CN110431162B - 制备含有噁唑烷酮基团的化合物的方法 - Google Patents
制备含有噁唑烷酮基团的化合物的方法 Download PDFInfo
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- CN110431162B CN110431162B CN201880018933.XA CN201880018933A CN110431162B CN 110431162 B CN110431162 B CN 110431162B CN 201880018933 A CN201880018933 A CN 201880018933A CN 110431162 B CN110431162 B CN 110431162B
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- diisocyanate
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- carbon atoms
- isocyanate
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- 150000001875 compounds Chemical class 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 24
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000012948 isocyanate Substances 0.000 claims abstract description 20
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 14
- 238000000465 moulding Methods 0.000 claims abstract description 13
- 239000000460 chlorine Chemical group 0.000 claims abstract description 11
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 7
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- 125000005842 heteroatom Chemical group 0.000 claims description 16
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- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
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- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 10
- 239000011630 iodine Substances 0.000 abstract description 10
- 229910052740 iodine Inorganic materials 0.000 abstract description 10
- 125000000962 organic group Chemical group 0.000 abstract 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 239000004604 Blowing Agent Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 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
- 239000007795 chemical reaction product Substances 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000002666 chemical blowing agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
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- 239000003822 epoxy resin Substances 0.000 description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000009755 vacuum infusion Methods 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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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- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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Abstract
本发明涉及制备具有噁唑烷酮基团的模制品的方法,其中将多异氰酸酯(a)与至少一种具有至少两个环氧基团的有机化合物(b)、至少一种促进异氰酸酯/环氧化物反应的催化剂(c)以及如果存在,助剂和添加剂(d)混合,形成反应混合物,将该混合物置于模具中或模具上,反应得到具有噁唑烷酮基团的模制品,其中促进异氰酸酯/环氧化物反应的催化剂(c)包含通式[M(R1)(R2)(R3)(R4)]+[X In]‑的化合物,其中M代表氮原子或磷原子,R1、R2、R3和R4代表有机基团,X代表氟、氯、溴或碘,I代表碘并且n代表0.1至10的有理数。本发明还涉及一种具有噁唑烷酮基团并且可通过这种方法获得的模制品,以及涉及本发明的催化剂用于制备具有噁唑烷酮基团的模制品的用途。
Description
本发明涉及制备含有噁唑烷酮基团的模制品的方法,其中将多异氰酸酯(a)与至少一种具有两个或更多个环氧基团的有机化合物(b)、至少一种用于异氰酸酯/环氧化物反应的催化剂(c)和任选的助剂和添加剂材料(d)混合,形成反应混合物,将该混合物引入或施用于模具,反应得到含有噁唑烷酮基团的模制品,其中用于异氰酸酯/环氧化物反应的催化剂(c)包含通式[M(R1)(R2)(R3)(R4)]+[X In]-的化合物,其中M为氮原子或磷原子,R1、R2、R3和R4为有机基团,X为氟、氯、溴或碘,I为碘并且n代表0.1至10的有理数。本发明还涉及一种含有噁唑烷酮基团并且可通过这种方法获得的模制品,以及涉及本发明的催化剂用于制备含有噁唑烷酮基团的模制品的用途。
环氧化物与异氰脲酸酯的反应提供了既含有异氰脲酸酯基团又含有噁唑烷酮基团的结构。这些化合物也称为环氧-异氰酸酯化合物(EPIC化合物)。在此情况中使用的催化剂可为溴化锂、季铵盐或路易斯酸,例如氯化铝。所得的EPIC化合物在高长期温度稳定性和低可燃性方面引人注目。然而,通过这种方法获得的材料不是可再熔的,原因在于高比例的异氰脲酸酯结构和所产生的严重交联,并且该材料表现出高脆性。
WO 2015173101记载了使用基于季磷、砷、锑或铋的催化剂,产生了含有噁唑烷酮基团并具有高区域选择性的线性低聚化合物,其中所得区域选择性EPIC化合物在低粘度和相对低的玻璃化转变温度方面引人注目。
WO 2015173110记载了无卤催化剂用于制备含有噁唑烷酮基团的化合物的用途。该文献同样主要记载了预聚物;没有记载模制品。
为了降低异氰脲酸酯基团的比例并改善这些材料的脆性,WO 86/06734提出使用有机碘化锑结构。为此,制备含有噁唑烷酮基团的预聚物,并在第二步中通过加入其他物质(实例为亚甲基二苯胺)来固化。
本发明的一个目的是提供一种含有噁唑烷酮基团的固体,更特别是含有噁唑烷酮基团的模制品,所述模制品具有优异的机械性能和高温稳定性。出乎意料地,本发明的目的已通过一种含有噁唑烷酮基团并且可通过下述方法制备的模制品实现:其中将多异氰酸酯(a)与至少一种具有两个或更多个环氧基团的有机化合物(b)、至少一种用于异氰酸酯/环氧化物反应的催化剂(c)和任选的助剂和添加剂材料(d)混合,形成反应混合物,将该混合物引入或施用于模具,反应得到含有噁唑烷酮基团的模制品,其中用于异氰酸酯/环氧化物反应的催化剂(c)包含通式[M(R1)(R2)(R3)(R4)]+[X In]-的化合物,其中M为氮原子或磷原子,R1、R2、R3和R4为有机基团,X为氟、氯、溴或碘,I为碘并且n代表0.1至10的有理数。
在一个优选的实施方案中,本发明的模制品在一步中获得。此处,“在一步中”意指用于制备模制品的所有组分在反应开始之前混合在一起并随后进行反应直至获得模制品,而不添加其他化合物,更特别地不添加含有对异氰酸酯基团或环氧基团具有反应性的基团的其他化合物。
所得模制品优选为固体。在本发明的上下文中,固体的根据DIN EN ISO 868的肖氏硬度大于10肖氏A,优选大于30肖氏A,更特别地大于50肖氏A。在另一个优选的实施方案中,本发明的模制品具有根据DIN EN ISO 179-1的高夏比缺口冲击强度,优选大于10kJ/m2,更优选大于20kJ/m2,更特别地大于30kJ/m2。
可以使用的用于制备本发明的模制品的模具是至少在部分反应期间使反应混合物成为宏观形状以形成固体的所有制品,并且所述固体的宏观形状在固化形成本发明的固体后也是明显的。模具材料可在固化后移出,但也可扮演本发明模制品的一部分,如在例如通过浸涂涂覆制品的情况下,如电子制品(如变压器)的浸涂。微观成型,通过例如包含对宏观形状没有影响的化合物(例如填料)进行微观成型,不认为是本发明意义上的模具。本发明的模具的实例为开放式或封闭式模具,由例如金属或塑料制成,但也包括卷绕芯,用于制备通常用于真空灌注的卷绕物品或管子、真空模具,或者为允许连续成型的模具,如通常用于拉挤成型。
考虑本身已知的脂族、脂环族、芳脂族多官能异氰酸酯以及优选的芳族多官能异氰酸酯用作多异氰酸酯a)。这种类型的多官能异氰酸酯本身是已知的,或者可通过本身已知的方法获得。更特别地,多官能异氰酸酯也可作为混合物使用,在这种情况下,组分a)相应地包含多种多官能异氰酸酯。考虑用作多异氰酸酯的多官能异氰酸酯每分子具有两个异氰酸酯基团(下文称为二异氰酸酯)或多于两个异氰酸酯基团。
具体实例为:在亚烷基中具有4至12个碳原子的亚烷基二异氰酸酯,例如十二烷1,12-二异氰酸酯、2-乙基四亚甲基1,4-二异氰酸酯、2-甲基五亚甲基1,5-二异氰酸酯、四亚甲基1,4-二异氰酸酯、以及优选的六亚甲基1,6-二异氰酸酯;脂环族二异氰酸酯,如环己烷1,3-和1,4-二异氰酸酯及这些异构体的任意混合物、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(IPDI)、六氢甲苯2,4-和2,6-二异氰酸酯及相应异构体的混合物、二环己基甲烷4,4'-、2,2'-和2,4'-二异氰酸酯及相应异构体的混合物;以及优选的芳族多异氰酸酯,如甲苯2,4-和2,6-二异氰酸酯及相应异构体的混合物、二苯基甲烷4,4'-、2,4'-和2,2'-二异氰酸酯及相应异构体的混合物、二苯基甲烷4,4'-和2,2'-二异氰酸酯的混合物、多苯基多亚甲基多异氰酸酯、二苯基甲烷2,4'-、4,4'-和2,2'-二异氰酸酯与多苯基多亚甲基多异氰酸酯的混合物(粗MDI)以及粗MDI与甲苯二异氰酸酯的混合物。
特别合适的为2,2'-、2,4'-和/或4,4'-二苯基甲烷二异氰酸酯(MDI)、1,5-亚萘基二异氰酸酯(NDI)、2,4-和/或2,6-甲苯二异氰酸酯(TDI)、3,3'-二甲基联苯二异氰酸酯、1,2-二苯基乙烷二异氰酸酯和/或对苯二异氰酸酯(PPDI)、三亚甲基二异氰酸酯、四亚甲基二异氰酸酯、五亚甲基二异氰酸酯、六亚甲基二异氰酸酯、七亚甲基二异氰酸酯和/或八亚甲基二异氰酸酯、2-甲基五亚甲基1,5-二异氰酸酯、2-乙基亚丁基1,4-二异氰酸酯、五亚甲基1,5-二异氰酸酯、亚丁基1,4-二异氰酸酯、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯,IPDI)、1,4-和/或1,3-双(异氰酸根合甲基)环己烷(HXDI)、1,4-环己烷二异氰酸酯、1-甲基-2,4-和/或2,6-环己烷二异氰酸酯以及4,4'-、2,4'-和/或2,2'-二环己基甲烷二异氰酸酯。
还经常使用改性多异氰酸酯,即通过有机多异氰酸酯的化学反应获得并且每分子具有至少两个反应性异氰酸酯基团的产物。可特别提及含有脲、缩二脲、脲基甲酸酯、碳二亚胺、异氰脲酸酯、脲二酮、氨基甲酸酯(carbamate)和/或氨基甲酸乙酯(urethane)基团的多异氰酸酯,通常还与未转化的多异氰酸酯一起。
含环氧基的组分b)包括任意所需的包含至少两个环氧基团的脂族、环脂族、芳族和/或杂环化合物。可用作组分b)的优选的环氧化物每分子具有2至4个、优选2个环氧基团,并且环氧当量为90至500g/eq,优选140至220g/eq。
合适的聚环氧化物例如为多元酚的聚缩水甘油醚,所述多元酚例如为邻苯二酚、间苯二酚、对苯二酚、4,4'-二羟基二苯基丙烷(双酚A)、4,4'-二羟基-3,3'-二甲基二苯基甲烷、4,4'-二羟基二苯基甲烷(双酚F)、4,4'-二羟基二苯基环己烷、4,4'-二羟基-3,3'-二甲基二苯基丙烷、4,4'-二羟基联苯、4,4'-二羟基二苯基砜(双酚S)、三(4-羟基苯基)-甲烷、上述二酚的氯化和溴化产物、酚醛清漆(即,在当量比小于1:1下在酸性催化剂的存在下,一元酚或多元酚和/或甲酚与醛、特别是甲醛的反应产物)、通过将2mol芳族羟基羧酸的钠盐与1mol二卤代烷烃或二卤代二烷基酯酯化获得的二酚(参见英国专利1 017 612)或者通过苯酚与含有至少两个卤原子的长链卤代烷烃缩合获得的多酚(参见GB专利1 024288)。还可提及:基于芳族胺和表氯醇的聚环氧化合物,例如N-二(2,3-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷、N,N-二环氧丙基-4-氨基苯基缩水甘油醚(参见GB专利772 830和816 923)。
其他可能的为:多元芳族、脂族和脂环族羧酸的缩水甘油酯,例如邻苯二甲酸二缩水甘油酯、间苯二甲酸二缩水甘油酯、对苯二甲酸二缩水甘油酯、己二酸二缩水甘油酯以及1mol芳族或脂环族二羧酸酐与1/2mol二醇或1/n mol具有n个羟基的多元醇的反应产物的缩水甘油酯,或者可任选地用甲基取代的六氢邻苯二甲酸二缩水甘油酯。
也可以使用多元醇的缩水甘油醚,所述多元醇例如1,4-丁二醇(DY-D,Huntsman)、1,4-丁烯二醇、甘油、三羟甲基丙烷(DY-T/CH,Huntsman)、季戊四醇和聚乙二醇。感兴趣的还有异氰脲酸三缩水甘油酯、N,N'-二环氧丙基氧基酰胺、多元硫醇的多缩水甘油基硫醚,例如二巯基甲基苯、二缩水甘油基三亚甲基三砜、基于乙内酰脲的多缩水甘油醚。
最后,还可使用多不饱和化合物的环氧化产物,例如植物油及其转化产物。也可以使用二烯烃和多烯烃的环氧化产物,例如丁二烯、乙烯基环己烷、1,5-环辛二烯、1,5,9-环十二碳三烯、仍包含可环氧化双键的链增长加成聚合物和互聚体(例如基于聚丁二烯、聚异戊二烯、丁二烯-苯乙烯互聚体、二乙烯基苯、二环戊二烯、不饱和聚酯);通过Diels-Alder加成得到并随后通过用过氧化物(Perverbindung)环氧化而转化成聚环氧化物的烯烃的环氧化产物,或者含有通过桥联原子或桥联原子基团连接的两个环戊烯环或环己烯环的化合物的环氧化产物。
根据本发明,优选用作组分b)的为下列聚环氧化物或其混合物:
多元酚的多缩水甘油醚,特别是双酚A(GY250,Huntsman;0162,Bakelite AG;Resin 162,Hexion Specialty ChemicalsGmbH;Eurepox 710,Brenntag GmbH;GY250,Hunstman,D.E.R.TM332,The DowChemical Company;A 18-00,LEUNA-Harze GmbH)或双酚F(4,4'-二羟基二苯基甲烷;GY281,Huntsman;F 16-01,LEUNA-Harze GmbH;F17-00,LEUNA-Harze GmbH)的多缩水甘油醚;基于芳族胺的聚环氧化合物,尤其是双(N-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷和N,N-二环氧丙基-4-氨基苯基缩水甘油醚;脂环族二羧酸的多缩水甘油酯,尤其是六氢邻苯二甲酸二缩水甘油酯以及来自nmol六氢邻苯二甲酸酐与1mol具有n个羟基的多元醇(n=2至6的整数)的反应产物的聚环氧化物,尤其是3mol六氢邻苯二甲酸酐与1mol1,1,1-三羟甲基丙烷的反应产物的聚环氧化物;3,4-环氧环己基甲基3,4-环氧环己烷羧酸酯。
非常特别优选双酚A和双酚F以及酚醛清漆的聚缩水甘油醚,特别是双酚F的聚缩水甘油醚。
液体聚环氧化物或低粘度二环氧化物,例如双(N-环氧丙基)苯胺或乙烯基环己烷二环氧化物,在特殊情况下可进一步降低已呈液体的聚环氧化物的粘度或将固体聚环氧化物转化成液体混合物。
组分b)优选以对应于异氰酸酯基团与环氧基团的当量比为1:10至10:1、优选1:5至5:1且更特别是1:1.5至2:1的量使用。
催化剂c)强烈促进含有环氧基团的有机化合物(b)与多异氰酸酯(a)的反应。此处催化剂(c)包含至少一种下述通式的化合物
[M(R1)(R2)(R3)(R4)]+[X In]-,
其中M为氮原子或磷原子,优选氮原子;R1、R2、R3和R4为有机基团,各自彼此独立地选自具有1至22个碳原子并且可能被杂原子取代或被含杂原子的取代基取代的直链或支链烷基、具有3至22个碳原子并且可能被杂原子取代或被含杂原子的基团取代的烷基桥联脂环族或芳族基团(其中M可为环的一部分)以及具有6至18个碳原子并且可能被具有1至10个碳原子的烷基和/或杂原子取代的芳基(其中M可为环的一部分);X为氟、氯、溴或碘,优选氯或溴;I为碘;并且n代表0.1至10的有理数、优选0.5至3、更优选1.5至2.5且更特别是2.0。
基团R1、R2、R3和R4优选为有机基团,各自彼此独立地选自苯基、环己基和具有1至6个碳原子的直链或支链烷基,其各自也可以被取代,但优选未被取代。在一个特别优选的实施方案中,基团R1、R2、R3和R4相同。
在本发明的另一个实施方案中,用作阳离子的化合物[M(R1)(R2)(R3)(R4)]+为包含至少一个由两个基团R的桥接形成的五元至六元杂环、更特别是具有至少一个氮原子以及任选的氧原子或硫原子的五元杂环的化合物。特别优选的化合物为包含至少一个五元至六元杂环的那些化合物,所述杂环具有一个、两个或三个氮原子和一个硫原子或一个氧原子,尤其优选具有两个氮原子的那些。进一步优选的为芳族杂环,例如吡啶鎓、哒嗪鎓、嘧啶鎓、吡嗪鎓、咪唑鎓、吡唑鎓、吡唑啉鎓、咪唑鎓、噻唑鎓、噁唑鎓、吡咯烷鎓和咪唑烷鎓。在芳族杂环的情况下,基团-R4可以用芳族双键替代。
就本发明而言,杂原子为不是碳或氢的原子,其中杂原子优选包含氮、氧、硫、磷或卤素原子,例如氟、氯或溴。[X In]-为阴离子,其中X为氟、氯、溴或碘,并且I为元素碘。此处负电荷的确切位置不是本发明的主题。通常,电荷将位于X,意味着X为X-,即氟离子(F-)、氯离子(Cl-)、溴离子(Br-)或碘离子(I-)。该阴离子[X In]-通过[M(R1)(R2)(R3)(R4)]+X-与元素碘以1:n的摩尔比反应获得,其中n如上所定义。化合物[M(R1)(R2)(R3)(R4)]+X-是已知的并且包括例如四丁基氯化铵、四丁基溴化铵或四丁基溴化鏻,并且可商购获得。三卤化季铵的制备也是已知的,并且记载于例如H.Haller et al.Z.Anorgan.Allg.Chem.,2014,640,(7),1281-1291中。
催化剂(c)通常以0.1至10重量%、优选0.2至5重量%且更特别是0.5至3重量%的量使用,各自基于组分(a)、(b)和(c)的总重量计。
所用的添加剂材料d)可为,例如多元醇、多胺、发泡剂、填料、已知的泡沫稳定剂、脱模剂以及已知的UV稳定剂和水解抑制剂。
多元醇包括具有至少2个、更特别是2至8个且优选2至3个醇羟基并且分子量为62至8000g/mol的化合物。这些化合物作为合成聚氨酯的组分是本身已知的,并且包含低分子量扩链剂和数均分子量大于200g/mol的多元醇。扩链剂的实例为简单的多元醇,例如乙二醇、己烷-1,6-二醇、甘油或三羟甲基丙烷;多元醇的实例为包含二甲基硅氧烷单元的多元醇,例如双(二甲基羟甲基甲硅烷基)醚;含有酯基的多羟基化合物,例如蓖麻油;或多羟基聚酯,其是可通过过量的简单多元醇与举例列出的优选的二元羧酸和/或它们的氢化物(例如己二酸、邻苯二甲酸或邻苯二甲酸酐)缩聚获得的类型;多羟基聚醚,其是可通过将环氧烷烃(如环氧丙烷和/或环氧乙烷)加成到合适的起始分子(例如水、刚才所述的简单醇或者具有至少两个氨性NH键的胺)上获得的类型;或聚碳酸酯多元醇,其可以例如由多元醇和碳酸酯或光气获得。
可以使用的多胺为具有至少两个异氰酸酯反应性氢原子的化合物,其中至少一个属于伯或仲氨基。它们包含聚醚胺和分子量小于500g/mol的化合物。聚醚胺由聚氨酯化学已知,并且可通过聚醚多元醇的末端胺化获得。它们优选具有500至8000g/mol的分子量。优选使用的化合物具有两个氨基并且分子量小于500g/mol,更优选分子量为58至300g/mol、更特别是100至200g/mol。这些化合物的异氰酸酯反应性基团优选为两个伯氨基。在一个特别优选的实施方案中,伯氨基与芳族碳原子、优选与芳族6元环键合,更特别是在间位或对位键合。
优选使用小于20重量%、更优选小于10重量%的多元醇和/或多胺,更特别是不含多元醇和/或多胺。当使用多元醇和/或多元胺时,优选其量使得多异氰酸酯(a)中的异氰酸酯基团与组分(d)的异氰酸酯-反应性化合物的比值大于1.5:1,优选大于5:1,更特别地大于10:1。
用于制备本发明的泡沫的发泡剂包括化学发泡剂,例如水、甲酸及其混合物。除甲酸和水外,合适的化学发泡剂还有二乙氧磷酰硫胆碱氧化物(phospholine oxide)。这些试剂与异氰酸酯基团反应形成二氧化碳,并且在甲酸的情况下形成二氧化碳和一氧化碳。因为这些发泡剂通过与异氰酸酯基团的化学反应释放气体,所以它们被称为化学发泡剂。也可以使用物理发泡剂,例如低沸点烃。特别合适的为对多异氰酸酯a)呈惰性且在大气压下沸点低于100℃、优选低于50℃的液体,故此它们在放热的加聚反应的影响下蒸发。优选使用的这种液体的实例为烷烃,例如庚烷、己烷、正戊烷和异戊烷,优选正戊烷和异戊烷、正丁烷和异丁烷以及丙烷的工业混合物;环烷烃,例如环戊烷和/或环己烷;醚,例如呋喃、二甲醚和二乙醚;酮,例如丙酮和甲基乙基酮;羧酸烷基酯,例如甲酸甲酯、草酸二甲酯和乙酸乙酯;和卤代烃,例如二氯甲烷、二氯一氟甲烷、二氟甲烷、三氟甲烷、二氟乙烷、四氟乙烷、氯二氟乙烷、1,1-二氯-2,2,2-三氟乙烷、2,2-二氯-2-氟乙烷、五氟丙烷、七氟丙烷和六氟丁烯。也可以使用这些低沸点液体彼此和/或与其他取代或未取代的烃的混合物。物理发泡剂优选可溶于组分(b)。
如果使用发泡剂,则优选不使用卤代烃作为发泡剂。优选用作化学发泡剂的为水、甲酸/水混合物或甲酸,特别优选的化学发泡剂为甲酸-水混合物或甲酸。优选用作物理发泡剂的为戊烷异构体、或戊烷异构体的混合物。在一个特别优选的实施方案中,使用小于5重量%、优选小于2重量%、更优选小于0.5重量%且更特别是小于0.1重量%的发泡剂,各自基于组分(a)至(d)的总重量计。
任选伴随使用的其他助剂和添加剂(d)为例如填料,如细碎的石英、白垩、白云石(Microdol)、氧化铝、碳化硅、石墨或刚玉;颜料,如二氧化钛、氧化铁或有机颜料如酞菁颜料;增塑剂,如邻苯二甲酸二辛酯、磷酸三丁酯或磷酸三苯酯;可结合的增容剂,如甲基丙烯酸、β-羟丙基酯、马来酸酯和富马酸酯;增强阻燃性的物质,如红磷或氧化镁;可溶性染料或增强材料,如玻璃纤维或玻璃织物。同样合适的为C纤维和C纤维织物及其他有机聚合物纤维,例如芳族聚酰胺纤维或LC聚合物纤维(LC=“液晶”)。还考虑作为填料的为金属填料,例如铝、铜、铁和/或钢。更特别地,金属填料以颗粒形式和/或粉末形式使用。
此外,助剂和添加剂(d)还可包含已知的聚醚硅氧烷类型的泡沫稳定剂;脱模剂,例如聚酰胺蜡和/或硬脂酸衍生物和/或天然蜡,实例为巴西棕榈蜡;以及已知的UV稳定剂和水解抑制剂。
本发明的含有噁唑烷酮基团的固体优选为热固性材料。为了制备热固性材料,这些反应物关于反应性基团的平均官能度优选为1.9至3.0,更优选大于1.95至2.5。此处含有噁唑烷酮基团的化合物的性质在每种情况下可基于所用化合物、根据聚氨酯化学、通过调节例如交联密度来自行定制。
通过混合组分(a)至(d)以形成反应混合物并使反应混合物在模具中或模具上反应完成来制备本发明的模制品。所有反应物可以同时混合。在本发明的一个实施方案中,首先加入包含组分(b)和(c)以及任选的(d)的多元醇组分,然后与异氰酸酯组分混合以形成反应混合物。在本发明的另一个实施方案中,将多异氰酸酯(a)与催化剂(c)混合以形成异氰酸酯组分,然后将其与组分(b)和任选的(d)混合以形成反应混合物。优选在高于120℃、更优选为150℃至275℃且更特别是180至220℃的温度下,使反应混合物反应形成含有噁唑烷酮基团的模制品,优选通过模具的温度控制或通过在烘箱中固化来设定所述温度。混合时原料的温度优选为0至100℃,更优选为20至80℃且更特别是25至60℃。当获得足够的强度时,可以从模具中取出模制品。
本发明的含有噁唑烷酮基团的化合物由于具有非常高的热稳定性和优异的机械性能,例如优异的缺口冲击强度而引人注目。本发明的含有噁唑烷酮基团的热固性材料可用作例如涂料、粘合剂和复合材料。因此,本发明的反应混合物在50℃下具有长的开放时间。此外,本发明的含有噁唑烷酮基团的热固性材料表现出高的玻璃化转变温度、优异的机械值(例如拉伸强度或硬度)以及高的冲击强度,因此使它们非常适合用作电子应用领域的浸渍清漆,例如用于变压器的绝缘层;用在复合部件(例如转绕组件、桅杆)或通过例如真空灌注技术制备的大型复合部件(例如用于风力涡轮机的叶片)中。本发明的含有噁唑烷酮基团的热固性材料特别优选用在复合部件(例如转绕组件)以及特别是通过例如真空灌注技术制备的大型复合部件(例如用于风力涡轮机的叶片)中。
实施例:
下面使用实施例来示例说明本发明。
原料:
环氧树脂1:基于双酚A的二缩水甘油醚(购自LEUNA-Harze GmbH的LupranateEpilox A19-03),环氧当量(g/当量)为190。
环氧树脂2:邻甲苯基缩水甘油醚(购自EMS-Griltech的Grilonit RV 1805),环氧当量(g/当量)为168。
Iso 1:脲酮亚胺改性的4,4'-MDI(购自BASF的Lupranate MM103)。
Iso 2:基于4,4'-MDI的预聚物,NCO值为23%(购自BASF的Lupranate MP102)。
Iso 3:4,4'-MDI(购自巴斯夫的Lupranate ME)
Mesamoll:购自Lanxess的(C10-C21)链烷磺酸苯酯。
四丁基氯化铵、四丁基溴化铵,
购自Sigma-Aldrich的四苯基溴化鏻和碘。
实施例:
催化剂的制备:
催化剂1:
称取27.8g四丁基氯化铵(0.1mol)和25.4g I2(0.1mol)到100mL玻璃烧瓶中。将容器封闭并在烘箱中于130℃下加热2小时。之后,温度降低至90℃。将烧瓶从烘箱中取出,将反应产物直接与79.8g Mesamoll混合,预先短暂加热至90℃。随后封闭烧瓶并进一步冷却混合物,在55℃下储存并原样使用。反应产物和Mesamoll的混合比为0.4:0.6。所述催化剂在下文中称为催化剂1。
催化剂2:
为了制备催化剂2,将四丁基氯化铵与碘(I2)的摩尔比降至1:0.5。这通过将反应物的量修改为27.8g四丁基氯化铵和12.7g碘完成。
Mesamoll的合成和添加如对于催化剂1所述进行;Mesamoll的添加量为60.8g。这相当于反应产物与Mesamoll的混合比为0.4:0.6。
催化剂3:
为了制备催化剂3,将四丁基溴化铵与碘(I2)以1:1的摩尔比反应。这通过使32.2g四丁基溴化铵和25.4g碘彼此反应完成。Mesamoll的合成和添加如对于催化剂1所述进行;Mesamoll的添加量为86.4g。这相当于反应产物与Mesamoll的混合比为0.4:0.6。
催化剂4:
为了制备催化剂4,将四丁基溴化铵与碘(I2)的摩尔比降至1:0.5。这通过将反应物的量修改为32.2g四丁基溴化铵和12.7g碘完成。
Mesamoll的合成和添加如对于催化剂1所述进行;Mesamoll的添加量为67.4g。这相当于反应产物与Mesamoll的混合比为0.4:0.6。
催化剂A:
称取20.0g四丁基氯化铵和30.0g Mesamoll到100mL玻璃烧瓶中。将容器封闭并在烘箱中于130℃下加热2小时。这样得到即使在冷却至室温时也是稳定的液体组分。
催化剂B:
称取20.0g四丁基溴化铵和30.0g Mesamoll到100mL玻璃烧瓶中。将容器封闭并在烘箱中于130℃下加热2小时。这样得到即使在冷却至室温时也是稳定的液体组分。
检测噁唑烷酮基团的形成
将催化剂1至4以及催化剂A和B用于制备含有噁唑烷酮基团的聚合物。这通过由环氧树脂1和iso 1制备聚合物来完成,其中反应性基团的摩尔比计算为一比一,并且基于四丁基卤化铵含量计的催化剂的标称摩尔量保持恒定。为此,将指定组分在55℃下加热并在高速混合器(Speedmixer)中以1600rpm混合半分钟。然后,将混合物引入尺寸为15×5×0.2cm、顶部开口且温度为200℃的铝模具中,并在30分钟内完全反应。
用于形成噁唑烷酮基团的检测方法为IR光谱法。使用装配有金刚石测量头的购自Bruker的型号ALPHA-27的IR仪器进行IR分析。将少量聚合物样品(几毫克)压在金刚石测量头上并记录光谱。通过分别在1749和1704cm-1处频带的存在来检测噁唑烷酮基团和异氰脲酸酯基团的形成。噁唑烷酮与异氰脲酸酯的比例基于两个频带的高度(以cm计)的比值(1749cm-1处的高度除以1704cm-1处的高度)来评价。该值越高,聚合物含有的噁唑烷酮越多、异氰脲酸酯基团越少。应注意,环氧树脂1和iso 1原料在相关的IR频率范围内没有吸收。通过在1850cm-1处的吸收值以及在约1550cm-1的吸收处发现的最小值绘制基线。
表1描述了在板上测量的混合物和噁唑烷酮:异氰脲酸酯比值(Ox/Is)。表1还示出了用本发明催化剂制备的板显示出高得多的噁唑烷酮含量。
表1
催化剂 | ||||||
1[重量份] | 4.0 | |||||
2[重量份] | 3.0 | |||||
3[重量份] | 4.3 | |||||
4[重量份] | 3.3 | |||||
A[重量份] | 2.0 | |||||
B[重量份] | 2.4 | |||||
Tg[℃] | 131 | 113 | 135 | 119 | 110 | 110 |
肖氏硬度 | 86 | 86 | 85 | 85 | 86 | 87 |
缺口冲击强度[kJ/m<sup>2</sup>] | 71 | 24 | 41 | 42 | 8 | 14 |
抗弯强度[N/mm<sup>2</sup>] | 134 | 141 | 147 | 146 | 104 | 119 |
弯曲弹性模量[N/mm<sup>2</sup>] | 2875 | 3345 | 2900 | 3317 | 3156 | 3230 |
Ox/Is比值 | 1.38 | 1.07 | 1.85 | 1.42 | 0.89 | 0.76 |
此处的机械性能如下确定:
肖氏D硬度: DIN ISO 7619-1
抗拉强度: DIN EN ISO 527
断裂伸长率: DIN EN ISO 527
弹性模量: DIN EN ISO 527
缺口冲击强度: DIN EN ISO 179-1/1eU
抗弯强度: DIN EN ISO 178
弯曲弹性模量: DIN EN ISO 178
该表示出,通过使用本发明的催化剂,在固体中获得了与异氰脲酸酯基团相比显著增加的噁唑烷酮基团水平。这对机械性能具有影响。因此,当使用本发明的催化剂时,对于恒定的硬度,特别是在玻璃化转变温度、缺口冲击强度和抗弯强度方面有所增加。
Claims (14)
1.一种制备含有噁唑烷酮基团的模制品的方法,其中将
a)多异氰酸酯与
b)至少一种具有两个或更多个环氧基团的有机化合物,
c)至少一种用于异氰酸酯/环氧化物反应的催化剂,和
d)任选的助剂和添加剂材料
混合以形成反应混合物,将该混合物引入或施用于模具,反应得到含有噁唑烷酮基团的模制品,其中用于异氰酸酯/环氧化物反应的催化剂(c)包含如下通式的化合物
[M(R1)(R2)(R3)(R4)]+[X In]-,其中
M为氮原子或磷原子,
R1、R2、R3和R4为有机基团,各自彼此独立地选自具有1至22个碳原子并且可能被杂原子取代或被含杂原子的取代基取代的直链或支链烷基、具有3至22个碳原子并且可能被杂原子取代或被含杂原子的基团取代的烷基桥联脂环族或芳族基团、以及具有6至18个碳原子并且可能被具有1至10个碳原子的烷基和/或杂原子取代的芳基,
X为氟、氯、溴或碘,
I为碘,并且
n代表0.1至10的有理数。
2.根据权利要求1所述的方法,其中n代表0.5至3的有理数。
3.根据权利要求1或2所述的方法,其中X为氯或溴。
4.根据权利要求1或2所述的方法,其中多异氰酸酯(a)中的多异氰酸酯基团与至少一种具有两个或更多个环氧基团的有机化合物(b)中的环氧基团的摩尔比为1:10至10:1。
5.根据权利要求1或2所述的方法,其中具有两个或更多个环氧基团的有机化合物选自双酚A、双酚F或酚醛清漆的聚缩水甘油醚或其混合物。
6.根据权利要求1或2所述的方法,其中R1、R2、R3和R4为有机基团,各自彼此独立地选自苯基、环己基和具有1至6个碳原子的直链或支链烷基。
7.根据权利要求1或2所述的方法,其中R1、R2、R3和R4相同。
8.根据权利要求1或2所述的方法,其中在使反应混合物反应以得到含有噁唑烷酮基团的模制品中,模具的温度为140℃至280℃。
9.根据权利要求1或2所述的方法,其中将包含组分b)和c)的多元醇组分与异氰酸酯a)混合以形成反应混合物。
10.根据权利要求1或2所述的方法,其中将包含组分a)和b)的异氰酸酯组分与催化剂c)混合以形成反应混合物。
11.根据权利要求1或2所述的方法,其中使用的多异氰酸酯a)为选自以下的异氰酸酯:十二烷-1,12-二异氰酸酯、2-乙基四亚甲基-1,4-二异氰酸酯、2-甲基五亚甲基-1,5-二异氰酸酯、四亚甲基-1,4-二异氰酸酯、六亚甲基-1,6-二异氰酸酯、环己烷-1,3-和1,4-二异氰酸酯及这些异构体的任意所需混合物、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(IPDI)、六氢甲苯-2,4-和2,6-二异氰酸酯及相应异构体的混合物、二环己基甲烷-4,4'-、2,2'-和2,4'-二异氰酸酯及相应异构体的混合物、甲苯-2,4-和2,6-二异氰酸酯及相应异构体的混合物、二苯基甲烷-4,4'-、2,4'-和2,2'-二异氰酸酯及相应异构体的混合物、多苯基多亚甲基多异氰酸酯、二苯基甲烷-4,4'-、2,4'-和2,2'-二异氰酸酯与多苯基多亚甲基多异氰酸酯的混合物(粗MDI)、以及粗MDI和甲苯二异氰酸酯的混合物。
12.根据权利要求1或2所述的方法,其中使用的多异氰酸酯a)为选自以下的异氰酸酯:脂环族二异氰酸酯。
13.根据权利要求1或2所述的方法,其中使用的多异氰酸酯a)为选自以下的异氰酸酯:二苯基甲烷-4,4'-和2,2'二异氰酸酯的混合物。
14.通式[M(R1)(R2)(R3)(R4)]+[X In]-的催化剂用于制备含有噁唑烷酮基团的模制品的用途,其中
M为氮原子或磷原子,
R1、R2、R3和R4为有机基团,各自彼此独立地选自具有1至22个碳原子并且可能被杂原子取代或被含杂原子的取代基取代的直链或支链烷基、具有3至22个碳原子并且可能被杂原子取代或含杂原子的基团取代的烷基桥联脂环族或芳族基团、以及具有6至18个碳原子并且可能被具有1至10个碳原子的烷基和/或杂原子取代的芳基,
X为氟、氯、溴或碘,
I为碘,并且
n代表0.1至10的有理数。
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