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JP4927856B2 - Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device - Google Patents

Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device Download PDF

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JP4927856B2
JP4927856B2 JP2008536497A JP2008536497A JP4927856B2 JP 4927856 B2 JP4927856 B2 JP 4927856B2 JP 2008536497 A JP2008536497 A JP 2008536497A JP 2008536497 A JP2008536497 A JP 2008536497A JP 4927856 B2 JP4927856 B2 JP 4927856B2
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adhesive
polarizing plate
liquid crystal
display device
crystal display
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JP2009512683A (en
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マイケル・ジェイ・キム
ノマ・キム
アンナ・イ
セラ・キム
サキー・チャン
スンチュル・リム
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LG Chem Ltd
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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
    • 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
    • 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
    • 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
    • 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
    • C09J11/08—Macromolecular additives
    • 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
    • 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
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Polarising Elements (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to a pressure-sensitive adhesive composition, and more precisely, a pressure-sensitive adhesive composition containing an organic silane compound that exhibits excellent initial adhesive strength on a substrate, and does not leave any of the adhesive behind when removed because the adhesive power is not excessively increased even at high temperature or at high temperature and high humidity.

Description

本発明は、新規な有機シラン化合物に関する。より詳しくは有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用であり、特に、液晶表示装置の偏光板用接着剤のガラス基板との接着性を向上させ、高温高湿下においても経時変化を少なくするために有用である、新規な有機シラン化合物に関するものである。   The present invention relates to a novel organosilane compound. More specifically, it is useful for various applications for the purpose of increasing the affinity between the organic resin and the inorganic filler, or for improving the adhesion between the coating layer containing the matrix resin and the base material. The present invention relates to a novel organosilane compound that is useful for improving the adhesion of a polarizing plate adhesive to a glass substrate and reducing a change with time even under high temperature and high humidity.

従来のシラン化合物を含有する接着剤組成物としては、エポキシ基を有するシラン化合物を含む接着剤組成物が開示されている（特許文献１参照）。また、炭化水素基を有するシラン化合物を含む接着剤組成物が開示されている（特許文献２参照）。   As an adhesive composition containing a conventional silane compound, an adhesive composition containing a silane compound having an epoxy group is disclosed (see Patent Document 1). Moreover, the adhesive composition containing the silane compound which has a hydrocarbon group is disclosed (refer patent document 2).

しかし、前記のようなシラン化合物を含む接着剤組成物の場合、基板または偏光板が実際に使用される環境において要求される程度の適切な接着力を保持することができず、高温高湿の条件で接着力が過度に上昇する、あるいは剥離後に接着剤が基材に残存するという問題点があった。
特開平０２−４１８３５７号公報（特許第３０２２９９３号公報） 特開平０７−３３１２０４号公報 However, in the case of the adhesive composition containing the silane compound as described above, it is not possible to maintain an appropriate adhesive force as required in an environment where the substrate or the polarizing plate is actually used, There was a problem that the adhesive force increased excessively under certain conditions, or the adhesive remained on the substrate after peeling.
JP 02-418357 A (Patent No. 3022993) JP 07-331204 A

前記のような従来の技術の問題点を解決するために、本発明は、有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用である新規な有機シラン化合物を提供することを目的とする。   In order to solve the problems of the prior art as described above, the present invention aims to increase the affinity between the organic resin and the inorganic filler, or the adhesion between the coating layer containing the matrix resin and the substrate. An object of the present invention is to provide a novel organosilane compound that is useful for various purposes for the purpose of improvement.

本発明の他の目的は、液晶表示装置の偏光板用接着剤に含有させると、ガラス基板との接着性を向上させ、高温高湿下においても経時変化を少なくする、新規な有機シラン化合物を提供することである。   Another object of the present invention is to provide a novel organosilane compound that, when incorporated in an adhesive for a polarizing plate of a liquid crystal display device, improves adhesion to a glass substrate and reduces aging even under high temperature and high humidity. Is to provide.

前記目的を達成するために、本発明は、下記化学式１で表される有機シラン化合物を提供する。

Figure 0004927856
〔式中、Ｒ１、Ｒ２およびＲ３は、それぞれ独立に、水素または炭素数１〜３のアルキル基であり、Ｘは−ＮＲ４−（式中、Ｒ４は水素または炭素数１〜３のアルキル基である）、酸素原子、または硫黄原子であり、ｎは３乃至１０の整数であり、ｊは１乃至３の整数である。〕 In order to achieve the above object, the present invention provides an organosilane compound represented by the following chemical formula 1.
Figure 0004927856
 [Wherein R 1 , R 2 and R 3 each independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms, X represents —NR 4 — (wherein R 4 represents hydrogen or 1 to 3 carbon atoms, 3 is an alkyl group of 3), an oxygen atom, or a sulfur atom, n is an integer of 3 to 10, and j is an integer of 1 to 3. ]

以下、本発明を詳しく説明する。   The present invention will be described in detail below.

本発明の新規な有機シラン化合物は化学式１で表されることを特徴とする。   The novel organosilane compound of the present invention is represented by Formula 1.

化学式１で表示される有機シラン化合物は、１段階（one‐step）のプロセスまたは２段階（two‐step）のプロセスで製造することができる。   The organosilane compound represented by Chemical Formula 1 can be manufactured by a one-step process or a two-step process.

１段階のプロセスでは、本有機シラン化合物は、１‐アルケニルシアノアセテートとトリアルコキシシランとを、塩化白金酸触媒、 カールシュテット（Karstedt）触媒（即ち、塩化白金酸とｓｙｍ‐ジビニルテトラメチルジシロキサンとの錯体）、ジクロロビストリフェニルフォスフィン白金（ＩＩ）、シス‐ジクロロビスアセトニトリル白金（ＩＩ）、またはジカルボニルジクロロ白金（ＩＩ）の存在下で反応させることによって製造することができる。好ましくは、触媒は、塩化白金酸または白金‐ビニルシロキサン錯体から選ばれる。あるいは、本有機シラン化合物は、３級アミンの存在下で、シアノアセチルクロライドとＮ‐アルキルアミノアルキルトリアルコキシドとを反応させることによって製造することもできる。   In a one-step process, the organosilane compound comprises 1-alkenyl cyanoacetate and trialkoxysilane, a chloroplatinic acid catalyst, a Karlstedt catalyst (ie, chloroplatinic acid and sym-divinyltetramethyldisiloxane). Complex), dichlorobistriphenylphosphine platinum (II), cis-dichlorobisacetonitrile platinum (II), or dicarbonyldichloroplatinum (II). Preferably, the catalyst is selected from chloroplatinic acid or a platinum-vinylsiloxane complex. Alternatively, the organosilane compound can also be produced by reacting cyanoacetyl chloride and N-alkylaminoalkyltrialkoxide in the presence of a tertiary amine.

有機シラン化合物を製造するための２段階のプロセスでは、先ず、１‐アルケニルシアノアセテートとトリクロロシランとを塩化白金酸触媒または白金‐ビニルシロキサン触媒の存在下で反応させた後、メタノールを用いて反応生成物のメタノリシス（methanolysis）を行うことによって新規有機シラン化合物を製造することができる。   In the two-step process for producing organosilane compounds, first, 1-alkenyl cyanoacetate and trichlorosilane are reacted in the presence of a chloroplatinic acid catalyst or a platinum-vinylsiloxane catalyst, and then reacted with methanol. A novel organosilane compound can be produced by methanolysis of the product.

化学式１で表される有機シラン化合物は、１‐アルケニルシアノアセテートとトリアルコキシシランとを塩化白金酸触媒の存在下で反応させることによって製造することもでき、３級アミンの存在下でシアノアセチルクロライドとＮ‐アルキルアミノアルキルトリアルコキシドとを反応させることによって製造することもできる。   The organosilane compound represented by Chemical Formula 1 can also be produced by reacting 1-alkenyl cyanoacetate with trialkoxysilane in the presence of a chloroplatinic acid catalyst, and cyanoacetyl chloride in the presence of a tertiary amine. It can also be produced by reacting N-alkylaminoalkyltrialkoxide with N-alkylaminoalkyltrialkoxide.

上記反応は、クロロホルム、メチレンクロライド、ジクロロエタン等のハロゲン化アルキル溶媒；テトラハイドロフラン、ジオキサン等のような環状エーテル溶媒；またはベンゼン、トルエン、キシレン等のような芳香族有機溶媒中で行うことができる。   The above reaction can be carried out in a halogenated alkyl solvent such as chloroform, methylene chloride, dichloroethane; a cyclic ether solvent such as tetrahydrofuran, dioxane or the like; or an aromatic organic solvent such as benzene, toluene, xylene or the like. .

反応は、１０乃至２００℃の温度範囲で実施されることが望ましく、より望ましくは５０乃至１５０℃の温度範囲で実施される。また、精製のために真空蒸留を実施することもできる。   The reaction is preferably performed in a temperature range of 10 to 200 ° C, more preferably in a temperature range of 50 to 150 ° C. Also, vacuum distillation can be performed for purification.

前記のような反応を通じて製造される化学式１で表される本発明の有機シラン化合物の置換基Ｒ１は、特に、水素であることが望ましい。 The substituent R 1 of the organosilane compound of the present invention represented by the chemical formula 1 produced through the above reaction is particularly preferably hydrogen.

化学式１で表される本発明の有機シラン化合物の具体例には、下記化学式２で表されるシアノアセトキシプロピルトリメトキシシラン、下記化学式３で表される Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミドが含まれる。

Figure 0004927856
Figure 0004927856
 Specific examples of the organosilane compound of the present invention represented by the chemical formula 1 include cyanoacetoxypropyltrimethoxysilane represented by the following chemical formula 2, N-methyl-N- (3-trimethoxy represented by the following chemical formula 3 Silylpropyl) cyanoacetamide is included.
Figure 0004927856
Figure 0004927856

化学式１で表れる本発明の有機シラン化合物は、アクリル系樹脂組成物、熱硬化性樹脂組成物、または熱可塑性樹脂組成物等に使用するのに適している。   The organosilane compound of the present invention represented by Chemical Formula 1 is suitable for use in an acrylic resin composition, a thermosetting resin composition, a thermoplastic resin composition, or the like.

前記のような方法で製造される化学式１で表される本発明の新規な有機シラン化合物は、マトリックス樹脂に有用に用いることができる。基材に対する接着力を向上させる添加剤（接着促進剤）としての効果があるかを確認するために、本発明の有機シラン化合物を用いて、アクリル系マトリックス樹脂を合成し、ガラスに対する接着力を試験した。   The novel organosilane compound of the present invention represented by Chemical Formula 1 produced by the above method can be usefully used for a matrix resin. In order to confirm whether there is an effect as an additive (adhesion promoter) that improves the adhesion to the base material, the organic silane compound of the present invention is used to synthesize an acrylic matrix resin and to improve the adhesion to glass. Tested.

アクリル系マトリックス樹脂は、炭素数１乃至１２のアルキル基を有する（メタ）アクリル酸エステルモノマーと水酸基を含むビニル系モノマーとを共重合させることによって得ることができる。   The acrylic matrix resin can be obtained by copolymerizing a (meth) acrylic acid ester monomer having an alkyl group having 1 to 12 carbon atoms and a vinyl monomer containing a hydroxyl group.

炭素数１乃至１２のアルキル基を有する（メタ）アクリル酸エステルモノマーとして、ブチル（メタ）アクリレート、２‐エチルヘキシル（メタ）アクリレート、エチル（メタ）アクリレート、メチル（メタ）アクリレート、ｎ‐プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、ｔ‐ブチル（メタ）アクリレート、ペンチル（メタ）アクリレート、ｎ‐オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、またはイソノニル（メタ）アクリレート等を、単独または２種以上混合して使用することができる。また、前記水酸基を含むビニル系モノマーとして、２‐ヒドロキシエチル（メタ）アクリレート、２‐ヒドロキシプロピル（メタ）アクリレート、２‐ヒドロキシエチレングリコール（メタ）アクリレート、または２‐ヒドロキシプロピレングリコール（メタ）アクリレート等を使用することができる。   Examples of the (meth) acrylic acid ester monomer having an alkyl group having 1 to 12 carbon atoms include butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) ) Acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, or isononyl (meth) acrylate, alone or in combination They can be used in combination. Examples of the vinyl monomer containing a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, and 2-hydroxypropylene glycol (meth) acrylate. Can be used.

前記試験において、化学式１で表される本発明の有機シラン化合物およびアクリル系マトリックス樹脂に加えて、架橋剤を使用することができる。この架橋剤として、トリレンジイソシアナート、ジフェニルメタンジイソシアナート、ヘキサメチレンジイソシアナート、またはトリレンジイソシアナートのトリメチロールプロパン付加体等を使用することができる。   In the test, a crosslinking agent can be used in addition to the organosilane compound of the present invention represented by Chemical Formula 1 and the acrylic matrix resin. As the crosslinking agent, tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, or a trimethylolpropane adduct of tolylene diisocyanate can be used.

また、前記アクリル系マトリックス樹脂に、必要に応じて、可塑剤、アクリル系オリゴマー、乳化剤、複屈折性低分子量化合物、エポキシ樹脂、硬化剤、紫外線安定剤、酸化防止剤、着色剤、改質剤、または フィラー等の添加剤を添加することもできる。   In addition, the acrylic matrix resin may include a plasticizer, an acrylic oligomer, an emulsifier, a birefringent low molecular weight compound, an epoxy resin, a curing agent, an ultraviolet stabilizer, an antioxidant, a colorant, and a modifier as necessary. Or additives such as fillers can be added.

以下、本発明の理解を助けるために望ましい実施例を提示するが、下記の実施例は本発明を例示するものであり、本発明の範囲が下記の実施例に限定されるものではない。   Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples illustrate the present invention, and the scope of the present invention is not limited to the following examples.

［実施例１］：シアノアセトキシプロピルトリメトキシシラン （cyanoacetoxypropyl trimethoxy silane、化学式２）の合成
温度計と凝縮機が備えられた１Ｌの反応器に、ＴＨＦ２００ｍＬ、アルキルシアノアセテート４０ｇ（０．３１９ｍｏｌ）、及びトリメトキシシラン４０ｇ（０．３２７ｍｏｌ）を入れた。温度を６０℃に高めた後、塩化白金酸０．０５ｇを添加し４時間反応させた。反応終了後、溶媒及び未反応物を除去し、真空蒸留して、シアノアセトキシプロピルトリメトキシシラン（化学式２）７３ｇを得た。収率は９１％であった。 [Example 1]: Synthesis of cyanoacetoxypropyl trimethoxysilane (Chemical Formula 2) In a 1 L reactor equipped with a thermometer and a condenser, 200 mL of THF, 40 g of alkyl cyanoacetate (0.319 mol), and 40 g (0.327 mol) of trimethoxysilane was added. After raising the temperature to 60 ° C., 0.05 g of chloroplatinic acid was added and allowed to react for 4 hours. After completion of the reaction, the solvent and unreacted substances were removed and vacuum distillation was performed to obtain 73 g of cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2). The yield was 91%.

製造したシアノアセトキシプロピルトリメトキシシランは、無色の液体であった。ＮＭＲ分析の結果は次の通りである。
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 The produced cyanoacetoxypropyltrimethoxysilane was a colorless liquid. The results of NMR analysis are as follows.
1 H NMR (CDCl 3 , 300 MHz): 0.70 (t, 2H), 1.83 (p, 2H), 3.50 (s, 2H), 3.61 (s, 9H), 4.22 ( t, 2H)
13 C NMR (CDCl 3 , 300 MHz): 4.6, 21.4, 24.0, 49.9, 67.9, 113.3, 163.1

［実施例２］：Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（N-methyl-N-(3-trimethoxysilylpropyl)cyanoacetamide、化学式３）の合成
温度計、凝縮機、及び滴下用ガラスボトルが備えられた１Ｌの反応器に、ジエチルエテール２００ｍＬ及びシアノアセチルクロライド１１ｇ（０．１１ｍｏｌ）を入れ、常温、窒素雰囲気で攪拌した。Ｎ‐メチルアミノプロピルメトキシシラン（N-methylaminopropyl trimethoxysilane）２０ｇ（０．１０４ｍｏｌ）及びピリジン１１ｇ（０．１４ｍｏｌ）をジエチルエテール１００ｍＬに溶解した溶液を、滴下用ガラス漏斗を用いて反応器に徐々に添加した。この反応物を２時間間常温で攪拌した後、沈殿したピリジニウム塩、溶媒、及び未反応物を除去した後、真空蒸留して、Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（化学式３）２１ｇを得た。収率は７５％であった。 Example 2 Synthesis of N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide (N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide, Chemical Formula 3) Thermometer, condenser, and dropping In a 1 L reactor equipped with a glass bottle, 200 mL of diethyl ether and 11 g (0.11 mol) of cyanoacetyl chloride were added and stirred at room temperature in a nitrogen atmosphere. A solution prepared by dissolving 20 g (0.104 mol) of N-methylaminopropyl trimethoxysilane and 11 g (0.14 mol) of pyridine in 100 mL of diethylether is gradually added to the reactor using a dropping funnel. Added. The reaction was stirred for 2 hours at room temperature, then the precipitated pyridinium salt, solvent and unreacted material was removed and then vacuum distilled to give N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide. (Chemical formula 3) 21 g was obtained. The yield was 75%.

製造した Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミドは、無色の液体であった。ＮＭＲ分析の結果は次の通りである。
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 The produced N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide was a colorless liquid. The results of NMR analysis are as follows.
1 H NMR (CDCl 3 , 300 MHz): 0.65 (t, 2H), 1.28 (p, 2H), 2.97 (s, 3H), 3.37 (s, 9H), 3.47 ( s, 9H), 3.55 (t, 2H)
13 C NMR (CDCl 3 , 300 MHz): 3.54, 21.0, 24.95, 36.01, 48.57, 50.73, 115.19, 162.32

［実施例３］
（アクリル系共重合体の製造）
窒素ガスの還流ユニットと、温度調節が容易な冷却装置とが設けられた、１、０００ｃｃの反応器に、ｎ‐エチルアクリレート（ＥＡ）９８重量部、及び２‐ヒドロキシエチルメタアクリレート（２‐ＨＥＭＡ）２重量部とを含む単量体混合物を投入した。その後、溶剤としてエチルアセテート（ＥＡｃ）２３０重量部を投入した。酸素を除去するために窒素ガスを２０分間パージングした後、この反応器を７０℃で保持した。均一化した後、反応開始剤として、エチルアセテート中５０％の濃度に希釈したアゾビスイソブチロニトリル（ＡＩＢＮ）０．０３重量部を投入した。この混合物を７時間反応させた後、分子量が（ポリスチレンの標準サンプルを用いて測定して）９０万であるアクリル系共重合体が得られた。 [Example 3]
(Manufacture of acrylic copolymer)
A 1,000 cc reactor equipped with a nitrogen gas reflux unit and a cooling device with easy temperature control was charged with 98 parts by weight of n-ethyl acrylate (EA) and 2-hydroxyethyl methacrylate (2-HEMA). ) A monomer mixture containing 2 parts by weight was charged. Thereafter, 230 parts by weight of ethyl acetate (EAc) was added as a solvent. After purging with nitrogen gas for 20 minutes to remove oxygen, the reactor was held at 70 ° C. After homogenization, 0.03 parts by weight of azobisisobutyronitrile (AIBN) diluted to a concentration of 50% in ethyl acetate was added as a reaction initiator. After the mixture was reacted for 7 hours, an acrylic copolymer having a molecular weight of 900,000 (measured using a standard polystyrene sample) was obtained.

（アクリル系樹脂組成物の製造）
製造したアクリル系共重合体１００重量部に、多官能性イソシアネート系架橋剤としてトリメチロールプロパンのトリレンジイソシアナート付加物１．５重量部と、実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）０．１重量部とを添加した。この組成物を適切な濃度に希釈し、均一に混合した後、ＰＥＴフィルム上にコーティングした。 (Manufacture of acrylic resin composition)
To 100 parts by weight of the produced acrylic copolymer, 1.5 parts by weight of a tolylene diisocyanate adduct of trimethylolpropane as a polyfunctional isocyanate-based crosslinking agent, and the cyanoacetoxypropyltrimethoxysilane synthesized in Example 1 ( Chemical formula 2) 0.1 part by weight was added. This composition was diluted to an appropriate concentration, mixed uniformly, and then coated on a PET film.

［実施例４］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）の代わりに、実施例２で合成したＮ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（化学式３）を使用したことを除いて、実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。 [Example 4]
Use of N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide (Chemical Formula 3) synthesized in Example 2 instead of cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2) synthesized in Example 1 Except for, the acrylic resin composition was produced in the same manner as in Example 3.

［比較例１］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）を添加しなかったことを除いて、実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。 [Comparative Example 1]
An acrylic resin composition was produced in the same manner as in Example 3 except that cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2) synthesized in Example 1 was not added.

［比較例２］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）の代わりに３‐ グリシドキシプロピルトリメトキシシラン（glycidoxypropyl)trimethoxysilane）を使用したことを除いては実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。 [Comparative Example 2]
An acrylic resin was prepared in the same manner as in Example 3 except that 3-glycidoxypropyl trimethoxysilane was used instead of cyanoacetoxypropyltrimethoxysilane (chemical formula 2) synthesized in Example 1. Production of a resin-based resin composition was carried out.

〔接着力の測定〕
実施例３乃至４及び比較例１乃至２で製造したアクリル系樹脂組成物のガラスに対する接着力を次のような方法で評価した。 [Measurement of adhesive strength]
The adhesive strength of the acrylic resin compositions produced in Examples 3 to 4 and Comparative Examples 1 and 2 to glass was evaluated by the following method.

実施例３乃至４及び比較例１乃至２で製造したアクリル系樹脂組成物がそれぞれコーティングされたＰＥＴフィルムを、清潔なガラス板と共に加圧ローラーを用いてラミネートし、常温で１時間間保持した。その後、ｉ）常温条件（常温で１０時間間放置）、ｉｉ）ｄｒｙ条件（６０℃の温度で１０時間放置）、およびｉｉｉ）ｗｅｔ条件（６０℃、９０％相対湿度の条件で１０時間放置）に保持した後、再び常温で２時間保持した。次いで、 引張試験機を用いて３００ｍｍ／分の速度および１８０°の剥離角度でガラスに対する接着力（１８０℃ 剥離強度）を測定した。結果を下記表１に示す。   The PET films coated with the acrylic resin compositions produced in Examples 3 to 4 and Comparative Examples 1 to 2 were laminated with a clean glass plate using a pressure roller, and held at room temperature for 1 hour. Then, i) normal temperature conditions (left at normal temperature for 10 hours), ii) dry conditions (left at 60 ° C. for 10 hours), and iii) wet conditions (left at 60 ° C., 90% relative humidity for 10 hours) And then held again at room temperature for 2 hours. Subsequently, the adhesive strength (180 degreeC peeling strength) with respect to glass was measured with the speed | rate of 300 mm / min and the peeling angle of 180 degrees using the tensile tester. The results are shown in Table 1 below.

Figure 0004927856
Figure 0004927856

表１に示したように、本発明の化学式１で表される新規な有機シラン化合物を用いた実施例３及び４のアクリル系樹脂組成物は、比較例１及び２のアクリル系樹脂組成物と比べて、常温条件、ｄｒｙ条件、ｗｅｔ条件の全てにおいて、ガラス接着力に優れていることが分かる。   As shown in Table 1, the acrylic resin compositions of Examples 3 and 4 using the novel organosilane compound represented by Chemical Formula 1 of the present invention are the same as the acrylic resin compositions of Comparative Examples 1 and 2. In comparison, it can be seen that the glass adhesive force is excellent in all of the room temperature conditions, the dry conditions, and the wet conditions.

本発明による新規な有機シラン化合物は、有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用であり、特に、液晶表示装置の偏光板用接着剤のガラス基板との接着性を向上させ、高温高湿下における経時変化を低下させるために有用である。   The novel organosilane compound according to the present invention is useful for various applications for the purpose of increasing the affinity between the organic resin and the inorganic filler, or for improving the adhesion between the coating layer containing the matrix resin and the substrate. In particular, it is useful for improving the adhesiveness of the adhesive for a polarizing plate of a liquid crystal display device to a glass substrate and reducing the change with time under high temperature and high humidity.

これまで、本発明の概念および具体例を詳しく説明してきたが、これらの記載に基づいて、本発明の技術思想の範囲内で他の多様な変形及び修正が可能であることが当業者に理解されるであろう。当業者であれば、このような変形及び修正が添付された特許請求の精神および範囲に包含されること理解するであろう。   Although the concept and specific examples of the present invention have been described in detail so far, those skilled in the art will understand that various other variations and modifications can be made within the scope of the technical idea of the present invention based on these descriptions. Will be done. Those skilled in the art will appreciate that such changes and modifications are encompassed within the spirit and scope of the appended claims.

Claims (8)

有機シラン化合物を含む、液晶表示装置の偏光板用接着剤のための接着剤組成物であって、
前記有機シラン化合物が下記化学式１：
Figure 0004927856
〔式中、Ｒ１、Ｒ２およびＲ３は、それぞれ独立に、水素または炭素数１〜３のアルキル基であり、Ｘは、−ＮＲ４−（式中、Ｒ４は水素または炭素数１〜３のアルキル基である）、酸素原子、または硫黄原子であり、ｎは３乃至１０の整数であり、ｊは１乃至３の整数である〕
で表される、接着剤組成物。 An adhesive composition for an adhesive for a polarizing plate of a liquid crystal display device comprising an organosilane compound,
The organosilane compound is represented by the following chemical formula 1 :
Figure 0004927856
 [Wherein R 1 , R 2 and R 3 each independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms, and X represents —NR 4 — (wherein R 4 represents hydrogen or carbon number 1 An alkyl group of ˜3), an oxygen atom, or a sulfur atom, n is an integer of 3 to 10, and j is an integer of 1 to 3.
An adhesive composition represented by: １‐アルケニルシアノアセテートとトリアルコキシシランとを塩化白金酸触媒または白金‐ビニルシロキサン触媒の存在下で反応させることによって製造されることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。 2. The polarizing plate of a liquid crystal display device according to claim 1, wherein the polarizing plate is produced by reacting 1 -alkenyl cyanoacetate with trialkoxysilane in the presence of a chloroplatinic acid catalyst or a platinum-vinylsiloxane catalyst. An adhesive composition for an adhesive . １‐アルケニルシアノアセテートとトリクロロシランとを塩化白金酸触媒または白金‐ビニルシロキサン触媒の存在下で反応させた後、メタノリシスを行うことによって製造されることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。 2. The liquid crystal according to claim 1, which is produced by reacting 1 -alkenyl cyanoacetate with trichlorosilane in the presence of a chloroplatinic acid catalyst or a platinum-vinylsiloxane catalyst and then performing methanolysis. An adhesive composition for a polarizing plate adhesive of a display device . １‐アルケニルシアノアセテートとトリアルコキシシランとを塩化白金酸触媒の存在下で反応させることによって製造されることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。 The adhesive for a polarizing plate of a liquid crystal display device according to claim 1, wherein the adhesive is produced by reacting 1 -alkenyl cyanoacetate and trialkoxysilane in the presence of a chloroplatinic acid catalyst . Adhesive composition . シアノアセチルクロライドとＮ‐アルキルアミノアルキルトリアルコキシドとを３級アミンの存在下で反応させることによって製造されることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。Characterized in that it is prepared by reacting in the presence of a sheet anode acetyl chloride and N- alkylaminoalkyl trialkoxide and the tertiary amine, the adhesive for polarizing plate of the liquid crystal display device according to claim 1 Adhesive composition for . 化学式１中の置換基Ｒ１が水素であることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。Wherein the substituent R 1 in Formula 1 is hydrogen, an adhesive composition for a polarizing plate adhesive for a liquid crystal display device according to claim 1. 前記有機シラン化合物が、下記化学式２：
Figure 0004927856
で表されるシアノアセトキシプロピルトリメトキシシラン、または
下記化学式３：
Figure 0004927856
で表されるＮ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミドであることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。The organosilane compound has the following chemical formula 2:
Figure 0004927856
 Or cyanoacetoxypropyltrimethoxysilane represented by the following chemical formula 3:
Figure 0004927856
 The adhesive composition for an adhesive for a polarizing plate of a liquid crystal display device according to claim 1, characterized in that it is N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide represented by the formula: . アクリル系樹脂組成物、熱硬化性樹脂組成物、または熱可塑性樹脂組成物に使用されることを特徴とする、請求項１に記載の液晶表示装置の偏光板用接着剤のための接着剤組成物。 A acrylic resin composition, the thermosetting resin composition, or characterized in that it is used in the thermoplastic resin composition, an adhesive for adhesive for polarizing plate of the liquid crystal display device according to claim 1 Composition .
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