ES2378359T3 - Procesos sin disolvente para la polimerización de un carbonato de trimetileno a poli(trimetilenglicol carbonato trimetilenglicol éter) diol - Google Patents
Procesos sin disolvente para la polimerización de un carbonato de trimetileno a poli(trimetilenglicol carbonato trimetilenglicol éter) diol Download PDFInfo
- Publication number
- ES2378359T3 ES2378359T3 ES08855247T ES08855247T ES2378359T3 ES 2378359 T3 ES2378359 T3 ES 2378359T3 ES 08855247 T ES08855247 T ES 08855247T ES 08855247 T ES08855247 T ES 08855247T ES 2378359 T3 ES2378359 T3 ES 2378359T3
- Authority
- ES
- Spain
- Prior art keywords
- carbonate
- trimethylene
- trimethylene glycol
- poly
- diol
- 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.)
- Active
Links
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 22
- -1 poly (trimethylene glycol carbonate trimethylene glycol Chemical compound 0.000 title claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000002009 diols Chemical class 0.000 title claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 title abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000006737 (C6-C20) arylalkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
- SELFXCFVPOJKBE-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonic acid Chemical compound C=COCC(C)OCCS(O)(=O)=O SELFXCFVPOJKBE-UHFFFAOYSA-N 0.000 claims 1
- 239000011973 solid acid Substances 0.000 abstract description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 13
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 13
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
- 239000004914 cyclooctane Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 229920001692 polycarbonate urethane Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- AUUAIQGEFIEHRO-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxyethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)=C(F)F AUUAIQGEFIEHRO-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- RYHHSZLUOAMLFC-UHFFFAOYSA-N carbonic acid;propane-1,3-diol Chemical compound OC(O)=O.OCCCO RYHHSZLUOAMLFC-UHFFFAOYSA-N 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99168707P | 2007-11-30 | 2007-11-30 | |
| US991687P | 2007-11-30 | ||
| PCT/US2008/084693 WO2009070587A1 (en) | 2007-11-30 | 2008-11-25 | Solventless processes for the polymerization of a trimethylene carbonate to a poly(trimethylene glycol carbonate trimethylene glycol ether) diol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2378359T3 true ES2378359T3 (es) | 2012-04-11 |
Family
ID=40350063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08855247T Active ES2378359T3 (es) | 2007-11-30 | 2008-11-25 | Procesos sin disolvente para la polimerización de un carbonato de trimetileno a poli(trimetilenglicol carbonato trimetilenglicol éter) diol |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7790833B2 (enExample) |
| EP (1) | EP2215142B1 (enExample) |
| JP (1) | JP2011505468A (enExample) |
| KR (1) | KR20100102629A (enExample) |
| CN (1) | CN101878244A (enExample) |
| AT (1) | ATE538159T1 (enExample) |
| AU (1) | AU2008329778A1 (enExample) |
| BR (1) | BRPI0818996A2 (enExample) |
| CA (1) | CA2704022A1 (enExample) |
| ES (1) | ES2378359T3 (enExample) |
| MX (1) | MX2010005754A (enExample) |
| TW (1) | TW200934807A (enExample) |
| WO (1) | WO2009070587A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2703786A1 (en) * | 2007-11-30 | 2009-06-04 | E.I. Du Pont De Nemours And Company | Process to make a poly(trimethylene carbonate) glycol |
| KR20100099713A (ko) * | 2007-11-30 | 2010-09-13 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올 조성물 및 이의 제조 방법 |
| KR101202510B1 (ko) | 2010-10-20 | 2012-11-20 | 삼성메디슨 주식회사 | 위상 배열 프로브에 기초하여 초음파 공간 합성 영상을 제공하는 초음파 시스템 및 방법 |
| WO2025197815A1 (ja) * | 2024-03-19 | 2025-09-25 | 富士フイルム株式会社 | ポリカーボネート化合物の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05339360A (ja) * | 1992-06-12 | 1993-12-21 | Idemitsu Petrochem Co Ltd | ポリカーボネートの製造方法 |
| DE69317818T2 (de) * | 1992-07-13 | 1998-08-06 | Tosoh Corp | Verfahren zur Herstellung von tertiären Alkoholen |
| JPH0710920A (ja) * | 1992-12-01 | 1995-01-13 | Nippon Paint Co Ltd | 環状カーボネート化合物のアルコール性水酸基への開環付加方法 |
| JPH09176152A (ja) * | 1995-12-28 | 1997-07-08 | Sumitomo Bakelite Co Ltd | 環状カーボナート化合物の重合方法 |
| US6451949B2 (en) * | 2000-02-29 | 2002-09-17 | Shell Oil Company | Method for production of poly (trimethylene carbonate) |
| KR20100099713A (ko) * | 2007-11-30 | 2010-09-13 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올 조성물 및 이의 제조 방법 |
| WO2009070578A1 (en) * | 2007-11-30 | 2009-06-04 | E. I. Du Pont De Nemours And Company | Copolymers comprising a trimethylene carbonate and poly(trimethylene ether) glycols |
-
2008
- 2008-11-25 AU AU2008329778A patent/AU2008329778A1/en not_active Abandoned
- 2008-11-25 EP EP08855247A patent/EP2215142B1/en not_active Not-in-force
- 2008-11-25 CN CN2008801183093A patent/CN101878244A/zh active Pending
- 2008-11-25 JP JP2010536129A patent/JP2011505468A/ja active Pending
- 2008-11-25 KR KR1020107014392A patent/KR20100102629A/ko not_active Withdrawn
- 2008-11-25 AT AT08855247T patent/ATE538159T1/de active
- 2008-11-25 CA CA2704022A patent/CA2704022A1/en not_active Abandoned
- 2008-11-25 US US12/277,644 patent/US7790833B2/en not_active Expired - Fee Related
- 2008-11-25 ES ES08855247T patent/ES2378359T3/es active Active
- 2008-11-25 BR BRPI0818996 patent/BRPI0818996A2/pt not_active IP Right Cessation
- 2008-11-25 MX MX2010005754A patent/MX2010005754A/es active IP Right Grant
- 2008-11-25 WO PCT/US2008/084693 patent/WO2009070587A1/en not_active Ceased
- 2008-11-28 TW TW097146471A patent/TW200934807A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008329778A1 (en) | 2009-06-04 |
| KR20100102629A (ko) | 2010-09-24 |
| TW200934807A (en) | 2009-08-16 |
| CA2704022A1 (en) | 2009-06-04 |
| US20090143564A1 (en) | 2009-06-04 |
| WO2009070587A1 (en) | 2009-06-04 |
| ATE538159T1 (de) | 2012-01-15 |
| MX2010005754A (es) | 2010-06-09 |
| BRPI0818996A2 (pt) | 2015-05-05 |
| US7790833B2 (en) | 2010-09-07 |
| CN101878244A (zh) | 2010-11-03 |
| EP2215142B1 (en) | 2011-12-21 |
| EP2215142A1 (en) | 2010-08-11 |
| JP2011505468A (ja) | 2011-02-24 |
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