RU2015115708A - Способ применения углеродного соединения михаэля - Google Patents
Способ применения углеродного соединения михаэля Download PDFInfo
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- RU2015115708A RU2015115708A RU2015115708A RU2015115708A RU2015115708A RU 2015115708 A RU2015115708 A RU 2015115708A RU 2015115708 A RU2015115708 A RU 2015115708A RU 2015115708 A RU2015115708 A RU 2015115708A RU 2015115708 A RU2015115708 A RU 2015115708A
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- multifunctional
- michael
- donor
- acrylate compound
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- 238000000034 method Methods 0.000 title claims abstract 16
- 150000001722 carbon compounds Chemical class 0.000 title claims abstract 9
- -1 acrylate compound Chemical class 0.000 claims abstract 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims abstract 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims abstract 3
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims abstract 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 claims abstract 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- 229960002479 isosorbide Drugs 0.000 claims abstract 2
- 150000002772 monosaccharides Chemical class 0.000 claims abstract 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims 1
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 claims 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims 1
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 claims 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims 1
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 claims 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims 1
- 230000004807 localization Effects 0.000 claims 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- PTXVFWUKFWDHBB-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO.OCC(CO)(CO)CO PTXVFWUKFWDHBB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
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- C09K5/08—Materials not undergoing a change of physical state when used
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
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Abstract
1. Способ использования углеродного соединения Михаэля для уменьшения теплопередачи, включающийлокализацию углеродного соединения Михаэля между теплопередатчиком и теплоприемником, гдеуглеродное соединение Михаэля представляет собой продукт реакции многофункционального акрилатного соединения с многофункциональным донором Михаэля; итеплопередатчик имеет температуру от 100 до 290°С.2. Способ по п. 1, где многофункциональное акрилатное соединение и многофункциональный донор Михаэля вводят в реакцию в мольном отношении от 0,5:3,0 до 3,0:0,5 молей функциональностей многофункционального акрилатного соединения к молям функциональностей многофункционального донора Михаэля.3. Способ по п. 1, где углеродное соединение Михаэля имеет температуру термического разложения от 300 до 450°С.4. Способ по п. 1, где многофункциональный донор Михаэля представляет собой многофункциональное акрилатное соединение, выбранное из группы, включающей триакрилат триметилолпропана, тетраакрилат пентаэритрита, тетраакрилат ди-триметилолпропана, гексаакрилат ди-пентаэритрита, пентаакрилат ди-пентаэритрита, диакрилат диглицидилового простого эфира бисфенола А, этоксилированный триакрилат триметилолпропана, диакрилат трициклодекандиметанола и диакрилат циклогександиметанола или их комбинацию.5. Способ по п. 1, где многофункциональный донор Михаэля выбирают из группы ацетоацетатов, полученных из глицерина, триметилолпропана, этанол-изосорбида, неопентилгликоля, пентаэритрита, диметилолпропана, ди-пентаэритрита, пропоксилированных моносахаридов, триметилолэтана или их комбинации.6. Способ по п. 1, где многофункциональное акрилатное соединение и
Claims (9)
1. Способ использования углеродного соединения Михаэля для уменьшения теплопередачи, включающий
локализацию углеродного соединения Михаэля между теплопередатчиком и теплоприемником, где
углеродное соединение Михаэля представляет собой продукт реакции многофункционального акрилатного соединения с многофункциональным донором Михаэля; и
теплопередатчик имеет температуру от 100 до 290°С.
2. Способ по п. 1, где многофункциональное акрилатное соединение и многофункциональный донор Михаэля вводят в реакцию в мольном отношении от 0,5:3,0 до 3,0:0,5 молей функциональностей многофункционального акрилатного соединения к молям функциональностей многофункционального донора Михаэля.
3. Способ по п. 1, где углеродное соединение Михаэля имеет температуру термического разложения от 300 до 450°С.
4. Способ по п. 1, где многофункциональный донор Михаэля представляет собой многофункциональное акрилатное соединение, выбранное из группы, включающей триакрилат триметилолпропана, тетраакрилат пентаэритрита, тетраакрилат ди-триметилолпропана, гексаакрилат ди-пентаэритрита, пентаакрилат ди-пентаэритрита, диакрилат диглицидилового простого эфира бисфенола А, этоксилированный триакрилат триметилолпропана, диакрилат трициклодекандиметанола и диакрилат циклогександиметанола или их комбинацию.
5. Способ по п. 1, где многофункциональный донор Михаэля выбирают из группы ацетоацетатов, полученных из глицерина, триметилолпропана, этанол-изосорбида, неопентилгликоля, пентаэритрита, диметилолпропана, ди-пентаэритрита, пропоксилированных моносахаридов, триметилолэтана или их комбинации.
6. Способ по п. 1, где многофункциональное акрилатное соединение и многофункциональный донор Михаэля вводят в реакцию в присутствии катализатора, выбранного из группы, включающей 1,1,3,3-тетраметилгуанидин, 1,8-диазабицикло[5,4,0]ундец-7-ен, 1,5-диазабицикло[4,3,0]нон-5-ен, гидроксид тетраметиламмония, гидроксид (2-гидроксиэтил)триметиламмония, карбонат калия, фосфат калия, фенолят калия, фенолят натрия, гидроксид тетраэтиламмония или их комбинацию, где катализатор имеет концентрацию от 0,001 моля катализатора на эквивалент функционализированного донора Михаэля до 1 моля катализатора на эквивалент функционализированного донора Михаэля.
7. Способ по п. 1, где многофункциональное акрилатное соединение и многофункциональный донор Михаэля вводят в реакцию в присутствии газообразующего агента, выбранного из группы, включающей циклопентан, н-пентан, диметилацеталь формальдегида, метилформиат, метилбутан, 1,1,2,2,3-пентафтор-пропан, 1,1,1,3,3-пентафторпропан, 1,1,1,3,3-пентафторбутан, 1,1,1,2,3,4,4,5,5,5-декафторпентан, цис-1,1,1,4,4,4-гексафтор-бут-2-ен, транс-1-хлор-3,3,3-трифторпропен или их комбинацию, где газообразующий агент имеет концентрацию газообразующего агента нижней границы в 0,5 мас.% до верхней границы в 50 мас.% из расчета на общую массу многофункционального донора Михаэля и многофункционального акрилатного соединения.
8. Способ по п. 1, где многофункциональное акрилатное соединение и многофункциональный донор Михаэля вводят в реакцию в присутствии поверхностно-активного вещества, где поверхностно-активное вещество имеет концентрацию от 0,1 до 5,0 мас.% из расчета на общую массу многофункционального донора Михаэля и многофункционального акрилатного соединения.
9. Способ по любому из предыдущих пунктов, где углеродное соединение Михаэля представляет собой закрыто-ячеистую пену.
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| US61/706,360 | 2012-09-27 | ||
| PCT/US2013/062000 WO2014052644A1 (en) | 2012-09-27 | 2013-09-26 | Method of using a carbon-michael compound |
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| CA3006723A1 (en) | 2015-12-02 | 2017-06-08 | Dow Global Technologies Llc | Additive manufactured carbon michael addition articles and method to make them |
| WO2019164900A1 (en) * | 2018-02-21 | 2019-08-29 | Cryovac, Llc | Method and formulation for an isocyanate-free foam using isocyanate-free polyurethane chemistry |
| US11643569B2 (en) | 2018-05-03 | 2023-05-09 | Dow Global Technologies Llc | Method for providing substrate coated with a cured damping coating and coated substrate so provided |
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| US20050081994A1 (en) | 2003-01-02 | 2005-04-21 | Beckley Ronald S. | Methods of using Michael addition compositions |
| EP1593728B1 (en) * | 2004-05-03 | 2012-05-09 | Rohm And Haas Company | Michael addition compositions |
| RU2381835C2 (ru) * | 2004-07-21 | 2010-02-20 | Циба Спешиалти Кемикэлз Холдинг Инк. | Способ фотоактивации и применение катализатора посредством обращенной двустадийной процедуры |
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| EP2900743B1 (en) | 2016-10-26 |
| CN104812816A (zh) | 2015-07-29 |
| BR112015006263A2 (pt) | 2017-07-04 |
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