JP6071688B2 - Antistatic release agent composition and antistatic release film - Google Patents
Antistatic release agent composition and antistatic release film Download PDFInfo
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- JP6071688B2 JP6071688B2 JP2013064858A JP2013064858A JP6071688B2 JP 6071688 B2 JP6071688 B2 JP 6071688B2 JP 2013064858 A JP2013064858 A JP 2013064858A JP 2013064858 A JP2013064858 A JP 2013064858A JP 6071688 B2 JP6071688 B2 JP 6071688B2
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- release agent
- poly
- pedot
- antistatic
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- 239000003795 chemical substances by application Substances 0.000 claims description 84
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- CUXKZYSCZCNPNX-UHFFFAOYSA-N tetradecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCC[NH3+] CUXKZYSCZCNPNX-UHFFFAOYSA-N 0.000 description 1
- SMEFTBPJZGVAPK-UHFFFAOYSA-M tetradodecylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC SMEFTBPJZGVAPK-UHFFFAOYSA-M 0.000 description 1
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- MPKQTNAUFAZSIJ-UHFFFAOYSA-N thiophene-3,4-diol Chemical compound OC1=CSC=C1O MPKQTNAUFAZSIJ-UHFFFAOYSA-N 0.000 description 1
- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SBHRWOBHKASWGU-UHFFFAOYSA-M tridodecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- RNPOWDKBFLNPNV-UHFFFAOYSA-M trihexyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCC[N+](C)(CCCCCC)CCCCCC RNPOWDKBFLNPNV-UHFFFAOYSA-M 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
本発明は、帯電防止性剥離剤用の組成物及び剥離フィルムに関する。 The present invention relates to a composition for an antistatic release agent and a release film.
剥離フィルムとして、プラスチックフィルムや紙等の基材の表面にシリコーン系剥離剤が塗布されたものが広く利用されている。
ところで、基材は帯電し易く、シリコーン系剥離剤を塗布すると、さらに帯電し易くなる傾向にあった。そのため、剥離フィルムに対して帯電防止性の付与が求められていた。
従来、帯電防止剤としては、界面活性剤等のイオン導電性化合物が広く使用されていたが、イオン導電性化合物は、導電性に湿度依存性を有するため、帯電防止性が安定せず、また、ブリードアウトするという問題を有していた。そこで、剥離フィルムに対して帯電防止性を付与するための帯電防止剤として、導電性に湿度依存性やブリードアウトのないπ共役系導電性高分子を使用することがあった。
π共役系導電性高分子は不溶不融の物質であり、塗布や押出ラミネートを適用できないため、通常、ポリアニオンをドーパント兼界面活性剤として用いて水分散液にされている（特許文献１）。
As a release film, a film obtained by applying a silicone release agent to the surface of a substrate such as a plastic film or paper is widely used.
By the way, the base material is easily charged, and when a silicone release agent is applied, it tends to be more easily charged. Therefore, it has been required to impart antistatic properties to the release film.
Conventionally, ionic conductive compounds such as surfactants have been widely used as antistatic agents. However, ionic conductive compounds have humidity dependence on conductivity, and thus antistatic properties are not stable. Had the problem of bleeding out. Thus, as an antistatic agent for imparting antistatic properties to the release film, a π-conjugated conductive polymer that does not depend on humidity or bleed out is sometimes used.
Since a π-conjugated conductive polymer is an insoluble and infusible substance and cannot be applied or coated by extrusion, it is usually made into an aqueous dispersion using a polyanion as a dopant and a surfactant (Patent Document 1).
ところで、近年、ディスプレイにおいては精細性がより高くなり、部品実装分野においては実装速度のより一層の向上が求められている。そのため、光学用途に使用される保護フィルムや、電子電気部品用に使用される帯電防止性剥離フィルムのニーズが高まっている。
これらのニーズに対し、付加硬化型シリコーンエマルジョンとチオフェン系導電性高分子を含む剥離剤を用いた剥離フィルムが提案されている（特許文献２）。
しかし、エマルジョン型シリコーンは基材に対する密着性が低い上に、大量の水を含有し、塗工機の腐食を起こす懸念があり、帯電防止性剥離フィルムの用途に適用しにくかった。
By the way, in recent years, the definition has become higher in the display, and further improvement in the mounting speed has been demanded in the component mounting field. Therefore, there is an increasing need for protective films used for optical applications and antistatic release films used for electronic and electrical parts.
In response to these needs, a release film using a release agent containing an addition-curable silicone emulsion and a thiophene-based conductive polymer has been proposed (Patent Document 2).
However, the emulsion type silicone has low adhesion to the substrate and contains a large amount of water, which may cause corrosion of the coating machine, and is difficult to apply to the application of an antistatic release film.
また、帯電防止性剥離フィルムとして、基材の上に、金属ナノ粒子やπ共役系導電性高分子を含む帯電防止層を設け、該帯電防止層の上に、シリコーン樹脂を含む剥離剤層を設けたものも知られている。
しかし、この場合には、帯電防止層と剥離剤層とを別々に設けるため、塗工回数が複数回となり、高コストになりやすく、また、金属ナノ粒子を用いた場合には帯電防止層のヘイズが高くなるため、光学用途には適していなかった。
In addition, as an antistatic release film, an antistatic layer containing metal nanoparticles and a π-conjugated conductive polymer is provided on a substrate, and a release agent layer containing a silicone resin is provided on the antistatic layer. The ones provided are also known.
However, in this case, since the antistatic layer and the release agent layer are separately provided, the number of times of coating is multiple times, which tends to be expensive, and when metal nanoparticles are used, the antistatic layer Since the haze increases, it is not suitable for optical applications.
一般に、シリコーンは親水性が低いため、π共役系導電性高分子及びポリアニオンの複合体の水分散液とは可溶化しにくい。そこで、水分散液の代わりに非水系の導電性高分子分散液を用いることが考えられた。
非水系の導電性高分子分散液としては、特許文献３には、ポリアニリンの有機溶媒溶液が開示されている。特許文献４〜６には、π共役系導電性高分子及びポリアニオンを含む水分散液の水を有機溶媒に置換して得た有機溶媒分散液が開示されている。特許文献７には、π共役系導電性高分子及びポリアニオンを含む水分散液を凍結乾燥した後、有機溶媒に溶解して得た有機溶媒分散液が開示されている。
Generally, since silicone has low hydrophilicity, it is difficult to solubilize with an aqueous dispersion of a complex of a π-conjugated conductive polymer and a polyanion. Therefore, it has been considered to use a non-aqueous conductive polymer dispersion instead of the aqueous dispersion.
As a non-aqueous conductive polymer dispersion, Patent Document 3 discloses an organic solvent solution of polyaniline. Patent Documents 4 to 6 disclose organic solvent dispersions obtained by substituting water in an aqueous dispersion containing a π-conjugated conductive polymer and a polyanion with an organic solvent. Patent Document 7 discloses an organic solvent dispersion obtained by freeze-drying an aqueous dispersion containing a π-conjugated conductive polymer and a polyanion and then dissolving the organic dispersion in an organic solvent.
しかし、特許文献３に記載の有機溶媒溶液にシリコーン系剥離剤を混ぜて得たものは、溶媒の選択によっては可溶化しているが、乾燥の際に、シリコーン系剥離剤と、π共役系導電性高分子及びポリアニオンの複合体とが分離して、所望の帯電防止性及び剥離性は得られなかった。
特許文献４〜７に記載の有機溶媒分散液にシリコーン系剥離剤を単に混ぜた場合には、シリコーン系剥離剤と、π共役系導電性高分子及びポリアニオンの複合体とが可溶せず、所望の帯電防止性及び剥離性を得ることは困難であった。また、一般に、シリコーンの硬化反応としてヒドロシリル化反応が利用されるが、特許文献４〜７に記載の有機溶媒分散液にシリコーン系剥離剤を混ぜ、加熱してもシリコーンが硬化せず、剥離剤層が形成されないという問題を生じることがあった。
本発明は、帯電防止性と剥離性とが共に優れた帯電防止性剥離剤用組成物及び帯電防止性剥離フィルムを提供することを目的とする。
However, what was obtained by mixing the silicone-based release agent in the organic solvent solution described in Patent Document 3 is solubilized depending on the choice of the solvent, but upon drying, the silicone-type release agent and the π-conjugated system The conductive polymer and the polyanion complex were separated, and the desired antistatic property and peelability were not obtained.
When a silicone release agent is simply mixed in the organic solvent dispersion described in Patent Documents 4 to 7, the silicone release agent and the complex of π-conjugated conductive polymer and polyanion are not soluble, It was difficult to obtain desired antistatic properties and peelability. In general, a hydrosilylation reaction is used as a curing reaction for silicone. However, a silicone release agent is mixed with an organic solvent dispersion described in Patent Documents 4 to 7, and the silicone does not cure even when heated. There was a problem that a layer was not formed.
An object of this invention is to provide the composition for antistatic release agents and the antistatic release film which were excellent in both antistatic property and peelability.
本発明の帯電防止性剥離剤用組成物は、紫外線硬化型オルガノポリシロキサンと光重合開始剤を含む剥離性成分と、ポリエチレンジオキシチオフェン及びポリスチレンスルホン酸の複合体を含む導電性成分と、有機溶媒とを含有し、導電性成分の含有量が、剥離性成分１００質量部に対して０．７〜１３．３質量部であり、前記ポリスチレンスルホン酸の一部のアニオン基に、２級アミン、３級アミン、４級アンモニウム塩からなる群から選択される１種以上のアミン系化合物がイオン対として配位または結合しており、前記アミン系化合物は、炭素数４以上のアルキル基、アリール基、アラルキル基、アルキレン基、アリーレン基、アラルキレン基及びオキシアルキレン基よりなる群から選ばれる置換基を１つ以上有する。
本発明の帯電防止性剥離フィルムは、プラスチックフィルムまたは紙からなる基材と、該基材の少なくとも片面に形成された剥離剤層とを備え、前記剥離剤層が、上記帯電防止性剥離剤用組成物より形成されている。
The composition for an antistatic release agent of the present invention comprises a release component containing an ultraviolet curable organopolysiloxane and a photopolymerization initiator, a conductive component containing a composite of polyethylene dioxythiophene and polystyrene sulfonate, and an organic A solvent, and a content of the conductive component is 0.7 to 13.3 parts by mass with respect to 100 parts by mass of the peelable component, and a secondary amine is added to some anionic groups of the polystyrene sulfonic acid. One or more amine compounds selected from the group consisting of tertiary amines and quaternary ammonium salts are coordinated or bonded as ion pairs, and the amine compounds are alkyl groups having 4 or more carbon atoms, aryl It has one or more substituents selected from the group consisting of a group, an aralkyl group, an alkylene group, an arylene group, an aralkylene group and an oxyalkylene group.
The antistatic release film of the present invention comprises a base material made of a plastic film or paper, and a release agent layer formed on at least one side of the base material, and the release agent layer is used for the antistatic release agent. It is formed from the composition.
本発明の帯電防止性剥離剤用組成物及び帯電防止性剥離フィルムは、帯電防止性と剥離性とが共に優れている。 The antistatic release agent composition and antistatic release film of the present invention are excellent in both antistatic properties and peelability.
＜帯電防止性剥離剤用組成物＞
（剥離性成分）
剥離性成分は、紫外線硬化型オルガノポリシロキサンと光重合開始剤とを含有する。
紫外線硬化型オルガノポリシロキサンとしては、分子中に下記式（１）で示される（メタ）アクリル基を２つ以上有する（メタ）アクリル基含有オルガノポリシロキサンが挙げられる。
下記式（１）中、Ｒ１は２価の連結基であればどのような構造の連結基でもよく、例えば、アルキレン基やアリーレン基などの炭化水素基が挙げられるが、炭素原子と硫黄原子、酸素原子、窒素原子などの異原子を含む連結基であってもよい。式（１）におけるＲ２は、水素原子またはメチル基である。
<Antistatic release agent composition>
(Peelable component)
The peelable component contains an ultraviolet curable organopolysiloxane and a photopolymerization initiator.
Examples of the ultraviolet curable organopolysiloxane include (meth) acryl group-containing organopolysiloxane having two or more (meth) acryl groups represented by the following formula (1) in the molecule.
In the following formula (1), R 1 may be a linking group having any structure as long as it is a divalent linking group, and examples thereof include hydrocarbon groups such as alkylene groups and arylene groups. , A linking group containing a different atom such as an oxygen atom or a nitrogen atom. R 2 in Formula (1) is a hydrogen atom or a methyl group.
紫外線硬化型オルガノポリシロキサンは、具体的には、下記式（２）で示される構造の（メタ）アクリル基含有オルガノポリシロキサン等が挙げられる。
下記式（２）のＲ３は、水素原子またはメチル基、エチル基、プロピル基、ブチル基などの炭素数１〜４のアルキル基もしくはフェニル基である。Ｒ４は、少なくとも１つが式（１）で示される基であり、残りは前記Ｒ３と同様である。ａ、ｂ、ｄは各々０より大きく且つ５００未満の数であり、ｃは１〜１０の数である。ａ，ｂ，ｃ，ｄの各々が前記上限値を超えると、紫外線硬化型オルガノポリシロキサンの合成が困難となる。
Specific examples of the ultraviolet curable organopolysiloxane include (meth) acryl group-containing organopolysiloxane having a structure represented by the following formula (2).
R 3 in the following formula (2) is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group, or a butyl group, or a phenyl group. R 4 is at least one group represented by the formula (1), and the rest are the same as R 3 described above. a, b, and d are each greater than 0 and less than 500, and c is a number from 1 to 10. When each of a, b, c, and d exceeds the upper limit, synthesis of the ultraviolet curable organopolysiloxane becomes difficult.
式（２）において、式（１）で示される基の含有量は１〜４０モル％の範囲とすることが好ましい。前記範囲内で式（１）の含有量を変化させれば、硬化皮膜である剥離剤層の粘着剤に対する剥離力を任意に調整することができる。
式（１）で示される基が１モル％未満であると、紫外線による硬化性が著しく低下することがあり、４０モル％より多くなると、紫外線による硬化性は向上するものの、硬化皮膜の粘着剤に対する剥離力が著しく低下することがある。
In Formula (2), it is preferable to make content of group shown by Formula (1) into the range of 1-40 mol%. If content of Formula (1) is changed within the said range, the peeling force with respect to the adhesive of the release agent layer which is a cured film can be adjusted arbitrarily.
When the group represented by the formula (1) is less than 1 mol%, the curability by ultraviolet rays may be remarkably lowered, and when it exceeds 40 mol%, the curability by ultraviolet rays is improved, but the cured film pressure-sensitive adhesive The peel strength against may decrease significantly.
上記（メタ）アクリロキシ基含有オルガノポリシロキサンは、１種を単独で使用してもよいし、重合度または（メタ）アクリロキシ基含有率が互いに異なる複数の（メタ）アクリロキシ基含有オルガノポリシロキサンを使用してもよい。 The above (meth) acryloxy group-containing organopolysiloxane may be used alone, or a plurality of (meth) acryloxy group-containing organopolysiloxanes having different degrees of polymerization or (meth) acryloxy group content are used. May be.
光重合開始剤は、（メタ）アクリル基含有オルガノポリシロキサンに相溶するものであれば特に制限はなく、具体的には、アセトフェノン、ベンゾフェノン、４−クロロベンゾフェノン、４，４−ジメトキシベンゾフェノン、４−メチルアセトフェノン、ベンゾインメチルエーテル、ベンゾイントリアルキルシリルエーテル等が挙げられる。
光重合開始剤の含有量は、紫外線硬化型オルガノポリシロキサン１００質量部に対して０．１〜２０質量部であることが好ましく、１〜５質量部であることがより好ましい。光重合開始剤の含有量が前記下限値以上であれば、紫外線硬化型オルガノポリシロキサンを充分に硬化させることができる。しかし、前記上限値を超えると、光重合開始剤が硬化後のシリコーン表面にブリードアウトして剥離特性に悪影響を与えることがある。
The photopolymerization initiator is not particularly limited as long as it is compatible with the (meth) acryl group-containing organopolysiloxane. Specifically, acetophenone, benzophenone, 4-chlorobenzophenone, 4,4-dimethoxybenzophenone, 4 -Methylacetophenone, benzoin methyl ether, benzoin trialkylsilyl ether and the like.
The content of the photopolymerization initiator is preferably 0.1 to 20 parts by mass and more preferably 1 to 5 parts by mass with respect to 100 parts by mass of the ultraviolet curable organopolysiloxane. If content of a photoinitiator is more than the said lower limit, an ultraviolet curable organopolysiloxane can fully be hardened. However, when the upper limit is exceeded, the photopolymerization initiator may bleed out on the cured silicone surface and adversely affect the peeling characteristics.
剥離性成分には、ジエチルアミン、２−ジエチルアミンエタノール、ピペリジン等の酸素硬化阻害抑制剤が含まれてもよい。 The peelable component may contain an oxygen curing inhibition inhibitor such as diethylamine, 2-diethylamineethanol, piperidine and the like.
（導電性成分）
本発明の帯電防止性剥離剤用組成物に含まれる導電性成分は、π共役系導電性高分子及びポリアニオンの複合体を含む。前記複合体は、具体的には、π共役系導電性高分子にポリアニオンの一部のアニオン基が配位してドープして、π共役系導電性高分子とポリアニオンとが複合化されている。
導電性成分は、必要に応じて、前記複合体以外の他の導電性物質やイオン導電性化合物を含んでもよい。
(Conductive component)
The conductive component contained in the antistatic release agent composition of the present invention includes a complex of a π-conjugated conductive polymer and a polyanion. Specifically, in the complex, a part of an anion group of a polyanion is coordinated and doped to a π-conjugated conductive polymer, and the π-conjugated conductive polymer and the polyanion are combined. .
The conductive component may include other conductive substances or ion conductive compounds other than the composite as necessary.
導電性成分の含有量は、剥離性成分１００質量部に対して０．３〜３００質量部であり、０．３〜６５質量部であることがより好ましい。導電性成分の含有量が前記下限値以上であることにより、帯電防止性を充分に確保でき、前記上限値以下であることにより、剥離性を充分に確保できる。 Content of an electroconductive component is 0.3-300 mass parts with respect to 100 mass parts of peelable components, and it is more preferable that it is 0.3-65 mass parts. When the content of the conductive component is equal to or higher than the lower limit value, the antistatic property can be sufficiently secured, and when it is equal to or lower than the upper limit value, the peelability can be sufficiently secured.
［π共役系導電性高分子］
π共役系導電性高分子は、主鎖がπ共役系で構成されている有機高分子であり、例えば、ポリピロール類、ポリチオフェン類、ポリアセチレン類、ポリフェニレン類、ポリフェニレンビニレン類、ポリアニリン類、ポリアセン類、ポリチオフェンビニレン類、及びこれらの共重合体等が挙げられる。なかでも、重合の容易さ、空気中での安定性の点からは、ポリチオフェン類、ポリピロール類及びポリアニリン類が好ましい。さらに、溶剤に対する可溶性及び透明性の点から、ポリチオフェン類が好ましい。
[Π-conjugated conductive polymer]
The π-conjugated conductive polymer is an organic polymer whose main chain is composed of a π-conjugated system, for example, polypyrroles, polythiophenes, polyacetylenes, polyphenylenes, polyphenylene vinylenes, polyanilines, polyacenes, Examples thereof include polythiophene vinylenes and copolymers thereof. Of these, polythiophenes, polypyrroles and polyanilines are preferred from the viewpoint of ease of polymerization and stability in air. Furthermore, polythiophenes are preferable from the viewpoint of solubility in solvents and transparency.
ポリチオフェン類としては、ポリチオフェン、ポリ（３−メチルチオフェン）、ポリ（３−エチルチオフェン）、ポリ（３−プロピルチオフェン）、ポリ（３−ブチルチオフェン）、ポリ（３−ヘキシルチオフェン）、ポリ（３−ヘプチルチオフェン）、ポリ（３−オクチルチオフェン）、ポリ（３−デシルチオフェン）、ポリ（３−ドデシルチオフェン）、ポリ（３−オクタデシルチオフェン）、ポリ（３−ブロモチオフェン）、ポリ（３−クロロチオフェン）、ポリ（３−ヨードチオフェン）、ポリ（３−シアノチオフェン）、ポリ（３−フェニルチオフェン）、ポリ（３，４−ジメチルチオフェン）、ポリ（３，４−ジブチルチオフェン）、ポリ（３−ヒドロキシチオフェン）、ポリ（３−メトキシチオフェン）、ポリ（３−エトキシチオフェン）、ポリ（３−ブトキシチオフェン）、ポリ（３−ヘキシルオキシチオフェン）、ポリ（３−ヘプチルオキシチオフェン）、ポリ（３−オクチルオキシチオフェン）、ポリ（３−デシルオキシチオフェン）、ポリ（３−ドデシルオキシチオフェン）、ポリ（３−オクタデシルオキシチオフェン）、ポリ（３，４−ジヒドロキシチオフェン）、ポリ（３，４−ジメトキシチオフェン）、ポリ（３，４−ジエトキシチオフェン）、ポリ（３，４−ジプロポキシチオフェン）、ポリ（３，４−ジブトキシチオフェン）、ポリ（３，４−ジヘキシルオキシチオフェン）、ポリ（３，４−ジヘプチルオキシチオフェン）、ポリ（３，４−ジオクチルオキシチオフェン）、ポリ（３，４−ジデシルオキシチオフェン）、ポリ（３，４−ジドデシルオキシチオフェン）、ポリ（３，４−エチレンジオキシチオフェン）、ポリ（３，４−プロピレンジオキシチオフェン）、ポリ（３，４−ブテンジオキシチオフェン）、ポリ（３−メチル−４−メトキシチオフェン）、ポリ（３−メチル−４−エトキシチオフェン）、ポリ（３−カルボキシチオフェン）、ポリ（３−メチル−４−カルボキシチオフェン）、ポリ（３−メチル−４−カルボキシエチルチオフェン）、ポリ（３−メチル−４−カルボキシブチルチオフェン）が挙げられる。
ポリピロール類としては、ポリピロール、ポリ（Ｎ−メチルピロール）、ポリ（３−メチルピロール）、ポリ（３−エチルピロール）、ポリ（３−ｎ−プロピルピロール）、ポリ（３−ブチルピロール）、ポリ（３−オクチルピロール）、ポリ（３−デシルピロール）、ポリ（３−ドデシルピロール）、ポリ（３，４−ジメチルピロール）、ポリ（３，４−ジブチルピロール）、ポリ（３−カルボキシピロール）、ポリ（３−メチル−４−カルボキシピロール）、ポリ（３−メチル−４−カルボキシエチルピロール）、ポリ（３−メチル−４−カルボキシブチルピロール）、ポリ（３−ヒドロキシピロール）、ポリ（３−メトキシピロール）、ポリ（３−エトキシピロール）、ポリ（３−ブトキシピロール）、ポリ（３−ヘキシルオキシピロール）、ポリ（３−メチル−４−ヘキシルオキシピロール）、ポリ（３−メチル−４−ヘキシルオキシピロール）が挙げられる。
ポリアニリン類としては、ポリアニリン、ポリ（２−メチルアニリン）、ポリ（３−イソブチルアニリン）、ポリ（２−アニリンスルホン酸）、ポリ（３−アニリンスルホン酸）が挙げられる。
上記π共役系導電性高分子の中でも、導電性、透明性、耐熱性の点から、ポリ（３，４−エチレンジオキシチオフェン）が好ましい。
Polythiophenes include polythiophene, poly (3-methylthiophene), poly (3-ethylthiophene), poly (3-propylthiophene), poly (3-butylthiophene), poly (3-hexylthiophene), poly (3 -Heptylthiophene), poly (3-octylthiophene), poly (3-decylthiophene), poly (3-dodecylthiophene), poly (3-octadecylthiophene), poly (3-bromothiophene), poly (3-chloro Thiophene), poly (3-iodothiophene), poly (3-cyanothiophene), poly (3-phenylthiophene), poly (3,4-dimethylthiophene), poly (3,4-dibutylthiophene), poly (3 -Hydroxythiophene), poly (3-methoxythiophene), poly (3-ethoxy Offene), poly (3-butoxythiophene), poly (3-hexyloxythiophene), poly (3-heptyloxythiophene), poly (3-octyloxythiophene), poly (3-decyloxythiophene), poly (3 -Dodecyloxythiophene), poly (3-octadecyloxythiophene), poly (3,4-dihydroxythiophene), poly (3,4-dimethoxythiophene), poly (3,4-diethoxythiophene), poly (3 4-dipropoxythiophene), poly (3,4-dibutoxythiophene), poly (3,4-dihexyloxythiophene), poly (3,4-diheptyloxythiophene), poly (3,4-dioctyloxythiophene) ), Poly (3,4-didecyloxythiophene), poly (3,4-didodeci) Oxythiophene), poly (3,4-ethylenedioxythiophene), poly (3,4-propylenedioxythiophene), poly (3,4-butenedioxythiophene), poly (3-methyl-4-methoxythiophene) ), Poly (3-methyl-4-ethoxythiophene), poly (3-carboxythiophene), poly (3-methyl-4-carboxythiophene), poly (3-methyl-4-carboxyethylthiophene), poly (3 -Methyl-4-carboxybutylthiophene).
Examples of polypyrroles include polypyrrole, poly (N-methylpyrrole), poly (3-methylpyrrole), poly (3-ethylpyrrole), poly (3-n-propylpyrrole), poly (3-butylpyrrole), poly (3-octylpyrrole), poly (3-decylpyrrole), poly (3-dodecylpyrrole), poly (3,4-dimethylpyrrole), poly (3,4-dibutylpyrrole), poly (3-carboxypyrrole) , Poly (3-methyl-4-carboxypyrrole), poly (3-methyl-4-carboxyethylpyrrole), poly (3-methyl-4-carboxybutylpyrrole), poly (3-hydroxypyrrole), poly (3 -Methoxypyrrole), poly (3-ethoxypyrrole), poly (3-butoxypyrrole), poly (3-hexyloxypyrrole) Le), poly (3-methyl-4-hexyloxy-pyrrole), poly (3-methyl-4-hexyloxy-pyrrole) and the like.
Examples of polyanilines include polyaniline, poly (2-methylaniline), poly (3-isobutylaniline), poly (2-aniline sulfonic acid), and poly (3-aniline sulfonic acid).
Among the π-conjugated conductive polymers, poly (3,4-ethylenedioxythiophene) is preferable from the viewpoint of conductivity, transparency, and heat resistance.
［ポリアニオン］
ポリアニオンとは、アニオン基を有する構成単位を有する重合体である。このポリアニオンのアニオン基は、π共役系導電性高分子に対するドーパントとして機能して、π共役系導電性高分子の導電性を向上させる。
ポリアニオンの具体例としては、ポリスチレンスルホン酸、ポリビニルスルホン酸、ポリアリルスルホン酸、ポリアクリルスルホン酸、ポリメタクリルスルホン酸、ポリ（２−アクリルアミド−２−メチルプロパンスルホン酸）、ポリイソプレンスルホン酸、ポリスルホエチルメタクリレート、ポリ（４−スルホブチルメタクリレート）、ポリメタリルオキシベンゼンスルホン酸、ポリビニルカルボン酸、ポリスチレンカルボン酸、ポリアリルカルボン酸、ポリアクリルカルボン酸、ポリメタクリルカルボン酸、ポリ（２−アクリルアミド−２−メチルプロパンカルボン酸）、ポリイソプレンカルボン酸、ポリアクリル酸等が挙げられる。これらの単独重合体であってもよいし、２種以上の共重合体であってもよいが最も好ましいポリアニオンはスルホン酸基含有ポリアニオンである。
[Polyanion]
A polyanion is a polymer having a structural unit having an anion group. The anion group of the polyanion functions as a dopant for the π-conjugated conductive polymer and improves the conductivity of the π-conjugated conductive polymer.
Specific examples of polyanions include polystyrene sulfonic acid, polyvinyl sulfonic acid, polyallyl sulfonic acid, polyacryl sulfonic acid, polymethacryl sulfonic acid, poly (2-acrylamido-2-methylpropane sulfonic acid), polyisoprene sulfonic acid, poly Sulfoethyl methacrylate, poly (4-sulfobutyl methacrylate), polymethallyloxybenzene sulfonic acid, polyvinyl carboxylic acid, polystyrene carboxylic acid, polyallyl carboxylic acid, polyacryl carboxylic acid, polymethacryl carboxylic acid, poly (2-acrylamide- 2-methylpropanecarboxylic acid), polyisoprenecarboxylic acid, polyacrylic acid and the like. These homopolymers may be used, or two or more copolymers may be used, but the most preferred polyanion is a sulfonic acid group-containing polyanion.
ポリアニオンの重合度は、モノマー単位が１０〜１００，０００個の範囲であることが好ましく、分散性及び導電性の点からは、５０〜１０，０００個の範囲がより好ましい。
ポリアニオンの質量平均分子量は２万〜１００万であることが好ましい。ポリアニオンの質量平均分子量が前記下限値以上であれば、π共役系導電性高分子の含有が均一な剥離剤用組成物とすることができ、前記上限値以下であれば、充分に高い導電性を得ることができる。
本発明においては、ポリアニオンに対しては、オルガノポリシロキサンとの可溶性を高くすることが求められ、その可溶性を勘案してポリアニオンの重合度、分子量を選択する必要があるが、それによって本来の導電性や安定性が損なわれてはならない。これらを勘案すると、ポリアニオンの質量平均分子量は２万〜７５万の範囲がより好ましい。
The degree of polymerization of the polyanion is preferably in the range of 10 to 100,000 monomer units, and more preferably in the range of 50 to 10,000 from the viewpoint of dispersibility and conductivity.
The mass average molecular weight of the polyanion is preferably 20,000 to 1,000,000. If the mass average molecular weight of the polyanion is equal to or higher than the lower limit, a composition for a release agent having a uniform π-conjugated conductive polymer content can be obtained. If the polyanion is equal to or lower than the upper limit, the conductivity is sufficiently high. Can be obtained.
In the present invention, the polyanion is required to have high solubility with the organopolysiloxane, and it is necessary to select the polymerization degree and molecular weight of the polyanion in consideration of the solubility. Property and stability must not be impaired. Considering these, the mass average molecular weight of the polyanion is more preferably in the range of 20,000 to 750,000.
ポリアニオンの含有量は、π共役系導電性高分子１モルに対して０．１〜１０モルの範囲であることが好ましく、１〜７モルの範囲であることがより好ましい。ポリアニオンの含有量が前記下限値より少なくなると、π共役系導電性高分子へのドーピング効果が弱くなる傾向にあり、導電性が不足することがある。その上、分散性および溶解性が低くなり、均一な溶液を得ることが困難になる。また、ポリアニオンの含有量が前記上限値より多くなると、π共役系導電性高分子の含有量が少なくなり、やはり充分な導電性が得られにくい。 The content of the polyanion is preferably in the range of 0.1 to 10 mol, and more preferably in the range of 1 to 7 mol, with respect to 1 mol of the π-conjugated conductive polymer. When the polyanion content is less than the lower limit, the doping effect on the π-conjugated conductive polymer tends to be weakened, and the conductivity may be insufficient. In addition, dispersibility and solubility are lowered, making it difficult to obtain a uniform solution. On the other hand, when the polyanion content exceeds the upper limit, the content of the π-conjugated conductive polymer decreases, and it is difficult to obtain sufficient conductivity.
ポリアニオンにおいては、全てのアニオン基がπ共役系導電性高分子にドープせず、余剰のアニオン基を有している。この余剰のアニオン基は親水基であるから、複合体の水分散性を向上させる役割を果たす。 In the polyanion, all the anion groups are not doped into the π-conjugated conductive polymer and have an excess anion group. Since this surplus anion group is a hydrophilic group, it plays a role in improving the water dispersibility of the composite.
本発明では、ポリアニオンの一部のアニオン基、具体的には、π共役系導電性高分子にドープしない余剰のアニオン基に、２級アミン、３級アミン、４級アンモニウム塩からなる群から選択される１種以上のアミン系化合物がイオン対として配位または結合している。余剰のアニオン基にアミン系化合物がイオン対として配位または結合することにより、親水性は低下し、疎水性が向上するため、複合体の有機溶媒分散性及びオルガノポリシロキサンに対する可溶性が向上する。 In the present invention, a part of the anion group of the polyanion, specifically, an excess anion group not doped into the π-conjugated conductive polymer is selected from the group consisting of secondary amine, tertiary amine, and quaternary ammonium salt. One or more amine compounds to be coordinated or bonded as an ion pair. When the amine compound is coordinated or bonded to the surplus anion group as an ion pair, the hydrophilicity is lowered and the hydrophobicity is improved, so that the organic solvent dispersibility of the composite and the solubility in the organopolysiloxane are improved.
余剰のアニオン基に配位または結合するアミン系化合物は、炭素数４以上のアルキル基、アリール基、アラルキル基、アルキレン基、アリーレン基、アラルキレン基及びオキシアルキレン基より選択される置換基よりなる群から選ばれる置換基を１つ以上有する。余剰のアニオン基に配位または結合するアミン系化合物が、前記置換基を有することにより、疎水性をより高めることができる。
炭素数４以上のアルキル基としては、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ウンデシル基、ドデシル基等が挙げられる。
アリール基としてはフェニル基、トリル基、キシリル基、ナフチル基等が挙げられる。
アラルキル基としては、ベンジル基、フェネチル基等が挙げられる。
アルキレン基としては、エチレン基、プロピレン基、ブチレン基等が挙げられる。
アリーレン基としては、フェニレン基、ナフチレン基等が挙げられる。
アラルキレン基としては、ベンジレン基、フェネチレン基等が挙げられる。
オキシアルキレン基としては、エチレンオキサイド基、プロピレンオキサイド基、テトラエチレンオキサイド基等が挙げられる。
The amine compound coordinated or bonded to the surplus anionic group is a group consisting of a substituent selected from an alkyl group having 4 or more carbon atoms, an aryl group, an aralkyl group, an alkylene group, an arylene group, an aralkylene group and an oxyalkylene group One or more substituents selected from The amine compound that coordinates or binds to the surplus anion group has the above-described substituent, whereby the hydrophobicity can be further increased.
Examples of the alkyl group having 4 or more carbon atoms include butyl group, pentyl group, hexyl group, heptyl group, octyl group, undecyl group, dodecyl group and the like.
Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
Examples of the aralkyl group include a benzyl group and a phenethyl group.
Examples of the alkylene group include an ethylene group, a propylene group, and a butylene group.
Examples of the arylene group include a phenylene group and a naphthylene group.
Examples of the aralkylene group include a benzylene group and a phenethylene group.
Examples of the oxyalkylene group include an ethylene oxide group, a propylene oxide group, and a tetraethylene oxide group.
前記置換基を有する２級アミンとしては、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、ジブチルアミン、ジ−２−エチルヘキシルアミン、ジオクチルアミン、ジウンデシルアミン、ジドデシルアミン、ジヘプチルアミン等が挙げられる。
前記置換基を有する３級アミンとしては、トリブチルアミン、トリペンチルアミン、トリヘキシルアミン、トリヘプチルアミン、トリオクチルアミン、トリデシルアミン、トリウンデシルアミン、トリドデシルアミン、トリフェニルアミン、トリベンジルアミン、トリパーフルオロプロピルアミン、トリパーフルオロブチルアミン、トリ−２−エチルヘキシルアミン、ジデシルメチルアミン、ジメチルオクタデシルアミン、ジドデシルアミン、Ｎ，Ｎ−ジベンジルアニリン等が挙げられる。
前記置換基を有する４級アンモニウム塩としては、メチルトリヘキシルアンモニウムクロライド、メチルトリオクチルアンモニウムクロライド、メチルトリデシルアンモニウムクロライド、メチルトリドデシルアンモニウムクロライド、ジオクチルジメチルアンモニウムブロマイド、ジデシルジメチルアンモニウムブロマイド、ジドデシルジメチルアンモニウムブロマイド、テトラヘキシルアンモニウムブロマイド、テトラオクチルアンモニウムブロマイド、テトラデシルアンモニウムブロマイド、テトラドデシルアンモニウムブロマイド、１−ドデシル−２−メチル−３−ベンジルイミダゾリウムクロライド、１−テトラデシル−２−メチル−３−ベンジルイミダゾリウムクロライド、１−ヘキサデシル−２−メチル−３−ベンジルイミダゾリウムクロライド、１−オクタデシル−２−メチル−３−ベンジルイミダゾリウムクロライド、１−ヘキシル−３−メチルイミダゾリウムクロライド、１−オクチル−３−メチルイミダゾリウムクロライド、メチルピリジニウムクロライド、エチルピリジニウムクロライド、プロピルピリジニウムクロライド、ブチルピリジニウムクロライド、ヘキシルピリジニウムクロライド、オクチルピリジニウムクロライド、デシルピリジニウムクロライド、ドデシルピリジニウムクロライド、ヘキサドデシルピリジニウムクロライド等が挙げられる。
前記置換基を有するアミンアルキレンオキサイドとしては、例えば、下記式（３）及び式（４）で示される化合物が挙げられる。
式中、Ｒ５、Ｒ６及びＲ７は、それぞれ独立して、炭素数１〜２４のアルキル基を表し、Ａ１Ｏ、Ａ２ＯおよびＡ３Ｏは、それぞれ独立して、炭素数２〜４のオキシアルキレン基若しくはその混合物を表し、ｐ、ｑおよびｒは、それぞれ独立して、１≦ｐ、ｑ、ｒ≦１００であって、０＜ｑ＋ｒ≦１００を満たす。ここで、Ｒ１、Ｒ２、Ｒ３置換基中のいずれかの炭素数或いは（Ａ１Ｏ）ｐ、（Ａ２Ｏ）ｑ、（Ａ３Ｏ）ｒ置換基中のＡ１×ｐ、Ａ２×ｑ、Ａ３×ｒ、のいずれかにおける炭素数の合計が４以上であることが必要である。
具体的には、三洋化成工業株式会社、商品名『イオネット』、日油株式会社 商品名『ナイミーン』、ライオンアクゾ株式会社 商品名『エソミン』などの各シリーズから選択可能である。
Examples of the secondary amine having a substituent include methyloctylamine, methylbenzylamine, N-methylaniline, dibutylamine, di-2-ethylhexylamine, dioctylamine, diundecylamine, didodecylamine, and diheptylamine. Can be mentioned.
The tertiary amine having the substituent is tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, tridecylamine, triundecylamine, tridodecylamine, triphenylamine, tribenzylamine. , Triperfluoropropylamine, triperfluorobutylamine, tri-2-ethylhexylamine, didecylmethylamine, dimethyloctadecylamine, didodecylamine, N, N-dibenzylaniline and the like.
Examples of the quaternary ammonium salt having a substituent include methyltrihexylammonium chloride, methyltrioctylammonium chloride, methyltridecylammonium chloride, methyltridodecylammonium chloride, dioctyldimethylammonium bromide, didecyldimethylammonium bromide, and didodecyldimethyl. Ammonium bromide, tetrahexylammonium bromide, tetraoctylammonium bromide, tetradecylammonium bromide, tetradodecylammonium bromide, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 1-tetradecyl-2-methyl-3-benzylimidazo Rium chloride, 1-hexadecyl-2-methyl-3-benzylimida Lilium chloride, 1-octadecyl-2-methyl-3-benzylimidazolium chloride, 1-hexyl-3-methylimidazolium chloride, 1-octyl-3-methylimidazolium chloride, methylpyridinium chloride, ethylpyridinium chloride, propylpyridinium Examples include chloride, butylpyridinium chloride, hexylpyridinium chloride, octylpyridinium chloride, decylpyridinium chloride, dodecylpyridinium chloride, hexadodecylpyridinium chloride, and the like.
As an amine alkylene oxide which has the said substituent, the compound shown by following formula (3) and Formula (4) is mentioned, for example.
In the formula, R 5 , R 6 and R 7 each independently represent an alkyl group having 1 to 24 carbon atoms, and A 1 O, A 2 O and A 3 O each independently represent 2 carbon atoms. Represents an oxyalkylene group of ˜4 or a mixture thereof, and p, q, and r each independently satisfy 1 ≦ p, q, r ≦ 100, and satisfy 0 <q + r ≦ 100. Here, the number of carbon atoms in the R 1 , R 2 , and R 3 substituents, or A 1 × p in the (A 1 O) p , (A 2 O) q , and (A 3 O) r substituents, The total number of carbon atoms in either A 2 × q or A 3 × r is required to be 4 or more.
Specifically, Sanyo Kasei Kogyo Co., Ltd., trade name “Ionet”, NOF Corporation trade name “Naymin”, Lion Akzo Co., Ltd. trade name “Esomin”, etc. can be selected.
アミン系化合物の量は、ポリアニオンに対して０．１〜１０モル当量であることが好ましく、０．５〜２．０モル当量であることがより好ましく、０．８５〜１．２５モル当量であることがさらに好ましい。 The amount of the amine compound is preferably 0.1 to 10 molar equivalents, more preferably 0.5 to 2.0 molar equivalents relative to the polyanion, and 0.85 to 1.25 molar equivalents. More preferably it is.
（有機溶媒）
本発明の帯電防止性剥離剤用組成物に含まれる有機溶媒としては、剥離性成分を溶解させる溶剤（トルエン、キシレン、酢酸エステル）を使用してもよいし、導電性成分を溶解させる溶剤（メチルエチルケトン等のケトン溶媒、イソプロピルアルコール等のアルコール溶媒）を使用してもよいし、これらを併用してもよい。
有機溶媒の含有量は、各成分の配合や剥離剤層の目標の厚み等に応じて適宜調整されるが、通常は、剥離性成分と導電性成分の合計質量を１とした際に、０．１〜１００の範囲とされる。
(Organic solvent)
As an organic solvent contained in the composition for antistatic release agent of the present invention, a solvent (toluene, xylene, acetate ester) for dissolving the peelable component may be used, or a solvent for dissolving the conductive component ( Ketone solvents such as methyl ethyl ketone, alcohol solvents such as isopropyl alcohol), or these may be used in combination.
The content of the organic solvent is appropriately adjusted according to the composition of each component, the target thickness of the release agent layer, and the like. Usually, when the total mass of the release component and the conductive component is 1, the content is 0. .1 to 100.
（導電性向上剤）
本発明の帯電防止性剥離フィルムには、二次ドーパントとしての導電性向上剤が含まれてもよい。
導電性向上剤としては、グリシジル化合物、極性溶媒（ただし、前記有機溶媒を除く。）、多価脂肪族アルコール、窒素含有芳香族性環式化合物、２個以上のヒドロキシ基を有する化合物、２個以上のカルボキシ基を有する化合物、１個以上のヒドロキシ基と１個以上のカルボキシ基を有する化合物、ラクタム化合物等が挙げられる。これらは１種のみを使用してもよいし、２種以上を併用してもよい。
これらのなかでも、紫外線硬化を阻害しにくいものが好ましい。剥離性成分の硬化を阻害しにくければ、該帯電防止性剥離剤用組成物から得た剥離剤層に、粘着シートの粘着剤層を重ねた後、粘着剤層に剥離剤用組成物が転写することを防ぐことができる。
剥離性成分の硬化を阻害しにくい導電性向上剤としては、グリシジル化合物、極性溶媒、多価脂肪族アルコールが挙げられる。
また、導電性向上剤は、２５℃で液状であることが好ましい。液状であれば、該帯電防止性剥離剤用組成物から形成した剥離剤層の透明性を向上させることができ、剥離剤層に貼り合わされる粘着剤層への異物の転写を防ぐことができる。
(Conductivity improver)
The antistatic release film of the present invention may contain a conductivity improver as a secondary dopant.
Examples of the conductivity improver include a glycidyl compound, a polar solvent (excluding the organic solvent), a polyhydric aliphatic alcohol, a nitrogen-containing aromatic cyclic compound, a compound having two or more hydroxy groups, two Examples thereof include compounds having the above carboxy groups, compounds having one or more hydroxy groups and one or more carboxy groups, and lactam compounds. These may use only 1 type and may use 2 or more types together.
Among these, those that are difficult to inhibit ultraviolet curing are preferable. If it is difficult to inhibit curing of the peelable component, the adhesive layer of the adhesive sheet is superimposed on the release agent layer obtained from the antistatic release agent composition, and then the release agent composition is transferred to the adhesive layer. Can be prevented.
Examples of the conductivity improver that does not easily inhibit the peelable component include a glycidyl compound, a polar solvent, and a polyhydric aliphatic alcohol.
Further, the conductivity improver is preferably liquid at 25 ° C. If it is liquid, the transparency of the release agent layer formed from the antistatic release agent composition can be improved, and transfer of foreign matter to the adhesive layer bonded to the release agent layer can be prevented. .
グリシジル化合物の具体例としては、エチルグリシジルエーテル、ｎ−ブチルグリシジルエーテル、ｔ−ブチルグリシジルエーテル、アリルグリシジルエーテル、ベンジルグリシジルエーテル、グリシジルフェニルエーテル、ビスフェノールＡジグリシジルエーテル、アクリル酸グリシジルエーテル、メタクリル酸グリシジルエーテル等が挙げられる。
極性溶媒の具体例としては、Ｎ−メチルホルムアミド、Ｎ−メチルアクリルアミド、Ｎ−メチルメタクリルアミド、Ｎ−エチルアクリルアミド、Ｎ−エチルメタクリルアミド、Ｎ，Ｎ−ジメチルアクリルアミド、Ｎ，Ｎ−ジメチルメタクリルアミド、Ｎ，Ｎ−ジエチルアクリルアミド、Ｎ，Ｎ−ジエチルメタクリルアミド、２−ヒドロキシエチルアクリルアミド、２−ヒドロキシエチルメタクリルアミド、Ｎ−メチロールアクリルアミド、Ｎ−メチロールメタクリルアミド、Ｎ−メチル−２−ピロリドン、Ｎ−メチルアセトアミド、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、ジメチルスルホキシド、ヘキサメチレンホスホルトリアミド、Ｎ−ビニルピロリドン、Ｎ−ビニルホルムアミド、Ｎ−ビニルアセトアミド、乳酸メチル、乳酸エチル、乳酸プロピル等が挙げられる。
多価脂肪族アルコールとしては、エチレングリコール、ジエチレングリコール、プロピレングリコール、１，３−ブチレングリコール、１，４−ブチレングリコール、グリセリン、ジグリセリン、イソプレングリコール、ブタンジオール、１，５−ペンタンジオール、１，６−ヘキサンジオール、１，９−ノナンジオール、ネオペンチルグリコール、トリメチロールエタン、トリメチロールプロパン、チオジエタノール、ジプロピレングリコール等が挙げられる。
Specific examples of glycidyl compounds include ethyl glycidyl ether, n-butyl glycidyl ether, t-butyl glycidyl ether, allyl glycidyl ether, benzyl glycidyl ether, glycidyl phenyl ether, bisphenol A diglycidyl ether, glycidyl methacrylate, glycidyl methacrylate Examples include ether.
Specific examples of the polar solvent include N-methylformamide, N-methylacrylamide, N-methylmethacrylamide, N-ethylacrylamide, N-ethylmethacrylamide, N, N-dimethylacrylamide, N, N-dimethylmethacrylamide, N, N-diethylacrylamide, N, N-diethylmethacrylamide, 2-hydroxyethylacrylamide, 2-hydroxyethylmethacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, N-methyl-2-pyrrolidone, N-methyl Acetamide, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, hexamethylene phosphortriamide, N-vinylpyrrolidone, N-vinylformamide, N-vinylacetamide, milk Methyl, ethyl lactate, propyl and the like.
Examples of the polyhydric aliphatic alcohol include ethylene glycol, diethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, glycerin, diglycerin, isoprene glycol, butanediol, 1,5-pentanediol, 1, Examples include 6-hexanediol, 1,9-nonanediol, neopentyl glycol, trimethylol ethane, trimethylol propane, thiodiethanol, and dipropylene glycol.
導電性向上剤の含有量は、導電性成分１００質量部に対して１０〜１００００質量部であることが好ましく、３０〜５０００質量部であることがより好ましい。導電性向上剤の含有量が前記下限値以上であれば、帯電防止性をより向上させることができる。しかし、前記上限値を超えると、剥離性が低下するおそれがある。 The content of the conductivity improver is preferably 10 to 10000 parts by mass and more preferably 30 to 5000 parts by mass with respect to 100 parts by mass of the conductive component. When the content of the conductivity improver is at least the lower limit, the antistatic property can be further improved. However, if the upper limit is exceeded, the peelability may be reduced.
（作用効果）
従来、π共役系導電性高分子にポリアニオンがドープした複合体は、剥離性成分を構成する紫外線硬化型オルガノポリシロキサンとの可溶性が低かった。そのため、π共役系導電性高分子にポリアニオンがドープした複合体と紫外線硬化型オルガノポリシロキサンとを混合しても、互いに均一に混ざらず、帯電防止性及び剥離性を共に充分に発揮することは困難であった。
しかし、本発明では、ポリアニオンの余剰のアニオン基に、上記特定の置換基を有するアミン系化合物を配位または結合させているため、複合体の疎水性が向上している。これにより、π共役系導電性高分子にポリアニオンがドープした複合体と紫外線硬化型オルガノポリシロキサンとの可溶性が高くなっており、互いに均一分散している。そのため、帯電防止性及び剥離性を共に発揮させることができる。
なお、本明細書において、「可溶性」とは、分子レベルのミクロな可溶化の程度に限定されず、マクロな可溶化の程度のことを含む。したがって、可溶性が高い場合には、ミクロな観察（例えば、電子顕微鏡）では分離しているが、マクロな観察（例えば、目視）では互いに可溶化している状態を含む。
(Function and effect)
Conventionally, a composite in which a π-conjugated conductive polymer is doped with a polyanion has low solubility with an ultraviolet curable organopolysiloxane constituting a peelable component. Therefore, even if a complex in which a polyanion is doped into a π-conjugated conductive polymer and an ultraviolet curable organopolysiloxane are mixed, they are not mixed uniformly with each other, and both antistatic properties and peelability can be sufficiently exhibited. It was difficult.
However, in the present invention, since the amine compound having the specific substituent is coordinated or bonded to the surplus anion group of the polyanion, the hydrophobicity of the complex is improved. As a result, the solubility of the complex in which the π-conjugated conductive polymer is doped with the polyanion and the ultraviolet curable organopolysiloxane is high, and they are uniformly dispersed with each other. Therefore, both antistatic properties and peelability can be exhibited.
In the present specification, the term “soluble” is not limited to the degree of microscopic solubilization at the molecular level, but includes the degree of macroscopic solubilization. Therefore, when the solubility is high, the microscopic observation (for example, an electron microscope) separates, but the macro observation (for example, visual observation) includes a state of being solubilized with each other.
また、本発明の帯電防止性剥離剤用組成物は、非水系であるため、プラスチックフィルムに対する密着性が高い。本発明の帯電防止性剥離剤用組成物は、紙に対しても密着性が高い。
さらに、本発明の帯電防止性剥離剤用組成物は、透明性にも優れる。
Moreover, since the composition for antistatic release agent of this invention is non-aqueous, its adhesiveness with respect to a plastic film is high. The antistatic release agent composition of the present invention has high adhesion to paper.
Furthermore, the antistatic release agent composition of the present invention is also excellent in transparency.
＜帯電防止性剥離フィルム＞
本発明の帯電防止性剥離フィルムは、プラスチックフィルムまたは紙からなる基材と、該基材の少なくとも片面に形成された剥離剤層とを備える。
本発明の帯電防止性剥離フィルムを構成する剥離剤層は、上記帯電防止性剥離剤用組成物より形成された層である。
<Antistatic release film>
The antistatic release film of the present invention comprises a base material made of a plastic film or paper and a release agent layer formed on at least one side of the base material.
The release agent layer constituting the antistatic release film of the present invention is a layer formed from the antistatic release agent composition.
プラスチックフィルムを構成する樹脂材料としては、例えば、ポリエチレン、ポリプロピレン、ポリスチレン、ポリ塩化ビニル、ポリビニルアルコール、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリアクリル、ポリカーボネート、ポリフッ化ビニリデン、ポリアリレート、スチレン系エラストマー、ポリエステル系エラストマー、ポリエーテルスルホン、ポリエーテルイミド、ポリエーテルエーテルケトン、ポリフェニレンスルフィド、ポリアリレート、ポリイミド、ポリカーボネート、セルローストリアセテート、セルロースアセテートプロピオネートなどが挙げられる。これらの樹脂材料の中でも、透明性、可撓性、汚染防止性及び強度等の点から、ポリエチレンテレフタレートが好ましい。
紙としては、上質紙、クラフト紙、コート紙等を用いることができる。
Examples of the resin material constituting the plastic film include polyethylene, polypropylene, polystyrene, polyvinyl chloride, polyvinyl alcohol, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacryl, polycarbonate, polyvinylidene fluoride, polyarylate, and styrene. Examples include elastomers, polyester-based elastomers, polyethersulfone, polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate, cellulose triacetate, and cellulose acetate propionate. Among these resin materials, polyethylene terephthalate is preferable in terms of transparency, flexibility, antifouling property, strength, and the like.
As the paper, high-quality paper, kraft paper, coated paper or the like can be used.
帯電防止性剥離フィルムの製造方法としては、プラスチックフィルムの少なくとも片面に上記帯電防止性剥離剤用組成物を塗布し、紫外線を照射する方法が挙げられる。
帯電防止性剥離剤用組成物の塗布方法としては、例えば、バーコーター、グラビアコーター、エアーナイフコーター、ロールコーター、ワイヤーバーなどの塗工機を用いる方法が適用される。塗布量としては特に制限はないが、通常は、固形分として、０．１〜１０．０ｇ／ｍ２の範囲とされる。
紫外線の光源としては、高圧水銀ランプ、中圧水銀ランプ、低圧水銀ランプ、メタルハライドランプ、水銀アーク灯などが例示できる。塗布により形成された塗膜を硬化させるために、高圧水銀ランプ（８０Ｗ／ｃｍ）を使用した場合には、５〜２０ｃｍの距離から０．０１〜２００ 秒照射すればよく、紫外線照射量としては５〜５０００ｍＪ／ｃｍ２とすればよい。
Examples of the method for producing an antistatic release film include a method of applying the antistatic release agent composition to at least one surface of a plastic film and irradiating with ultraviolet rays.
As a method for applying the antistatic release agent composition, for example, a method using a coating machine such as a bar coater, a gravure coater, an air knife coater, a roll coater, or a wire bar is applied. Although there is no restriction | limiting in particular as an application quantity, Usually, it is set as the range of 0.1-10.0 g / m < 2 > as solid content.
Examples of the ultraviolet light source include a high-pressure mercury lamp, a medium-pressure mercury lamp, a low-pressure mercury lamp, a metal halide lamp, and a mercury arc lamp. When a high-pressure mercury lamp (80 W / cm) is used to cure the coating film formed by coating, it may be irradiated for 0.01 to 200 seconds from a distance of 5 to 20 cm. What is necessary is just to be 5-5000 mJ / cm < 2 >.
本発明の帯電防止性剥離フィルムは、上記帯電防止性剥離剤用組成物を含む剥離剤層を備えるから、帯電防止性と剥離性とが共に優れたものとなる。そのため、本発明の帯電防止性剥離フィルムは、光学用や電子電気部品用の粘着シートに対して好適に使用される。 Since the antistatic release film of the present invention comprises a release agent layer containing the antistatic release agent composition, both the antistatic property and the release property are excellent. Therefore, the antistatic release film of this invention is used suitably with respect to the adhesive sheet for optical or electronic / electrical components.
以下に、実施例及び比較例を示すが、本発明は、下記実施例に限定されるものではない。なお、以下の例における「部」は「質量部」、「％」は「質量％」のことである。 Examples and Comparative Examples are shown below, but the present invention is not limited to the following Examples. In the following examples, “part” means “part by mass”, and “%” means “mass%”.
（製造例１）
１０００ｍｌのイオン交換水に２０６ｇのスチレンスルホン酸ナトリウムを溶解し、８０℃で攪拌しながら、予め１０ｍｌの水に溶解した１．１４ｇの過硫酸アンモニウム酸化剤溶液を２０分間滴下し、この溶液を１２時間攪拌した。
得られたスチレンスルホン酸ナトリウム含有溶液に１０％に希釈した硫酸を１０００ｍｌ添加し、限外ろ過法によりポリスチレンスルホン酸含有溶液の約１０００ｍｌ溶液を除去し、残液に２０００ｍｌのイオン交換水を加え、限外ろ過法により約２０００ｍｌ溶液を除去した。上記の限外ろ過操作を３回繰り返した。さらに、得られたろ液に約２０００ｍｌのイオン交換水を添加し、限外ろ過法により約２０００ｍｌの溶液を除去した。
この限外ろ過操作を３回繰り返した。
得られた溶液中の水を減圧除去して、無色の固形状の質量平均分子量３０万のポリスチレンスルホン酸を得た。
(Production Example 1)
Dissolve 206 g of sodium styrenesulfonate in 1000 ml of ion-exchanged water and, while stirring at 80 ° C., add dropwise 1.14 g of ammonium persulfate oxidizer solution previously dissolved in 10 ml of water for 20 minutes. Stir.
1000 ml of sulfuric acid diluted to 10% was added to the obtained sodium styrenesulfonate-containing solution, about 1000 ml of the polystyrenesulfonic acid-containing solution was removed by ultrafiltration, and 2000 ml of ion-exchanged water was added to the remaining solution, About 2000 ml of solution was removed by ultrafiltration. The above ultrafiltration operation was repeated three times. Further, about 2000 ml of ion-exchanged water was added to the obtained filtrate, and about 2000 ml of the solution was removed by ultrafiltration.
This ultrafiltration operation was repeated three times.
Water in the obtained solution was removed under reduced pressure to obtain a colorless solid polystyrene sulfonic acid having a weight average molecular weight of 300,000.
（製造例２）
１４．２ｇの３，４−エチレンジオキシチオフェンと、製造例１で得た質量平均分子量２０万のポリスチレンスルホン酸３６．７ｇを２０００ｍｌのイオン交換水に溶かした溶液とを２０℃で混合させた。
これにより得られた混合溶液を２０℃に保ち、掻き混ぜながら、２００ｍｌのイオン交換水に溶かした２９．６４ｇの過硫酸アンモニウムと８．０ｇの硫酸第二鉄の酸化触媒溶液とをゆっくり添加し、３時間攪拌して反応させた。
得られた反応液に２０００ｍｌのイオン交換水を加え、限外ろ過法により約２０００ｍｌ溶液を除去した。この操作を３回繰り返した。
そして、得られた溶液に２００ｍｌの１０％に希釈した硫酸と２０００ｍｌのイオン交換水とを加え、限外ろ過法により約２０００ｍｌの溶液を除去し、これに２０００ｍｌのイオン交換水を加え、限外ろ過法により約２０００ｍｌ溶液を除去した。この操作を３回繰り返した。
さらに、得られた溶液に２０００ｍｌのイオン交換水を加え、限外ろ過法により約２０００ｍｌの溶液を除去した。この操作を５回繰り返し、濃度１．２％のポリスチレンスルホン酸ドープポリ（３，４−エチレンジオキシチオフェン）の水分散液（ＰＥＤＯＴ−ＰＳＳ水分散液）を得た。
(Production Example 2)
14.2 g of 3,4-ethylenedioxythiophene and a solution obtained by dissolving 36.7 g of polystyrene sulfonic acid having a mass average molecular weight of 200,000 obtained in Production Example 1 in 2000 ml of ion-exchanged water were mixed at 20 ° C. .
While maintaining the mixed solution thus obtained at 20 ° C. and stirring, 29.64 g of ammonium persulfate dissolved in 200 ml of ion exchange water and 8.0 g of ferric sulfate oxidation catalyst solution were slowly added, The reaction was stirred for 3 hours.
2000 ml of ion-exchanged water was added to the obtained reaction solution, and about 2000 ml of solution was removed by ultrafiltration. This operation was repeated three times.
Then, 200 ml of sulfuric acid diluted to 10% and 2000 ml of ion exchange water are added to the obtained solution, and about 2000 ml of solution is removed by ultrafiltration, and 2000 ml of ion exchange water is added thereto, About 2000 ml of solution was removed by filtration. This operation was repeated three times.
Furthermore, 2000 ml of ion-exchanged water was added to the obtained solution, and about 2000 ml of the solution was removed by ultrafiltration. This operation was repeated 5 times to obtain an aqueous dispersion (PEDOT-PSS aqueous dispersion) of polystyrenesulfonic acid-doped poly (3,4-ethylenedioxythiophene) having a concentration of 1.2%.
(製造例３）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとトリオクチルアミン１０．６ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 3)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 10.6 g of trioctylamine were added and stirred to obtain an isopropanol dispersion (1) of PEDOT-PSS having a concentration of 0.4%. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例４）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとトリブチルアミン５．７ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（２）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 4)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 5.7 g of tributylamine were added and stirred to obtain an isopropanol dispersion (2) of PEDOT-PSS having a concentration of 0.4%. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例５）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとトリヘキシルアミン１０．６ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（３）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 5)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 10.6 g of trihexylamine were added and stirred to obtain an isopropanol dispersion (3) of PEDOT-PSS having a concentration of 0.4%. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例６）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとエソミンＣ／２５、１０．８ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（４）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 6)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 10.8 g of Esomine C / 25 were added and stirred to obtain an isopropanol dispersion (4) of PEDOT-PSS having a concentration of 0.4%. It was. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例７）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとトリエチルアミン４．２ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（５）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 7)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 4.2 g of triethylamine were added and stirred to obtain an isopropanol dispersion (5) of PEDOT-PSS having a concentration of 0.4%. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例８）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとトリプロピルアミン４．４ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（６）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 8)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 4.4 g of tripropylamine were added and stirred to obtain an isopropanol dispersion (6) of PEDOT-PSS having a concentration of 0.4%. The obtained dispersion was blue transparent and uniformly dispersed.
(製造例９）
製造例２で得たＰＥＤＯＴ−ＰＳＳ水分散液、１０００ｇを凍結乾燥して、１２ｇのＰＥＤＯＴ−ＰＳＳの粉体を得た。得られたＰＥＤＯＴ−ＰＳＳの粉体１２．０ｇにイソプロパノール２８８２ｇとモノｎ−ヘキシルアミン３．０ｇを添加し、攪拌して、濃度０．４％のＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（７）を得た。得られた分散液は青色透明で均一に分散していた。
(Production Example 9)
1000 g of the PEDOT-PSS aqueous dispersion obtained in Production Example 2 was freeze-dried to obtain 12 g of PEDOT-PSS powder. To 12.0 g of the obtained PEDOT-PSS powder, 2882 g of isopropanol and 3.0 g of mono-n-hexylamine were added and stirred to obtain an isopropanol dispersion (7) of PEDOT-PSS having a concentration of 0.4%. It was. The obtained dispersion was blue transparent and uniformly dispersed.
（実施例１）
製造例３で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇに、下記式で示されるアクリル基含有オルガノポリシオキサンを３ｇ、光重合開始剤として２−ヒドロキシ−２−メチルプロピオフェノンを０．１５５ｇ添加した。さらに、メチルエチルケトン５６．８４５ｇ及びジアセトンアルコール１０．０ｇで希釈し、合計１００ｇの剥離剤用組成物を得た。
Example 1
30 g of the PEDOT-PSS isopropanol dispersion (1) obtained in Production Example 3 was added with 3 g of an acryl group-containing organopolythioxan represented by the following formula, and 2-hydroxy-2-methylpropiophenone as a photopolymerization initiator. 0.155 g was added. Furthermore, it diluted with methyl ethyl ketone 56.845g and diacetone alcohol 10.0g, and obtained the composition for 100 g of stripping agents in total.
（実施例２）
実施例１の剥離剤用組成物にジメチルスルホオキシドを０．３ｇ加えた以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 2)
A release agent composition was obtained in the same manner as in Example 1 except that 0.3 g of dimethyl sulfoxide was added to the release agent composition of Example 1.
（実施例３）
実施例１の剥離剤用組成物にエチレングリコールを０．３ｇ加えた以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 3)
A release agent composition was obtained in the same manner as in Example 1 except that 0.3 g of ethylene glycol was added to the release agent composition of Example 1.
（実施例４）
実施例１の剥離剤用組成物にヒドロキシエチルアクリルアミドを０．３ｇ加えた以外は実施例１と同様にして剥離剤用組成物を得た。
Example 4
A release agent composition was obtained in the same manner as in Example 1 except that 0.3 g of hydroxyethylacrylamide was added to the release agent composition of Example 1.
（実施例５）
実施例１の剥離剤用組成物に乳酸エチルを０．３ｇ加えた以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 5)
A release agent composition was obtained in the same manner as in Example 1 except that 0.3 g of ethyl lactate was added to the release agent composition of Example 1.
（実施例６）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を５ｇに、希釈溶剤のメチルエチルケトンを８１．８４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 6)
A release agent composition was obtained in the same manner as in Example 1 except that the PEDOT-PSS isopropanol dispersion (1) was changed to 5 g and the methyl ethyl ketone as a diluent solvent was changed to 81.845 g.
（実施例７）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を１０ｇに、希釈溶剤のメチルエチルケトンを７６．８４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 7)
A release agent composition was obtained in the same manner as in Example 1, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 10 g and the dilution solvent methyl ethyl ketone was changed to 76.845 g.
（実施例８）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を５０ｇに、希釈溶剤のメチルエチルケトンを３６．８４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 8)
A release agent composition was obtained in the same manner as in Example 1, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 50 g and the methyl ethyl ketone as a diluent solvent was changed to 36.845 g.
（実施例９）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を１００ｇに変更し、希釈溶剤のメチルエチルケトンとジアセトンアルコールを添加しなかった以外は実施例１と同様にして剥離剤用組成物を得た。
Example 9
In Example 1, a PEDOT-PSS isopropanol dispersion (1) was changed to 100 g, and a release agent composition was obtained in the same manner as in Example 1 except that methyl ethyl ketone and diacetone alcohol as dilution solvents were not added. It was.
（比較例１０）
実施例９において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を３００ｇに変更した以外は実施例９と同様にして剥離剤用組成物を得た。
( Comparative Example 10)
In Example 9, the composition for peeling agents was obtained like Example 9 except having changed the isopropanol dispersion (1) of PEDOT-PSS into 300g.
（比較例１１）
実施例９において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を５００ｇに変更した以外は実施例９と同様にして剥離剤用組成物を得た。
( Comparative Example 11)
A release agent composition was obtained in the same manner as in Example 9, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 500 g.
（比較例１２）
実施例９において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を１０００ｇに変更した以外は実施例９と同様にして剥離剤用組成物を得た。
( Comparative Example 12)
A release agent composition was obtained in the same manner as in Example 9, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 1000 g.
（比較例１３）
実施例９において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を２０００ｇに変更した以外は実施例９と同様にして剥離剤用組成物を得た。
( Comparative Example 13)
A release agent composition was obtained in the same manner as in Example 9, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 2000 g.
（実施例１４）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例４で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（２）６０ｇに変更し、メチルエチルケトン２６．８４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 14)
In Example 1, 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 60 g of the PEDOT-PSS isopropanol dispersion (2) obtained in Production Example 4 and changed to 26.845 g of methyl ethyl ketone. In the same manner as in No. 1, a release agent composition was obtained.
（実施例１５）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例５で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（３）３０ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 15)
In Example 1, except that 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 30 g of the PEDOT-PSS isopropanol dispersion (3) obtained in Production Example 5, the release agent was used in the same manner as in Example 1. A composition was obtained.
（実施例１６）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例６で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（４）３０ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Example 16)
In Example 1, except that 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 30 g of the PEDOT-PSS isopropanol dispersion (4) obtained in Production Example 6, the release agent was used in the same manner as in Example 1. A composition was obtained.
（比較例１）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を配合せず、メチルエチルケトンを８６．８４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Comparative Example 1)
In Example 1, the composition for release agents was obtained like Example 1 except not mix | blending the isopropanol dispersion liquid (1) of PEDOT-PSS and changing methyl ethyl ketone to 86.845g.
（比較例２）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を２．５ｇに、希釈溶剤のメチルエチルケトンを８４．３４５ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Comparative Example 2)
A release agent composition was obtained in the same manner as in Example 1 except that the PEDOT-PSS isopropanol dispersion (1) was changed to 2.5 g and the methyl ethyl ketone as a diluent solvent was changed to 84.345 g.
（比較例３）
実施例９において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）を２５００ｇに変更した以外は実施例９と同様にして剥離剤用組成物を得た。
(Comparative Example 3)
A release agent composition was obtained in the same manner as in Example 9, except that the PEDOT-PSS isopropanol dispersion (1) was changed to 2500 g.
（比較例４）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例７で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（５）３０ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Comparative Example 4)
In Example 1, except that 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 30 g of the PEDOT-PSS isopropanol dispersion (5) obtained in Production Example 7, the release agent was used in the same manner as in Example 1. A composition was obtained.
（比較例５）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例８で得たＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（６）３０ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Comparative Example 5)
In Example 1, except that 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 30 g of the PEDOT-PSS isopropanol dispersion (6) obtained in Production Example 8, the same procedure as in Example 1 was performed. A composition was obtained.
（比較例６）
実施例１において、ＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（１）３０ｇを、製造例９で作製したＰＥＤＯＴ−ＰＳＳのイソプロパノール分散液（７）３０ｇに変更した以外は実施例１と同様にして剥離剤用組成物を得た。
(Comparative Example 6)
In Example 1, except that 30 g of the PEDOT-PSS isopropanol dispersion (1) was changed to 30 g of the PEDOT-PSS isopropanol dispersion (7) prepared in Production Example 9, the same procedure as in Example 1 was performed. A composition was obtained.
＜評価＞
各例の剥離剤用組成物について、剥離に要する力（以下、「剥離強度」という。）、残留接着率、表面抵抗率を以下の方法により評価又は測定した。結果を表１，２に示す。
<Evaluation>
About the composition for release agents of each example, the force required for peeling (hereinafter referred to as “peel strength”), the residual adhesion rate, and the surface resistivity were evaluated or measured by the following methods. The results are shown in Tables 1 and 2.
［剥離強度］
厚さ３８μｍのＰＥＴフィルムに、得られた剥離剤用組成物を、バーコーターによって塗布し、７０℃の熱風式乾燥機中で１０秒分間加熱して溶剤を揮発させた。その後、酸素濃度が３００ｐｐｍの条件下で２０００ｍＪ／ｃｍ2の紫外線を照射しＰＥＴフィルム上に剥離剤層を形成した。該剥離剤層の表面にポリエステル粘着テープ（ニットー３１Ｂ、日東電工（株）製商品名）を載せ、次いで、その粘着テープの上に１９７６Ｐａの荷重を載せて、剥離剤層にポリエステル粘着テープを貼り合せた。そして、引張試験機を用いて、剥離剤層からポリエステル粘着テープを、１８０゜の角度で剥離（剥離速度０．３ｍ／分）し、剥離強度を測定した。剥離強度が小さい程、剥離剤層に粘着シートを貼り合せた後に、粘着シートを容易に剥離できる。すなわち、軽剥離となる。
[Peel strength]
The obtained release agent composition was applied to a PET film having a thickness of 38 μm with a bar coater and heated in a hot air drier at 70 ° C. for 10 seconds to volatilize the solvent. Thereafter, an ultraviolet ray of 2000 mJ / cm 2 was irradiated under an oxygen concentration of 300 ppm to form a release agent layer on the PET film. A polyester pressure-sensitive adhesive tape (Nitto 31B, product name manufactured by Nitto Denko Corporation) is placed on the surface of the release agent layer, and then a load of 1976 Pa is placed on the pressure-sensitive adhesive tape, and the polyester pressure-sensitive adhesive tape is attached to the release agent layer Combined. Then, using a tensile tester, the polyester adhesive tape was peeled from the release agent layer at an angle of 180 ° (peeling speed 0.3 m / min), and the peel strength was measured. The smaller the peel strength, the easier the pressure-sensitive adhesive sheet can be peeled after the pressure-sensitive adhesive sheet is bonded to the release agent layer. That is, light peeling occurs.
［残留接着率］
上記剥離強度の測定と同様に、ＰＥＴフィルム上に剥離剤層を形成し、剥離剤層にポリエステル粘着テープを貼り合せた。その後、室温で２０時間放置し、または、８５℃で２０時間加熱処理してから、剥離剤層からポリエステル粘着テープを剥がし、そのポリエステル粘着テープをステンレス板に貼り付けた。次いで、引張試験機を用いて、ステンレス板からポリエステル粘着テープを剥離し、剥離強度Ｘを測定した。
また、剥離剤層に貼り合せていないポリエステル粘着テープをステンレス板に貼り付け、引張試験機を用いて、ステンレス板からポリエステル粘着テープを剥離し、剥離強度Ｙを測定した。
そして、（剥離強度Ｘ／剥離強度Ｙ）×１００（％）の式より、残留接着率を求めた。残留接着率が高い程、剥離剤層の剥離性に優れ、剥離剤層に貼り合せることによるポリエステル粘着テープの接着力低下が抑制されていることを示す。
[Residual adhesion rate]
Similar to the measurement of the peel strength, a release agent layer was formed on the PET film, and a polyester adhesive tape was bonded to the release agent layer. Thereafter, the polyester adhesive tape was left at room temperature for 20 hours or heat-treated at 85 ° C. for 20 hours, and then the polyester adhesive tape was peeled off from the release agent layer, and the polyester adhesive tape was attached to a stainless steel plate. Subsequently, the polyester adhesive tape was peeled from the stainless steel plate using a tensile tester, and the peel strength X was measured.
Moreover, the polyester adhesive tape which was not bonded to the release agent layer was affixed on the stainless steel plate, the polyester adhesive tape was peeled from the stainless steel plate using a tensile tester, and the peel strength Y was measured.
And the residual adhesive rate was calculated | required from the formula of (peeling strength X / peeling strength Y) x100 (%). The higher the residual adhesive rate, the better the release property of the release agent layer, and the lowering of the adhesive strength of the polyester pressure-sensitive adhesive tape due to bonding to the release agent layer is suppressed.
［表面抵抗率］
三菱化学社製ハイレスタＭＣＰ−ＨＴ４５０を用い、プローブＭＣＰ−ＨＴＰ１２、印加電圧１０Ｖで測定した。なお、表中の「ＯＶＥＲ」とは、表面抵抗率が高すぎて、測定できないことを意味している。
[Surface resistivity]
Measured with a probe MCP-HTP12 and an applied voltage of 10 V using a Hiresta MCP-HT450 manufactured by Mitsubishi Chemical Corporation. Note that “OVER” in the table means that the surface resistivity is too high to be measured.
実施例１〜１６の剥離剤用組成物は、剥離強度が小さく、表面抵抗率が低かった。
導電性成分を含まない比較例１の剥離剤用組成物、導電性成分の含有量が少ない比較例２の剥離剤用組成物は、表面抵抗率が高すぎて、測定不能であった。
導電性成分の含有量が多く、相対的に剥離性成分が少ない比較例３の剥離剤用組成物は、剥離性が低かった。
ポリスチレンスルホン酸の余剰スルホン酸基に配位または結合する３級アミンの置換基の炭素数が４未満である比較例４，５の剥離剤用組成物は、表面抵抗率が高すぎて、測定不能であった。
ポリスチレンスルホン酸の余剰スルホン酸基に配位または結合するアミン系化合物の置換基が１級アミンである比較例６の剥離剤用組成物は、表面抵抗率が高すぎて、測定不能であった。
The compositions for release agents of Examples 1 to 16 had low peel strength and low surface resistivity.
The composition for the release agent of Comparative Example 1 that did not contain the conductive component and the composition for the release agent of Comparative Example 2 that contained a small amount of the conductive component were too high to be measured because of the high surface resistivity.
The composition for the release agent of Comparative Example 3 having a high content of conductive component and relatively few peelable components had low peelability.
The composition for the release agent of Comparative Examples 4 and 5 in which the number of carbon atoms of the tertiary amine coordinated or bonded to the excess sulfonic acid group of polystyrene sulfonic acid is less than 4 has a surface resistivity that is too high. It was impossible.
The composition for the release agent of Comparative Example 6 in which the substituent of the amine compound coordinated or bonded to the excess sulfonic acid group of the polystyrene sulfonic acid is a primary amine was too high to measure due to the high surface resistivity. .
Claims (2)
前記ポリスチレンスルホン酸の一部のアニオン基に、２級アミン、３級アミン、４級アンモニウム塩からなる群から選択される１種以上のアミン系化合物がイオン対として配位または結合しており、
前記アミン系化合物は、炭素数４以上のアルキル基、アリール基、アラルキル基、アルキレン基、アリーレン基、アラルキレン基及びオキシアルキレン基よりなる群から選ばれる置換基を１つ以上有する、帯電防止性剥離剤用組成物。 Contains a peelable component containing an ultraviolet curable organopolysiloxane and a photopolymerization initiator, a conductive component containing a composite of polyethylene dioxythiophene and polystyrene sulfonic acid, and an organic solvent, and the content of the conductive component is , 0.7 to 13.3 parts by mass with respect to 100 parts by mass of the peelable component,
One or more amine compounds selected from the group consisting of secondary amines, tertiary amines, and quaternary ammonium salts are coordinated or bonded as ion pairs to some anionic groups of the polystyrene sulfonic acid ,
The amine compound has one or more substituents selected from the group consisting of an alkyl group having 4 or more carbon atoms, an aryl group, an aralkyl group, an alkylene group, an arylene group, an aralkylene group, and an oxyalkylene group. Pharmaceutical composition.
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