CN107995916B - 可固化的苯并噁嗪组合物 - Google Patents
可固化的苯并噁嗪组合物 Download PDFInfo
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- CN107995916B CN107995916B CN201680050558.8A CN201680050558A CN107995916B CN 107995916 B CN107995916 B CN 107995916B CN 201680050558 A CN201680050558 A CN 201680050558A CN 107995916 B CN107995916 B CN 107995916B
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- hydrogen
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 105
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims description 41
- 239000003085 diluting agent Substances 0.000 claims abstract description 37
- 229920001721 polyimide Polymers 0.000 claims abstract description 32
- 239000004642 Polyimide Substances 0.000 claims abstract description 31
- -1 C1-C20Alkyl Chemical group 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000000835 fiber Substances 0.000 claims description 29
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000012456 homogeneous solution Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VNAFWALXWOAPCK-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1h-indene Chemical group C1CC2=CC=CC=C2C1C1=CC=CC=C1 VNAFWALXWOAPCK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 10
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 8
- 239000012745 toughening agent Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
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- WCNSACYQLDNHFD-UHFFFAOYSA-N 4-(1,3,3-trimethyl-1,2-dihydroinden-2-yl)aniline Chemical compound NC1=CC=C(C=C1)C1C(C2=CC=CC=C2C1C)(C)C WCNSACYQLDNHFD-UHFFFAOYSA-N 0.000 claims description 2
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- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims description 2
- GSIWIEKVNXWKLE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carbaldehyde Chemical compound C1C(C=O)CCC2OC21 GSIWIEKVNXWKLE-UHFFFAOYSA-N 0.000 claims description 2
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 claims description 2
- SEQAMYJUOBIYPB-UHFFFAOYSA-N [4-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-4-yl]methanol Chemical compound C1C(CO)(CO)CCC2OC21 SEQAMYJUOBIYPB-UHFFFAOYSA-N 0.000 claims description 2
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000005304 joining Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000005130 benzoxazines Chemical class 0.000 abstract description 16
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- 238000005538 encapsulation Methods 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 38
- 238000001723 curing Methods 0.000 description 17
- 239000011521 glass Substances 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000463 material Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- 150000001412 amines Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241001598984 Bromius obscurus Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- 150000001299 aldehydes Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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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
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供了含有苯并噁嗪、反应性稀释剂和可溶性聚酰亚胺的可固化组合物。可固化组合物,在固化后,使制品具有良好平衡的热、化学和机械性能,并可用于各种应用中,例如用于电子和电气部件的涂层、结构复合材料和封装系统中。
Description
相关申请的交叉引用
不适用。
关于联邦资助的研究或开发的声明
不适用。
技术领域
本发明涉及包含苯并噁嗪、反应性稀释剂和可溶性聚酰亚胺的可固化组合物。可固化组合物可用于各种应用,例如用于粘合剂、密封剂、涂层、结构或非结构复合材料和电子和电气组件的封装系统中。
发明背景
衍生自苯并噁嗪的开环聚合的聚合物与酚树脂、环氧树脂和其他热固性或热塑性树脂在不同的应用中展开竞争,例如在预浸料坯、层合体、印刷线路板(PWB’s)、模塑料、密封剂、烧结粉末、铸塑制品、结构复合材料和电部件中。苯并噁嗪(其通过酚与胺和醛在溶剂存在或不存在下反应来合成)已经表现出在固化后的尺寸稳定性,并且具有良好的电阻和机械阻力、低的收缩率、低的吸水性且具有中到高的玻璃化转变温度。
苯并噁嗪还已经与不同的环氧树脂组合来生产可固化组合物(参见例如美国专利4,607,091(Schreiber)、5,021,484(Schreiber)、5,200,452(Schreiber)和5,443,911(Schreiber))。因为环氧树脂降低了苯并噁嗪的熔融粘度,因此这些共混物已经表现出可用于电气应用中,因为它们能够承受更高的填料负载量,同时仍然保持可加工的粘度。但是,使用这种共混物的一个缺点是通常需要较高的固化温度。此外,虽然这些共混物在固化后表现出高的玻璃化转变温度,但是韧性和刚度通常会有某些程度的牺牲。
最近,增韧剂被加入以改进挠性。例如,WO2014/137717(Wang等人)公开了基于聚砜的增韧剂用于基于苯并噁嗪的组合物的用途;WO2010/031826(Kreiling等人)公开了可固化组合物,其含有苯并噁嗪化合物和酚(优选双酚-A)封端的预聚物增韧剂;EP1639038B1(Lei等人)公开了一种可固化组合物,其含有苯并噁嗪和丙烯腈-丁二烯共聚物增韧剂;WO2009/075746(Taden等)教导了可固化组合物,其包含苯并噁嗪和苯并噁嗪大分子单体增韧剂,该苯并噁嗪大分子单体增韧剂包含至少3个苯并噁嗪环和至少一个脂族、杂脂族、芳脂族、杂脂肪族、芳族或杂芳族软片段;WO2009/075744(Kreiling等)教导了苯并噁嗪基和非苯并噁嗪基增韧添加剂用于苯并噁嗪基体树脂组分的用途;WO2007/064801公开了一种组合物,其含有苯并噁嗪和两种加成增韧剂的组合:第一种由含羟基的化合物、含异氰酸酯的化合物和酚化合物制备;和,第二种由第一加成物和含环氧化合物和第二酚化合物制备;WO2012/015604(Tran)公开了苯并噁嗪组分和酚封端的聚氨酯、聚脲或聚脲-氨基甲酸酯;和WO2012/100980(Cross等人)教导了一种组合物,其包含苯并噁嗪组分、含芳基砜的苯并噁嗪组分和聚醚砜,以获得均匀的可混溶共混物。
尽管技术现状如此,本发明的一个目的在于提供一种改进的基于苯并噁嗪的组合物,其含有增韧剂,所述组合物在固化后能够长时间在高温下以热、机械和物理方式使用,而不牺牲玻璃化转变温度、强度、韧性或水解稳定性性能,因此可用于各种行业(如航空航天、电子和汽车行业)的高温应用。
发明概述
本发明提供了包括苯并噁嗪、反应性稀释剂和可溶性聚酰亚胺的可固化组合物。在一个实施方案中,所述可固化组合物在固化后形成玻璃化转变温度大于180℃的制品。在另一个实施方案中,所述可固化组合物在固化后形成断裂韧性大于200J/m2的制品,在又一个实施方案中,所述可固化组合物在固化后形成干挠曲模量大于4000MPa的制品。
根据本发明的可固化组合物可以用于多种应用中,例如用于涂料、粘合剂、密封剂和结构或非结构复合材料中,因此可用于各种行业,例如航空航天、汽车或电子行业。
发明详述
当在本文出现,则术语“包含/包括”及其派生词并不意在排除任何另外的组分、步骤或程序的存在,无论其是否在此公开。为了避免任何疑义,此处通过使用术语“包含/包括”所要求保护的全部组合物可以包含任何另外的添加剂、助剂或化合物,除非有相反指示。相反,术语“基本由……组成”当出现在本文,则从任何随后限定的范围中排除任何其他组分、步骤或程序,除了对于操作性来说并非必要的那些之外,和术语“由……组成”在使用时排除了没有明确描述或列举的任何组分、步骤或程序。除非另有规定,否则术语“或/或者”指的是所列举的单个以及任意组合的成员。
冠词“一个”和“一种”在此用于表示一种或多于一种(即至少一种)的该冠词的语法宾语。作为例子,“一种苯并噁嗪”表示一种苯并噁嗪或多于一种苯并噁嗪。表述“在一个实施方案中”、“根据一个实施方案”等通常表示该表述之后的具体特征、结构或特性包括在本发明的至少一个实施方案中,并且可以包括在本发明的多于一个实施方案中。重要的是,这种措辞不必然指的是相同的实施方案。如果说明书记载组分或特征“可以”、“能够”,“能”或“可能”包括或具有一定特性,则该具体组分或特征不必须包括或具有该特性。
本发明提供了一种可固化组合物,所述组合物包含苯并噁嗪、反应性稀释剂和可溶性聚酰亚胺。已经令人惊讶地发现,组分的这种组合提供了一种可固化组合物,所述组合物在固化后在几种临界热机械性能如断裂韧性、拉伸和挠曲模量、玻璃化转变温度和水解稳定性方面表现出显着的改善。
根据一个实施方案,可固化组合物包含苯并噁嗪。给组合物赋予机械强度、低吸水性和热固化性的所述苯并噁嗪,可以是任何含有至少一个苯并噁嗪结构部分的可固化单体、低聚物或聚合物。
因此,在一个实施方案中,该苯并噁嗪可以用以下通式(1)表示:
其中b是1-4的整数;每个R独立地是氢、取代的或未取代的C1-C20烷基、取代的或未取代的C2-C20烯基、取代的或未取代的C6-C20芳基、取代的或未取代的C2-C20杂芳基、取代的或未取代的C4-C20碳环基团、取代的或未取代的C2-C20杂环基团或者C3-C8环烷基;每个R1独立地是氢、C1-C20烷基、C2-C20烯基或C6-C20芳基;和Z是直接键(当b=2时)、取代的或未取代的C1-C20烷基、取代的或未取代的C6-C20芳基、取代的或未取代的C2-C20杂芳基、O、S、S=O、O=S=O或C=O。取代基包括但不限于羟基、C1-C20烷基、C2-C10烷氧基、巯基、C3-C8环烷基、C6-C14杂环基团、C6-C14芳基、C6-C14杂芳基、卤素、氰基、硝基、亚硝氮羰基(nitrone)、氨基、酰氨基、酰基、氧酰基、羧基、氨基甲酸酯(carbamate)、磺酰基、磺酰胺和硫酰基。
在式(1)的具体实施方案中,该苯并噁嗪可以用下式(1a)表示:
在另一实施方案中,该苯并噁嗪可以用以下通式(2)表示:
其中Y是C1-C20烷基、C2-C20烯基、或者取代的或未取代的苯基;和R2是氢、卤素、C1-C20烷基或C2-C20烯基。用于苯基的合适的取代基如上所述。
在式(2)的具体实施方案中,该苯并噁嗪可以用下式(2a)表示:
其中R2是氢、C1-C20烷基或C2-C20烯基,其每个用一个或多个O、N、S、C=O、COO和NHC=O和C6-C20芳基任选地取代或间断;和R3是氢、C1-C20烷基或C2-C20烯基,其每个用一个或多个O、N、S、C=O、COOH和NHC=O或C6-C20芳基任选地取代或间隔。
可选地,该苯并噁嗪可以用以下通式表示:
其中p是2;W选自联苯、二苯基甲烷、二苯基异丙烷、二苯基硫、二苯基亚砜、二苯基砜和二苯基酮;和R1定义如上。
在本发明中,可以使用多官能苯并噁嗪的组合、单官能苯并噁嗪的组合,或者一种或多种多官能苯并噁嗪和一种或多种单官能苯并噁嗪的组合。
该苯并噁嗪可商购自几个来源,包括Huntsman Advanced Materials AmericasLLC和Shikoku Chemicals Corporation。
苯并噁嗪也可以通过在除去水的条件下使酚化合物例如双酚A、双酚F、酚酞或硫代二酚与醛例如甲醛和伯胺反应而获得。这在美国专利第5,543,516号中进一步描述,其内容在此处引入作为参考。酚化合物与醛反应物的摩尔比可以为约1:3至1:10,或者约1:4至1:7。在又一个实施方案中,酚化合物与醛反应物的摩尔比可以为约1:4.5至1:5。酚化合物与伯胺反应物的摩尔比可以为约1:1至1:3,或者约1:1.4至1:2.5。在又一个实施方案中,酚化合物与伯胺反应物的摩尔比可以为约1:2.1至1:2.2。
伯胺的例子包括:芳族单胺或二胺、脂族胺、环脂族胺和杂环单胺;例如苯胺,邻-、间-和对-亚苯基二胺,联苯胺,4,4'-二氨基二苯基甲烷,环己基胺,丁基胺,甲基胺,己基胺,烯丙基胺,糠基胺,乙二胺,和丙二胺。所述胺可以在它们的各自的碳部分中用C1-C8烷基或烯丙基来取代。在一个实施方案中,伯胺是具有通式RaNH2的化合物,其中Ra是烯丙基、未取代的或取代的苯基、未取代的或取代的C1-C8烷基或者未取代的或取代的C3-C8环烷基。Ra基团上合适的取代基包括但不限于氨基、C1-C4烷基和烯丙基。在一些实施方案中,1-4个取代基可以存在于Ra基团上。在一个具体实施方案中,Ra是苯基。
根据另一个实施方案,基于可固化组合物的总重量计,苯并噁嗪可以以约40重量%至约90重量%的量包含在所述可固化组合物中。在另一个实施方案中,基于可固化组合物的总重量计,苯并噁嗪可以以约50重量%至约80重量%的量包含在所述可固化组合物中。在又一个实施方案中,基于可固化组合物的总重量计,苯并噁嗪可以以大于约40重量%的量,而在其他实施方案中以大于约50重量%的量,包含在所述可固化组合物中。在另一个实施方案中,基于可固化组合物的总重量计,苯并嗪可以以小于约90重量%的量,而在其他实施方案中以小于约80重量%的量,包含在所述可固化组合物中。
根据另一个实施方案,可固化组合物含有反应性稀释剂。如本文所用,“反应性稀释剂”包括任何完全可溶的、反应性的并且当与苯并噁嗪和可溶性聚酰亚胺组合时能够降低组合物粘度的化合物。
在一个实施方案中,反应性稀释剂是环氧基反应性稀释剂。环氧基反应性稀释剂可以是单环氧化物、二环氧化物或聚环氧化物,还可以是脂族、脂环族或芳族化合物。单环氧化物、二环氧化物或聚环氧化物可以单独使用或彼此混合使用。单环氧化物、二环氧化物或聚环氧化物也可以通过化学手段预固化(例如通过与二醇或二羧酸酸酐反应)。
在另一个实施方案中,环氧基反应性稀释剂可以是缩水甘油基封端的化合物,例如含有直接连接到氧、氮或硫原子上的缩水甘油基或β-甲基缩水甘油基的化合物。这样的环氧基反应性稀释剂包括但不限于聚缩水甘油基和聚(β-甲基缩水甘油基)酯,其通过在碱存在下使每分子含有两个或更多个羧酸基团的物质与表氯醇、甘油二氯丙醇或β-甲基表氯醇反应而获得。聚缩水甘油酯可以衍生自脂族羧酸,例如草酸、琥珀酸、己二酸、癸二酸、或二聚或三聚亚油酸;衍生自脂环族羧酸,例如六氢邻苯二甲酸、4-甲基六氢邻苯二甲酸、四氢邻苯二甲酸和4-甲基四氢邻苯二甲酸;或衍生自芳族羧酸如邻苯二甲酸、间苯二甲酸和对苯二甲酸。
其它可以使用的环氧基反应性稀释剂包括聚缩水甘油基和聚(β-甲基缩水甘油基)醚,其通过在碱性条件下,或替代性的在酸性催化剂存在随后用碱处理,使每分子含有两个或更多个醇羟基或两个或更多个酚羟基的物质与表氯醇、甘油二氯丙醇或β-甲基表氯醇反应获得。这样的聚缩水甘油醚可以衍生自脂族醇,例如乙二醇和聚(氧乙烯)二醇如二甘醇和三甘醇、丙二醇和聚(氧丙烯)二醇、丙-1,2-二醇、丙-1,3-二醇、丁-1,4-二醇、戊-1,5-二醇、己-1,6-二醇、己-2,4,6-三醇、甘油、1,1,1-三羟甲基丙烷和季戊四醇;可以衍生自环脂族醇,例如对环己二醇、1,1-双(羟甲基)环己-3-烯、双(4-羟基环己基)甲烷、1,4-二羟甲基环己烷和2,2-双(4-羟基环己基)-丙烷;或者可以衍生自含有芳香族核的醇,例如N、N-双-(2-羟基乙基)苯胺和4,4'-双(2-羟基乙基氨基)二苯基甲烷。在一个实施方案中,聚缩水甘油醚衍生自每分子含有两个或更多个酚羟基的物质、例如间苯二酚、儿茶酚、对苯二酚、双(4-羟基苯基)甲烷、1,1,2,2-四(4-羟基苯基)乙烷、4,4'-二羟基联苯、双(4-羟基苯基)砜,尤其是酚-醛或甲酚-甲醛酚醛清漆树脂、2,2-双(4-羟基苯基)丙烷(也称为双酚A)和2,2-双(3,5-二溴-4-羟苯基)-丙烷。
可以进一步使用包括聚(N-缩水甘油基)化合物的环氧基反应性稀释剂,例如通过对表氯醇和含有至少两个直接连接到氮上的氢原子的胺(例如苯胺、正丁胺、双(4-氨基苯基)甲烷、双(4-氨基苯基)砜和双(4-甲基氨基苯基)甲烷)的反应产物的脱氯化氢来获得。可以使用的其它聚(N-缩水甘油基)化合物包括异氰脲酸三缩水甘油酯、环状亚烷基脲(例如亚乙基脲和1,3-亚丙基脲)的N,N'-二缩水甘油基衍生物、以及乙内酰脲(例如5,5-二甲基乙内酰脲)的N,N'-二缩水甘油基衍生物。
也可以使用环状和丙烯酸类聚烯烃的环氧化得到的环氧反应性稀释剂,例如乙烯基环己烯二氧化物、柠檬烯二氧化物、二环戊二烯二氧化物、3,4-环氧基二氢二环戊二烯基缩水甘油醚、乙二醇的双(3,4-环氧二氢二环戊二烯基)醚、3,4-环氧基环己基甲基3,4-环氧基环己烷甲酸酯或其6,6'-二甲基衍生物、乙二醇的双(3,4-环氧基环己烷甲酸酯)、3,4-环氧基环己烷甲醛与1,1-双(羟甲基)3,4-环氧基环己烷之间形成的缩醛、双(2,3-环氧基环戊基)醚、丁二烯二环氧化物、或丁二烯与烯属化合物(例如苯乙烯和乙酸乙烯酯)的共聚物、环氧化亚油酸衍生物和环氧化聚丁二烯。
根据另一个实施方案,反应性稀释剂可以是甲基丙烯酸树脂单体或预聚物,或单官能或多官能丙烯酸酯或甲基丙烯酸酯树脂单体。实例包括乙烯基、丙烯酸酯、苯乙烯、二烯、甲基丙烯酸酯、烯丙基、丙烯酰胺、甲基丙烯酰胺、丙烯腈和含残基的甲基丙烯腈及其组合。代表性的例子包括苯乙烯、α-甲基苯乙烯、取代苯乙烯、乙烯基酯、乙烯醚、环己基乙烯醚、N-乙烯基-2-吡咯烷酮、(甲基)丙烯酰胺、N-取代(甲基)丙烯酰胺、(甲基)丙烯酸辛酯、壬基酚乙氧基化(甲基)丙烯酸酯、(甲基)丙烯酸异冰片基酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸2-(2-乙氧基乙氧基)乙酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸β-羧基乙酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸2-羟乙酯、(甲基)丙烯腈、马来酸酐、衣康酸、(甲基)丙烯酸异癸酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸己酯、(甲基)丙烯酸、N-乙烯基己内酰胺、N-乙烯基甲酰胺、(甲基)丙烯酸硬脂酯、羟基官能己内酯(甲基)丙烯酸酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸羟乙酯、(甲基)丙烯酸羟甲酯、(甲基)丙烯酸羟丙酯、(甲基)丙烯酸羟异丙酯、(甲基)丙烯酸羟丁酯、(甲基)丙烯酸羟基异丁酯、(甲基)丙烯酸四氢呋喃酯及其组合。
在一个实施方案中,反应性稀释剂为单官能丙烯酸酯,例如丙烯酸2-(2-氧基)乙酯、丙烯酸2-苯氧乙酯、丙烯酸羟乙酯、其他长链烷基丙烯酸酯、丙烯酸异冰片酯、环状三羟甲基丙烷缩甲醛丙烯酸酯、单官能脂族丙烯酸氨基甲酸酯及其组合。
在另一个实施方案中,反应性稀释剂是聚丙烯酸酯。聚丙烯酸酯反应性稀释剂的例子包括乙二醇二(甲基)丙烯酸酯、己二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、乙氧基化三羟甲基丙烷三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯,季戊四醇三(甲基)丙烯酸酯,季戊四醇四(甲基)丙烯酸酯,三(2-羟基乙基)异氰脲酸酯三丙烯酸酯、双三羟甲基丙烷四(甲基)丙烯酸酯、和烷氧基化多元醇衍生的二丙烯酸酯或聚丙烯酸酯,例如丙氧基化新戊二醇二丙烯酸酯或丙氧基化二醇三丙烯酸酯、新戊二醇二(甲基)丙烯酸酯及其组合。
在又一个实施方案中,反应性稀释剂为二丙烯酸酯,例如1,6-己二醇二丙烯酸酯、1,9-壬二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、三环癸烷二甲醇二丙烯酸酯、环己烷二甲醇二丙烯酸酯、烷氧基化环己烷二丙烯酸酯和三丙二醇二丙烯酸酯。在另一个实施方案中,反应性稀释剂包括丙氧基化新戊二醇二丙烯酸酯和三丙二醇二丙烯酸酯。
在又一个实施方案中,反应性稀释剂可以为烯丙基苯基醚、2-烯丙基苯基醚、2-烯丙基苯酚、烯丙基苯酚酚醛清漆树脂、丁香酚、二烯丙基双酚A或氰尿酸三烯丙酯。
在又一个实施方案中,反应性稀释剂选自烯丙基缩水甘油醚、丙烯酸缩水甘油醚、甲基丙烯酸缩水甘油醚、部分丙烯酸酯化的环氧树脂、部分丙烯酸化的环氧树脂及其混合物。
在一些实施方案中,基于可固化组合物的总重量计,反应性稀释剂可以以约1重量%至约40重量%的量包含在所述可固化组合物中。在另一个实施方案中,基于可固化组合物的总重量计,反应性稀释剂可以以约5重量%至约30重量%的量包含在所述可固化组合物中。在又一个实施方案中,基于可固化组合物的总重量计,反应性稀释剂可以以大于约1重量%的量,并且在其他实施方式中大于约5重量%,包含在所述可固化组合物中。在更进一步的实施方案中,基于可固化组合物的总重量计,反应性稀释剂可以以小于约40重量%的量,并且在又一些实施方案中可以小于约30重量%的量,包含在所述可固化组合物中。
在另一个实施方案中,可固化组合物包含可溶性聚酰亚胺。本发明的可溶性聚酰亚胺衍生自(i)苯基茚满二胺和(ii)苯基茚满二酐和/或二酐。特别地,可溶性聚酰亚胺含有式(4)的重复单元:
其中四个羰基键合到不同的碳原子上并且在彼此的邻位或对位,从而形成五或六元酰亚胺环;Z1是含有至少一个芳香环的四价基团,其中羰基连接到该环上;Z2是二价有机基团,选自芳族、脂族、烷基芳族、脂环族和杂环基团及其组合,并且具有含杂原子的桥连基团的残基(其中桥中的杂原子是氧、硫、氮、硅或磷)。这些可溶性聚酰亚胺进一步描述于美国专利第3,856,752号,其全部内容通过引用并入本文。
在一个实施方案中,可溶性聚酰亚胺含有式(4)的重复单元,其中Z1是式(5)的苯基茚满基团:
其中R4是氢或C1-C5烷基;且
Z2是式(6)的苯基茚满基团:
其中R5是氢或C1-C5烷基,R6、R7、R8和R9各自独立地是氢、卤素或C1-C4烷基。
可溶性聚酰亚胺的苯基茚满二胺组分可以由式(6)的异构体或取代的异构体的任何组合构成。苯基茚满二胺组分可以例如含有0重量%至100重量%的5-氨基-1-(4'-氨基苯基)-1,3,3-三甲基茚满与100重量%至0重量%的6-氨基-1-(4'-氨基苯基)-1,3,3-三甲基茚满的组合。此外,任何式(6)的取代的二氨基异构体可以在0重量%至100重量%的整个范围内取代这些异构体中的一个或两个。这种取代的二氨基异构体的例子是5-氨基-6-甲基-1-(3'-氨基-4'-甲基苯基)-1,3,3-三甲基茚满、5-氨基-1-(4'-氨基-Ar,Ar'-二氯苯基)-Ar,Ar-二氯-1,3,3-三甲基茚满,6-氨基-1-(4'-氨基-Ar',Ar'-二氯苯基)-Ar,Ar-二氯-1,3,3-三甲基茚满、4-氨基-6-甲基-1-(3'-氨基-4'-甲基苯基)-1,3,3-三甲基茚满和Ar-氨基-1-(Ar-氨基-2',4'-二甲基苯基)-1,3,3,4,6-五甲基茚满,其中上述化合物中的前缀Ar和Ar'表示指定取代基在苯环中位置不确定。
在一个实施方案中优选的式(6)的苯基茚满二胺是其中R5是氢或甲基,R6和R7独立地是氢、甲基、氯或溴,并且R8和R9独立地是氢、氯或溴的那些苯基茚满二胺。在另一个实施方案中,R5是氢或甲基,R6和R7独立地是氢、甲基、氯或溴,并且R8和R9独立地是氢、氯或溴,并且氨基在5、6或7位和3'或4'位。在另一个实施方案中,R5是氢或甲基,R6,R7,R8和R9是氢,氨基在5或6位和4'位。
在另一个实施方案中,Z2是具有式(7)的基团:
其中L是共价键、亚甲基、硫、氧或砜;且R11和R12独立地为氢、卤素、C1-C5烷基或具有下式的基团
其中R13是氢、卤素或C1-C5烷基。
在一个实施方案中,苯基茚满二酐是具有式(8)的化合物:
其中R14是氢或C1-C5烷基。这种二酐的例子包括1-(3',4'-二羧基苯基)-1,3,3-三甲基茚满-5,6-二羧酸二酐、1-(3',4'-二羧基苯基)-1,3,3三甲基茚满-6,7-二羧酸二酐、1-(3',4'-二羧基苯基)-3-甲基茚满-5,6-二羧酸二酐和1-(3',4'-二羧基苯基)-3-甲基茚满-6,7-二羧酸二酐。
其它可与苯基茚满二酐结合或单独使用的二酐是由式(9)表示的化合物:
其中四价基团
如上文所定义。
在一个实施方案中,优选芳族二酐,其中每对羰基的碳原子直接连接在Z1基团的邻或对位碳原子上,以提供以下五元或六元环:
可以使用的二酐的具体实例包括2,3,9,10-苝四羧酸二酐、1,4,5,8-萘四羧酸二酐、2,6-二氯萘-1,4,5,8-四羧酸二酐、2,7-二氯萘-1,4,5,8-四羧酸二酐、2,3,6,7-四氯萘-1,4,5,8-四羧酸二酐、菲-1,8,9,10-四羧酸二酐、2,3,3',4'-二苯酮四羧酸二酐、均苯四甲酸二酐、3,3',4,4'-二苯酮四羧酸二酐、2,2',3,3'-二苯酮四羧酸二酐、3,3,4,4'-联苯四羧酸二酐、2,2',3,3'-联苯四羧酸二酐、4,4'-异亚丙基二邻苯二甲酸二酐、3,3'-亚异丙基二邻苯二甲酸二酐、4,4'-氧双邻苯二甲酸二酐、4,4'-磺酰基二邻苯二甲酸二酐、3,3'-氧双邻苯二甲酸二酐、4,4'-亚甲基二邻苯二甲酸二酐、4,4'-硫代二邻苯二甲酸二酐、4,4'-亚乙基二邻苯二甲酸二酐、2,3,6,7-萘四羧酸二酐、1,2,4,5-萘四羧酸二酐、1,2,5,6-萘四羧酸二酐、苯-1,2,3,4-四羧酸二酐、吡嗪-2,3,5,6-四羧酸二酐和噻吩-2,3,4,5-四羧酸二酐。
在一个具体实施方案中,可溶性聚酰亚胺是高分子量化合物,通过使5(6)-氨基-1(4'-氨基苯基)1,1,3-三甲基茚满(BAPI)与二苯酮四羧酸二酐(BTDA)反应而制备,描述于美国专利第3,856,752号中。该可溶性聚酰亚胺可以以商标从HuntsmanAdvanced Materials Americas LLC商购获得,例如5218和9725聚酰亚胺。
根据一个实施方案,基于可固化组合物的总重量计,可溶性聚酰亚胺可以以约0.1重量%至约25重量%的量包含在所述可固化组合物中。在另一个实施方案中,基于可固化组合物的总重量计,可溶性聚酰亚胺可以以约1重量%至约20重量%的量包含在所述可固化组合物中。在更进一步的实施方案中,基于可固化组合物的总重量计,可溶性聚酰亚胺可以以大于约0.1重量%的量,并且在进一步的实施方案中大于约0.5重量%的量,甚至在进一步的实施方案中至少1重量%的量,包含在所述可固化组合物中。在又一个实施方案中,基于可固化组合物的总重量计,可溶性聚酰亚胺可以以小于约25重量%的量,并且在其它实施方案中小于约20重量%的量,甚至在进一步的实施方案中小于约15重量%的量,包含在可所述固化组合物中。
在另一个实施方案中,可固化组合物可以任选含有一种或多种添加剂。这样的添加剂的实例包括但不限于额外的增韧剂、催化剂、增强剂、填料、助粘剂、阻燃剂、触变剂及其混合物。
可以使用的额外增韧剂的实例包括基于丁二烯/丙烯腈共聚物、丁二烯/(甲基)丙烯酸酯、丁二烯/丙烯腈/苯乙烯接枝共聚物(“ABS”)、丁二烯/甲基丙烯酸甲酯/苯乙烯接枝共聚物(“MBS”)、聚(丙烯)的氧化物,胺封端的丁二烯/丙烯腈共聚物(“ATBN”)和羟基封端的聚醚砜(例如可购自Sumitomo Chemical Company的PES 5003P增韧剂,或购自SolvayAdvanced Polymers,LLC的增韧剂),核壳橡胶和聚合物(如PS 1700增韧剂),环氧树脂基质中具有核-壳结构的橡胶颗粒(例如来自Kaneka Corporation MX-120的树脂、来自Wacker Chemie GmbH的树脂),经橡胶改性的环氧树脂(例如环氧树脂和二烯橡胶的环氧封端的加合物或共轭二烯/丁腈橡胶),以及高分子量聚醚酰亚胺(例如产品、Blendex 338产品和SILTEM STM 1500产品)。
可以使用的催化剂的实例包括酚类化合物及其衍生物、强酸如烯酸、阳离子催化剂如金属卤化物、有机金属衍生物、金属卟啉化合物如氯化铝酞菁、甲苯磺酸甲酯、三氟甲磺酸甲酯和三氟甲磺酸以及卤氧化物。在一个实施方案中,催化剂是酚化合物,例如苯酚、邻甲酚、邻-、间-或对-二羟基苯、2,4,6-三硝基苯酚、2,6-二叔丁基对甲酚、2,2'-二羟基联苯酚、双酚A、双酚F、双酚S、4,4-硫代二苯酚等。在另一个实施方案中,催化剂是酸,例如乙酸、丙酸、草酸、己二酸、癸二酸、苯甲酸、硫酸、对甲苯磺酸、磷酸或硫代二丙酸。
可以使用的填料和增强剂的实例包括二氧化硅、预分散在环氧树脂中的二氧化硅纳米粒子、煤焦油、沥青、纺织纤维、玻璃纤维、石棉纤维、硼纤维、碳纤维、矿物硅酸盐、云母、粉状石英、水合氧化铝、膨润土、硅灰石、高岭土、气凝胶或金属粉末(例如铝粉或铁粉)、以及颜料和染料(如炭黑、氧化物颜料和二氧化钛)、轻微微珠(如空心微珠、玻璃微球、碳和聚合物微球)、阻燃剂、触变剂、流动控制剂(如硅酮、蜡和硬脂酸酯(其也可以部分地用作脱模剂))、助粘剂、抗氧化剂和光稳定剂,可控制上述多者的颗粒大小和分布以改变可固化组合物的物理性质和性能。
如果存在的话,基于可固化组合物的总重量计,可将添加剂以约0.1重量%至约40重量%的量加入到所述可固化组合物中。在另外的实施方案中,基于可固化组合物的总重量计,添加剂可以以约1重量%至约30重量%的量,并且在另外的实施方案中以约5重量%至约15重量%的量,加入到所述可固化组合物中。
根据本发明的可固化组合物可以通过已知的方法制备,例如在研磨机或干式混合器中借助于已知的混合单元(例如捏合机、搅拌器、辊)混合苯并噁嗪、反应性稀释剂、可溶性聚酰亚胺和任选的添加剂。由于苯并噁嗪在加热后能够均聚,使得它们对用于熔融和溶解存在的其它添加剂通常所需的高加工温度敏感,所以根据一些实施方案,在加入苯并噁嗪之前,可以首先混合反应性稀释剂和可溶性聚酰亚胺,用于溶解之前存在的任何添加剂。因此,在一个实施方案中,提供了用于生产可固化组合物的方法,其包括(a)将可溶性聚酰亚胺与反应性稀释剂和任选的添加剂混合以产生均匀溶液或分散液;和(b)将苯并噁嗪与均匀溶液或分散液混合以形成可固化组合物。
令人惊讶地发现,本发明的苯并噁嗪、反应性稀释剂和可溶性聚酰亚胺在混合时形成可固化组合物,所述可固化组合物在固化后产生表现出优异的热、机械和物理性质(例如,高玻璃化转变温度(Tg)、高韧性、高机械强度、高水解稳定性和阻燃性)平衡的固化制品。
因此,根据一个具体的实施方案,可固化组合物在固化后提供具有大于约180℃的玻璃化转变温度(通过动态机械分析或“DMA”测定)的制品。在其它实施方案中,可固化组合物在固化后提供具有大于约200℃,且在进一步的实施方案中大于约210℃,并且甚至进一步的实施方案大于约220℃的玻璃化转变温度(通过DMA测定)的制品。
在其他实施方案中,可固化组合物在固化后提供表现出大于约200J/m2,且在进一步的实施方案中大于约225J/m2的断裂韧性G1c(应变能释放的临界速率)的制品。
在又一个实施方案中,所述可固化组合物在固化后提供具有优异的水解稳定性的制品,如下所示:在75℃水中浸泡至少21天后吸水率(即,重量增加)小于3.0%;和/或暴露于沸水约48小时后强度损失小于5%。
可固化组合物可在高温和/或高压条件下固化以形成固化制品。固化可以在一个或两个或更多个阶段中进行,第一个固化阶段在较低温度下进行,然后在较高温度下进行后固化。在一个实施方案中,固化可以在约30℃至300℃的范围内的温度下在一个或多个阶段中进行,在其他实施方案中在约140℃至220℃的范围内进行。固化速率可以为约30分钟到6小时。
如上所述,可固化组合物特别适合用作涂料、粘合剂、密封剂、以及制备增强复合材料(如预浸料坯和纤维束预浸料坯)的基质,并且也可用于注塑或挤出工艺。
因此,在另一个实施方案中,本发明提供了用于电子或电气部件的粘合剂、密封剂、涂覆或封装系统,其包含本发明的可固化组合物。可在其上涂覆包含可固化组合物的涂层、密封剂、粘合剂或封装系统并且可加热固化的合适基材包括:金属,如钢、铝、钛、镁、黄铜、不锈钢、镀锌钢;硅酸盐如玻璃和石英;金属氧化物;混凝土;木材;电子芯片材料,例如半导体芯片材料;或聚合物,例如聚酰亚胺膜和聚碳酸酯。包含可固化组合物的粘合剂、密封剂或涂层可以用于各种应用中,例如在工业或电子应用中。
在另一个实施方案中,本发明提供了包含注入有可固化组合物的纤维束或纤维层的固化产品。
在又一个实施方案中,本公开提供了一种用于生产预浸料坯或纤维束预浸料坯的方法,包括以下步骤:(a)提供纤维束或纤维层;(b)提供本发明的可固化组合物;(c)将纤维或纤维素层和可固化组合物接合以形成预浸料坯或纤维束预浸料坯组件;(d)任选地从预浸料坯或纤维束预浸料坯组件中除去过量的可固化组合物;和(e)将预浸料坯或纤维束预浸料坯组件暴露于足以将可固化组合物注入纤维束或纤维层并形成预浸料坯或纤维束预浸料坯的高温和/或高压条件下。
在一些实施方案中,纤维束或纤维层可以由单向纤维、纺织纤维、短切纤维、无纺纤维或不连续长纤维构成。纤维可以选自玻璃(例如S玻璃、S2玻璃、E玻璃、R玻璃、A玻璃、AR玻璃、C玻璃、D玻璃、ECR玻璃、玻璃丝、短纤维玻璃、T玻璃和锆玻璃)、碳、聚丙烯腈、丙烯酸、芳族聚酰胺、硼、聚亚烷基、石英、聚苯并咪唑、聚醚酮、聚苯硫醚、聚对苯撑苯并二噁唑、碳化硅、酚醛、邻苯二甲酸酯和环烷酸酯。
可固化组合物(以及由其制备的预浸料坯或纤维束预浸料坯)特别适用于航空和汽车应用的复合材料部件的制造和组装、复合材料和金属部件的粘结、夹层结构的芯部和芯部填充和复合材料铺面。
实施例
对比例1
将70克双酚A苯并噁嗪树脂(来自Huntsman Advanced Materials Americas LLC的XU 35610树脂)在100℃下溶解在30克环氧基反应性稀释剂(来自Huntsman AdvancedMaterials Americas LLC的CY-179树脂)中大约30分钟,获得均匀的溶液。
对比例2
如对比例1所述制备均匀溶液,不同的是还加入10克CTBN 1300x8橡胶并混合以获得均匀溶液。
对比例3
如对比例1所述制备均匀溶液,不同的是还加入10克ATBN1300x16橡胶并混合以获得均匀溶液。
实施例4
将5克可溶性聚酰亚胺(9725聚酰亚胺)在130℃下溶于30克环氧基反应性稀释剂(CY-179树脂)中30分钟以获得均匀溶液(“预混物”)。然后将70克双酚A苯并噁嗪树脂(XU35610树脂)在130℃下溶解在所述预混合物中约30分钟,以获得均匀溶液。
实施例5
每种均匀溶液在约130℃的温度下在真空下进一步混合约15-30分钟。然后将溶液转移到含有0.125英寸垫片的预热(150℃)的玻璃模具中,并在180℃下固化2小时,然后在200℃下固化2小时,最后在220℃下固化2小时。使用差示扫描量热法(10℃/分钟的加热速率)和动态机械分析(5℃/分钟加热速率)测试固化制品以确定Tg、起始和储存模量值。另外,将固化制品进行75℃水浸试验21天以测定增重百分比,并将其置于沸水中48小时以测定强度损失:
表1
还根据ASTM D 790测定每种固化制品的挠曲强度和模量,并且根据ASTM D5045-96测定K1c和G1c值:
表2
比较表1中的结果,可以看出,实施例4和5的Tg与对照对比例1的Tg没有明显变化。但是,实施例4的Tg稍好于对比例2和3的Tg,而实施例5的Tg与对比例2和3的Tg大致相同或略好。还可以看出,通过DMA储存模量测量的强度保持率明显优于对比例2和3的强度保持率。当在暴露于48小时的沸水中后,在30℃、121℃和121℃下测试时,证明了这一点。
比较表2中的结果,清楚的是,可溶性聚酰亚胺实施例(实施例4和5)在保持拉伸和挠曲性能上具有比对比例2或3更高的水平。此外,值得注意的是,实施例4和实施例5的挠曲模量保持率比对比例1稍高。另外,实施例4和5的断裂韧性G1c与对比例1相比提高了2倍。
参考表1和2,可以看出,根据本公开的可固化组合物在固化时表现出:1)高韧性,通过大于200J/m2,尤其大于225J/m2的断裂韧性Glc(即应变能释放的临界速率)量度;2)玻璃化转变温度Tg大于180℃,特别是大于200℃;3)高强度,通过在干燥条件下大于4000MPa的干挠曲模量E值以及当在120℃大于80%的干挠曲模量E的保持率量度;和4)优异的水解稳定性,通过小于3.0%的热水浸泡重量吸收率和小于5%的强度损失量度。
虽然已经在上面详细描述了制造和使用本发明的各种实施例,但是应该理解,本发明提供了许多可以在各种各样的特定上下文中体现的可应用的发明概念。这里讨论的具体实施例仅仅是说明制造和使用本发明的具体方式,并不限定本发明的范围。
Claims (14)
2.根据权利要求1所述的可固化组合物,其中所述苯并噁嗪是下式(1)的化合物:
其中b是1至4的整数;每个R独立地为氢、取代或未取代的C1-C20烷基,取代或未取代的C2-C20烯基,取代或未取代的C6-C20芳基,取代或未取代的C2-C20杂芳基,取代或未取代的C4-C20碳环基,取代或未取代的C2-C20杂环基或C3-C8环烷基;每个R1独立地为氢、C1-C20烷基、C2-C20烯基或C6-C20芳基;且当b是1时,Z是取代或未取代的C1-C20烷基、取代或未取代的C6-C20芳基、取代或未取代的C2-C20杂芳基、O、S、S=O、O=S=O或C=O;和当b是2、3、4时,Z是直接键、取代或未取代的C1-C20烷基、取代或未取代的C6-C20芳基、取代或未取代的C2-C20杂芳基、O、S、S=O、O=S=O或C=O。
4.根据权利要求1所述的可固化组合物,其中所述反应性稀释剂是环氧基反应性稀释剂。
5.根据权利要求4所述的可固化组合物,其中所述环氧基反应性稀释剂选自乙烯基环己烯二氧化物、柠檬烯二氧化物、二环戊二烯二氧化物、3,4-环氧基二氢二环戊二烯基缩水甘油醚、乙二醇的双(3,4-环氧二氢二环戊二烯基)醚、3,4-环氧基环己基甲基3,4’-环氧基环己烷甲酸酯、3,4-环氧基环己基甲基3,4’-环氧基环己烷甲酸酯的6,6'-二甲基衍生物、乙二醇的双(3,4-环氧基环己烷甲酸酯)、3,4-环氧基环己烷甲醛与1,1-双(羟甲基)3,4-环氧基环己烷之间形成的缩醛和双(2,3-环氧基环戊基)醚。
6.根据权利要求1所述的可固化组合物,其中所述可溶性聚酰亚胺衍生自5(6)-氨基-1(4'-氨基苯基)1,1,3-三甲基茚满和二苯甲酮四羧酸二酐(BTDA)。
7.根据权利要求1所述的可固化组合物,其还包含增韧剂、催化剂、增强剂、填料、助粘剂、阻燃剂或触变剂中的一种或多种。
8.根据权利要求1所述的可固化组合物,其中所述可固化组合物包含:
(a)50重量%至80重量%的所述苯并噁嗪;
其中重量百分比基于所述可固化组合物的总重量。
9.一种固化制品,其包括权利要求8所述的可固化组合物。
10.根据权利要求9所述的固化制品,其包括以下性能:
(i)断裂韧性G1c大于200J/m2;
(ii)玻璃化转变温度Tg大于180℃;
(iii)干燥条件下干挠曲模量E’大于4000MPa;和
(iv)通过浸入75℃水中至少21天测量的水解稳定性小于3.0%重量增加。
11.一种固化制品,包括注入有权利要求8所述的可固化组合物的纤维束或纤维层。
12.一种用于生产预浸料坯或纤维束预浸料坯的方法,包括以下步骤:(a)提供纤维束或纤维层;(b)提供权利要求1所述的可固化组合物;(c)将所述纤维束或纤维层和所述可固化组合物接合以形成预浸料坯或纤维束预浸料坯组件;(d)任选地从所述预浸料坯或纤维束预浸料坯组件中除去过量的可固化组合物;和(e)将所述预浸料坯或纤维束预浸料坯组件暴露于足以将所述可固化组合物注入纤维束或纤维层并形成预浸料坯或纤维束预浸料坯的高温和/或高压条件下。
13.一种制备权利要求1的可固化组合物的方法,包括(a)将衍生自(ⅰ)苯基茚满二胺和(ii)苯基茚满二酐和/或二酐的可溶性聚酰亚胺与反应性稀释剂和任选的添加剂混合以产生均匀溶液或分散液;(b)将苯并噁嗪与所述均匀溶液或分散液混合以形成所述可固化组合物。
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CA2993604A1 (en) | 2017-01-26 |
TW201716457A (zh) | 2017-05-16 |
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CN107995916A (zh) | 2018-05-04 |
AU2016296886A1 (en) | 2018-02-01 |
BR112018001264B1 (pt) | 2022-04-19 |
ES2962263T3 (es) | 2024-03-18 |
US20180186730A1 (en) | 2018-07-05 |
EP3325533A4 (en) | 2019-03-27 |
EP3325533A1 (en) | 2018-05-30 |
RU2018106457A (ru) | 2019-08-26 |
BR112018001264A2 (pt) | 2018-09-11 |
MX2018000762A (es) | 2018-05-15 |
RU2748127C2 (ru) | 2021-05-19 |
JP2018522984A (ja) | 2018-08-16 |
RU2018106457A3 (zh) | 2019-12-30 |
TWI737623B (zh) | 2021-09-01 |
EP3325533B1 (en) | 2023-09-13 |
KR102609660B1 (ko) | 2023-12-06 |
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