CN112969764B - 有机聚合物、包含该有机聚合物的组合物及其制造方法 - Google Patents
有机聚合物、包含该有机聚合物的组合物及其制造方法 Download PDFInfo
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- CN112969764B CN112969764B CN201980072977.5A CN201980072977A CN112969764B CN 112969764 B CN112969764 B CN 112969764B CN 201980072977 A CN201980072977 A CN 201980072977A CN 112969764 B CN112969764 B CN 112969764B
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 23
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- 239000000758 substrate Substances 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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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- C08G18/3203—Polyhydroxy compounds
- C08G18/3218—Polyhydroxy compounds containing cyclic groups having at least one oxygen atom in the ring
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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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
对于以往已知的具有羟基的氨基甲酸酯树脂而言,有时从金属基材的耐剥离性不充分。本发明的有机聚合物是具有异氰酸酯基的氨基甲酸酯预聚物(A)与式(1)所示的化合物(B)的反应产物(I)与多元胺化合物(II)的反应产物,上述氨基甲酸酯预聚物(A)是多元醇(a1)与多异氰酸酯(a2)的反应产物,上述多元醇(a1)包含高分子量多元醇(a1‑1)和低分子量多元醇(a1‑2)。[式(1)中,R1各自独立地表示单键或碳原子数1~10的烃基。R2表示碳原子数1~50的烃基,上述烃基中所含的‑CH2‑可以被取代成‑O‑。L1表示‑O‑CO‑O‑。]
Description
技术领域
本发明涉及有机聚合物、包含其的组合物及其制造方法。
背景技术
氨基甲酸酯树脂可以根据所使用的原料来调整机械强度、柔软性、耐化学试剂性等,用于建筑构件、家电制品、汽车部件、汽车外装材料、涂布剂、粘接剂、医疗器具等各种工业用途。近年来,进行了在氨基甲酸酯树脂中导入羟基的尝试(例如,参照专利文献1)。
现有技术文献
专利文献
专利文献1:日本特开2000-319504号公报
发明内容
发明要解决的课题
对于以往已知的具有羟基的氨基甲酸酯树脂而言,有时从金属基材的耐剥离性不充分。
用于解决课题的手段
本发明的有机聚合物是具有异氰酸酯基的氨基甲酸酯预聚物(A)与式(1)所示的化合物(B)的反应产物(I)与多元胺化合物(II)的反应产物,上述氨基甲酸酯预聚物(A)是多元醇(a1)与多异氰酸酯(a2)的反应产物,上述多元醇(a1)包含高分子量多元醇(a1-1)和低分子量多元醇(a1-2)。
[化学式1]
[式(1)中,
R1各自独立地表示单键或碳原子数1~10的烃基。
R2表示碳原子数1~50的烃基,上述烃基中所含的-CH2-可以被取代成-O-。
L1表示-O-CO-O-。]
发明的效果
由包含本发明的有机聚合物的组合物形成的涂膜的从金属基材的耐剥离性良好。
具体实施方式
本发明的有机聚合物是具有异氰酸酯基的氨基甲酸酯预聚物(A)与式(1)所示的化合物(B)的反应产物(I)与多元胺化合物(II)的反应产物。
[化学式2]
[式(1)中,
R1各自独立地表示单键或碳原子数1~10的烃基。
R2表示碳原子数1~50的烃基,上述烃基中所含的-CH2-可以被取代成-O-。
L1表示-O-CO-O-。]
上述氨基甲酸酯预聚物(A)是多元醇(a1)与多异氰酸酯(a2)的反应产物,上述多元醇(a1)包含高分子量多元醇(a1-1)和低分子量多元醇(a1-2)。
上述高分子量多元醇(a1-1)表示重均分子量为500以上的多元醇,该高分子量多元醇(a1-1)的重均分子量优选为700以上,更优选为800以上,优选为500000以下,更优选为300000以下,进一步优选为100000以下,更进一步优选为50000以下,特别优选为10000以下。
在本说明书中,重均分子量和数均分子量可以使用凝胶渗透色谱法,作为将聚苯乙烯作为标准试样的换算值进行测定。
上述高分子量多元醇(a1-1)中所含的羟基的数量为2以上,优选为10以下,更优选为6以下,进一步优选为4以下。
作为上述高分子量多元醇(a1-1),可以使用1种或2种以上,例如可举出聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇、聚烯烃多元醇等,优选可举出聚酯多元醇、聚碳酸酯多元醇。
作为上述聚醚多元醇,可举出根据需要使用具有2个以上活性氢原子的化合物中的1种或2种以上作为引发剂使环氧烷加成聚合(开环聚合)而得到的聚醚多元醇等。
作为上述引发剂,例如可举出乙二醇、二乙二醇、三乙二醇、三亚甲基二醇、1,2-丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇等直链状二元醇;新戊二醇等支链状二元醇;甘油、三羟甲基乙烷、三羟甲基丙烷、邻苯三酚等三元醇;山梨糖醇、蔗糖、乌头糖等多元醇;乌头酸、偏苯三酸、连苯三甲酸等三元羧酸;磷酸;乙二胺、二亚乙基三胺等多元胺;三异丙醇胺;二羟基苯甲酸、羟基邻苯二甲酸等酚酸;1,2,3-丙三硫醇等。
作为上述环氧烷,例如可举出环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯、环氧氯丙烷、四氢呋喃等。
作为上述聚醚多元醇,优选使用通过使四氢呋喃与上述引发剂进行加成聚合(开环聚合)而得到的聚氧四亚甲基二醇。
作为上述聚酯多元醇,例如可举出使分子量50以上且300以下的多元醇与多元羧酸进行酯化反应而得到的聚酯多元醇;使ε-己内酯等环状酯化合物发生开环聚合反应而得到的聚酯多元醇;它们的共聚聚酯多元醇等。
作为上述分子量50以上且300以下的多元醇,可以使用1种或2种以上,例如可举出乙二醇、丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、3-甲基-1,5-戊二醇、二乙二醇、二丙二醇、新戊二醇、1,3-丁二醇等碳原子数2以上且6以下的脂肪族多元醇;1,4-环己烷二醇、环己烷二甲醇等含脂环式结构的多元醇;双酚A、双酚F等双酚化合物和它们的环氧烷加成物等含芳香族结构的多元醇等。
作为上述多元羧酸,可举出琥珀酸、己二酸、癸二酸、十二烷二甲酸等脂肪族多元羧酸;对苯二甲酸、间苯二甲酸、邻苯二甲酸、萘二甲酸等芳香族多元羧酸;以及上述脂肪族多元羧酸和芳香族多元羧酸的酸酐或成酯性衍生物等。
作为上述聚碳酸酯多元醇,例如可举出碳酸酯与多元醇的反应产物;碳酰氯与双酚A等的反应产物等。
作为上述碳酸酯,例如可举出碳酸甲酯、碳酸二甲酯、碳酸乙酯、碳酸二乙酯、环碳酸酯、碳酸二苯酯等。
作为能够与上述碳酸酯反应的多元醇,例如可举出:作为上述低分子量多元醇而例示的多元醇;聚醚多元醇(聚乙二醇、聚丙二醇等)、聚酯多元醇(聚六亚甲基己二酸酯等)等高分子量多元醇(重均分子量500以上且5000以下)等。
作为上述聚烯烃多元醇,例如可举出聚异丁烯多元醇、加氢(氢化)聚丁二烯多元醇、加氢(氢化)聚异戊二烯多元醇等。
上述高分子量多元醇(a1-1)可以包含除了聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇和聚烯烃多元醇以外的高分子量多元醇。
上述高分子量多元醇(a1-1)中所含的聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇和聚烯烃多元醇(优选聚醚多元醇、聚酯多元醇和聚碳酸酯多元醇)的合计含有率在上述高分子量多元醇(a1-1)中优选为30质量%以上,更优选为40质量%以上,优选为100质量%以下。
上述高分子量多元醇(a1-1)的含有率在上述多元醇(a1)中优选为70质量%以上,更优选为80质量%以上,进一步优选为85质量%以上,优选为98质量%以下,更优选为95质量%以下,进一步优选为90质量%以下。
上述低分子量多元醇(a1-2)表示分子量小于500的多元醇,该低分子量多元醇(a1-2)的分子量优选为480以下,更优选为400以下,进一步优选为300以下。
在本说明书中,上述低分子量多元醇(a1-2)的分子量使用基于该低分子量多元醇(a1-2)的分子式作为化学式量算出的值。
上述低分子量多元醇(a1-2)中所含的羟基的数量为2以上,优选为10以下,更优选为6以下,进一步优选为4以下。
作为上述低分子量多元醇(a1-2),可以使用1种或2种以上,例如可举出乙二醇、二乙二醇、1,2-丙二醇、二丙二醇、新戊二醇、2一丁基-2-乙基-1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、3-甲基-1,5-戊二醇、1,4-环己烷二醇、1,6-己二醇、环己烷二甲醇等直链状或支链状的亚烷基二醇等。
上述亚烷基二醇的含有率在上述低分子量多元醇(a1-2)中优选为50质量%以上,更优选为60质量%以上,进一步优选为70质量%以上,优选为100质量%以下。
相对于上述高分子量多元醇(a1-1)100质量份,上述低分子量多元醇(a1-2)的含量优选为1质量份以上,更优选为2质量份以上,进一步优选为4质量份以上,优选为30质量份以下,更优选为20质量份以下,进一步优选为15质量份以下。
上述高分子量多元醇(a1-1)和低分子量多元醇(a1-2)可以具有羧基和磺酸基等酸基;取代或未取代的氨基等碱性基团等,也可以不具有。
需要说明的是,作为上述化合物(B),在使用具有后述式(2)所示的单元的化合物的情况下,上述多元醇(a1)可以为高分子量多元醇(a1-1)和/或低分子量多元醇(a1-2)。
作为上述多异氰酸酯(a2),可以使用1种或2种以上,例如可举出4,4’-二苯基甲烷二异氰酸酯、2,4’-二苯基甲烷二异氰酸酯、碳二亚胺改性二苯基甲烷二异氰酸酯、粗制二苯基甲烷二异氰酸酯、苯二异氰酸酯、甲苯二异氰酸酯、萘二异氰酸酯、苯二亚甲基二异氰酸酯、四甲基苯二亚甲基二异氰酸酯等芳香族多异氰酸酯;六亚甲基二异氰酸酯、赖氨酸二异氰酸酯等脂肪族多异氰酸酯;环己烷二异氰酸酯、氢化苯二亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、二环己基甲烷二异氰酸酯等具有脂环式结构的多异氰酸酯(以下,有时将具有脂环式结构简称为“脂环式”。)等。
上述多异氰酸酯(a2)中所含的异氰酸酯基与上述多元醇(a1)中所含的羟基的摩尔比(NCO/OH)优选为0.9以上,更优选为0.95以上,优选为3以下,更优选为2以下。
上述氨基甲酸酯预聚物(A)可以通过使上述多元醇(a1)与上述多异氰酸酯(a2)反应而制造。根据需要,也可以进行进一步加成扩链剂(a3)的扩链反应,对上述多元醇(a1)与上述多异氰酸酯(a2)的反应产物进一步加成扩链剂(a3)而成的加成物也包括在上述氨基甲酸酯预聚物(A)中。
作为上述扩链剂(a3),可以使用1种或2种以上,例如可以使用多元胺化合物、肼化合物、其他含活性氢原子的化合物等。
作为上述多元胺化合物,可以使用1种或2种以上,例如可举出乙二胺、1,2-丙二胺、1,6-六亚甲基二胺、哌嗪、2,5-二甲基哌嗪、异佛尔酮二胺、4,4’-二环己基甲烷二胺、3,3’-二甲基-4,4’-二环己基甲烷二胺、1,4-环己烷二胺等二元胺;N-羟基甲基氨基乙胺、N-羟基乙基氨基乙胺、N-羟基丙基氨基丙胺、N-乙基氨基乙胺、N-甲基氨基丙胺;二亚乙基三胺、二亚丙基三胺、三亚乙基四胺等;聚氧乙烯二胺、聚氧丙烯二胺、聚氧四亚甲基二胺、聚氧乙烯聚氧丙烯二胺等聚氧化烯二胺(重均分子量200~5000)。
作为上述肼化合物,可以使用1种或2种以上,例如可举出肼、N,N’-二甲基肼、1,6-六亚甲基双肼;琥珀酸二酰肼、己二酸二酰肼、戊二酸二酰肼、癸二酸二酰肼、间苯二甲酸二酰肼;β-氨基脲丙酰肼等。
作为上述其他含活性氢的化合物,可以使用1种或2种以上,例如可举出乙二醇、二乙二醇、三乙二醇、丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、六亚甲基二醇、蔗糖、亚甲基二醇、甘油、山梨糖醇等二醇;双酚A、4,4’-二羟基联苯、4,4’-二羟基二苯基醚、4,4’-二羟基二苯基砜、氢化双酚A、对苯二酚等酚和水等,可以在本发明的水性树脂组合物的保存稳定性不会降低的范围内使用。
相对于上述多元醇(a1)100质量份,上述扩链剂(a3)优选为2质量份以上,更优选为3质量份以上,进一步优选为5质量份以上,优选为30质量份以下,更优选为25质量份以下,进一步优选为20质量份以下。
上述氨基甲酸酯预聚物(A)的重均分子量优选为250以上,更优选为750以上,进一步优选为1000以上,优选为10000以下,更优选为8000以下,进一步优选为5000以下。
在使上述多元醇(a1)、多异氰酸酯和根据需要使用的扩链剂(a3)反应时,可以使反应溶剂共存,也可以不共存。
作为上述反应溶剂,可以使用1种或2种以上,可举出丙酮、甲乙酮等酮溶剂;四氢呋喃、二氧六环等醚溶剂;乙酸乙酯、乙酸丁酯等乙酸酯溶剂;乙腈等腈溶剂;二甲基甲酰胺、N-甲基吡咯烷酮等酰胺溶剂等。上述反应溶剂可以在上述氨基甲酸酯预聚物(A)的制造过程或制造后通过减压蒸馏除去等方法而将其一部分或全部除去。
在上述反应时,反应温度可以设为50℃以上且150℃以下。
上述化合物(B)由式(1)表示。
[化学式3]
[式(1)中,
R1各自独立地表示单键或碳原子数1~10的烃基。
R2表示碳原子数1~50的烃基,上述烃基中所含的-CH2-可以被取代成-O-。
L1表示-O-CO-O-。]
作为R1所示的烃基,优选直链状或支链状的脂肪族烃基。
R1所示的烃基的碳原子数优选为1~5,更优选为1~3。
作为R2所示的烃基,优选直链状或支链状的脂肪族烃基。
另外,R2所示的烃基的碳原子数优选为1~20,更优选为1~5,进一步优选为1~3。
在R2所示的烃基中所含的-CH2-被取代成-O-的情况下,该经取代的基团优选为下式所示的基团。
[化学式4]
[式(2)中,R3表示碳原子数1~8的亚烷基。]
作为R3所示的亚烷基,可以为直链状或支链状中的任一种,可举出亚甲基、亚乙基、亚丙基、亚丁基、戊烷二基等。上述R3所示的亚烷基的碳原子数优选为2~5,更优选为2~3。
作为上述化合物(B),可举出下式所示的化合物等。式中,n表示1~20的整数。
[化学式5]
相对于氨基甲酸酯预聚物(A)100质量份,上述化合物(B)优选为2质量份以上,更优选为4质量份以上,进一步优选为5质量份以上,优选为60质量份以下,更优选为50质量份以下,进一步优选为40质量份以下。
上述氨基甲酸酯预聚物(A)与上述化合物(B)的反应产物(I)可以具有异氰酸酯基,也可以不具有异氰酸酯基。
上述反应产物(I)的重均分子量优选为400以上,更优选为500以上,进一步优选为600以上,优选为20000以下,更优选为10000以下,进一步优选为5000以下。
在使上述氨基甲酸酯预聚物(A)与上述化合物(B)反应时,可以使催化剂共存。作为上述催化剂,可举出三乙胺、三丁胺、二氮杂双环十一碳烯、三亚乙基二胺、吡啶、羟基吡啶等胺催化剂;四丁基锡、二月桂酸二丁基锡等有机金属催化剂等。相对于上述氨基甲酸酯预聚物(A)和上述化合物(B)的合计100质量份,上述催化剂优选为0.001质量份以上且0.1质量份以下。
在使上述氨基甲酸酯预聚物(A)与上述化合物(B)反应时,可以使反应溶剂共存。作为上述反应溶剂,可以使用1种或2种以上,可举出丙酮、甲乙酮等酮溶剂;四氢呋喃、二氧六环等醚溶剂;乙酸乙酯、乙酸丁酯等乙酸酯溶剂;乙腈等腈溶剂;二甲基甲酰胺、N-甲基吡咯烷酮等酰胺溶剂等。上述反应溶剂可以在上述反应产物(I)的制造过程或制造后通过减压蒸馏除去等方法将其一部分或全部除去。
使上述氨基甲酸酯预聚物(A)与上述化合物(B)反应时的反应温度优选为20~140℃,更优选为40~80℃。
与上述反应产物(I)反应的上述多元胺化合物(II)为具有2个以上取代或未取代的氨基(优选未取代的氨基)的化合物,上述多元胺化合物(II)中所含的氨基(优选未取代的氨基)的个数优选为2个以上,优选为10个以下,更优选为5个以下,进一步优选为3个以下。
上述多元胺化合物(II)的分子量优选为100以上,优选为1000以下,更优选为5000以下,进一步优选为2000以下。
上述多元胺化合物(II)的分子量使用基于该多元胺化合物(II)的分子式作为化学式量算出的值。
作为多元胺化合物(II),可以使用1种或2种以上,例如可举出乙二胺、1,2-丙二胺、1,3-丙二胺、1,4-四亚甲基二胺、1,6-六亚甲基二胺、1,8-八亚甲基二胺、1,10-十亚甲基二胺、1,12-十二亚甲基二胺、N-乙基氨基乙胺、N-甲基氨基丙胺、二亚乙基三胺、二亚丙基三胺、三亚乙基四胺等脂肪族多元胺;异佛尔酮二胺、降冰片二胺、1,6-环己烷二胺、4,4’-二环己基甲烷二胺、3,3’-二甲基-4,4’-二环己基甲烷二胺、1,4-环己烷二胺等脂环式二胺;哌嗪、2,5-二甲基哌嗪、2,5-二氨基吡啶等具有杂环结构的二胺(以下,有时将具有杂环结构的情况简称为“杂环式”。);苯二胺、甲苯二胺、苯二甲胺等芳香族多元胺;N-羟基甲基氨基乙胺、N-羟基乙基氨基乙胺、N-羟基丙基氨基丙胺等具有羟基的脂肪族多元胺等。
上述多元胺化合物(II)相对于上述反应产物(I)100质量份优选为1质量份以上,更优选为2质量份以上,进一步优选为4质量份以上,优选为95质量份以下,更优选为90质量份以下,进一步优选为85质量份以下。
作为上述反应产物(I)与上述多元胺化合物(II)的反应产物的本发明的有机聚合物的重均分子量优选为10000以上,更优选为15000以上,进一步优选为20000以上,优选为1000000以下,更优选为500000以下,进一步优选为200000以下。
本发明的有机聚合物的羟值优选为5mgKOH/g以上,更优选为10mgKOH/g以上,进一步优选为15mgKOH/g以上,优选为250mgKOH/g以下,更优选为200mgKOH/g以下,进一步优选为150mgKOH/g以下。
在本说明书中,羟值可以使用氢氧化钾标准液,按照JIS K1557-1(2007)A法进行测定。
在使上述反应产物(I)与上述多元胺化合物(II)反应时,可以使反应溶剂共存。作为上述反应溶剂,可以使用1种或2种以上,例如可举出甲乙酮、甲基正丙基酮、甲基异丁基酮、二乙基酮、丙酮、环己酮等酮溶剂;甲酸甲酯、甲酸乙酯、甲酸丙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯等酯溶剂;四氢呋喃、二氧六环、乙二醇单甲醚、乙二醇二甲醚、丙二醇甲醚、二乙二醇单甲醚、二乙二醇二甲醚等醚溶剂;甲苯、二甲苯等芳香族溶剂;二甲基甲酰胺等酰胺溶剂;二甲基亚砜;全氯乙烯、三氯乙烯等卤代烃溶剂;甲醇、乙醇、丙醇、丁醇、乙二醇、丙二醇等醇溶剂等。
在使上述反应产物(I)与上述多元胺化合物(II)反应时,可以使催化剂共存。作为该催化剂,可举出与可以在使上述氨基甲酸酯预聚物(A)与上述化合物(B)反应时共存的催化剂相同的催化剂。可举出十一碳烯、三亚乙基二胺、吡啶、羟基吡啶等胺催化剂;四丁基锡、二月桂酸二丁基锡等有机金属催化剂等。上述催化剂相对于上述反应产物(I)和上述多元胺化合物(II)的合计100质量份优选为0.01质量份以上且10质量份以下。
上述反应产物(I)与上述多元胺化合物(II)的反应温度优选为40度以上且200度以下,反应时间优选为4小时以上且24小时以下。
包含上述有机聚合物和水性介质的树脂组合物也包含在本发明的技术范围内。
上述有机聚合物的含有率在上述树脂组合物中优选为5质量%以上,更优选为10质量%以上,优选为80质量%以下,更优选为70质量%以下,进一步优选为60质量%以下。
作为上述水性介质,可举出水、亲水性有机溶剂和水与亲水性溶剂的混合溶剂等。作为上述亲水性溶剂,优选能够与水混溶的溶剂,可以使用1种或2种以上,例如可举出甲醇、乙醇、正丙醇、异丙醇、1,2-丙二醇、1,3-丁二醇等醇溶剂;丙酮、甲乙酮等酮溶剂;乙二醇正丁醚、二乙二醇正丁醚、二乙二醇单乙醚乙酸酯、二乙二醇二甲醚、丙二醇甲醚、二丙二醇甲醚、二丙二醇二甲醚、二丙二醇正丁醚、三丙二醇甲醚等二醇醚溶剂;N-甲基-2-吡咯烷酮、N-乙基-2-吡咯烷酮等内酰胺溶剂;N,N-二甲基甲酰胺等酰胺溶剂等,优选醇溶剂。
上述水性介质优选包含水,水的含有率在上述水性介质中优选为50质量%以上,更优选为70质量%以上,进一步优选为80质量%以上,特别优选为90质量%以上,上限为100质量%。作为上述水性介质,优选水或水与亲水性溶剂的混合溶剂,更优选水。
上述水性介质的含有率在上述树脂组合物中优选为30质量%以上,进一步优选为40质量%以上,优选为80质量%以下,更优选为70质量%以下。
上述树脂组合物可以根据需要进一步包含交联剂、表面活性剂、增塑剂、抗静电剂、蜡、光稳定剂、流动调节剂、染料、流平剂、流变控制剂、紫外线吸收剂、抗氧化剂、光催化剂性化合物、无机颜料、有机颜料、体质颜料等各种添加剂等。
相对于上述有机聚合物100质量份,上述添加剂的含有率优选为20质量份以下,更优选为10质量份以下,进一步优选为5质量份以下。
具有基材和作为上述树脂组合物的固化物的涂膜的物品也包含在本发明的技术范围内。
上述涂膜的厚度优选为0.1μm以上,更优选为0.3μm以上,进一步优选为0.5μm以上,优选为100μm以下,更优选为50μm以下,进一步优选为10μm以下。
作为上述基材,可举出金属、塑料及其膜、玻璃、木、木材等。
作为上述金属,例如可举出汽车、家电、建材等用途中使用的镀锌钢板、铝-镀锌钢板、铝板、铝合金板、经磷酸铬酸盐光泽处理的铝板、电磁钢板、铜板、不锈钢板等。
作为塑料基材,通常作为农业用膜、移动电话、家电制品、汽车内外装材料、OA设备等塑料成型品中采用的原材料,可举出聚酯树脂、丙烯腈-丁二烯-苯乙烯树脂(ABS树脂)、聚碳酸酯树脂(PC树脂)、ABS/PC树脂、聚苯乙烯树脂(PS树脂)、聚甲基丙烯酸甲酯树脂(PMMA树脂)、丙烯酸系树脂、聚丙烯树脂、聚乙烯树脂、乙烯-乙酸乙烯酯共聚物树脂(EVA树脂)等,作为塑料膜基材,可以使用聚对苯二甲酸乙二醇酯膜、聚酯膜、聚乙烯膜、聚丙烯膜、TAC(三乙酰纤维素)膜、聚碳酸酯膜、聚氯乙烯膜等。
作为上述物品,例如可举出建筑构件、家电制品、汽车部件、汽车外装材料等。本发明的树脂组合物可以适合用于建筑构件、家电制品、汽车部件、汽车外装材料、涂布剂、粘接剂、医疗器具等各种工业用途。
实施例
以下,列举实施例更具体地说明本发明。
实施例1
使聚四亚甲基二醇(PTMG)(平均分子量1000)475质量份、乙二醇31质量份和异佛尔酮二异氰酸酯222质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式6]
接下来,将反应液冷却至80℃,在乙醇溶剂中与六亚甲基二胺58质量份反应,由此得到羟基氨基甲酸酯组合物(1)。该羟基氨基甲酸酯组合物(1)中所含的聚合物的羟基量为61mgKOH/g。
实施例2
使PTMG(平均分子量1000)475质量份、六亚甲基二醇59质量份和苯二亚甲基二异氰酸酯188质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式7]
接下来,将反应液冷却至80℃,在N-甲基吡咯烷酮溶剂中与苯二甲胺68质量份反应,由此得到羟基氨基甲酸酯组合物(1)。该羟基氨基甲酸酯组合物(1)中所含的聚合物的羟基量为61mgKOH/g。
实施例3
使聚酯多元醇(使乙二醇/新戊二醇/对苯二甲酸/间苯二甲酸反应而合成的多元醇:平均分子量950)451质量份、乙二醇31质量份、苯二亚甲基二异氰酸酯188质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式8]
接下来,将反应液冷却至80℃,在乙醇溶剂中与乙二胺30质量份反应,由此得到羟基氨基甲酸酯组合物(3)。该羟基氨基甲酸酯组合物(3)中所含的聚合物的羟基量为68mgKOH/g。
实施例4
使聚碳酸酯多元醇(宇部兴产株式会社制“UH-200”,羟值56±5mgKOH/g,平均分子量2000)950质量份、六亚甲基二醇59质量份、苯二亚甲基二异氰酸酯188质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
接下来,将反应液冷却至80℃,在乙醇溶剂中与苯二甲胺68质量份反应,由此得到羟基氨基甲酸酯组合物(4)。该羟基氨基甲酸酯组合物(3)中所含的聚合物的羟基量为40mgKOH/g。
实施例5
使聚碳酸酯多元醇(宇部兴产株式会社制“UH-200”,羟值56±5mgKOH/g,平均分子量2000)950质量份、六亚甲基二醇59质量份、苯二亚甲基二异氰酸酯188质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式9]
接下来,将反应液冷却至80℃,在乙醇溶剂中与聚氧化烯二胺(HUNTSMAN制“JEFFAMINE D-2000”)1000质量份反应,由此得到羟基氨基甲酸酯组合物(5)。该羟基氨基甲酸酯组合物(3)中所含的聚合物的羟基量为24mgKOH/g。
实施例6
使PTMG(平均分子量850)21质量份、乙二醇8质量份和苯二亚甲基二异氰酸酯118质量份在反应容器中反应后,使下式所示的化合物124质量份在100℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式10]
接下来,将反应液冷却至80℃,在乙醇溶剂中与苯二甲胺68质量份反应,由此得到羟基氨基甲酸酯组合物(5)。该羟基氨基甲酸酯组合物(3)中所含的聚合物的羟基量为155mgKOH/g。
实施例7
使下式所示的化合物124质量份和苯二亚甲基二异氰酸酯94质量份在反应容器中在50℃下反应,由此得到在分子末端具有环状碳酸酯基的氨基甲酸酯预聚物。
[化学式11]
接下来,将反应液冷却至80℃,在异丙醇溶剂中与苯二甲胺68质量份反应,由此得到羟基氨基甲酸酯组合物(5)。该羟基氨基甲酸酯组合物(3)中所含的聚合物的羟基量为195mgKOH/g。
比较例1
在反应容器中使聚酯多元醇(株式会社kuraray制“P-1010”475质量份、六亚甲基二异氰酸酯168质量份反应后,使下式所示的化合物124质量份在100下反应,由此得到氨基甲酸酯预聚物。
[化学式12]
接下来,将反应液冷却至80℃,加入通过使双酚A二缩水甘油醚与CO2反应而得到的化合物214质量份,进一步加入六亚甲基二胺118质量份,在乙醇溶剂中反应,由此得到羟基氨基甲酸酯组合物(X1)。该羟基氨基甲酸酯组合物(X1)中所含的聚合物的羟基量为131mgKOH/g。
[耐剥离性的评价方法]
在基材的表面以干燥时的膜厚成为约1μm的方式涂布实施例和比较例中得到的羟基氨基甲酸酯组合物,在150下加热5分钟,由此在上述基材的表面制作涂膜(底涂层)。在通过上述方法制作的试验板的底涂层的表面贴附NICHIBAN株式会社制的24mm宽的粘合带。接下来,将上述粘合带沿与上述涂膜垂直的方向拉拽而将上述粘合带从涂膜的表面剥离,按照下述评价基准来目视评价此时的上述涂膜的表面的状态。
◎:涂膜完全没有从构成试验板的基材表面剥离。
O:从构成试验板的基材表面剥离了极少一部分涂膜,但该剥离的范围相对于构成试验板的被膜的总面积小于10%。
△:相对于构成试验板的涂膜的面积为10%以上且小于50%的范围的底涂层从构成试验板的基材表面剥离。
×:相对于构成试验板的涂膜的总面积为50%以上的范围的底涂层从构成试验板的基材表面剥离。
[表1]
实施例1~7为本发明的实施例,相对于金属基材的耐剥离性良好。比较例1是不包含低分子量多元醇作为形成氨基甲酸酯预聚物的多元醇的例子,相对于金属基材的耐剥离性不充分。
Claims (5)
1.一种有机聚合物,其特征在于,其为具有异氰酸酯基的氨基甲酸酯预聚物(A)和式(1)所示的化合物(B)的反应产物(I)与多元胺化合物(II)的反应产物,
所述氨基甲酸酯预聚物(A)为多元醇(a1)与多异氰酸酯(a2)的反应产物,
所述多元醇(a1)包含高分子量多元醇(a1-1)和低分子量多元醇(a1-2),
所述高分子量多元醇(a1-1)的重均分子量为500以上,所述低分子量多元醇(a1-2)的分子量小于500,
所述低分子量多元醇(a1-2)包含亚烷基二醇,
式(1)中,
R1各自独立地表示单键或碳原子数1~10的烃基,
R2表示碳原子数1~50的烃基,所述烃基中所含的-CH2-任选被取代成-O-,
L1表示-O-CO-O-。
2.根据权利要求1所述的有机聚合物,其中,所述多元醇中,低分子量多元醇的含有率为0.1质量%以上。
3.一种树脂组合物,其包含权利要求1或2所述的有机聚合物和水性介质。
4.一种物品,其具有基材和涂膜,所述涂膜为权利要求3所述的树脂组合物的固化物。
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