CN101291941B - 新的有机硅烷化合物 - Google Patents
新的有机硅烷化合物 Download PDFInfo
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- CN101291941B CN101291941B CN200680039148XA CN200680039148A CN101291941B CN 101291941 B CN101291941 B CN 101291941B CN 200680039148X A CN200680039148X A CN 200680039148XA CN 200680039148 A CN200680039148 A CN 200680039148A CN 101291941 B CN101291941 B CN 101291941B
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- -1 silane compound Chemical class 0.000 title claims abstract description 51
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 238000006140 methanolysis reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005052 trichlorosilane Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 abstract description 15
- 229920005989 resin Polymers 0.000 abstract description 15
- 239000000758 substrate Substances 0.000 abstract description 10
- 239000011521 glass Substances 0.000 abstract description 9
- 239000011159 matrix material Substances 0.000 abstract description 9
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract 1
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- 239000011247 coating layer Substances 0.000 abstract 1
- 239000011256 inorganic filler Substances 0.000 abstract 1
- 229910003475 inorganic filler Inorganic materials 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
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- 239000000203 mixture Substances 0.000 description 15
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006884 silylation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- LJDWTVPLPAYESR-UHFFFAOYSA-N C(C=C)(=O)OC.OC(CO)(C)O Chemical compound C(C=C)(=O)OC.OC(CO)(C)O LJDWTVPLPAYESR-UHFFFAOYSA-N 0.000 description 1
- UNFQKSYEVRWWCC-UHFFFAOYSA-N C(C=C)(=O)OC.OC(CO)O Chemical compound C(C=C)(=O)OC.OC(CO)O UNFQKSYEVRWWCC-UHFFFAOYSA-N 0.000 description 1
- WQUYGVLLSSYSRD-UHFFFAOYSA-N C(C=C)(=O)OCC(C)O.CC=CC(=O)O Chemical compound C(C=C)(=O)OCC(C)O.CC=CC(=O)O WQUYGVLLSSYSRD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- PDMHGNCRGQVFSB-UHFFFAOYSA-N acetonitrile;platinum(2+) Chemical compound [Pt+2].CC#N PDMHGNCRGQVFSB-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PWYYERNADDIMJR-UHFFFAOYSA-N pentyl but-2-enoate Chemical compound CCCCCOC(=O)C=CC PWYYERNADDIMJR-UHFFFAOYSA-N 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- XAKYZBMFCZISAU-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XAKYZBMFCZISAU-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5475—Silicon-containing compounds containing nitrogen containing at least one C≡N bond
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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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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Abstract
本发明涉及一种新的有机硅烷化合物，并且更具体地，涉及一种在各种应用中有益于改进有机树脂对无机填料的亲合性或改进包含基体树脂的涂层对基板的粘合性的新的有机硅烷化合物。其特别地有益于改进用于液晶显示器的偏振片粘合剂对玻璃基板的粘合性，即使在热湿条件下，该粘合性随时间的变化也很小。
Description
技术领域
本发明涉及一种新的有机硅烷化合物，并且更具体地，涉及一种在各种应用中有益于改进有机树脂对无机填料的亲合性或改进包含基体树脂的涂层对基板的粘合性，特别地有益于改进用于液晶显示器的偏振片的粘合剂对玻璃基板的粘合性(即使在热湿条件下，该粘合性随时间的变化也很小)的新的有机硅烷化合物。
背景技术
日本专利公开号3022993公开了一种包含含有环氧基的硅烷化合物的粘合剂组合物和日本专利公开号平7-331204公开了一种包含含有烃的硅烷化合物的粘合剂组合物。
但是，这些粘合剂组合物的不利之处在于，它们不能在使用基板或偏振片的实际情况下提供要求的足够的粘合强度，在热湿条件下所述粘合强度过度增长，或剥离后粘合剂可能保留在基板上。
发明内容
技术问题
本发明的一个目的是提供一种在各种应用中，用于改进有机树脂对无机填料的亲合性或改进包含基体树脂的涂层对基板的粘合性的目的的新的有机硅烷化合物。
本发明的另一个目的是提供一种新的有机硅烷化合物，当其包含在用于液晶显示器的偏振片粘合剂中时，该有机硅烷化合物改进对玻璃基板的粘合性，即使在热湿条件下，该粘合性随时间的变化也很小。
技术方案
为了达到上述目的，本发明提供了一种由下列化学式(1)表示的有机硅烷化合物：
化学式1
其中，R1、R2和R3各自独立地为氢或C1～C3的烷基；X为-NR4-(其中R4是氢或C1～C3的烷基)、氧或硫；n是从3到10的整数；并且j是从1到3的整数。
在下文中给出了本发明的详细描述。
本发明的特征在于由化学式(1)表示的新的有机硅烷化合物。
可通过一步法或两步法制备由化学式(1)表示的有机硅烷化合物。
在制备所述有机硅烷化合物的一步法中，1-链烯基氰基乙酸酯和三烷氧基硅烷可在氯铂酸催化剂，Karstedt催化剂或氯铂酸与对称-二乙烯基四甲基二硅氧烷的配合物、二氯二(三苯基膦)铂(II)、顺-二氯双乙腈铂(II)或二羰基二氯铂(II)存在的条件下反应。优选地，催化剂选自氯铂酸或铂-乙烯基硅氧烷配合物中。可选择地，可通过氰基乙酰氯与N-烷基氨基烷基三醇盐(N-alkylaminoalkyl trialkoxide)在叔胺存在的条件下的反应制备有机硅烷化合物。
用于制备有机硅烷化合物的两步法如下：首先，1-链烯基氰基乙酸酯和三氯硅烷在氯铂酸催化剂或铂-乙烯基硅氧烷催化剂存在的条件下反应。随后，采用甲醇的反应产物的甲醇分解制备出该新的有机硅烷化合物。
上述反应可在例如氯仿、二氯甲烷、二氯乙烷等的卤代烷溶剂；例如四氢呋喃、二噁英等的环醚溶剂；或例如苯、甲苯、二甲苯等的芳族有机溶剂中进行。
优选地，反应进行的温度范围从10到200℃，并且更优选从50到150℃。而且，可进行用于纯化的真空蒸馏。
最优选地，由化学式(1)表示的合成的有机硅烷化合物的取代基R1是氢。
由化学式(1)表示的本发明的硅烷化合物的具体例子包括由下列化学式(2)表示的氰基乙酰氧基丙基三甲氧基硅烷和由下列化学式(3)表示的N-甲基-N-(3-三甲氧基甲硅烷基丙基)氰基乙酰胺。
化学式2
化学式3
由本发明的化学式(1)表示的有机硅烷化合物适合用于丙烯酸树脂组合物、热固性树脂组合物、热塑性树脂组合物等。
由化学式(1)表示的本发明的新的有机硅烷化合物能够有效地用于基体树脂。为了确定作为粘附促进添加剂的性能，采用本发明的有机硅烷化合物制备了丙烯酸基体树脂并且测试了其对玻璃的粘合性。
丙烯酸基体树脂能够从含有C1～C12的烷基的(甲基)丙烯酸酯单体和含有羟基的乙烯单体的共聚反应中获得。
(甲基)丙烯酸丁酯、(甲基)丙烯酸-2-乙基己酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸戊酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸异壬酯等可单独或-起用作含有C1～C12的烷基的(甲基)丙烯酸酯单体。并且，(甲基)丙烯酸-2-羟乙酯、(甲基)丙烯酸-2-羟丙酯、2-羟基乙二醇(甲基)丙烯酸酯、2-羟基丙二醇(甲基)丙烯酸酯等可用作含有羟基的乙烯单体。
除了由化学式(1)表示的有机硅烷化合物和丙烯酸基体树脂之外，在测试中可以使用交联剂。甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、1，6-己二异氰酸酯、甲苯二异氰酸酯的三甲醇丙烷加合物等可用作交联剂。
另外，根据需要可将选自增塑剂、丙烯酸低聚物、乳化剂、双折射性的低分子量化合物、环氧树脂、硬化剂、紫外稳定剂、抗氧化剂、着色剂、改性剂、填料等中的添加剂添加到丙烯酸基体树脂。
具体实施方式
本发明的实用和目前优选的实施方式在下列实施例中示出。但是，应该理解，本领域的技术人员可根据本公开在本发明的主旨和范围内进行修正和改进。
[实施例]
实施例1：氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)]的合成
在装备有温度计和冷凝器的1升反应器中加入200mLTHF、40g(0.319mol)烷基氰基乙酸酯和40g(0.327mol)三甲氧基硅烷。加热到60℃后，添加0.05g氯铂酸。反应4小时后，去除溶剂和未反应的反应物。通过真空蒸馏获得73g氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)](产率：91％)。
制备的氰基乙酰氧基丙基三甲氧基硅烷为无色液体。NMR分析结果如下：
1H NMR(CDCl3，300MHz)：0.70(t，2H)，1.83(p，2H)，3.50(s，2H)，3.61(s，9H)，4.22(t，2H)
13C NMR(CDCl3，300MHz)：4.6，21.4，24.0，49.9，67.9，113.3，163.1
实施例2：N-甲基-N-(3-甲氧基甲硅烷基丙基)氰基乙酰胺[化学式
(3)]的合成
在装备有温度计、冷凝器和玻璃滴瓶的1升反应器中加入200mL二乙醚和11g(0.11mol)氰基乙酰氯。经室温下在氮气气氛中搅拌后，采用滴液漏斗在30分钟内向反应器中缓慢加入溶解在100mL二乙醚中的20g(0.104mol)N-甲基氨基丙基甲氧基硅烷和11g(0.14mol)吡啶。在室温下搅拌反应混合物2小时后，将沉淀的吡啶盐、溶剂和未反应的反应物去除。通过真空蒸馏获得21g N-甲基-N-(3-甲氧基甲硅烷基丙基)氰基乙酰胺[化学式(3)](产率：75％)。
制备的N-甲基-N-(3-甲氧基甲硅烷基丙基)氰基乙酰胺为无色液体。NMR分析结果如下：
1H NMR(CDCl3，300MHz)：0.65(t，2H)，1.28(p，2H)，2.97(s，3H)，3.37(s，9H)，3.47(s，9H)，3.55(t，2H)
13C NMR(CDCl3，300MHz)：3.54，21.0，24.95，36.01，48.57，50.73，115.19，162.32
实施例3
(丙烯酸共聚物的制备)
在装备有氮气回流装置和冷却装置的1000cc反应器中加入包含98重量份的丙烯酸正乙酯(EA)和2重量份的甲基丙烯酸-2-羟乙酯(2-HEMA)的单体混合物。随后，加入230重量份作为溶剂的乙酸乙酯(EAc)。为了去除氧气，以氮气净化20分钟后，将反应器维持在70℃。均化后，加入0.03重量份在乙酸乙酯中稀释到50％的作为反应引发剂的偶氮二异丁腈(AIBN)。反应7小时后，获得分子量为
(采用聚苯乙烯标准样品测量)的丙烯酸共聚物。
(丙烯酸树脂组合物的制备)
向以上制备的100重量份丙烯酸共聚物中加入1.5重量份作为多官能异氰酸酯交联剂的三甲醇丙烷的甲苯二异氰酸酯加合物和0.1重量份在实施例1中制备的氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)]。将混合物适当稀释、均匀混合、涂敷在剥离膜上并且干燥以获得30微米厚的平滑的丙烯酸树脂层。以上述制备的丙烯酸树脂层涂敷用电晕处理的聚酯膜(185微米厚)。将聚酯膜切成适当尺寸以用于测试(宽90mm，长170mm)。
实施例4
在丙烯酸树脂组合物的制备过程中，除了使用在实施例2中制备的N-甲基-N-(3-甲氧基甲硅烷基丙基)氰基乙酰胺[化学式(3)]代替在实施例1中制备的氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)]之外，重复实施例3的步骤。
比较实施例1
在丙烯酸树脂组合物的制备过程中，除了不添加在实施例1中制备的氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)]之外，重复实施例3的步骤。
比较实施例2
在丙烯酸树脂组合物的制备过程中，除了使用(3-缩水甘油氧基丙基)三甲氧基硅烷代替在实施例1中制备的氰基乙酰氧基丙基三甲氧基硅烷[化学式(2)]之外，重复实施例3的步骤。
(粘合性的测量)
以如下方式测量在实施例3和4以及比较实施例1和2中制备的丙烯酸树脂组合物对玻璃的粘合性：
将其上为实施例3和4以及比较实施例1和2中制备的各丙烯酸树脂组合物与干净的玻璃层压的PET膜，并在室温下放置1小时。随后，将它们在i)室温条件(在室温下10小时)，ii)干燥条件(在60℃下10小时)和iii)湿条件(在60℃和R.H.90％下10小时)下放置。之后，将它们在室温下放置2小时。采用张力试验机，在300mm/min和180°剥离粘结测试对玻璃的粘合性。结果如下表1所示。
表1
如表1所示，和比较实施例1和2的那些丙烯酸树脂组合物相比，在室温条件、干燥条件和湿条件下，使用了由化学式(1)表示的本发明的新的有机硅烷化合物的实施例3和4的丙烯酸树脂组合物显示了优异的对玻璃的粘合强度。
工业实用性
从上述内容明显看出，根据本发明的新的有机硅烷化合物在各种应用中有益于改进有机树脂对无机填料的亲合性或改进包含基体树脂的涂层对基板的粘合性。特别地，它有益于改进用于液晶显示器的偏振片粘合剂对玻璃基板的粘合性，即使在热湿条件下，该粘合性随时间的变化也很小。
本领域的技术人员会理解到，上述公开的概念和具体实施方式可容易地用作改进或设计用于实施与本发明相同目的的其它的实施方式的基础。本领域的技术人员也会理解到，这些等效的实施方式不偏离如附权利要求中所述的本发明的主旨和范围。
Claims (5)
1.一种由下述化学式(1)表示的有机硅烷化合物：
化学式1
其中，R1、R2和R3各自独立地为氢或C1～C3的烷基；X为-NR4-、氧或硫，其中R4是氢或C1～C3的烷基；n是从3到10的整数；并且j是从1到3的整数。
2.根据权利要求1所述的由化学式(1)表示的有机硅烷化合物，该有机硅烷化合物通过使1-链烯基氰基乙酸酯和三烷氧基硅烷在氯铂酸催化剂或铂-乙烯基硅氧烷催化剂存在的条件下反应而制备。
3.根据权利要求1所述的由化学式(1)表示的有机硅烷化合物，该有机硅烷化合物通过使1-链烯基氰基乙酸酯和三氯硅烷在氯铂酸催化剂或铂-乙烯基硅氧烷催化剂存在的条件下反应，并进行甲醇分解而制备。
4.根据权利要求1所述的由化学式(1)表示的有机硅烷化合物，其中，化学式(1)中的取代基R1是氢。
5.根据权利要求1所述的由化学式(1)表示的有机硅烷化合物，该有机硅烷化合物是由下述化学式(2)表示的氰基乙酰氧基丙基三甲氧基硅烷或由下述化学式(3)表示的N-甲基-N-(3-三甲氧基甲硅烷基丙基)氰基乙酰胺：
化学式2
化学式3
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- 2006-10-19 AT AT06799339T patent/ATE501228T1/de not_active IP Right Cessation
- 2006-10-19 DE DE602006020608T patent/DE602006020608D1/de active Active
- 2006-10-19 CN CN200680039148XA patent/CN101291941B/zh active Active
- 2006-10-20 TW TW095138682A patent/TWI324627B/zh active
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Also Published As
| Publication number | Publication date |
|---|---|
| JP4819128B2 (ja) | 2011-11-24 |
| DE602006020608D1 (de) | 2011-04-21 |
| TWI304405B (en) | 2008-12-21 |
| CN101292007A (zh) | 2008-10-22 |
| JP2009512753A (ja) | 2009-03-26 |
| KR100840114B1 (ko) | 2008-06-19 |
| JP4927856B2 (ja) | 2012-05-09 |
| CN101291941A (zh) | 2008-10-22 |
| JP2009512683A (ja) | 2009-03-26 |
| KR20070043557A (ko) | 2007-04-25 |
| TWI324627B (en) | 2010-05-11 |
| TW200716718A (en) | 2007-05-01 |
| KR20070043558A (ko) | 2007-04-25 |
| TW200716657A (en) | 2007-05-01 |
| CN101292007B (zh) | 2012-07-25 |
| KR100822142B1 (ko) | 2008-04-14 |
| ATE501228T1 (de) | 2011-03-15 |
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