CN104812816A - 使用碳-迈克尔化合物的方法 - Google Patents
使用碳-迈克尔化合物的方法 Download PDFInfo
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- CN104812816A CN104812816A CN201380061325.4A CN201380061325A CN104812816A CN 104812816 A CN104812816 A CN 104812816A CN 201380061325 A CN201380061325 A CN 201380061325A CN 104812816 A CN104812816 A CN 104812816A
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- michael
- compound
- carbon
- acrylic ester
- polyfunctional acrylic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 20
- -1 acrylate compound Chemical class 0.000 claims abstract description 55
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000006260 foam Substances 0.000 claims description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 229940059574 pentaerithrityl Drugs 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 230000015556 catabolic process Effects 0.000 claims description 9
- 238000006731 degradation reaction Methods 0.000 claims description 9
- 125000004386 diacrylate group Chemical group 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 8
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
- 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 description 3
- 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 claims description 3
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 3
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229940117969 neopentyl glycol Drugs 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 3
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 3
- 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 description 2
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 claims description 2
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(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.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 claims description 2
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 claims description 2
- WAMBUHSSUGGLJO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WAMBUHSSUGGLJO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004604 Blowing Agent Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 claims description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 235000007686 potassium Nutrition 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 2
- 229940093916 potassium phosphate Drugs 0.000 claims description 2
- 235000011009 potassium phosphates Nutrition 0.000 claims description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 78
- 238000010907 mechanical stirring Methods 0.000 description 15
- 238000006957 Michael reaction Methods 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
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- 150000001412 amines Chemical class 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- VVKVJEZDYLJRCJ-UHFFFAOYSA-N OCC(O)CO.OC(CC)(C1=CC=CC=C1)O Chemical compound OCC(O)CO.OC(CC)(C1=CC=CC=C1)O VVKVJEZDYLJRCJ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 3
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
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- 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 description 1
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- 238000007156 chain growth polymerization reaction Methods 0.000 description 1
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Abstract
本申请的实施方式涉及使用碳-迈克尔化合物。例如,使用碳-迈克尔化合物以减少传热的方法可以包括将所述碳-迈克尔化合物置于热量供应体和热量接收体之间,其中所述碳-迈克尔化合物是多官能丙烯酸酯化合物与多官能迈克尔供体的反应产物;以及所述热量供应体的温度为100℃至290℃。
Description
技术领域
本申请的实施方式是使用碳-迈克尔化合物,更特别地,实施方式涉及使用碳-迈克尔化合物以减少传热。
背景技术
也可以称为共轭加成的迈克尔反应用于聚合物合成。例如,迈克尔反应可以提供逐步增长聚合和/或链增长聚合并且可以用于合成线型、接枝、超支化、树状和网络状聚合物。
迈克尔反应包括可称为迈克尔供体的亲核试剂加成到可称为迈克尔受体的亲电试剂。一些迈克尔反应(例如,碳-迈克尔反应)可以得到碳-碳键。
由迈克尔反应形成的一些聚合物已经用于其中期望出现极少或不期望出现含异氰酸酯的化合物的应用。例如,由迈克尔反应形成的聚合物泡沫体已经用于替代由异氰酸酯封端的化合物和异氰酸酯反应性物质形成的一些聚氨酯泡沫体。
发明内容
本申请提供使用碳-迈克尔化合物以减少传热的方法。使用碳-迈克尔化合物以减少传热的方法可以包括将所述碳-迈克尔化合物置于热量供应体和热量接收体之间,其中所述碳-迈克尔化合物是多官能丙烯酸酯化合物与多官能迈克尔供体的反应产物;以及所述热量供应体的温度为100℃至290℃。
上述本发明的内容并未描述每种公开的实施方式或本申请的每种实践。以下说明书更特别地例证说明性的实施方式。在整个申请的几个地方,通过实施例的列举提供了指导,该实施例可以按各种组合使用。在每种情况中,所述清单仅用作代表性组,不应将其理解为详尽清单。
具体实施方式
本申请描述了使用碳-迈克尔化合物的方法。已经出乎意料地发现,本申请讨论的碳-迈克尔化合物可以用于高温应用。已经有利地发现,本申请讨论的碳-迈克尔化合物具有帮助提供它们所适于高温应用的热降解温度。另外,已经发现,本申请讨论的碳-迈克尔化合物在高温(例如,在200℃)的储能模量为30兆帕(MPa)至1000MPa,这是本申请讨论的某些应用所期望的。
如本申请公开,本申请讨论的碳-迈克尔化合物可以用于减少传热。使用碳-迈克尔化合物以减少传热的方法可以包括将所述碳-迈克尔化合物置于热量供应体和热量接收体之间,其中热量供应体的温度为100摄氏度(℃)至290℃。
本申请公开的方法包括碳-迈克尔化合物。碳-迈克尔化合物可以由迈克尔反应形成。正如所述,一些迈克尔反应(例如,碳-迈克尔反应)可以得到碳-碳键。迈克尔反应包括可称为迈克尔供体的亲核试剂加成到可称为迈克尔受体的亲电试剂。迈克尔供体可以是多官能迈克尔供体。本申请使用的"多官能碳-迈克尔供体"是包含一个或多个碳-迈克尔供体官能团并且可以与两个或更多个碳-迈克尔受体官能团反应从而与碳-迈克尔受体官能团的每一个形成碳-碳键的物质。如本申请使用,迈克尔供体官能团是在碳-迈克尔反应催化剂的存在下形成碳负离子的基团,所述碳负离子与迈克尔受体基团的碳-碳双键或三键反应从而与迈克尔受体基团形成碳-碳键。
迈克尔供体可以是乙酰乙酸酯化合物,例如,多官能乙酰乙酸酯化合物。迈克尔受体可以是丙烯酸酯化合物,例如,多官能丙烯酸酯化合物。碳-迈克尔化合物可以是多官能丙烯酸酯化合物与多官能迈克尔供体的反应产物。
正如所述,多官能迈克尔供体可以是丙烯酸酯化合物。本申请使用的“丙烯酸酯”包括丙烯酸酯和(甲基)丙烯酸酯。不希望受限于理论,针对本申请的目的,迈克尔受体官能团是指具有在羰基("烯酮"基团)或硝基的α位的脂族碳-碳双键或三键的活化烯烃。多官能丙烯酸酯化合物可以具有两(2)个迈克尔受体官能团至十(10)个迈克尔受体官能团。例如,多官能丙烯酸酯化合物可以具有2个、3个、4个、5个、6个、7个、8个、9个、或10个迈克尔受体官能团。
多官能丙烯酸酯化合物的实例包括但不限于,双酚A环氧二丙烯酸酯,双酚A甘油(1甘油/苯酚)二丙烯酸酯,1,4-丁二醇二丙烯酸酯,1,6-己二醇二丙烯酸酯,新戊二醇二丙烯酸酯,二甘醇二丙烯酸酯,三甘醇二丙烯酸酯,四甘醇二丙烯酸酯,聚乙二醇二丙烯酸酯,一缩二丙二醇二丙烯酸酯,二缩三丙二醇二丙烯酸酯,环己烷二甲醇二丙烯酸酯,烷氧基化己二醇二丙烯酸酯,烷氧基化环己烷二甲醇二丙烯酸酯,丙氧基化新戊二醇二丙烯酸酯,三羟甲基丙烷三丙烯酸酯,乙氧基化三羟甲基丙烷三丙烯酸酯,丙氧基化三羟甲基丙烷三丙烯酸酯,丙烯酸酯化的聚酯低聚物,双酚A二丙烯酸酯,丙烯酸酯化的双酚A二缩水甘油醚,乙氧基化双酚A二丙烯酸酯,三(2-羟基乙基)异氰脲酸酯三丙烯酸酯,丙烯酸酯化的脂族聚氨酯低聚物,丙烯酸酯化的芳族聚氨酯低聚物,丙烯酸酯化的聚酯低聚物,或其组合等。本申请的一种或多种实施方式提供多官能丙烯酸酯化合物,其选自三羟甲基丙烷三丙烯酸酯,季戊四醇四丙烯酸酯,二-三羟甲基丙烷四丙烯酸酯,二-季戊四醇六丙烯酸酯,二-季戊四醇五丙烯酸酯,二缩水甘油醚双酚-A的二丙烯酸酯,乙氧基化三羟甲基丙烷三丙烯酸酯,三环癸烷二甲醇二丙烯酸酯,和环己烷二甲醇二丙烯酸酯,或其组合。
正如所述,碳-迈克尔化合物可以是多官能丙烯酸酯化合物与多官能迈克尔供体的反应产物。不受理论限制,针对本申请的目的,多官能迈克尔供体的官能团是在碳-迈克尔反应催化剂的存在下形成碳负离子的基团,所述碳负离子与迈克尔受体基团的碳-碳双键或三键反应从而与迈克尔受体基团形成碳-碳键。
多官能迈克尔供体可以是醇的酯,所述醇例如为甲醇、乙醇、叔丁醇、和(甲基)丙烯酸2-羟基乙基酯等。在众多酯中,酯可以是乙酰乙酸酯,氰基乙酸酯,丙二酸酯,或其组合。酯的实例包括但不限于,3-羰基丁酸叔丁酯;多元醇的酯,所述多元醇例如为乙二醇,1,2-丙二醇或1,3-丙二醇,1,4-丁二醇,1,2-丁二醇,1,6-己二醇,新戊二醇,2-甲基-1,3-丙二醇,二甘醇,三甘醇,一缩二丙二醇,二缩三丙二醇,聚(丙二醇),聚(乙二醇),环己烷二甲醇,三羟甲基丙烷,三羟乙基丙烷,季戊四醇,甘油,丙三醇,二季戊四醇,二-三羟甲基丙烷,葡萄糖,异山梨醇,丁基乙基丙二醇;源自聚酯多元醇、聚醚多元醇、或聚酯酰胺多元醇的酯,或其组合等。多官能迈克尔供体可以是多官能乙酰乙酸酯化合物。多官能乙酰乙酸酯化合物选自源自以下物质的乙酰乙酸酯:甘油,三羟甲基丙烷,乙醇异山梨醇,新戊二醇,季戊四醇,二-羟甲基丙烷,二-季戊四醇,二-季戊四醇,丙氧基化单糖,三羟甲基乙烷,或其组合。
多官能丙烯酸酯化合物和多官能迈克尔供体可以按0.5:3.0至3.0:0.5的摩尔比(多官能丙烯酸酯化合物官能团摩尔数比迈克尔供体官能团摩尔数)反应。本申请包括并公开了包括0.5:3.0至3.0:0.5的多官能丙烯酸酯化合物官能团摩尔数比迈克尔供体官能团摩尔数的所有单个数值和子范围;例如,多官能丙烯酸酯化合物和多官能迈克尔供体可以按多官能丙烯酸酯化合物官能团摩尔数比迈克尔供体官能团摩尔数的摩尔比为从上限值3.0:0.5、2.8:0.5、或2.6:0.5到下限值0.5:3.0、0.7:3.0、或1.0:3.0进行反应。
多官能丙烯酸酯化合物和多官能迈克尔供体可以在碳-迈克尔催化剂的存在下反应,例如,当形成碳-迈克尔化合物时。例如,催化剂尤其可以包括叔胺化合物,脒化合物,季铵氢氧化物,碱金属氢氧化物,碱金属醇盐,碱金属乙酰丙酮化物,季铵乙酰丙酮化物等。催化剂的实例包括但不限于,四甲基氢氧化铵,四乙基氢氧化铵,四丁基氢氧化铵,四辛基氢氧化铵,三甲胺,三乙胺,N-甲基吗啉,N-乙基吗啉,N,N-二甲基苄胺,N,N-二甲基乙醇胺,N,N,N',N'-四甲基-1,4-丁二胺,N,N-二甲基哌嗪,1,4-重氮双环-2,2,2-辛烷,二(二甲基氨基乙基)醚,二(2-二甲基氨基乙基)醚,吗啉,4,4'-(氧二-2,1-乙烷二基)二,三亚乙基二胺,五甲基二亚乙基三胺,二甲基环己胺,N-十六烷基N,N-二甲胺,N-椰油基-吗啉,N,N-二甲基氨基甲基N-甲基乙醇胺,N,N,N’-三甲基-N’-羟基乙基二(氨基乙基)醚,N,N-二(3-二甲基氨基丙基)N-异丙醇胺,(N,N-二甲基)氨基-乙氧基乙醇,N,N,N’,N’-四甲基己烷二胺,N,N-二吗啉代二乙基醚,N-甲基咪唑,二甲基氨基丙基二丙醇胺,二(二甲基氨基丙基)氨基-2-丙醇,四甲基氨基二(丙胺),(二甲基(氨基乙氧基乙基))((二甲基胺)乙基)醚,三(二甲基氨基丙基)胺,二环己基甲基胺,二(N,N-二甲基-3-氨基丙基)胺,1,2-亚乙基哌嗪,甲基-羟基乙基哌嗪,或其组合等。本申请的一种或多种实施方式提供催化剂,其选自1,1,3,3-四甲基胍,1,8-二氮杂双环[5.4.0]十一碳-7-烯,1,5-二氮杂双环[4.3.0]壬-5-烯,四甲基氢氧化铵,(2-羟基乙基)三甲基氢氧化铵,碳酸钾,磷酸钾,苯酚钾,苯酚钠,四乙基氢氧化铵,或其组合。
催化剂的浓度可以为0.001摩尔催化剂/当量多官能的迈克尔供体至1摩尔催化剂/当量多官能的迈克尔供体。本申请包括并公开了包括0.001摩尔催化剂/当量多官能的迈克尔供体至1摩尔催化剂/当量多官能的迈克尔供体的所有单个数值和子范围;例如,催化剂的浓度可以为从下限值0.001摩尔、0.002摩尔、或0.003摩尔催化剂/当量多官能的迈克尔供体至上限值1摩尔、0.98摩尔、或0.95摩尔催化剂/当量多官能的迈克尔供体。
多官能丙烯酸酯化合物和多官能迈克尔供体可以在发泡剂的存在下反应,例如,当形成碳-迈克尔化合物时。发泡剂可以包括戊烷,氟化烃,氯氟化烃,甲酸酯,二氧化碳,氢氟烯烃,氢氯氟烯烃,或其组合等。本申请的一种或多种实施方式提供发泡剂,其选自环戊烷,正戊烷,二甲醇缩甲醛,甲酸甲酯,甲基丁烷,1,1,2,2,3-五氟丙烷,1,1,1,3,3-五氟丙烷,1,1,1,3,3-五氟丁烷,1,1,1,2,3,4,4,5,5,5-十氟戊烷,顺式-1,1,1,4,4,4-六氟丁-2-烯,反式-1-氯-3,3,3-三氟丙烯,或其组合。
发泡剂的浓度可以为0.5wt%至50wt%催化剂,基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量。本申请包括并公开了包括基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量为0.5wt%至50wt%催化剂的所有单个数值和子范围;例如,发泡剂的浓度可以为从下限值0.5wt%、1.0wt%、或1.5wt%至上限值50wt%、48wt%、或45wt%发泡剂,基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量。
多官能丙烯酸酯化合物和多官能迈克尔供体可以在表面活性剂的存在下反应,例如,当形成碳-迈克尔化合物时。表面活性剂的实例包括但不限于,基于聚环氧烷烃和有机硅的界面试剂,例如有机硅表面活性剂。聚环氧烷烃例如可以包括环氧乙烷和环氧丙烷的无规和/或嵌段共聚物或环氧乙烷和环氧丁烷的无规和/或嵌段共聚物等。聚环氧烷烃表面活性剂的实例是聚环氧乙烷-共聚-环氧丁烷三嵌段有机表面活性剂,其以商业名称VORASURFTM504出售(购自The Dow Chemical Company)。有机硅表面活性剂的实例包括但不限于,聚硅氧烷/聚醚共聚物例如TegostabTM(购自EvonikIndustries),B-8462和B8469,DABCOTM DC-198表面活性剂(购自AirProducts and Chemicals),和NiaxTM L-5614表面活性剂(购自MomentivePerformance Products)。
表面活性剂的浓度可以为0.1wt%至5.0wt%,基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量。本申请包括并公开了包括基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量为0.1wt%至5.0wt%的所有单个数值和子范围;例如,表面活性剂的浓度可以为从下限值0.1wt%、0.2wt%、或0.3wt%至上限值5.0wt%、4.8wt%、或4.5wt%,基于多官能迈克尔供体和多官能丙烯酸酯化合物的总重量。
碳-迈克尔化合物也可以包括一种或多种添加剂。一种或多种添加剂的实例包括但不限于,增塑剂,填料,着色剂,防腐剂,气味掩饰剂(odor masks),阻燃剂,生物灭杀剂,抗氧化剂,UV稳定剂,抗静电剂,泡沫孔成核剂等。对于不同应用,一种或多种添加剂在碳-迈克尔化合物中的浓度可以具有不同值。
碳-迈克尔化合物的形式可以是泡沫体。例如,碳-迈克尔化合物的形式可以是固体泡沫体,例如,闭孔泡沫体。泡沫体是其中气体分散在液体材料、固体材料、或凝胶材料中的分散体。固体泡沫体包括闭孔泡沫体和开孔泡沫体。
在闭孔泡沫体中,气体形成离散的凹处,其中离散的凹处完全由固体材料包围。闭合的孔可以称为非相互连络的。另外,闭合的孔有助于防止气体或液体穿过闭孔泡沫体。与闭孔泡沫体相反,在开孔泡沫体中,气体凹处相互连接。开孔可以称为相互连络的。
通常,泡沫体可以如下制备:将液体或低熔点前体材料混合,所述液体或低熔点前体材料同时反应并膨胀以形成聚合物泡沫体。碳-迈克尔泡沫体前体材料包括多官能迈克尔供体,迈克尔受体,碳-迈克尔催化剂,发泡剂,表面活性剂和其它泡沫体添加剂。
本申请的实施方式包括将碳-迈克尔化合物置于热量供应体和热量接收体之间。根据多种实施方式,碳-迈克尔化合物可以置于,例如,放置在热量供应体上和/或热量接收体上。碳-迈克尔化合物可以位于热量供应体和热量接收体之间,使得碳-迈克尔化合物接触热量供应体的一部分和/或接触热量接收体的一部分。例如,可以放置碳-迈克尔化合物以包覆,例如,线路,热量供应体的一部分和/或接触热量接收体的一部分。
碳-迈克尔化合物可以位于热量供应体和热量接收体之间,使得碳-迈克尔化合物不接触热量供应体且不接触热量接收体。位于热量供应体和热量接收体之间的碳-迈克尔化合物可以连接于一个或多个基底。例如,基底可以位于碳-迈克尔化合物和热量供应体之间,例如,使得基底接触热量供应体的一部分,和/或基底可以位于碳-迈克尔化合物和热量接收体之间,例如,使得基底接触热量接收体的一部分。对于不同应用,可以使用不同的基底。
碳-迈克尔化合物可以原位形成。碳-迈克尔化合物可以在热量供应体和热量接收体之间形成(例如,放置)。例如,可以将碳-迈克尔化合物的组分(例如,多官能丙烯酸酯化合物,多官能迈克尔供体,以及各自任选的催化剂、发泡剂、表面活性剂、和一种或多种添加剂)施用于热量供应体的一部分和/或热量接收体的一部分,由此碳-迈克尔化合物可以由迈克尔反应形成。类似地,可以将碳-迈克尔化合物的组分施用于基底,例如,接触热量供应体的一部分的基底,和/或接触热量接收体的一部分的基底。针对不同应用,碳-迈克尔化合物的组分可以通过不同方法施用。例如,碳-迈克尔化合物的组分可以尤其通过喷雾、刷涂、辊涂、和/或浸渍等施用方法施用。
正如所述,已经出乎意料地发现,本申请讨论的碳-迈克尔化合物可以用于高温应用,例如,其中碳-迈克尔化合物暴露于100℃至290℃的温度的应用。本申请的实施方式包括将碳-迈克尔化合物置于热量供应体和热量接收体之间,其中热量供应体的温度为100℃至290℃。本申请包括并公开了包括100℃至290℃的所有单个数值和子范围;例如,热量供应体的温度可以为从下限值100℃、150℃、200℃、250℃、或275℃至上限值290℃。例如,热量供应体的温度可以为100℃至290℃,150℃至290℃,200℃至290℃,250℃至290℃,或275℃至290℃。已经有利地发现,本申请讨论的碳-迈克尔化合物具有的热降解温度有助于提高适于高温应用的这些碳-迈克尔化合物。
热量供应体可以是固体物体,液体物体,气体物体,或其组合。热量接收体可以是固体物体,液体物体,气体物体,或其组合。热能可以从热量供应体转移至热量接收体。碳-迈克尔化合物可以减少例如从热量供应体至热量接收体的传热。热量接收体的温度可以为10℃至290℃。本申请包括并公开了包括10℃至290℃的所有单个数值和子范围;例如,热量接收体的温度可以为从下限值10℃、20℃、25℃、50℃、或100℃至上限值290℃、285℃、280、250℃、或200℃。例如,热量接收体的温度可以为10℃至290℃,20℃至285℃,25℃至280℃,50℃至250℃,或100℃至200℃。
热量接收体的温度低于热量供应体的温度。例如,碳-迈克尔化合物可以用作绝缘材料。但是,热量供应体和热量接收体可以处于热平衡,例如,对于某一时间间隔具有相同的温度。碳-迈克尔化合物的优点是,例如用作缓冲物或包装材料,同时在高温(例如,200℃)也是稳定的。
对于其中热量供应体和热量接收体对于某一时间间隔处于热平衡的实施方式,碳-迈克尔化合物可以有利地用作缓冲材料和/或包装材料等应用。
正如所述,已经出乎意料地发现,本申请讨论的碳-迈克尔化合物具有的热降解温度有助于提供可用于高温应用的碳-迈克尔化合物。碳-迈克尔化合物的热降解温度可以为300℃至450℃。本申请包括并公开了包括300℃至450℃的所有单个数值和子范围;例如,碳-迈克尔化合物的热降解温度可以为从下限值300℃、325℃、或350℃至上限值450℃、425℃、或400℃。
对于不同应用,碳-迈克尔化合物可以具有不同厚度。例如,对于一些涂布应用,碳-迈克尔化合物的厚度可以为1微米(μm)至1厘米(cm)。本申请包括并公开了包括1μm至1cm的所有单个数值和子范围;例如,碳-迈克尔化合物的厚度可以为从下限值1μm、3μm、5μm、10μm、或20μm至上限值1cm、0.95cm、0.90cm、0.80cm、或0.75cm。同样,例如,对于一些泡沫绝缘应用,碳-迈克尔化合物的厚度可以为1cm至100cm。本申请包括并公开了包括1cm至100cm的所有单个数值和子范围;例如,碳-迈克尔化合物的厚度可以为从下限值1cm、1.5cm、2cm、3cm、或5cm至上限值100cm、95cm、90cm、80cm、或75cm。
另外,正如所述,碳-迈克尔化合物可以用于泡沫绝缘应用。已经发现,本申请讨论的碳-迈克尔泡沫产品在本申请讨论的高温值具有的储能模量是一些应用所期望的。碳-迈克尔化合物,例如,密度可以为约40kg/m3的泡沫体,在200℃的储能模量可以为30兆帕(MPa)至1000MPa。本申请包括并公开了包括30MPa至1000MPa的所有单个数值和子范围;例如碳-迈克尔化合物在200℃的储能模量可以为从下限值30MPa、40MPa、或50MPa至上限值1000MPa、950MPa、或900MPa。
实施例
在实施例中,使用以下各种术语和材料的名称,包括,例如:
多官能丙烯酸酯化合物(双酚A环氧二丙烯酸酯,产品号CN 120Z,购自Sartomer),多官能丙烯酸酯化合物(二-三羟甲基丙烷四丙烯酸酯,产品号SR355,购自Sartomer),多官能丙烯酸酯化合物(乙氧基化(3)双酚A二丙烯酸酯,产品号SR349,购自Sartomer),多官能丙烯酸酯化合物(芳族聚氨酯丙烯酸酯低聚物,产品号CN997,购自Sartomer),多官能丙烯酸酯化合物(双酚A甘油(1甘油/苯酚)二丙烯酸酯,购自Aldrich),催化剂(1,8-二氮杂双环[5.4.0]十一碳-7-烯,购自Aldrich),催化剂(1,1,3,3-四甲基胍,购自Aldrich),表面活性剂(有机硅表面活性剂,产品号B 8469,购自EvonikIndustries);1,1,1,3,3-五氟丙烷(发泡剂,产品号HFC 245fa,购自HoneywellCorporation),迈克尔供体(多官能乙酰乙酸酯化合物,三羟甲基丙烷三乙酰乙酸酯,购自Lonza),聚醚多元醇(产品号Voranol 360,购自The Dow ChemicalCompany),聚酯多元醇(产品号Stepanpol PS-3152,购自Stepan),胺催化剂(产品号Polycat 5,购自Air Products),胺催化剂(产品号Polycat 8,购自AirProducts),表面活性剂(产品号L-6900,购自Momentive),聚亚甲基聚苯基异氰酸酯(产品号PAPI 27,购自The Dow Chemical Company)。
碳-迈克尔化合物1
碳-迈克尔化合物1如下制备。将双酚A甘油(1甘油/苯酚)二丙烯酸酯(15.00克)加热至60℃。将预加热的双酚A甘油(1甘油/苯酚)二丙烯酸酯、SR355(15.00克)、1,8-二氮杂双环[5.4.0]十一碳-7-烯(1.24克)和B 8469(0.46克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC245fa(8.82克)添加到容器的内容物中,将其以约900转/分钟机械搅拌另外2分钟。中止搅拌,将三羟甲基丙烷三乙酰乙酸酯(14.02克)添加到容器的内容物中,然后将容器内容物以约2500转/分钟机械搅拌30秒,从而得到碳-迈克尔化合物1。
碳-迈克尔化合物2
碳-迈克尔化合物2如下制备。将SR355(15.00克)、SR349(15.00克)、1,8-二氮杂双环[5.4.0]十一碳-7-烯(0.84克)和B 8469(0.45克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC 245fa(8.85克)添加到容器的内容物中,将其以约900转/分钟机械搅拌另外2分钟。中止搅拌,将三羟甲基丙烷三乙酰乙酸酯(14.18克)添加到容器的内容物中,然后将容器内容物以约2500转/分钟机械搅拌30秒,从而得到碳-迈克尔化合物2。
碳-迈克尔化合物3
碳-迈克尔化合物3如下制备。将SR355(15.00克)、CN997(15.00克)、1,8-二氮杂双环[5.4.0]十一碳-7-烯(1.12克)和B 8469(0.53克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC 245fa(9.81克)添加到容器的内容物中,将其以约900转/分钟机械搅拌另外2分钟。中止搅拌,将三羟甲基丙烷三乙酰乙酸酯(18.93克)添加到容器的内容物中,然后将容器内容物以约2500转/分钟机械搅拌30秒,从而得到碳-迈克尔化合物3。
碳-迈克尔化合物4
碳-迈克尔化合物4如下制备。将CN120Z(160.00克)加热至60℃。将预加热的CN120Z、SR355(80.00克)、1,1,3,3-四甲基胍(5.60克)和B 8469(5.48克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC 245fa(73.05克)添加到容器的内容物中,将其以约900转/分钟机械搅拌另外2分钟。中止搅拌,将三羟甲基丙烷三乙酰乙酸酯(125.27克)添加到容器的内容物中,然后将容器内容物以约2500转/分钟机械搅拌30秒,从而得到碳-迈克尔化合物4。
聚氨酯泡沫体
聚氨酯泡沫体如下制备。将Voranol 360(15.63克)、Stepanpol PS-3152(3.91克)、Polycat 5(0.20克)、Polycat 8(0.29克)、和L-6900(0.39克)添加到容器中并以约900转/分钟机械搅拌2分钟。将水(0.39克)和HFC 245fa(5.86克)添加到容器的内容物中,将其以约900转/分钟机械搅拌另外2分钟。中止搅拌,将PAPI 27(24.33克)添加到容器的内容物中,然后将容器内容物以约2500转/分钟机械搅拌约5秒,从而得到聚氨酯泡沫体。
通过TA Instruments型号Q5000TGA在碳-迈克尔化合物1、2、3、和4以及聚氨酯泡沫体上进行热重分析。热重分析在氮气下以10℃/分钟的温度斜升速率从20℃运行至500℃。通过热重分析测定的起始热降解温度报告于表1。
表1
表1中的数据表明,碳-迈克尔化合物1、2、3、和4各自的起始热降解温度大于350℃,这表明碳-迈克尔化合物适于高温应用。表1中的数据表明,碳-迈克尔化合物1、2、3、和4各自具有改善的起始热降解温度,与聚氨酯泡沫体相比。
通过具有压缩室的TA Instruments RSA III流变仪在碳-迈克尔化合物1、2、3、和4以及聚氨酯泡沫体上进行动态力学分析。将碳-迈克尔化合物1、2、3、和4以及聚氨酯泡沫体各自的圆柱形样品(11毫米长,21毫米直径)分别放置于压缩室中。动态力学分析以3℃/分钟的温度斜升速率和1Hz的施加频率从-100℃运行至200℃。通过动态力学分析测定的储能模量报告于表2。
表2
表2中的数据表明,碳-迈克尔化合物1、2、3、和4各自在200℃的储能模量大于30兆帕,这表明碳-迈克尔化合物适于高温应用。表2中的数据表明,碳-迈克尔化合物1、2、3、和4各自具有改善的在200℃的储能模量,与聚氨酯泡沫体相比。
实施例1
实施例1,使用碳-迈克尔化合物以减少传热的方法如下进行。将碳-迈克尔化合物4切割成7英寸X7英寸方形及1英寸厚的样品。将样品的一面放置于预加热至250℃的6英寸×6英寸热板的平坦表面上。将热电偶放在样品的另一面上。通过热电偶监测的温度在2小时内从室温缓慢升至约为65℃的温度稳定平台。通过视觉检查确定,在250℃进行4小时试验后样品的形状和尺寸保持未变。实施例1说明碳-迈克尔化合物适于高温应用。
Claims (9)
1.使用碳-迈克尔化合物来减少传热的方法,包括:
将所述碳-迈克尔化合物置于热量供应体和热量接收体之间,其中
所述碳-迈克尔化合物是多官能丙烯酸酯化合物与多官能迈克尔供体的反应产物;以及
所述热量供应体的温度为100℃至290℃。
2.权利要求1的方法,其中所述多官能丙烯酸酯化合物和所述多官能迈克尔供体按照多官能丙烯酸酯化合物官能团摩尔数比迈克尔供体官能团摩尔数的摩尔比为0.5:3.0至3.0:0.5进行反应。
3.前述权利要求任一项的方法,其中所述碳-迈克尔化合物的热降解温度为300℃至450℃。
4.前述权利要求任一项的方法,其中所述多官能迈克尔供体是选自以下的多官能丙烯酸酯化合物:三羟甲基丙烷三丙烯酸酯,季戊四醇四丙烯酸酯,二-三羟甲基丙烷四丙烯酸酯,二-季戊四醇六丙烯酸酯,二-季戊四醇五丙烯酸酯,二缩水甘油醚双酚-A的二丙烯酸酯,乙氧基化三羟甲基丙烷三丙烯酸酯,三环癸烷二甲醇二丙烯酸酯,环己烷二甲醇二丙烯酸酯,或其组合。
5.前述权利要求任一项的方法,其中所述多官能迈克尔供体选自源自甘油的乙酰乙酸酯,三羟甲基丙烷,乙醇异山梨醇,新戊二醇,季戊四醇,二-羟甲基丙烷,二-季戊四醇,二-季戊四醇,丙氧基化的单糖,三羟甲基乙烷,或其组合。
6.前述权利要求任一项的方法,其中所述多官能丙烯酸酯化合物和所述多官能迈克尔供体在催化剂的存在下反应,所述催化剂选自1,1,3,3-四甲基胍,1,8-二氮杂双环[5.4.0]十一碳-7-烯,1,5-二氮杂双环[4.3.0]壬-5-烯,四甲基氢氧化铵,(2-羟基乙基)三甲基氢氧化铵,碳酸钾,磷酸钾,苯酚钾,苯酚钠,四乙基氢氧化铵,或其组合,其中所述催化剂的浓度为0.001摩尔催化剂/当量官能化的迈克尔供体至1摩尔催化剂/当量官能化的迈克尔供体。
7.前述权利要求任一项的方法,其中所述多官能丙烯酸酯化合物和所述多官能迈克尔供体在发泡剂的存在下反应,所述发泡剂选自环戊烷,正戊烷,二甲醇缩甲醛,甲酸甲酯,甲基丁烷,1,1,2,2,3-五氟丙烷,1,1,1,3,3-五氟丙烷,1,1,1,3,3-五氟丁烷,1,1,1,2,3,4,4,5,5,5-十氟戊烷,顺式-1,1,1,4,4,4-六氟丁-2-烯,反式-1-氯-3,3,3-三氟丙烯,或其组合,其中所述发泡剂的浓度为0.5wt%至50wt%催化剂,基于所述多官能迈克尔供体和所述多官能丙烯酸酯化合物的总重量。
8.前述权利要求任一项的方法,其中所述多官能丙烯酸酯化合物和所述多官能迈克尔供体在表面活性剂的存在下反应,所述表面活性剂的浓度为0.1wt%至5.0wt%,基于所述多官能迈克尔供体和所述多官能丙烯酸酯化合物的总重量。
9.前述权利要求任一项的方法,其中所述碳-迈克尔化合物是闭孔泡沫体。
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CN1757655A (zh) * | 2004-05-03 | 2006-04-12 | 罗姆和哈斯公司 | 迈克尔加成组合物 |
US20060047010A1 (en) * | 2004-09-02 | 2006-03-02 | O'leary Robert J | Pseudo one part foam |
CN101012291A (zh) * | 2006-01-25 | 2007-08-08 | 罗门哈斯公司 | 包封迈克尔加成催化剂 |
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