JPH03112990A - New boron complex salt - Google Patents
New boron complex saltInfo
- Publication number
- JPH03112990A JPH03112990A JP1249247A JP24924789A JPH03112990A JP H03112990 A JPH03112990 A JP H03112990A JP 1249247 A JP1249247 A JP 1249247A JP 24924789 A JP24924789 A JP 24924789A JP H03112990 A JPH03112990 A JP H03112990A
- Authority
- JP
- Japan
- Prior art keywords
- complex salt
- formula
- rubber
- substituted
- boron complex
- 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 title claims description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 229920001971 elastomer Polymers 0.000 abstract description 9
- 239000004033 plastic Substances 0.000 abstract description 9
- 229920003023 plastic Polymers 0.000 abstract description 9
- 239000005060 rubber Substances 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract description 4
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 abstract description 4
- 229960002510 mandelic acid Drugs 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 239000004014 plasticizer Substances 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- 239000012760 heat stabilizer Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- -1 n-octadecyl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003607 modifier Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910001411 inorganic cation Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000007976 iminium ions Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は新規なホウ素錯体塩に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to novel boron complex salts.
（従来の技術）
ホウ素錯体塩類は各種分野において多くの用途を有する
周知タイプの化合物である。例えば、ボロジサリチル酸
塩類が知られており、電解コンデンサ用電解質、高分子
改質剤、防腐剤などに応用されたり、検討されたりして
いる。BACKGROUND OF THE INVENTION Boron complex salts are a well-known type of compound that has many uses in a variety of fields. For example, borodisalicylates are known and are being applied or studied as electrolytes for electrolytic capacitors, polymer modifiers, preservatives, and the like.
この種の化合物の多（は化学的、熱的に安定で、また無
色であることから、特に、プラスチックおよびゴム等の
熱安定化剤、可塑剤等の高分子改質剤としての応用が今
後期待されている。また、最近では電子写真用のトナー
の電荷調整剤としても検討されている。Many of these compounds are chemically and thermally stable and colorless, so in the future they will be used as heat stabilizers for plastics and rubber, and as polymer modifiers for plasticizers. Recently, it has also been considered as a charge control agent for electrophotographic toners.
しかし、従来公知のホウ素錯体塩類は、典型的な溶剤に
溶解しがたく、プラスチックおよびゴムとの相溶性が不
十分で、高分子改質剤等の用途への使用には問題がある
。However, conventionally known boron complex salts are difficult to dissolve in typical solvents, have insufficient compatibility with plastics and rubber, and are problematic for use in applications such as polymer modifiers.
（発明が解決しようとする問題点）
本発明の目的は前記従来の技術的課題を背景になされた
もので、化学的、熱的に安定で溶剤溶解性に優れ、プラ
スチックあるいはゴムとの相溶性が高いホウ素錯体塩を
提供するものである。(Problems to be Solved by the Invention) The purpose of the present invention is to solve the above-mentioned conventional technical problems, and to solve the above-mentioned problems. This provides a boron complex salt with high
（問題点を解決するための手段）
すなわち、本発明は下記一般式（Ｉ）
・ ・ ・ （Ｉ）
（式中、Ｒ１およびＲ４は水素原子、アルキル基、置換
または非置換の芳香環（縮合環も含む）を示し、Ｒ２お
よびＲ３は置換または非置換の芳香環（縮合環も含む）
を示し、ＸｎＯはカチオンを示し、ｎは１または２であ
る。）で表される新規ホウ素錯体塩を提供するものであ
る。(Means for Solving the Problems) That is, the present invention has the following general formula (I) . R2 and R3 are substituted or unsubstituted aromatic rings (including fused rings)
, XnO represents a cation, and n is 1 or 2. ) A novel boron complex salt represented by:
一般式（Ｉ）で示される錯体塩について詳細に説明する
。アニオンのＲ１およびＲ４のアルキル基には、メチル
基、エチル基、ｎ−ブチル基、１ｓｏ−アミル基、ｎ−
ドデシル基、ｎ−オクタデシル基、シクロヘキシル基等
があげられ、Ｒ１、Ｒ２、Ｒ３およびＲ４の芳香環には
、ベンゼン環、ナフタリン環等があげられ、置換基には
アルキル基、アルコキシ基、ハロゲン原子、アリール基
、アラルキル基、ニトロ基、シアン基等があげられる。The complex salt represented by general formula (I) will be explained in detail. The alkyl groups of R1 and R4 of the anions include methyl group, ethyl group, n-butyl group, 1so-amyl group, n-
Examples include dodecyl group, n-octadecyl group, cyclohexyl group, etc., aromatic rings of R1, R2, R3 and R4 include benzene ring, naphthalene ring, etc., and substituents include alkyl group, alkoxy group, halogen atom. , aryl group, aralkyl group, nitro group, cyan group, etc.
カチオンには種々の無機カチオン、有機カチオンを用い
ることができる。無機カチオンには、水素イオン、金属
イオンがあげられ、１価および２価の金属イオンとして
、Ｌｉ十、Ｎａ十、Ｋ十、Ａ ｇ”、 Ｍｇ２十、
Ｃａ２＋、 Ｂ Ｒ２十、 Ｓ ｒ２＋、Ｐ ｂｚ
＋、 Ｍｎ２＋、 Ｃｏ２＋、 Ｎ ｉ ２＋、 Ｚ
ｎ２＋等があげられる。また有機カチオンとしては、種
々のアンモニウムイオン、イミニウムイオンまたはホス
ホニウムイオンなどがあげられる。Various inorganic cations and organic cations can be used as the cation. Inorganic cations include hydrogen ions and metal ions, and monovalent and divalent metal ions include Li+, Na+, K+, A<g>, Mg<20>,
Ca2+, BR20, S r2+, P bz
+, Mn2+, Co2+, N i 2+, Z
Examples include n2+. Examples of organic cations include various ammonium ions, iminium ions, and phosphonium ions.
本発明の一般式（Ｉ）で表される錯体塩は、例えば、ホ
ウ酸とアミンの水溶液に下記一般式（ｎ）（式中、Ｒ１
、Ｒ２は化合物（Ｉ）に同じ）で表されるマンデル酸ま
たはベンジル酸を加え反応さ易に得られる。The complex salt represented by the general formula (I) of the present invention can be prepared, for example, by adding the following general formula (n) to an aqueous solution of boric acid and an amine (where R1
, R2 is the same as that of compound (I)).
一般式（Ｉ）で示される錯体塩の具体例を下記に示す。Specific examples of the complex salt represented by general formula (I) are shown below.
なお下記Ｎｏ、は実施例中でも共通に用いる。Note that the following numbers are commonly used in the examples.
化合物Ｎｏ、 構 造 式化合物Ｎｏ。Compound No. Structure Compound No.
３
構
造
式
次に一般式（Ｉ）で表される錯体塩の諸性質について述
べる。本発明の錯体塩は総べて無色の化合物で、各植溶
剤、プラスチックまたはゴム等に相当量添加しても、そ
れらの本来の色を変化させることはない。熱的安定性は
通常のプラスチックまたはゴム等の成型、加工温度では
全く安定で、少くとも２００℃までは十分な耐性を示す
。また、溶剤溶解性は、通常の溶剤、例えばトルエン、
キシレン、塩化メチレン、クロロホルム、アセトン、ア
セトニトリル、Ｎ、Ｎ−ジメチルホルムアミド等に、一
般式ＣＩ）で表されるほとんどの錯体塩は２０％以上溶
解する。従来公知のボロジサリチル酸塩は無極性溶剤に
対する溶解性が低かったので、この点において従来のボ
ロジサリチル酸塩と相異する。3 Structural formula Next, various properties of the complex salt represented by general formula (I) will be described. The complex salts of the present invention are all colorless compounds, and even when added in a considerable amount to various solvents, plastics, rubbers, etc., their original colors do not change. Thermal stability is completely stable at the molding and processing temperatures of ordinary plastics or rubber, and shows sufficient resistance up to at least 200°C. In addition, solvent solubility is determined by using ordinary solvents such as toluene,
Most of the complex salts represented by the general formula CI) dissolve in xylene, methylene chloride, chloroform, acetone, acetonitrile, N,N-dimethylformamide, etc. at a concentration of 20% or more. Since conventionally known borodisalicylates have low solubility in nonpolar solvents, they differ from conventional borodisalicylates in this respect.
プラスチックまたはゴム類に対する相溶性は、例えばポ
リ塩化ビニル、ポリスチレン、ポリエステル、ポリアク
リル、ネオブレンゴム、クロロプレンゴム、シリコンゴ
ム等の添加剤としては十分な量である５％以上の相溶性
が認められる。The compatibility with plastics or rubbers is 5% or more, which is a sufficient amount as an additive for, for example, polyvinyl chloride, polystyrene, polyester, polyacrylic, neoprene rubber, chloroprene rubber, silicone rubber, etc.
さらに本発明の化合物は、従来公知のボロジサリチル酸
塩が高い水溶性を存していたのに比較して、水溶性が低
く、すなわち、耐水性が優れ、上記プラスチックまたは
ゴム類へ添加しても、その添加効果の湿度依存性がほと
んどない。同時に化学的にも安定で例えば通常の酸には
犯されない。Furthermore, the compound of the present invention has low water solubility, that is, excellent water resistance, compared to conventionally known borodisalicylates, which have high water solubility, and can be added to the above plastics or rubbers. Also, the effect of its addition has almost no humidity dependence. At the same time, it is chemically stable and is not attacked by ordinary acids, for example.
以上、本発明の錯体塩は耐熱性、相溶性、耐水性、化学
安定性に優れ、かつ、合成容易な比較的安価な錯体塩で
ある。As described above, the complex salt of the present invention is a relatively inexpensive complex salt that is excellent in heat resistance, compatibility, water resistance, and chemical stability, and is easy to synthesize.
本発明の錯体塩の用途としては、プラスチック、ゴム類
の改質剤、例えば、可塑剤、安定剤、酸化防止剤、紫外
線吸収剤、帯電防止剤、耐熱性向上剤等の他に、電子写
真用トナーの電荷調整剤、コンデンサ、電池等の電解質
、各種材料の表面処理剤、例えば、紫外線吸収剤、帯電
防止剤等がある。The complex salt of the present invention can be used as a modifier for plastics and rubbers, such as a plasticizer, a stabilizer, an antioxidant, an ultraviolet absorber, an antistatic agent, a heat resistance improver, etc. These include charge control agents for toners, electrolytes for capacitors and batteries, surface treatment agents for various materials, such as ultraviolet absorbers and antistatic agents.
（実 施 例） 以下、実施例により本発明を更に詳しく説明する。(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
化合物ＮＯ，２（ポロジマンデル酸亜鉛）の合成２モル
の１０重量％のアンモニア水に１モルの塩化亜鉛と２モ
ルのホウ酸を加えて溶解し、２モルのマンデル酸を加え
溶解する。２分後、更に２モルのマンデル酸を加え、混
合物を攪拌下、加熱する。反応終了後、冷却して白色ス
ラリーを濾過し、水洗後、白色ケーキを加熱乾燥して、
白色粉末状の化合物Ｎｏ、２を得る（収率８５％）。Example 1 Synthesis of compound NO,2 (zinc porodimandelate) Add 1 mol of zinc chloride and 2 mol of boric acid to 2 mol of 10% by weight ammonia water and dissolve, and then add and dissolve 2 mol of mandelic acid. . After 2 minutes, 2 more moles of mandelic acid are added and the mixture is heated with stirring. After the reaction is completed, the white slurry is cooled and filtered, washed with water, and the white cake is heated and dried.
A white powdery compound No. 2 is obtained (yield 85%).
この化合物の分解点は３４５℃であり、元素分析値は下
記の通りであった。The decomposition point of this compound was 345°C, and the elemental analysis values were as follows.
ＣＨ
計算値 ５７．７２ ３．６３
分析値 ５７．８５ ３．５８
実施例２
化合物Ｎｏ、４（ポロジベンジル酸ナトリウム）の合成
１モルのホウ酸を１モルの水酸化ナトリウムの１０重量
％水溶液に溶解して、１モルのベンジル酸を加え、溶解
する。２分後、更に１モルのベンジル酸を加え、混合物
を攪拌下、加熱する。反応終了後、冷却して白色スラリ
ーを濾過し、水洗後、白色ケーキを加熱乾燥して、白色
粉末状の化合物Ｎ００４を得る（収率９５％）。CH Calculated value 57.72 3.63 Analytical value 57.85 3.58 Example 2 Synthesis of compound No. 4 (sodium porodibenzilate) 1 mole of boric acid was dissolved in 1 mole of 10% by weight aqueous solution of sodium hydroxide. Then add 1 mol of benzylic acid and dissolve. After 2 minutes, a further 1 mol of benzylic acid is added and the mixture is heated with stirring. After the reaction is completed, the white slurry is cooled and filtered, washed with water, and the white cake is dried by heating to obtain a white powdery compound N004 (yield: 95%).
この化合物の分解点は３３４℃であり、元素分析値は下
記の通りであった。The decomposition point of this compound was 334°C, and the elemental analysis values were as follows.
ＣＨ
計算値 ７０．７３ ４．２４
分析値 ７０，６８ ４．２０
実施例３〜６
実施例１または実施例２と同様にして、相当するマンデ
ル酸またはベンジル酸より、第１表に示した化合物を得
た。CH Calculated value 70.73 4.24 Analytical value 70.68 4.20 Examples 3 to 6 Compounds shown in Table 1 were prepared from the corresponding mandelic acid or benzylic acid in the same manner as in Example 1 or Example 2. I got it.
第 １ 表 これらの化合物の分解点を第１表に示す。Table 1 The decomposition points of these compounds are shown in Table 1.
（発明の効果）
本発明により耐熱性、相溶性等に優れ、かつ無色である
新規ポロジベンジル酸塩およびポロジベンジル酸塩が得
られた。(Effects of the Invention) According to the present invention, novel porodibenzilates and porodibenzilates which have excellent heat resistance, compatibility, etc., and are colorless were obtained.
Claims (1)
置換または非置換の芳香環（縮合環も含む）を示し、Ｒ
＿２およびＲ＿３は置換または非置換の芳香環（縮合環
も含む）を示し、Ｘｎ■はカチオンを示し、ｎは１また
は２である。）で表される新規ホウ素錯体塩。[Claims] The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R_1 and R_4 are hydrogen atoms, alkyl groups,
Indicates a substituted or unsubstituted aromatic ring (including fused rings), R
_2 and R_3 represent substituted or unsubstituted aromatic rings (including fused rings), Xn■ represents a cation, and n is 1 or 2. ) A novel boron complex salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1249247A JPH03112990A (en) | 1989-09-27 | 1989-09-27 | New boron complex salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1249247A JPH03112990A (en) | 1989-09-27 | 1989-09-27 | New boron complex salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03112990A true JPH03112990A (en) | 1991-05-14 |
Family
ID=17190117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1249247A Pending JPH03112990A (en) | 1989-09-27 | 1989-09-27 | New boron complex salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03112990A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05224465A (en) * | 1992-02-14 | 1993-09-03 | Tomoegawa Paper Co Ltd | Electrophotographic dry developer |
| JPH06250442A (en) * | 1993-02-24 | 1994-09-09 | Ricoh Co Ltd | Developing method |
| US5804350A (en) * | 1997-03-04 | 1998-09-08 | Minolta Co., Ltd. | Negatively chargeable toner for developing electrostatic latent image |
| US5814428A (en) * | 1997-03-04 | 1998-09-29 | Minolta Co., Ltd. | Toner for developing electrostatic latent image |
| US5863692A (en) * | 1996-09-10 | 1999-01-26 | Minolta Co., Ltd. | Toner for elastrostatic latent image developing and method of manufacturing same |
| US5905011A (en) * | 1997-03-12 | 1999-05-18 | Minolta Co., Ltd. | Nonmagnetic monocomponent negatively chargeable color developer |
| US6025107A (en) * | 1997-10-29 | 2000-02-15 | Minolta Co., Ltd. | Negatively chargeable toner for developing electrostatic latent images |
| US6242147B1 (en) | 1997-09-03 | 2001-06-05 | Minolta Co., Ltd. | Negatively chargeable toner and developing device using thereof |
| JP2009276480A (en) * | 2008-05-14 | 2009-11-26 | Japan Carlit Co Ltd:The | Negatively chargeable charge control agent and toner comprising the same |
| JP2010215514A (en) * | 2009-03-13 | 2010-09-30 | Japan Carlit Co Ltd:The | Ion electroconductive agent, electroconductive resin composition comprising the same and electroconductive resin molded body |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02296254A (en) * | 1989-05-10 | 1990-12-06 | Ricoh Co Ltd | Dry developer for electrostatic latent image |
-
1989
- 1989-09-27 JP JP1249247A patent/JPH03112990A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02296254A (en) * | 1989-05-10 | 1990-12-06 | Ricoh Co Ltd | Dry developer for electrostatic latent image |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05224465A (en) * | 1992-02-14 | 1993-09-03 | Tomoegawa Paper Co Ltd | Electrophotographic dry developer |
| JPH06250442A (en) * | 1993-02-24 | 1994-09-09 | Ricoh Co Ltd | Developing method |
| US5863692A (en) * | 1996-09-10 | 1999-01-26 | Minolta Co., Ltd. | Toner for elastrostatic latent image developing and method of manufacturing same |
| US5804350A (en) * | 1997-03-04 | 1998-09-08 | Minolta Co., Ltd. | Negatively chargeable toner for developing electrostatic latent image |
| US5814428A (en) * | 1997-03-04 | 1998-09-29 | Minolta Co., Ltd. | Toner for developing electrostatic latent image |
| US5905011A (en) * | 1997-03-12 | 1999-05-18 | Minolta Co., Ltd. | Nonmagnetic monocomponent negatively chargeable color developer |
| US6242147B1 (en) | 1997-09-03 | 2001-06-05 | Minolta Co., Ltd. | Negatively chargeable toner and developing device using thereof |
| US6025107A (en) * | 1997-10-29 | 2000-02-15 | Minolta Co., Ltd. | Negatively chargeable toner for developing electrostatic latent images |
| JP2009276480A (en) * | 2008-05-14 | 2009-11-26 | Japan Carlit Co Ltd:The | Negatively chargeable charge control agent and toner comprising the same |
| JP2010215514A (en) * | 2009-03-13 | 2010-09-30 | Japan Carlit Co Ltd:The | Ion electroconductive agent, electroconductive resin composition comprising the same and electroconductive resin molded body |
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