ES2837861T3 - Composiciones de poliol de policarbonato alifático - Google Patents
Composiciones de poliol de policarbonato alifático Download PDFInfo
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- ES2837861T3 ES2837861T3 ES15717360T ES15717360T ES2837861T3 ES 2837861 T3 ES2837861 T3 ES 2837861T3 ES 15717360 T ES15717360 T ES 15717360T ES 15717360 T ES15717360 T ES 15717360T ES 2837861 T3 ES2837861 T3 ES 2837861T3
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 230000000737 periodic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HAMAGKWXRRTWCJ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-3-one Chemical compound C1=CN=C2OC(=O)C=NC2=C1 HAMAGKWXRRTWCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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- 229920001169 thermoplastic Polymers 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G64/0216—Aliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
-
- 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
- C08G64/42—Chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US201461974500P | 2014-04-03 | 2014-04-03 | |
| PCT/US2015/024299 WO2015154001A1 (en) | 2014-04-03 | 2015-04-03 | Aliphatic polycarbonate polyol compositions |
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| ES2837861T3 true ES2837861T3 (es) | 2021-07-01 |
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| ES15717360T Active ES2837861T3 (es) | 2014-04-03 | 2015-04-03 | Composiciones de poliol de policarbonato alifático |
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| EP (1) | EP3126424B1 (https=) |
| JP (1) | JP6900194B2 (https=) |
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| CN (1) | CN106661215B (https=) |
| ES (1) | ES2837861T3 (https=) |
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| US9738760B2 (en) | 2013-05-01 | 2017-08-22 | Novomer, Inc. | Aliphatic polycarbonate compositions and methods |
| US10053533B1 (en) * | 2017-04-13 | 2018-08-21 | Presidium Usa, Inc. | Oligomeric polyol compositions |
| JP2021522355A (ja) | 2018-04-18 | 2021-08-30 | サウジ アラムコ テクノロジーズ カンパニー | ポリ（アルキレンカーボネート）ポリマーの末端基異性化 |
| WO2020028606A1 (en) | 2018-08-02 | 2020-02-06 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| MA53727A (fr) | 2018-09-24 | 2021-12-29 | Saudi Aramco Tech Co | Copolymères séquencés de polycarbonate et procédés associés |
| CN110105559A (zh) * | 2019-05-16 | 2019-08-09 | 岭南师范学院 | 一步制备交联二氧化碳共聚物的方法 |
| GB202017531D0 (en) | 2020-11-05 | 2020-12-23 | Econic Tech Limited | (poly)ol block copolymer |
| US12195576B2 (en) | 2021-06-23 | 2025-01-14 | Saudi Aramco Technologies Company | Polyol compositions and methods |
| CN113773478B (zh) * | 2021-09-26 | 2022-09-06 | 中国科学院长春应用化学研究所 | 一种聚(碳酸酯-醚)基生物降解聚酯及其制备方法 |
| CN114763431A (zh) * | 2021-12-08 | 2022-07-19 | 山东联欣环保科技有限公司 | 一种抗冲击能力强的复合高分子材料及其制备方法 |
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Family Cites Families (42)
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| US4108814A (en) | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
| US5637739A (en) | 1990-03-21 | 1997-06-10 | Research Corporation Technologies, Inc. | Chiral catalysts and catalytic epoxidation catalyzed thereby |
| US5665890A (en) | 1995-03-14 | 1997-09-09 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| TWI246520B (en) | 1997-04-25 | 2006-01-01 | Mitsui Chemicals Inc | Processes for olefin polymerization |
| US6130340A (en) | 1998-01-13 | 2000-10-10 | President And Fellows Of Harvard College | Asymmetric cycloaddition reactions |
| US6521561B1 (en) | 1998-05-01 | 2003-02-18 | President And Fellows Of Harvard College | Main-group metal based asymmetric catalysts and applications thereof |
| KR100342659B1 (en) | 2000-12-15 | 2002-07-04 | Rstech Co Ltd | Chiral polymer salene catalyst and process for preparing chiral compounds from racemic epoxide using the same |
| US6884750B2 (en) | 2001-06-27 | 2005-04-26 | Rs Tech Corp. | Chiral salen catalyst and methods for the preparation of chiral compounds from racemic epoxides by using new catalyst |
| US6639087B2 (en) | 2001-08-22 | 2003-10-28 | Rhodia Pharma Solutions Inc. | Kinetic resolution method |
| DE10235316A1 (de) | 2002-08-01 | 2004-02-12 | Basf Ag | Katalysator und Verfahren zur Carbonylierung von Oxiranen |
| JP4290414B2 (ja) * | 2002-11-20 | 2009-07-08 | 旭化成ケミカルズ株式会社 | 末端封止ポリカーボネート及びその方法 |
| US7304172B2 (en) | 2004-10-08 | 2007-12-04 | Cornell Research Foundation, Inc. | Polycarbonates made using highly selective catalysts |
| KR100724550B1 (ko) | 2004-12-16 | 2007-06-04 | 주식회사 엘지화학 | 이중 금속 아연 착화합물과 이를 촉매로 사용한폴리카보네이트의 제조 방법 |
| WO2006099162A2 (en) | 2005-03-14 | 2006-09-21 | Georgia Tech Research Corporation | Polymeric salen compounds and methods thereof |
| US8232267B2 (en) | 2006-10-06 | 2012-07-31 | The Trustees Of Princeton University | Porphyrin catalysts and methods of use thereof |
| EP2573126B1 (en) | 2007-05-04 | 2014-09-24 | SK Innovation Co. Ltd. | A process for producing polycarbonates and a coordination complex used therefor |
| JP5505920B2 (ja) * | 2007-05-09 | 2014-05-28 | 学校法人東京理科大学 | ブロック共重合体の製造方法 |
| WO2008150033A1 (ja) | 2007-06-08 | 2008-12-11 | The University Of Tokyo | エポキシドと二酸化炭素との立体選択的交互共重合 |
| EP2096132A1 (en) | 2008-02-26 | 2009-09-02 | Total Petrochemicals Research Feluy | Monomers issued from renewable resources and process for polymerising them |
| US7858729B2 (en) | 2008-05-29 | 2010-12-28 | Novomer, Inc. | Methods of controlling molecular weight distribution of polymers and compositions thereof |
| CA2727959A1 (en) | 2008-07-30 | 2010-02-04 | Sk Energy, Co., Ltd. | Novel coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
| CN103333330A (zh) | 2008-09-08 | 2013-10-02 | 诺沃梅尔公司 | 聚碳酸酯多元醇组合物和方法 |
| CA2639870A1 (en) | 2008-09-29 | 2010-03-29 | Nova Chemicals Corporation | Trimerization |
| US8580911B2 (en) | 2008-11-01 | 2013-11-12 | Novomer, Inc. | Polycarbonate block copolymers |
| JP2010254918A (ja) | 2009-04-28 | 2010-11-11 | Fujifilm Corp | スルホン酸塩基含有化合物を含む混合物およびその製造方法、溶液組成物、ポリウレタン樹脂およびその製造方法、ならびに磁気記録媒体 |
| KR101503745B1 (ko) | 2010-02-25 | 2015-03-19 | 에스케이이노베이션 주식회사 | 나이트레이트 음이온의 이산화탄소/에폭사이드 공중합 촉매 시스템 |
| EP2591036B1 (de) * | 2010-07-05 | 2014-03-26 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von polyolgemischen |
| KR101983006B1 (ko) | 2010-08-27 | 2019-05-29 | 사우디 아람코 테크놀로지스 컴퍼니 | 중합체 조성물 및 방법 |
| KR101963568B1 (ko) | 2010-09-22 | 2019-07-31 | 사우디 아람코 테크놀로지스 컴퍼니 | 치환된 살리실알데하이드 유도체의 합성 |
| EP3584265B1 (en) | 2010-11-23 | 2023-03-15 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions |
| EP2465890A1 (de) * | 2010-12-17 | 2012-06-20 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen mit primären Hydroxyl-Endgruppen und daraus hergestellte Polyurethanpolymere |
| KR101401925B1 (ko) * | 2010-12-28 | 2014-06-02 | 에스케이이노베이션 주식회사 | 열안정성이 개선된 폴리프로필렌 카보네이트의 제조방법 |
| US8952104B2 (en) | 2011-01-06 | 2015-02-10 | Novomer, Inc. | Polymer compositions and methods |
| HUE036462T2 (hu) | 2011-05-09 | 2018-07-30 | Saudi Aramco Tech Co | Polimer készítmények és eljárások |
| IN2014CN01299A (https=) | 2011-07-25 | 2015-04-24 | Novomer Inc | |
| KR20190059988A (ko) | 2011-08-08 | 2019-05-31 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리머 합성용 촉매 및 방법 |
| GB201115565D0 (en) | 2011-09-08 | 2011-10-26 | Imp Innovations Ltd | Method of synthesising polycarbonates in the presence of a bimetallic catalyst and a chain transfer agent |
| WO2013138161A1 (en) | 2012-03-12 | 2013-09-19 | Novomer, Inc. | Polymer compositions and methods |
| EP2838954B1 (en) | 2012-04-16 | 2024-09-18 | Saudi Aramco Technologies Company | Adhesive compositions and methods |
| US20140024795A1 (en) | 2012-04-25 | 2014-01-23 | Novomer, Inc. | Aliphatic polycarbonate polyols containing silyl groups |
| CN105229047B (zh) | 2012-11-07 | 2018-07-20 | 沙特阿美技术公司 | 高强度聚氨酯泡沫组合物及方法 |
| HK1223388A1 (zh) | 2013-05-13 | 2017-07-28 | Saudi Aramco Technologies Company | 含co2的泡沫和相关方法 |
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- 2015-04-03 JP JP2016560502A patent/JP6900194B2/ja active Active
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- 2015-04-03 ES ES15717360T patent/ES2837861T3/es active Active
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- 2015-04-03 EP EP15717360.0A patent/EP3126424B1/en active Active
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| US20170022319A1 (en) | 2017-01-26 |
| WO2015154001A1 (en) | 2015-10-08 |
| EP3126424A1 (en) | 2017-02-08 |
| JP6900194B2 (ja) | 2021-07-07 |
| KR102392235B1 (ko) | 2022-05-02 |
| CN106661215B (zh) | 2020-09-22 |
| JP2017509772A (ja) | 2017-04-06 |
| US10308759B2 (en) | 2019-06-04 |
| EP3126424B1 (en) | 2020-09-30 |
| KR20160141781A (ko) | 2016-12-09 |
| CN106661215A (zh) | 2017-05-10 |
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