AU2013370663B2 - 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
- AU2013370663B2 AU2013370663B2 AU2013370663A AU2013370663A AU2013370663B2 AU 2013370663 B2 AU2013370663 B2 AU 2013370663B2 AU 2013370663 A AU2013370663 A AU 2013370663A AU 2013370663 A AU2013370663 A AU 2013370663A AU 2013370663 B2 AU2013370663 B2 AU 2013370663B2
- Authority
- AU
- Australia
- 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.)
- Ceased
Links
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 title claims abstract description 374
- 150000002148 esters Chemical class 0.000 title description 71
- 238000002360 preparation method Methods 0.000 title description 41
- 238000000034 method Methods 0.000 claims abstract description 79
- -1 ester compounds Chemical class 0.000 claims abstract description 71
- 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 203
- 238000006243 chemical reaction Methods 0.000 claims description 144
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 60
- 150000008065 acid anhydrides Chemical class 0.000 claims description 54
- 150000007524 organic acids Chemical class 0.000 claims description 53
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 51
- 125000002252 acyl group Chemical group 0.000 claims description 44
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 44
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 40
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 37
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 33
- 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 23
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 claims description 22
- 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 22
- 235000019260 propionic acid Nutrition 0.000 claims description 21
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims description 19
- 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 17
- 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 63
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 48
- 239000007787 solid Substances 0.000 description 37
- 230000008569 process Effects 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 229920001503 Glucan Polymers 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000002253 acid 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
- 229920000642 polymer Polymers 0.000 description 14
- 238000001542 size-exclusion chromatography Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 12
- 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
- 230000007935 neutral effect Effects 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
- 239000003054 catalyst Substances 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
- 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
- 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
- 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
- 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
- 238000002834 transmittance Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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
- 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
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- 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
- 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
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- 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
- 238000006386 neutralization reaction Methods 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
- 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
- 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
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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)
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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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| AU2013370663A1 AU2013370663A1 (en) | 2015-06-18 |
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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 |
| EP3609949A1 (en) | 2017-06-30 | 2020-02-19 | DuPont Industrial Biosciences USA, LLC | Polysaccharide-elastomer masterbatch compositions |
| 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 |
| 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 |
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| US7000000B1 (en) * | 1999-01-25 | 2006-02-14 | E. I. Du Pont De Nemours And Company | Polysaccharide fibers |
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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 |
| 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 |
-
2013
- 2013-12-20 JP JP2015550693A patent/JP6261610B2/ja active Active
- 2013-12-20 CA CA2895132A patent/CA2895132A1/en not_active Abandoned
- 2013-12-20 WO PCT/US2013/076905 patent/WO2014105696A1/en not_active Ceased
- 2013-12-20 AU AU2013370663A patent/AU2013370663B2/en not_active Ceased
- 2013-12-20 ES ES13821334T patent/ES2736042T3/es active Active
- 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
- 2013-12-20 SG SG11201504218XA patent/SG11201504218XA/en unknown
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- 2013-12-20 MY MYPI2015701718A patent/MY170135A/en unknown
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2014
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2015
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2016
- 2016-03-02 US US15/058,406 patent/US10000580B2/en active Active
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| US7000000B1 (en) * | 1999-01-25 | 2006-02-14 | E. I. Du Pont De Nemours And Company | Polysaccharide fibers |
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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 |
| KR20150100702A (ko) | 2015-09-02 |
| 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 |
| EP2938639B1 (en) | 2019-05-01 |
| PH12015501541B1 (en) | 2015-10-05 |
| WO2014105698A1 (en) | 2014-07-03 |
| MX2015008463A (es) | 2015-09-23 |
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