CN104812800A - 官能化的低聚物 - Google Patents
官能化的低聚物 Download PDFInfo
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- CN104812800A CN104812800A CN201380061830.9A CN201380061830A CN104812800A CN 104812800 A CN104812800 A CN 104812800A CN 201380061830 A CN201380061830 A CN 201380061830A CN 104812800 A CN104812800 A CN 104812800A
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- 239000006260 foam Substances 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 37
- 125000000524 functional group Chemical group 0.000 claims description 32
- -1 acrylic ester Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000013543 active substance Substances 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 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
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 5
- 229940059574 pentaerithrityl Drugs 0.000 claims description 5
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-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
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- 125000004386 diacrylate group Chemical group 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
- 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 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N methylguanidine Chemical compound CNC(N)=N CHJJGSNFBQVOTG-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
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 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
- 239000007795 chemical reaction product Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 33
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- 238000004566 IR spectroscopy Methods 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 4
- 238000006957 Michael reaction Methods 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000005034 decoration Methods 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 239000006227 byproduct Substances 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 1
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Abstract
本公开的实施方式涉及官能化的低聚物。例如，官能化的低聚物可以由式(I)表示：(式I)其中R1为式II的结构：(式II)且R2具有式-CXHYO-，其中n是值为2至6的整数，m是值为2至10的整数，X独立地为值为1至12的整数，Y是值为2至24的整数。
Description
技术领域
本公开的实施方式涉及官能化的低聚物，更特别地，实施方式涉及可用于形成开孔泡沫体的组合物的官能化的低聚物。
背景技术
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，气体形成离散的孔穴，其中离散的孔穴完全由固体材料包围。闭合的孔可以称为非相互连通的。因为离散的孔穴完全由固体材料包围，因此闭合的孔形成硬质材料，例如，硬质泡沫体。另外，闭合的孔有助于防止气体或液体穿过闭孔泡沫体。闭孔泡沫体用于多种应用，尤其例如热绝缘，蒸气绝缘，液体绝缘，接缝填充应用，和冲击保护应用等。
与闭孔泡沫体相反，在开孔泡沫体中，气体孔穴相互连接。开孔可以称为相互连通的。因为开孔泡沫体的气体孔穴不完全由固体材料包围，因此开孔可以形成软质材料，例如，软质泡沫体或粘弹性泡沫体。开孔泡沫体用于多种应用，尤其例如一些绝缘应用，包装应用，汽车装饰，过滤器，和声学应用等。
发明内容
本公开提供式(I)的官能化的低聚物：
(式I)
其中R1为式II的结构：
(式II)
并且R2具有式-CXHYO-，其中n是值为2至6的整数，m是值为2至10的整数，X独立地为值为1至12的整数，Y是值为2至24的整数。R3可以是脂族化合物，芳族化合物，或胺化合物。
本公开提供形成开孔泡沫体的组合物。形成开孔泡沫体的组合物可以包括本申请提供的官能化的低聚物以及多官能迈克尔(Michael)受体。
上述本公开的内容并未意在描述每种公开的实施方式或本公开的每种实践。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
本申请描述了官能化的低聚物。这些官能化的低聚物可以包含在可得到开孔泡沫体的形成开孔泡沫体的组合物中。不同于一些其它泡沫体例如聚氨酯泡沫体，有利地，本申请公开的开孔泡沫体不使用异氰酸酯，异氰酸酯可能是一些应用所不期望的。本申请公开的开孔泡沫体有利地为具有下述性质的泡沫体，所述性质尤其例如为泡沫体密度等，这些性质是一些应用所期望的。本申请公开的开孔泡沫体可以用于多种应用，尤其例如一些绝缘应用，包装应用，汽车装饰应用，过滤器应用，和声学应用等。
本申请所述的官能化的低聚物可以由以下式I表示：
(式I)。
R1可以由以下式II表示：
(式II)
且R2具有式-CXHYO-。如本申请使用，n是值为2至6的整数，m是值为3至10的整数，X是值为1至12的整数，Y是值为2至24的整数。R3可以是脂族化合物，芳族化合物，或胺化合物。应该知道，式(I)官能化的低聚物混合物的n、m、X和Y数值可以是本申请提供的n、m、X和Y的给定范围的有理数。式II中的波浪键表示在该点的具有不同可能性的立体化学的混合物。
例如，由式I表示的官能化的低聚物的R1可以具有式III的结构，
(式III)
例如，其中n的值为3，m的值为2或3，a的值为2或3，X的值为2，Y的值为4。
例如，由式I表示的官能化的低聚物的R1可以具有式IV的结构，
(式IV)
例如，其中n的值为2，m的值为3至4，b的值为3至4，X的值为2，Y的值为4。
也可以称为乙酰乙酸酯低聚物和/或迈克尔供体的官能化的低聚物可以由化学反应例如通过酯交换反应形成。酯交换反应可以包括多元醇和酯。
如本申请使用，"多元醇"是指平均每分子具有大于1.0个羟基的有机分子。可用于形成官能化的低聚物的多种多元醇是可商购的，尤其是，例如IP-625(乙氧基化甘油)，和IP-9001(乙氧基化对苯二甲酸)，两者都购自DowChemical Company，以及其它可商购的多元醇。可用于形成官能化的低聚物的多种多元醇可以通过化学反应例如烷氧基化反应形成。烷氧基化反应可以包括使引发剂(例如水、乙二醇、或丙二醇)与环氧烷烃(例如环氧乙烷、环氧丙烷、或环氧丁烷)在催化剂的存在下反应。用于形成官能化的低聚物的多元醇的实例包括但不限于，乙氧基化甘油，乙氧基化对苯二甲酸，聚(四亚甲基二醇)，聚己酸内酯，聚(环氧丁烷)，聚羟基异丁烯(Krasol多元醇)，蓖麻油(蓖麻酸的甘油三酯)，加氢甲酰化以及还原的种子油的多元醇，乙氧基化芳族酚，对苯二酚二醚乙醇(hydroquinone dietherethanol)，及其组合，以及其它多元醇。
多种酯可以用于形成官能化的低聚物。酯可以是乙酰乙酸酯，氰基乙酸酯，丙二酸酯，或其组合，以及其它酯。酯的实例包括但不限于，3-氧代丁酸叔丁酯；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，以及其组合等。
多元醇和酯可以反应，使得多元醇的羟基与酯的摩尔比为0.5摩尔多元醇的羟基:2.0摩尔酯至2.0摩尔多元醇的羟基:0.5摩尔酯。本申请包括并公开了包括0.5:2.0(多元醇的羟基的摩尔数:酯的摩尔数)至2.0:0.5(多元醇的羟基的摩尔数:酯的摩尔数)的所有单个数值和子范围；例如，多元醇和酯可以反应，使得多元醇的羟基的摩尔数比酯的摩尔数的摩尔比具有上限值2.0:0.5、1.5:0.5、或1.0:0.5至下限值0.5:2.0、1.0:2.0、或1.5:2.0。
可以将多元醇和酯加热至80摄氏度(℃)至200℃的温度，例如，当通过酯交换反应形成官能化的低聚物时。本申请包括并公开了包括80℃至200℃的所有单个数值和子范围；例如，可以将多元醇和酯加热至从下限值80℃、90℃、或115℃至上限值200℃、175℃、或150℃的温度。
可以将多元醇和酯加热至本申请讨论的温度达0.5小时至10小时的时间间隔。本申请包括并公开了包括0.5小时至10小时的所有单个数值和子范围；例如，可以将多元醇和酯加热至本申请讨论的温度达从下限值0.5小时、1.0小时、或1.5小时至上限值10.0小时、9.0小时、或8.0小时的时间间隔。但是，对于一些应用，可以将多元醇和酯加热至本申请讨论的温度达其它时间间隔。
官能化的低聚物的当量可以为200克/当量至5000克/当量。如本申请使用，"当量"定义为官能化的低聚物的数均分子量除以官能化的低聚物的官能度。本申请使用的官能度等于官能化的低聚物中的乙酰乙酸酯基数目，其也等于起始物质中的羟基数目。使用多元醇的数均分子量(由制造商提供或使用羟基滴定测定)以及使用羟基向乙酰乙酸酯转化的转化百分比共同确定官能化的低聚物的数均分子量。使用NMR和IR以确定多元醇中的羟基损失以及官能化的低聚物中乙酰乙酸酯基的定量表征(quantitative appearance)。然后，使用乙酰乙酸酯的分子量确定官能化的低聚物的数均分子量。
本申请包括并公开了包括200克/当量至5000克/当量的所有单个数值和子范围；例如，官能化的低聚物的当量可以为下限值200克/当量、300克/当量、或400克/当量至上限值5000克/当量、4500克/当量、或4000克/当量。对于官能化的低聚物，克/当量可以计算为包含一摩尔迈克尔供体官能团的官能化低聚物的以克计的质量。不受理论限制，针对本公开的目的，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。
正如所述，本申请公开的官能化的低聚物可以用于组合物，例如形成开孔泡沫体的组合物。本申请公开的形成开孔泡沫体的组合物可以包括多官能迈克尔受体。多官能迈克尔受体和官能化的低聚物可以反应以形成开孔泡沫体，例如，通过碳-迈克尔反应形成。虽然不受理论限制，但针对本公开的目的，迈克尔受体官能团是指具有在羰基的α位的脂族碳-碳双键或三键的活化烯烃("烯酮"基团)、或硝基。多官能迈克尔受体可以具有2个迈克尔受体官能团至10个迈克尔受体官能团。例如，多官能迈克尔受体可以具有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。
多官能迈克尔受体可以是丙烯酸酯。本申请使用的“丙烯酸酯”包括丙烯酸酯和(甲基)丙烯酸酯。
丙烯酸酯的实例尤其包括但不限于，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，及其组合等。本公开的一种或多种实施方式提供丙烯酸酯，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，及其组合。
多官能迈克尔受体和官能化的低聚物可以包含在形成开孔泡沫体的组合物中，使得多官能迈克尔受体官能团和官能化的低聚物官能团具有的多官能迈克尔受体官能团摩尔数比官能化的低聚物官能团摩尔数的摩尔比为0.5摩尔多官能迈克尔受体官能团:3.0摩尔官能化的低聚物官能团至3.0摩尔多官能迈克尔受体官能团:0.5摩尔官能化的低聚物官能团。本申请包括并公开了包括0.5:3.0至3.0:0.5的多官能迈克尔受体官能团摩尔数比官能化的低聚物官能团摩尔数的所有单个数值和子范围；例如，形成开孔泡沫体的组合物可以包括多官能迈克尔受体和官能化的低聚物，使得多官能迈克尔受体官能团和官能化的低聚物官能团具有的多官能迈克尔受体官能团摩尔数比官能化的低聚物官能团摩尔数的摩尔比可以为从上限值3.0:0.5、2.8:0.5、或2.6:0.5至下限值0.5:3.0、0.7:3.0、或1.0:3.0。
本申请公开的形成开孔泡沫体的组合物可以包括催化剂，例如，碳-迈克尔反应催化剂。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’-羟乙基二(氨乙基)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-氨丙基)胺，1,2-亚乙基哌嗪，甲基-羟乙基哌嗪，及其组合等。本公开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，及其组合。
催化剂的浓度可以为0.01摩尔催化剂/当量官能化的低聚物官能团至1摩尔催化剂/当量官能化的低聚物官能团。本申请包括并公开了包括0.01摩尔催化剂/当量官能化的低聚物官能团至1摩尔催化剂/当量官能化的低聚物官能团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0.01摩尔、0.02摩尔、或0.03摩尔催化剂/当量官能化的低聚物官能团至上限值1摩尔、0.98摩尔、或0.95摩尔催化剂/当量官能化的低聚物官能团。
本申请公开的形成开孔泡沫体的组合物尤其可以包括发泡剂。发泡剂可以包括戊烷，氟化烃，氯氟化烃，甲酸酯，二氧化碳，及其组合等。本公开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，及其组合。
发泡剂的浓度可以为0.5wt％至50wt％，基于官能化的低聚物和多官能迈克尔受体的总重量。本申请包括并公开了包括基于官能化的低聚物和多官能迈克尔受体的总重量为0.5wt％至50wt％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％，基于官能化的低聚物和多官能迈克尔受体的总重量。
本申请公开的形成开孔泡沫体的组合物可以包括表面活性剂。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活性剂，例如有机硅表面活性剂。聚环氧烷烃例如尤其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Evonik Industries)，B-8462和B8469，DABCOTM DC-198表面活性剂(购自Air Products and Chemicals)，和NiaxTM L-5614表面活性剂(购自Momentive Performance Products)。
表面活性剂的浓度可以为0.1wt％至5.0wt％，基于官能化的低聚物和多官能迈克尔受体的总重量。本申请包括并公开了包括基于官能化的低聚物和多官能迈克尔受体的总重量为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％，基于官能化的低聚物和多官能迈克尔受体的总重量。
形成开孔泡沫体的组合物可以包括一种或多种添加剂。一种或多种添加剂的实例尤其包括但不限于，增塑剂，填料，着色剂，防腐剂，遮味剂(odormasks)，阻燃剂，杀生物剂，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形成开孔泡沫体的组合物中的浓度可以具有不同值。
正如所述，本申请公开的形成开孔泡沫体的组合物可以用于提供开孔泡沫体。开孔泡沫体可以是软质泡沫体或粘弹性泡沫体，这与可以为硬质泡沫体的闭孔泡沫体相反。本申请公开的开孔泡沫体可以通过形成开孔泡沫体的组合物的化学反应例如交联反应形成。
可以将形成开孔泡沫体的组合物加热至0℃至80℃的温度，例如，当使形成开孔泡沫体的组合物交联时。本申请包括并公开了包括0℃至80℃的所有单个数值和子范围；例如，可以将形成开孔泡沫体的组合物加热至从下限值0℃、3℃、或5℃至上限值80℃、60℃、或40℃的温度。
正如所述，使形成开孔泡沫体的组合物交联可以得到开孔泡沫体。泡沫体可以通过多种方法例如ASTM D2856确定为开孔泡沫体。本申请公开的开孔泡沫体用于多种应用，其尤其包括但不限于，一些绝缘应用，包装应用，汽车装饰应用，过滤器应用，和声学应用等。
实施例
在实施例中，使用各种术语和材料的名称，其包括，例如以下：
多元醇(乙氧基化甘油，产品参考IP 625，购自Dow Chemical Company)；多元醇(乙氧基化对苯二甲酸，产品参考IP 9001，购自Dow ChemicalCompany)，乙酰乙酸酯(3-氧代丁酸叔丁酯，购自Sigma-Aldrich)；多官能迈克尔受体(二缩水甘油醚双酚-A的二丙烯酸酯，产品参考CN 120Z，购自Sartomer)，多官能迈克尔受体(二-三羟甲基丙烷四丙烯酸酯，产品参考SR355，购自Sartomer)，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，产品参考B 8469，购自EvonikIndustries)；1,1,1,3,3-五氟丙烷(发泡剂，产品参考HFC 245fa，购自HoneywellCorporation)。
实施例1-官能化的低聚物
官能化的低聚物，即实施例1，如下制备。将IP 625(210克)和3-氧代丁酸叔丁酯(204克)添加到容器中。将容器内容物加热至115℃并保持在115℃，同时搅拌5小时，从而进行酯交换反应并形成实施例1。在酯交换过程中通过蒸馏移除副产物叔丁醇。在5小时之后，将真空施加于容器达10分钟，同时使容器内容物保持在115℃，然后，将真空施加于容器达30分钟，同时使容器内容物保持在85℃。将容器内容物冷却至室温，从而得到285克的实施例1。
红外光谱法用于分析IP 625和实施例1。IP 625红外光谱分析显示在约3090-3670cm-1的吸收，这对应于IP 625的O-H拉伸。实施例1的红外光谱分析显示在约3090-3670cm-1的吸收已经减至低于检出限，表明IP 625发生酯交换并形成实施例1。对于实施例1，R1具有式III的结构：
(式III)
其中n的值为3，m的值为2或3，a的值为2或3，X的值为2，Y的值为4。
实施例2-官能化的低聚物
官能化的低聚物，即实施例2，如下制备。将IP 9001(244克)和3-氧代丁酸叔丁酯(206克)添加到容器中。将容器内容物加热至115℃并保持在115℃，同时搅拌5小时，从而进行酯交换反应并形成实施例2。在酯交换过程中通过蒸馏移除副产物叔丁醇。在5小时之后，将真空施加于容器达10分钟，同时使容器内容物保持在115℃，然后，将真空施加于容器达30分钟，同时使容器内容物保持在85℃。将容器内容物冷却至室温，从而得到312克的实施例2。
红外光谱法用于分析IP 9001和实施例2。IP 9001的红外光谱分析显示在约3110-3650cm-1的吸收，这对应于IP 9001的O-H拉伸。实施例2的红外光谱分析显示在约3110-3650cm-1的吸收已经减至约0，表明IP 9001发生酯交换并形成实施例2。对于实施例2，R1具有式IV的结构：
(式IV)
其中n的值为2，m的值为3至4，b的值为3至4，X的值为2，Y的值为4。
实施例3-形成开孔泡沫体的组合物
形成开孔泡沫体的组合物，即实施例3，如下制备。将CN 120Z(25克)加热至60℃。将经加热的CN 120Z、SR355(50克)、1,1,3,3-四甲基胍(2.3克)和B 8469(1.97克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC 245fa(26.30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，将实施例1(56.51克)添加到容器的内容物中以得到实施例3，然后将实施例3以约2500转/分钟机械搅拌30秒。
实施例4-形成开孔泡沫体的组合物
形成开孔泡沫体的组合物，即实施例4，如下制备。将CN 120Z(25克)加热至60℃。将经加热的CN 120Z、SR355(50克)、1,1,3,3-四甲基胍(2.3克)、和B 8469(2.1克)添加到容器中并以约900转/分钟机械搅拌2分钟。将HFC 245fa(27.98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，将实施例2(64.89克)添加到容器的内容物中以得到实施例4，然后将实施例4以约2500转/分钟机械搅拌30秒。
实施例5-开孔泡沫体
开孔泡沫体，即实施例5，如下制备。在将实施例3机械搅拌之后，将实施例3倒入预加热的(50℃)其中发生固化的铝模具中，从而得到实施例5。
实施例6-开孔泡沫体
开孔泡沫体，即实施例6，如下制备。在将实施例4机械搅拌之后，将实施例4倒入预加热的(50℃)其中发生固化的铝模具中，从而得到实施例5。
实施例5和实施例6的开孔百分比通过ASTM D2856测定并且报告于表1。
表1
| 开孔百分比 | |
| 实施例5 | >90 |
| 实施例6 | >90 |
表1中报告的>90的开孔百分比数值表明，实施例5和实施例6都是开孔泡沫体。
实施例5和实施例6的泡沫体密度通过ASTM D1622测定并报告于表2。
表2
表2中的数据显示，实施例5和实施例6都具有适于一些开孔泡沫体应用的泡沫体密度。
Claims (14)
1.式(I)的官能化的低聚物：
其中R1为式II的结构：
且R2具有式-CXHYO-，其中n是值为2至6的整数，m是值为2至10的整数，X独立地是值为1至12的整数，Y是值为2至24的整数。
2.权利要求1的官能化的低聚物，其中R1具有式III的结构，
其中n的值为3，m的值为2或3，a的值为2或3，X的值为2，Y的值为4。
3.权利要求1的官能化的低聚物，其中R1具有式IV的结构，
其中n的值为2，m的值为3至4，b的值为3至4，X的值为2，Y的值为4。
4.形成开孔泡沫体的组合物，其包含：
前述权利要求任一项的官能化的低聚物；和
多官能迈克尔受体。
5.权利要求4的组合物，其中所述官能化的低聚物的当量为200克/当量至5000克/当量。
6.权利要求4-5任一项的组合物，其中所述多官能迈克尔受体是多官能丙烯酸酯。
7.权利要求6的组合物，其中所述多官能丙烯酸酯选自：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，环己烷二甲醇二丙烯酸酯，及其组合。
8.权利要求4-7任一项的组合物，其中多官能迈克尔受体官能团和官能化的低聚物官能团的摩尔比为0.5:3.0至3.0:0.5的多官能迈克尔受体官能团摩尔数比官能化的低聚物官能团摩尔数。
9.权利要求4-8任一项的组合物，其包括催化剂，所述催化剂的浓度为0.01摩尔催化剂/当量官能化的低聚物官能团至1摩尔催化剂/当量官能化的低聚物官能团。
10.权利要求9的组合物，其中所述催化剂选自：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，及其组合。
11.权利要求4-10任一项的组合物，其包括发泡剂，所述发泡剂的浓度为0.5wt％至50wt％，基于所述官能化的低聚物和所述多官能迈克尔受体的总重量。
12.权利要求11的组合物，其中所述发泡剂选自：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，及其组合。
13.权利要求4-12任一项的组合物，其包括表面活性剂，所述表面活性剂的浓度为0.1wt％至5.0wt％，基于所述官能化的低聚物和所述多官能迈克尔受体的总重量。
14.开孔泡沫体，其为权利要求4-13任一项的形成开孔泡沫体的组合物的反应产物。
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