CN105008401A - 聚α-1，3-葡聚糖酯和由其所得膜的制备 - Google Patents
聚α-1，3-葡聚糖酯和由其所得膜的制备 Download PDFInfo
- Publication number
- CN105008401A CN105008401A CN201380073853.1A CN201380073853A CN105008401A CN 105008401 A CN105008401 A CN 105008401A CN 201380073853 A CN201380073853 A CN 201380073853A CN 105008401 A CN105008401 A CN 105008401A
- Authority
- CN
- China
- Prior art keywords
- dextran
- poly
- acid
- ester
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 71
- 150000002148 esters Chemical class 0.000 title claims description 39
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 91
- -1 ester compounds Chemical class 0.000 claims abstract description 24
- 238000006467 substitution reaction Methods 0.000 claims abstract description 20
- 229920002307 Dextran Polymers 0.000 claims description 387
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 202
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 144
- 238000006243 chemical reaction Methods 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 65
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 58
- 150000008065 acid anhydrides Chemical class 0.000 claims description 55
- 150000007524 organic acids Chemical class 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 50
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
- 235000019439 ethyl acetate Nutrition 0.000 claims description 48
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 42
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 37
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 36
- 239000003377 acid catalyst Substances 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 28
- 238000001816 cooling Methods 0.000 claims description 24
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 24
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 24
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 claims description 21
- 235000019260 propionic acid Nutrition 0.000 claims description 21
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 21
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 5
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 description 62
- 239000007787 solid Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 22
- 238000005406 washing Methods 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 230000004044 response Effects 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- 239000000523 sample Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 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 14
- 238000010438 heat treatment Methods 0.000 description 14
- 230000010354 integration Effects 0.000 description 14
- 238000001542 size-exclusion chromatography Methods 0.000 description 14
- 230000008569 process Effects 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000008103 glucose Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000032050 esterification Effects 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000003828 vacuum filtration Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000003760 magnetic stirring Methods 0.000 description 8
- 239000003595 mist Substances 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000004676 glycans Chemical class 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 5
- 239000011654 magnesium acetate Substances 0.000 description 5
- 235000011285 magnesium acetate Nutrition 0.000 description 5
- 229940069446 magnesium acetate Drugs 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229930091371 Fructose Natural products 0.000 description 4
- 239000005715 Fructose Substances 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 241000194024 Streptococcus salivarius Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 150000002016 disaccharides Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 210000003746 feather Anatomy 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 244000144992 flock Species 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 3
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229920001503 Glucan Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000002242 deionisation method Methods 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000002402 hexoses Chemical class 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- NMFQPFSIPWZZMR-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropan-2-ol Chemical compound FC(F)C(F)(O)C(F)(F)F NMFQPFSIPWZZMR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002444 Exopolysaccharide Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 101710184309 Probable sucrose-6-phosphate hydrolase Proteins 0.000 description 1
- 108010076504 Protein Sorting Signals Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 102400000472 Sucrase Human genes 0.000 description 1
- 101710112652 Sucrose-6-phosphate hydrolase Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 108090001082 glucan-binding proteins Proteins 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261746335P | 2012-12-27 | 2012-12-27 | |
| US201261746328P | 2012-12-27 | 2012-12-27 | |
| US201261746338P | 2012-12-27 | 2012-12-27 | |
| US61/746335 | 2012-12-27 | ||
| US61/746328 | 2012-12-27 | ||
| US61/746338 | 2012-12-27 | ||
| PCT/US2013/076919 WO2014105698A1 (en) | 2012-12-27 | 2013-12-20 | Preparation of poly alpha-1,3-glucan esters and films therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105008401A true CN105008401A (zh) | 2015-10-28 |
Family
ID=49956448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380073853.1A Pending CN105008401A (zh) | 2012-12-27 | 2013-12-20 | 聚α-1，3-葡聚糖酯和由其所得膜的制备 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9278988B2 (https=) |
| EP (1) | EP2938639B1 (https=) |
| JP (1) | JP6261610B2 (https=) |
| KR (1) | KR20150100702A (https=) |
| CN (1) | CN105008401A (https=) |
| AU (1) | AU2013370663B2 (https=) |
| BR (1) | BR112015015528A8 (https=) |
| CA (1) | CA2895132A1 (https=) |
| CL (1) | CL2015001853A1 (https=) |
| ES (1) | ES2736042T3 (https=) |
| MX (1) | MX370287B (https=) |
| MY (1) | MY170135A (https=) |
| NZ (1) | NZ708558A (https=) |
| PH (1) | PH12015501541B1 (https=) |
| SG (2) | SG11201504218XA (https=) |
| WO (2) | WO2014105696A1 (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105026467A (zh) * | 2013-12-20 | 2015-11-04 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯膜和它们的制备方法 |
| CN110248966A (zh) * | 2016-11-22 | 2019-09-17 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯及由其制成的制品 |
| CN111051444A (zh) * | 2017-09-01 | 2020-04-21 | 杜邦工业生物科学美国有限责任公司 | 包含多糖的胶乳组合物 |
| CN111788266A (zh) * | 2018-02-26 | 2020-10-16 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN115667477A (zh) * | 2020-06-10 | 2023-01-31 | 宝洁公司 | 包含聚α-1,3-葡聚糖酯的产品 |
| CN116589606A (zh) * | 2022-12-01 | 2023-08-15 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2938639B1 (en) * | 2012-12-27 | 2019-05-01 | E. I. du Pont de Nemours and Company | Preparation of poly alpha-1,3-glucan esters |
| CN106103551A (zh) | 2014-01-06 | 2016-11-09 | 纳幕尔杜邦公司 | 聚α‑1,3‑葡聚糖膜的制备 |
| US10106626B2 (en) | 2014-01-17 | 2018-10-23 | Ei Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| CN106062050A (zh) * | 2014-01-17 | 2016-10-26 | 纳幕尔杜邦公司 | 聚α‑1，3‑葡聚糖甲酸酯的胶凝网络的制备以及由其形成的膜 |
| CN107074984A (zh) * | 2014-06-26 | 2017-08-18 | 纳幕尔杜邦公司 | 聚α‑1,3‑葡聚糖酯膜的制备 |
| BR112017013368B1 (pt) | 2014-12-22 | 2021-11-23 | Nutrition & Biosciences USA 4, Inc. | Composição de mistura polimérica |
| US11351104B2 (en) | 2015-02-06 | 2022-06-07 | Nutrition & Biosciences USA 4, Inc. | Colloidal dispersions of poly alpha-1,3-glucan based polymers |
| US10738266B2 (en) | 2015-06-01 | 2020-08-11 | Dupont Industrial Biosciences Usa, Llc | Structured liquid compositions comprising colloidal dispersions of poly alpha-1,3-glucan |
| JP6817972B2 (ja) * | 2015-06-30 | 2021-01-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 環状有機無水物を用いるポリα−１，３−グルカンエステルの調製 |
| ES2937288T3 (es) * | 2015-10-26 | 2023-03-27 | Nutrition & Biosciences Usa 4 Inc | Composición de alfa-(1,3->glucano) insoluble en agua |
| CA2997563C (en) | 2015-10-26 | 2022-03-22 | E. I. Du Pont De Nemours And Company | Polysaccharide coatings for paper |
| JP7045313B2 (ja) | 2015-11-13 | 2022-03-31 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物 |
| WO2017083226A1 (en) | 2015-11-13 | 2017-05-18 | E. I. Du Pont De Nemours And Company | Glucan fiber compositions for use in laundry care and fabric care |
| EP3374401B1 (en) | 2015-11-13 | 2022-04-06 | Nutrition & Biosciences USA 4, Inc. | Glucan fiber compositions for use in laundry care and fabric care |
| US10895028B2 (en) | 2015-12-14 | 2021-01-19 | Dupont Industrial Biosciences Usa, Llc | Nonwoven glucan webs |
| BR112019001171B1 (pt) | 2016-07-22 | 2022-08-16 | Nutrition & Biosciences Usa 4, Inc | Polímero de poliuretano, composição de poliuretano, espuma de poliuretano e substrato fibroso revestido |
| KR102542217B1 (ko) * | 2016-10-28 | 2023-06-12 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 다당류를 포함하는 고무 조성물 |
| EP3545038A1 (en) | 2016-11-22 | 2019-10-02 | E. I. du Pont de Nemours and Company | Process for making polyacrylonitrile fibers |
| EP3545005A1 (en) | 2016-11-22 | 2019-10-02 | E. I. du Pont de Nemours and Company | In situ functionalization of polysaccharides and compositions thereof |
| US20230192905A1 (en) * | 2016-11-22 | 2023-06-22 | E I Du Pont De Nemours And Company | Polyalpha-1,3-glucan esters and articles made therefrom |
| MX2019006868A (es) | 2016-12-16 | 2019-09-23 | Du Pont | Derivados de polisacáridos anfifílicos y composiciones que los comprenden. |
| EP3577142B1 (en) | 2017-04-25 | 2023-11-22 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide coatings with oxygen barrier properties |
| US11608417B2 (en) | 2017-06-30 | 2023-03-21 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide-elastomer masterbatch compositions |
| EP4467599A3 (en) | 2017-12-14 | 2025-04-23 | Nutrition & Biosciences USA 4, Inc. | Alpha-1,3-glucan graft copolymers |
| EP3870616B1 (en) | 2018-10-25 | 2023-10-11 | DuPont Industrial Biosciences USA, LLC | Alpha-1,3-glucan graft copolymers |
| BR112022024705A2 (pt) * | 2020-06-04 | 2023-02-28 | Nutrition & Biosciences Usa 4 Inc | Composição, método para produzir um composto de éter ou éster de copolímero de enxerto, método de floculação e método de absorção |
| EP4165091A1 (en) | 2020-06-10 | 2023-04-19 | Nutrition & Biosciences USA 4, Inc. | Poly alpha-1,6-glucan esters and compositions comprising same |
| ES3033620T3 (en) | 2020-06-10 | 2025-08-06 | Procter & Gamble | A laundry care or dish care composition comprising a poly alpha-1,6-glucan derivative |
| HUE071383T2 (hu) | 2020-06-10 | 2025-08-28 | Procter & Gamble | Poli-alfa-1,6-glükánésztert tartalmazó mosószer vagy mosogatószer |
| PL4165154T3 (pl) | 2020-06-10 | 2024-07-08 | The Procter & Gamble Company | Kompozycja do prania lub pielęgnacji naczyń zawierająca pochodną poli(alfa-1,6-glukanu) |
| EP4284906A1 (en) | 2021-01-29 | 2023-12-06 | Danisco US Inc. | Compositions for cleaning and methods related thereto |
| WO2022178073A1 (en) | 2021-02-19 | 2022-08-25 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives for detergent compositions |
| WO2022235655A1 (en) | 2021-05-04 | 2022-11-10 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising insoluble alpha-glucan |
| US20240307288A1 (en) | 2021-07-13 | 2024-09-19 | Nutrition & Biosciences USA 4, Inc. | Cationic glucan ester derivatives |
| EP4426362A1 (en) | 2021-11-05 | 2024-09-11 | Nutrition & Biosciences USA 4, Inc. | Glucan derivatives for microbial control |
| US20250032390A1 (en) | 2021-12-16 | 2025-01-30 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising cationic alpha-glucan ethers in aqueous polar organic solvents |
| KR20240167661A (ko) | 2022-03-21 | 2024-11-27 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 불용성 알파-글루칸을 포함하는 조성물 |
| JP2025523007A (ja) | 2022-07-11 | 2025-07-17 | ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド | 両親媒性グルカンエステル誘導体 |
| WO2024081773A1 (en) | 2022-10-14 | 2024-04-18 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising water, cationic alpha-1,6-glucan ether and organic solvent |
| WO2024112740A1 (en) | 2022-11-23 | 2024-05-30 | Nutrition & Biosciences USA 4, Inc. | Hygienic treatment of surfaces with compositions comprising hydrophobically modified alpha-glucan derivative |
| WO2024129953A1 (en) | 2022-12-16 | 2024-06-20 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| WO2024163584A1 (en) | 2023-02-01 | 2024-08-08 | Danisco Us Inc. | Subtilisin variants and methods of use |
| EP4410941A1 (en) | 2023-02-01 | 2024-08-07 | The Procter & Gamble Company | Detergent compositions containing enzymes |
| WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
| WO2025072417A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
| WO2025072416A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
| WO2025117349A1 (en) | 2023-11-28 | 2025-06-05 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| WO2025199079A1 (en) | 2024-03-20 | 2025-09-25 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| WO2026024921A1 (en) | 2024-07-25 | 2026-01-29 | The Procter & Gamble Company | Detergent composition comprising a subtilisin variant and methods of use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1283632A (zh) * | 1999-08-05 | 2001-02-14 | 武汉大学 | 灵芝α－(1→3)－D－葡聚糖硫酸酯衍生物及其用途和制备方法 |
| TW504525B (en) * | 1999-01-25 | 2002-10-01 | Du Pont | Polysaccharide fibers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501886A (en) * | 1982-08-09 | 1985-02-26 | E. I. Du Pont De Nemours And Company | Cellulosic fibers from anisotropic solutions |
| CN1133654C (zh) | 1999-08-05 | 2004-01-07 | 武汉大学 | 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法 |
| JP4584146B2 (ja) | 2003-07-09 | 2010-11-17 | 江崎グリコ株式会社 | α−１，４−グルカンおよび／またはその修飾物を含む成型物およびその製造方法 |
| US8642757B2 (en) | 2011-09-09 | 2014-02-04 | E I Du Pont De Nemours And Company | High titer production of highly linear poly (α 1,3 glucan) |
| US9080195B2 (en) | 2011-09-09 | 2015-07-14 | E I Du Pont De Nemours And Company | High titer production of poly (α 1,3 glucan) |
| US9403917B2 (en) * | 2012-12-27 | 2016-08-02 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan esters and films therefrom |
| EP2938639B1 (en) * | 2012-12-27 | 2019-05-01 | E. I. du Pont de Nemours and Company | Preparation of poly alpha-1,3-glucan esters |
-
2013
- 2013-12-20 EP EP13821334.3A patent/EP2938639B1/en active Active
- 2013-12-20 AU AU2013370663A patent/AU2013370663B2/en not_active Ceased
- 2013-12-20 CA CA2895132A patent/CA2895132A1/en not_active Abandoned
- 2013-12-20 MY MYPI2015701718A patent/MY170135A/en unknown
- 2013-12-20 WO PCT/US2013/076905 patent/WO2014105696A1/en not_active Ceased
- 2013-12-20 CN CN201380073853.1A patent/CN105008401A/zh active Pending
- 2013-12-20 MX MX2015008463A patent/MX370287B/es active IP Right Grant
- 2013-12-20 KR KR1020157017106A patent/KR20150100702A/ko not_active Abandoned
- 2013-12-20 US US14/136,226 patent/US9278988B2/en active Active
- 2013-12-20 BR BR112015015528A patent/BR112015015528A8/pt not_active Application Discontinuation
- 2013-12-20 JP JP2015550693A patent/JP6261610B2/ja active Active
- 2013-12-20 WO PCT/US2013/076919 patent/WO2014105698A1/en not_active Ceased
- 2013-12-20 SG SG11201504218XA patent/SG11201504218XA/en unknown
- 2013-12-20 NZ NZ70855813A patent/NZ708558A/en not_active IP Right Cessation
- 2013-12-20 ES ES13821334T patent/ES2736042T3/es active Active
- 2013-12-20 US US14/136,168 patent/US20140187766A1/en not_active Abandoned
-
2014
- 2014-06-26 SG SG11201505127QA patent/SG11201505127QA/en unknown
-
2015
- 2015-06-26 CL CL2015001853A patent/CL2015001853A1/es unknown
- 2015-07-08 PH PH12015501541A patent/PH12015501541B1/en unknown
-
2016
- 2016-03-02 US US15/058,406 patent/US10000580B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW504525B (en) * | 1999-01-25 | 2002-10-01 | Du Pont | Polysaccharide fibers |
| CN1283632A (zh) * | 1999-08-05 | 2001-02-14 | 武汉大学 | 灵芝α－(1→3)－D－葡聚糖硫酸酯衍生物及其用途和制备方法 |
Non-Patent Citations (5)
| Title |
|---|
| G•奥迪安: "《聚合反应原理》", 30 June 1987, 科学出版社 * |
| KOZO OGAWA ET AL.: "X-ray diffraction data for (1→3)-α-d-glucan triacetate", 《CARBOHYDRATE POLYMERS》 * |
| 张惟杰: "《糖复合物生化研究技术 第二版》", 31 October 1994, 浙江大学出版社 * |
| 王孟钟 等: "《胶粘剂应用手册》", 30 November 1987, 化学工业出版社 * |
| 胡玉洁: "《天然高分子材料改性与应用》", 31 July 2003, 北京：化学工业出版社 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105026467A (zh) * | 2013-12-20 | 2015-11-04 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯膜和它们的制备方法 |
| CN110248966A (zh) * | 2016-11-22 | 2019-09-17 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖酯及由其制成的制品 |
| CN110248966B (zh) * | 2016-11-22 | 2023-02-17 | 营养与生物科学美国4公司 | 聚α-1，3-葡聚糖酯及由其制成的制品 |
| CN111051444A (zh) * | 2017-09-01 | 2020-04-21 | 杜邦工业生物科学美国有限责任公司 | 包含多糖的胶乳组合物 |
| CN111788266A (zh) * | 2018-02-26 | 2020-10-16 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN111788266B (zh) * | 2018-02-26 | 2023-08-22 | 杜邦工业生物科学美国有限责任公司 | 聚酯和多糖的共混物 |
| CN115667477A (zh) * | 2020-06-10 | 2023-01-31 | 宝洁公司 | 包含聚α-1,3-葡聚糖酯的产品 |
| CN116589606A (zh) * | 2022-12-01 | 2023-08-15 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
| CN116589606B (zh) * | 2022-12-01 | 2024-05-28 | 中国药科大学 | 一种丁酰化酵母葡聚糖及其制备方法、应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ708558A (en) | 2019-10-25 |
| PH12015501541A1 (en) | 2015-10-05 |
| ES2736042T3 (es) | 2019-12-23 |
| BR112015015528A8 (pt) | 2019-10-22 |
| MY170135A (en) | 2019-07-06 |
| US9278988B2 (en) | 2016-03-08 |
| WO2014105698A1 (en) | 2014-07-03 |
| MX2015008463A (es) | 2015-09-23 |
| EP2938639A1 (en) | 2015-11-04 |
| JP2016505692A (ja) | 2016-02-25 |
| WO2014105696A1 (en) | 2014-07-03 |
| CL2015001853A1 (es) | 2015-10-30 |
| AU2013370663A1 (en) | 2015-06-18 |
| JP6261610B2 (ja) | 2018-01-17 |
| CA2895132A1 (en) | 2014-07-03 |
| KR20150100702A (ko) | 2015-09-02 |
| MX370287B (es) | 2019-12-09 |
| AU2013370663B2 (en) | 2017-07-27 |
| US20160251453A1 (en) | 2016-09-01 |
| US20140187766A1 (en) | 2014-07-03 |
| US10000580B2 (en) | 2018-06-19 |
| EP2938639B1 (en) | 2019-05-01 |
| PH12015501541B1 (en) | 2015-10-05 |
| BR112015015528A2 (pt) | 2017-07-11 |
| US20140187767A1 (en) | 2014-07-03 |
| SG11201504218XA (en) | 2015-07-30 |
| SG11201505127QA (en) | 2015-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105008401A (zh) | 聚α-1，3-葡聚糖酯和由其所得膜的制备 | |
| US9403917B2 (en) | Preparation of poly alpha-1,3-glucan esters and films therefrom | |
| JP6484252B2 (ja) | ポリα−１，３−グルカンエステルの調製及びそれから製造されたフィルム | |
| AU2013363174B2 (en) | Preparation of poly alpha-1,3-glucan ethers | |
| Heinze et al. | 4.2 Chemical characteristics of cellulose acetate | |
| JP6817972B2 (ja) | 環状有機無水物を用いるポリα−１，３−グルカンエステルの調製 | |
| WO2015200596A1 (en) | Preparation of poly alpha-1,3-glucan ester films | |
| WO2015109164A1 (en) | Production of gelled networks of poly alpha-1,3-glucan formate and films therefrom | |
| CN110198957A (zh) | 多糖的原位官能化和其组合物 | |
| Stetco et al. | Supramolecular structure and anomer‐selective formation of polyglucuronic acid | |
| CN121673430A (zh) | 纤维素材料的疏水化改性方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20151028 |