CN116438222A - 阳离子环氧组合物 - Google Patents
阳离子环氧组合物 Download PDFInfo
- Publication number
- CN116438222A CN116438222A CN202180076989.2A CN202180076989A CN116438222A CN 116438222 A CN116438222 A CN 116438222A CN 202180076989 A CN202180076989 A CN 202180076989A CN 116438222 A CN116438222 A CN 116438222A
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- Prior art keywords
- epoxy
- salts
- composition
- epoxy composition
- present
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 239000004593 Epoxy Substances 0.000 title claims abstract description 64
- 125000002091 cationic group Chemical group 0.000 title description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims abstract description 11
- 239000000853 adhesive Substances 0.000 claims abstract description 9
- 230000001070 adhesive effect Effects 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 23
- -1 chalk Substances 0.000 claims description 22
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- 239000011324 bead Substances 0.000 claims description 3
- 239000000440 bentonite Substances 0.000 claims description 3
- 229910000278 bentonite Inorganic materials 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 3
- 229910021485 fumed silica Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 3
- 239000013615 primer Substances 0.000 claims description 3
- 239000002987 primer (paints) Substances 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 239000010456 wollastonite Substances 0.000 claims description 3
- 229910052882 wollastonite Inorganic materials 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001887 tin oxide Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims 1
- 239000012745 toughening agent Substances 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 11
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 10
- 239000004332 silver Substances 0.000 description 10
- 229910052709 silver Inorganic materials 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 239000002318 adhesion promoter Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 239000011133 lead Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000005410 aryl sulfonium group Chemical group 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 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 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000011231 conductive filler Substances 0.000 description 4
- 229940040102 levulinic acid Drugs 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229920006332 epoxy adhesive Polymers 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002470 thermal conductor Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- QOTQFLOTGBBMEX-UHFFFAOYSA-N alpha-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 125000005520 diaryliodonium group Chemical group 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
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- 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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- 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
- C08G59/20—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 epoxy compounds used
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Abstract
本发明涉及环氧组合物，该组合物包含：a)脂环族环氧树脂；b)固化剂；和c)具有结构(I)的生物基环氧化合物。根据本发明的组合物可用作结构粘合剂、涂料和底漆。
Description
技术领域
本发明涉及环氧组合物，该组合物包含：a)脂环族环氧树脂；b)固化剂；和c)具有结构I的生物基(bio-based)环氧化合物：
背景技术
粘合剂粘合和聚合物涂料通常用于制成品的组装和整理(finishing)中。它们被用来代替机械紧固件(例如，螺钉、螺栓和铆钉)，以提供机械加工成本降低且制造过程中的适应性提高的粘合。粘合剂粘合均匀地分布应力，降低疲劳的可能性并密封接合处防止腐蚀性物质(species)进入。
环氧粘合剂主要由环氧单体和低聚物以及基于环氧树脂的反应性稀释剂组成。持续需要具有新技术特性的新化学品。例如，需要低气味和低蒸汽压的单体以改善生产线和最终使用者的健康和安全性。
这些环氧单体和低聚物以及基于环氧树脂的反应性稀释剂传统上使用基于汽油的(petrol-based)原料制备。为了增加可持续性，环氧粘合剂的最终使用者现在要求产品具有增加的生物基含量而不损害性能。
因此，需要包含由增加量的生物基原料获得的新化学品的环氧粘合剂而不损失所需的物理特性和性能。
发明内容
本发明涉及环氧组合物，该组合物包含：a)脂环族环氧树脂；b)固化剂；和c)具有结构I的生物基环氧化合物：
本发明涵盖根据本发明的环氧组合物的固化产物。
本发明涉及根据本发明的环氧组合物用作结构粘合剂、涂料或底漆的用途。
具体实施方式
在以下段落中，更详细地描述了本发明。如此描述的每个方面可以与任何一个或多个其它方面结合，除非清楚地相反指出。特别是，被作为优选的或有利的指出的任何特征可以与被作为优选的或有利的指出的任何一个或多个其它特征结合。
在本发明的上下文中，所用术语应根据以下定义解释，除非上下文另外指出。
如本文中所用的，单数形式“一种(a或an)”和“所述或该(the)”既包括单数个指代对象又包括复数个指代对象，除非上下文清楚地另外指出。
本文中所用的术语“包含”、“含”和“包括”与“含有”同义，为包含性的或开放式的且不排除另外的未列举的成员、元素或方法步骤。
如本文中所用的，术语“由……组成”不包括未具体指定的任何元素、成分、成员或方法步骤。
对数值端点的列举包括归入相应范围内的所有数字和小数以及所列举的端点。
本文中提及的所有百分比、份数、比例等均基于重量计，除非另外指出。
当量、浓度或者其它值或参数以范围、优选范围、或者优选上限值和优选下限值的形式表述时，应理解为具体公开了通过将任何上限值或优选上限值与任何下限值或优选下限值组合而获得的任何范围，而不考虑所获得的范围是否在上下文中被明确提及。
本说明书中引用的所有参考文献的全部内容在此均通过援引加入的方式纳入本文。
除非另外定义，在公开本发明中使用的所有术语(包括技术术语和科学术语)均具有本发明所属领域的普通技术人员所通常理解的含义。通过进一步指导，包括术语定义以更好地理解本发明的教导。
本发明涉及环氧组合物，该组合物包含：a)脂环族环氧树脂；b)固化剂；和c)具有结构I的生物基环氧化合物：
生物基环氧化合物I优选为β-异构体。
环氧化合物I由乙酰丙酸(LA)合成，如以下方案1至3中所示例说明。
下面的方案1示例说明了由乙酰丙酸(LA)通过反应蒸馏合成α-当归内酯(α-AL)。
由α-AL获得β-当归内酯(β-AL)的路线在下面的方案2中示例说明。将α-AL通过在不使用溶剂的情况下使用三乙胺作为催化剂于100℃下异构化为β-AL。一小时后达到β-AL：α-AL—80：20的混合物。已经发现，增加反应时间不会产生更高的β-AL含量，因为内酯的二聚是竞争性副反应。β-AL可以高达37％的收率获得。
下面的方案3示例说明了如何通过使用含氢氧化四烃胺(Triton B)作为碱和相转移剂(phase transfer agent)的在吡啶中的NaOCl或在THF中的H2O2而氧化β-AL来合成环氧化合物I。
根据ASTM D6866测定，具有结构I的生物基环氧化合物优选由100％生物基碳原子组成。
基于组合物的总重量，具有结构I的生物基环氧化合物可以1至80重量％、优选2至65重量％、更优选3至45重量％且甚至更优选4至30重量％的量存在于根据本发明的组合物中。
申请人发现这些量是优选的，因为高于80％的量可能会导致高放热反应，这会缩短适用期。此外，较高的量可能会导致(用作增韧剂的)无机填料的沉降。低于1％的量可能无法提供所需的技术效果。
申请人发现，将具有结构I的生物基环氧化合物添加到环氧基粘合剂中将提供低粘度，这对于润湿以及更容易通过分配和泵送来施用而言是理想的。此外，低粘度为配制物以可能使用填料和高粘性树脂等成分的形式提供了更大的灵活性。实施例部分中的技术数据表明，使用具有结构I的生物基环氧化合物提供了增加的柔韧性(拉伸试验)，同时保持了动态力学分析中的Tg，这对于抗冲击性是有利的。此外，具有结构I的生物基环氧化合物使得能够快速固化并提高耐洗去性。
根据本发明的环氧组合物包含脂环族环氧树脂。优选地，所述脂环族环氧树脂选自
以及它们的混合物。
非限制性的市售可得实例是来自Daicel的Celloxide 2021、来自Huntsman的Araldite CY 170BD和来自Achiewell的CER 4221。
基于组合物的总重量，脂环族环氧树脂可以10至98重量％、优选12至85重量％、更优选15至80重量％且甚至更优选15至60重量％的量存在于根据本发明的环氧组合物中。
根据本发明的环氧组合物可以包含与脂环族环氧树脂结合使用的另外的树脂。
适合用于本发明中的另外的树脂是例如脂肪族环氧树脂、芳香族环氧树脂、氧杂环丁烷树脂、乙烯基醚树脂及它们的混合物。
基于组合物的总重量，另外的树脂可以1至60重量％、优选10至50重量％、更优选20至30重量％的量存在于根据本发明的环氧组合物中。
根据本发明的组合物包含固化剂，其优选为阳离子固化剂。优选地，所述固化剂选自铵盐、吡啶盐、咪唑鎓盐、胍鎓盐(guadinium salt)、噁唑鎓盐(oxazolium salt)、噻唑鎓盐(thiazolium salt)、碘鎓盐(iodinium salt)、锍盐和磷鎓盐以及它们的混合物。
尤其可以使用硬阳离子非亲核阴离子固化剂。这种固化剂的实例包括锂和周期表第II族金属的盐、以及非亲核酸。这种非亲核性酸具有当以10重量％的水溶液测量时小于1.0的pH。第II族金属盐的实例包括钙和镁。非亲核酸的实例包括高氯酸、氟硼酸、氟砷酸、氟锑酸和氟磷酸。
适合用于本发明中的固化剂的其它非限制性实例有：金属氟硼酸盐；双(全氟烷基磺酰基)甲烷金属盐；芳基重氮化合物；芳香族碘鎓络盐(complex salt)；芳基碘鎓盐；Ia族元素的芳香族鎓盐；Va族元素的芳香族鎓盐；IIIa-Va族元素的二羰基螯合物；VIb族元素的鎓盐，其为MF6阴离子(其中M选自磷、锑和砷)芳基锍盐形式；芳香族锍络盐；双(4-(二苯基锍)-苯基)硫醚-双-六氟金属盐(bis(4-(diphenylsulfonio)-phenyl)sulfide-bis-hexafluorometallic salt)，例如磷酸盐、砷酸盐和锑酸盐；II、V和VI族元素的芳基锍络盐；II、V和VI族元素的含卤素的络合离子的芳香族锍或碘鎓盐，II族的芳香族鎓盐；VI族的芳香族鎓盐；芳基锍盐；芳基锍络盐，例如芳基锍六氟磷酸盐和芳基锍六氟锑酸盐；芳香族碘鎓盐，例如二芳基碘鎓六氟锑酸盐；四氟硼酸锂；四氟硼酸钙(calcium di-tetrafluoroborate)；四氟硼酸镁(magnesium di-tetrafluoroborate)；六氟磷酸锂；六氟磷酸钙(calcium di-hexaflourophosphate)；六氟磷酸镁(magnesium di-hexaflourophosphate)；六氟锑酸锂；六氟砷酸锂；镧系元素三氟甲磺酸盐；三氟甲磺酸镧；三氟甲磺酸镱；三甲氧基环硼氧烷；三甲氧基环硼氧烷-乙酰丙酮铝；胺-三卤化硼络合物；季铵盐；季鏻盐；三芳基锍盐；二芳基碘鎓盐；重氮盐；三烷氧基环硼氧烷固化剂；三氟化硼；三氟化硼-醚化物；三氧化硫(及其水解产物)；甲磺酸。
注意，阳离子固化剂可以包含一种上述盐、两种上述盐的混合物、或者两种或更多种上述盐的混合物。
固化剂的非限制性市售可得实例有：来自King Industries的K-Pure CXC-1612和CXC 1821，来自Adeka的SP-150、SP-170和SP-171，来自BASF的Irgacure 250、270和PAG290。
基于组合物的总重量，固化剂可以以0.01至15重量％、优选0.1至10重量％、更优选0.2至10重量％且甚至更优选0.25至5重量％的量存在于根据本发明的环氧组合物中。
申请人发现，这些含量水平提供了理想的固化；当固化剂的量太高时，会导致未固化的和柔软的网络以及偶尔的胺泄漏(有毒的和难闻的气味)，而太低的量会导致类似的结果，但是具有未反应的环氧基团。
根据本发明的环氧组合物可以进一步包含无机填料。
优选地，所述无机填料选自二氧化硅、气相法白炭黑、硅藻土、氧化铝、氧化锌、氧化铁、氧化镁、氧化锡、氧化钛、氢氧化镁、氢氧化铝、碳酸镁、硫酸钡、石膏、硅酸钙、滑石、玻璃珠、绢云母活化白土(sericite activated white earth)、膨润土、氮化铝、氮化硅、二氢氧化镁(magnesia dihydroxide)、三氢氧化铝(alumina trihydroxide)、硫酸钡(bariumsulfat)、白垩、硅灰石和它们的混合物。
非限制性的市售可得实例有：来自Wacker的HDK H13L，以及来自Cabot的TS720、Ultrabond5760和Ultrabond 5780。
基于组合物的总重量，无机填料可以0.1至80重量％、优选5至65重量％、更优选10至55重量％且甚至更优选20至40重量％的量存在于根据本发明的环氧组合物中。
申请人发现，这些量是优选的，因为高于80％的量可能会导致未形成连续的热固性聚合物，而是形成或多或少连续的复合材料。此外，在阳离子聚合的情况下，位于无机颗粒界面处的残留水充当链终止剂，因此导致聚合后的分子量非常低，这可能会导致实际上未固化的产物。低于1％的量可能无法提供所需的技术效果。
根据本发明的环氧组合物可以进一步包含增韧剂。通常，任何增韧剂都可以用于根据本发明的组合物中。
适合用于本发明中的增韧剂有例如(非限制性实例)
·OH或酸封端的多元醇，例如聚醚(PEG、PPG、PTHF和Velvetol)和聚酯(聚酯多元醇、聚酯二醇、脂肪酸改性的双酚A二缩水甘油醚)；
·核壳颗粒，例如PMMA壳和苯乙烯-聚丁二烯核或聚丁二烯核或聚硅氧烷核；
·非反应性增韧剂橡胶状材料和填料，例如封端的弹性体聚氨酯、嵌段共聚物橡胶(例如苯乙烯-丁二烯-异戊二烯基嵌段共聚物、苯乙烯-异戊二烯-苯乙烯嵌段共聚物和其它橡胶状嵌段共聚物)；
·反应性增韧剂橡胶状材料，例如具有两个或更多个环氧基-反应性基团(例如胺-、OH-和酸-封端的)的液体橡胶，如丁二烯-丙烯腈基橡胶、具有不同丙烯腈(AN)含量的羧基封端的丁二烯-丙烯腈(CTBN)、氨基封端的丁二烯-丙烯腈(ATBN)、环氧基封端的丁二烯-丙烯腈(ETBN)和乙烯基封端的丁二烯-丙烯腈(VTBN)；OH-封端的聚醚多元醇(PEG、PPG、PTHF型、1,3-丙二醇基)、基于腰果壳油的OH-封端的聚醚、OH-或酸-封端的聚酯、OH-封端的热塑性聚氨酯、HTPB(羟基封端的聚丁二烯)、环氧化的HTPB、聚法呢烯基多元醇、胺封端的聚醚(Jeff amines)、环氧基-封端的弹性体聚醚或聚酯(例如，基于二聚脂肪酸的)；
·也可充当增韧剂的无机填料和增强剂，例如碳酸钙、硫酸钡、氧化钙、滑石、炭黑、纺织纤维、玻璃颗粒或纤维、芳香族聚酰胺浆(aramid pulp)、硼纤维、碳纤维、矿物硅酸盐、云母、石英粉、水合氧化铝、膨润土、各种氧化铝-硅酸盐(包括粘土如硅灰石和高岭土)、气相法白炭黑、二氧化硅气凝胶、聚脲化合物、聚酰胺化合物和金属粉末(如铝粉或铁粉)；
·降低Tg并增加柔韧性的生物基增韧剂，例如腰果酚基增韧剂(OH-羟基封端的和环氧基封端的)、生物基聚醚多元醇、聚法呢烯多元醇、由生物基多元醇和croda-B增韧剂制成的TPU(具有环氧封端的聚酯)。
优选地，所述增韧剂选自核壳橡胶颗粒、具有两个或更多个环氧-反应性基团的液体橡胶、OH-封端的聚醚多元醇、OH-封端的热塑性聚氨酯、OH-封端的聚醚、聚醚聚氨酯、聚醚橡胶改性的环氧树脂、脂肪酸改性的环氧树脂、聚醚胺环氧树脂、橡胶颗粒、苯乙烯-丁二烯-异戊二烯基嵌段共聚物、聚四氢呋喃基增韧剂、cardolite增韧剂(PEG或EO改性的腰果酚或缩水甘油基改性的腰果酚二聚体(两种环氧树脂))、聚法呢烯多元醇(polyfarnesenepolyol)、封端的弹性体聚氨酯、嵌段共聚物橡胶、环氧基-封端的弹性体聚醚、环氧基-封端的弹性体聚酯、无机填料、增强剂和它们的混合物。
市售可得增韧剂的实例包括但不限于来自Kaneka的Kane Ace MX153。
基于组合物的总重量，增韧剂可以0.1至50重量％、优选5至45重量％、更优选10至40重量％且甚至更优选20至40重量％的量存在于根据本发明的环氧组合物中。
申请人发现上述范围适合于根据本发明的组合物。太高的增韧剂量可能会导致差的粘合性能、差的Tg值和不希望的粘度，而太低的量可能会导致不再适用的脆性体系。
根据本发明的环氧组合物可以进一步包含反应性稀释剂。适合用于本发明中的稀释剂有例如甲乙酮(MEK)、二甲基甲酰胺(DMF)、乙醇、丙二醇甲醚、丙二醇甲醚乙酸酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、苯乙烯、低分子量聚苯乙烯、氧化苯乙烯、烯丙基缩水甘油醚、苯基缩水甘油醚、丁基缩水甘油醚、乙烯基环己烯氧化物、新戊二醇二缩水甘油醚、丁二醇二缩水甘油醚、己二醇二缩水甘油醚、二甘醇二缩水甘油醚、二丙二醇二缩水甘油醚聚(丙二醇)二缩水甘油醚、硫二甘醇二缩水甘油醚、ε-己内酰胺、丁内酯、丙烯腈和它们的混合物。
市售可得的反应性稀释剂的实例包括但不限于来自Palmer Holland的DER 732、DER 736、来自Exion的Cardura E10P和来自BASF的Efka 5381。
基于组合物的总重量，反应性稀释剂可以以0.2至15重量％、优选0.1至7.5重量％的量存在于根据本发明的环氧组合物中。
可以向根据本发明的环氧组合物中加入粘合促进剂，以改善环氧树脂与基材的粘合性。粘合促进剂可以通过在界面处形成新的层来发挥作用，该新的层牢固地同时粘合到基材和涂层上。所得的界面区域也可以更能抵抗来自环境的化学侵蚀。
对粘合促进剂的选择可以由组合物待施用的表面的类型决定。也就是说，最常见的市售粘合促进剂是有机硅烷，其中某些环氧官能有机硅烷类型已经在上文中提及。可用于本文中的其它类型的粘合促进剂包括：有机金属化合物，例如钛酸酯和锆酸酯，其具体实例包括三(N-乙基氨基乙基氨基)钛酸异丙酯、二(二辛基亚磷酸酰氧基)钛酸四异丙酯(tetraisopropyl di(dioctylphosphito)titanate)、新烷氧基三新癸酰基锆酸酯和丙酸锆；二羟基酚类化合物，例如儿茶酚和硫代二酚；多元酚，例如连苯三酚、没食子酸或单宁酸；磷酸酯，例如磷酸三甲苯酯，和增塑溶胶，其是聚氯乙烯颗粒在增塑剂中的悬浮物(suspension)。
市售可得粘合促进剂的实例包括但不限于来自Evonik的Glymo和来自Momentive的Silquest。
基于组合物的总重量，粘合促进剂可以以0.01至5重量％、优选0.1至2.5重量％的量存在于根据本发明的环氧组合物中。
根据本发明的环氧组合物可以进一步包含导电填料。优选地，导电填料选自银、镍、碳、炭黑、石墨、石墨烯、铜、金、铂、铝、铁、锌、钴、铅、锡合金、涂银的铜、涂银的石墨、涂银的聚合物、涂银的铝、涂银的玻璃、涂银的碳、涂银的氮化硼、涂银的氧化铝、涂银的氢氧化铝及它们的混合物。
基于组合物的总重量，导电填料可以20至90重量％、优选30至70重量％、更优选40至60重量％的量存在于根据本发明的环氧组合物中。
根据本发明的环氧组合物可以进一步包含导热体。
优选地，导热体选自氧化铝、三氢氧化铝、氮化硼、氮化铝及它们的混合物。同样，一些上述导电填料也可以用作导热体。
市售可得导热体的实例包括但不限于来自Momentive的Polartherm PT110。
基于组合物的总重量，导热体可以0.01至5重量％、优选0.2至2.5重量％的量存在于根据本发明的环氧组合物中。
根据本发明的环氧组合物可进一步包含润湿剂。可以使用任何与环氧树脂相容的润湿剂。优选地，润湿剂是基于硅氧烷的润湿剂。市售可得润湿剂的实例包括但不限于来自Evonik的Dynol 980以及来自BYK的BYK W 9010、BYK W 940。
基于组合物的总重量，润湿剂可以0.01至10重量％、优选0.1至5重量％、更优选0.1至1.0重量％的量存在于根据本发明的环氧组合物中。
本发明涉及根据本发明的环氧组合物的固化产物。根据本发明的环氧组合物优选在以下条件下固化：在23℃和50％rh下2天，或在80℃下30分钟。
本发明涵盖根据本发明的环氧组合物用作结构粘合剂、涂料或底漆的用途。根据本发明的环氧组合物特别可用于要求低粘度以易于分配和润湿的应用，特别是可用作电子设备组装、汽车组装、汽车修理、航空航天、铁路和防御物(defence)中的结构粘合剂。
实施例：
表1
钢上的搭接剪切粘附力：
钢上的搭接剪切粘附力根据DIN EN ISO 527-1/-2测量。
试件：钢/钢(不锈钢，14401，1.5mm)
预处理试件：用乙酸乙酯清洗
粘合搭接剪切样品：使用200μm玻璃珠重叠：10×25mm
固化：80℃下30分钟(在烘箱中的两块钢板之间)
表2
DMA由固化膜测量：
试件：35x 10x 3mm
预处理形式：在80℃下干燥30分钟
固化：80℃下30分钟(在烘箱中的两块钢板之间)表3
| 测试条件 | Tg[℃] | |
| 实例1 | -40℃–200℃,5K/min | 72.41 |
Claims (13)
1.环氧组合物，其包含：
a)脂环族环氧树脂；
b)固化剂；和
c)具有结构I的生物基环氧化合物：
2.根据权利要求1所述的环氧组合物，其中所述具有结构I的生物基环氧化合物为β-异构体。
3.根据权利要求1或2所述的环氧组合物，其中根据ASTM D6866测定，所述具有结构I的生物基环氧化合物由100％生物基碳原子组成。
4.根据权利要求1至3中任一项所述的环氧组合物，其中基于所述组合物的总重量，所述具有结构I的生物基环氧化合物以1至80重量％、优选2至65重量％、更优选3至45重量％且甚至更优选4至30重量％的量存在。
5.根据权利要求1至4中任一项所述的环氧组合物，其中所述脂环族环氧树脂选自
以及它们的混合物。
6.根据权利要求1至5中任一项所述的环氧组合物，其中基于所述组合物的总重量，所述脂环族环氧树脂以10至98重量％、优选12至85重量％、更优选15至80重量％且甚至更优选15至60重量％的量存在。
7.根据权利要求1至6中任一项所述的环氧组合物，其中所述固化剂选自铵盐、吡啶盐、咪唑鎓盐、胍鎓盐、噁唑鎓盐、噻唑鎓盐、碘鎓盐、锍盐和磷鎓盐以及它们的混合物。
8.根据权利要求1至7中任一项所述的环氧组合物，其中基于所述组合物的总重量，所述固化剂以0.01至15重量％、优选0.1至10重量％、更优选0.2至10重量％且甚至更优选0.25至5重量％的量存在。
9.根据权利要求1至8中任一项所述的环氧组合物，其中所述组合物还包含无机填料。
10.根据权利要求9所述的环氧组合物，其中所述无机填料选自二氧化硅、气相法白炭黑、硅藻土、氧化铝、氧化锌、氧化铁、氧化镁、氧化锡、氧化钛、氢氧化镁、氢氧化铝、碳酸镁、硫酸钡、石膏、硅酸钙、滑石、玻璃珠、绢云母活化白土、膨润土、氮化铝、氮化硅、二氢氧化镁、三氢氧化铝、硫酸钡、白垩、硅灰石和它们的混合物。
11.根据权利要求9或10所述的环氧组合物，其中基于所述组合物的总重量，所述无机填料以0.1至80重量％、优选5至65重量％、更优选10至55重量％且甚至更优选20至40重量％的量存在。
12.根据权利要求1至11中任一项所述的环氧组合物的固化产物。
13.根据权利要求1至12中任一项所述的环氧组合物用作结构粘合剂、涂料或底漆的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20207701.2A EP4001338B1 (en) | 2020-11-16 | 2020-11-16 | Cationic epoxy compositions |
| EP20207701.2 | 2020-11-16 | ||
| PCT/EP2021/077223 WO2022100927A1 (en) | 2020-11-16 | 2021-10-04 | Cationic epoxy compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116438222A true CN116438222A (zh) | 2023-07-14 |
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ID=73452018
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|---|---|---|---|
| CN202180076989.2A Pending CN116438222A (zh) | 2020-11-16 | 2021-10-04 | 阳离子环氧组合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20230287168A1 (zh) |
| EP (1) | EP4001338B1 (zh) |
| JP (1) | JP2023549254A (zh) |
| KR (1) | KR20230107244A (zh) |
| CN (1) | CN116438222A (zh) |
| ES (1) | ES2973297T3 (zh) |
| TW (1) | TW202227579A (zh) |
| WO (1) | WO2022100927A1 (zh) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT521316A1 (de) * | 2018-06-07 | 2019-12-15 | All Bones Gmbh | Polymermischung sowie deren Verwendung im 3D-Druck |
| EP3725820B1 (en) * | 2019-04-16 | 2022-04-06 | Henkel AG & Co. KGaA | Use of functionalized alpha-angelica lactones |
-
2020
- 2020-11-16 ES ES20207701T patent/ES2973297T3/es active Active
- 2020-11-16 EP EP20207701.2A patent/EP4001338B1/en active Active
-
2021
- 2021-10-04 WO PCT/EP2021/077223 patent/WO2022100927A1/en active Application Filing
- 2021-10-04 CN CN202180076989.2A patent/CN116438222A/zh active Pending
- 2021-10-04 JP JP2023528646A patent/JP2023549254A/ja active Pending
- 2021-10-04 KR KR1020237016051A patent/KR20230107244A/ko active Search and Examination
- 2021-10-27 TW TW110139770A patent/TW202227579A/zh unknown
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2023
- 2023-05-16 US US18/198,215 patent/US20230287168A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20230287168A1 (en) | 2023-09-14 |
| EP4001338B1 (en) | 2024-01-31 |
| TW202227579A (zh) | 2022-07-16 |
| ES2973297T3 (es) | 2024-06-19 |
| EP4001338A1 (en) | 2022-05-25 |
| KR20230107244A (ko) | 2023-07-14 |
| WO2022100927A1 (en) | 2022-05-19 |
| JP2023549254A (ja) | 2023-11-22 |
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