KR20150100702A - 폴리 알파-1,3-글루칸 에스테르의 제조 및 그로부터의 필름 - Google Patents
폴리 알파-1,3-글루칸 에스테르의 제조 및 그로부터의 필름 Download PDFInfo
- Publication number
- KR20150100702A KR20150100702A KR1020157017106A KR20157017106A KR20150100702A KR 20150100702 A KR20150100702 A KR 20150100702A KR 1020157017106 A KR1020157017106 A KR 1020157017106A KR 20157017106 A KR20157017106 A KR 20157017106A KR 20150100702 A KR20150100702 A KR 20150100702A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- glucan
- polyalpha
- anhydride
- alpha
- 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.)
- Abandoned
Links
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 title claims abstract description 195
- 150000002148 esters Chemical class 0.000 title claims description 72
- 238000002360 preparation method Methods 0.000 title description 19
- 229920001503 Glucan Polymers 0.000 claims abstract description 164
- 238000000034 method Methods 0.000 claims abstract description 72
- -1 ester compounds Chemical class 0.000 claims abstract description 70
- 238000006467 substitution reaction Methods 0.000 claims abstract description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 196
- 238000006243 chemical reaction Methods 0.000 claims description 140
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
- 150000008065 acid anhydrides Chemical class 0.000 claims description 72
- 150000007524 organic acids Chemical class 0.000 claims description 53
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 51
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 47
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 47
- 125000002252 acyl group Chemical group 0.000 claims description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 44
- 230000008569 process Effects 0.000 claims description 39
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 34
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 34
- 239000003377 acid catalyst Substances 0.000 claims description 32
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 31
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 235000019260 propionic acid Nutrition 0.000 claims description 23
- 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 23
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 21
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 21
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 17
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 11
- 150000007522 mineralic acids Chemical group 0.000 claims description 10
- 235000005985 organic acids Nutrition 0.000 claims description 9
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 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
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 description 60
- 239000007787 solid Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 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
- 239000000523 sample Substances 0.000 description 14
- 238000001542 size-exclusion chromatography Methods 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 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
- 238000005886 esterification reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 229940093915 gynecological organic acid Drugs 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 7
- 150000004676 glycans Chemical class 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920001282 polysaccharide Polymers 0.000 description 7
- 239000005017 polysaccharide Substances 0.000 description 7
- 230000003595 spectral effect Effects 0.000 description 7
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 7
- 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
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 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 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000010354 integration Effects 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
- 239000005720 sucrose Substances 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
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 102000000340 Glucosyltransferases Human genes 0.000 description 4
- 108010055629 Glucosyltransferases Proteins 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930091371 Fructose Natural products 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 3
- 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 3
- 241000233866 Fungi Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 3
- 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 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229930182478 glucoside Natural products 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
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 3
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
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- 238000010908 decantation Methods 0.000 description 2
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- 239000008367 deionised water Substances 0.000 description 2
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- 150000008131 glucosides Chemical class 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 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
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- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 108090001082 glucan-binding proteins Proteins 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JPFGFRMPGVDDGE-PUVWEJBASA-N leucrose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O)C(O)(CO)OC1 JPFGFRMPGVDDGE-PUVWEJBASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 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
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
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- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- 238000012795 verification Methods 0.000 description 1
Classifications
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- 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)
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| US201261746338P | 2012-12-27 | 2012-12-27 | |
| US201261746335P | 2012-12-27 | 2012-12-27 | |
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| US61/746,335 | 2012-12-27 | ||
| US61/746,338 | 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 |
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| KR20150100702A true KR20150100702A (ko) | 2015-09-02 |
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| JP (1) | JP6261610B2 (enExample) |
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| CN (1) | CN105008401A (enExample) |
| AU (1) | AU2013370663B2 (enExample) |
| BR (1) | BR112015015528A8 (enExample) |
| CA (1) | CA2895132A1 (enExample) |
| CL (1) | CL2015001853A1 (enExample) |
| ES (1) | ES2736042T3 (enExample) |
| MX (1) | MX370287B (enExample) |
| MY (1) | MY170135A (enExample) |
| NZ (1) | NZ708558A (enExample) |
| PH (1) | PH12015501541B1 (enExample) |
| SG (2) | SG11201504218XA (enExample) |
| WO (2) | WO2014105696A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200024837A (ko) * | 2017-06-30 | 2020-03-09 | 듀폰 인더스트리얼 바이오사이언시스 유에스에이, 엘엘씨 | 다당류-엘라스토머 마스터배치 조성물 |
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| JP6261610B2 (ja) * | 2012-12-27 | 2018-01-17 | 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 | ポリα−１，３−グルカンエステルの調製及びそれからのフィルム |
| WO2015094402A1 (en) * | 2013-12-20 | 2015-06-25 | E. I. Du Pont De Nemours And Company | Films of poly alpha-1,3-glucan esters and method for their preparation |
| KR102443837B1 (ko) | 2014-01-06 | 2022-09-19 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 폴리 알파-1,3-글루칸 필름의 제조 |
| 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 |
| WO2015109066A1 (en) * | 2014-01-17 | 2015-07-23 | E. I. Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| WO2015200596A1 (en) * | 2014-06-26 | 2015-12-30 | E. I. Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ester films |
| AU2015369929B2 (en) | 2014-12-22 | 2020-08-20 | Nutrition & Biosciences USA 4, Inc. | Polymeric blend containing poly alpha-1,3-glucan |
| WO2016126685A1 (en) | 2015-02-06 | 2016-08-11 | E. I. Du Pont De Nemours And Company | Colloidal dispersions of poly alpha-1,3-glucan based polymers |
| CN107995923B (zh) | 2015-06-01 | 2021-11-02 | 营养与生物科学美国4公司 | 包含聚α-1,3-葡聚糖的胶体分散体的结构化的液体组合物 |
| US20180155455A1 (en) | 2015-06-30 | 2018-06-07 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan esters using cyclic organic anhydrides |
| KR102746152B1 (ko) | 2015-10-26 | 2024-12-26 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 수불용성 알파-(1,3-글루칸) 조성물 |
| KR102745257B1 (ko) * | 2015-10-26 | 2024-12-23 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 종이용 다당류 코팅 |
| 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 |
| 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 |
| JP2019504932A (ja) | 2015-11-13 | 2019-02-21 | 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 | 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 |
| US10895028B2 (en) * | 2015-12-14 | 2021-01-19 | Dupont Industrial Biosciences Usa, Llc | Nonwoven glucan webs |
| ES2924976T3 (es) | 2016-07-22 | 2022-10-13 | Nutrition & Biosciences Usa 4 Inc | Polímeros de poliuretano que comprenden polisacáridos |
| EP3494173B1 (en) | 2016-10-28 | 2021-06-23 | Nutrition & Biosciences USA 4, Inc. | Rubber compositions comprising polysaccharides |
| 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 |
| EP3545004B1 (en) * | 2016-11-22 | 2023-05-10 | Nutrition & Biosciences USA 4, Inc. | Polyalpha-1,3-glucan esters and articles made therefrom |
| US20190345267A1 (en) | 2016-11-22 | 2019-11-14 | E I Du Pont De Nemours And Company | In situ functionalization of polysaccharides and compositions thereof |
| EP3545038A1 (en) * | 2016-11-22 | 2019-10-02 | E. I. du Pont de Nemours and Company | Process for making polyacrylonitrile fibers |
| MX2019006868A (es) | 2016-12-16 | 2019-09-23 | Du Pont | Derivados de polisacáridos anfifílicos y composiciones que los comprenden. |
| CN110546169A (zh) | 2017-04-25 | 2019-12-06 | 纳幕尔杜邦公司 | 具有氧气阻隔特性的多糖涂料 |
| ES2905837T3 (es) | 2017-09-01 | 2022-04-12 | Nutrition & Biosciences Usa 4 Inc | Composiciones de látex que comprenden polisacáridos |
| US11098334B2 (en) | 2017-12-14 | 2021-08-24 | Nutrition & Biosciences USA 4, Inc. | Alpha-1,3-glucan graft copolymers |
| KR20200128040A (ko) * | 2018-02-26 | 2020-11-11 | 듀폰 인더스트리얼 바이오사이언시스 유에스에이, 엘엘씨 | 폴리에스테르와 다당류의 배합물 |
| 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 |
| HUE071383T2 (hu) | 2020-06-10 | 2025-08-28 | Procter & Gamble | Poli-alfa-1,6-glükánésztert tartalmazó mosószer vagy mosogatószer |
| CN116157421A (zh) | 2020-06-10 | 2023-05-23 | 营养与生物科学美国4公司 | 聚α-1,6-葡聚糖酯和包含其的组合物 |
| ES2992778T3 (en) | 2020-06-10 | 2024-12-18 | Procter & Gamble | A laundry care or dish care composition comprising a poly alpha-1,6-glucan derivative |
| PL4165157T3 (pl) * | 2020-06-10 | 2024-07-15 | The Procter & Gamble Company | Produkt zawierający estry poli(alfa-1,3-glukanu) |
| WO2022165107A1 (en) | 2021-01-29 | 2022-08-04 | Danisco Us Inc | Compositions for cleaning and methods related thereto |
| EP4294849A1 (en) | 2021-02-19 | 2023-12-27 | 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 |
| JP2024525685A (ja) | 2021-07-13 | 2024-07-12 | 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 | カチオン性グルカンエステル誘導体 |
| EP4426362A1 (en) | 2021-11-05 | 2024-09-11 | Nutrition & Biosciences USA 4, Inc. | Glucan derivatives for microbial control |
| CN118382421A (zh) | 2021-12-16 | 2024-07-23 | 营养与生物科学美国4公司 | 包含在水性极性有机溶剂中的阳离子α-葡聚糖醚的组合物 |
| CA3246295A1 (en) | 2022-03-21 | 2023-09-28 | Nutrition & Biosciences Usa 4 Inc | COMPOSITIONS CONTAINING AN INSOLUBLE ALPHA-GLUCANE |
| WO2024015769A1 (en) | 2022-07-11 | 2024-01-18 | Nutrition & Biosciences USA 4, Inc. | Amphiphilic glucan ester derivatives |
| KR20250091210A (ko) | 2022-10-14 | 2025-06-20 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 물, 양이온성 알파-1,6-글루칸 에테르, 및 유기 용매를 포함하는 조성물 |
| 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 |
| 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 |
| WO2024129953A1 (en) | 2022-12-16 | 2024-06-20 | Nutrition & Biosciences USA 4, Inc. | Esterification of alpha-glucan comprising alpha-1,6 glycosidic linkages |
| EP4410941A1 (en) | 2023-02-01 | 2024-08-07 | The Procter & Gamble Company | Detergent compositions containing enzymes |
| CN120677237A (zh) | 2023-02-01 | 2025-09-19 | 丹尼斯科美国公司 | 枯草杆菌蛋白酶变体和使用方法 |
| WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
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| WO2025072417A1 (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 |
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| US4501886A (en) * | 1982-08-09 | 1985-02-26 | E. I. Du Pont De Nemours And Company | Cellulosic fibers from anisotropic solutions |
| AU2509700A (en) * | 1999-01-25 | 2000-08-07 | E.I. Du Pont De Nemours And Company | Polysaccharide fibers |
| 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 |
| CN1133653C (zh) * | 1999-08-05 | 2004-01-07 | 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 |
| 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 |
| 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) |
| 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) |
| JP6261610B2 (ja) * | 2012-12-27 | 2018-01-17 | 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 | ポリα−１，３−グルカンエステルの調製及びそれからのフィルム |
| BR112015015609B1 (pt) * | 2012-12-27 | 2021-04-06 | Nutrition & Biosciences USA 4, Inc. | Filmes e método para a preparação de um filme de éster de poli alfa-1,3-glucano |
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2013
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- 2013-12-20 CA CA2895132A patent/CA2895132A1/en not_active Abandoned
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- 2013-12-20 KR KR1020157017106A patent/KR20150100702A/ko not_active Abandoned
- 2013-12-20 WO PCT/US2013/076919 patent/WO2014105698A1/en not_active Ceased
- 2013-12-20 US US14/136,168 patent/US20140187766A1/en not_active Abandoned
- 2013-12-20 BR BR112015015528A patent/BR112015015528A8/pt not_active Application Discontinuation
- 2013-12-20 MX MX2015008463A patent/MX370287B/es active IP Right Grant
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- 2013-12-20 EP EP13821334.3A patent/EP2938639B1/en active Active
- 2013-12-20 US US14/136,226 patent/US9278988B2/en active Active
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- 2013-12-20 CN CN201380073853.1A patent/CN105008401A/zh active Pending
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2014
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200024837A (ko) * | 2017-06-30 | 2020-03-09 | 듀폰 인더스트리얼 바이오사이언시스 유에스에이, 엘엘씨 | 다당류-엘라스토머 마스터배치 조성물 |
Also Published As
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| CN105008401A (zh) | 2015-10-28 |
| BR112015015528A8 (pt) | 2019-10-22 |
| NZ708558A (en) | 2019-10-25 |
| ES2736042T3 (es) | 2019-12-23 |
| AU2013370663A1 (en) | 2015-06-18 |
| MY170135A (en) | 2019-07-06 |
| CL2015001853A1 (es) | 2015-10-30 |
| CA2895132A1 (en) | 2014-07-03 |
| JP2016505692A (ja) | 2016-02-25 |
| PH12015501541A1 (en) | 2015-10-05 |
| MX370287B (es) | 2019-12-09 |
| US20160251453A1 (en) | 2016-09-01 |
| US20140187767A1 (en) | 2014-07-03 |
| US20140187766A1 (en) | 2014-07-03 |
| WO2014105696A1 (en) | 2014-07-03 |
| EP2938639A1 (en) | 2015-11-04 |
| US9278988B2 (en) | 2016-03-08 |
| JP6261610B2 (ja) | 2018-01-17 |
| BR112015015528A2 (pt) | 2017-07-11 |
| US10000580B2 (en) | 2018-06-19 |
| SG11201505127QA (en) | 2015-07-30 |
| SG11201504218XA (en) | 2015-07-30 |
| AU2013370663B2 (en) | 2017-07-27 |
| EP2938639B1 (en) | 2019-05-01 |
| PH12015501541B1 (en) | 2015-10-05 |
| WO2014105698A1 (en) | 2014-07-03 |
| MX2015008463A (es) | 2015-09-23 |
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