CA2895132A1 - Preparation of poly alpha-1,3-glucan esters and films therefrom - Google Patents
Preparation of poly alpha-1,3-glucan esters and films therefrom Download PDFInfo
- Publication number
- CA2895132A1 CA2895132A1 CA2895132A CA2895132A CA2895132A1 CA 2895132 A1 CA2895132 A1 CA 2895132A1 CA 2895132 A CA2895132 A CA 2895132A CA 2895132 A CA2895132 A CA 2895132A CA 2895132 A1 CA2895132 A1 CA 2895132A1
- Authority
- CA
- Canada
- Prior art keywords
- glucan
- poly alpha
- acid
- anhydride
- 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.)
- Abandoned
Links
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 title claims abstract description 388
- 238000002360 preparation method Methods 0.000 title claims description 43
- 150000002148 esters Chemical class 0.000 title description 71
- 238000000034 method Methods 0.000 claims abstract description 79
- -1 ester compounds Chemical class 0.000 claims abstract description 75
- 238000006467 substitution reaction Methods 0.000 claims abstract description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 215
- 238000006243 chemical reaction Methods 0.000 claims description 153
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 61
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 59
- 150000008065 acid anhydrides Chemical class 0.000 claims description 56
- 150000007524 organic acids Chemical class 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 52
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 50
- 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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 42
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 41
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 37
- 239000003377 acid catalyst Substances 0.000 claims description 33
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 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 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
- 235000019260 propionic acid Nutrition 0.000 claims description 22
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims description 20
- 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 18
- 238000001816 cooling Methods 0.000 claims description 17
- 235000005985 organic acids Nutrition 0.000 claims description 10
- 150000007522 mineralic acids Chemical group 0.000 claims description 9
- 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 5
- 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
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 description 65
- 239000007787 solid Substances 0.000 description 37
- 230000008569 process Effects 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- 229920001503 Glucan Polymers 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 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
- 229920000642 polymer Polymers 0.000 description 14
- 238000001542 size-exclusion chromatography Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 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 12
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
- 238000005886 esterification reaction 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 238000003756 stirring Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 238000011282 treatment Methods 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
- 150000004676 glycans Chemical class 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification 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
- 238000005406 washing Methods 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 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
- 229940093915 gynecological organic acid Drugs 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000032050 esterification 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
- 238000005259 measurement Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229930091371 Fructose Natural products 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
- 239000005715 Fructose Substances 0.000 description 4
- 108010055629 Glucosyltransferases Proteins 0.000 description 4
- 102000000340 Glucosyltransferases Human genes 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
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 4
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-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
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000835 fiber 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000001556 precipitation Methods 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
- 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
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- JQZNEWNSFCOFDG-UHFFFAOYSA-N CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O JQZNEWNSFCOFDG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JPFGFRMPGVDDGE-UHFFFAOYSA-N Leucrose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)(CO)OC1 JPFGFRMPGVDDGE-UHFFFAOYSA-N 0.000 description 2
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- 241000194024 Streptococcus salivarius Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
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- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 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
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- 238000010353 genetic engineering Methods 0.000 description 1
- 108090001082 glucan-binding proteins Proteins 0.000 description 1
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical group CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000569 multi-angle light scattering Methods 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
- 238000006386 neutralization reaction 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
- 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
- 238000009877 rendering Methods 0.000 description 1
- 238000000926 separation method Methods 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
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 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 | |
| US201261746338P | 2012-12-27 | 2012-12-27 | |
| US201261746328P | 2012-12-27 | 2012-12-27 | |
| US61/746,335 | 2012-12-27 | ||
| US61/746,338 | 2012-12-27 | ||
| US61/746,328 | 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 |
|---|---|
| CA2895132A1 true CA2895132A1 (en) | 2014-07-03 |
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Family Applications (1)
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|---|---|---|---|
| CA2895132A Abandoned CA2895132A1 (en) | 2012-12-27 | 2013-12-20 | Preparation of poly alpha-1,3-glucan esters and films therefrom |
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| 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) | PH12015501541A1 (https=) |
| SG (2) | SG11201504218XA (https=) |
| WO (2) | WO2014105696A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ708558A (en) * | 2012-12-27 | 2019-10-25 | Du Pont | Preparation of poly alpha-1,3-glucan esters and films therefrom |
| AU2014367230B2 (en) * | 2013-12-20 | 2018-08-16 | Nutrition & Biosciences USA 4, Inc. | Films of poly alpha-1,3-glucan esters and method for their preparation |
| AU2015204026B2 (en) | 2014-01-06 | 2018-08-16 | Nutrition & Biosciences USA 4, Inc. | Production of poly alpha-1,3-glucan films |
| US10106626B2 (en) | 2014-01-17 | 2018-10-23 | Ei Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| AU2015206354A1 (en) * | 2014-01-17 | 2016-07-21 | E. I. Du Pont De Nemours And Company | Production of gelled networks of poly alpha-1,3-glucan formate and films therefrom |
| 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 |
| EP3237454B1 (en) | 2014-12-22 | 2020-08-12 | DuPont Industrial Biosciences USA, LLC | Polymeric blend containing poly alpha-1,3-glucan |
| ES2803024T3 (es) | 2015-02-06 | 2021-01-22 | Dupont Ind Biosciences Usa Llc | Dispersiones coloidales de polímeros basados en poli-alfa-1,3-glucano |
| EP3303411B1 (en) | 2015-06-01 | 2020-11-18 | DuPont Industrial Biosciences USA, LLC | Structured liquid compositions comprising colloidal dispersions of poly alpha-1,3-glucan |
| BR112017028167A2 (pt) | 2015-06-30 | 2018-08-28 | Du Pont | composição e método de produção de composto |
| CN108350660B (zh) * | 2015-10-26 | 2022-04-29 | 营养与生物科学美国4公司 | 水不溶性α-(1，3→葡聚糖)组合物 |
| CA2997563C (en) | 2015-10-26 | 2022-03-22 | E. I. Du Pont De Nemours And Company | Polysaccharide coatings for paper |
| WO2017083228A1 (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 |
| EP3374488B1 (en) | 2015-11-13 | 2020-10-14 | DuPont Industrial Biosciences USA, LLC | Glucan fiber compositions for use in laundry care and fabric care |
| WO2017083229A1 (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 |
| US10895028B2 (en) * | 2015-12-14 | 2021-01-19 | Dupont Industrial Biosciences Usa, Llc | Nonwoven glucan webs |
| KR102486203B1 (ko) | 2016-07-22 | 2023-01-11 | 뉴트리션 앤드 바이오사이언시스 유에스에이 4, 인크. | 다당류를 포함하는 폴리우레탄 중합체 |
| WO2018081263A1 (en) | 2016-10-28 | 2018-05-03 | E. I. Du Pont De Nemours And Company | Rubber compositions comprising polysaccharides |
| CN110198983A (zh) | 2016-11-22 | 2019-09-03 | 纳幕尔杜邦公司 | 制造聚丙烯腈纤维的方法 |
| 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 |
| KR20190082929A (ko) * | 2016-11-22 | 2019-07-10 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리알파-1,3-글루칸 에스테르 및 이로 제조된 물품 |
| CN110198957A (zh) | 2016-11-22 | 2019-09-03 | 纳幕尔杜邦公司 | 多糖的原位官能化和其组合物 |
| PL3628691T3 (pl) | 2016-12-16 | 2021-11-22 | The Procter & Gamble Company | Amfifilowe pochodne polisacharydów i zawierające je kompozycje |
| KR20190135492A (ko) | 2017-04-25 | 2019-12-06 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 산소 차단성을 갖는 다당류 코팅 |
| JP7420561B2 (ja) | 2017-06-30 | 2024-01-23 | 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 | 多糖－エラストマーマスターバッチ組成物 |
| JP7295846B2 (ja) | 2017-09-01 | 2023-06-21 | 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 | 多糖類を含むラテックス組成物 |
| US11098334B2 (en) | 2017-12-14 | 2021-08-24 | Nutrition & Biosciences USA 4, Inc. | Alpha-1,3-glucan graft copolymers |
| WO2019164669A1 (en) * | 2018-02-26 | 2019-08-29 | E. I. Du Pont De Nemours And Company | Blends of polyesters and polysaccharides |
| EP3870616B1 (en) | 2018-10-25 | 2023-10-11 | DuPont Industrial Biosciences USA, LLC | Alpha-1,3-glucan graft copolymers |
| JP2023528442A (ja) * | 2020-06-04 | 2023-07-04 | 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 | デキストラン－α－グルカングラフトコポリマー及びその誘導体 |
| EP4165156B1 (en) | 2020-06-10 | 2025-04-30 | The Procter & Gamble Company | A laundry care or dish care composition comprising a poly alpha-1,6-glucan derivative |
| JP2023528379A (ja) | 2020-06-10 | 2023-07-04 | ザ プロクター アンド ギャンブル カンパニー | ポリアルファ－１，６－グルカン誘導体を含む洗濯ケア又は食器ケア組成物 |
| JP2023526263A (ja) * | 2020-06-10 | 2023-06-21 | ザ プロクター アンド ギャンブル カンパニー | ポリα１，３－グルカンエステルを含む製品 |
| CA3178617A1 (en) | 2020-06-10 | 2021-12-16 | Mark Robert Sivik | A laundry care or dish care composition comprising a poly alpha-1,6-glucan ester |
| US20230287148A1 (en) | 2020-06-10 | 2023-09-14 | Nutrition & Biosciences USA 4, Inc. | Poly alpha-1,6-glucan esters and compositions comprising same |
| EP4284906A1 (en) | 2021-01-29 | 2023-12-06 | Danisco US Inc. | Compositions for cleaning and methods related thereto |
| EP4294848A1 (en) | 2021-02-19 | 2023-12-27 | Nutrition & Biosciences USA 4, Inc. | Oxidized polysaccharide derivatives |
| CN117242102A (zh) | 2021-05-04 | 2023-12-15 | 营养与生物科学美国4公司 | 包含不溶性α-葡聚糖的组合物 |
| 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 |
| US20250032390A1 (en) | 2021-12-16 | 2025-01-30 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising cationic alpha-glucan ethers in aqueous polar organic solvents |
| EP4496834A1 (en) | 2022-03-21 | 2025-01-29 | Nutrition & Biosciences USA 4, Inc. | Compositions comprising insoluble alpha-glucan |
| 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 |
| 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 |
| JP2026503673A (ja) | 2023-02-01 | 2026-01-29 | ザ プロクター アンド ギャンブル カンパニー | 酵素を含有する洗剤組成物 |
| WO2024163584A1 (en) | 2023-02-01 | 2024-08-08 | Danisco Us Inc. | Subtilisin variants and methods of use |
| WO2025072419A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences Usa 1, Llc | Crosslinked alpha-glucan derivatives |
| WO2025072416A1 (en) | 2023-09-29 | 2025-04-03 | Nutrition & Biosciences USA 4, Inc. | Polysaccharide derivatives |
| 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 |
| 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 |
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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 |
| DE60009886T2 (de) * | 1999-01-25 | 2005-03-31 | E.I. Du Pont De Nemours And Co., Wilmington | Polysaccharidfasern |
| 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 |
| 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) |
| NZ708558A (en) * | 2012-12-27 | 2019-10-25 | Du Pont | Preparation of poly alpha-1,3-glucan esters and films therefrom |
| 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 MY MYPI2015701718A patent/MY170135A/en unknown
- 2013-12-20 SG SG11201504218XA patent/SG11201504218XA/en unknown
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- 2013-12-20 US US14/136,168 patent/US20140187766A1/en not_active Abandoned
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2014
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- 2015-07-08 PH PH12015501541A patent/PH12015501541A1/en unknown
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2016
- 2016-03-02 US US15/058,406 patent/US10000580B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20140187766A1 (en) | 2014-07-03 |
| EP2938639A1 (en) | 2015-11-04 |
| KR20150100702A (ko) | 2015-09-02 |
| US10000580B2 (en) | 2018-06-19 |
| BR112015015528A8 (pt) | 2019-10-22 |
| ES2736042T3 (es) | 2019-12-23 |
| WO2014105696A1 (en) | 2014-07-03 |
| JP6261610B2 (ja) | 2018-01-17 |
| SG11201504218XA (en) | 2015-07-30 |
| AU2013370663A1 (en) | 2015-06-18 |
| CN105008401A (zh) | 2015-10-28 |
| US9278988B2 (en) | 2016-03-08 |
| SG11201505127QA (en) | 2015-07-30 |
| US20160251453A1 (en) | 2016-09-01 |
| EP2938639B1 (en) | 2019-05-01 |
| MX370287B (es) | 2019-12-09 |
| JP2016505692A (ja) | 2016-02-25 |
| MY170135A (en) | 2019-07-06 |
| WO2014105698A1 (en) | 2014-07-03 |
| BR112015015528A2 (pt) | 2017-07-11 |
| PH12015501541B1 (en) | 2015-10-05 |
| MX2015008463A (es) | 2015-09-23 |
| NZ708558A (en) | 2019-10-25 |
| AU2013370663B2 (en) | 2017-07-27 |
| PH12015501541A1 (en) | 2015-10-05 |
| US20140187767A1 (en) | 2014-07-03 |
| CL2015001853A1 (es) | 2015-10-30 |
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