CN103044921B - 可光固化的有机基聚硅氧烷组合物 - Google Patents
可光固化的有机基聚硅氧烷组合物 Download PDFInfo
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- CN103044921B CN103044921B CN201210383083.8A CN201210383083A CN103044921B CN 103044921 B CN103044921 B CN 103044921B CN 201210383083 A CN201210383083 A CN 201210383083A CN 103044921 B CN103044921 B CN 103044921B
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- Prior art keywords
- methyl
- organopolysiloxane composition
- photo curable
- curable organopolysiloxane
- titanium
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 56
- -1 titanium alkoxide Chemical class 0.000 claims abstract description 73
- 239000010936 titanium Substances 0.000 claims abstract description 26
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 229910000077 silane Inorganic materials 0.000 claims description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
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- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
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- 238000000034 method Methods 0.000 claims description 5
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 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 claims description 3
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- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 2
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- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 2
- KMSYDDGPKBBSNA-UHFFFAOYSA-N 3-ethyl-1-phenylpentan-1-one Chemical compound CCC(CC)CC(=O)C1=CC=CC=C1 KMSYDDGPKBBSNA-UHFFFAOYSA-N 0.000 claims description 2
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
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- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 claims description 2
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 12
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- 125000004429 atom Chemical group 0.000 claims 3
- 239000010703 silicon Substances 0.000 claims 3
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims 2
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 claims 1
- KKVBXYFFCPVJIV-UHFFFAOYSA-N (4-benzyl-4-chlorocyclohexa-1,5-dien-1-yl)-phenylmethanone Chemical compound C1C=C(C(=O)C=2C=CC=CC=2)C=CC1(Cl)CC1=CC=CC=C1 KKVBXYFFCPVJIV-UHFFFAOYSA-N 0.000 claims 1
- FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 claims 1
- XBBFHDQVQABZPF-UHFFFAOYSA-N C(C)C(=O)CC.BrC1=CC=CC=C1 Chemical compound C(C)C(=O)CC.BrC1=CC=CC=C1 XBBFHDQVQABZPF-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 7
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- 125000005594 diketone group Chemical group 0.000 abstract 1
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- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002454 metastable transfer emission spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 239000012508 resin bead Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- XXZNHVPIQYYRCG-UHFFFAOYSA-N trihydroxy(propoxy)silane Chemical compound CCCO[Si](O)(O)O XXZNHVPIQYYRCG-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
公开了一种可光固化的有机基聚硅氧烷组合物,它包括(A)100重量份在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;和(B)0.1‑30重量份由(甲基)丙烯酸‑三烷醇‑钛和β‑二酮组成的络合物。它可用作密封剂,粘合剂,涂布材料。它尤其适合于微型部件和精确模塑,因为它具有良好的可固化性和非常小的固化收缩率。
Description
技术领域
本发明涉及光固化性优良且能在室温下固化的可光固化的有机基聚硅氧烷组合物,它可用作密封剂、粘合剂、涂料材料。更特别地,本发明涉及不需要任何特殊光官能的有机基聚硅氧烷的可光固化的有机基聚硅氧烷组合物。
背景技术
众所周知的事实是,通过在有机过氧化物存在下加热或者通过氢化硅烷化反应,有机基聚硅氧烷转化成耐热性、耐寒性、耐候性和电性能优良的硅橡胶。还众所周知的是,在室温下,通过缩合反应固化的结果是可获得该硅橡胶。
另一方面,在光引发剂存在下通过用光辐照下固化的有机基聚硅氧烷是已知的。
UV(紫外)-可固化的有机基聚硅氧烷组合物公开于JP-B S52-40334和JP-A S60-104158(专利文献1和2)中。该组合物包括含乙烯基的聚硅氧烷和含巯基的聚硅氧烷,并通过光-自由基加成反应,形成固化产物。另一实例公开于JP-B S53-36515,JP-A S60-215009和JP2647285(专利文献3-5)中。它是可光固化的有机基聚硅氧烷组合物,所述组合物包括含丙烯酸基的聚硅氧烷和敏化剂,并且通过用光辐照,形成固化产物。
遗憾的是,以上提及的含有含乙烯基的聚硅氧烷和含巯基的聚硅氧烷的组合物涉及因巯基导致的臭味和在金属上腐蚀的问题。因此,它们的应用受到限制。
以上提及的含有含丙烯酸基的聚硅氧烷和敏化剂的组合物也有要求高分子量线性聚硅氧烷作为含丙烯酸基的聚硅氧烷以供生产橡胶状弹性产品的缺点。线性聚硅氧烷的分子量越高,丙烯酸端基量越少。这导致差的可固化性。另一缺点是,与空气接触的组合物表面非常少地固化,这是因为受到空气的抑制作用。因此,除了含有具有相当大含量丙烯酸基的聚硅氧烷且得到树脂状固化产物的那种组合物以外,这类组合物不具有实际用途。在实践中,它们无一得到橡胶状弹性产品。
而且,含巯基的聚硅氧烷和含丙烯酸基的聚硅氧烷需要特殊的合成路线用于其生产。所得产品通常被视为遭受法律调控和不利的成本控制(costwise)的新化学物质。
与缩合类,可热固化类,和使用铂催化剂的加成反应类的组合物相比,可光固化的有机基聚硅氧烷组合物的可操作性是有利的,因为通过用UV辐照,它能在短时间内固化。然而,按照这一方式获得的所得产品(硅橡胶弹性体)的拉伸强度和储存稳定性差,这限制了其应用。
过去,另一技术涉及使用由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物用于微构图(micropattern)光敏溶胶-凝胶体系的有机-无机混杂薄膜的用途,所述光敏溶胶-凝胶体系由双层甲板(double-decker)类的多官能的倍半硅氧烷形成,正如ChemistryLetters Vol.35,No.10(2006),pp.1130-1131(非专利文献1)中所公开的。
公开了该络合物充当粘合促进剂,当掺入到高固体的丙烯酸树脂组合物内时,所述粘合促进剂改进对涂布膜的粘合性(参见JP-A2001-240620(专利文献6))。然而,这一公开内容根本没有提及它作为固化催化剂的用途。
引证文献列举
专利文献1:JP-B S52-40334
专利文献2:JP-A S60-104158
专利文献3:JP-B S53-36515
专利文献4:JP-A S60-215009
专利文献5:JP 2647285
专利文献6:JP-A 2001-240620
非专利文献1:Chemistry Letters Vol.35,No.10(2006),pp.1130-1131
发明内容
本发明的目的是提供可光固化的有机基聚硅氧烷组合物,它不具有常规的可光固化的有机基聚硅氧烷组合物的以上提及的缺点,且在不需要任何特殊的光官能的有机基聚硅氧烷的情况下,能通过UV辐照光固化,从而产生橡胶状特征优良的固化产物。
本发明发明人深入研究以解决上述问题的结果是,发现通过掺入由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物到可光固化的有机基聚硅氧烷组合物内,通过UV辐照,则催化活性增加,从而导致可光固化的有机基聚硅氧烷组合物优良的可固化性。这一发现导致了本发明。
本发明涵盖下述可光固化的有机基聚硅氧烷组合物。
[1]一种可光固化的有机基聚硅氧烷组合物,它包括:
(A)100重量份在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;和
(B)0.1-30重量份由(甲基)丙烯酸-三烷醇-钛(titanium-(meth)acrylate-trialkoxide)和β-二酮组成的络合物。
[2][1]中的可光固化的有机基聚硅氧烷组合物,其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物是用下式(3)表示的络合物:
其中R1是氢原子或甲基;R2和R3各自是具有1-12个碳原子的未取代或取代的单价烃基;和R4是具有1-12个碳原子的未取代或取代的单价烃基,或具有1-8个碳原子的烷氧基。
[3][2]中的可光固化的有机基聚硅氧烷组合物,其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物是由(甲基)丙烯酸-三异丙醇-钛和苯甲酰丙酮组成的络合物。
[4][1]-[3]任何一项的可光固化的有机基聚硅氧烷组合物,其中组分(A)是其分子链两端被羟基和/或可水解基团封端的二有机基聚硅氧烷。
[5][4]中的可光固化的有机基聚硅氧烷组合物,其中组分(A)是具有下式(1)或(2)的二有机基聚硅氧烷:
其中R是具有1-12个碳原子的未取代或取代的单价烃基;X是氧原子或具有1-8个碳原子的二价烃基;Y是可水解基团;b为2或3;和m为满足二有机基聚硅氧烷在25℃下的粘度为100-1,000,000mPa·s的数值。
[6][1]-[5]任何一项的可光固化的有机基聚硅氧烷组合物,它进一步包括在一个分子内具有至少两个可水解基团的硅烷和/或其部分水解物的缩合物作为组分(C)。
[7][1]-[6]任何一项的可光固化的有机基聚硅氧烷组合物,它进一步包括光引发剂作为组分(D)。
本发明的有益效果
本发明的可光固化的有机基聚硅氧烷组合物可在微型部件和精确模塑的应用领域中用作密封剂,粘合剂和涂料材料,因为它具有良好的可固化性和非常小的固化收缩率。
具体实施方式
以下更加详细地描述本发明。
本发明的可光固化的有机基聚硅氧烷组合物含有:
用量为100重量份的组分(A),它是在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;
用量为0.1-30重量份的组分(B),它是由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物;和任选地
组分(C),它是在一个分子内具有至少两个可水解基团的硅烷和/或其部分水解物的缩合物;和/或
组分(D),它是光引发剂。
组分(A)
组分(A)是在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷。这一组分是本发明的可光固化的有机基聚硅氧烷组合物的基础聚合物。在其分子内,它具有连接到硅原子上的至少两个羟基或可水解基团。它可以是直链类,支链类,或树脂类。优选直链类。二有机基聚硅氧烷的典型实例用下式(1)或(2)表示,其分子在每一末端被羟基或可水解基团封端:
其中R是具有1-12个碳原子的未取代或取代的单价烃基;X是氧原子或具有1-8个碳原子的二价烃基;Y是可水解基团;b为2或3;和m为满足二有机基聚硅氧烷在25℃下的粘度为100-1,000,000mPa·s的数值。
在上式中,用R表示的未取代或取代的单价烃基例举为烷基(例如,甲基,乙基,丙基,丁基,戊基,己基,庚基,辛基,壬基,癸基和十八烷基),环烷基(例如,环戊基,和环己基),烯基(例如乙烯基,烯丙基,丁烯基,戊烯基,和己烯基),芳基(例如,苯基,甲苯基,二甲苯基,α-萘基和β-萘基),芳烷基(例如,苄基,2-苯乙基,和3-苯丙基),和其氢原子被卤素原子(例如,F,Cl和Br)或氰基部分或完全取代的任何一个前述基团,例如3-氯丙基,3,3,3-三氟丙基,和2-氰乙基。在这些基团当中,优选甲基,乙基,和苯基,其中甲基是最希望的。
在上式中,X是氧原子或C1-8二价烃基,例如亚烷基。后者用-(CH2)p-表示,其中p为1-8。尤其优选氧或-CH2CH2-。
在上式中,Y是在二有机基聚硅氧烷的分子链的两个末端处的可水解基团。例举为烷氧基(例如甲氧基,乙氧基和丙氧基),烷氧基烷氧基(例如,甲氧基乙氧基,乙氧基乙氧基,和甲氧基丙氧基),酰氧基(例如,乙酰氧基,辛酰氧基和苯甲酰氧基),烯基氧基(例如乙烯基氧基,异丙烯基氧基和1-乙基-2-甲基乙烯基氧基),酮肟基(例如,二甲基酮肟基,甲基乙基酮肟基,和二乙基酮肟基),氨基(例如,二甲基氨基,二乙基氨基,丁基氨基,和环己基氨基),氨氧基(例如,二甲基氨氧基,和二乙基氨氧基),和酰胺基(例如,N-甲基乙酰胺基,N-乙基乙酰胺基和N-甲基苯甲酰胺基)。这些基团中尤其优选烷氧基,且甲氧基与乙氧基是更希望的,和甲氧基尤其是希望的。
作为组分(A)的二有机基聚硅氧烷应当是粘度(25℃下)为100-1,000,000mPa·s,优选300-500,000mPa·s,更优选500-100,000mPa·s,和尤其1,000-80,000mPa·s的那些。在采用极低粘度的情况下,所得组合物得不到物理性能和机械强度优良的固化产物。在采用极高粘度的情况下,所得组合物的可操作性差。顺便说一下,通过使用旋转粘度计测量粘度。
作为组分(A)的二有机基聚硅氧烷如下所例举:
其中m,R和Y如上所定义,和b`为0或1。
作为组分(A)的二有机基聚硅氧烷可单独或与其结构和分子量不同的至少两个同系物结合使用。
组分(B)
组分(B)是由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物,它是使本发明组合物产生可固化性的重要组分且用下式(3)表示:
其中R1是氢原子或甲基;R2和R3各自是具有1-12个碳原子的未取代或取代的单价烃基;和R4是具有1-12个碳原子的未取代或取代的单价烃基,或具有1-8个碳原子的烷氧基。
R2,R3和R4是与以上定义的R相同的取代基。R2的优选实例包括甲基,乙基,正丙基,异丙基,正丁基,叔丁基,和2-乙基己基。R3的优选实例包括甲基,乙基,正丙基,异丙基,正丁基,叔丁基,2-乙基己基和苄基。R4的优选实例包括甲基,乙基,正丙基,异丙基,正丁基,叔丁基,2-乙基己基,甲氧基和乙氧基。
可通过下述步骤合成组分(B),所述步骤以仅仅一个实例给出。
通过在室温下混合在THF(四氢呋喃)内的甲基丙烯酸-三异丙醇-钛与苯甲酰丙酮的THF溶液,实现以上所述的合成。这一方法快速地得到络合物作为所需产物。
以下示出了络合物的典型实例,其中iPr代表异丙基和Ph代表苯基。
对于100重量份组分(A)来说,组分(B)的用量应当是0.1-30重量份,优选0.5-20重量份,更优选1-15重量份。在组分(B)的用量小于0.1重量份或者大于30重量份的情况下,所得组合物的可固化性差且不能得到具有良好回弹性的固化产物。充足用量范围为0.1-30重量份。
本发明的组合物应当任选地掺入在一个分子内具有至少两个可水解基团的硅烷和/或其部分水解物的缩合物作为组分(C)。组分(C)有效地改进本发明组合物的可固化性。在一个分子内它应当具有键合到硅原子上的至少两个可水解基团。这种有机基硅化合物的典型实例是用下式表示的硅烷或其部分水解物的缩合物:
RaSiZ4-a
其中R如上所定义,Z独立地表示可水解基团,和a是0-2的整数。
可水解基团(Z)可以是与可水解基团(Y)相同的基团。在以上提及的那些可水解基团当中,优选烷氧基,酮肟基,和异丙烯基氧基,尤其酮肟基。
组分(C)是硅烷或其部分水解物的缩合物,在没有任何其他限制的情况下,如上所述它应当在一个分子内基本上具有至少两个可水解基团。它应当优选具有至少三个可水解基团。在组分(C)内的硅原子可具有连接到其上的除了可水解基团以外的任何其他基团。而且,它可具有硅烷或硅氧烷的分子结构。硅氧烷结构可以是直链,支链或环状的。
以上提及的基团(R)不包括可水解基团,它可以是以下例举的具有1-12个碳原子,优选1-8个碳原子的未取代或取代的单价烃基:烷基(例如,甲基,乙基,丙基,丁基,戊基,和己基),环烷基(例如,环戊基,和环己基),芳基(例如,苯基,和甲苯基);芳烷基(例如,苄基,和2-苯乙基);烯基(例如乙烯基,烯丙基,丁烯基,戊烯基,和己烯基);和卤代烷基(例如,3,3,3-三氟丙基,和3-氯丙基)。在这些基团当中,优选甲基,乙基,丙基,苯基和乙烯基。
根据本发明,组分(C)是以下例举的有机基硅化合物:硅酸乙酯,硅酸丙酯,甲基三甲氧基硅烷,甲基三乙氧基硅烷,乙烯基三甲氧基硅烷,乙烯基三乙氧基硅烷,甲基三(甲氧基乙氧基)硅烷,乙烯基三(甲氧基乙氧基)硅烷,甲基三丙烯基氧基硅烷,甲基三乙酰氧基硅烷,乙烯基三乙酰氧基硅烷,甲基三(甲基乙基酮肟基)硅烷,乙烯基三(甲基乙基酮肟基)硅烷,苯基三(甲基乙基酮肟基)硅烷,丙基三(甲基乙基酮肟基)硅烷,四(甲基乙基酮肟基)硅烷,3,3,3-三氟丙基三(甲基乙基酮肟基)硅烷,3-氯丙基三(甲基乙基酮肟基)硅烷,甲基三(二甲基酮肟基)硅烷,甲基三(二乙基酮肟基)硅烷,甲基三(甲基异丙基酮肟基)硅烷,三(环己基肟基)硅烷,及其部分水解物的缩合物。在这些实例当中优选甲基三(甲基乙基酮肟基)硅烷,乙烯基三(甲基乙基酮肟基)硅烷,苯基三(甲基乙基酮肟基)硅烷,丙基三(甲基乙基酮肟基)硅烷,四(甲基乙基酮肟基)硅烷,3,3,3-三氟丙基三(甲基乙基酮肟基)硅烷,甲基三(二甲基酮肟基)硅烷,甲基三(二乙基酮肟基)硅烷,甲基三(甲基异丙基酮肟基)硅烷,和三(环己基肟基)硅烷。
它们可单独或彼此结合使用。
对于100重量份组分(A)来说,组分(C)的用量应当是0.1-30重量份,优选0.5-20重量份,更优选1-15重量份。对于组分(C)来说,小于0.1重量份的用量太小,难以产生其效果。在组分(C)的用量大于30重量份的情况下,所得组合物具有过大的固化收缩率,且将得到回弹性差的固化产物。
本发明的组合物应当优选掺入工业上众所周知的光引发剂作为组分(D)。
光引发剂的实例是苯乙酮,苯丙酮,二苯甲酮,呫吨酮(xanthone),荧光母素(fluoran),苯甲醛,蒽醌,三苯胺,咔唑,3-甲基苯乙酮,4-甲基苯乙酮,3-戊基苯乙酮,4-甲氧基苯乙酮,2,2-二乙氧基苯乙酮,3-溴苯乙酮,4-烯丙基苯乙酮,对二乙酰基苯,3-甲氧基二苯甲酮,4-甲基二苯甲酮,4-氯二苯甲酮,4,4-二甲氧基二苯甲酮,4-氯-4-苄基二苯甲酮,3-氯呫吨酮,3,9-二氯呫吨酮,3-氯-8-壬基呫吨酮,苯偶姻,苯偶姻甲醚,苯偶姻丁醚,双(4-二甲基氨基苯酚)酮,苄基甲氧基缩酮和2-氯噻吨酮。对于100重量份组分(A)来说,组分(D)的用量应当优选为0.01-5重量份。
本发明的组合物可另外掺入为不损害本发明效果的用量的任何已知的添加剂和填料。
固化促进剂
本发明的组合物可掺入一种或多种促进剂以供缩合反应。
它们的实例包括下述:锡催化剂(例如,二辛酸锡,二叔碳酸(diversatate)二甲锡,二丁基二甲氧基锡,二乙酸二丁锡,二辛酸二丁锡,二月桂酸二丁锡,二苄基马来酸二丁锡,二月桂酸二辛锡和锡的螯合物),强碱性化合物(例如,胍和DBU(1,8-二氮杂双环[5.4.0]-7-十一碳烯))和含有它们的那些化合物,其中包括烷氧基硅烷,钛酸酯(例如,四异丙氧基钛,四正丁氧基钛,四(2-乙基己氧基)钛,二丙氧基二(乙酰基丙酮)钛和异丙氧基亚辛基二醇钛)和钛的螯合物化合物。对于100重量份组分(A)来说,促进剂的用量应当优选为0.001-20重量份,尤其0.01-10重量份。
粘合促进剂
另一任选的添加剂是以下例举的胺类的任何硅烷偶联剂:
γ-氨丙基三甲氧基硅烷,γ-氨丙基三乙氧基硅烷,γ-氨丙基甲基二甲氧基硅烷,γ-氨丙基甲基二乙氧基硅烷,亚乙基二氨丙基三甲氧基硅烷,亚乙基二氨丙基三乙氧基硅烷,亚乙基二氨丙基甲基二甲氧基硅烷,亚乙基二氨丙基甲基二乙氧基硅烷和α-氨丙基三甲氧基硅烷。
尽管具有伯氨基的有机胺可用作有机化合物,但由于它具有腐蚀性和臭味,因此希望使用含有伯氨基的聚合物或低聚物形式的有机胺或含有伯氨基作为官能团的硅烷偶联剂(或其部分水解物)。对于100重量份组分(A)来说,粘合促进剂的用量优选应当为0.1-20重量份。
其他组分
本发明的组合物可掺入以上提及的以外的其他组分(例如已知用于室温可固化的有机基聚硅氧烷组合物中的添加剂)。它们典型地包括增强填料(例如热解法二氧化硅,湿法二氧化硅,沉淀二氧化硅,和碳酸钙),金属氧化物(例如氧化铝,和氧化锌),金属氢氧化物,炭黑,玻璃珠,玻璃球,树脂珠,和树脂球,它们可以进行或者可以没有进行常规的表面处理。额外的实例包括聚醚(作为触变改进剂),异链烷烃(作为增塑剂),和由三甲基硅氧烷单元和SiO2单元组成的网络聚硅氧烷(作为交联密度改进剂)。进一步的额外实例包括着色剂(如颜料、染料和荧光增白剂),生理活性物质(例如,杀细菌剂,抗细菌剂,蟑螂排斥剂,和海洋生物排斥剂),和表面改进剂(例如,与硅氧烷不相容的有机液体)。
也可稀释该组合物以供改进可涂布性。用于这一目的的稀释剂包括有机溶剂(例如,甲苯,二甲苯,溶剂汽油,环己烷,甲基环己烷,和低沸点异链烷烃)和挥发性硅烷与硅氧烷。
固化方法
可通过紫外辐射线固化本发明的可光固化的有机基聚硅氧烷组合物。UV光优选应当是波长范围为10-400nm,尤其200-380nm的近紫外光,但没有具体地限制。可使用众所周知的高压汞金属卤化物灯。对于高压汞金属卤化物灯来说,辐照量应当优选为100-10,000mJ/cm2,但没有具体地限制。
可在室温下,在数秒到一周内实现固化。
组合物的应用
本发明的可光固化的有机基聚硅氧烷组合物可用作密封剂、粘合剂、涂布材料。它能牢固地粘结到基底上。
实施例
以下是阐述合成例、实施例和对比例的本发明的详细说明,且绝不打算限制本发明的范围。顺便说一下,在下述实施例中给出的粘度采用旋转粘度计在25℃下测量。
合成例
制备含有3.02g甲基丙烯酸-三异丙醇-钛在2gTHF(四氢呋喃)内的溶液。它为浅黄色透明液体。制备含有1.63g苯甲酰丙酮在2.5gTHF内的另一溶液。在室温下一起混合这两种溶液,它们快速地变为含有络合物的橙色透明液体,所述络合物为用下式表示的化合物(A)。
化合物(A)
实施例1
通过均匀混合100重量份粘度为700mPa·s的二甲基聚硅氧烷(在两个端基处用羟基封端)和4重量份在THF内的溶液形式的化合物(A),制备组合物。
实施例2
通过均匀混合实施例1中获得的组合物与3重量份甲基三甲氧基硅烷,制备组合物。
实施例3
通过均匀混合实施例1中获得的组合物与0.3重量份2,2-二乙氧基苯乙酮,制备组合物。
对比例1
以与实施例1相同的方式制备组合物,所不同的是不添加化合物(A)。
对比例2
以与实施例1相同的方式制备组合物,所不同的是化合物(A)被1.6重量份苯甲酰丙酮替代。
对比例3
以与实施例1相同的方式制备组合物,所不同的是化合物(A)被3.02重量份甲基丙烯酸-三异丙醇-钛替代。
评价方法
将每一按以上所述制备的组合物的样品置于圆柱形玻璃器皿(测量内径为约30mm和深度为约20mm)内。然后在下述条件下,通过用紫外光辐照固化。
UV源:1个高压汞灯(80W/cm)
距离:10cm
转移速度;1m/min(3次),1,500mJ/cm2
观察固化状态,并以固化部分的体积(百分数)形式表示结果,如表1所示。
表1
Claims (15)
1.一种可光固化的有机基聚硅氧烷组合物,它包括:
(A)100重量份在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;和
(B)0.1-30重量份由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物,
其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物用下式(3)表示:
其中R1是氢原子或甲基;各R2是具有1-12个碳原子的未取代或取代的单价烃基;R3是苯基;和R4是具有1-12个碳原子的未取代或取代的单价烃基,或具有1-8个碳原子的烷氧基。
2.权利要求1的可光固化的有机基聚硅氧烷组合物,其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物是由(甲基)丙烯酸-三异丙醇-钛和苯甲酰丙酮组成的络合物。
3.权利要求1的可光固化的有机基聚硅氧烷组合物,其中组分(A)是其分子链两端被羟基和/或可水解基团封端的二有机基聚硅氧烷。
4.权利要求3的可光固化的有机基聚硅氧烷组合物,其中组分(A)是具有下式(1)或(2)的二有机基聚硅氧烷:
其中R是具有1-12个碳原子的未取代或取代的单价烃基;X是氧原子或具有1-8个碳原子的二价烃基;Y是可水解基团;b为2或3;和m为满足二有机基聚硅氧烷在25℃下的粘度为100-1,000,000mPa·s的数值。
5.一种可光固化的有机基聚硅氧烷组合物,它包括:
(A)100重量份在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;
(B)0.1-30重量份由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物,其中由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物用下式(3)表示:
其中R1是氢原子或甲基;各R2是具有1-12个碳原子的未取代或取代的单价烃基;R3是苯基;和R4是具有1-12个碳原子的未取代或取代的单价烃基,或具有1-8个碳原子的烷氧基,和
(C)0.1-30重量份在一个分子内具有至少两个可水解基团的硅烷和/或其部分水解物的缩合物。
6.一种可光固化的有机基聚硅氧烷组合物,它包括:
(A)100重量份在一个分子内具有带连接到其上的羟基和/或可水解基团的至少两个硅原子的二有机基聚硅氧烷;
(B)0.1-30重量份由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物,其中由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物用下式(3)表示:
其中R1是氢原子或甲基;各R2是具有1-12个碳原子的未取代或取代的单价烃基;R3是苯基;和R4是具有1-12个碳原子的未取代或取代的单价烃基,或具有1-8个碳原子的烷氧基,和
(D)0.01-5重量份光引发剂。
7.权利要求6的可光固化的有机基聚硅氧烷组合物,其中所述光引发剂是选自苯乙酮,苯丙酮,二苯甲酮,呫吨酮(xanthone),荧光母素(fluoran),苯甲醛,蒽醌,三苯胺,咔唑,3-甲基苯乙酮,4-甲基苯乙酮,3-戊基苯乙酮,4-甲氧基苯乙酮,2,2-二乙氧基苯乙酮,3-溴苯乙酮,4-烯丙基苯乙酮,对二乙酰基苯,3-甲氧基二苯甲酮,4-甲基二苯甲酮,4-氯二苯甲酮,4,4-二甲氧基二苯甲酮,4-氯-4-苄基二苯甲酮,3-氯呫吨酮,3,9-二氯呫吨酮,3-氯-8-壬基呫吨酮,苯偶姻,苯偶姻甲醚,苯偶姻丁醚,双(4-二甲基氨基苯酚)酮,苄基甲氧基缩酮和2-氯噻吨酮中的至少一种。
8.权利要求5的可光固化的有机基聚硅氧烷组合物,其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物是由(甲基)丙烯酸-三异丙醇-钛和苯甲酰丙酮组成的络合物。
9.权利要求5的可光固化的有机基聚硅氧烷组合物,其中组分(A)是其分子链两端被羟基和/或可水解基团封端的二有机基聚硅氧烷。
10.权利要求9的可光固化的有机基聚硅氧烷组合物,其中组分(A)是具有下式(1)或(2)的二有机基聚硅氧烷:
其中R是具有1-12个碳原子的未取代或取代的单价烃基;X是氧原子或具有1-8个碳原子的二价烃基;Y是可水解基团;b为2或3;和m为满足二有机基聚硅氧烷在25℃下的粘度为100-1,000,000mPa·s的数值。
11.权利要求6的可光固化的有机基聚硅氧烷组合物,其中组分(B)的由(甲基)丙烯酸-三烷醇-钛和β-二酮组成的络合物是由(甲基)丙烯酸-三异丙醇-钛和苯甲酰丙酮组成的络合物。
12.权利要求6的可光固化的有机基聚硅氧烷组合物,其中组分(A)是其分子链两端被羟基和/或可水解基团封端的二有机基聚硅氧烷。
13.权利要求12的可光固化的有机基聚硅氧烷组合物,其中组分(A)是具有下式(1)或(2)的二有机基聚硅氧烷:
其中R是具有1-12个碳原子的未取代或取代的单价烃基;X是氧原子或具有1-8个碳原子的二价烃基;Y是可水解基团;b为2或3;和m为满足二有机基聚硅氧烷在25℃下的粘度为100-1,000,000mPa·s的数值。
14.固化产品的制备方法,包括通过紫外光辐照固化权利要求1、5或6的可光固化的有机基聚硅氧烷组合物。
15.权利要求14的方法,其中UV光是波长范围为10-400nm和辐照量为100-10,000mJ/cm2的近紫外光。
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TW201331297A (zh) | 2013-08-01 |
JP2013082815A (ja) | 2013-05-09 |
KR101856788B1 (ko) | 2018-05-10 |
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