DE2233977A1 - Verfahren zur herstellung oxydierter kohlenhydrate - Google Patents
Verfahren zur herstellung oxydierter kohlenhydrateInfo
- Publication number
- DE2233977A1 DE2233977A1 DE2233977A DE2233977A DE2233977A1 DE 2233977 A1 DE2233977 A1 DE 2233977A1 DE 2233977 A DE2233977 A DE 2233977A DE 2233977 A DE2233977 A DE 2233977A DE 2233977 A1 DE2233977 A1 DE 2233977A1
- Authority
- DE
- Germany
- Prior art keywords
- silver oxide
- silver
- carbohydrate
- oxidized
- starch
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001720 carbohydrates Chemical class 0.000 title claims description 37
- 235000014633 carbohydrates Nutrition 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 68
- 229910001923 silver oxide Inorganic materials 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 230000003647 oxidation Effects 0.000 claims description 32
- 238000007254 oxidation reaction Methods 0.000 claims description 32
- 229920001282 polysaccharide Polymers 0.000 claims description 24
- 239000005017 polysaccharide Substances 0.000 claims description 24
- 150000004804 polysaccharides Chemical class 0.000 claims description 24
- 229910052709 silver Inorganic materials 0.000 claims description 22
- 239000004332 silver Substances 0.000 claims description 22
- 229920002472 Starch Polymers 0.000 claims description 21
- 235000019698 starch Nutrition 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 239000008107 starch Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 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 claims description 13
- 229930006000 Sucrose Natural products 0.000 claims description 13
- -1 alkyl glycoside Chemical class 0.000 claims description 13
- 239000005720 sucrose Substances 0.000 claims description 13
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 11
- 239000001913 cellulose Substances 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 229930182470 glycoside Natural products 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 239000000783 alginic acid Substances 0.000 claims description 3
- 235000010443 alginic acid Nutrition 0.000 claims description 3
- 229920000615 alginic acid Polymers 0.000 claims description 3
- 229960001126 alginic acid Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000003426 co-catalyst Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000001254 oxidized starch Substances 0.000 description 11
- 235000013808 oxidized starch Nutrition 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- 238000005341 cation exchange Methods 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002016 disaccharides Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229940100890 silver compound Drugs 0.000 description 4
- 150000003379 silver compounds Chemical class 0.000 description 4
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 102100038239 Protein Churchill Human genes 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- MQFLXLMNOHHPTC-UHFFFAOYSA-N 1-isothiocyanato-9-(methylsulfinyl)nonane Chemical compound CS(=O)CCCCCCCCCN=C=S MQFLXLMNOHHPTC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/223—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin oxidised
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
- C08B15/04—Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/18—Oxidised starch
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16270671A | 1971-07-14 | 1971-07-14 | |
| US306098A US3873614A (en) | 1971-07-14 | 1972-11-13 | Process for preparing oxidized carbohydrates and products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2233977A1 true DE2233977A1 (de) | 1973-02-01 |
Family
ID=26858995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2233977A Pending DE2233977A1 (de) | 1971-07-14 | 1972-07-11 | Verfahren zur herstellung oxydierter kohlenhydrate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3873614A (enExample) |
| CA (1) | CA959047A (enExample) |
| DE (1) | DE2233977A1 (enExample) |
| FR (1) | FR2145722B1 (enExample) |
| GB (1) | GB1385403A (enExample) |
| NL (1) | NL7209737A (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997020905A1 (de) * | 1995-12-07 | 1997-06-12 | Henkel Kommanditgesellschaft Auf Aktien | Waschmittel mit carbonathaltigem buildersystem und/oder percarbonathaltigem bleichmittel |
| WO1997025399A1 (de) * | 1996-01-03 | 1997-07-17 | Henkel Kommanditgesellschaft Auf Aktien | Waschmittel mit bestimmten oxidierten oligosacchariden |
| WO2003074087A1 (de) * | 2002-03-06 | 2003-09-12 | Biotechnologie - Gesellschaft Mittelhessen Mbh | Kopplung von proteinen an ein modifiziertes polysaccharid |
| US7538092B2 (en) | 2002-10-08 | 2009-05-26 | Fresenius Kabi Deutschland Gmbh | Pharmaceutically active oligosaccharide conjugates |
| US7815893B2 (en) | 2002-09-11 | 2010-10-19 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives |
| US7816516B2 (en) | 2001-03-16 | 2010-10-19 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and an active agent |
| US8017739B2 (en) | 2004-03-11 | 2011-09-13 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
| US8287850B2 (en) | 2004-03-11 | 2012-10-16 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein, prepared by reductive amination |
| US8404834B2 (en) | 2007-12-14 | 2013-03-26 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives and process for their preparation |
| US8466277B2 (en) | 2002-03-06 | 2013-06-18 | Fresenius Kabi Deutschland Gmbh | Coupling low-molecular substances to a modified polysaccharide |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000127A (en) * | 1971-02-25 | 1976-12-28 | Akzo N.V. | Carboxymethylated derivatives of polysaccharide and detergent compositions containing same |
| US4137397A (en) * | 1976-06-01 | 1979-01-30 | Registrar, Jadavpur University | Erythromycin aldobionates |
| JPS5976598A (ja) * | 1982-10-25 | 1984-05-01 | Mitsubishi Gas Chem Co Inc | スケ−ル防止剤 |
| LU85435A1 (fr) * | 1984-06-27 | 1986-01-24 | Amylum Graanderivaten Raff | Procede de preparation d'un carboxymethylamidon,carboxymethylamidon ainsi obtenu et produit de lavage contenant un tel carboxymethylamidon |
| US4916219A (en) * | 1985-03-28 | 1990-04-10 | University Of Iowa Research Foundation | Oligosaccharide heparin fragments as inhibitors of complement cascade |
| FR2597473B1 (fr) * | 1986-01-30 | 1988-08-12 | Roquette Freres | Procede d'oxydation de di-, tri-, oligo- et polysaccharides en acides polyhydroxycarboxyliques, catalyseur mis en oeuvre et produits ainsi obtenus. |
| IT1245063B (it) * | 1991-04-12 | 1994-09-13 | Ferruzzi Ricerca & Tec | Procedimento per l'ossidazione di carboidrati |
| FR2679563B1 (fr) * | 1991-07-22 | 1995-06-09 | Agro Ind Recherc Dev | Alkylgalactosides uronates d'alkyle, leur procede de preparation et leurs applications, notamment comme agents tensio-actifs non ioniques. |
| DE69122402T2 (de) * | 1991-12-23 | 1997-02-06 | Cerestar Holding Bv | Verfahren zur Herstellung von Sauerstoffsäuren aus Kohlenhydraten |
| DE19507668C2 (de) * | 1995-03-04 | 2000-01-27 | Suedzucker Ag | Waschmittelformulierungen, enthaltend eine acylierte Disaccharidcarbonsäure |
| GB9509287D0 (en) * | 1995-05-06 | 1995-06-28 | Solvay Interox Ltd | Detergent builder/activators |
| WO1997002293A1 (fr) * | 1995-06-30 | 1997-01-23 | Lion Corporation | Acide polycarboxylique derive de polysaccharide compose d'unites de glucose anhydre, sels de cet acide, et son procede de preparation |
| US5763381A (en) * | 1995-09-13 | 1998-06-09 | National Starch And Chemical Investment Holding Corporation | Starched-based adjuncts for detergents |
| JP3180131B2 (ja) | 1996-03-28 | 2001-06-25 | ザ、プロクター、エンド、ギャンブル、カンパニー | アルデヒドで官能化されたセルロース性繊維とポリマーから作られた湿潤強度を有する紙製品 |
| US5760212A (en) * | 1996-03-28 | 1998-06-02 | Smith; David Jay | Temporary wet strength additives |
| WO2001034657A1 (en) * | 1999-11-08 | 2001-05-17 | Sca Hygiene Products Zeist B.V. | Process of oxidising primary alcohols |
| RU2165939C1 (ru) * | 2000-03-09 | 2001-04-27 | Медведева Лидия Владимировна | Способ получения модифицированных полисахаридсодержащих продуктов |
| EP1493486B1 (en) * | 2002-04-08 | 2008-02-20 | Sued-Chemie Catalysts Japan, Inc. | Treating agent for exhaust gas containing metal hydride compound and method for treating exhaust gas containing metal hydride compound |
| EP2070951A1 (en) * | 2007-12-14 | 2009-06-17 | Fresenius Kabi Deutschland GmbH | Method for producing a hydroxyalkyl starch derivatives with two linkers |
| CA2763777C (en) | 2009-06-13 | 2017-10-17 | Rennovia Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| BRPI1013087B1 (pt) | 2009-06-13 | 2018-05-15 | Rennovia, Inc. | Processo para preparar um produto de ácido glutárico |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669393B2 (en) * | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3595909A (en) * | 1967-11-01 | 1971-07-27 | Middleboro Chemical Ind Inc | Process for making acid metal salts from organic hydroxyl compounds |
-
1972
- 1972-07-11 DE DE2233977A patent/DE2233977A1/de active Pending
- 1972-07-11 GB GB3232472A patent/GB1385403A/en not_active Expired
- 1972-07-13 NL NL7209737A patent/NL7209737A/xx unknown
- 1972-07-13 CA CA147,009A patent/CA959047A/en not_active Expired
- 1972-07-13 FR FR7225631A patent/FR2145722B1/fr not_active Expired
- 1972-11-13 US US306098A patent/US3873614A/en not_active Expired - Lifetime
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997020905A1 (de) * | 1995-12-07 | 1997-06-12 | Henkel Kommanditgesellschaft Auf Aktien | Waschmittel mit carbonathaltigem buildersystem und/oder percarbonathaltigem bleichmittel |
| WO1997025399A1 (de) * | 1996-01-03 | 1997-07-17 | Henkel Kommanditgesellschaft Auf Aktien | Waschmittel mit bestimmten oxidierten oligosacchariden |
| US7816516B2 (en) | 2001-03-16 | 2010-10-19 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and an active agent |
| US8466277B2 (en) | 2002-03-06 | 2013-06-18 | Fresenius Kabi Deutschland Gmbh | Coupling low-molecular substances to a modified polysaccharide |
| WO2003074087A1 (de) * | 2002-03-06 | 2003-09-12 | Biotechnologie - Gesellschaft Mittelhessen Mbh | Kopplung von proteinen an ein modifiziertes polysaccharid |
| US7541328B2 (en) | 2002-03-06 | 2009-06-02 | Fresenius Kabi Deutschland Gmbh | Coupling proteins to a modified polysaccharide |
| US8916518B2 (en) | 2002-03-06 | 2014-12-23 | Fresenius Kabi Deutschland Gmbh | Coupling proteins to a modified polysaccharide |
| US7815893B2 (en) | 2002-09-11 | 2010-10-19 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives |
| US8618266B2 (en) | 2002-09-11 | 2013-12-31 | Fresenius Kabi Deutschland Gmbh | Hasylated polypeptides |
| US8475765B2 (en) | 2002-09-11 | 2013-07-02 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives |
| US7538092B2 (en) | 2002-10-08 | 2009-05-26 | Fresenius Kabi Deutschland Gmbh | Pharmaceutically active oligosaccharide conjugates |
| US8287850B2 (en) | 2004-03-11 | 2012-10-16 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein, prepared by reductive amination |
| US8840879B2 (en) | 2004-03-11 | 2014-09-23 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
| US8017739B2 (en) | 2004-03-11 | 2011-09-13 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
| US8404834B2 (en) | 2007-12-14 | 2013-03-26 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7209737A (enExample) | 1973-01-16 |
| FR2145722A1 (enExample) | 1973-02-23 |
| US3873614A (en) | 1975-03-25 |
| GB1385403A (en) | 1975-02-26 |
| FR2145722B1 (enExample) | 1976-10-29 |
| CA959047A (en) | 1974-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |