Polymers 0.000 description 10
- 239000008120 corn starch Substances 0.000 description 10
- 229940099112 cornstarch Drugs 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229920000856 Amylose Polymers 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 229960002622 triacetin Drugs 0.000 description 8
- 239000001087 glyceryl triacetate Substances 0.000 description 7
- 235000013773 glyceryl triacetate Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 229920000881 Modified starch Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 235000019426 modified starch Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 3
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 3
- 239000010445 mica Substances 0.000 description 3
- 229910052618 mica group Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 3
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004368 Modified starch Substances 0.000 description 2
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
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- 238000013329 compounding Methods 0.000 description 2
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- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 2
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 2
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 201000003373 familial cold autoinflammatory syndrome 3 Diseases 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000005015 poly(hydroxybutyrate) Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 description 2
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- INJOMKTZOLKMBF-UHFFFAOYSA-N Guanfacine Chemical compound NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl INJOMKTZOLKMBF-UHFFFAOYSA-N 0.000 description 1
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- 238000001746 injection moulding Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000021254 resistant starch Nutrition 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000004628 starch-based polymer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940065385 tenex Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/04—Starch derivatives, e.g. crosslinked derivatives
- C08L3/06—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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F281/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having carbon-to-carbon triple bonds as defined in group C08F38/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7142029A JP2579843B2 (ja) | 1994-11-08 | 1995-06-08 | 澱粉エステルの製造方法、澱粉エステル、及び澱粉エステル組成物 |
| CA002204723A CA2204723C (en) | 1994-11-08 | 1995-10-30 | Method for producing starch esters, starch esters, and starch ester compositions |
| DK95935586T DK0791604T3 (da) | 1994-11-08 | 1995-10-30 | Fremgangsmåde til fremstilling af stivelsesester, stivelsesester og stivelsesestersammensætning |
| DE69522339T DE69522339T2 (de) | 1994-11-08 | 1995-10-30 | Verfahren zur herstellung eines ester von stärke, stärkeester und zusammensetzung die die stärkeester enthalten |
| PCT/JP1995/002218 WO1996014342A1 (en) | 1994-11-08 | 1995-10-30 | Process for producing starch ester, starch ester, and starch ester composition |
| EP95935586A EP0791604B1 (en) | 1994-11-08 | 1995-10-30 | Process for producing starch ester, starch ester, and starch ester composition |
| KR1019970703050A KR100394410B1 (ko) | 1994-11-08 | 1995-10-30 | 전분에스테르의제조방법,전분에스테르,및전분에스테르조성물 |
| US08/591,591 US5714601A (en) | 1994-11-08 | 1995-10-30 | Method for producing starch esters, starch esters, and starch ester compositions |
| AU37545/95A AU692625B2 (en) | 1994-11-08 | 1995-10-30 | Process for producing starch ester, starch ester, and starch ester composition |
| AT95935586T ATE204584T1 (de) | 1994-11-08 | 1995-10-30 | Verfahren zur herstellung eines ester von stärke, stärkeester und zusammensetzung die die stärkeester enthalten |
| FI971912A FI114986B (fi) | 1994-11-08 | 1997-05-05 | Menetelmä tärkkelysestereiden valmistamiseksi, tärkkelysesterit ja tärkkelysesterikoostumukset |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6-273679 | 1994-11-08 | ||
| JP27367994 | 1994-11-08 | ||
| JP7142029A JP2579843B2 (ja) | 1994-11-08 | 1995-06-08 | 澱粉エステルの製造方法、澱粉エステル、及び澱粉エステル組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08188601A JPH08188601A (ja) | 1996-07-23 |
| JP2579843B2 true JP2579843B2 (ja) | 1997-02-12 |
Family
ID=26474169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7142029A Expired - Fee Related JP2579843B2 (ja) | 1994-11-08 | 1995-06-08 | 澱粉エステルの製造方法、澱粉エステル、及び澱粉エステル組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5714601A (enExample) |
| EP (1) | EP0791604B1 (enExample) |
| JP (1) | JP2579843B2 (enExample) |
| KR (1) | KR100394410B1 (enExample) |
| AT (1) | ATE204584T1 (enExample) |
| AU (1) | AU692625B2 (enExample) |
| DE (1) | DE69522339T2 (enExample) |
| DK (1) | DK0791604T3 (enExample) |
| FI (1) | FI114986B (enExample) |
| WO (1) | WO1996014342A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11203648B2 (en) * | 2016-09-30 | 2021-12-21 | Japan Corn Starch Co., Ltd. | Esterified starch and starch-containing plastic composition |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10101465A (ja) * | 1996-09-25 | 1998-04-21 | Seto Seido Kk | 徐放性肥料 |
| JPH1094592A (ja) * | 1996-09-25 | 1998-04-14 | Nippon Koonsutaac Kk | 固形状芳香品 |
| FI107386B (fi) * | 1996-12-31 | 2001-07-31 | Valtion Teknillinen | Menetelmä tärkkelysesterien valmistamiseksi |
| JP2939586B1 (ja) * | 1998-11-25 | 1999-08-25 | 日本コーンスターチ株式会社 | 澱粉エステル |
| EP1035135B1 (de) * | 1999-03-05 | 2004-10-13 | Wolff Walsrode AG | Regioselektiv substituierte Ester von Oligo- und Polysacchariden und Verfahren zu ihrer Herstellung |
| JP4601111B2 (ja) * | 2000-01-02 | 2010-12-22 | 日本コーンスターチ株式会社 | 生分解性のモデルの製作方法 |
| US6833097B2 (en) * | 2000-01-03 | 2004-12-21 | Japan Corn Starch Co. Ltd. | Biodegradable block for models |
| FR2816310A1 (fr) * | 2000-11-06 | 2002-05-10 | Universit De Bretagne Sud | Procede d'obtention de nouveaux esters d'amidon et leurs applications |
| US7358828B2 (en) * | 2003-03-24 | 2008-04-15 | Advantest Corporation | Orthogonal modulation device, method, program, recording medium, and modulation device |
| JP5160040B2 (ja) * | 2005-02-28 | 2013-03-13 | 千葉製粉株式会社 | 糖脂肪酸エステルの製造方法 |
| JP5275042B2 (ja) * | 2006-01-06 | 2013-08-28 | コムストック、ボブ | ビニル脂肪酸エステルからの糖エステルの生成 |
| WO2008053820A1 (en) * | 2006-10-30 | 2008-05-08 | Japan Vam & Poval Co., Ltd. | Method for esterifying cellulose resin, modified cellulose resin obtained by the esterification method, and method for producing the modified cellulose resin |
| WO2010080612A1 (en) * | 2008-12-18 | 2010-07-15 | Wm. Wrigley Jr. Company | Chewing gum and gum bases containing highly substituted starch short chain carboxylates |
| FR2951177B1 (fr) * | 2009-10-09 | 2012-12-21 | Roquette Freres | Procede de preparation de derives acetyles de matiere amylacee |
| CN102702369B (zh) * | 2012-05-08 | 2014-04-02 | 华南理工大学 | 一种辛烯基琥珀酸淀粉酯的制备方法 |
| CN102649051A (zh) * | 2012-05-15 | 2012-08-29 | 西南科技大学 | 一种淀粉酯吸附材料的制备方法 |
| US9527928B2 (en) * | 2012-05-15 | 2016-12-27 | Archer-Daniels-Midland-Company | Anhydrous corn processing |
| ITTO20130570A1 (it) | 2013-07-08 | 2015-01-09 | Fond Istituto Italiano Di Tecnologia | Procedimento per la produzione di un bioelastomero composito, idrofobico, comprendente amido |
| CN103992518B (zh) * | 2014-04-30 | 2017-02-08 | 天津市天塑科技集团有限公司包装材料分公司 | 一种可生物降解的包装材料 |
| US20190264006A1 (en) * | 2015-12-22 | 2019-08-29 | Rhodia Acetow Gmbh | New plasticized compositions comprising cellulose acetate |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928828A (en) * | 1957-07-22 | 1960-03-15 | Staley Mfg Co A E | Acylation of hydroxy compounds with vinyl esters |
| US3022289A (en) * | 1959-02-13 | 1962-02-20 | Staley Mfg Co A E | Acylation of starch |
| US3318868A (en) * | 1965-06-21 | 1967-05-09 | Nat Starch Chem Corp | Process for the continuous acylation of amylose |
| US3795670A (en) * | 1973-03-05 | 1974-03-05 | Us Agriculture | Process for making starch triacetates |
| US4891404A (en) * | 1988-05-27 | 1990-01-02 | Purdue Research Foundation | Biodegradable graft copolymers |
| HUT66717A (en) * | 1991-03-19 | 1994-12-28 | Parke Davis & Co | Biodegradable compositions comprising starch derivatives, methods of making the compositions, and articles made from said composition |
| DE4114185C1 (enExample) * | 1991-04-30 | 1993-02-04 | Battelle-Institut E.V., 6000 Frankfurt, De | |
| CA2117885A1 (en) * | 1992-03-31 | 1993-10-14 | Gerd Borchers | Esterified starch composition |
| ATE176265T1 (de) * | 1992-10-07 | 1999-02-15 | Nat Starch Chem Invest | Mischungen aus stärkeestern und linearen polyestern |
| US5462983A (en) * | 1993-07-27 | 1995-10-31 | Evercorn, Inc. | Biodegradable moldable products and films comprising blends of starch esters and polyesters |
-
1995
- 1995-06-08 JP JP7142029A patent/JP2579843B2/ja not_active Expired - Fee Related
- 1995-10-30 AT AT95935586T patent/ATE204584T1/de active
- 1995-10-30 US US08/591,591 patent/US5714601A/en not_active Expired - Lifetime
- 1995-10-30 EP EP95935586A patent/EP0791604B1/en not_active Expired - Lifetime
- 1995-10-30 AU AU37545/95A patent/AU692625B2/en not_active Ceased
- 1995-10-30 KR KR1019970703050A patent/KR100394410B1/ko not_active Expired - Fee Related
- 1995-10-30 WO PCT/JP1995/002218 patent/WO1996014342A1/ja not_active Ceased
- 1995-10-30 DE DE69522339T patent/DE69522339T2/de not_active Expired - Lifetime
- 1995-10-30 DK DK95935586T patent/DK0791604T3/da active
-
1997
- 1997-05-05 FI FI971912A patent/FI114986B/fi not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11203648B2 (en) * | 2016-09-30 | 2021-12-21 | Japan Corn Starch Co., Ltd. | Esterified starch and starch-containing plastic composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0791604A4 (enExample) | 1997-08-27 |
| US5714601A (en) | 1998-02-03 |
| FI114986B (fi) | 2005-02-15 |
| EP0791604B1 (en) | 2001-08-22 |
| ATE204584T1 (de) | 2001-09-15 |
| DE69522339D1 (de) | 2001-09-27 |
| WO1996014342A1 (en) | 1996-05-17 |
| KR100394410B1 (ko) | 2003-11-14 |
| AU3754595A (en) | 1996-05-31 |
| FI971912A0 (fi) | 1997-05-05 |
| FI971912L (fi) | 1997-06-24 |
| DE69522339T2 (de) | 2002-05-29 |
| KR970707164A (ko) | 1997-12-01 |
| AU692625B2 (en) | 1998-06-11 |
| DK0791604T3 (da) | 2001-10-29 |
| EP0791604A1 (en) | 1997-08-27 |
| JPH08188601A (ja) | 1996-07-23 |
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