CN110402192A - 成型体的制造方法 - Google Patents
成型体的制造方法 Download PDFInfo
- Publication number
- CN110402192A CN110402192A CN201880017995.9A CN201880017995A CN110402192A CN 110402192 A CN110402192 A CN 110402192A CN 201880017995 A CN201880017995 A CN 201880017995A CN 110402192 A CN110402192 A CN 110402192A
- Authority
- CN
- China
- Prior art keywords
- methyl
- acrylate
- formed body
- resin
- manufacturing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- -1 (methyl) acryloyl group Chemical group 0.000 claims abstract description 73
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 150000002148 esters Chemical group 0.000 claims abstract description 39
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000005452 bending Methods 0.000 claims abstract description 23
- 230000008569 process Effects 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 21
- 239000000758 substrate Substances 0.000 claims abstract description 21
- 238000003754 machining Methods 0.000 claims abstract description 19
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract description 18
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 10
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 55
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 37
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 31
- 239000000377 silicon dioxide Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 235000012239 silicon dioxide Nutrition 0.000 claims description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- 238000007711 solidification Methods 0.000 claims description 6
- 230000008023 solidification Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 abstract description 3
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- 238000006243 chemical reaction Methods 0.000 description 20
- 239000002253 acid Substances 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- 238000005299 abrasion Methods 0.000 description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 11
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 10
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000005056 polyisocyanate Substances 0.000 description 10
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- 238000003786 synthesis reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000012790 confirmation Methods 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
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- 239000000178 monomer Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- 238000010422 painting Methods 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 229920005372 Plexiglas® Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本发明提供一种成型体的制造方法,其特征在于,具有如下工序:工序1,将含有脂环式氨基甲酸酯(甲基)丙烯酸酯的组合物涂覆于热塑性树脂基材而得到涂覆物;工序2,获得具有固化物层的层叠体,所述固化物层是对所得涂覆物照射活性能量射线并将前述组合物固化而得到的;以及工序3,将所得层叠体进行弯曲加工而得到成型体,前述脂环式氨基甲酸酯(甲基)丙烯酸酯分别具有:式(A)所示的具有脂环结构的结构、以及2个以上式(B)所示的具有(甲基)丙烯酰基的基团,进而,聚合性双键当量为100~1000g/mol。
Description
技术领域
本发明涉及一种成型体的制造方法,其特征在于,具有良好的硬涂性且在固化后进行弯曲加工。
背景技术
一直以来,在仪表罩等汽车内饰品、车棚或高速公路的隔音墙等建筑材料、汽车等的树脂窗玻璃、办公自动化设备等的显示面的构成部件中使用树脂制的成型体。这种构件为了耐受室外用途中的使用而必须是表层涂布了具有耐磨耗性、耐候性的耐候硬涂层的硬涂层叠体。
硬涂层叠体不仅适用于保护对象物的平面部,还适用于保护对象物的曲面部。但是,硬涂层为了获得其硬度而较脆,因此在固化后难以进行弯曲加工。因而,以往仅采取对基材实施弯曲加工而得到成型体后将硬涂层进行层叠的成型方式,在生产率和成本方面存在课题。因此,寻求具有硬涂性且即使在固化后也能够弯曲加工的成型体的制造方法。
作为该课题的解决手段,专利文献1公开了向硬涂层与基材之间导入具有特定Tg的层的三层结构的层叠体。但是,在制造层叠体时必须制成3层以上的构成,在涂装时的生产率方面存在难度,因此,期望利用包括基材在内的两层构成来兼顾耐磨耗性和成型性。
现有技术文献
专利文献
专利文献1:日本特开2014-688号公报
发明内容
发明要解决的问题
本发明的课题在于,提供具有硬涂性且即使在固化后也能够进行弯曲加工的成型体的制造方法。
用于解决问题的方案
本发明人等进行了深入研究,结果还发现:通过下述成型体的制造方法能够解决上述课题,所述方法的特征在于,具有如下工序:工序1,将包含具有脂环骨架且聚合性双键当量(g/mol)为100~1000的脂环式氨基甲酸酯(甲基)丙烯酸酯的组合物涂覆于热塑性树脂基材而得到涂覆物;工序2,获得具有固化物层的层叠体,所述固化物层是对所得涂覆物照射活性能量射线并将前述组合物固化而得到的;以及工序3,将所得层叠体进行弯曲加工而得到成型体。
发明的效果
通过本发明,能够制造硬涂性优异的成型体。尤其是,由于对基材直接涂覆硬涂层而得到涂覆物后,对涂覆物照射活性能量射线而得到层叠体后也能够进行加工,因此生产率特别优异,因而产业上的可利用性优异。
具体实施方式
本发明提供一种成型体的制造方法,其特征在于,具有如下工序:工序1,将含有脂环式氨基甲酸酯(甲基)丙烯酸酯的组合物涂覆于热塑性树脂基材而得到涂覆物;工序2,获得具有固化物层的层叠体,所述固化物层是对所得涂覆物照射活性能量射线并将前述组合物固化而得到的;以及工序3,将所得层叠体进行弯曲加工而得到成型体,前述脂环式氨基甲酸酯(甲基)丙烯酸酯分别具有:式(A)所示的具有脂环结构的结构、以及2个以上式(B)所示的具有(甲基)丙烯酰基的基团,进而,聚合性双键当量为100~1000g/mol。
<工序1>
本发明的工序1是将含有脂环式氨基甲酸酯(甲基)丙烯酸酯的组合物涂覆于热塑性树脂基材而得到涂覆物的工序。
(脂环式氨基甲酸酯(甲基)丙烯酸酯)
本发明的组合物含有脂环式氨基甲酸酯(甲基)丙烯酸酯作为必须成分。
本发明的脂环式氨基甲酸酯(甲基)丙烯酸酯的特征在于,分别具有式(A)所示的具有脂环结构的结构、以及2个以上式(B)所示的具有(甲基)丙烯酰基的基团,进而,聚合性双键当量为100~1000g/mol。
(式(A)中,X为下述式(1)所示的脂环结构之中的至少1个;Y1、Y2各自独立地为直接键合、碳原子数1~10的烃基、氨基甲酸酯键、醚键、酰胺键或羰基;n表示1~6的整数。)
(式(1)中,脂环结构分别任选具有或不具有取代基。)
(通式(B)中,R1为直接键合或2价的连接基团;Y为直接键合或碳原子;R2为直接键合、碳原子数1~3的烃基或羰基;R3为氢原子或甲基;m表示1~3的整数。)
前述通式(B)中,作为2价的连接基团,可列举出碳原子数1~10的烃基、酰胺键、醚键、羰基、以及它们的组合。
Y为直接键合或碳原子。对于碳原子而言,氢原子任选被取代,作为取代基,可列举出碳原子数1~10的烃基。
本发明的脂环式氨基甲酸酯(甲基)丙烯酸酯中,聚合性双键当量为100~1000g/mol。这是因为:如果为100以下,则虽表现出耐磨耗性但表现不出耐弯曲性,如果为1000以上,则虽表现出耐弯曲性但表现不出耐磨耗性。优选为100~850,如果为该范围,则能够兼顾耐磨耗性和耐弯曲性,故而优选。特别优选为100~650。
本发明的聚合性双键当量是指:将具有聚合性双键的分子的平均重量记作M,将具有聚合性双键的分子中的平均双键数记作N时,使用下式计算导出的值。
聚合性双键当量=M/N
作为本发明的脂环式氨基甲酸酯(甲基)丙烯酸酯,可列举出例如以下通式(I)~(VI)所示的结构。
对于本发明的脂环式氨基甲酸酯(甲基)丙烯酸酯,作为优选的结构,可列举出以下的结构。
(具有聚合性双键的化合物)
本发明的组合物中,除了含有本发明的脂环式氨基甲酸酯(甲基)丙烯酸酯之外,也可以含有具有聚合性双键的化合物。作为具有聚合性双键的化合物,只要具有聚合性双键就没有特别限定,可以为单体也可以为低聚物,可以为大分子单体也可以为聚合物。
作为聚合性双键,可列举出例如乙烯基、(甲基)丙烯酰基等,具有这些基团的化合物为具有聚合性双键的化合物。作为具有聚合性双键的化合物,可列举出例如乙烯基系化合物、(甲基)丙烯酰基系化合物等。
作为乙烯基系化合物,可列举出例如苯乙烯、α-甲基苯乙烯、乙烯基甲苯、氯苯乙烯等苯乙烯系单体;乙酸乙烯酯等乙烯基酯;(甲基)丙烯酰胺;(甲基)丙烯腈;N-甲氧基甲基丙烯酰胺、N-乙氧基甲基丙烯酰胺等N-烷氧基取代(甲基)丙烯酰胺;不饱和碱性单体;N-苯基马来酰亚胺、N-环己基马来酰亚胺、N-异丙基马来酰亚胺等马来酰亚胺系单体等。
作为(甲基)丙烯酰基系化合物,可列举出单官能(甲基)丙烯酸酯和多官能(甲基)丙烯酸酯。
作为单官能(甲基)丙烯酸酯,可列举出例如(甲基)丙烯酸羟基乙酯、(甲基)丙烯酸羟基丙酯、(甲基)丙烯酸羟基丁酯、己内酯改性羟基(甲基)丙烯酸酯(例如DaicelChemical Industries,Ltd.制的商品名“Placcel”)、由邻苯二甲酸和丙二醇获得的聚酯二醇的单(甲基)丙烯酸酯、由琥珀酸和丙二醇获得的聚酯二醇的单(甲基)丙烯酸酯、聚乙二醇单(甲基)丙烯酸酯、聚丙二醇单(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、(甲基)丙烯酸2-羟基-3-(甲基)丙烯酰氧基丙酯、各种环氧酯的(甲基)丙烯酸加成物等含有羟基的(甲基)丙烯酸酯;(甲基)丙烯酸、巴豆酸、衣康酸、马来酸、富马酸等含有羧基的乙烯基单体;乙烯基磺酸、苯乙烯磺酸、(甲基)丙烯酸磺基乙酯等含有磺酸基的乙烯基单体;2-(甲基)丙烯酰氧基乙基酸式磷酸酯、2-(甲基)丙烯酰氧基丙基酸式磷酸酯、2-(甲基)丙烯酰氧基-3-氯-丙基酸式磷酸酯、2-甲基丙烯酰氧基乙基苯基磷酸等酸式磷酸酯系乙烯基单体;N-羟甲基(甲基)丙烯酰胺等具有羟甲基的乙烯基单体等。
作为多官能单体和多官能低聚物,可列举出1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、利用环氧乙烷进行了改性的甘油三(甲基)丙烯酸酯、利用环氧丙烷进行了改性的甘油三(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、羟基特戊酸改性三羟甲基丙烷三(甲基)丙烯酸酯、利用环氧乙烷进行了改性的三羟甲基丙烷三(甲基)丙烯酸酯、利用环氧丙烷进行了改性的三羟甲基丙烷三(甲基)丙烯酸酯、利用环氧乙烷进行了改性的磷酸三(甲基)丙烯酸酯、季戊四醇乙氧基四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、二季戊四醇三(甲基)丙烯酸酯、二季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇四(甲基)丙烯酸酯、三季戊四醇五(甲基)丙烯酸酯、三季戊四醇六(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、利用环氧乙烷进行了改性的二季戊四醇六(甲基)丙烯酸酯、利用环氧丙烷进行了改性的二季戊四醇六(甲基)丙烯酸酯、使异氰酸酯化合物与醇系化合物反应而得的氨基甲酸酯(甲基)丙烯酸酯化合物、利用多元醇与(甲基)丙烯酸和多官能性羧酸的缩合反应而合成的聚酯(甲基)丙烯酸酯化合物、利用双酚型环氧树脂或酚醛清漆型环氧树脂与(甲基)丙烯酸的加成反应而合成的环氧(甲基)丙烯酸酯化合物等。
这些具有聚合性双键的化合物可以单独使用,也可以组合使用2种以上。
(具有异氰脲酸酯骨架且聚合性双键当量为100~1000g/mol的含异氰脲酸酯骨架的(甲基)丙烯酸酯)
此外,在本发明的组合物中,具有聚合性双键的化合物优选含有:具有异氰脲酸酯骨架且聚合性双键当量为100~1000g/mol的含异氰脲酸酯骨架的(甲基)丙烯酸酯。通过含有本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯,从而使耐磨耗性和耐弯曲性进一步提高。
本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯的特征在于,其具有异氰脲酸酯骨架且聚合性双键当量为100~1000g/mol。聚合性双键当量是指:将具有聚合性双键的分子的平均重量记作M,将具有聚合性双键的分子中的平均双键数记作N时,使用下式计算导出的值。
聚合性双键当量=M/N
作为本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯,是下述通式(1)所示的含异氰脲酸环的三(甲基)丙烯酸酯化合物。
(式(1)中,A1、A2和A3表示丙烯酰基(CH2=CH-CO-)、利用己内酯进行了改性的丙烯酰基[(CH2=CH-CO(O(CH2)5C=O)a-),a为1以上的整数]、氢原子或烷基,这些之中的至少2个是丙烯酰基或利用己内酯进行了改性的丙烯酰基;B1、B2和B3表示氧亚烷基或聚氧亚烷基。)
这些含异氰脲酸酯骨架的(甲基)丙烯酸酯可以单独使用,也可以组合使用2种以上。
作为本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯,具体而言,可列举出三(2-丙烯酰氧基乙基)异氰脲酸酯、三(2-丙烯酰氧基丙基)异氰脲酸酯、每1个分子利用1个己内酯进行了改性的三(2-丙烯酰氧基乙基)异氰脲酸酯(商品名“ARONIX M-325”、TOAGOSEI CO.,LTD.制)、每1个分子利用3个己内酯进行了改性的三(2-丙烯酰氧基乙基)异氰脲酸酯(商品名“ARONIX M-327”、TOAGOSEI CO.,LTD.制)等。
(含异氰脲酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯)
本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯优选为具有氨基甲酸酯键的含异氰脲酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯。这是因为:利用氨基甲酸酯键,成型性和耐候性进一步提高而不损害耐磨耗性。
特别优选的是:在组合使用具有氨基甲酸酯键的含异氰脲酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯和不具有氨基甲酸酯键的含异氰脲酸酯骨架的(甲基)丙烯酸酯的情况下,成型性与耐候性的平衡优异。
作为本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯为氨基甲酸酯(甲基)丙烯酸酯的情况,具体而言,可列举出使其结构上具有异氰脲酸酯骨架的多异氰酸酯化合物与多元醇反应而得的产物。
作为前述多异氰酸酯化合物,只要在其结构上具有异氰脲酸酯骨架即可,可列举出例如二异氰酸酯的三聚物。作为前述二异氰酸酯,可列举出例如六亚甲基二异氰酸酯、苯二异氰酸酯、甲苯二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯、异佛尔酮二异氰酸酯等。此外,也可以将使这些二异氰酸酯的三聚物与多元醇反应而得到的多异氰酸酯用作前述多异氰酸酯化合物(a1)。作为前述多元醇,可列举出例如2,2,4-三甲基-1,3-戊二醇、1,3-己二醇、1,6-己二醇等脂肪族二醇;聚乙二醇、聚丙二醇、不饱和脂肪族醇的二聚物等。此外,还可以是将前述多元醇进行内酯改性而得的化合物。此外,这些多异氰酸酯化合物可以单独使用,也可以组合使用2种以上。
优选的是:从进一步获得耐磨耗性和耐弯曲性的方面出发,优选包含六亚甲基二异氰酸酯的三聚物。
(内酯改性的含异氰脲酸酯骨架的(甲基)丙烯酸酯)
本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯可以是进行了内酯改性的内酯改性脲酸酯(甲基)丙烯酸酯。通过进行内酯改性,能够进一步提高耐弯曲性,而不损害硬涂性、尤其是耐磨耗性。
作为内酯改性脲酸酯(甲基)丙烯酸酯,可列举出使其结构上具有异氰脲酸酯骨架的多异氰酸酯化合物与内酯改性多元醇反应而得的产物、或者使内酯改性多异氰酸酯与多元醇反应而得的产物。作为前述多异氰酸酯化合物,只要在其结构上具有异氰脲酸酯骨架即可,此外,这些多异氰酸酯化合物可以单独使用,也可以组合使用2种以上。作为前述多元醇,可列举出例如2,2,4-三甲基-1,3-戊二醇、1,3-己二醇、1,6-己二醇等脂肪族二醇;聚乙二醇、聚丙二醇、不饱和脂肪族醇的二聚物等。此外,也可以是将前述多元醇进行内酯改性而得的化合物。此外,这些多异氰酸酯化合物可以单独使用,也可以组合使用2种以上。
优选的是:从进一步获得耐磨耗性和耐弯曲性的方面出发,优选包含六亚甲基二异氰酸酯的三聚物。
(配混量)
在本发明的组合物中,在包含具有聚合性双键的化合物和脂环式氨基甲酸酯(甲基)丙烯酸酯的情况下,在兼顾优异的耐弯曲性和耐磨耗性的方面,相对于具有聚合性双键的化合物和脂环式氨基甲酸酯(甲基)丙烯酸酯的总重量,脂环式氨基甲酸酯(甲基)丙烯酸酯的比例期望为5~100wt%。更优选为10~95wt%,特别优选为20~90wt%。
此外,在本发明的组合物含有含异氰脲酸酯骨架的(甲基)丙烯酸酯的情况下,相对于具有聚合性双键的化合物和脂环式氨基甲酸酯(甲基)丙烯酸酯的总重量,优选为1~95wt%。更优选为5~80wt%,特别优选为10~70wt%。
进而,在本发明的含异氰脲酸酯骨架的(甲基)丙烯酸酯含有含异氰脲酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯的情况下,在含异氰脲酸酯骨架的(甲基)丙烯酸酯的总重量中,含异氰脲酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯的比例优选为5~100wt%。更优选为10~80wt%,特别优选为20~70wt%。
(二氧化硅)
本发明的组合物中,出于提高硬涂性的目的,优选配混二氧化硅。
作为二氧化硅,没有限定,可以使用粉末状的二氧化硅、胶态二氧化硅等公知的二氧化硅微粒。作为市售的粉末状的二氧化硅微粒,可列举出例如NIPPON AEROSIL CO.,LTD.制的AEROSIL50、200;Asahi Glass Co.,Ltd.制的SHIELDEX H31、H32、H51、H52、H121、H122;Nippon Silica Ind.Co.,Ltd.制的E220A、E220;FUJI SILYSIA CHEMICAL LTD.制的SYLYSIA470;日本板硝子株式会社制的SG Flake等。
此外,作为市售的胶态二氧化硅,可列举出例如日产化学工业株式会社制的甲醇硅溶胶、IPA-ST、MEK-ST、NBA-ST、XBA-ST、DMAC-ST、ST-UP、ST-OUP、ST-20、ST-40、ST-C、ST-N、ST-O、ST-50、ST-OL等。
作为二氧化硅,可以使用反应性二氧化硅。作为反应性二氧化硅,可列举出例如反应性化合物修饰二氧化硅。作为反应性化合物,可列举出例如具有疏水性基团的反应性硅烷偶联剂、具有(甲基)丙烯酰基的化合物、具有马来酰亚胺基的化合物、具有缩水甘油基的化合物。
作为利用具有(甲基)丙烯酰基的化合物进行了修饰的市售的粉末状的二氧化硅,可列举出NIPPON AEROSIL CO.,LTD.制的AEROSILRM50、R711等,作为利用具有(甲基)丙烯酰基的化合物进行了修饰的市售的胶态二氧化硅,可列举出日产化学工业株式会社制的MIBK-SD、MIBK-SD-L、MEK-AC、PGM-AC、MIBK-AC等。此外,作为反应性二氧化硅,还可列举出:在利用3-环氧丙氧基丙基三甲氧基硅烷等缩水甘油基进行修饰后,使其与丙烯酸发生加成反应而得的二氧化硅;利用使3-异氰酸酯丙基三乙氧基硅烷与具有羟基和(甲基)丙烯酰基的化合物发生氨基甲酸酯化反应而得的产物进行了修饰的二氧化硅。
前述二氧化硅微粒的形状没有特别限定,可以使用球状、中空状、多孔状、棒状、板状、纤维状或不规则形状的微粒。例如,作为市售的中空状二氧化硅微粒,可以使用日铁矿业株式会社制的SILINAX等。
此外,平均粒径优选为5~200nm的范围。若为5nm以上,则组合物中的无机微粒的分散变得充分,若为200nm以下,则能够保持固化物的充分强度。
作为二氧化硅的配混量,相对于组合物中的脂环式氨基甲酸酯(甲基)丙烯酸酯与具有聚合性双键的化合物的总重量,优选为3~60重量份的配混量。
(其它配混物)
本发明的组合物可以含有其它的配混物。也可以配混例如各种树脂、反应性化合物、催化剂、聚合引发剂、有机填料、无机填料、有机溶剂、无机颜料、有机颜料、体质颜料、粘土矿物、蜡、表面活性剂、稳定剂、流动调节剂、偶联剂、染料、流平剂、流变控制剂、紫外线吸收剂、抗氧化剂、增塑剂等。
作为有机溶剂,可列举出例如酯系溶剂、酮系溶剂、醚系溶剂、脂肪族系溶剂、芳香族系溶剂、醇系溶剂。
具体而言,作为酯系溶剂,可例示出乙酸乙酯、乙酸丙酯、乙酸丁酯,作为酮系溶剂,可例示出丙酮、2-丁酮、甲乙酮、甲基异丁基酮等,作为醚系溶剂,可例示出四氢呋喃、二氧戊环等,作为脂肪族系溶剂,可例示出己烷、环己烷等,作为芳香族系溶剂,可例示出甲苯、二甲苯等,作为醇系溶剂,可例示出乙醇、甲醇、丙醇、丁醇、丙二醇单甲醚等。
此外,为了调整粘度,可以使用液态有机聚合物。液态有机聚合物是指不直接参与固化反应的液态有机聚合物,可列举出例如含羧基的聚合物改性物(FLOWLEN G-900、NC-500:共荣社化学株式会社)、丙烯酸类聚合物(FLOWLEN WK-20:共荣社化学株式会社)、特殊改性磷酸酯的胺盐(HIPLAAD ED-251:楠本化成株式会社)、改性丙烯酸系嵌段共聚物(DISPERBYK2000;BYK-Chemie)等。
作为各种树脂,可以使用热固化性树脂、热塑性树脂。
热固化性树脂是指:通过加热或辐射线、催化剂等的手段而进行固化时,具备实质上不溶且能够变为不融性的特性的树脂。作为其具体例,热固化性树脂是指:通过加热或辐射线、催化剂等手段而进行固化时,具备实质上不溶且能够变为不融性的特性的树脂。作为其具体例,可列举出酚醛树脂、脲树脂、三聚氰胺树脂、苯并胍胺树脂、醇酸树脂、不饱和聚酯树脂、乙烯基酯树脂、对苯二甲酸二烯丙酯树脂、环氧树脂、硅酮树脂、氨基甲酸酯树脂、呋喃树脂、酮树脂、二甲苯树脂、热固化性聚酰亚胺树脂、苯并噁嗪树脂、活性酯树脂、苯胺树脂、氰酸酯酯树脂、苯乙烯-马来酸酐(SMA)树脂等。这些热固化性树脂可以使用1种或组合使用2种以上。
热塑性树脂是指通过加热而能够进行熔融成型的树脂。作为其具体例,可列举出聚乙烯树脂、聚丙烯树脂、聚苯乙烯树脂、橡胶改性聚苯乙烯树脂、丙烯腈-丁二烯-苯乙烯(ABS)树脂、丙烯腈-苯乙烯(AS)树脂、聚甲基丙烯酸甲酯树脂、丙烯酸类树脂、聚氯乙烯树脂、聚偏二氯乙烯树脂、聚对苯二甲酸乙二醇酯树脂、乙烯乙烯醇树脂、乙酸纤维素树脂、离聚物树脂、聚丙烯腈树脂、聚酰胺树脂、聚缩醛树脂、聚对苯二甲酸丁二醇酯树脂、聚乳酸树脂、聚苯醚树脂、改性聚苯醚树脂、聚碳酸酯树脂、聚砜树脂、聚苯硫醚树脂、聚醚酰亚胺树脂、聚醚砜树脂、聚芳酯树脂、热塑性聚酰亚胺树脂、聚酰胺酰亚胺树脂、聚醚醚酮树脂、聚酮树脂、液晶聚酯树脂、氟树脂、间同立构聚苯乙烯树脂、环状聚烯烃树脂等。这些热塑性树脂可以使用1种或组合使用2种以上。
本发明的组合物可以具有除了二氧化硅之外的填料。作为除了二氧化硅之外的填料,可列举出无机填料和有机填料。填料形状没有限定,可列举出颗粒状、板状、纤维状的填料。
作为无机微粒,例如,作为耐热性优异的微粒,为氧化铝、氧化镁、氧化钛、氧化锆等;作为导热优异的微粒,为氮化硼、氮化铝、氧化铝、氧化钛、氧化镁、氧化锌、氧化硅等;作为导电性优异的微粒,为使用了金属单质或合金(例如铁、铜、镁、铝、金、银、铂、锌、锰、不锈钢等)的金属填料和/或金属覆盖填料;作为阻隔性优异的微粒,为云母、粘土、高岭土、滑石、沸石、硅灰石、蒙皂石等矿物等、钛酸钾、硫酸镁、海泡石、硬硅钙石、硼酸铝、碳酸钙、氧化钛、硫酸钡、氧化锌、氢氧化镁;作为折射率高的微粒,为钛酸钡、氧化锆、氧化钛等;作为显示光催化性的微粒,为钛、铈、锌、铜、铝、锡、铟、磷、碳、硫、铈、镍、铁、钴、银、钼、锶、铬、钡、铅等光催化金属、前述金属的复合物、它们的氧化物等;作为耐磨耗性优异的微粒,为氧化铝、氧化锆、氧化镁等的金属、以及它们的复合物和氧化物等;作为导电性优异的微粒,为银、铜等金属、氧化锡、氧化铟等;作为紫外线隔绝优异的微粒,为氧化钛、氧化锌等。
这些无机微粒根据用途适当选择即可,可以单独使用,也可以组合使用多种。此外,上述无机微粒除了具有列举的特性之外,还具有各种特性,因此适当根据用途进行选择即可。
作为无机纤维,除了碳纤维、玻璃纤维、硼纤维、氧化铝纤维、碳化硅纤维等无机纤维之外,可列举出碳纤维、活性炭纤维、石墨纤维、玻璃纤维、碳化钨纤维、碳化硅纤维(silicon carbide fiber)、陶瓷纤维、氧化铝纤维、天然纤维、玄武岩等矿物纤维;硼纤维、氮化硼纤维、碳化硼纤维和金属纤维等。作为上述金属纤维,可列举出例如铝纤维、铜纤维、黄铜纤维、不锈钢纤维、钢丝纤维。
作为有机纤维,可列举出由聚吲哚、芳族聚酰胺、PBO(聚对苯撑苯并噁唑)、聚苯硫醚、聚酯、丙烯酸类、聚酰胺、聚烯烃、聚乙烯醇、聚芳酯等树脂材料形成的合成纤维;纤维素、纸浆、棉花、羊毛、丝绸之类的天然纤维;蛋白质、聚肽、藻酸等的再生纤维等。
本发明的组合物为了利用活性能量射线使其固化而优选使用聚合引发剂,特别优选使用光聚合引发剂。作为光聚合引发剂,使用公知的物质即可,可优选使用例如选自苯乙酮类、苯偶酰缩酮类、二苯甲酮类中的一种以上。作为前述苯乙酮类,可列举出二乙氧基苯乙酮、2-羟基-2-甲基-1-苯基丙烷-1-酮、1-(4-异丙基苯基)-2-羟基-2-甲基丙烷-1-酮、4-(2-羟基乙氧基)苯基-(2-羟基-2-丙基)酮等。作为前述苯偶酰缩酮类,可列举出例如1-羟基环己基-苯基酮、苯偶酰二甲基缩酮等。作为前述二苯甲酮类,可列举出例如二苯甲酮、邻苯甲酰基苯甲酸甲酯等。作为前述苯偶姻类等,可列举出例如苯偶姻、苯偶姻甲醚、苯偶姻异丙醚等。光聚合引发剂可以单独使用,也可以组合使用2种以上。前述光聚合引发剂的用量相对于前述组合物100重量%优选为1~15重量%,更优选为2~10重量%。
(热塑性树脂基材)
本发明的热塑性树脂基材是含有热塑性树脂的基材。作为热塑性树脂,具体而言,可列举出聚乙烯树脂、聚丙烯树脂、聚苯乙烯树脂、橡胶改性聚苯乙烯树脂、丙烯腈-丁二烯-苯乙烯(ABS)树脂、丙烯腈-苯乙烯(AS)树脂、聚甲基丙烯酸甲酯树脂、丙烯酸类树脂、聚氯乙烯树脂、聚偏二氯乙烯树脂、聚对苯二甲酸乙二醇酯树脂、乙烯乙烯醇树脂、乙酸纤维素树脂、离聚物树脂、聚丙烯腈树脂、聚酰胺树脂、聚缩醛树脂、聚对苯二甲酸丁二醇酯树脂、聚乳酸树脂、聚苯醚树脂、改性聚苯醚树脂、聚碳酸酯树脂、聚砜树脂、聚苯硫醚树脂、聚醚酰亚胺树脂、聚醚砜树脂、聚芳酯树脂、热塑性聚酰亚胺树脂、聚酰胺酰亚胺树脂、聚醚醚酮树脂、聚酮树脂、液晶聚酯树脂、氟树脂、间同立构聚苯乙烯树脂、环状聚烯烃树脂等。这些热塑性树脂可以使用1种或组合使用2种以上。
优选为ABS树脂、丙烯酸类树脂、聚甲基丙烯酸甲酯树脂和聚碳酸酯树脂,特别优选为聚碳酸酯树脂。
作为热塑性树脂基材,可以具有除了热塑性树脂之外的配混物,也可以在不损害本发明效果的范围内配混溶剂、各种树脂、反应性化合物、催化剂、聚合引发剂、有机填料、无机填料、有机溶剂、无机颜料、有机颜料、体质颜料、粘土矿物、蜡、表面活性剂、稳定剂、流动调节剂、偶联剂、染料、流平剂、流变控制剂、紫外线吸收剂、抗氧化剂、增塑剂等。
作为基材的形状,没有特别限定,可以具有平板、片状、棒状或三维结构,也可以为立体状。还可以为整面或一部分具有曲率的形状等与目的相符的任意形状。此外,基材的硬度、厚度等也没有限定。本发明的制造方法的特征在于,在制造层叠体后进行弯曲加工,因此,特别优选为平板或片状之类的形状。
(涂覆物)
通过将本发明的组合物涂覆于热塑性树脂基材,从而能够获得涂覆物。作为涂覆方法,没有特别限定,可列举出喷涂法、旋涂法、浸渍法、流涂法、辊涂法、板涂法、刮辊法、刮板法、帘涂法、狭缝涂覆法、丝网印刷法、喷墨法等。此时,也可以利用溶剂等来调整组合物的粘度。
<工序2>
本发明的工序2是获得具有固化物层的层叠体的工序,所述固化物层是对通过工序1得到的涂覆物照射活性能量射线并将前述组合物固化而得到的。
作为活性能量射线固化,是指通过对涂覆物照射活性能量射线而使其固化。活性能量射线可列举出紫外线、电子射线、α射线、β射线、γ射线等电离辐射。这些之中,从固化性和方便性的观点出发,特别优选为紫外线(UV)。
进行紫外线固化时使用的光可以使用例如低压汞灯、高压汞灯、金属卤化物灯、氙灯、氩气激光、氦镉激光等。通过使用它们,对涂覆物的涂布面照射约180~400nm的波长的紫外线,从而使涂膜固化而制作固化物层,能够获得层叠体。作为紫外线的照射量,可根据所使用的光聚合引发剂的种类和量进行适当选择。
(固化物层)
本发明的层叠体中的固化物层的厚度优选为0.5~40μm。这是因为:膜厚为0.5μm以上时,充分发挥出耐磨耗性,能够保护基材。如果膜厚为40μm以内,则耐弯曲性优异。进而,优选为0.5~30μm、更优选为0.5~15μm。进一步优选为1.0~7.0μm、特别优选为1.5~7.0μm。
<工序3>
本发明的工序3是将通过工序2得到的层叠体进行弯曲加工而得到成型体的工序。
本发明中,即使在对层叠体形成具有硬涂性的固化物层后加工性也优异,能够随后进行弯曲加工。
作为弯曲加工,除了将层叠体直接折弯的弯曲加工之外,还可列举出加压成型、吹塑成型、真空成型、压空成型、双复合成型等加工法。
进而,本发明的层叠体的特征在于,尤其是在加热下的弯曲性非常优异的基础上,热弯曲加工后的硬涂性也优异。
热弯曲加工中的加工温度优选为80℃以上。特别优选为150℃以上。加工温度的下限温度小于热塑性树脂基材的熔融温度。这是因为:若使加工温度上升至热塑性树脂基材的熔融温度以上,则层叠体自基材起开始熔融。
实施例
接着,通过实施例、比较例具体地说明本发明,以下的“份”和“%”在没有特别记载的情况下为重量基准。
合成例:UA-1
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值为165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入异佛尔酮二异氰酸酯111质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-1。由投入的原料算出的聚合性双键当量为131g/mol。
合成例:UA-2
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入降冰片烯二异氰酸酯103质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-2。由投入的原料算出的聚合性双键当量为128g/mol。
合成例:UA-3
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入4,4-亚甲基二环己基二异氰酸酯131质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-3。由投入的原料算出的聚合性双键当量为136g/mol。
合成例:UA-4
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入氢化二甲苯二异氰酸酯97质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-4。由投入的原料算出的聚合性双键当量为125g/mol。
合成例:UA-5
向具备温度计、搅拌装置的可分离烧瓶中填充200g的甲基异丁基酮、225.9g的IPDI,一边搅拌一边将内部温度升温至50℃。接着添加0.08g的二月桂酸二丁基锡,将内部温度保持至50℃,并耗费1小时滴加99.8g的三环癸烷二甲醇。滴加结束后,以50℃持续搅拌2小时,使氨基甲酸酯异氰酸酯预聚物的反应结束。需要说明的是,反应结束通过反应液中的异氰酸酯基浓度达到理论终点异氰酸酯基浓度以下来确认。本例中,确认到反应液中的异氰酸酯基浓度达到理论终点异氰酸酯基浓度(8.12重量%)以下后,转移至下一操作。接着,将内部温度升温至70℃,添加0.08g的二月桂酸二丁基锡,将反应温度保持至70℃,并耗费2小时滴加474.3g的PETIA(制品名“PETRA”(Sytec Co.,LTD.制;羟值为120mgKOH/g的季戊四醇三丙烯酸酯与季戊四醇四丙烯酸酯的混合物))。在滴加结束后以70℃持续搅拌1小时。确认异氰酸酯基浓度达到0.1重量%以下而使反应结束,得到在骨架中具有从三环癸烷二甲醇去除羟基的两个氢原子后的有机基团、且官能团数量为6的氨基甲酸酯(甲基)丙烯酸酯(UA-5)。由投入的原料算出的聚合性双键当量为205g/mol。
合成例UA-6
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值为165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入HDI-2聚化异氰酸酯168质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-6。由投入的原料算出的聚合性双键当量为148g/mol。
合成例:UA-7
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值为165mgKOH/g)525.95质量份、二月桂酸二丁基锡0.3质量份和对苯二酚0.3质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入HDI-3聚化异氰酸酯252质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-7。由投入的原料算出的聚合性双键当量为186g/mol。
合成例:UA-8
向具备搅拌机、温度计、滴液漏斗、冷凝管和空气导入口的反应容器中投入异佛尔酮二异氰酸酯111质量份、二丁基羟基甲苯1.55质量份、对甲氧基苯酚0.15质量份和二新癸酸二辛基锡0.15质量份,在空气通气下一边搅拌一边升温至60℃为止。接着,耗费1小时滴加聚己内酯改性单丙烯酸酯((Daicel Corporation制的“PlaccelFA10L”)836.77质量份。滴加结束后,将反应容器中升温至80℃为止,搅拌5小时,由此进行氨基甲酸酯化反应,得到含有脂环结构的内酯改性氨基甲酸酯丙烯酸酯(聚合性双键当量为1369g/mol)。
合成例:UA-9
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值165mgKOH/g)350.63质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入六亚甲基二异氰酸酯84质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯树脂UA-9。由投入的原料算出的聚合性双键当量为122g/mol。
合成例:UA-10
向四颈烧瓶中添加季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯的混合物(TOAGOSEI CO.,LTD.制的“ARONIX M-306”、羟值165mgKOH/g)525.95质量份、二月桂酸二丁基锡0.2质量份和对苯二酚0.2质量份,制成均匀溶液。加热至***内部温度达到50℃为止,接着,耗费约1小时分次投入HDI-缩二脲型异氰酸酯252质量份。以80℃使其反应3小时,利用红外吸收光谱确认异氰酸酯基消失后,使用乙酸丁酯将不挥发成分调整至80%,得到氨基甲酸酯(甲基)丙烯酸酯:UA-10。由投入的原料算出的聚合性双键当量为186g/mol。
<实施例1>
(组合物1的制备)
对于所合成的UA-5 100重量份,配混Tinuvin123(BASF株式会社制、光稳定剂)1重量份、Tinuvin479(BASF株式会社制、紫外线吸收剂)3重量份和Irgcure907(BASF株式会社、光引发剂)3重量份、BYK-UV-3505(BYK-Chemie)0.1重量份并进行搅拌,其后用丙二醇单甲醚进行稀释,得到树脂固体成分量为50重量份的组合物1。
(涂覆)
对于聚碳酸酯板(CARBOGLASS POLISH CLEAR、Asahi Glass Co.,Ltd.制、厚度2mm),使用棒涂机以干燥后的涂膜厚度达到约5μm的方式涂布组合物1,并利用80℃的干燥机干燥4~6分钟。
(固化)
紫外线照射使用GS-YUASA株式会社制的高压汞灯,在EIT株式会社制的UVPOWERPUCK的UV-A区域内,以峰照度达到200mW/cm2、每1道次的照射能量达到1000mJ/cm2的方式调整灯输出功率、灯高度和传送带速度,进行1道次(总计为1000mJ/cm2)的照射,得到层叠体1。
[弯曲加工试验:耐弯曲性]
将层叠体用恒温机以特定的温度加热10分钟后,以层叠体的硬涂层作为外侧,将硬涂层叠体卷绕至某一直径的圆筒的外周时,利用硬涂层产生裂纹时的圆筒的直径大小(0.6cm~9cm)来评价弯曲性。
[弯曲后的HC试验:耐磨耗性]
针对弯曲加工试验(圆筒直径为30cm)后的层叠体表面,在曲面状态下利用TABER磨耗试验并按照基于ASTM D1044的方法(耐磨轮:CS-10F、载荷:500g、转速:500次)进行摩擦,测定其与初始状态的雾度值之差、即雾度值变化ΔH(%)。差值越小,则表示耐磨耗性越高。
[弯曲后的HC试验:耐划伤性试验]
用钢丝棉(Nippon Steel Wool Co.,Ltd.制的“BONSTER#0000”)包裹单边为2厘米的正方状压头,对该压头施加1kg重的载荷,针对弯曲加工试验(圆筒直径为30cm)后的层叠体表面,在曲面状态下进行使压头在固化性组合物的固化涂膜表面往返11次的划伤试验。利用划伤试验后的涂膜划痕的条数进行评价。
◎:10条以下
○:20条以下
×:20条以上
<实施例2~27、比较例1~4>
在实施例1中,变更表1-1~表1-4记载的条件,除此之外,同样进行层叠体的制造和评价。
[表1]
[表2]
[表3]
[表4]
A-DCP:环癸烷二甲醇二丙烯酸酯(新中村化学工业株式会社)
DPCA-30:DPHA内酯改性化合物(日本化药株式会社)
Silica-1:PGM-ST(日产化学工业株式会社制)、未修饰二氧化硅(平均粒径为50nm)
Silica-2:MIBK-SD(日产化学工业株式会社制)、甲基丙烯酰基修饰二氧化硅(平均粒径为50nm)
Silica-3:R7200(AEROSIL株式会社制)、甲基丙烯酰基修饰二氧化硅(平均粒径为150nm)
产业上的可利用性
通过本发明,能够以与基材的两层结构的形式制造可进行二维弯曲加工的硬涂层叠体。其结果,能够在车棚、高速公路的隔音墙、树脂玻璃等室外用途中廉价地提供具有例如与由透明树脂板形成的平面部连续的弯曲部的构成构件。
Claims (10)
1.一种成型体的制造方法,其特征在于,具有如下工序:
工序1,将含有脂环式氨基甲酸酯(甲基)丙烯酸酯的组合物涂覆于热塑性树脂基材而得到涂覆物;
工序2,获得具有固化物层的层叠体,所述固化物层是对所得涂覆物照射活性能量射线并将所述组合物固化而得到的;以及
工序3,将所得层叠体进行弯曲加工而得到成型体,
所述脂环式氨基甲酸酯(甲基)丙烯酸酯分别具有:式(A)所示的具有脂环结构的结构、以及2个以上式(B)所示的具有(甲基)丙烯酰基的基团,进而,聚合性双键当量为100~1000g/mol,
式(A)中,X为下述式(1)所示的脂环结构之中的至少1个;Y1、Y2各自独立地为直接键合、碳原子数1~10的烃基、氨基甲酸酯键、醚键、酰胺键或羰基;n表示1~6的整数,
式(1)中,脂环结构分别任选具有或不具有取代基,
通式(B)中,R1为直接键合或2价的连接基团;Y为直接键合或碳原子;R2为直接键合、碳原子数1~3的烃基或羰基;R3为氢原子或甲基;m表示1~3的整数。
2.根据权利要求1所述的成型体的制造方法,其中,所述将所得层叠体进行弯曲加工而得到成型体的工序3中的加工温度为80℃以上且小于热塑性树脂基材的熔融温度。
3.根据权利要求1或2所述的成型体的制造方法,其中,所述脂环式氨基甲酸酯(甲基)丙烯酸酯为式(2)所示的化合物,
B1-R4-A-R5-B2
···(2)
式(2)中,A为所述式(A)所示的结构;B1、B2各自独立地为所述式(B)所示的结构;R4、R5各自独立地表示直接键合或碳原子数1~10的烃基。
4.根据权利要求1~3中任一项所述的成型体的制造方法,其中,组合物还包含具有聚合性双键的化合物。
5.根据权利要求4所述的成型体的制造方法,其中,具有聚合性双键的化合物是具有异氰脲酸酯环且聚合性双键当量为100~1000g/mol的含异氰脲酸酯环的(甲基)丙烯酸酯。
6.根据权利要求4或5中任一项所述的成型体的制造方法,其中,相对于组合物中的脂环式氨基甲酸酯(甲基)丙烯酸酯和具有聚合性双键的化合物的总计,所述脂环式氨基甲酸酯(甲基)丙烯酸酯的成分为10wt%~95wt%。
7.根据权利要求1~6中任一项所述的成型体的制造方法,其中,所述组合物还含有二氧化硅。
8.根据权利要求7所述的成型体的制造方法,其中,二氧化硅为反应性二氧化硅。
9.根据权利要求1~8中任一项所述的成型体的制造方法,其中,所述固化物层的厚度为1~40μm。
10.根据权利要求1~9中任一项所述的成型体的制造方法,其中,基材为聚碳酸酯。
Priority Applications (1)
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JP7023053B2 (ja) * | 2017-03-31 | 2022-02-21 | 株式会社松風 | ウレトジオン基を含有するカップリング性有機化合物および、それらを含む医科歯科用硬化性組成物 |
JP7404656B2 (ja) * | 2019-05-27 | 2023-12-26 | 大日本印刷株式会社 | 硬化性樹脂組成物、樹脂硬化物、積層フィルム、転写フィルム及び積層体 |
JP7454777B1 (ja) | 2023-08-23 | 2024-03-25 | artience株式会社 | 透明基材上にハードコート層を形成するための活性エネルギー線硬化性組成物、それを用いたハードコートフィルムおよびその積層体。 |
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JP2022069479A (ja) | 2022-05-11 |
CN114316332B (zh) | 2023-08-04 |
CN110402192B (zh) | 2021-12-24 |
JPWO2018168828A1 (ja) | 2020-05-14 |
US20210122849A1 (en) | 2021-04-29 |
WO2018168828A1 (ja) | 2018-09-20 |
ES2919073T3 (es) | 2022-07-21 |
EP3597394B1 (en) | 2022-06-01 |
JP7031659B2 (ja) | 2022-03-08 |
EP3597394A1 (en) | 2020-01-22 |
EP3597394A4 (en) | 2020-11-25 |
CN114316332A (zh) | 2022-04-12 |
JP7318754B2 (ja) | 2023-08-01 |
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