JPH0481469A - Conductive resin composition - Google Patents
Conductive resin compositionInfo
- Publication number
- JPH0481469A JPH0481469A JP17532390A JP17532390A JPH0481469A JP H0481469 A JPH0481469 A JP H0481469A JP 17532390 A JP17532390 A JP 17532390A JP 17532390 A JP17532390 A JP 17532390A JP H0481469 A JPH0481469 A JP H0481469A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- phthalocyanine compound
- resin composition
- groups
- group
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 19
- -1 phthalocyanine compound Chemical class 0.000 claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- 239000010949 copper Substances 0.000 claims abstract description 7
- 239000010941 cobalt Chemical group 0.000 claims abstract description 6
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
- 125000000524 functional group Chemical group 0.000 claims abstract description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 5
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004018 acid anhydride group Chemical group 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000012776 electronic material Substances 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical group N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Parts Printed On Printed Circuit Boards (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Conductive Materials (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は電気・電子材料や導電性塗料などとして有用な
樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a resin composition useful as electrical/electronic materials, conductive paints, and the like.
（従来の技術）
従来より、フタロシアニン化合物は、光導電性を有する
ことが知られ、電子写真用有機感光体として工業的に利
用され、また光電変換用材料として利用する提案もなさ
れている。(Prior Art) Phthalocyanine compounds have been known to have photoconductivity and have been used industrially as organic photoreceptors for electrophotography, and proposals have also been made for their use as materials for photoelectric conversion.
しかし、フタロシアニン化合物の大多数は、遮光下では
絶縁体として挙動し、導電性を付与するためにヨウ素な
どの電子受容体でドーピング処理することか必要であっ
た。However, most phthalocyanine compounds behave as insulators when shielded from light, and require doping with an electron acceptor such as iodine to make them conductive.
また、例えば電気化学的手法により生成されるポリコバ
ルトフタロシアニンニトリド結晶（中面等、ケミストリ
ーレター、１９８５年、１６１７頁）のように、特別な
ドーパントを必要とせすに導電性を発現する化合物も報
告されている。しかし、この化合物は、不溶不動で昇華
性を有しないためフィルム等に成形することが困難であ
り、各種用途向けに芙用的でなかった。In addition, there are also compounds that exhibit electrical conductivity without requiring special dopants, such as polycobalt phthalocyanine nitride crystals (Nakamen et al., Chemistry Letters, 1985, p. 1617) produced by electrochemical methods. It has been reported. However, since this compound is insoluble and immobile and has no sublimation property, it is difficult to form it into a film or the like, and it has not been useful for various uses.
（発明が解決しようとする課題）
本発明は、従来技術が有する上記問題点を解決するもの
である。(Problems to be Solved by the Invention) The present invention solves the above-mentioned problems that the prior art has.
すなわち、本発明の目的は、特別なドーピング処理を行
わずとも高い導電性を示し、しかも容易に成形可能なフ
タロシアニン系導電性樹脂組成物を提供することにある
。That is, an object of the present invention is to provide a phthalocyanine-based conductive resin composition that exhibits high conductivity without special doping treatment and can be easily molded.
（課題を解決するための手段および作用）本発明者らは
、特定のフタロシアニン化合物が高い導電性を有し、し
かも該化合物を特定の樹脂と組み合せることにより、容
易に成形可能な樹脂組成物を形成し得ることを見い出し
、本発明を完成するに至った。(Means and Effects for Solving the Problems) The present inventors have developed a resin composition in which a specific phthalocyanine compound has high conductivity, and which can be easily molded by combining the compound with a specific resin. The present invention was completed based on the discovery that it is possible to form the following.
すなわち、本発明は、一般式（Ｉ）
（但し、式中のＭは銅またはコ／＜ルトを示す、）で示
されるフタロシアニン化合物（Ａ）およびフタロシアニ
ン化合物（Ａ）中のアミノ基と反応し得る官能基を有す
る樹脂（Ｂ）からなる導電性樹脂組成物に関する。That is, the present invention provides compounds that react with a phthalocyanine compound (A) represented by the general formula (I) (wherein M represents copper or copper) and an amino group in the phthalocyanine compound (A). The present invention relates to a conductive resin composition comprising a resin (B) having a functional group.
本発明で用いられるフタロシアニン化合Ｔｈ（Ａ）は、
前記一般式（Ｉ）で示されるものであり、例えば４．４
／ 、 ４ＬＬ 、 ４／＃−テトラアミノフタロシア
ニン銅や４．４’、４“ ４７′／−テトラアミノフタ
ロシアニンコバルトなどを挙げることができる。このフ
タロシアニン化合物（Ａ）自体は公知の物質であるが、
その導電性については報告されていない（例えばＪｏｕ
ｒｎａｌ ｏｆ ＧｅｎｅｒａｌＣｈｅｍｉ ５ｔ
ｒｙ、ＵＳＳＲ２４６巻、２０７５頁）。The phthalocyanine compound Th(A) used in the present invention is
It is represented by the general formula (I), for example 4.4
/, 4LL, 4/#-tetraaminophthalocyanine copper, 4.4', 4"47'/-tetraaminophthalocyanine cobalt, etc. This phthalocyanine compound (A) itself is a known substance,
Its conductivity has not been reported (e.g. Jou
rnal of GeneralChemi 5t
ry, USSR Vol. 246, p. 2075).
本発明者等は、種々のフタロシアニン化合物の導電性に
ついて検討した結果、フタロシアニン化合物（Ａ）が特
定のドーパントを添加せずども空気中・室温において固
有電導度にして１０’（ｓ／ ｃ ｍ ）程度の導電性
を有することを見出した。As a result of studying the conductivity of various phthalocyanine compounds, the present inventors found that the phthalocyanine compound (A) has a specific conductivity of 10' (s/cm) in air at room temperature without adding a specific dopant. It was found that it has a certain degree of conductivity.
また、導電性のレベルは、フタロシアニン化合物（Ａ＞
の中心金属の種類に依存し、中心金属が銅またはコバル
トの場合に高い導電性を有することも見出した。In addition, the level of conductivity is determined by the phthalocyanine compound (A>
It has also been found that depending on the type of the center metal, the conductivity is higher when the center metal is copper or cobalt.
よって、本発明で用いられるフタロシアニン化合物（Ａ
）は、分子中にアミノ基を有し且つ中心金属が銅または
コバルトでなければならない。Therefore, the phthalocyanine compound (A
) must have an amino group in the molecule and the central metal must be copper or cobalt.
本発明で用いられる樹脂（Ｂ）は、フタロシアニン化合
物（Ａ）中のアミノ基と反応し得る官能基を有する樹脂
であれば特に制限なく、例えば（メタ）アクリル酸を単
量体単位として含む重合体の如きカルボン酸基を含有す
る樹脂、無水マレイン酸を単量体単位として含む重合体
の如き酸無水物基を含有する樹脂、（メタ）アクリル酸
グリシジルを単量体単位として含む重合体の如きエポキ
シ基を含有する樹脂などを挙げることができる。The resin (B) used in the present invention is not particularly limited as long as it has a functional group that can react with the amino group in the phthalocyanine compound (A). Resins containing carboxylic acid groups such as polymers, resins containing acid anhydride groups such as polymers containing maleic anhydride as a monomer unit, and polymers containing glycidyl (meth)acrylate as a monomer unit. Examples include resins containing epoxy groups such as epoxy group-containing resins.
フタロシアニン化合物（Ａ）中のアミノ基と反応し得る
官能基を有しない樹脂を樹脂（Ｂ）の代わりに用いたの
では、フタロシアニン化合物（Ａ）との間で化学結合が
形成されず、高い導電性と成形した際の機械的強度に優
れた樹脂組成物か得られない。If a resin that does not have a functional group that can react with the amino group in the phthalocyanine compound (A) is used instead of the resin (B), no chemical bond will be formed with the phthalocyanine compound (A), resulting in high conductivity. However, a resin composition with excellent properties and mechanical strength when molded cannot be obtained.
樹脂（Ｂ）の中でも、フタロシアニン化合物（Ａ）との
反応性や成形性に特に優れていることから、スチレン−
無水マレイン酸共重合体やエチレン−無水マレイン酸共
重合体等のような単量体単位として無水マレイン酸を含
む重合体が好適に用いられる。Among the resins (B), styrene-
Polymers containing maleic anhydride as a monomer unit, such as maleic anhydride copolymers and ethylene-maleic anhydride copolymers, are preferably used.
本発明の樹脂組成物は、フタロシアニン化合物（Ａ＞お
よび樹脂（Ｂ）を含有していなければならない、フタロ
シアニン化合物（Ａ）を欠いた組成物では導電性が発現
しない。また、樹脂（Ｂ）を欠いた組成物では成形性が
低下して機械的強度に漫れた導電性薄膜が得られない、
たとえば、フタロシアニン化合物（Ａ）は、分子中にア
ミノ基を有するためＮ、Ｎ−ジメチルホルムアミドやジ
メチルスルホキシド等の極性溶媒に可溶であり、従って
、フタロシアニン化合Ｔｈ（Ａ）を含む溶液からキャス
ト法やスピンコード法等により導電性４膜を得ることも
できるが、このようにして得られる薄膜は機械的強度に
乏しく実用的でない。The resin composition of the present invention must contain a phthalocyanine compound (A) and a resin (B). A composition lacking the phthalocyanine compound (A) does not exhibit conductivity. A composition lacking this property will have poor moldability and will not be able to obtain a conductive thin film with good mechanical strength.
For example, since the phthalocyanine compound (A) has an amino group in its molecule, it is soluble in polar solvents such as N,N-dimethylformamide and dimethyl sulfoxide. Although it is also possible to obtain a conductive 4-layer film by a spin cord method or the like, the thin film obtained in this way has poor mechanical strength and is not practical.
本発明の樹脂組成物は、好適には塗膜やフィルムの形態
で使用される。このような塗膜やフィルムを形成するに
は、例えは本発明の樹脂組成物をＮ、Ｎ−ジメチルホル
ムアミドやジメチルスルホ（シト等の極性溶媒に混合溶
解した後、得られた溶液を溶液中のフタロシアニン化合
物（Ａ）と樹脂（Ｂ）とが反応しゲル化する以前にキャ
スト法やスピンコード法等の方法で基材に塗布し、室温
または必要により加熱条件下で乾燥硬化すれはよい。ま
た、塗膜を基材から剥離してフィルムとすることもでき
る。The resin composition of the present invention is preferably used in the form of a coating or film. In order to form such a coating or film, for example, the resin composition of the present invention is mixed and dissolved in a polar solvent such as N,N-dimethylformamide or dimethylsulfonate, and the resulting solution is mixed and dissolved in a solution. Before the phthalocyanine compound (A) and the resin (B) react to form a gel, it can be applied to a substrate by a method such as a casting method or a spin cord method, and then dried and cured at room temperature or, if necessary, under heating conditions. Moreover, the coating film can also be peeled off from the base material to form a film.
このようにして得られた塗膜やフィルムは、フタロシア
ニン化合物（Ａ）と樹脂（Ｂ）とが化学結合により一体
化しているため、上述の溶媒や濃硫酸等の薬品にも不溶
である。The coating film or film thus obtained is insoluble in the above-mentioned solvents and chemicals such as concentrated sulfuric acid, since the phthalocyanine compound (A) and the resin (B) are integrated by chemical bonds.
本発明の樹脂組成物は、フタロシアニン化合物（Ａ）の
含有量の増加とともに導電性が増大し、固有型導度にし
て１０’（ｓ／ｃｍ）程度の導電性を有するまでになる
。また、樹脂（Ｂ）の増加とともに、塗膜やフィルム状
に成形した導電性薄膜の機械的強度か次第に増大する。The conductivity of the resin composition of the present invention increases as the content of the phthalocyanine compound (A) increases, and the conductivity reaches an intrinsic conductivity of about 10' (s/cm). Furthermore, as the resin (B) increases, the mechanical strength of the conductive thin film formed into a coating or film gradually increases.
従って、本発明の樹脂組成物の使用にあたっては、種々
の用途において必要とされる導電性や機械的強度のレベ
ルに応じて、フタロシアニン化合物（Ａ）および樹脂（
Ｂ）の配合組成を選択するとよい。一般にフタロシアニ
ン化合物（Ａ＞および樹脂（Ｂ）の配合組成としては、
フタロシアニン化合物（Ａ）１０〜９０重１％、樹脂（
Ｂ）１０〜９０重量％の範囲が好ましい、フタロシアニ
ン化合物（Ａ）の配合量か１０重量％未満では充分な導
電性が得られないことかあり、また樹脂（Ｂ）の配合量
が１０重量％未満では実用上充分な機械的強度が得られ
ないことがある。Therefore, when using the resin composition of the present invention, the phthalocyanine compound (A) and the resin (
It is preferable to select the blending composition of B). Generally, the composition of the phthalocyanine compound (A> and resin (B)) is as follows:
Phthalocyanine compound (A) 10-90% by weight, resin (
B) The range of 10 to 90% by weight is preferable. If the amount of the phthalocyanine compound (A) is less than 10% by weight, sufficient conductivity may not be obtained, and the amount of the resin (B) is 10% by weight. If it is less than that, practically sufficient mechanical strength may not be obtained.
（発明の効果）
本発明の樹脂組成物は、特別なドーパントを必要とせす
に導電性を発現し、しかも強靭な塗膜やフィルム等に容
易に成形することができるため、電気・電子材料や導電
性塗料などとして有効に利用することができる。(Effects of the Invention) The resin composition of the present invention exhibits conductivity without the need for a special dopant, and can be easily formed into a tough coating film or film, so it can be used for electrical and electronic materials. It can be effectively used as a conductive paint.
（実施例）
次に本発明について実施例をあけてさらに説明するが、
本発明はこれたけに限定されるものではない。(Example) Next, the present invention will be further explained with reference to Examples.
The present invention is not limited to this.
なお、例中特にことわりのない限り、部は重量部を表わ
すものとする。In addition, unless otherwise specified in the examples, parts represent parts by weight.
実施例１
４．４’、４“、４″−テトラアミノフタロシアニンコ
バルト８部およびスチレン−無水マレイン酸共重合体（
モル比１：１）２部からなる本発明の樹脂組成物（１）
をジメチルスルホキシド９０部に混合溶解して得な溶液
をスピンコード法によりカラス基板上に塗布し、１６０
’Ｃで１５分間加熱することにより、厚さ１μｍの塗膜
を得た。この塗膜について、２ｆｌＡ子法による固有型
導度を測定した結果２．６Ｘ１０’（ｓ／ｃｍ）であっ
た。Example 1 8 parts of 4.4',4",4"-tetraaminophthalocyanine cobalt and styrene-maleic anhydride copolymer (
Resin composition (1) of the present invention consisting of 2 parts (molar ratio 1:1)
The resulting solution was mixed and dissolved in 90 parts of dimethyl sulfoxide, and the resulting solution was applied onto a glass substrate using a spin code method.
A coating film with a thickness of 1 μm was obtained by heating at C for 15 minutes. The intrinsic conductivity of this coating film was measured using the 2flA method and was found to be 2.6×10' (s/cm).
また、得られた塗膜の固有型導度の温度依存性を測定し
た結果、半導体的挙動を示し、活性化エネルギーΔは０
．２５ （ｅＶ）であることがわかった。In addition, as a result of measuring the temperature dependence of the intrinsic conductivity of the obtained coating film, it was found that it exhibited semiconductor-like behavior, and the activation energy Δ was 0.
．． 25 (eV).
実施例２〜７
実施例１で用いた樹脂組成物（１）の代わりに第１表に
示した配合組成の樹脂組成物（２）〜（７）のそれぞれ
を用いた以外は、実施例１と同様にして塗膜を形成し、
それらの固有型導度を測定した。その結果を第１表に示
した。Examples 2 to 7 Example 1 except that each of the resin compositions (2) to (7) having the formulation shown in Table 1 was used instead of the resin composition (1) used in Example 1. Form a coating film in the same manner as
Their intrinsic conductivities were measured. The results are shown in Table 1.
Claims (3)
れるフタロシアニン化合物（Ａ）およびフタロシアニン
化合物（Ａ）中のアミノ基と反応し得る官能基を有する
樹脂（Ｂ）からなる導電性樹脂組成物。1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, M in the formula represents copper or cobalt.) Reacts with the phthalocyanine compound (A) and the amino group in the phthalocyanine compound (A) A conductive resin composition comprising a resin (B) having a functional group that can be used.
ポキシ基からなる群より選ばれる少なくとも１種の官能
基を有する樹脂である請求項１記載の導電性樹脂組成物
。2. The conductive resin composition according to claim 1, wherein the resin (B) is a resin having at least one functional group selected from the group consisting of a carboxylic acid group, an acid anhydride group, and an epoxy group.
含む重合体である請求項１記載の導電性樹脂組成物。3. The conductive resin composition according to claim 1, wherein the resin (B) is a polymer containing maleic anhydride as a monomer unit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17532390A JPH0481469A (en) | 1990-07-04 | 1990-07-04 | Conductive resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17532390A JPH0481469A (en) | 1990-07-04 | 1990-07-04 | Conductive resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0481469A true JPH0481469A (en) | 1992-03-16 |
Family
ID=15994074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17532390A Pending JPH0481469A (en) | 1990-07-04 | 1990-07-04 | Conductive resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0481469A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5712332A (en) * | 1993-01-13 | 1998-01-27 | Nippon Shokubai Co. | Method for absorbing heat radiation |
| US6217394B1 (en) | 1999-01-13 | 2001-04-17 | Yazaki Corporation | Waterproof connector |
| US6322620B1 (en) | 2000-11-16 | 2001-11-27 | National Starch And Chemical Investment Holding Corporation | Conductive ink composition |
| JP2008052971A (en) * | 2006-08-23 | 2008-03-06 | Auto Network Gijutsu Kenkyusho:Kk | Waterproof connector |
| WO2014122959A1 (en) * | 2013-02-08 | 2014-08-14 | 富士フイルム株式会社 | Curable composition and color filter |
| US9512150B2 (en) | 2014-07-31 | 2016-12-06 | Empire Technology Development Llc | Thermal conductive compositions and methods for their preparation and use |
| US9917032B2 (en) | 2014-07-31 | 2018-03-13 | Empire Technology Development Llc | Conductive thermal compositions, uses thereof, and methods for their preparation |
-
1990
- 1990-07-04 JP JP17532390A patent/JPH0481469A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5712332A (en) * | 1993-01-13 | 1998-01-27 | Nippon Shokubai Co. | Method for absorbing heat radiation |
| US6217394B1 (en) | 1999-01-13 | 2001-04-17 | Yazaki Corporation | Waterproof connector |
| US6322620B1 (en) | 2000-11-16 | 2001-11-27 | National Starch And Chemical Investment Holding Corporation | Conductive ink composition |
| JP2008052971A (en) * | 2006-08-23 | 2008-03-06 | Auto Network Gijutsu Kenkyusho:Kk | Waterproof connector |
| WO2014122959A1 (en) * | 2013-02-08 | 2014-08-14 | 富士フイルム株式会社 | Curable composition and color filter |
| US10175573B2 (en) | 2013-02-08 | 2019-01-08 | Fujifilm Corporation | Curable composition and color filter |
| US9512150B2 (en) | 2014-07-31 | 2016-12-06 | Empire Technology Development Llc | Thermal conductive compositions and methods for their preparation and use |
| US9917032B2 (en) | 2014-07-31 | 2018-03-13 | Empire Technology Development Llc | Conductive thermal compositions, uses thereof, and methods for their preparation |
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