TW200909463A - A process for the manufacture of natural oil hydroxylates - Google Patents
A process for the manufacture of natural oil hydroxylates Download PDFInfo
- Publication number
- TW200909463A TW200909463A TW097114093A TW97114093A TW200909463A TW 200909463 A TW200909463 A TW 200909463A TW 097114093 A TW097114093 A TW 097114093A TW 97114093 A TW97114093 A TW 97114093A TW 200909463 A TW200909463 A TW 200909463A
- Authority
- TW
- Taiwan
- Prior art keywords
- oil
- polyol
- weight
- natural
- hydroxylated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 109
- 230000008569 process Effects 0.000 title abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 229920005862 polyol Polymers 0.000 claims abstract description 190
- 150000003077 polyols Chemical class 0.000 claims abstract description 179
- 239000003921 oil Substances 0.000 claims abstract description 86
- 235000019198 oils Nutrition 0.000 claims abstract description 86
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 71
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 54
- 239000008158 vegetable oil Substances 0.000 claims abstract description 54
- -1 amino compound Chemical class 0.000 claims abstract description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 51
- 239000000194 fatty acid Substances 0.000 claims description 32
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 31
- 229930195729 fatty acid Natural products 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 150000004665 fatty acids Chemical class 0.000 claims description 21
- 239000004814 polyurethane Substances 0.000 claims description 20
- 229920002635 polyurethane Polymers 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 18
- 235000011187 glycerol Nutrition 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 239000003549 soybean oil Substances 0.000 claims description 13
- 235000012424 soybean oil Nutrition 0.000 claims description 13
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 12
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical class OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 5
- 241000221089 Jatropha Species 0.000 claims description 4
- 229930182558 Sterol Natural products 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 150000003432 sterols Chemical class 0.000 claims description 4
- 235000003702 sterols Nutrition 0.000 claims description 4
- 241001474374 Blennius Species 0.000 claims description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000828 canola oil Substances 0.000 claims description 3
- 235000019519 canola oil Nutrition 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000005313 fatty acid group Chemical group 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical group 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- WRDNDQAJVPZACU-UHFFFAOYSA-N 2-(2-ethylanilino)ethanol Chemical compound CCC1=CC=CC=C1NCCO WRDNDQAJVPZACU-UHFFFAOYSA-N 0.000 claims description 2
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 claims description 2
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 2
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 2
- 244000188595 Brassica sinapistrum Species 0.000 claims description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- RJUAEBLXGFKZMS-UHFFFAOYSA-N piperidin-1-ylmethanol Chemical compound OCN1CCCCC1 RJUAEBLXGFKZMS-UHFFFAOYSA-N 0.000 claims description 2
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000003039 volatile agent Substances 0.000 claims description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims 2
- ILDXSRFKXABMHH-UHFFFAOYSA-N 2-(2-aminophenyl)ethanol Chemical compound NC1=CC=CC=C1CCO ILDXSRFKXABMHH-UHFFFAOYSA-N 0.000 claims 1
- 235000019737 Animal fat Nutrition 0.000 claims 1
- 241000195493 Cryptophyta Species 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 229940116333 ethyl lactate Drugs 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 239000010642 eucalyptus oil Substances 0.000 claims 1
- 229940044949 eucalyptus oil Drugs 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 109
- 238000006243 chemical reaction Methods 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 17
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000052 vinegar Substances 0.000 description 10
- 235000021419 vinegar Nutrition 0.000 description 10
- 230000009257 reactivity Effects 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000007142 ring opening reaction Methods 0.000 description 8
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- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
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- 238000007710 freezing Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
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- 238000005345 coagulation Methods 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
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- 238000006735 epoxidation reaction Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
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- 239000004793 Polystyrene Substances 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
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- 238000012512 characterization method Methods 0.000 description 2
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- 238000010257 thawing Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 125000005457 triglyceride group Chemical group 0.000 description 2
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- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
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- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FIGWEYVFWZJJSE-UHFFFAOYSA-N hydrazine 2-(2-hydroxyethylamino)ethanol Chemical compound NN.N(CCO)CCO FIGWEYVFWZJJSE-UHFFFAOYSA-N 0.000 description 1
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- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- MQVRLONNONYDJP-UHFFFAOYSA-N propane-1,1,2,3-tetrol Chemical compound OCC(O)C(O)O MQVRLONNONYDJP-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
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Classifications
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| US92503407P | 2007-04-18 | 2007-04-18 | |
| US12/082,808 US8097739B2 (en) | 2007-04-18 | 2008-04-15 | Process for the manufacture of natural oil hydroxylates |
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| TW200909463A true TW200909463A (en) | 2009-03-01 |
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| TW097114093A TW200909463A (en) | 2007-04-18 | 2008-04-18 | A process for the manufacture of natural oil hydroxylates |
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| EP (1) | EP2142583A4 (https=) |
| JP (1) | JP2010524946A (https=) |
| CN (1) | CN101715464A (https=) |
| CA (1) | CA2684464A1 (https=) |
| MX (1) | MX2009011186A (https=) |
| TW (1) | TW200909463A (https=) |
| WO (1) | WO2008130646A1 (https=) |
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| ATE393791T1 (de) * | 2004-06-10 | 2008-05-15 | Dow Global Technologies Inc | Mittels fettsäureamid-polyole hergestellte polyurethanteppichunterlagen |
| US7794814B2 (en) * | 2004-10-25 | 2010-09-14 | Dow Global Technologies Inc. | Polyurethane carpet backings made using hydroxymethylated polyester polyols |
| WO2006093877A1 (en) * | 2005-02-28 | 2006-09-08 | Michigan State University | Improved biodiesel additive and method of preparation thereof |
| US8217193B2 (en) * | 2005-02-28 | 2012-07-10 | Board Of Trustees Of Michigan State University | Modified fatty acid esters and method of preparation thereof |
| US8871960B2 (en) | 2005-04-26 | 2014-10-28 | Battelle Memorial Institute | Preparation of esters and polyols by initial oxidative cleavage of fatty acids followed by esterification reactions |
| US8247582B2 (en) | 2006-02-07 | 2012-08-21 | Battelle Memorial Institute | Esters of 5-hydroxymethylfurfural and methods for their preparation |
| AR064261A1 (es) * | 2006-11-16 | 2009-03-25 | Cargill Inc | Espumas poliuretanicas viscoelasticas que comprenden polioles de aceite natural oligomerico amidado o transesterificado |
| US20090062432A1 (en) * | 2007-06-11 | 2009-03-05 | Doesburg Van I | Novel polyurethane compositions including castor oil |
| BRPI0923798B1 (pt) | 2008-12-31 | 2020-04-14 | Battelle Memorial Institute | métodos para produzir um éster e para produzir amidas |
| BRPI0923833B1 (pt) | 2008-12-31 | 2020-04-14 | Battelle Memorial Institute | métodos para produzir um éster e amidas |
| CA2748618C (en) | 2008-12-31 | 2016-06-07 | Battelle Memorial Institute | Solvent-less preparation of polyols by ozonolysis |
| JP2012520377A (ja) | 2009-03-13 | 2012-09-06 | バテル・メモリアル・インスティテュート | 変性植物油潤滑剤 |
| US8022257B2 (en) * | 2009-09-03 | 2011-09-20 | The Ohio State University Research Foundation | Methods for producing polyols using crude glycerin |
| US8034859B2 (en) * | 2010-01-22 | 2011-10-11 | Ford Global Technologies, Llc | Rubber compositions containing an oil blend of a petroleum oil and a biobased oil and methods of making the same |
| BR112012033611B1 (pt) † | 2010-06-30 | 2020-11-10 | Dow Global Technologies Llc | composição compreendendo um polímero com terminação silano reticulável e método para produzir uma composição compreendendo um polímero com terminação silano reticulável |
| US20140275310A1 (en) * | 2013-03-14 | 2014-09-18 | Bayer Materialscience, Llc | Novel polymer polyols based on natural oils polyols |
| CA2993870C (en) | 2015-07-31 | 2023-09-12 | The Governors Of The University Of Alberta | Synthesis of polyols suitable for castor oil replacement |
| CN107151212B (zh) * | 2016-03-03 | 2020-01-10 | 中国石油化工股份有限公司 | 一种低羟值桐油多元醇及其制备方法 |
| CN107151209B (zh) * | 2016-03-03 | 2020-01-10 | 中国石油化工股份有限公司 | 一种利用离子液体合成桐油多元醇的方法 |
| CN109929097A (zh) * | 2019-03-20 | 2019-06-25 | 安徽凤凰涂料科技有限公司 | 一种无溶剂涂料用可降解的聚合物多元醇及其合成方法 |
| CN111411023B (zh) * | 2020-03-30 | 2021-05-25 | 南京工业大学 | 一种植物油多元醇及其制备方法与应用 |
| CN112480649A (zh) * | 2020-11-26 | 2021-03-12 | 上海应用技术大学 | 一种二氧化钛/tpu复合型亲水薄膜及其制备方法 |
| CN113461557B (zh) * | 2021-04-02 | 2023-08-15 | 苏州丰倍生物科技股份有限公司 | 一种羟乙基乙二胺衍生物、脂肪酸酯衍生物及其制备方法 |
| CN115368532B (zh) * | 2022-09-01 | 2023-08-08 | 安徽农业大学 | 一种交联热固型聚氨酯弹性体及其制备方法 |
| CN116731660A (zh) * | 2023-07-04 | 2023-09-12 | 江西天永诚高分子材料有限公司 | 一种高导热、可拆卸聚氨酯结构胶及其制备方法 |
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| DE1248919B (de) | 1967-10-12 | 1967-08-31 | Hermann Joseph Neidhart, Genf-Bernex, Rico Neidhart, Genf (Schweiz) | Verfahren und Vorrichtung zum Zusammenbau von Torsionsfederungselemenien |
| US3485779A (en) * | 1967-10-19 | 1969-12-23 | Us Agriculture | Diisocyanate modified vegetable oil hydroxyl-terminated polyesteramide coatings |
| JPS63139993A (ja) * | 1986-12-02 | 1988-06-11 | ミヨシ油脂株式会社 | 制菌及び防虫効果並びに界面活性を有する油脂誘導体 |
| DE4434694C1 (de) * | 1994-09-28 | 1996-03-07 | Josef Lechner | Verwendung von Polyolderivaten als innere Trennmittel bei der Herstellung von Polyurethan-Formteilen |
| US20020058774A1 (en) | 2000-09-06 | 2002-05-16 | Kurth Thomas M. | Transesterified polyol having selectable and increased functionality and urethane material products formed using the polyol |
| US20030191274A1 (en) | 2001-10-10 | 2003-10-09 | Kurth Thomas M. | Oxylated vegetable-based polyol having increased functionality and urethane material formed using the polyol |
| MXPA00011394A (es) * | 2000-11-21 | 2003-03-12 | Resinas Y Materiales S A De C | Proceso mejorado para la obtencion de polioles oleoquimicos. |
| WO2004096882A1 (en) * | 2003-04-25 | 2004-11-11 | Dow Global Technologies, Inc. | Vegetable oil based polyols and polyurethanes made therefrom |
| WO2004099227A2 (en) | 2003-04-30 | 2004-11-18 | Michigan State University | Polyol fatty acid polyesters process and polyurethanes therefrom |
| EP1710268B1 (en) | 2004-01-30 | 2008-08-27 | Kaneka Corporation | Method for producing oxyalkylene polymer |
| ATE393791T1 (de) | 2004-06-10 | 2008-05-15 | Dow Global Technologies Inc | Mittels fettsäureamid-polyole hergestellte polyurethanteppichunterlagen |
| WO2006093874A2 (en) | 2005-02-28 | 2006-09-08 | Michigan State University | Novel triglycerides and method of preparation thereof |
| EP1856023A4 (en) | 2005-03-03 | 2010-08-04 | South Dakota Soybean Processor | NOVEL POLYOLS DERIVED FROM AN OXIDATION PROCESS FROM A PLANT OIL |
| SI1883690T1 (sl) * | 2005-04-26 | 2012-06-29 | Battelle Memorial Institute | Postopek za proizvodnjo poliolov iz olj in njih uporaba pri proizvodnji poliestrov in poliuretanov |
| DE102005056432A1 (de) | 2005-11-26 | 2007-05-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen auf Basis natürlicher Öle |
| CN100390129C (zh) | 2006-04-16 | 2008-05-28 | 南京红宝丽股份有限公司 | 一种采用菜籽油制备的生物基多元醇 |
| CN100390128C (zh) | 2006-04-16 | 2008-05-28 | 南京红宝丽股份有限公司 | 一种利用菜籽油制备的生物基多元醇 |
-
2008
- 2008-04-15 US US12/082,808 patent/US8097739B2/en active Active
- 2008-04-18 WO PCT/US2008/005051 patent/WO2008130646A1/en not_active Ceased
- 2008-04-18 CA CA002684464A patent/CA2684464A1/en not_active Abandoned
- 2008-04-18 EP EP08754094A patent/EP2142583A4/en not_active Withdrawn
- 2008-04-18 JP JP2010504112A patent/JP2010524946A/ja active Pending
- 2008-04-18 MX MX2009011186A patent/MX2009011186A/es active IP Right Grant
- 2008-04-18 TW TW097114093A patent/TW200909463A/zh unknown
- 2008-04-18 CN CN200880016827A patent/CN101715464A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008130646A1 (en) | 2008-10-30 |
| EP2142583A4 (en) | 2011-10-05 |
| CN101715464A (zh) | 2010-05-26 |
| US8097739B2 (en) | 2012-01-17 |
| CA2684464A1 (en) | 2008-10-30 |
| MX2009011186A (es) | 2010-02-17 |
| US20080262259A1 (en) | 2008-10-23 |
| EP2142583A1 (en) | 2010-01-13 |
| JP2010524946A (ja) | 2010-07-22 |
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