JP5345758B2 - ポリトリメチレンエーテルグリコールポリマーからのカラーボディの除去 - Google Patents
ポリトリメチレンエーテルグリコールポリマーからのカラーボディの除去 Download PDFInfo
- Publication number
- JP5345758B2 JP5345758B2 JP2006532801A JP2006532801A JP5345758B2 JP 5345758 B2 JP5345758 B2 JP 5345758B2 JP 2006532801 A JP2006532801 A JP 2006532801A JP 2006532801 A JP2006532801 A JP 2006532801A JP 5345758 B2 JP5345758 B2 JP 5345758B2
- Authority
- JP
- Japan
- Prior art keywords
- color
- po3g
- polymer
- adsorbent
- activated carbon
- 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.)
- Expired - Fee Related
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 40
- -1 polytrimethylene Polymers 0.000 title claims description 30
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 25
- 229920000642 polymer Polymers 0.000 title description 49
- 241001550224 Apha Species 0.000 claims abstract description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 45
- 239000003463 adsorbent Substances 0.000 abstract description 43
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 19
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 19
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004534 cecum Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229960002479 isosorbide Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ROZAMBDRZCZIJG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropentane-1,5-diol Chemical compound OCCC(F)(F)C(F)(F)C(O)(F)F ROZAMBDRZCZIJG-UHFFFAOYSA-N 0.000 description 1
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- NHEKBXPLFJSSBZ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorohexane-1,6-diol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)CO NHEKBXPLFJSSBZ-UHFFFAOYSA-N 0.000 description 1
- WECIKJKLCDCIMY-UHFFFAOYSA-N 2-chloro-n-(2-cyanoethyl)acetamide Chemical compound ClCC(=O)NCCC#N WECIKJKLCDCIMY-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- CUCYNAXISGIFIS-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-hexadecafluorododecane-1,12-diol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCO CUCYNAXISGIFIS-UHFFFAOYSA-N 0.000 description 1
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/46—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/26—Drying gases or vapours
- B01D53/263—Drying gases or vapours by absorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/36—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46822603P | 2003-05-06 | 2003-05-06 | |
| US60/468,226 | 2003-05-06 | ||
| US10/634,687 US7009082B2 (en) | 2003-05-06 | 2003-08-05 | Removal of color bodies from polytrimethylene ether glycol polymers |
| US10/634,687 | 2003-08-05 | ||
| PCT/US2004/014042 WO2004101470A2 (en) | 2003-05-06 | 2004-05-05 | Removal of color bodies from polytrimethylene ether glycol polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007501325A JP2007501325A (ja) | 2007-01-25 |
| JP2007501325A5 JP2007501325A5 (https=) | 2013-08-08 |
| JP5345758B2 true JP5345758B2 (ja) | 2013-11-20 |
Family
ID=33423709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006532801A Expired - Fee Related JP5345758B2 (ja) | 2003-05-06 | 2004-05-05 | ポリトリメチレンエーテルグリコールポリマーからのカラーボディの除去 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7009082B2 (https=) |
| EP (2) | EP1620380B1 (https=) |
| JP (1) | JP5345758B2 (https=) |
| KR (1) | KR101105072B1 (https=) |
| BR (1) | BRPI0410483A (https=) |
| CA (1) | CA2522772A1 (https=) |
| ES (2) | ES2407869T3 (https=) |
| MX (1) | MXPA05011828A (https=) |
| WO (1) | WO2004101470A2 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US7342142B2 (en) * | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
| US7084311B2 (en) | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| US7745668B2 (en) * | 2003-05-06 | 2010-06-29 | E. I. Du Pont De Nemours And Company | Processes for reducing color in polytrimethylene ether glycol polymers |
| US20080103217A1 (en) * | 2006-10-31 | 2008-05-01 | Hari Babu Sunkara | Polyether ester elastomer composition |
| US7074969B2 (en) * | 2004-06-18 | 2006-07-11 | E.I. Du Pont De Nemours And Company | Process for preparation of polytrimethylene ether glycols |
| US7629396B2 (en) * | 2005-02-23 | 2009-12-08 | E.I. Du Pont De Nemours And Company | Silicon-containing polytrimethylene homo- for copolyether composition |
| US20060189711A1 (en) * | 2005-02-23 | 2006-08-24 | Ng Howard C | Silicon-containing polytrimethylene homo- or copolyether composition |
| US7282159B2 (en) * | 2005-02-25 | 2007-10-16 | E.I. Dupont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene ether glycol or polytrimethylene ether ester glycol based heat transfer fluid |
| US7413677B2 (en) * | 2005-02-25 | 2008-08-19 | E. I. Du Pont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene homo- or copolyether glycol based heat transfer fluid |
| US7476344B2 (en) * | 2005-02-25 | 2009-01-13 | E.I. Du Pont De Nemours | Electrical apparatuses containing polytrimethylene homo- or copolyether glycol based electrical insulation fluids |
| US20060247378A1 (en) * | 2005-05-02 | 2006-11-02 | Sunkara Hari B | Thermoplastic elastomer blend, method of manufacture and use thereof |
| US7244790B2 (en) * | 2005-05-02 | 2007-07-17 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend, method of manufacture and use thereof |
| US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US20070129524A1 (en) * | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
| US20070203371A1 (en) * | 2006-01-23 | 2007-08-30 | Sunkara Hari B | Process for producing polytrimethylene ether glycol |
| US20080039582A1 (en) * | 2006-07-28 | 2008-02-14 | Hari Babu Sunkara | Polytrimethylene ether-based polyurethane ionomers |
| US7531593B2 (en) | 2006-10-31 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend composition |
| US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US20080135662A1 (en) * | 2006-12-06 | 2008-06-12 | Chang Jing C | Melt-spun elastoester multifilament yarns |
| DE102007013963A1 (de) * | 2007-03-23 | 2008-09-25 | Lanxess Deutschland Gmbh | Verfahren zur Farbzahlverbesserung von Trimethylolpropan |
| CN101802149A (zh) * | 2007-08-24 | 2010-08-11 | 纳幕尔杜邦公司 | 润滑油组合物 |
| AU2008293753A1 (en) * | 2007-08-24 | 2009-03-05 | E. I. Du Pont De Nemours And Company | Lubrication oil compositions |
| JP5366168B2 (ja) * | 2007-08-24 | 2013-12-11 | 富山県 | ポリグリセロールデンドリマーの精製方法 |
| US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
| CN101842469A (zh) * | 2007-08-24 | 2010-09-22 | 纳幕尔杜邦公司 | 润滑油组合物 |
| CN101784643A (zh) * | 2007-08-24 | 2010-07-21 | 纳幕尔杜邦公司 | 润滑油组合物 |
| EP2205659B1 (en) * | 2007-11-01 | 2014-06-04 | E. I. du Pont de Nemours and Company | Preparation of polytrimethylene ether glycol or copolymers thereof |
| US7919017B2 (en) * | 2007-11-12 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Electrical insulation fluids for use in electrical apparatus |
| JP5713274B2 (ja) * | 2009-03-31 | 2015-05-07 | 日油株式会社 | 高分子量ポリオキシアルキレン誘導体の精製方法 |
| US20100267994A1 (en) * | 2009-04-16 | 2010-10-21 | E. I. Du Pont De Nemours And Company | Processes for preparing polytrimethylene glycol using ion exchange resins |
| WO2011011276A2 (en) * | 2009-07-22 | 2011-01-27 | E. I. Du Pont De Nemours And Company | Methods for synthesizing polyether diols and polyester diols |
| US20110172360A1 (en) * | 2009-07-22 | 2011-07-14 | E.I. Du Pont De Nemours And Company | Methods for synthesizing polyether diols and polyester diols |
| EP2483328A4 (en) * | 2009-09-30 | 2014-09-24 | Du Pont | POLYTRIMETHYLENETHERGLYCOL OR COPOLYMERS THEREOF WITH IMPROVED COLOR AND METHOD FOR THE PRODUCTION THEREOF |
| EP2516505B1 (en) * | 2009-12-21 | 2014-09-17 | E.I. Du Pont De Nemours And Company | Processes for producing polytrimethylene ether glycol |
| WO2012076532A1 (en) | 2010-12-08 | 2012-06-14 | Shell Internationale Research Maatschappij B.V. | Process for purifying aryl group containing carbonates |
| WO2012076519A1 (en) | 2010-12-08 | 2012-06-14 | Shell Internationale Research Maatschappij B.V. | Process for purifying dialkyl carbonate |
| US8247526B2 (en) | 2010-12-20 | 2012-08-21 | E I Du Pont De Nemours And Company | Process for the preparation of polyalkylene ether glycol |
| JP5936244B2 (ja) * | 2011-04-26 | 2016-06-22 | 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 | ポリトリメチレンエーテルグリコールを調製する方法 |
| US11579127B2 (en) * | 2018-06-29 | 2023-02-14 | Asp Global Manufacturing Gmbh | Apparatus, method, and system for indication of an oxidative treatment |
| KR102845197B1 (ko) * | 2022-08-02 | 2025-08-12 | 동아대학교 산학협력단 | 천연물을 포함한 열가소성 폴리우레탄 3d 프린터용 필라멘트 및 이의 제조방법 |
| WO2026028076A1 (en) | 2024-07-30 | 2026-02-05 | C.O.I.M. S.P.A. - Chimica Organica Industriale Milanese | Synthesis of polyether polyols commercially suitable for the polyurethane industry, by polymerisation of polyfunctional alcohols |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1478985A (en) * | 1919-03-22 | 1923-12-25 | Morrell Jacque Cyrus | Artificial or synthetic charcoal and process of producing the same |
| US2315584A (en) * | 1941-08-16 | 1943-04-06 | Hercules Powder Co Ltd | Tall-oil refining |
| US2520733A (en) | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
| US3326985A (en) | 1964-12-29 | 1967-06-20 | Shell Oil Co | Polytrimethylene glycol |
| US4213000A (en) | 1979-05-29 | 1980-07-15 | E. I. Du Pont De Nemours And Company | Reducing color formers in 1,4-butanediol |
| US4243831A (en) * | 1979-07-30 | 1981-01-06 | Uop Inc. | Removal of peroxides and color bodies from internal olefins by solid adsorbents |
| US4885410A (en) | 1987-11-27 | 1989-12-05 | Gaf Corporation | Hydrogenation catalyst |
| DE3917645A1 (de) | 1988-06-23 | 1989-12-28 | Henkel Kgaa | Verfahren zum abtrennen von farbstoffen und/oder geruchsstoffen aus reduktionsstabile wertprodukte enthaltenden fermenterbruehen |
| JPH06210104A (ja) * | 1993-01-21 | 1994-08-02 | Daicel Chem Ind Ltd | ポリオキシテトラメチレングリコ−ルの精製方法 |
| JPH06287296A (ja) * | 1993-03-31 | 1994-10-11 | Hodogaya Chem Co Ltd | ポリオキシアルキレングリコールブロック共重合体の製造方法 |
| DE4342345C2 (de) | 1993-12-11 | 1998-10-22 | Merck Patent Gmbh | Entfärbung von Fermentationslösungen |
| WO1996011223A1 (de) * | 1994-10-07 | 1996-04-18 | Basf Aktiengesellschaft | Verfahren zur reinigung von polyethern, polyestern und polyetherestern |
| US5527973A (en) | 1994-12-16 | 1996-06-18 | Kelsey; Donald R. | Purification of 1,3-propanediol |
| US5633362A (en) | 1995-05-12 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-propanediol from glycerol by recombinant bacteria expressing recombinant diol dehydratase |
| US5686276A (en) | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| US6111137A (en) | 1996-12-20 | 2000-08-29 | Mitsui Chemicals, Inc. | Purification process of lactic acid |
| JPH10195191A (ja) * | 1997-01-16 | 1998-07-28 | Mitsui Chem Inc | ポリオキシアルキレンポリオールならびにポリマー分散ポリオールの製造方法 および それを用いた軟質ポリウレタン発泡体の製造方法 |
| US6235948B1 (en) | 1998-08-18 | 2001-05-22 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,3-propanediol |
| US6245844B1 (en) | 1998-09-18 | 2001-06-12 | E. I. Du Pont De Nemours And Company | Nucleating agent for polyesters |
| US6720459B2 (en) * | 1999-12-17 | 2004-04-13 | E. I. Du Pont Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| DE60028086T2 (de) * | 1999-12-17 | 2006-12-21 | E.I. Dupont De Nemours And Co., Wilmington | Herstellung von polytrimethylene ether glycol und copolymere davon |
| JP2002030144A (ja) * | 2000-07-14 | 2002-01-31 | Nof Corp | ポリエーテル化合物の製造方法 |
-
2003
- 2003-08-05 US US10/634,687 patent/US7009082B2/en not_active Expired - Lifetime
-
2004
- 2004-05-05 ES ES11161761T patent/ES2407869T3/es not_active Expired - Lifetime
- 2004-05-05 CA CA002522772A patent/CA2522772A1/en not_active Abandoned
- 2004-05-05 BR BRPI0410483-8A patent/BRPI0410483A/pt not_active IP Right Cessation
- 2004-05-05 EP EP04751436A patent/EP1620380B1/en not_active Expired - Lifetime
- 2004-05-05 WO PCT/US2004/014042 patent/WO2004101470A2/en not_active Ceased
- 2004-05-05 KR KR1020057020962A patent/KR101105072B1/ko not_active Expired - Lifetime
- 2004-05-05 MX MXPA05011828A patent/MXPA05011828A/es active IP Right Grant
- 2004-05-05 JP JP2006532801A patent/JP5345758B2/ja not_active Expired - Fee Related
- 2004-05-05 ES ES04751436T patent/ES2378159T3/es not_active Expired - Lifetime
- 2004-05-05 EP EP11161761A patent/EP2390278B1/en not_active Expired - Lifetime
-
2005
- 2005-11-10 US US11/271,299 patent/US7294746B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20060069290A1 (en) | 2006-03-30 |
| MXPA05011828A (es) | 2006-02-17 |
| EP2390278B1 (en) | 2013-03-27 |
| CA2522772A1 (en) | 2004-11-25 |
| WO2004101470A3 (en) | 2005-01-27 |
| BRPI0410483A (pt) | 2006-06-13 |
| US7294746B2 (en) | 2007-11-13 |
| EP1620380B1 (en) | 2011-12-28 |
| EP1620380A2 (en) | 2006-02-01 |
| KR20060024373A (ko) | 2006-03-16 |
| EP1620380A4 (en) | 2009-02-18 |
| US7009082B2 (en) | 2006-03-07 |
| JP2007501325A (ja) | 2007-01-25 |
| EP2390278A1 (en) | 2011-11-30 |
| ES2407869T3 (es) | 2013-06-14 |
| WO2004101470A2 (en) | 2004-11-25 |
| KR101105072B1 (ko) | 2012-01-13 |
| ES2378159T3 (es) | 2012-04-09 |
| US20040225162A1 (en) | 2004-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5345758B2 (ja) | ポリトリメチレンエーテルグリコールポリマーからのカラーボディの除去 | |
| US7323539B2 (en) | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality | |
| JP4898444B2 (ja) | 生化学的に誘導された１，３−プロパンジオールからの優れた品質のポリトリメチレンエーテルグリコール | |
| JP4642028B2 (ja) | 化学的に誘導された１，３−プロパンジオールの水素化 | |
| JP4908218B2 (ja) | 生化学的に誘導された１，３−プロパンジオールの水素化 | |
| TW506963B (en) | Process for the purification of 1,3-propanediol | |
| JP2007503522A (ja) | ポリトリメチレンエーテルグリコールの水素化 | |
| US7745668B2 (en) | Processes for reducing color in polytrimethylene ether glycol polymers | |
| TWI364319B (en) | Removal of color bodies from polytrimethylene ether glycol polymers | |
| ES2370018T3 (es) | Politrimetilen éter glicol con excelente calidad a partir de 1,3-propanodiol bioquímicamente derivado. | |
| CN1816511A (zh) | 聚三亚甲基醚二醇的氢化 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070426 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070517 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100301 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100323 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100623 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100630 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100723 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20101206 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110513 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130325 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130328 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130329 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20130625 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130815 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5345758 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |