JP5380778B2 - Conductive composition - Google Patents
Conductive composition Download PDFInfo
- Publication number
- JP5380778B2 JP5380778B2 JP2007043364A JP2007043364A JP5380778B2 JP 5380778 B2 JP5380778 B2 JP 5380778B2 JP 2007043364 A JP2007043364 A JP 2007043364A JP 2007043364 A JP2007043364 A JP 2007043364A JP 5380778 B2 JP5380778 B2 JP 5380778B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- conductive composition
- acid
- organic solvent
- conductive
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 131
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- 239000003960 organic solvent Substances 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 44
- -1 cellosolves Chemical class 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
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- 229920005989 resin Polymers 0.000 claims description 35
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- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 12
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- 239000000654 additive Substances 0.000 claims description 9
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
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- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 125000005649 substituted arylene group Chemical group 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940068917 polyethylene glycols Drugs 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
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- 238000002834 transmittance Methods 0.000 description 27
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、導電性組成物に関し、さらに詳しくは、有機溶剤中でも安定に分散及び乳化された導電性組成物に関し、その導電性組成物は、均一塗膜の形成が可能であり、形成される塗膜は、透過度および抵抗特性が非常に優れており、各種帯電防止剤、電池、防食塗料、EMIシールド、化学センサー、表示素子、非線形材料、防食剤、接着剤、繊維、帯電防止塗料、導電性塗料、防食塗料、電着塗料、メッキプライマー、電気防食、電池の蓄電能力向上に適用可能である。 The present invention relates to a conductive composition, and more particularly to a conductive composition that is stably dispersed and emulsified in an organic solvent, and the conductive composition is capable of forming a uniform coating film. The coating film has very good permeability and resistance characteristics. Various antistatic agents, batteries, anticorrosive paints, EMI shields, chemical sensors, display elements, non-linear materials, anticorrosive agents, adhesives, fibers, antistatic paints, It can be applied to conductive paints, anticorrosion paints, electrodeposition paints, plating primers, cathodic protection, and battery storage capacity improvement.
電子工学及び光学製品の様々な性能が、導電性ポリマーを含有させることによって高められるという認識が高まっている。そのような物の例には、様々な電子工学的実施のみならず、帯電防止コーティング剤や帯電防止フィルムが含まれる。 There is a growing recognition that the various performances of electronics and optical products are enhanced by the inclusion of conductive polymers. Examples of such objects include antistatic coating agents and antistatic films as well as various electronic implementations.
電子工学及び光学製品は極めて高い耐水性や平滑性などを要求されるため、汎用有機溶剤系での検討が続けられると予想されるが、導電性ポリマーの多くが汎用有機溶剤系樹脂に対して十分に溶解または分散することができないために、不十分な導電性、不十分な透明性、低安定性、困難な加工条件を抱えている。 Since electronics and optical products are required to have extremely high water resistance and smoothness, it is expected that studies with general-purpose organic solvent systems will continue. Since it cannot be sufficiently dissolved or dispersed, it has insufficient conductivity, insufficient transparency, low stability, and difficult processing conditions.
例えば、特許文献1に開示されるスルホン酸基及び/またはカルボキシル基を有する水溶性アニリン系導電性ポリマーを主成分とする静電塗装用導電性プライマー組成物及び該組成物を用いた静電塗装方法は、簡便な方法で塗工可能であり、導電性に優れ、静電塗装効果の点でも優れている。しかしながら該発明で用いられている導電性ポリマーは水溶性であるため、帯電防止膜として十分な耐水性を有しておらず、上塗りとして水系のベースコートを用いた場合には導電性ポリマーの色がベースコートに混ざってしまい、また汎用溶剤系樹脂に配合した場合は、溶解または十分な分散性を得ることができないという課題点を有している。 For example, a conductive primer composition for electrostatic coating mainly comprising a water-soluble aniline-based conductive polymer having a sulfonic acid group and / or a carboxyl group disclosed in Patent Document 1, and electrostatic coating using the composition The method can be applied by a simple method, has excellent conductivity, and is excellent in terms of electrostatic coating effect. However, since the conductive polymer used in the present invention is water-soluble, it does not have sufficient water resistance as an antistatic film, and when a water-based base coat is used as an overcoat, the color of the conductive polymer is When mixed with a base coat and mixed with a general-purpose solvent-based resin, there is a problem in that it cannot be dissolved or sufficiently dispersible.
さらに、特許文献2に開示されるチオフェン混合物中の水を置換する溶媒交換法では、チオフェンとしてBaytronTM製剤を用いて水の一部又は全てを少なくとも一つの他の溶媒で効率よく置換する方法を提供している。しかしながら、水以外の溶媒として低アルキルアセトアミド、ジオール及びトリオールを含む低級アルコール、ピロリドン、低アルキルピロリドン、高アルキルピロリドン、低アルキルスルホキシド及びそれらの混合物や、好ましい低級アルコールとしてグリコール又はグリセリンを挙げ、適した低アルキルスルホキシドにはジメチルスルホキシド(DMSO)が含まれ、特に好ましい溶媒としてジメチルアセトアミド(DMAC)及びN−メチルピロリドン(NMP)が含まれており、さらにアセトニトリル、ベンゾニトリル、メチルアセテート、ジクロロメタン、ジエチルエーテル、ジメトキシエタン、N,N−ジメチルホルムアミド、ニトロベンゼン、ニトロメタン、プロピオニトリル及びプロピレン炭酸塩、ジクロロメタンとジブロモメタンなどが挙げられている。 Furthermore, the solvent exchange method for replacing water in a thiophene mixture disclosed in Patent Document 2 provides a method for efficiently replacing part or all of water with at least one other solvent using a Baytron ™ formulation as thiophene. doing. However, low alcohol acetamide, lower alcohols containing diol and triol, pyrrolidone, low alkyl pyrrolidone, high alkyl pyrrolidone, low alkyl sulfoxide and mixtures thereof as solvents other than water, and glycol or glycerin as preferred lower alcohols are suitable. Low alkyl sulfoxides include dimethyl sulfoxide (DMSO), particularly preferred solvents include dimethylacetamide (DMAC) and N-methylpyrrolidone (NMP), and acetonitrile, benzonitrile, methyl acetate, dichloromethane, diethyl ether. , Dimethoxyethane, N, N-dimethylformamide, nitrobenzene, nitromethane, propionitrile and propylene carbonate, dichloromethane and dibromine Such as methane are mentioned.
また、特許文献3や特許文献4では、良好な導電性、透明度、安定性、加水分解抵抗性及び加工特性を有する導電性組成物が報告されている。しかしながら該発明で用いられている組成物は導電性ポリマーの水飽和コロイド分散液として得られ、かなりの量の水溶媒で供給されている。この該発明で用いられている組成物を一つあるいはそれ以上の溶媒を選び、溶媒交換法を開発する試みがなされてはいるが、N−メチルピロリドン、ピロリドン、カプロラクタム、N−メチルカプロラクタム、N−オクチルピロリドン、他のプロトン性溶媒として例えば低級アルコールではメタノール、エタノール及びイソプロパノール、並びに水と低級アルコール及び他の水混和性有機溶媒例えばアセトンとの混合物を使用している。以上に示したような溶媒は極性が高すぎるため、工業的に汎用溶剤である酢酸エチル、メチルエチルケトン(MEK)、メチルイソブチルケトン(MIBK)、トルエン、シクロへキシルアノンなどを溶媒とする樹脂に該発明で用いられている組成物を添加すると、該発明で用いられている組成物の溶解性および分散性が著しく低下し均一で透明な塗膜を形成できなかったり、また溶媒の沸点が高すぎるため塗布可能な基材の種類が制限され適用範囲が限定されてしまったり、乾燥工程でのコスト面で問題があり、さらに溶剤によっては環境に対して悪影響を及ぼすハロゲン系溶媒が含まれるため工業的に不適である。
本発明の目的は、汎用の樹脂溶液と容易に混合でき、さらに乾燥工程で環境に対して負荷がかかりにくい溶剤中に、安定に分散及び乳化された導電性組成物を提供することにある。本発明の導電性組成物を使用することで、透過度および抵抗特性が非常に優れた均一な透明導電膜を生成させることができる。 An object of the present invention is to provide a conductive composition that can be easily mixed with a general-purpose resin solution and that is stably dispersed and emulsified in a solvent that is less burdensome to the environment in the drying step. By using the conductive composition of the present invention, it is possible to generate a uniform transparent conductive film having very excellent transmittance and resistance characteristics.
本発明は、π共役系導電性高分子(a)にドープしたポリアニオン(b)と、塩基性有機化合物(c)とのイオン対を、有機溶剤を含む溶媒中に分散してなる導電性組成物に関する。 The present invention relates to a conductive composition obtained by dispersing an ion pair of a polyanion (b) doped in a π-conjugated conductive polymer (a) and a basic organic compound (c) in a solvent containing an organic solvent. Related to things.
更に本発明は、溶媒が、重量比で有機溶剤:水=50:50〜100:0の範囲である上記導電性組成物に関する。 Furthermore, this invention relates to the said electrically conductive composition whose solvent is the range of organic solvent: water = 50: 50-100: 0 by weight ratio.
更に、バインダーポリマー(d)を含有してなる上記導電性組成物に関する。 Furthermore, it is related with the said electroconductive composition formed by containing a binder polymer (d).
更に本発明は、π共役系導電性高分子(a)が、下記一般式(1)、(2)、(3)、(4)、及び(5)からなる群より選ばれた、少なくとも一種以上の繰り返し単位を有する上記導電性組成物に関する。 In the present invention, the π-conjugated conductive polymer (a) is at least one selected from the group consisting of the following general formulas (1), (2), (3), (4), and (5). It is related with the said electrically conductive composition which has the above repeating unit.
一般式(1) General formula (1)
一般式(2) General formula (2)
一般式(3) General formula (3)
一般式(4) General formula (4)
一般式(5) General formula (5)
更に本発明は、ポリアニオン(b)が、スルホン酸基、リン酸基、カルボキシル基、またはそれらと塩基性化合物との塩形成基を有するエチレン性不飽和単量体をラジカル重合してなるホモポリマー、または、これらスルホン酸基、スルホン酸塩基、リン酸基、カルボキシル基またはそれらと塩基性化合物との塩形成基を有するエチレン性不飽和単量体と、他の重合可能なエチレン性不飽和単量体とをラジカル重合してなる共重合体である上記導電性組成物に関する。 Furthermore, the present invention provides a homopolymer obtained by radical polymerization of an ethylenically unsaturated monomer in which the polyanion (b) has a sulfonic acid group, a phosphoric acid group, a carboxyl group, or a salt-forming group of these and a basic compound. Or an ethylenically unsaturated monomer having a sulfonic acid group, a sulfonic acid group, a phosphoric acid group, a carboxyl group, or a salt-forming group of these with a basic compound, and another polymerizable ethylenically unsaturated monomer. The present invention relates to the conductive composition, which is a copolymer obtained by radical polymerization of a monomer.
更に本発明は、π共役系導電性高分子(a)が、ポリ(3,4−エチレンジオキシチオフェン)である上記導電性組成物に関する。 Furthermore, the present invention relates to the above conductive composition, wherein the π-conjugated conductive polymer (a) is poly (3,4-ethylenedioxythiophene).
更に本発明は、ポリアニオン(b)が、ポリスチレンスルホン酸である上記導電性組成物に関する。 Furthermore, this invention relates to the said electroconductive composition whose polyanion (b) is a polystyrene sulfonic acid.
更に本発明は、下記一般式(6)で表される有機化合物、ラクタム基を含む有機化合物、糖、糖誘導体、アルキレングリコール類、アルコールアミン類、ポリエチレングリコール類、グリセリン、チオジグリコール、ジクロロ酢酸、トリフルオロ酢酸、トリフルオロエタノール、及びメタクレゾールからなる群より選ばれる、少なくとも一種以上の添加物(e)を含有してなる上記導電性組成物に関する。 Furthermore, the present invention provides an organic compound represented by the following general formula (6), an organic compound containing a lactam group, a sugar, a sugar derivative, an alkylene glycol, an alcohol amine, a polyethylene glycol, a glycerin, a thiodiglycol, and dichloroacetic acid. In addition, the present invention relates to the above conductive composition containing at least one additive (e) selected from the group consisting of trifluoroacetic acid, trifluoroethanol, and metacresol.
一般式(6) General formula (6)
更に本発明は、添加物(e)が、N−メチルピロリドン、ピロリドン、カプロラクタム、N−メチルカプロラクタム、N−オクチルピロリドン、ショ糖、グルコース、フルクトース、ラクトース、ソルビトール、マンニトール、2−フランカルボン酸、3−フランカルボン酸、エチレングリコール、1,3−プロパンジオール、1,4−ブタンジオール、ジエタノールアミン、トリエタノールアミン、グリセリン、ジ−もしくはトリエチレングリコール、チオジグリコール、ジクロロ酢酸、トリフルオロ酢酸、トリフルオロエタノール、及びメタクレゾールよりなる群から選ばれる上記導電性組成物に関する。 Furthermore, the present invention provides that the additive (e) contains N-methylpyrrolidone, pyrrolidone, caprolactam, N-methylcaprolactam, N-octylpyrrolidone, sucrose, glucose, fructose, lactose, sorbitol, mannitol, 2-furancarboxylic acid, 3-furancarboxylic acid, ethylene glycol, 1,3-propanediol, 1,4-butanediol, diethanolamine, triethanolamine, glycerin, di- or triethylene glycol, thiodiglycol, dichloroacetic acid, trifluoroacetic acid, tri The present invention relates to the conductive composition selected from the group consisting of fluoroethanol and metacresol.
更に本発明は、π共役系導電性高分子(a)にドープしたポリアニオン(b)と、塩基性有機化合物(c)とのイオン対を、有機溶剤を含む溶媒中に分散することを特徴とする上記導電性組成物の製造方法に関する。 Furthermore, the present invention is characterized in that an ion pair of a polyanion (b) doped with a π-conjugated conductive polymer (a) and a basic organic compound (c) is dispersed in a solvent containing an organic solvent. The present invention relates to a method for producing the conductive composition.
本発明により、有機溶剤中でも安定に分散及び乳化された導電性組成物を提供でき、さらに、この組成物から透過度および抵抗特性に非常に優れた透明導電膜を提供することができた。 According to the present invention, a conductive composition that is stably dispersed and emulsified even in an organic solvent can be provided, and a transparent conductive film having excellent transparency and resistance characteristics can be provided from this composition.
本発明に用いるπ共役系導電性高分子(a)は、下記一般式(1)、(2)、(3)、(4)、及び(5)からなる群より選ばれた、少なくとも一種以上の繰り返し単位を有する。 The π-conjugated conductive polymer (a) used in the present invention is at least one selected from the group consisting of the following general formulas (1), (2), (3), (4), and (5). Of repeating units.
一般式(1) General formula (1)
一般式(2) General formula (2)
一般式(3) General formula (3)
一般式(4) General formula (4)
一般式(5) General formula (5)
本発明に用いるπ共役系導電性高分子(a)は、一般式(1)〜(5)の構造を含む単量体を重合してなる。単量体として、好ましくは、3−チオフェンカルボキシアミド、3−チオフェンマロン酸、3−チオフェンメタノール、3−チオフェンエタノール、3,4−エチレンジオキシチオフェン、3−チオフェンアルデヒド、3−ヘキシルチオフェン、3−ブチルチオフェン、3−ドデシルチオフェン、3−ドコシルチオフェン、3−チオフェンカルボン酸、3−チオフェンアセトニトリル、3−チオフェンカルボキシアルデヒド、3−チオフェンアセチルクロライド、3−チオフェンホウ酸、3−チオフェンカルボキシルクロライド、3−チオフェンエタンスルフォネート、3−チオフェンブタンスルフォネート、ピロール、アニリン、アニリン−2,5−ジスルホン酸ナトリウム、アミノベンゼンスルホン酸、オルト−アニシジン、メタ−アニシジン、オルト−アニシジン塩酸塩、メタ−アニシジン塩酸塩、カルバゾール、3−(N−カルバゾイル)プロピン等を使用することができ、これら単量体は、単独でも2種類以上を併用しても使用することができる。 The π-conjugated conductive polymer (a) used in the present invention is formed by polymerizing a monomer having a structure represented by the general formulas (1) to (5). As the monomer, preferably 3-thiophenecarboxamide, 3-thiophenmalonic acid, 3-thiophenemethanol, 3-thiopheneethanol, 3,4-ethylenedioxythiophene, 3-thiophenealdehyde, 3-hexylthiophene, 3 -Butylthiophene, 3-dodecylthiophene, 3-docosylthiophene, 3-thiophenecarboxylic acid, 3-thiopheneacetonitrile, 3-thiophenecarboxaldehyde, 3-thiopheneacetyl chloride, 3-thiopheneboric acid, 3-thiophenecarboxyl chloride, 3-thiopheneethane sulfonate, 3-thiophene butane sulfonate, pyrrole, aniline, sodium aniline-2,5-disulfonate, aminobenzene sulfonic acid, ortho-anisidine, meta-ani Gin, ortho-anisidine hydrochloride, meta-anisidine hydrochloride, carbazole, 3- (N-carbazoyl) propyne, etc. can be used, and these monomers can be used alone or in combination of two or more. be able to.
次に、本発明に用いるポリアニオン(b)を構成する酸基含有単量体としては、例えば、スルホン酸基、リン酸基、カルボキシル基、またはそれらと塩基性化合物との塩形成基などの官能基を含有する単量体であれば、特に限定されないが、スルホン酸基、リン酸基などの強酸基を含有するものが好ましく使用できる。 Next, examples of the acid group-containing monomer constituting the polyanion (b) used in the present invention include functional groups such as a sulfonic acid group, a phosphoric acid group, a carboxyl group, or a salt-forming group of these and a basic compound. Although it will not specifically limit if it is a monomer containing a group, What contains strong acid groups, such as a sulfonic acid group and a phosphoric acid group, can be used preferably.
スルホン酸基を含有する単量体としては、例えば、スチレンスルホン酸、アリルオキシベンゼンスルホン酸、メタリルオキシベンゼンスルホン酸、ビニルスルホン酸、アリルスルホン酸、メタリルスルホン酸、4−スルフォニックアシドブチルメタクリレート、イソプレンスルホン酸、スルホブチルメタクリレート、2−アクリルアミド−2−メチルプロパンスルホン酸、スルホエチルメタクリレートなどが挙げられる。これらの単量体は、単独で、または2種以上を組み合わせて用いることができ、アンモニア、トリエチルアミン、水酸化ナトリウムなどの塩基で中和した塩形成基の状態で使用することもできる。さらに、樹脂を重合した後、硫酸、発煙硫酸、スルファミン酸等のスルホン化剤によりスルホン化することも好ましい。 Examples of the monomer containing a sulfonic acid group include styrene sulfonic acid, allyloxybenzene sulfonic acid, methallyloxybenzene sulfonic acid, vinyl sulfonic acid, allyl sulfonic acid, methallyl sulfonic acid, and 4-sulfonic acid butyl. Examples include methacrylate, isoprene sulfonic acid, sulfobutyl methacrylate, 2-acrylamido-2-methylpropane sulfonic acid, sulfoethyl methacrylate, and the like. These monomers can be used alone or in combination of two or more, and can also be used in the form of a salt-forming group neutralized with a base such as ammonia, triethylamine or sodium hydroxide. Furthermore, after polymerizing the resin, it is also preferable to sulfonate with a sulfonating agent such as sulfuric acid, fuming sulfuric acid, sulfamic acid and the like.
リン酸基を含有する単量体としては、例えば、3−クロロ−2−アシッドホスホキシプロピル(メタ)アクリレート、アシッドホスホキシポリオキシエチレングリコールモノ(メタ)アクリレート、モノ(2−ヒドロキシエチルアクリレート)アシッドホスフェート、モノ(2−ヒドロキシエチルメタクリレート)アシッドホスフェート、モノ(2−ヒドロキシプロピルアクリレート)アシッドホスフェート、モノ(2−ヒドロキシプロピルメタクリレート)アシッドホスフェート、モノ(3−ヒドロキシプロピルアクリレート)アシッドホスフェート、モノ(3−ヒドロキシプロピルメタクリレート)アシッドホスフェート、ジフェニル−2−アクリロイルオキシエチルホスフェート、ジフェニル−2−メタクリロイルオキシエチルホスフェートなどが挙げられる。これらの単量体は、単独で、または2種以上を組み合わせて用いることができ、アンモニア、トリエチルアミン、水酸化ナトリウムなどの塩基で中和した塩形成基の状態で使用することもできる。 Examples of the monomer containing a phosphoric acid group include 3-chloro-2-acid phosphoxypropyl (meth) acrylate, acid phosphooxypolyoxyethylene glycol mono (meth) acrylate, and mono (2-hydroxyethyl acrylate). Acid phosphate, mono (2-hydroxyethyl methacrylate) acid phosphate, mono (2-hydroxypropyl acrylate) acid phosphate, mono (2-hydroxypropyl methacrylate) acid phosphate, mono (3-hydroxypropyl acrylate) acid phosphate, mono (3 -Hydroxypropyl methacrylate) acid phosphate, diphenyl-2-acryloyloxyethyl phosphate, diphenyl-2-methacryloyloxyethyl phosphate Such as over doors and the like. These monomers can be used alone or in combination of two or more, and can also be used in the form of a salt-forming group neutralized with a base such as ammonia, triethylamine or sodium hydroxide.
カルボキシル基を含有する単量体としては、例えば、アクリル酸、メタクリル酸、クロトン酸等のエチレン性不飽和モノカルボン酸;マレイン酸、フマル酸、イタコン酸等のエチレン性不飽和多価カルボン酸およびそれらの酸無水物;マレイン酸メチル、イタコン酸メチル等のエチレン性不飽和多価カルボン酸の部分エステル化物;等を挙げることができる。これらの単量体は、単独で、または2種以上を組み合わせて用いることができ、アンモニア、トリエチルアミン、水酸化ナトリウムなどの塩基で中和した塩形成基の状態で使用することができる。 Examples of the monomer containing a carboxyl group include ethylenically unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; ethylenically unsaturated polyvalent carboxylic acids such as maleic acid, fumaric acid, and itaconic acid; Examples thereof include acid anhydrides thereof; partially esterified products of ethylenically unsaturated polyvalent carboxylic acids such as methyl maleate and methyl itaconate; and the like. These monomers can be used alone or in combination of two or more, and can be used in the form of a salt-forming group neutralized with a base such as ammonia, triethylamine or sodium hydroxide.
酸基含有単量体と共重合可能な他の単量体は、公知の化合物を何等制限なく使用することができる。例えば、1,3−ブタジエン、イソプレン、2−クロロ−1,3−ブタジエン、2−メチル−1,3−ブタジエン等の共役ジエン単量体;スチレン、α−メチルスチレン、p−メチルスチレン等の芳香族ビニル単量体;(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸ブチル、(メタ)アクリル酸2−エチルヘキシル等のエチレン性不飽和カルボン酸アルキルエステル単量体;アクリルアミド、メタクリルアミド、N,N−ジメチルアクリルアミド、N−メチロールアクリルアミド等のエチレン性不飽和カルボン酸アミド単量体;(メタ)アクリル酸ヒドロキシアルキル、グリセリンジ(メタ)アクリレート等のエチレン性不飽和カルボン酸ヒドロキシアルキルエステル単量体;酢酸ビニル等のカルボン酸ビニルエステル単量体;(メタ)アクリロニトリル、N−ビニルピロリドン、(メタ)アクリロイルモルホリン、シクロヘキシルマレイミド、イソプロピルマレイミド、(メタ)アクリル酸グリシジル等が挙げられる。これらは単独で、あるいは2種以上を組み合わせて用いることができる。 As other monomers copolymerizable with the acid group-containing monomer, known compounds can be used without any limitation. For example, conjugated diene monomers such as 1,3-butadiene, isoprene, 2-chloro-1,3-butadiene, 2-methyl-1,3-butadiene; styrene, α-methylstyrene, p-methylstyrene, etc. Aromatic vinyl monomers; ethylenically unsaturated carboxylic acid alkyl ester monomers such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate; Ethylenically unsaturated carboxylic acid amide monomers such as acrylamide, methacrylamide, N, N-dimethylacrylamide, N-methylolacrylamide; ethylenically unsaturated carboxylic acids such as hydroxyalkyl (meth) acrylate and glycerin di (meth) acrylate Acid hydroxyalkyl ester monomer; vinyl carboxylate such as vinyl acetate Ester monomers; (meth) acrylonitrile, N- vinylpyrrolidone, (meth) acryloyl morpholine, cyclohexyl maleimide, isopropyl maleimide, and (meth) glycidyl acrylate. These can be used alone or in combination of two or more.
ポリアニオン(b)は、上記単量体を、開始剤を用いてラジカル重合することで得ることができる。 The polyanion (b) can be obtained by radical polymerization of the above monomer using an initiator.
さらに、本発明に用いるポリアニオン(b)は、エポキシ樹脂の末端エポキシ基の少なくとも一部を、リン含有酸でエステル化することにより生ずる水溶性リン酸エステル化物でもあり得る。 Furthermore, the polyanion (b) used in the present invention may be a water-soluble phosphoric acid ester produced by esterifying at least part of the terminal epoxy group of the epoxy resin with a phosphorus-containing acid.
ポリアニオン(b)の重量平均分子量は、好ましくは1,000〜2,000,000の範囲、より好ましくは2,000〜500,000の範囲内である。 The weight average molecular weight of the polyanion (b) is preferably in the range of 1,000 to 2,000,000, more preferably in the range of 2,000 to 500,000.
更に、本発明による導電性組成物で、極めて高い透過度と導電性が必要とされる場合は、π共役系導電性高分子(a)にポリ(3,4−エチレンジオキシチオフェン)を用い、ポリアニオン(b)にポリスチレンスルホン酸を用いるとより好ましい。 Furthermore, when the conductive composition according to the present invention requires extremely high permeability and conductivity, poly (3,4-ethylenedioxythiophene) is used for the π-conjugated conductive polymer (a). More preferably, polystyrene sulfonic acid is used for the polyanion (b).
本発明で用いるπ共役系導電性高分子(a)は、ポリアニオン(b)水溶液中で酸化剤及び/または酸素もしくは空気を用い、好ましくは水性媒体中で0〜100℃の温度で酸化重合を行うことで得ることができる。 The π-conjugated conductive polymer (a) used in the present invention undergoes oxidative polymerization at a temperature of 0 to 100 ° C. in an aqueous medium, preferably using an oxidizing agent and / or oxygen or air in an aqueous polyanion (b) solution. It can be obtained by doing.
本発明で用いるポリアニオン(b)とπ共役系導電性高分子(a)のモル比(b/a)は、1〜80が好ましく、より好ましくは2〜40である。ポリアニオン(b)とπ共役系導電性高分子(a)のモル比(b/a)が1未満であると、π共役系導電性高分子(a)とポリアニオン(b)とが水に溶解、または分散することができない場合があり、80よりも大きいと導電性の効率が低下する場合がある。 The molar ratio (b / a) between the polyanion (b) and the π-conjugated conductive polymer (a) used in the present invention is preferably 1 to 80, more preferably 2 to 40. When the molar ratio (b / a) between the polyanion (b) and the π-conjugated conductive polymer (a) is less than 1, the π-conjugated conductive polymer (a) and the polyanion (b) are dissolved in water. Or may not be dispersed, and if it is greater than 80, the conductivity efficiency may be reduced.
次に、本発明で用いる塩基性有機化合物(c)について説明する。塩基性有機化合物(c)は、π共役系導電性高分子(a)にドープしたポリアニオン(b)とイオン対になり、有機溶剤中に安定に分散させるために使用する。ここでドープとは、導電性高分子の高分子鎖と電荷移動相互作用等を通じ電子の授受を行ったり、またキャリアの鎖間の移動を助けることができる化合物(ドーパント)を、導電性高分子へしみ込ませたり、あるいは強制的に入れることである。本発明ではπ共役系導電性高分子(a)にドープしたポリアニオン(b)中に残存するアニオン基に、さらに塩基性有機化合物(c)中のカチオン基をイオン対とさせることによって、本来ならば水のみに分散可能な、ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)を溶剤中でも安定に分散させることが可能となった。 Next, the basic organic compound (c) used in the present invention will be described. The basic organic compound (c) forms an ion pair with the polyanion (b) doped in the π-conjugated conductive polymer (a) and is used for stable dispersion in the organic solvent. Here, the term “dope” refers to a compound (dopant) that can transfer electrons between the polymer chain of the conductive polymer and the charge transfer interaction, and can assist the movement between the carrier chains. It is impregnated or forced. In the present invention, the anion group remaining in the polyanion (b) doped in the π-conjugated conductive polymer (a) is further made into an ion pair with the cation group in the basic organic compound (c), so that For example, the π-conjugated conductive polymer (a) doped with the polyanion (b), which can be dispersed only in water, can be stably dispersed even in a solvent.
前記塩基性有機化合物(c)は、公知のアミン化合物(c1)またはカチオン性乳化剤(c2)もしくは塩基性樹脂(c3)などが用いられる。本発明で用いるアミン化合物(c1)としては、例えば、N−メチルオクチルアミン、メチルベンジルアミン、N−メチルアニリン、ジメチルアミン、ジエチルアミン、ジエタノールアミン、N−メチルエタノールアミン、ジ−n−プロピルアミン、ジイソプロピルアミン、メチル−イソプロパノールアミン、ジブチルアミン、ジ−2−エチルヘキシルアミンなどが挙げられる。1級アミンとしては、たとえばアミノエチルエタノールアミン、3−アミノ−1−プロパノール、イソプロピルアミン、モノエチルアミン、2−エチルヘキシルアミン、t−ブチルアミン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリエトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、N−フェニル−3−アミノプロピルトリメトキシシラン等が挙げられる。 As the basic organic compound (c), a known amine compound (c1), a cationic emulsifier (c2), a basic resin (c3), or the like is used. Examples of the amine compound (c1) used in the present invention include N-methyloctylamine, methylbenzylamine, N-methylaniline, dimethylamine, diethylamine, diethanolamine, N-methylethanolamine, di-n-propylamine, and diisopropyl. Examples include amine, methyl-isopropanolamine, dibutylamine, di-2-ethylhexylamine and the like. Examples of the primary amine include aminoethylethanolamine, 3-amino-1-propanol, isopropylamine, monoethylamine, 2-ethylhexylamine, t-butylamine, N- (2-aminoethyl) -3-aminopropylmethyldimethoxy. Silane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxy Silane, N-phenyl-3-aminopropyltrimethoxysilane, etc. are mentioned.
さらに本発明で用いる前記カチオン性乳化剤(c2)としては、例えば、モノメチルアミン、モノエチルアミン、ステアリルアミン等の1級アミンの塩酸塩、ジメチルアミン、ジエチルアミン、ジステアリルアミン等の2級アミンの塩酸塩、トリメチルアミン、トリエチルアミン、ステアリルジメチルアミン等の3級アミンの塩酸塩、ステアリルトリメチルアンモニウムクロリド、ジステアリルジメチルアンモニウムクロリド、ステアリルジメチルベンジルアンモニウムクロリド等の4級アンモニウム塩、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のエタノールアミン類の塩酸塩、エチレンジアミン、ジエチレントリアミン等のポリエチレンポリアミン類の塩酸塩等が挙げられ、単独使用または併用することができる。 Furthermore, examples of the cationic emulsifier (c2) used in the present invention include hydrochlorides of primary amines such as monomethylamine, monoethylamine and stearylamine, and hydrochlorides of secondary amines such as dimethylamine, diethylamine and distearylamine. , Tertiary amine hydrochlorides such as trimethylamine, triethylamine, stearyldimethylamine, quaternary ammonium salts such as stearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, monoethanolamine, diethanolamine, triethanolamine, etc. Ethanolamine hydrochlorides, polyethylenepolyamine hydrochlorides such as ethylenediamine and diethylenetriamine, etc., which can be used alone or in combination. The
アミン化合物(c1)およびカチオン性乳化剤(c2)の使用量に制限はないが、π共役高分子(a)とポリアニオン(b)との合計をベースとして、1〜100,000重量%添加するのが好ましく、10〜10,000重量%の範囲で添加されるのがより好ましい。 Although there is no restriction | limiting in the usage-amount of an amine compound (c1) and a cationic emulsifier (c2), 1-100,000 weight% is added based on the sum total of (pi) conjugated polymer (a) and a polyanion (b). Is preferably added in the range of 10 to 10,000% by weight.
さらに本発明で用いる前記塩基性樹脂(c3)の一例としては、特許文献5〜8に開示されているポリエステル系、アクリル系、ウレタン系の高分子共重合物からなるものであり、重量平均分子量1,000〜1,000,000のものが挙げられる。塩基性樹脂(c3)の重量平均分子量が、1,000未満では十分な立体障害が得られず、分散効果が低下する場合があり、重量平均分子量が1,000,000より大きくても逆に凝集作用が生じる場合がある。また、塩基性樹脂(c3)のアミン価は、5〜200mgKOH/gが好ましい。5mgKOH/g未満では、π共役系導電性高分子(a)にドープしたポリアニオン(b)との相互作用が不十分になりやすく、十分な分散効果が得られない場合もある。一方、塩基性樹脂(c3)のアミン価が200mgKOH/gを越えると、π共役系導電性高分子(a)にドープしたポリアニオン(b)への親和部に比べ、立体障害層が少なくなり、分散効果が不十分になる場合がある。このような塩基性樹脂(c3)としては、例えば、Solsperse17000、Solsperse20000、Solsperse24000、Solsperse32000(ゼネカ株式会社製)、Disperbyk−160、Disperbyk−161、Disperbyk−162、Disperbyk−163、Disperbyk−170、Disperbyk−2000、Disperbyk−2001(ビックケミー社製)、アジスパーPB711、アジスパーPB821、アジスパーPB822、アジスパーPB824(味の素株式会社製)、エポミン006、エポミン012、エポミン018(日本触媒株式会社製)、EFKA4046、EFKA4300、EFKA4330、EFKA4510(EFKA社製)、ディスパロンDA−400N(楠本化成化学社製)、等が挙げられ、単独使用または併用することができる。特に、アジスパーPB821、アジスパーPB822、アジスパーPB824が、分散性や使用時の導電性の点で好ましい。塩基性樹脂(c3)の使用量に制限はないが、π共役系導電性高分子(a)とポリアニオン(b)との合計をベースとして、1〜100,000重量%、好ましくは10〜10,000重量%の範囲で添加されるのが好ましい。
(特許文献5)特開昭60−166318号公報
(特許文献6)特開昭61−174939号公報
(特許文献7)特開昭46−7294号公報
(特許文献8)特開平09−169821号公報
Furthermore, as an example of the basic resin (c3) used in the present invention, it is composed of a polyester-based, acrylic-based, or urethane-based polymer copolymer disclosed in Patent Documents 5 to 8, and has a weight average molecular weight. The thing of 1,000-1,000,000 is mentioned. If the weight average molecular weight of the basic resin (c3) is less than 1,000, sufficient steric hindrance may not be obtained, and the dispersion effect may be reduced. Conversely, even if the weight average molecular weight is greater than 1,000,000, Aggregation may occur. The amine value of the basic resin (c3) is preferably 5 to 200 mgKOH / g. If it is less than 5 mgKOH / g, the interaction with the polyanion (b) doped in the π-conjugated conductive polymer (a) tends to be insufficient, and a sufficient dispersion effect may not be obtained. On the other hand, when the amine value of the basic resin (c3) exceeds 200 mgKOH / g, the steric hindrance layer is reduced as compared with the affinity part for the polyanion (b) doped in the π-conjugated conductive polymer (a). The dispersion effect may be insufficient. Examples of such basic resin (c3) include Solsperse 17000, Solsperse 20000, Solsperse 24000, Solsperse 32000 (manufactured by GENEKA CORPORATION), Disperbyk-160, Disperbyk-161, Disperbyk-162, Disperbyk-163, Disperkk-163, Disperkk-163, Disperk 2000, Disperbyk-2001 (manufactured by Big Chemie), Addisper PB711, Addisper PB821, Addisper PB822, Addisper PB824 (Ajinomoto Co., Inc.), Epomin 006, Epomin 012, Epomin 018 (produced by Nippon Shokubai Co., Ltd.), EFKA4046, EFKA4300, EFKA4300 , EFKA4510 (EFKA Corporation ), DISPARLON DA-400 N (manufactured by Kusumoto Chemicals Chemical Co.), etc., and can be used alone or in combination. In particular, Addisper PB821, Addisper PB822, and Addisper PB824 are preferable in terms of dispersibility and conductivity during use. Although there is no restriction | limiting in the usage-amount of basic resin (c3), 1-100,000 weight% based on the sum total of (pi) conjugated system conductive polymer (a) and a polyanion (b), Preferably it is 10-10. It is preferably added in the range of 1,000% by weight.
(Patent Document 5) JP-A-60-166318 (Patent Document 6) JP-A-61-174939 (Patent Document 7) JP-A-46-7294 (Patent Document 8) JP-A-09-169821 Gazette
さらに、ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)を含む乾燥塗膜に耐溶剤性が必要なときは、光硬化機能を有する塩基性有機化合物が好ましい。光硬化機能を有する塩基性有機化合物を用いる場合は、エチレン性不飽和基を有する塩基性樹脂が好ましく、2つ以上有するものが特に好ましい。エチレン性不飽和基としては(メタ)アクリロイル基、ビニル基、アリル基、ビニルオキシ基、(メタ)アクリロイルフェニル基、ビニルフェニル基、ビニルオキシフェニル基、アリルフェニル基、マレイン酸基、イタコン酸基等が挙げられる。 Further, when the dried coating film containing the π-conjugated conductive polymer (a) doped with the polyanion (b) needs solvent resistance, a basic organic compound having a photocuring function is preferable. When using the basic organic compound which has a photocuring function, the basic resin which has an ethylenically unsaturated group is preferable, and what has 2 or more is especially preferable. Ethylenically unsaturated groups include (meth) acryloyl group, vinyl group, allyl group, vinyloxy group, (meth) acryloylphenyl group, vinylphenyl group, vinyloxyphenyl group, allylphenyl group, maleic acid group, itaconic acid group, etc. Is mentioned.
本発明では、π共役系導電性高分子(a)にドープしたポリアニオン(b)を、有機溶剤を含む溶媒中に分散する際に、塩基性有機化合物(c)は、アミン化合物(c1)、カチオン性乳化剤(c2)、および塩基性樹脂(c3)の中から単独使用または併用することができる。使用量に制限はないが、π共役系導電性高分子(a)とポリアニオン(b)との合計をベースとして、塩基性有機化合物(c)として1〜100,000重量%、好ましくは10〜10,000重量%の範囲で添加されるのが好ましい。 In the present invention, when the polyanion (b) doped in the π-conjugated conductive polymer (a) is dispersed in a solvent containing an organic solvent, the basic organic compound (c) is an amine compound (c1), The cationic emulsifier (c2) and the basic resin (c3) can be used alone or in combination. Although there is no restriction | limiting in the usage-amount, it is 1-100,000 weight% as a basic organic compound (c) based on the sum total of (pi) conjugated system conductive polymer (a) and a polyanion (b), Preferably it is 10- It is preferable to add in the range of 10,000% by weight.
本発明に用いる有機溶剤は、特に限定されるものではなく、アルコール類、ケトン類、エステル類、エーテル類、セロソルブ類、芳香族炭化水素類、脂肪族炭化水素類等種々の液状媒体であり、単独使用または併用することができる。ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)を、有機溶剤を含む溶媒中に分散するためには、水に対する溶解度が有限であり、かつ、乾燥工程のコスト面から沸点が200℃以下であり、環境に対する影響を考慮すると非ハロゲン系の有機溶剤であることが好ましく、例えばシクロヘキサノン、メチルエチルケトン、メチルイソブチルケトン、トルエン、酢酸エチル、酢酸ブチル、キシレン、プロピレングリコールモノメチルエーテルアセテート、イソオクタン等が好ましい。水に対する溶解度が無限である溶剤を用いると、ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)を分散することができず、汎用溶剤に溶解している樹脂や汎用溶剤に分散した顔料溶液に添加した場合ショックが起こり、塗膜にした場合に透過度の低い塗膜となる場合がある。 The organic solvent used in the present invention is not particularly limited, and various liquid media such as alcohols, ketones, esters, ethers, cellosolves, aromatic hydrocarbons, aliphatic hydrocarbons, Can be used alone or in combination. In order to disperse the π-conjugated conductive polymer (a) doped with the polyanion (b) in a solvent containing an organic solvent, the solubility in water is finite, and the boiling point from the cost of the drying step Is less than 200 ° C., and is preferably a non-halogen organic solvent in consideration of the influence on the environment. For example, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, toluene, ethyl acetate, butyl acetate, xylene, propylene glycol monomethyl ether acetate, Isooctane and the like are preferable. If a solvent having infinite solubility in water is used, the π-conjugated conductive polymer (a) doped with the polyanion (b) cannot be dispersed, and the resin or general-purpose solvent dissolved in the general-purpose solvent When added to the dispersed pigment solution, a shock occurs, and when it is formed into a coating film, a coating film with low permeability may be formed.
本発明における有機溶剤と水との混合比率は、重量比で有機溶剤:水=50:50〜100:0の範囲が好ましく、75:25〜100:0がより好ましく、90:10〜100:0が特に好ましい。有機溶剤:水=50:50よりも水が多くなると、汎用溶剤に溶解している樹脂溶液に添加したときに樹脂の保存安定性を低下させる場合や、汎用溶剤に顔料等を分散させている系に添加すると顔料が凝集したりする場合や、組成物を均一に塗工できない場合がある。 The mixing ratio of the organic solvent and water in the present invention is preferably in a range of weight ratio of organic solvent: water = 50: 50 to 100: 0, more preferably 75:25 to 100: 0, and 90:10 to 100: 0 is particularly preferred. When the amount of water is larger than organic solvent: water = 50: 50, when added to a resin solution dissolved in a general-purpose solvent, the storage stability of the resin is lowered, or a pigment or the like is dispersed in the general-purpose solvent. When added to the system, the pigment may aggregate or the composition may not be applied uniformly.
ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)を、塩基性有機化合物(c)を用いて有機溶剤を含む溶媒中に分散する際には、乳化機を使用してもよい。本発明で使用する乳化機は、ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)の平均粒径を10μm以下、好ましくは5μm以下とすることができるものであれば、どの様な機種でもよい。本発明で使用できる乳化機の例としては、超音波ホモジナイザー、ホモミキサー、マイルダー、アトライター、(超)高圧ホモジナイザー及びコロイドミルを挙げることができる。 When the π-conjugated conductive polymer (a) doped with the polyanion (b) is dispersed in a solvent containing an organic solvent using the basic organic compound (c), an emulsifier may be used. Good. The emulsifier used in the present invention may be any one as long as the average particle diameter of the π-conjugated conductive polymer (a) doped with the polyanion (b) can be 10 μm or less, preferably 5 μm or less. Various models may be used. Examples of the emulsifier that can be used in the present invention include an ultrasonic homogenizer, a homomixer, a milder, an attritor, a (ultra) high pressure homogenizer, and a colloid mill.
ここで、本発明でいう平均粒径とは、有機溶剤を含む溶媒中でのポリアニオン(b)によってドープされたπ共役系導電性高分子(a)の粒子径を動的光散乱法で測定した場合の、累積体積平均径で、例えば、MALBERN INSTRUMENTS社製ゼータサイザーNano−ZS粒子径測定装置で測定された値のことを示す。 Here, the average particle diameter referred to in the present invention is the measurement of the particle diameter of the π-conjugated conductive polymer (a) doped with the polyanion (b) in a solvent containing an organic solvent by a dynamic light scattering method. In this case, the cumulative volume average diameter is a value measured with a Zetasizer Nano-ZS particle size measuring device manufactured by MALBERN INSTRUMENTS, for example.
本発明で用いるバインダーポリマー(d)は、溶剤に溶解または分散可能であれば特に限定されるものではない。例えば、石油樹脂、カゼイン、セラック、ロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂、ニトロセルロース、セルロースアセテートブチレート、環化ゴム、塩化ゴム、酸化ゴム、塩酸ゴム、フェノール樹脂、アルキド樹脂、ポリエステル樹脂、不飽和ポリエステル樹脂、アミノ樹脂、エポキシ樹脂、ビニル樹脂、塩化ビニル、塩化ビニル−酢酸ビニル酸性基含有ウレタン樹脂、アクリル樹脂、メタクリル樹脂、ポリウレタン樹脂、シリコーン樹脂、フッ素樹脂、乾性油、合成乾性油、スチレン変性マレイン酸、ポリアミド樹脂、塩素化ポリプロピレン、ブチラール樹脂、塩化ビニリデン樹脂等が挙げられる。 The binder polymer (d) used in the present invention is not particularly limited as long as it can be dissolved or dispersed in a solvent. For example, petroleum resin, casein, shellac, rosin modified maleic resin, rosin modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, phenol resin, alkyd resin, polyester resin, Unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate acidic group-containing urethane resin, acrylic resin, methacrylic resin, polyurethane resin, silicone resin, fluorine resin, drying oil, synthetic drying oil, Examples thereof include styrene-modified maleic acid, polyamide resin, chlorinated polypropylene, butyral resin, and vinylidene chloride resin.
バインダーポリマー(d)として光硬化機能を有する化合物を用いる場合は、エチレン性不飽和基を有する化合物が好ましく、2つ以上有するものが特に好ましい。エチレン性不飽和基としては(メタ)アクリロイル基、ビニル基、アリル基、ビニルオキシ基、(メタ)アクリロイルフェニル基、ビニルフェニル基、ビニルオキシフェニル基、アリルフェニル基、マレイン酸基、イタコン酸基等が挙げられる。バインダーポリマー(d)として光硬化機能を有する化合物を用いる場合は、光重合開始剤を添加することができる。光重合開始剤としては、光励起によってビニル重合を開始できる機能を有するものであれば特に限定はなく、例えばモノカルボニル化合物、ジカルボニル化合物、アセトフェノン化合物、ベンゾインエーテル化合物、アシルフォスフィンオキシド化合物、アミノカルボニル化合物等が使用できる。これらは上記化合物に限定されず、紫外線により重合を開始させる能力があればどのようなものでも構わない。これらは単独使用または併用することができ、使用量に制限はないが、バインダーポリマー(d)の乾燥重量100重量部に対して1〜20重量部の範囲で添加されるのが好ましい。また、増感剤として公知の有機アミンを加えることもできる。 When using the compound which has a photocuring function as a binder polymer (d), the compound which has an ethylenically unsaturated group is preferable, and what has 2 or more is especially preferable. Ethylenically unsaturated groups include (meth) acryloyl group, vinyl group, allyl group, vinyloxy group, (meth) acryloylphenyl group, vinylphenyl group, vinyloxyphenyl group, allylphenyl group, maleic acid group, itaconic acid group, etc. Is mentioned. When a compound having a photocuring function is used as the binder polymer (d), a photopolymerization initiator can be added. The photopolymerization initiator is not particularly limited as long as it has a function capable of initiating vinyl polymerization by photoexcitation. For example, a monocarbonyl compound, a dicarbonyl compound, an acetophenone compound, a benzoin ether compound, an acylphosphine oxide compound, an aminocarbonyl A compound etc. can be used. These are not limited to the above compounds, and any compounds can be used as long as they have the ability to initiate polymerization by ultraviolet rays. These can be used alone or in combination, and the amount used is not limited, but is preferably added in the range of 1 to 20 parts by weight with respect to 100 parts by weight of the dry weight of the binder polymer (d). Moreover, a well-known organic amine can also be added as a sensitizer.
本発明による導電性組成物は、さらに導電性を高めるために、下記一般式(6)で表される有機化合物、ラクタム基を含む有機化合物、糖、糖誘導体、アルキレングリコール類、アルコールアミン類、ポリエチレングリコール類、グリセリン、チオジグリコール、ジクロロ酢酸、トリフルオロ酢酸、トリフルオロエタノール、及びメタクレゾールよりなる群から選ばれる、少なくとも一種以上の添加物(e)を含んでもよい。添加物(e)は、π共役系導電性高分子(a)にドープしたポリアニオン(b)と、塩基性有機化合物(c)とのイオン対を有機溶媒中に分散してなる導電性組成物に対して100重量%以下、好ましくは50重量%以下添加することができる。好ましくは水に可溶性である添加物(e)を用いる。π共役系導電性高分子(a)にドープしたポリアニオン(b)と、塩基性有機化合物のイオン対とを有機溶媒中に分散してなる導電性組成物に対して100重量%を超える添加物(e)を添加すると乾燥工程が長くなることがあり、また配合する樹脂の特性に悪影響を及ぼす場合がある。 In order to further increase the conductivity, the conductive composition according to the present invention includes an organic compound represented by the following general formula (6), an organic compound containing a lactam group, a sugar, a sugar derivative, an alkylene glycol, an alcohol amine, It may contain at least one or more additives (e) selected from the group consisting of polyethylene glycols, glycerin, thiodiglycol, dichloroacetic acid, trifluoroacetic acid, trifluoroethanol, and metacresol. The additive (e) is a conductive composition obtained by dispersing an ion pair of a polyanion (b) doped in a π-conjugated conductive polymer (a) and a basic organic compound (c) in an organic solvent. 100% by weight or less, preferably 50% by weight or less can be added. An additive (e) that is preferably soluble in water is used. Additives exceeding 100% by weight with respect to a conductive composition obtained by dispersing a polyanion (b) doped in a π-conjugated conductive polymer (a) and an ion pair of a basic organic compound in an organic solvent When (e) is added, the drying process may be lengthened, and the properties of the resin to be blended may be adversely affected.
一般式(6) General formula (6)
添加物(e)に対応する殊に好適な有機化合物は、N−メチルピロリドン、ピロリドン、カプロラクタム、N−メチルカプロラクタム、N−オクチルピロリドン、ショ糖、グルコース、フルクトース、ラクトース、ソルビトール、マンニトール、2−フランカルボン酸、3−フランカルボン酸、1,3−プロパンジオール、1,4−ブタンジオール、ジエタノールアミン、トリエタノールアミン、エチレングリコール、グリセリン、ジ−もしくはトリエチレングリコール、チオジグリコール、ジクロロ酢酸、トリフルオロ酢酸、トリフルオロエタノール、及びメタクレゾールよりなる群から選ばれる混合物である。 Particularly suitable organic compounds corresponding to additive (e) are N-methylpyrrolidone, pyrrolidone, caprolactam, N-methylcaprolactam, N-octylpyrrolidone, sucrose, glucose, fructose, lactose, sorbitol, mannitol, 2- Furancarboxylic acid, 3-furancarboxylic acid, 1,3-propanediol, 1,4-butanediol, diethanolamine, triethanolamine, ethylene glycol, glycerin, di- or triethylene glycol, thiodiglycol, dichloroacetic acid, tri It is a mixture selected from the group consisting of fluoroacetic acid, trifluoroethanol, and metacresol.
この他、本発明の溶剤安定性組成物には目的を損なわない範囲で任意成分として、さらに溶剤、染料、酸化防止剤、重合禁止剤、レベリング剤、保湿剤、粘度調整剤、防腐剤、抗菌剤、アンチブロッキング剤、紫外線吸収剤、赤外線吸収剤、電磁波シールド剤、球状フィラー等を添加することができる。 In addition, the solvent-stable composition of the present invention includes, as optional components within a range not to impair the purpose, and further include a solvent, a dye, an antioxidant, a polymerization inhibitor, a leveling agent, a humectant, a viscosity modifier, an antiseptic, and an antibacterial agent. An agent, an anti-blocking agent, an ultraviolet absorber, an infrared absorber, an electromagnetic shielding agent, a spherical filler, etc. can be added.
本発明の導電性組成物に感光性樹脂を含まない場合は、基材に塗工後、自然または強制乾燥によって透明導電膜を得られる。本発明の導電性組成物に感光性樹脂を含む場合は、基材に塗工後、自然または強制乾燥によって後にラジエーション硬化を行っても良いし、塗工に続いてラジエーション硬化させた後に自然または強制乾燥しても構わないが、自然または強制乾燥後にラジエーション硬化した方が好ましい。電子線で硬化させる場合は、水による硬化阻害又は有機溶剤の残留による塗膜の強度低下を防ぐため、自然または強制乾燥後にラジエーション硬化を行うのが好ましい。ラジエーション硬化のタイミングは塗工と同時でも構わないし、塗工後でも構わない。公知のラジエーション硬化方法により硬化させ硬化物とすることができ、活性エネルギー線としては、電子線、紫外線、400〜500nmの可視光を使用することができる。 When a photosensitive resin is not included in the conductive composition of the present invention, a transparent conductive film can be obtained by natural or forced drying after coating on a substrate. When the conductive composition of the present invention contains a photosensitive resin, it may be subjected to radiation curing by natural or forced drying after coating on the base material, or natural or forced after radiation curing following coating. Although forced drying may be carried out, it is preferable to perform radiation curing after natural or forced drying. In the case of curing with an electron beam, it is preferable to perform radiation curing after natural or forced drying in order to prevent curing inhibition by water or reduction of the strength of the coating film due to residual organic solvent. The timing of radiation curing may be simultaneous with coating or after coating. It can be cured by a known radiation curing method to obtain a cured product, and as the active energy ray, an electron beam, ultraviolet rays, or visible light of 400 to 500 nm can be used.
照射する電子線の線源には熱電子放射銃、電界放射銃等が使用できる。また、紫外線および400〜500nmの可視光の線源(光源)には、例えば、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、ガリウムランプ、キセノンランプ、カーボンアークランプ等を使用することができる。具体的には、点光源であること、輝度の安定性から、超高圧水銀ランプ、キセノン水銀ランプが用いられることが多い。照射する活性エネルギー線量は、5〜2000mJの範囲で適時設定できるが、工程上管理しやすい50〜1000mJの範囲であることが好ましい。 A thermionic emission gun, a field emission gun, or the like can be used as the electron beam source to be irradiated. For example, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, a gallium lamp, a xenon lamp, a carbon arc lamp, or the like can be used as a source (light source) of ultraviolet light and visible light of 400 to 500 nm. Specifically, an ultra-high pressure mercury lamp or a xenon mercury lamp is often used because of the point light source and the stability of luminance. The active energy dose to be irradiated can be set in a timely manner within a range of 5 to 2000 mJ, but is preferably within a range of 50 to 1000 mJ that can be easily managed in the process.
また、これら紫外線または電子線と、赤外線、遠赤外線、熱風、高周波加熱等による熱の併用も可能である。 Further, these ultraviolet rays or electron beams can be used in combination with heat by infrared rays, far infrared rays, hot air, high frequency heating or the like.
本発明の導電性組成物は有機または無機基体に塗布し得る。適当な無機基体の例にはガラス、酸化物または酸化性もしくは非酸化性セラミック例えば酸化アルミニウム、窒化ケイ素がある。適当な有機基体の例には純粋な有機重合体、共重合体またはその混合物例えばポリスチレン、ポリカーボネート、ポリアクリレート、ポリエステル例えばポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレート、ポリアミド、ポリイミド、随時ガラス繊維強化されたエポキシ樹脂、セルロース誘導体例えば三酢酸セルロース、ポリオレフィン例えばポリエチレン、ポリプロピレンがある。 The conductive composition of the present invention can be applied to an organic or inorganic substrate. Examples of suitable inorganic substrates are glass, oxides or oxidizable or non-oxidizable ceramics such as aluminum oxide, silicon nitride. Examples of suitable organic substrates are pure organic polymers, copolymers or mixtures thereof such as polystyrene, polycarbonate, polyacrylate, polyesters such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polyamide, polyimide, optionally glass fiber reinforced. And epoxy resins, cellulose derivatives such as cellulose triacetate, polyolefins such as polyethylene and polypropylene.
本発明の導電性組成物は、均一塗膜の形成が可能であり、形成される塗膜は、透過度および抵抗特性が非常に優れており、各種帯電防止剤、電池、防食塗料、EMIシールド、光学用コート剤、化学センサー、表示素子、非線形材料、防食剤、接着剤、繊維、帯電防止塗料、導電性塗料、防食塗料、電着塗料、メッキプライマー、電気防食等の用途に使用することができる。 The conductive composition of the present invention is capable of forming a uniform coating film, and the formed coating film has very excellent permeability and resistance characteristics, and various antistatic agents, batteries, anticorrosion paints, EMI shields. , Optical coating agent, chemical sensor, display element, non-linear material, anticorrosive agent, adhesive, fiber, antistatic paint, conductive paint, anticorrosion paint, electrodeposition paint, plating primer, cathodic protection Can do.
以下に実施例をもって本発明を詳細に説明するが、本発明はこれらに限定されるものではない。なお、%は、特に断らない限り重量ベースである。 The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto. % Is based on weight unless otherwise specified.
実施例における評価方法を下記に示した。本発明の導電性組成物から得られた透明導電膜の表面抵抗値は、基材に導電性組成物と塗工後、乾燥させたあとに透明導電膜表面をデジタル超高抵抗/微少電流計(「R8340A」、株式会社アドバンテスト製)を用いて測定した(Ω)。 The evaluation methods in the examples are shown below. The surface resistance value of the transparent conductive film obtained from the conductive composition of the present invention was determined by applying the conductive composition to the substrate and drying the surface of the transparent conductive film after applying the conductive composition to the substrate. ("R8340A", manufactured by Advantest Corporation) (Ω).
本発明の導電性組成物から得られた透明導電膜の全光線透過率は、基材に導電性組成物と塗工後、乾燥させたあとにヘイズメーター(「NDH2000」、日本電色工業(株)製)を用いて測定した。 The total light transmittance of the transparent conductive film obtained from the conductive composition of the present invention was determined by applying a haze meter (“NDH2000”, Nippon Denshoku Industries Co., Ltd.) Measured using a product manufactured by Co., Ltd.
本発明の導電性組成物から得られた透明導電膜のHAZEは、基材に導電性組成物と塗工後、乾燥させたあとにヘイズメーター(「NDH2000」、日本電色工業(株)製)を用いて測定した。 The HAZE of the transparent conductive film obtained from the conductive composition of the present invention was coated with a conductive composition on a base material and then dried, and then a haze meter (“NDH2000”, manufactured by Nippon Denshoku Industries Co., Ltd.). ).
本発明の導電性組成物中の有機溶剤と水の比率は、有機溶剤をガスクロマトグラフ(「GC−17A」島津製作所社製)を用いて定量することで求めた。 The ratio of the organic solvent to water in the conductive composition of the present invention was determined by quantifying the organic solvent using a gas chromatograph (“GC-17A” manufactured by Shimadzu Corporation).
ポリアニオンの分子量測定はゲル透過クロマトグラフ(GPC:「HLC−8220GPC」東ソー株式会社製)を用いて測定した。 The molecular weight of the polyanion was measured using a gel permeation chromatograph (GPC: “HLC-8220GPC” manufactured by Tosoh Corporation).
評価を行うために使用した基材として、湿潤フィルム厚さ100μmのPETフィルムを用いた。 A PET film having a wet film thickness of 100 μm was used as the substrate used for the evaluation.
(合成例1)<バインダーポリマー(d)の合成>
撹拌機、還流冷却管、ドライエアー導入管、温度計を備えた4口フラスコに、ビフェニルテトラカルボン酸二無水物(三菱化学株式会社製)80.0部、ペンタエリスリトールトリアクリレート(日本化薬株式会社製:KAYARAD PET−30)250.0部、ヒドロキノン0.16部、メチルエチルケトン(MEK)141.2部を仕込み、60℃まで昇温した。次いで触媒として1,8−ジアザビシクロ[5.4.0]−7−ウンデセン(東京化成工業株式会社製)1.65部を加え、90℃で6時間撹拌し、グリシジルメタクリレート(ダウ・ケミカル日本株式会社製)77.3部、メチルエチルケトン(MEK)33.9部を加え、次いで触媒として、ジメチルベンジルアミン2.65部を加え、90℃で8時間撹拌し、室温まで冷却して、多官能(メタ)アクリレート化合物であるバインダーポリマー(d)のメチルエチルケトン(MEK)溶液を得た。得られたバインダーポリマー(d)溶液は、透明な淡黄色であり、固形分は70%であった。得られたバインダーポリマー(d)は、数平均分子量(Mn)870、重量平均分子量(Mw)2,830であった。
(Synthesis Example 1) <Synthesis of Binder Polymer (d)>
In a four-necked flask equipped with a stirrer, reflux condenser, dry air inlet tube and thermometer, 80.0 parts of biphenyltetracarboxylic dianhydride (Mitsubishi Chemical Corporation), pentaerythritol triacrylate (Nippon Kayaku Co., Ltd.) Company: KAYARAD PET-30) 250.0 parts, hydroquinone 0.16 parts, methyl ethyl ketone (MEK) 141.2 parts were charged, and the temperature was raised to 60 ° C. Next, 1.65 parts of 1,8-diazabicyclo [5.4.0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) is added as a catalyst, and the mixture is stirred at 90 ° C. for 6 hours. Glycidyl methacrylate (Dow Chemical Japan Co., Ltd.) 77.3 parts by company) and 33.9 parts of methyl ethyl ketone (MEK) were added. Then, 2.65 parts of dimethylbenzylamine was added as a catalyst, stirred at 90 ° C. for 8 hours, cooled to room temperature, and multifunctional ( A methyl ethyl ketone (MEK) solution of the binder polymer (d), which is a meth) acrylate compound, was obtained. The obtained binder polymer (d) solution was transparent light yellow and had a solid content of 70%. The obtained binder polymer (d) had a number average molecular weight (Mn) 870 and a weight average molecular weight (Mw) 2,830.
(参考例1)
ポリアニオン(b)によってドープされたπ共役系導電性高分子(a)として、ポリスチレンスルホン酸水溶液存在下でポリ(3,4−エチレンジオキシチオフェン)を合成したH.C.Starck社製のBAYTRON P AGを用いた。BAYTRON P AGは、溶媒が水でNVが1.2%であり、mol比でスチレンスルホン酸:3,4−エチレンジオキシチオフェン=2.5:1.0であった。
( Reference Example 1)
As a π-conjugated conductive polymer (a) doped with a polyanion (b), poly (3,4-ethylenedioxythiophene) synthesized in the presence of an aqueous polystyrenesulfonic acid solution was used. C. BAYTRON PAG manufactured by Starck was used. BAYTRON P AG had a solvent of water and an NV of 1.2%, and a molar ratio of styrenesulfonic acid: 3,4-ethylenedioxythiophene = 2.5: 1.0.
トルエン100gにジステアリルジメチルアンモニウムクロライドを10g溶解させた溶液にBAYTRON P AGを100g加えてディスパーを用いて室温で1時間攪拌して、乳化物を得た。 To a solution of 10 g of distearyldimethylammonium chloride dissolved in 100 g of toluene, 100 g of BAYTRON PAG was added and stirred at room temperature for 1 hour using a disper to obtain an emulsion.
上記乳化物を室温で24時間静置したあと、青色で透明のトルエン層を分取し、導電性組成物を得た。組成物中の有機溶剤と水との重量比は、99.7:0.3であった。 得られた導電性組成物を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。さらに相対湿度55%で1時間貯蔵した。 The emulsion was allowed to stand at room temperature for 24 hours, and then a blue and transparent toluene layer was collected to obtain a conductive composition. The weight ratio of the organic solvent to water in the composition was 99.7: 0.3. The obtained conductive composition was coated on a PET film using a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. Furthermore, it was stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。塗工物の物性を測定したところ、以下の結果となった。 As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×106Ω(相対湿度55%);
全光線透過率:88%;
HAZE:0.5
Film surface resistance (R OB ): 1.0 × 10 6 Ω (55% relative humidity);
Total light transmittance: 88%;
HAZE: 0.5
(参考例2)
参考例1で得られた導電性組成物をトルエンで3倍に希釈して導電性組成物を得た。得られた組成物中の有機溶剤と水との重量比は、99.9:0.1であった。 得られた導電性組成物を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。さらに相対湿度55%で1時間貯蔵した。
( Reference Example 2)
The conductive composition obtained in Reference Example 1 was diluted 3 times with toluene to obtain a conductive composition. The weight ratio of the organic solvent to water in the obtained composition was 99.9: 0.1. The obtained conductive composition was coated on a PET film using a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. Furthermore, it was stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×107Ω(相対湿度55%);
全光線透過率:89%;
HAZE:0.4
Film surface resistance (R OB ): 1.0 × 10 7 Ω (relative humidity 55%);
Total light transmittance: 89%;
HAZE: 0.4
(実施例3)
酢酸エチル100gにアジスパーPB−821(味の素ファインテクノ社製)を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。組成物中の有機溶剤と水との重量比は、50.3:49.7であった。
(Example 3)
100 g of BAYTRON PAG was added to a solution obtained by dissolving 16 g of Ajisper PB-821 (manufactured by Ajinomoto Fine Techno Co., Ltd.) in 100 g of ethyl acetate, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition. The weight ratio of the organic solvent to water in the composition was 50.3: 49.7.
得られた導電性組成物2gに、合成例1で得たバインダーポリマー(d)溶液1.4g、光重合開始剤としてイルガキュア907(チバ・スペシャルティー・ケミカルズ社製)とイルガキュア184(チバ・スペシャルティー・ケミカルズ社製)をバインダーポリマー(d)の固形分に対してそれぞれ2.5%添加した。これをエチレングリコールとメチルエチルケトン(MEK)で希釈し、エチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 2 g of the obtained conductive composition, 1.4 g of the binder polymer (d) solution obtained in Synthesis Example 1, Irgacure 907 (manufactured by Ciba Specialty Chemicals) and Irgacure 184 (Ciba Special) as photopolymerization initiators Tea Chemicals) was added at 2.5% to the solid content of the binder polymer (d). This was diluted with ethylene glycol and methyl ethyl ketone (MEK) to prepare 20% ethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):2.0×1010Ω(相対湿度55%);
全光線透過率:89%;
HAZE:0.4
Film surface resistance (R OB ): 2.0 × 10 10 Ω (55% relative humidity);
Total light transmittance: 89%;
HAZE: 0.4
(実施例4)
MIBK100gにアジスパーPB−821を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。組成物中の有機溶剤と水との重量比は、50.3:49.3であった。
Example 4
100 g of BAYTRON PAG was added to a solution obtained by dissolving 16 g of Ajisper PB-821 in 100 g of MIBK, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition. The weight ratio of the organic solvent to water in the composition was 50.3: 49.3.
得られた導電性組成物2gに、合成例1で得たバインダーポリマー(d)溶液1.4g、光重合開始剤としてイルガキュア907とイルガキュア184をバインダーポリマー(d)の固形分に対してそれぞれ2.5%添加した。これをエチレングリコールとメチルエチルケトン(MEK)で希釈し、エチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 To 2 g of the obtained conductive composition, 1.4 g of the binder polymer (d) solution obtained in Synthesis Example 1, and Irgacure 907 and Irgacure 184 as photopolymerization initiators were respectively added to the solid content of the binder polymer (d). .5% added. This was diluted with ethylene glycol and methyl ethyl ketone (MEK) to prepare 20% ethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):5.0×1010Ω(相対湿度55%);
全光線透過率:88%;
HAZE:0.3
Film surface resistance (R OB ): 5.0 × 10 10 Ω (55% relative humidity);
Total light transmittance: 88%;
HAZE: 0.3
(実施例5)
シクロヘキサノン100gにアジスパーPB−821を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。
(Example 5)
100 g of BAYTRON PAG was added to a solution obtained by dissolving 16 g of Azisper PB-821 in 100 g of cyclohexanone, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition.
得られた導電性組成物2gに、バインダーポリマー(d)としてUV硬化性樹脂UV1700B(日本合成株式会社製)を1g加え、エバポレーターで水を除去し、青色で透明な導電性組成物を得た。組成物中の有機溶剤と水との重量比は、99.9:0.1であった。 1 g of UV curable resin UV1700B (manufactured by Nihon Gosei Co., Ltd.) was added as a binder polymer (d) to 2 g of the obtained conductive composition, water was removed with an evaporator, and a blue and transparent conductive composition was obtained. . The weight ratio of the organic solvent to water in the composition was 99.9: 0.1.
エバポレーターで水を除去した導電性組成物に光重合開始剤としてイルガキュア907とイルガキュア184をUV1700Bに対してそれぞれ2.5%添加した。これをエチレングリコールとシクロヘキサノンで希釈し、エチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 Irgacure 907 and Irgacure 184 were added to the conductive composition from which water was removed by an evaporator, as a photopolymerization initiator, 2.5% with respect to UV1700B, respectively. This was diluted with ethylene glycol and cyclohexanone to prepare 20% ethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored for 1 hour at a relative humidity of 55%.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×106Ω(相対湿度55%);
全光線透過率:88%;
HAZE:0.2
Film surface resistance (R OB ): 1.0 × 10 6 Ω (55% relative humidity);
Total light transmittance: 88%;
HAZE: 0.2
(実施例6)
シクロヘキサノン100gにアジスパーPB−821を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。
(Example 6)
100 g of BAYTRON PAG was added to a solution obtained by dissolving 16 g of Azisper PB-821 in 100 g of cyclohexanone, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition.
得られた導電性組成物2gに、合成例1で得たバインダーポリマー(d)溶液1.4g加え、エバポレーターで水を除去し、青色で透明な導電性組成物を得た。組成物中の有機溶剤と水との重量比は、99.9:0.1であった。 1.4 g of the binder polymer (d) solution obtained in Synthesis Example 1 was added to 2 g of the obtained conductive composition, and water was removed with an evaporator to obtain a blue and transparent conductive composition. The weight ratio of the organic solvent to water in the composition was 99.9: 0.1.
エバポレーターで水を除去した導電性組成物に光重合開始剤としてイルガキュア907とイルガキュア184をバインダーポリマー(d)の固形分に対してそれぞれ2.5%添加した。これをエチレングリコールとシクロヘキサノンで希釈し、エチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 Irgacure 907 and Irgacure 184 were added as 2.5% of the solid content of the binder polymer (d) as photopolymerization initiators to the conductive composition from which water was removed by an evaporator. This was diluted with ethylene glycol and cyclohexanone to prepare 20% ethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×106Ω(相対湿度55%);
全光線透過率:88%;
HAZE:0.2
Film surface resistance (R OB ): 1.0 × 10 6 Ω (55% relative humidity);
Total light transmittance: 88%;
HAZE: 0.2
(実施例7)
トルエン100gにジステアリルジメチルアンモニウムクロライドを10g溶解させた溶液にBAYTRON P AGを100g加えてディスパーを用いて室温で1時間攪拌して、乳化物を得た。
(Example 7)
To a solution of 10 g of distearyldimethylammonium chloride dissolved in 100 g of toluene, 100 g of BAYTRON PAG was added and stirred at room temperature for 1 hour using a disper to obtain an emulsion.
エバポレーターを用いて上記乳化物から水を除去し、青色で透明の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、100:0であった。 Water was removed from the emulsion using an evaporator to obtain a blue and transparent conductive composition. The weight ratio of the organic solvent to water in the composition was 100: 0.
上記透明導電性組成物100gにアジスパーPB−821を10g溶解させたあと、合成例1で得たバインダーポリマー(d)溶液140g、光重合開始剤としてイルガキュア907とイルガキュア184をバインダーポリマー(d)の固形分に対してそれぞれ2.5%添加した。これをメチルイソブチルケトン(MIBK)で希釈し、固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 After dissolving 10 g of Azisper PB-821 in 100 g of the above transparent conductive composition, 140 g of the binder polymer (d) solution obtained in Synthesis Example 1, and Irgacure 907 and Irgacure 184 as photopolymerization initiators of the binder polymer (d) 2.5% of each was added to the solid content. This was diluted with methyl isobutyl ketone (MIBK) to prepare a solid content of 20%. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored at 55% relative humidity for 1 hour.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×106Ω(相対湿度55%);
全光線透過率:88%;
HAZE:0.3
Film surface resistance (R OB ): 1.0 × 10 6 Ω (55% relative humidity);
Total light transmittance: 88%;
HAZE: 0.3
(実施例8)
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器にスチレンスルホン酸Na500g、水1000g、過硫酸アンモニウム0.5gを仕込み、この反応容器内の空気を窒素ガスで置換した後、攪拌しながら窒素雰囲気下中で、この反応溶液を80℃で8時間反応させた。反応終了後、水を250g添加して、不揮発分濃度40%で重量平均分子量が25,000のポリスチレンスルホン酸Na水溶液を得た。
(Example 8)
A reactor equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introduction tube was charged with 500 g of sodium styrenesulfonate, 1000 g of water and 0.5 g of ammonium persulfate, and the air in the reaction vessel was replaced with nitrogen gas. The reaction solution was reacted at 80 ° C. for 8 hours in a nitrogen atmosphere with stirring. After completion of the reaction, 250 g of water was added to obtain an aqueous polystyrenesulfonic acid Na solution having a nonvolatile content concentration of 40% and a weight average molecular weight of 25,000.
攪拌機、温度計、冷却装置を備えた反応容器にピロール2.6g、水100gを仕込み、空気雰囲気中で攪拌し、ピロールが水に溶解したことを確認してから、さらに上記ポリスチレンスルホン酸Na溶液50gを加え、この反応溶液を5℃に保ち、10wt%の塩化第二銅水溶液43.5gを2時間滴下してトータルで8時間反応させた。反応終了後、水を68.5g添加して、不揮発分濃度10%、mol比でスチレンスルホン酸:ピロール=2.5:1.0であるポリスチレンスルホン酸にドープされたポリピロール水溶液を得た。 A reaction vessel equipped with a stirrer, a thermometer, and a cooling device was charged with 2.6 g of pyrrole and 100 g of water, stirred in an air atmosphere and confirmed that pyrrole was dissolved in water. 50 g was added, and the reaction solution was kept at 5 ° C., and 43.5 g of 10 wt% cupric chloride aqueous solution was dropped for 2 hours to react for a total of 8 hours. After completion of the reaction, 68.5 g of water was added to obtain an aqueous polypyrrole solution doped with polystyrene sulfonic acid having a nonvolatile content concentration of 10% and a molar ratio of styrene sulfonic acid: pyrrole = 2.5: 1.0.
MEK100gにアジスパーPB−821を16g溶解させた溶液に上記導電性組成物を12g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。組成物中の有機溶剤と水との重量比は、90.3:9.7であった。 12 g of the conductive composition was added to a solution obtained by dissolving 16 g of Azisper PB-821 in 100 g of MEK, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition. The weight ratio of the organic solvent to water in the composition was 90.3: 9.7.
バインダーポリマー(d)としてポリメチルメタクリレート(Aldrich社製:重量平均分子量93,000)1gをMEK3gに溶解し、さらに上記導電性組成物1gを加えた。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥し、相対湿度55%で1時間貯蔵した。 1 g of polymethyl methacrylate (manufactured by Aldrich: weight average molecular weight 93,000) as a binder polymer (d) was dissolved in 3 g of MEK, and 1 g of the conductive composition was further added. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, dried at 100 ° C. for 2 minutes, and stored at 55% relative humidity for 1 hour.
その結果、透明な黒色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent black PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×109Ω(相対湿度55%);
全光線透過率:87%;
HAZE:0.7
Film surface resistance (R OB ): 1.0 × 10 9 Ω (55% relative humidity);
Total light transmittance: 87%;
HAZE: 0.7
(実施例9)
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器にスチレンスルホン酸Na500g、水1000g、過硫酸アンモニウム0.4gを仕込み、この反応容器内の空気を窒素ガスで置換した後、攪拌しながら窒素雰囲気下中で、この反応溶液を80℃で8時間反応させた。反応終了後、水を250g添加して、不揮発分濃度40%で重量平均分子量が3万3000のポリスチレンスルホン酸Na水溶液を得た。
Example 9
A reactor equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introduction tube was charged with 500 g of sodium styrenesulfonate, 1000 g of water, and 0.4 g of ammonium persulfate, and the air in the reactor was replaced with nitrogen gas. The reaction solution was reacted at 80 ° C. for 8 hours in a nitrogen atmosphere with stirring. After completion of the reaction, 250 g of water was added to obtain an aqueous polystyrenesulfonic acid Na solution having a nonvolatile content of 40% and a weight average molecular weight of 33,000.
攪拌機、温度計、冷却装置を備えた反応容器にアニリン塩酸塩5.8g、水100gを仕込み、空気雰囲気中で攪拌し、さらに上記ポリスチレンスルホン酸Na溶液50gを加え、この反応溶液を5℃に保ち、5wt%の過硫酸アンモニウム水溶液44.2gを2時間滴下してトータルで8時間反応させた。反応終了後、水を64g添加して、不揮発分濃度10%、mol比でスチレンスルホン酸:アニリン=2.0:1.0であるポリスチレンスルホン酸にドープされたポリアニリン水溶液を得た。 A reaction vessel equipped with a stirrer, a thermometer and a cooling device was charged with 5.8 g of aniline hydrochloride and 100 g of water, stirred in an air atmosphere, and further added with 50 g of the above polystyrene sulfonate Na solution, and the reaction solution was brought to 5 ° C. Then, 44.2 g of 5 wt% ammonium persulfate aqueous solution was added dropwise for 2 hours and reacted for a total of 8 hours. After completion of the reaction, 64 g of water was added to obtain a polyaniline aqueous solution doped with polystyrene sulfonic acid having a nonvolatile content concentration of 10% and a molar ratio of styrene sulfonic acid: aniline = 2.0: 1.0.
酢酸エチル100gにアジスパーPB−821を16g溶解させた溶液に上記導電性組成物を12g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。組成物中の有機溶剤と水との重量比は、90.3:9.7であった。 12 g of the conductive composition was added to a solution of 16 g of Azisper PB-821 dissolved in 100 g of ethyl acetate, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition. The weight ratio of the organic solvent to water in the composition was 90.3: 9.7.
バインダーポリマー(d)としてポリメチルメタクリレート(Aldrich社製:重量平均分子量93,000)1gを酢酸エチル3gに溶解し、さらに上記導電性組成物1gを加えた。これをメタクレゾールと酢酸エチルで希釈し、メタクレゾールが溶媒中に20%含まれ固形分が15%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥し、相対湿度55%で1時間貯蔵した。 As a binder polymer (d), 1 g of polymethyl methacrylate (manufactured by Aldrich: weight average molecular weight 93,000) was dissolved in 3 g of ethyl acetate, and 1 g of the conductive composition was further added. This was diluted with metacresol and ethyl acetate to prepare 20% metacresol in the solvent and 15% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, dried at 100 ° C. for 2 minutes, and stored at 55% relative humidity for 1 hour.
その結果、透明な緑色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent green PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×108Ω(相対湿度55%);
全光線透過率:87%;
HAZE:0.6
Film surface resistance (R OB ): 1.0 × 10 8 Ω (55% relative humidity);
Total light transmittance: 87%;
HAZE: 0.6
(実施例10)
酢酸エチル56.67gにアジスパーPB−821を9.40g溶解させた溶液にBAYTRON P AGを50.31g加えて、ディスパーを用いて室温で1時間攪拌し、乳化物を得た。ロータリーエバポレーターを用いて、この乳化物から水を取り除いた。必要に応じて適宜酢酸エチルを加えた。最終的に不揮発分15%の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、100:0であった。
(Example 10)
50.31 g of BAYTRON PAG was added to a solution prepared by dissolving 9.40 g of Azisper PB-821 in 56.67 g of ethyl acetate, and stirred at room temperature for 1 hour using a disper to obtain an emulsion. Water was removed from the emulsion using a rotary evaporator. If necessary, ethyl acetate was added appropriately. Finally, a conductive composition having a nonvolatile content of 15% was obtained. The weight ratio of the organic solvent to water in the composition was 100: 0.
この導電性組成物3.33g、合成例1で作製したバインダーポリマー(d)3.57g、エチレングリコール0.70g、酢酸エチル1.80g、光重合開始剤としてイルガキュア184の20%酢酸エチル溶液を0.75g配合し、不揮発分30%の導電性組成物を得た。この組成物をバーコーター#10を用いてPETフィルム上に塗布し、100℃のオーブンで2分間乾燥した。これにメタルハライドランプを用いて、400mJ/cm2の紫外線を照射して導電膜を作製した。この導電膜について表面抵抗、ヘイズ、全光線透過率を測定した。 3.33 g of this conductive composition, 3.57 g of binder polymer (d) prepared in Synthesis Example 1, 0.70 g of ethylene glycol, 1.80 g of ethyl acetate, and 20% ethyl acetate solution of Irgacure 184 as a photopolymerization initiator A conductive composition having a nonvolatile content of 30% was obtained by blending 0.75 g. This composition was applied onto a PET film using a bar coater # 10 and dried in an oven at 100 ° C. for 2 minutes. A metal halide lamp was used for this to irradiate with 400 mJ / cm 2 of ultraviolet rays to produce a conductive film. The conductive film was measured for surface resistance, haze, and total light transmittance.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):3.5×107Ω(相対湿度55%);
全光線透過率:87.9%;
HAZE:0.9
Film surface resistance (R OB ): 3.5 × 10 7 Ω (55% relative humidity);
Total light transmittance: 87.9%;
HAZE: 0.9
(実施例11)
酢酸エチル56.67gにアジスパーPB−822を9.40g溶解させた溶液にBAYTRON P AGを50.31g加えて、ディスパーを用いて室温で1時間攪拌し、乳化物を得た。ロータリーエバポレーターを用いて、この乳化物から水の一部を取り除いた。必要に応じて適宜酢酸エチルを加えた。最終的に不揮発分15%の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、76:24であった。
(Example 11)
50.31 g of BAYTRON PAG was added to a solution prepared by dissolving 9.40 g of Azisper PB-822 in 56.67 g of ethyl acetate, and stirred at room temperature for 1 hour using a disper to obtain an emulsion. A portion of water was removed from the emulsion using a rotary evaporator. If necessary, ethyl acetate was added appropriately. Finally, a conductive composition having a nonvolatile content of 15% was obtained. The weight ratio of the organic solvent to water in the composition was 76:24.
この導電性組成物3.33g、合成例1で作製したバインダーポリマー(d)3.57g、エチレングリコール0.70g、酢酸エチル1.80g、光重合開始剤としてイルガキュア184の20%酢酸エチル溶液を0.75g配合し、不揮発分30%の導電性組成物を得た。この組成物をバーコーター#10を用いてPETフィルム上に塗布し、100℃のオーブンで2分間乾燥した。これにメタルハライドランプを用いて、400mJ/cm2の紫外線を照射して導電膜を作製した。この導電膜について表面抵抗、ヘイズ、全光線透過率を測定した。 3.33 g of this conductive composition, 3.57 g of binder polymer (d) prepared in Synthesis Example 1, 0.70 g of ethylene glycol, 1.80 g of ethyl acetate, and 20% ethyl acetate solution of Irgacure 184 as a photopolymerization initiator A conductive composition having a nonvolatile content of 30% was obtained by blending 0.75 g. This composition was applied onto a PET film using a bar coater # 10 and dried in an oven at 100 ° C. for 2 minutes. A metal halide lamp was used for this to irradiate with 400 mJ / cm 2 of ultraviolet rays to produce a conductive film. The conductive film was measured for surface resistance, haze, and total light transmittance.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):3.5×109Ω(相対湿度55%);
全光線透過率:86.9%;
HAZE:0.9
Film surface resistance (R OB ): 3.5 × 10 9 Ω (55% relative humidity);
Total light transmittance: 86.9%;
HAZE: 0.9
(実施例12)
酢酸エチル56.67gにアジスパーPB−824を9.40g溶解させた溶液にBAYTRON P AGを50.31g加えて、ディスパーを用いて室温で1時間攪拌し、乳化物を得た。ロータリーエバポレーターを用いて、この乳化物から水の一部を取り除いた。必要に応じて適宜酢酸エチルを加えた。最終的に不揮発分15%の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、95:5であった。
(Example 12)
50.31 g of BAYTRON PAG was added to a solution prepared by dissolving 9.40 g of Azisper PB-824 in 56.67 g of ethyl acetate, and stirred at room temperature for 1 hour using a disper to obtain an emulsion. A portion of water was removed from the emulsion using a rotary evaporator. If necessary, ethyl acetate was added appropriately. Finally, a conductive composition having a nonvolatile content of 15% was obtained. The weight ratio of the organic solvent to water in the composition was 95: 5.
この導電性組成物3.33g、合成例1で作製したバインダーポリマー(d)3.57g、エチレングリコール0.70g、酢酸エチル1.80g、光重合開始剤としてイルガキュア184の20%酢酸エチル溶液を0.75g配合し、不揮発分30%の導電性組成物を得た。この組成物をバーコーター#10を用いてPETフィルム上に塗布し、100℃のオーブンで2分間乾燥した。これにメタルハライドランプを用いて、400mJ/cm2の紫外線を照射して導電膜を作製した。この導電膜について表面抵抗、ヘイズ、全光線透過率を測定した。 3.33 g of this conductive composition, 3.57 g of binder polymer (d) prepared in Synthesis Example 1, 0.70 g of ethylene glycol, 1.80 g of ethyl acetate, and 20% ethyl acetate solution of Irgacure 184 as a photopolymerization initiator A conductive composition having a nonvolatile content of 30% was obtained by blending 0.75 g. This composition was applied onto a PET film using a bar coater # 10 and dried in an oven at 100 ° C. for 2 minutes. A metal halide lamp was used for this to irradiate with 400 mJ / cm 2 of ultraviolet rays to produce a conductive film. The conductive film was measured for surface resistance, haze, and total light transmittance.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.5×107Ω(相対湿度55%);
全光線透過率:87.9%;
HAZE:0.7
Film surface resistance (R OB ): 1.5 × 10 7 Ω (relative humidity 55%);
Total light transmittance: 87.9%;
HAZE: 0.7
(合成例2)<塩基性有機化合物(c)の合成>
撹拌機、還流冷却管、ガス導入管、温度計を備えた4口フラスコに、12−ヒドロキシステアリン酸(伊藤製油株式会社製)12.16g、カプロラクトン(ダイセル化学株式会社製:プラクセルM)87.72g、テトラブチルチタネート(松本製薬工業株式会社製:オルガチックスTA−25)0.088gを仕込み、窒素ガスを吹き込みながら160℃に昇温し、5時間反応させた。その後、100℃まで冷却し、ポリアリルアミンの20%水溶液30.00g加え、昇温して、反応液中の水を取り除いた。120℃まで昇温し、2時間反応させた。次いで、シクロヘキサノン105.97gを加え、塩基性樹脂(c3)のシクロヘキサノン溶液を得た。固形分50%、数平均分子量(Mn)1,564、重量平均分子量(Mw)6,609、アミン価8.907mgKOH/gであった。
(Synthesis Example 2) <Synthesis of Basic Organic Compound (c)>
In a 4-neck flask equipped with a stirrer, a reflux condenser, a gas inlet tube, and a thermometer, 12.16 g of 12-hydroxystearic acid (manufactured by Ito Oil Co., Ltd.), caprolactone (manufactured by Daicel Chemical Industries, Ltd .: Plaxel M) 87. 72 g and 0.088 g of tetrabutyl titanate (manufactured by Matsumoto Pharmaceutical Co., Ltd .: Orgatics TA-25) were charged, the temperature was raised to 160 ° C. while blowing nitrogen gas, and the reaction was allowed to proceed for 5 hours. Then, it cooled to 100 degreeC, 30.00g of 20% aqueous solution of polyallylamine was added, and it heated up, and removed the water in a reaction liquid. The temperature was raised to 120 ° C. and reacted for 2 hours. Next, 105.97 g of cyclohexanone was added to obtain a cyclohexanone solution of the basic resin (c3). The solid content was 50%, the number average molecular weight (Mn) was 1,564, the weight average molecular weight (Mw) was 6,609, and the amine value was 8.907 mgKOH / g.
(合成例3)<塩基性有機化合物(c)の合成>
撹拌機、還流冷却管、ガス導入管、温度計を備えた4口フラスコに、12−ヒドロキシステアリン酸(伊藤製油株式会社製)12.17g、カプロラクトン(ダイセル化学株式会社製:プラクセルM)87.79g、テトラブチルチタネート(松本製薬工業株式会社製:オルガチックスTA−25)0.088gを仕込み、窒素ガスを吹き込みながら160℃に昇温し、5時間反応させた。その後、100℃まで冷却し、ポリアリルアミンの20%水溶液60.55g加え、昇温して、反応液中の水を取り除いた。140℃まで昇温し、2時間反応させた。次いで、シクロヘキサノン112.06gを加え、塩基性樹脂(c3)のシクロヘキサノン溶液を得た。固形分50%、数平均分子量(Mn)1,538、重量平均分子量(Mw)5,556、アミン価11.045mgKOH/gであった。
(Synthesis Example 3) <Synthesis of Basic Organic Compound (c)>
In a 4-neck flask equipped with a stirrer, reflux condenser, gas inlet tube, and thermometer, 12.17 g of 12-hydroxystearic acid (manufactured by Ito Oil Co., Ltd.), caprolactone (manufactured by Daicel Chemical Industries, Ltd .: Plaxel M) 87. 79 g of tetrabutyl titanate (manufactured by Matsumoto Pharmaceutical Co., Ltd .: ORGATICS TA-25) 0.088 g was charged, the temperature was raised to 160 ° C. while blowing nitrogen gas, and the mixture was reacted for 5 hours. Then, it cooled to 100 degreeC, 60.55g of 20% aqueous solution of polyallylamine was added, and it heated up, and removed the water in a reaction liquid. The temperature was raised to 140 ° C. and reacted for 2 hours. Next, 112.06 g of cyclohexanone was added to obtain a cyclohexanone solution of the basic resin (c3). The solid content was 50%, the number average molecular weight (Mn) was 1,538, the weight average molecular weight (Mw) was 5,556, and the amine value was 11.055 KOH / g.
(実施例13)
シクロヘキサノン47.27gに合成例2で得られた塩基性樹脂溶液を18.80g溶解させた溶液にBAYTRON P AGを50.31g加えて、ディスパーを用いて室温で1時間攪拌し、乳化物を得た。ロータリーエバポレーターを用いて、この乳化物から水を取り除いた。必要に応じて適宜酢酸エチルを加えた。最終的に不揮発分15%の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、100:0であった。
(Example 13)
Add 50.31 g of BAYTRON PAG to a solution obtained by dissolving 18.80 g of the basic resin solution obtained in Synthesis Example 2 in 47.27 g of cyclohexanone, and stir at room temperature for 1 hour using a disper to obtain an emulsion. It was. Water was removed from the emulsion using a rotary evaporator. If necessary, ethyl acetate was added appropriately. Finally, a conductive composition having a nonvolatile content of 15% was obtained. The weight ratio of the organic solvent to water in the composition was 100: 0.
この導電性組成物3.33g、合成例1で作製したバインダーポリマー(d)3.57g、エチレングリコール0.70g、酢酸エチル1.80g、光重合開始剤としてイルガキュア184の20%酢酸エチル溶液を0.75g配合し、不揮発分30%の導電性組成物を得た。この組成物をバーコーター#10を用いてPETフィルム上に塗布し、100℃のオーブンで2分間乾燥した。これにメタルハライドランプを用いて、400mJ/cm2の紫外線を照射して導電膜を作製した。この導電膜について表面抵抗、ヘイズ、全光線透過率を測定した。 3.33 g of this conductive composition, 3.57 g of binder polymer (d) prepared in Synthesis Example 1, 0.70 g of ethylene glycol, 1.80 g of ethyl acetate, and 20% ethyl acetate solution of Irgacure 184 as a photopolymerization initiator A conductive composition having a nonvolatile content of 30% was obtained by blending 0.75 g. This composition was applied onto a PET film using a bar coater # 10 and dried in an oven at 100 ° C. for 2 minutes. A metal halide lamp was used for this to irradiate with 400 mJ / cm 2 of ultraviolet rays to produce a conductive film. The conductive film was measured for surface resistance, haze, and total light transmittance.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):2.1×107Ω(相対湿度55%);
全光線透過率:87.9%;
HAZE:0.7
Film surface resistance (R OB ): 2.1 × 10 7 Ω (relative humidity 55%);
Total light transmittance: 87.9%;
HAZE: 0.7
(実施例14)
シクロヘキサノン47.27gに合成例3で得られた塩基性樹脂溶液を18.80g溶解させた溶液にBAYTRON P AGを50.31g加えて、ディスパーを用いて室温で1時間攪拌し、乳化物を得た。ロータリーエバポレーターを用いて、この乳化物から水を取り除いた。必要に応じて適宜酢酸エチルを加えた。最終的に不揮発分15%の導電性組成物を得た。組成物中の有機溶剤と水との重量比は、100:0であった。
(Example 14)
Add 50.31 g of BAYTRON P AG to a solution obtained by dissolving 18.80 g of the basic resin solution obtained in Synthesis Example 3 in 47.27 g of cyclohexanone, and stir at room temperature for 1 hour using a disper to obtain an emulsion. It was. Water was removed from the emulsion using a rotary evaporator. If necessary, ethyl acetate was added appropriately. Finally, a conductive composition having a nonvolatile content of 15% was obtained. The weight ratio of the organic solvent to water in the composition was 100: 0.
この導電性組成物3.33g、合成例1で作製したバインダーポリマー(d)3.57g、エチレングリコール0.70g、酢酸エチル1.80g、光重合開始剤としてイルガキュア184の20%酢酸エチル溶液を0.75g配合し、不揮発分30%の導電性組成物を得た。この組成物をバーコーター#10を用いてPETフィルム上に塗布し、100℃のオーブンで2分間乾燥した。これにメタルハライドランプを用いて、400mJ/cm2の紫外線を照射して導電膜を作製した。この導電膜について表面抵抗、ヘイズ、全光線透過率を測定した。 3.33 g of this conductive composition, 3.57 g of binder polymer (d) prepared in Synthesis Example 1, 0.70 g of ethylene glycol, 1.80 g of ethyl acetate, and 20% ethyl acetate solution of Irgacure 184 as a photopolymerization initiator A conductive composition having a nonvolatile content of 30% was obtained by blending 0.75 g. This composition was applied onto a PET film using a bar coater # 10 and dried in an oven at 100 ° C. for 2 minutes. A metal halide lamp was used for this to irradiate with 400 mJ / cm 2 of ultraviolet rays to produce a conductive film. The conductive film was measured for surface resistance, haze, and total light transmittance.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):2.0×107Ω(相対湿度55%);
全光線透過率:87.7%;
HAZE:0.9
Film surface resistance (R OB ): 2.0 × 10 7 Ω (55% relative humidity);
Total light transmittance: 87.7%;
HAZE: 0.9
(実施例15)
シクロヘキサノン100gにアジスパーPB−822を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。
(Example 15)
100 g of BAYTRON PAG was added to a solution of 16 g of Azisper PB-822 dissolved in 100 g of cyclohexanone, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition.
得られた導電性組成物2gに、バインダーポリマー(d)としてUV硬化性樹脂DA−721(ナガセケムテックス株式会社製)を1g加え、エバポレーターで水を除去し、青色で透明な導電性組成物を得た。組成物中の有機溶剤と水との重量比は、99.9:0.1であった。 1 g of UV curable resin DA-721 (manufactured by Nagase ChemteX Corporation) is added as a binder polymer (d) to 2 g of the obtained conductive composition, water is removed by an evaporator, and the blue transparent conductive composition Got. The weight ratio of the organic solvent to water in the composition was 99.9: 0.1.
エバポレーターで水を除去した導電性組成物に光重合開始剤としてイルガキュア907とイルガキュア184をDA−721に対してそれぞれ2.5%添加した。これをジエチレングリコールとシクロヘキサノンで希釈し、ジエチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 Irgacure 907 and Irgacure 184 were added to the conductive composition from which water was removed by an evaporator, respectively, as photopolymerization initiators with respect to DA-721. This was diluted with diethylene glycol and cyclohexanone to prepare 20% diethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored for 1 hour at a relative humidity of 55%.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.8×108Ω(相対湿度55%);
全光線透過率:87%;
HAZE:0.7
Film surface resistance (R OB ): 1.8 × 10 8 Ω (55% relative humidity);
Total light transmittance: 87%;
HAZE: 0.7
(実施例16)
シクロヘキサノン100gにアジスパーPB−822を16g溶解させた溶液にBAYTRON P AGを100g加えて、ディスパーを用いて室温で1時間攪拌して、導電性組成物を得た。
(Example 16)
100 g of BAYTRON PAG was added to a solution of 16 g of Azisper PB-822 dissolved in 100 g of cyclohexanone, and stirred at room temperature for 1 hour using a disper to obtain a conductive composition.
得られた導電性組成物2gに、バインダーポリマー(d)としてUV硬化性樹脂DA−911M(ナガセケムテックス株式会社製)を1g加え、エバポレーターで水を除去し、青色で透明な導電性組成物を得た。組成物中の有機溶剤と水との重量比は、99.9:0.1であった。 1 g of UV curable resin DA-911M (manufactured by Nagase ChemteX Corporation) is added as a binder polymer (d) to 2 g of the obtained conductive composition, water is removed with an evaporator, and the blue transparent conductive composition Got. The weight ratio of the organic solvent to water in the composition was 99.9: 0.1.
エバポレーターで水を除去した導電性組成物に光重合開始剤としてイルガキュア907とイルガキュア184をDA−911Mに対してそれぞれ2.5%添加した。これをチオジグリコールとシクロヘキサノンで希釈し、チオジグリコールが溶媒中に5%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。 Irgacure 907 and Irgacure 184 as photopolymerization initiators were added to the conductive composition from which water was removed by an evaporator, respectively, at 2.5% with respect to DA-911M. This was diluted with thiodiglycol and cyclohexanone so that 5% of thiodiglycol was contained in the solvent and the solid content was 20%. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored for 1 hour at a relative humidity of 55%.
その結果、透明な淡青色のPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent light blue PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):3.0×107Ω(相対湿度55%);
全光線透過率:87%;
HAZE:0.7
Film surface resistance (R OB ): 3.0 × 10 7 Ω (55% relative humidity);
Total light transmittance: 87%;
HAZE: 0.7
(比較例1)
BAYTRON P AGのみを乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥し、相対湿度55%で1時間貯蔵した。
(Comparative Example 1)
Only BAYTRON P AG was applied to a PET film so that the dry film thickness was 5 μm, dried at 100 ° C. for 2 minutes, and stored for 1 hour at 55% relative humidity.
その結果、表面の光沢がない淡青色のPRTフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a light blue PRT film coated product having no surface gloss was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.0×106Ω(相対湿度55%);
全光線透過率:74%;
HAZE:43.4
Film surface resistance (R OB ): 1.0 × 10 6 Ω (55% relative humidity);
Total light transmittance: 74%;
HAZE: 43.4
(比較例2)
BAYTRON P AG2gに合成例1で得たバインダーポリマー(d)溶液1.4g添加すると青色の凝集物が発生し、均一に塗工できなかった。
(Comparative Example 2)
When 1.4 g of the binder polymer (d) solution obtained in Synthesis Example 1 was added to 2 g of BAYTRON P AG, a blue agglomerate was generated and coating could not be performed uniformly.
(比較例3)
基材として湿潤フィルム厚さ100μmのPETフィルムについて、参考例1と同様に物性を測定したところ、以下の結果となった。
(Comparative Example 3)
When the physical properties of a PET film having a wet film thickness of 100 μm as a substrate were measured in the same manner as in Reference Example 1, the following results were obtained.
PETフィルムの表面抵抗(ROB):1.0×1015Ω(相対湿度55%);
全光線透過率:89%;
HAZE:0.3
Surface resistance (R OB ) of PET film: 1.0 × 10 15 Ω (relative humidity 55%);
Total light transmittance: 89%;
HAZE: 0.3
(比較例4)
合成例1で得たバインダーポリマー(d)溶液1.4gに光重合開始剤としてイルガキュア907とイルガキュア184をバインダーポリマー(d)の固形分に対してそれぞれ2.5%添加した。これをエチレングリコールとシクロヘキサノンで希釈し、エチレングリコールが溶媒中に20%含まれ固形分が20%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥した。これにメタルハライドランプで400mJ/cm2の紫外線を照射し、塗工物を作製し、相対湿度55%で1時間貯蔵した。
(Comparative Example 4)
Irgacure 907 and Irgacure 184 as photopolymerization initiators were added to 1.4 g of the binder polymer (d) solution obtained in Synthesis Example 1 at 2.5% based on the solid content of the binder polymer (d). This was diluted with ethylene glycol and cyclohexanone to prepare 20% ethylene glycol in the solvent and 20% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, and dried at 100 ° C. for 2 minutes. This was irradiated with ultraviolet rays of 400 mJ / cm 2 with a metal halide lamp to prepare a coated product, and stored at 55% relative humidity for 1 hour.
その結果、透明なPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):2.0×1014Ω(相対湿度55%);
全光線透過率:89%;
HAZE:0.2
Film surface resistance (R OB ): 2.0 × 10 14 Ω (relative humidity 55%);
Total light transmittance: 89%;
HAZE: 0.2
(比較例5)
バインダーポリマー(d)としてポリメチルメタクリレート(Aldrich社製:重量平均分子量93,000)1gを酢酸エチル3gに溶解した。これをメタクレゾールと酢酸エチルで希釈し、メタクレゾールが溶媒中に20%含まれ固形分が15%になるよう調製した。この溶液を、バーコーターを用いて、乾燥膜厚が5μmになるようPETフィルムに塗工し、100℃で2分乾燥し、相対湿度55%で1時間貯蔵した。
(Comparative Example 5)
As the binder polymer (d), 1 g of polymethyl methacrylate (manufactured by Aldrich: weight average molecular weight 93,000) was dissolved in 3 g of ethyl acetate. This was diluted with metacresol and ethyl acetate to prepare 20% metacresol in the solvent and 15% solid content. This solution was applied to a PET film with a bar coater so that the dry film thickness was 5 μm, dried at 100 ° C. for 2 minutes, and stored at 55% relative humidity for 1 hour.
その結果、透明なPETフィルム塗工物が得られた。参考例1と同様に塗工物の物性を測定したところ、以下の結果となった。
As a result, a transparent PET film coated product was obtained. When the physical properties of the coated product were measured in the same manner as in Reference Example 1, the following results were obtained.
フィルムの表面抵抗(ROB):1.5×1014Ω(相対湿度55%);
全光線透過率:89%;
HAZE:0.4
Film surface resistance (R OB ): 1.5 × 10 14 Ω (55% relative humidity);
Total light transmittance: 89%;
HAZE: 0.4
実施例3〜16の導電性組成物は、表面抵抗の低い導電性の塗膜を得ることができ、かつ、ヘイズの低い透明性に優れた塗膜を得ることができた。一方、比較例1〜5の組成物は、導電性と透明性の両立ができなかった。
The conductive compositions of Examples 3 to 16 were able to obtain a conductive coating film having a low surface resistance and a coating film having excellent transparency with low haze. On the other hand, the compositions of Comparative Examples 1 to 5 could not achieve both conductivity and transparency.
Claims (8)
The conductive composition according to any one of claims 1 to 4, wherein the solvent has a weight ratio of organic solvent: water = 50: 50 to 100: 0.
一般式(6)
General formula (6)
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