JPH02110165A - Production of alpha-form copper phthalocyanine pigment - Google Patents
Production of alpha-form copper phthalocyanine pigmentInfo
- Publication number
- JPH02110165A JPH02110165A JP26276088A JP26276088A JPH02110165A JP H02110165 A JPH02110165 A JP H02110165A JP 26276088 A JP26276088 A JP 26276088A JP 26276088 A JP26276088 A JP 26276088A JP H02110165 A JPH02110165 A JP H02110165A
- Authority
- JP
- Japan
- Prior art keywords
- copper phthalocyanine
- water
- mixture
- crude copper
- sulfuric acid
- 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.)
- Granted
Links
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000000049 pigment Substances 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 238000010521 absorption reaction Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 11
- 239000011362 coarse particle Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000009837 dry grinding Methods 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 238000013019 agitation Methods 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000976 ink Substances 0.000 description 9
- 238000004040 coloring Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000007613 slurry method Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は印刷インキや塗料等の低粘度ベヒクル中に配合
したときに、α型銅フタロシアニンブルー顔料特有の鮮
明な赤味前の色調と高着色力を保ち、且つ極めて良好９
流動性を示す低吸油量のα型銅フタロシアニンブルー顔
料の製造方法に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention provides a clear pre-red color tone and high color tone characteristic of α-type copper phthalocyanine blue pigments when blended into low-viscosity vehicles such as printing inks and paints. Maintains coloring strength and is extremely good9
The present invention relates to a method for producing a low oil absorption α-type copper phthalocyanine blue pigment that exhibits fluidity.
（従来の技術）
従来、α型銅フタロシアニン顔料の製法としては、粗製
銅フタロシアニンを９５重量％以上の濃硫酸に溶解し、
これを多量の水中に注入して粒子を微細化するアシッド
ペースト法と、６０乃至８０重量％にｍ酸中で銅フタロ
シアニンの硫酸塩を形成させ、これを多量の水中に注入
して硫酸塩を加水分解して粒子を微細化するアシッドス
ラリー法が一般に行なわれている。(Prior art) Conventionally, the method for producing α-type copper phthalocyanine pigments involves dissolving crude copper phthalocyanine in 95% by weight or more concentrated sulfuric acid,
The acid paste method involves injecting this into a large amount of water to make the particles fine, and the other method involves forming a sulfate of copper phthalocyanine in 60 to 80% by weight m-acid and injecting this into a large amount of water to form a sulfate. An acid slurry method in which particles are refined by hydrolysis is generally used.
（発明が解決しようとしている問題点）前者のアシッド
ペースト法で得られる顔料粒子は極めて微細であり、色
調も鮮明で高着色力とすることが出来るが、この様にし
て得られた顔料は吸油量が大きく、印刷インキや塗料等
の低粘度ベヒクルに配合した場合に極めて高粘性を示し
良好な流動性は得られないという欠点がある。(Problem to be solved by the invention) The pigment particles obtained by the former acid paste method are extremely fine and can have a clear color tone and high tinting power, but the pigments obtained in this way do not absorb oil. It has the disadvantage that it is large in amount and exhibits extremely high viscosity when blended into low viscosity vehicles such as printing inks and paints, making it impossible to obtain good fluidity.
一方後者のアシッドスラリー法では、形成される粒子は
アシッドペースト法に比べ著しく粗大粒子となり、低粘
度ベヒクルに配合した場合に低粘性を示し良好な流動性
を示すが色調が不鮮明になり着色力が極端に低下すると
いう欠点がある。On the other hand, in the latter acid slurry method, the particles formed are significantly coarser than those in the acid paste method, and when blended in a low viscosity vehicle, they exhibit low viscosity and good fluidity, but the color tone becomes unclear and the coloring power decreases. It has the disadvantage of being extremely low.
−］二記の如き従来技術によるα型銅フタロシアニン顔
料は、いずれにしても夫々欠点かあり印刷インキや塗料
等低活性で流動性を求められる用途に対しては不適であ
り、その改良が求められてい従って本発明の目的は、α
型銅フタロシアニン顔料特有の鮮明な赤味青色と高い着
色力とを保持し、印刷インキや塗料等の低粘度ベヒクル
中に配合した場合にも十分な低粘性と極めて良好な流動
性を示すα型銅フタロシアニン顔料を提供することであ
る。-] The α-type copper phthalocyanine pigments according to the prior art as described in 2 have their own drawbacks and are unsuitable for applications that require low activity and fluidity, such as printing inks and paints, and improvements are needed. Therefore, the object of the present invention is to
α-type retains the vivid reddish-blue color and high coloring power characteristic of copper phthalocyanine pigments, and exhibits sufficiently low viscosity and extremely good fluidity even when blended into low-viscosity vehicles such as printing inks and paints. An object of the present invention is to provide a copper phthalocyanine pigment.
（問題点を解決するための手段） 上記目的は以下の本発明によりて達成される。(Means for solving problems) The above object is achieved by the present invention as described below.
すなわち、本発明は、粗製銅フタロシアニンを、ＴＡ＠
酸、水及び有機溶剤（アルコール及び／又はセロソルブ
）の３成分からなる混合液中で加熱攪拌した後、多量の
水中に注入し混合液を除去することを特徴とする低吸油
量且つ微細なα型銅フタロシアニン顔料の製造方法であ
る。That is, the present invention converts crude copper phthalocyanine into TA@
A low-oil-absorbing and fine-grained α that is characterized by heating and stirring in a mixture of three components: acid, water, and organic solvent (alcohol and/or cellosolve), then pouring it into a large amount of water and removing the mixture. This is a method for producing a type copper phthalocyanine pigment.
（好ましい実施態様）
次に好ましい実施態様を挙げて本発明を更に詳しく説明
する。(Preferred Embodiments) Next, the present invention will be described in more detail by citing preferred embodiments.
本発明で使用する粗製銅フタロシアニンは従来公知の方
法で合成したままの粗大粒子の粗製銅フタロシアニンで
もよいし、又、これらの粗大粒子の粗製銅フタロシアニ
ンをボールミル、振動ミル、乾式アトライター等の磨砕
機により乾式磨砕して得られる粗製銅フタロシアニンで
あってもよく特に限定されないが、特に好適なものは１
分子中に１乃至３個の塩素原子を含む低塩素化銅フタロ
シアニンである。The crude copper phthalocyanine used in the present invention may be the crude copper phthalocyanine in the form of coarse particles synthesized by a conventionally known method, or the crude copper phthalocyanine in the form of coarse particles may be polished using a ball mill, vibration mill, dry attritor, etc. Crude copper phthalocyanine obtained by dry grinding using a crusher may be used, but is not particularly limited, but particularly preferred is 1.
It is a low chlorinated copper phthalocyanine containing 1 to 3 chlorine atoms in the molecule.
本発明で使用する混合液は、硫酸−水一有機溶剤（アル
コール及び／又はセロソルブ）の３成分系混合液であり
、該混合液の硫酸の濃度は一般的には６０乃至８０重量
％の範囲であり、好ましくは６５乃至７０重量％の範囲
である。The liquid mixture used in the present invention is a three-component liquid mixture of sulfuric acid, water, and organic solvent (alcohol and/or cellosolve), and the concentration of sulfuric acid in the liquid mixture is generally in the range of 60 to 80% by weight. and is preferably in the range of 65 to 70% by weight.
又、上記混合液の有機溶剤の濃度は一般的には０．５乃
至３０重量％の範囲であり、好ましくは３乃至１５重量
％の範囲である。Further, the concentration of the organic solvent in the above-mentioned liquid mixture is generally in the range of 0.5 to 30% by weight, preferably in the range of 3 to 15% by weight.
上記有機溶剤として使用するアルコールとしては、メタ
ノール、エタノール、プロピルアルコール、イソプロピ
ルアルコール、ブタノール、イソブタノール等低級易水
溶性のアルコールが好ましく、セロソルブとしては、メ
チルセロソルブ、エチルセロソルブ、ブチルセロソルブ
等易水溶性のセロソルブか好ましく、これらのアルコー
ル及びセロソルブは単独若しくは混合して使用すること
が出来る。The alcohol used as the organic solvent is preferably a lower easily water-soluble alcohol such as methanol, ethanol, propyl alcohol, isopropyl alcohol, butanol or isobutanol. Cellosolve is preferred, and these alcohols and cellosolve can be used alone or in combination.
上記混合液の使用量は使用する粗製銅フタロシアニンの
５乃至１５重量倍でよく、加熱温度は１０乃至８０℃の
範囲で、好ましくは３５乃至４５℃の範囲であり、加熱
熱時間は０．５乃至８時間の範囲で、好ましくは３乃至
４時間の範囲である。The amount of the mixed liquid used may be 5 to 15 times the weight of the crude copper phthalocyanine used, the heating temperature is in the range of 10 to 80°C, preferably 35 to 45°C, and the heating time is 0.5 The time range is from 8 hours to 8 hours, preferably from 3 to 4 hours.
（実施例）
以下実施例及び比較例を挙げて本発明を更に具体的に説
明する。(Example) The present invention will be explained in more detail below by giving Examples and Comparative Examples.
実施例１
９８％濃硫酸２，６２６ｇ及び水１，１４６ｇを混合し
、この中にメタノール６４ｇ及びブチルセロソルブ６４
ｇを加えて硫酸濃度６６重量％の混合液を作成する。温
度を４５℃に設定して粗製銅フタロシアニン２６０ｇを
加え、この温度で４時間攪拌した後、１５，０００ｇの
水へ攪拌下注入する。１５分間攪拌後、１１過、水洗及
び乾燥してα型銅フタロシアニン顔料２５０ｇを得た。Example 1 2,626 g of 98% concentrated sulfuric acid and 1,146 g of water were mixed, and 64 g of methanol and 64 g of butyl cellosolve were mixed therein.
g to create a mixed solution with a sulfuric acid concentration of 66% by weight. The temperature is set at 45° C. and 260 g of crude copper phthalocyanine are added, stirred at this temperature for 4 hours and then poured into 15,000 g of water with stirring. After stirring for 15 minutes, the mixture was filtered for 11 minutes, washed with water, and dried to obtain 250 g of α-type copper phthalocyanine pigment.
実施例２
９８％１１Ａ硫酸２，７２９ｇ及び水１，０５８ｇを混
合し、この中にメタノール２６３ｇを加え、硫酸濃度６
６重量％の混合液を作成する。温度を４０℃に設定して
、この中に乾式磨砕した粗製銅フタロシアニン（５２乾
式アトライター中て合成直後の粗製銅フタロシアニン５
００ｇを３０分分間式磨砕したもの）：２２５ｇを加え
、この温度で３時間攪拌した後、１５，０００ｇの水中
へ攪拌上注入する。１５分間攪拌後濾過、水洗及び乾燥
してα型銅フタロシアニン顔料２１６ｇを得た。Example 2 2,729 g of 98% 11A sulfuric acid and 1,058 g of water were mixed, 263 g of methanol was added thereto, and the sulfuric acid concentration was 6.
A 6% by weight mixed solution is prepared. The temperature was set at 40°C, and the dry-milled crude copper phthalocyanine (52 crude copper phthalocyanine immediately after synthesis in the dry attritor) was placed in the dry-milled crude copper phthalocyanine 5.
00g (milled for 30 minutes): 225g was added, stirred at this temperature for 3 hours, and then poured into 15,000g of water with stirring. After stirring for 15 minutes, the mixture was filtered, washed with water, and dried to obtain 216 g of α-type copper phthalocyanine pigment.
比較例１（アシッドペースト法）
９８％濃硫酸２，６００ｇ中へ粗製銅フタロシアニン２
６０ｇを加え６０℃で２時間攪拌して粗製銅フタロシア
ニンを硫酸に完全に溶解した後、１５．０００ｇの水中
へ攪拌上注入する。１５分間攪拌後濾過、水洗及び９′
ｉ、燥してα型銅フタロシアニン顔料２５０ｇを得た。Comparative Example 1 (Acid Paste Method) Crude copper phthalocyanine 2 was added to 2,600 g of 98% concentrated sulfuric acid.
After adding 60 g and stirring at 60° C. for 2 hours to completely dissolve the crude copper phthalocyanine in sulfuric acid, it was poured into 15.000 g of water with stirring. After stirring for 15 minutes, filtration, washing with water and 9'
i. Drying yielded 250 g of α-type copper phthalocyanine pigment.
比較例２（アシッドスラリー法）
９８％硫酸３，１０５ｇ及び水７９６ｇを混合して７８
重１％濃度の硫酸を作成する。温度を４０℃に設定して
粗製銅フタロシアニン２６０ｇを加え、この温度で４時
間攪拌した後、１５，０００ｇの水中へ攪拌上注入する
。１５分間攪拌後濾過、水洗及び乾燥してα型銅フタロ
シアニン顔料２５０ｇを得た。Comparative Example 2 (Acid Slurry Method) 3,105g of 98% sulfuric acid and 796g of water were mixed to make 78%
Prepare sulfuric acid with a concentration of 1% by weight. The temperature was set at 40° C., 260 g of crude copper phthalocyanine was added, the mixture was stirred at this temperature for 4 hours, and then poured into 15,000 g of water with stirring. After stirring for 15 minutes, the mixture was filtered, washed with water, and dried to obtain 250 g of α-type copper phthalocyanine pigment.
上記実施例及び比較例により得た顔料の比較試験結果
（イ）顔料分散物の作成
ベヒクル（変性アマニ油） ５０ｆｆｌｆｆ１部
顔料 １０重量部上記配合で
小型３本ロールで練肉し、顔料をベヒクル中に完全に分
散させてインキを作り試料とする。Comparative test results for pigments obtained in the above Examples and Comparative Examples (a) Preparation of pigment dispersion Vehicle (modified linseed oil) 50fflff 1 part Pigment 10 parts by weight The above formulation was kneaded using three small rolls, and the pigment was mixed into the vehicle. Completely disperse the ink to make ink and use it as a sample.
（ロ）流動性の測定
上記（イ）で得られた試料５ｇをガラス板上にとり、そ
れを６０度角に傾斜させて２時間後の試料の流下距離を
測定する。(b) Measurement of fluidity Take 5 g of the sample obtained in (a) above on a glass plate, tilt it at an angle of 60 degrees, and measure the flow distance of the sample after 2 hours.
（八）色 相
上記（イ）で得られた試料の印刷物の測定結果主波長二
色相 純度：鮮明度
（ニ）着色力
上記（イ）で得られた比較例１の試料ｔｇと白色インキ
Ｌｏｇとを混合した場合の着色濃度を基準として、各試
料１ｇを夫々白インキと混合し、比較例１と同一着色濃
度になる迄の白インキの使用量で判定する。(8) Hue Measurement results of the printed matter of the sample obtained in (a) above Dominant wavelength Two hues Purity: Visibility (d) Coloring power Sample tg of Comparative Example 1 obtained in (a) above and white ink Log 1 g of each sample was mixed with white ink, and the amount of white ink used until the same coloring density as Comparative Example 1 was obtained was determined based on the coloring density when mixed with.
（効 果）
試験結果が示す通り本発明によるものは、従来技術によ
るものに比べ、色相及び着色力をさほど損なうことなく
極めて良好な流動性が得られることか判明した。(Effect) As shown by the test results, it was found that the product according to the present invention provides extremely good fluidity without significantly impairing the hue and tinting power compared to the product according to the prior art.
特許出願人 大目特化工業株式会社 （試験結果） 実施例１ 実施例２ 比較例１ 比較例２ １５．１ １４．６ ３．３ １６．６ ４８３．１ ４８２．０ ４８＋ 、３ ４８４．６ ８０．９ ８１．７ ８ｚ、８ ７９．６Patent applicant: Daimoku Specialty Industry Co., Ltd. (Test results) Example 1 Example 2 Comparative example 1 Comparative example 2 15.1 14.6 3.3 16.6 483.1 482.0 48+, 3 484.6 80.9 81.7 8z, 8 79.6
Claims (7)
剤（アルコール及び／又はセロソルブ）の３成分からな
る混合液中で加熱攪拌した後、多量の水中に注入し混合
液を除去することを特徴とする低吸油量且つ微細なα型
銅フタロシアニン顔料の製造方法。(1) Crude copper phthalocyanine is heated and stirred in a mixture of three components: concentrated sulfuric acid, water, and an organic solvent (alcohol and/or cellosolve), then poured into a large amount of water and the mixture is removed. A method for producing a low oil absorption and fine α-type copper phthalocyanine pigment.
の粗製銅フタロシアニンである請求項１に記載の製造方
法。(2) The production method according to claim 1, wherein the crude copper phthalocyanine is crude copper phthalocyanine in the form of coarse particles as synthesized.
をボールミル、振動ミル、乾式アトライター等の磨砕機
により乾式磨砕して得られるものである請求項１に記載
の製造方法。(3) The manufacturing method according to claim 1, wherein the crude copper phthalocyanine is obtained by dry grinding coarse particles as synthesized using a grinding machine such as a ball mill, a vibration mill, or a dry attritor.
塩素原子を含む低塩素化銅フタロシアニンである請求項
１に記載の製造方法。(4) The production method according to claim 1, wherein the crude copper phthalocyanine is a low chlorinated copper phthalocyanine containing 1 to 3 chlorine atoms in one molecule.
請求項１に記載の製造方法。(5) The manufacturing method according to claim 1, wherein the sulfuric acid concentration in the mixed liquid is 60 to 80% by weight.
１に記載の製造方法。(6) The manufacturing method according to claim 1, wherein the heating temperature is in the range of 10°C to 80°C.
１に記載の製造方法。(7) The manufacturing method according to claim 1, wherein the stirring time is in the range of 0.5 to 8 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63262760A JPH0643564B2 (en) | 1988-10-20 | 1988-10-20 | Method for producing α-type copper phthalocyanine pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63262760A JPH0643564B2 (en) | 1988-10-20 | 1988-10-20 | Method for producing α-type copper phthalocyanine pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02110165A true JPH02110165A (en) | 1990-04-23 |
| JPH0643564B2 JPH0643564B2 (en) | 1994-06-08 |
Family
ID=17380208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63262760A Expired - Fee Related JPH0643564B2 (en) | 1988-10-20 | 1988-10-20 | Method for producing α-type copper phthalocyanine pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643564B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6926913B2 (en) * | 2017-10-03 | 2021-08-25 | 東洋インキＳｃホールディングス株式会社 | Pigment composition for color filter, coloring composition for color filter and color filter |
-
1988
- 1988-10-20 JP JP63262760A patent/JPH0643564B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0643564B2 (en) | 1994-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |