DE1295811B - Verfahren zur Herstellung von Polyoxyalkylaethern von Glycosiden abgebauter Staerke - Google Patents
Verfahren zur Herstellung von Polyoxyalkylaethern von Glycosiden abgebauter StaerkeInfo
- Publication number
- DE1295811B DE1295811B DEM55906A DEM0055906A DE1295811B DE 1295811 B DE1295811 B DE 1295811B DE M55906 A DEM55906 A DE M55906A DE M0055906 A DEM0055906 A DE M0055906A DE 1295811 B DE1295811 B DE 1295811B
- Authority
- DE
- Germany
- Prior art keywords
- starch
- reacted
- mol
- moles
- polyol
- 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
- 229920002472 Starch Polymers 0.000 title claims description 45
- 239000008107 starch Substances 0.000 title claims description 42
- 235000019698 starch Nutrition 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 15
- 229930182470 glycoside Natural products 0.000 title claims description 10
- 150000002338 glycosides Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000002170 ethers Chemical class 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 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 claims 2
- 229920000881 Modified starch Polymers 0.000 claims 1
- 239000004368 Modified starch Substances 0.000 claims 1
- -1 aryl sulfonic acid Chemical compound 0.000 claims 1
- 235000019426 modified starch Nutrition 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920002261 Corn starch Polymers 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 229940100445 wheat starch Drugs 0.000 description 3
- 229920000856 Amylose Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920001685 Amylomaize Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000009430 Thespesia populnea Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005338 frosted glass Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17615562A | 1962-02-27 | 1962-02-27 | |
| US187443A US3165508A (en) | 1962-02-27 | 1962-04-13 | Degraded starch polyoxyalkylene ether compositions and process for producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1295811B true DE1295811B (de) | 1969-05-22 |
Family
ID=26871938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM55906A Pending DE1295811B (de) | 1962-02-27 | 1963-02-26 | Verfahren zur Herstellung von Polyoxyalkylaethern von Glycosiden abgebauter Staerke |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3165508A (en:Method) |
| BE (1) | BE628841A (en:Method) |
| DE (1) | DE1295811B (en:Method) |
| GB (1) | GB1006516A (en:Method) |
| NL (2) | NL140266B (en:Method) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053766A (en:Method) * | 1962-06-27 | |||
| US3336291A (en) * | 1963-10-07 | 1967-08-15 | Wyandotte Chemicals Corp | Oxyalkylene condensates of cellulose useful in the preparation of urethanes |
| US3325472A (en) * | 1964-06-18 | 1967-06-13 | Mortimer D Sackler | Polycyclohexose-polyoxyethyleneglycol suppository bases |
| US3402170A (en) * | 1965-03-26 | 1968-09-17 | Olin Mathieson | Process for preparing starch-based polyhydroxypolyoxyalkylene ethers |
| US3405080A (en) * | 1965-10-07 | 1968-10-08 | Agriculture Usa | Process for preparing polyether-polyurethane-starch resins |
| US3346558A (en) * | 1965-11-19 | 1967-10-10 | Staley Mfg Co A E | Continuous process for preparing polyol gly cosides |
| US3488302A (en) * | 1966-06-20 | 1970-01-06 | Charles Odus Pyron | Ambient temperature stable mixture of isocyanate prepolymer and solid polyol |
| US4585858A (en) * | 1967-01-03 | 1986-04-29 | Cpc International Inc. | Starch-based polyether polyols |
| US3516952A (en) * | 1967-04-03 | 1970-06-23 | Cpc International Inc | Curable and cured epoxy-carbohydrate polyether resin compositions |
| US3507817A (en) * | 1967-05-01 | 1970-04-21 | Cpc International Inc | Acrylic-epoxy-carbohydrate polyether coating compositions |
| US3957702A (en) * | 1967-05-10 | 1976-05-18 | Cpc International Inc. | Flame retardant polyurethane foams |
| US3910878A (en) * | 1968-09-11 | 1975-10-07 | Dow Chemical Co | Latent oxyalkylation catalysts |
| US4197372A (en) * | 1978-01-16 | 1980-04-08 | Krause Milling Company | Semi-flexible polyurethane foams containing amylaceous material and process for preparing same |
| US4223129A (en) * | 1978-09-01 | 1980-09-16 | A. E. Staley Manufacturing Company | Continuous process for making alkyl aldosides from starch or other carbohydrates |
| US4654375A (en) * | 1986-04-03 | 1987-03-31 | Sealed Air Corporation | Fire-retardant polyurethane foam and method and resin for preparing the same |
| US5095054A (en) * | 1988-02-03 | 1992-03-10 | Warner-Lambert Company | Polymer compositions containing destructurized starch |
| US20060252660A1 (en) * | 2005-05-09 | 2006-11-09 | Akhilesh Duggal | Hydrolytically stable viscosity index improves |
| US8173718B2 (en) | 2007-09-18 | 2012-05-08 | Georgia-Pacific Consumer Products Lp | Resilient, water dispersible polyurethane foams and products incorporating same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1002307B (de) * | 1953-03-13 | 1957-02-14 | Corn Prod Refining Co | Verfahren zur Herstellung von Staerkeaethern |
| DE1014490B (de) * | 1954-09-29 | 1957-08-22 | Duintjer Wilkens Meihuizen & C | Behandlung von Staerke |
| DE1019288B (de) * | 1953-05-19 | 1957-11-14 | Union Carbide Corp | Verfahren zur Herstellung von fester, granulierter, wasserloeslicher Oxyalkylstaerke |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390507A (en) * | 1941-01-21 | 1945-12-11 | Corn Prod Refining Co | Production of alkyl glycosides |
| US2407002A (en) * | 1944-10-21 | 1946-09-03 | Atlas Powder Co | Glycol glucosides and derivatives thereof |
| US3073788A (en) * | 1959-11-17 | 1963-01-15 | Union Carbide Corp | Polyurethane foams |
-
0
- BE BE628841D patent/BE628841A/xx unknown
- NL NL289520D patent/NL289520A/xx unknown
-
1962
- 1962-04-13 US US187443A patent/US3165508A/en not_active Expired - Lifetime
-
1963
- 1963-02-21 GB GB6998/63A patent/GB1006516A/en not_active Expired
- 1963-02-26 DE DEM55906A patent/DE1295811B/de active Pending
- 1963-02-27 NL NL63289520A patent/NL140266B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1002307B (de) * | 1953-03-13 | 1957-02-14 | Corn Prod Refining Co | Verfahren zur Herstellung von Staerkeaethern |
| DE1019288B (de) * | 1953-05-19 | 1957-11-14 | Union Carbide Corp | Verfahren zur Herstellung von fester, granulierter, wasserloeslicher Oxyalkylstaerke |
| DE1014490B (de) * | 1954-09-29 | 1957-08-22 | Duintjer Wilkens Meihuizen & C | Behandlung von Staerke |
Also Published As
| Publication number | Publication date |
|---|---|
| BE628841A (en:Method) | |
| NL289520A (en:Method) | |
| NL140266B (nl) | 1973-11-15 |
| GB1006516A (en) | 1965-10-06 |
| US3165508A (en) | 1965-01-12 |
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