KR20140098204A - 수소 존재 하의 균일 촉매화 알코올 아민화에 의한 낮은 색 지수를 갖는 폴리알킬렌 폴리아민의 합성 - Google Patents
수소 존재 하의 균일 촉매화 알코올 아민화에 의한 낮은 색 지수를 갖는 폴리알킬렌 폴리아민의 합성 Download PDFInfo
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- KR20140098204A KR20140098204A KR1020147017514A KR20147017514A KR20140098204A KR 20140098204 A KR20140098204 A KR 20140098204A KR 1020147017514 A KR1020147017514 A KR 1020147017514A KR 20147017514 A KR20147017514 A KR 20147017514A KR 20140098204 A KR20140098204 A KR 20140098204A
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- Prior art keywords
- aliphatic
- process according
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- catalyst
- bis
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- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- OFKBTNFPESAEHF-UHFFFAOYSA-N iridium phosphane Chemical class P.[Ir] OFKBTNFPESAEHF-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- NFWOGXPJHBHLPH-UHFFFAOYSA-N nonane-1,2-diamine Chemical compound CCCCCCCC(N)CN NFWOGXPJHBHLPH-UHFFFAOYSA-N 0.000 description 1
- LJZULWUXNKDPCG-UHFFFAOYSA-N nonane-1,2-diol Chemical compound CCCCCCCC(O)CO LJZULWUXNKDPCG-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- VJQGGZWPOMJLTP-UHFFFAOYSA-N octadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCC(O)O VJQGGZWPOMJLTP-UHFFFAOYSA-N 0.000 description 1
- YZJYPXORZOYLHI-UHFFFAOYSA-N octane-1,2-diamine Chemical compound CCCCCCC(N)CN YZJYPXORZOYLHI-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FDUBTTQMOFEVRB-UHFFFAOYSA-N pentadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCC(O)O FDUBTTQMOFEVRB-UHFFFAOYSA-N 0.000 description 1
- ZBPYFGWSQQFVCJ-UHFFFAOYSA-N pentadecane-1,15-diol Chemical compound OCCCCCCCCCCCCCCCO ZBPYFGWSQQFVCJ-UHFFFAOYSA-N 0.000 description 1
- FETBCQJCOOEKPM-UHFFFAOYSA-N pentadecane-1,2-diol Chemical compound CCCCCCCCCCCCCC(O)CO FETBCQJCOOEKPM-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- LPGZAWSMGCIBOF-UHFFFAOYSA-N pentane-1,2-diamine Chemical compound CCCC(N)CN LPGZAWSMGCIBOF-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical class P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- FZHCFNGSGGGXEH-UHFFFAOYSA-N ruthenocene Chemical compound [Ru+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 FZHCFNGSGGGXEH-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 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
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CQTBQILMJBCTRS-UHFFFAOYSA-N tetradecane-1,1-diol Chemical compound CCCCCCCCCCCCCC(O)O CQTBQILMJBCTRS-UHFFFAOYSA-N 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZUDWINGCBFUXNG-UHFFFAOYSA-N tridecane-1,1-diol Chemical compound CCCCCCCCCCCCC(O)O ZUDWINGCBFUXNG-UHFFFAOYSA-N 0.000 description 1
- BPSKTAWBYDTMAN-UHFFFAOYSA-N tridecane-1,13-diamine Chemical compound NCCCCCCCCCCCCCN BPSKTAWBYDTMAN-UHFFFAOYSA-N 0.000 description 1
- IOYXJNDDBALLFR-UHFFFAOYSA-N tridecane-1,2-diol Chemical compound CCCCCCCCCCCC(O)CO IOYXJNDDBALLFR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- QTPYXIZHTKCJDL-UHFFFAOYSA-N undecane-1,2-diamine Chemical compound CCCCCCCCCC(N)CN QTPYXIZHTKCJDL-UHFFFAOYSA-N 0.000 description 1
- BUMVVNKGNPPUME-UHFFFAOYSA-N undecane-1,2-diol Chemical compound CCCCCCCCCC(O)CO BUMVVNKGNPPUME-UHFFFAOYSA-N 0.000 description 1
- KQAYXXFFBQKDEP-UHFFFAOYSA-N undecane-6,6-diamine Chemical compound CCCCCC(N)(N)CCCCC KQAYXXFFBQKDEP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11190831.5 | 2011-11-25 | ||
| EP11190831 | 2011-11-25 | ||
| PCT/EP2012/073051 WO2013076053A1 (de) | 2011-11-25 | 2012-11-20 | Synthese von polyalkylenpolyaminen mit einer geringen farbzahl durch homogen-katalysierte alkohol-aminierung unter anwesenheit von wasserstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140098204A true KR20140098204A (ko) | 2014-08-07 |
Family
ID=47191777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147017514A Withdrawn KR20140098204A (ko) | 2011-11-25 | 2012-11-20 | 수소 존재 하의 균일 촉매화 알코올 아민화에 의한 낮은 색 지수를 갖는 폴리알킬렌 폴리아민의 합성 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2782949A1 (en:Method) |
| JP (1) | JP2014534249A (en:Method) |
| KR (1) | KR20140098204A (en:Method) |
| CN (1) | CN103987757A (en:Method) |
| BR (1) | BR112014012440A2 (en:Method) |
| IN (1) | IN2014CN03935A (en:Method) |
| WO (1) | WO2013076053A1 (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN2014CN03841A (en:Method) * | 2011-11-25 | 2015-09-04 | Basf Se | |
| EP3652160B1 (en) | 2017-07-10 | 2024-09-04 | Nouryon Chemicals International B.V. | Process for manufacturing a mixture of straight-chain and non-straight-chain ethyleneamines |
| CN108531012A (zh) * | 2018-04-30 | 2018-09-14 | 南京市雨花台区绿宝工业设计服务中心 | 一种建筑内墙复合涂料的制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1542359A (fr) * | 1966-11-07 | 1968-10-11 | Basf Ag | Nouvelles polyéthylène amines |
| US3708539A (en) | 1970-02-06 | 1973-01-02 | Union Oil Co | Condensation of ammonia or a primary or secondary amine with an alcohol |
| US4044053A (en) * | 1975-06-02 | 1977-08-23 | Texaco Development Corporation | Preparation of polyalkylene polyamines |
| DE2530042C3 (de) * | 1975-07-04 | 1982-04-22 | Institut neftechimičeskogo sinteza imeni A.V. Topčieva Akademii Nauk SSSR, Moskva | Verfahren zur Herstellung von linearem Polyäthylenimin |
| US4032480A (en) * | 1975-07-11 | 1977-06-28 | David Solomonovich Zhuk | Method of producing linear polyethylenimine |
| EP0034480A3 (en) | 1980-02-14 | 1982-01-13 | Grigg, Ronald Ernest | Alkylation of amines |
| CA1228449A (en) * | 1982-04-30 | 1987-10-20 | William B. Herdle | Preparation of polyalkylene polyamines |
| US4745190A (en) | 1984-07-25 | 1988-05-17 | Air Products And Chemicals, Inc. | Selective synthesis of substituted amines |
| EP0169547B1 (en) * | 1984-07-25 | 1988-09-21 | Air Products And Chemicals, Inc. | Selective syntheses of substituted amines |
| US4617418A (en) * | 1984-11-26 | 1986-10-14 | Air Products And Chemicals, Inc. | Polyalkylene polyamines via vapor phase reaction |
| US4766247A (en) * | 1986-09-26 | 1988-08-23 | Air Products And Chemicals, Inc. | Color reduction of polyamines by mild catalytic hydrogenation |
| JP2508771B2 (ja) * | 1987-12-11 | 1996-06-19 | 東ソー株式会社 | アルキレンアミン類の製造方法 |
| JP2895973B2 (ja) * | 1991-03-05 | 1999-05-31 | 花王株式会社 | 新規第３級アミノアルコール及びその製造方法 |
| DE19545874A1 (de) * | 1995-12-08 | 1997-06-12 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Homopolymerisaten des Ethylenimins |
| WO1997023546A1 (en) * | 1995-12-21 | 1997-07-03 | The Procter & Gamble Company | A process for ethoxylating polyamines |
| BR9706970A (pt) * | 1996-01-08 | 1999-04-06 | Basf Ag | Processo para a preparação de condensados e adutos contendo amino e uso das frações poliméricas de elevado peso molecular |
| EP1268609B1 (fr) * | 2000-02-18 | 2006-05-17 | Centelion | Procede de preparation de polyalkylenimines fonctionnalises, compositions les contenant et leur utilisations |
| US8557343B2 (en) * | 2004-03-19 | 2013-10-15 | The Boeing Company | Activation method |
| CN102666738A (zh) * | 2009-12-03 | 2012-09-12 | 巴斯夫欧洲公司 | 具有正ζ电势的腐蚀防护颜料 |
| WO2011107512A1 (en) * | 2010-03-02 | 2011-09-09 | Basf Se | The use of linear triethylentetramine as curing agent for epoxy resins |
| BR112012030453A2 (pt) * | 2010-05-31 | 2016-08-09 | Basf Se | processo para a preparação de polialquileno-poliaminas, polialquileno-poliamina, polietilenoimina, e , uso de polialquileno-poliaminas |
-
2012
- 2012-11-20 KR KR1020147017514A patent/KR20140098204A/ko not_active Withdrawn
- 2012-11-20 WO PCT/EP2012/073051 patent/WO2013076053A1/de active Application Filing
- 2012-11-20 CN CN201280057369.5A patent/CN103987757A/zh active Pending
- 2012-11-20 BR BR112014012440A patent/BR112014012440A2/pt not_active IP Right Cessation
- 2012-11-20 EP EP12787744.7A patent/EP2782949A1/de not_active Withdrawn
- 2012-11-20 IN IN3935CHN2014 patent/IN2014CN03935A/en unknown
- 2012-11-20 JP JP2014542794A patent/JP2014534249A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2782949A1 (de) | 2014-10-01 |
| BR112014012440A2 (pt) | 2017-06-06 |
| JP2014534249A (ja) | 2014-12-18 |
| CN103987757A (zh) | 2014-08-13 |
| IN2014CN03935A (en:Method) | 2015-09-04 |
| WO2013076053A1 (de) | 2013-05-30 |
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| PA0105 | International application |
Patent event date: 20140625 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |