JP2899093B2 - Underwater organism adhesion inhibitor - Google Patents
Underwater organism adhesion inhibitorInfo
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- JP2899093B2 JP2899093B2 JP25191290A JP25191290A JP2899093B2 JP 2899093 B2 JP2899093 B2 JP 2899093B2 JP 25191290 A JP25191290 A JP 25191290A JP 25191290 A JP25191290 A JP 25191290A JP 2899093 B2 JP2899093 B2 JP 2899093B2
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- compound
- isopropyl
- maleimide
- formula
- underwater
- Prior art date
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Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、船底防汚塗料、魚網防汚剤、ブイ、水路、
水中構築物などとして用いる水中生物付着防止剤に関す
るものである。The present invention relates to antifouling paints for ship bottoms, antifouling agents for fish nets, buoys, waterways,
The present invention relates to an underwater organism adhesion inhibitor used as an underwater structure.
（従来の技術） 従来、船舶の船底部、魚網、ブイ、水路及び水中構築
物などの水中生物付着防止剤として、例えば特公昭61−
15843号公報においては、３′−メチルまたは３′−ト
リフルオロメチル−ベンズアニリド類を用いることが提
案されている。しかし、タテジマフジツボのキープリウ
ス幼生に対する本発明者らの追試によれば上記ベンズア
ニリド類は水中生物付着防止活性がまだ十分ではないこ
とが確認された。(Prior Art) Conventionally, as an underwater biofouling inhibitor for the bottom of ships, fish nets, buoys, waterways and underwater structures, for example,
15843 proposes to use 3'-methyl or 3'-trifluoromethyl-benzanilides. However, our follow-up tests on the larvae of keyprius of the barnacle found that the benzanilides did not yet have sufficient anti-biological adhesion activity in water.
また、特開昭59−167504号公報において３′−アルコ
キシ−ベンズアニリド類と置換フェニルマレイミド類と
の併用剤を用いる方法が提案されている。この方法は、
ある程度の防汚効果は期待されるものの、塗料中で有効
成分が、粒度成長する（以下再結という）という難点が
ある。通常、塗料は調製後、運搬、販売、保存、使用等
に時間がかかることが多く長期の保存に耐えるものでな
ければならない。このような塗料中の再結は、塗装作業
に支障をきたしたり、均一に塗装することを困難にす
る。従って薬剤の溶出が制御できず、生物付着防止効果
を大きく低下させる問題点を有していた。Also, Japanese Patent Application Laid-Open No. 59-167504 proposes a method using a combination agent of 3'-alkoxy-benzanilides and substituted phenylmaleimides. This method
Although a certain antifouling effect is expected, there is a drawback that the active ingredient in the paint grows in particle size (hereinafter referred to as re-solidification). Usually, after preparation, it takes a long time to transport, sell, store, use, etc., and the coating must endure long-term storage. Such recombination in the paint hinders the painting operation and makes it difficult to paint uniformly. Therefore, there was a problem that the dissolution of the drug could not be controlled, and the effect of preventing biofouling was greatly reduced.
（発明が解決しようとする課題） 本発明は、ベンズアニリド化合物の中より優れた防汚
性能を発揮し、実用性の高い貝類付着防止剤または水中
生物付着防止剤を提供しようとするものである。(Problems to be Solved by the Invention) The present invention aims to provide a highly practical shellfish adhesion inhibitor or aquatic organism adhesion inhibitor that exhibits more excellent antifouling performance than the benzanilide compound.
（課題を解決するための手段） 本発明者は、ベンズアニリド化合物の中より、貝類付
着防止に優れた防止性能を発揮し得る化合物について種
々の研究を重ねたところ、特定の３′−イソプロピル−
ベンズアニリド化合物がタテジマフジツボに対し高い活
性を有することを見出した。(Means for Solving the Problems) The present inventor has conducted various studies on compounds that can exhibit excellent prevention performance against shellfish adhesion among benzanilide compounds, and found that a specific 3′-isopropyl-
The benzanilide compounds have been found to have high activity against barnacles.
さらにこの化合物と、特定のマレイミド化合物などを
併用することにより、水中生物の付着に対しより高い付
着防止効果を発揮することを見い出し、この知見に基づ
き本発明を完成した。Furthermore, they have found that by using this compound in combination with a specific maleimide compound or the like, a higher adhesion-preventing effect against the adhesion of aquatic organisms has been achieved, and the present invention has been completed based on this finding.
すなわち本発明は、 （１）式 （式中、Ｒはメチル基、トリフルオロメチル基を示
す。） で表される３′−イソプロピル−ベンズアニリド化合物
を有効成分とする貝類付着防止剤であり、 （２）（イ）上記（１）項記載の式（Ｉ）で表される
３′−イソプロピル−ベンズアニリド化合物より選ばれ
る少なくとも１種と、 （ロ）Ｎ−（２′,4′,6′−トリクロロフェニル）マレ
イミド、2,3−ジクロロ−Ｎ−（２′,6′−ジエチルフ
ェニル）マレイミド、2,3−ジクロロ−Ｎ−（２′−メ
チル−６′−エチルフェニル）マレイミド、テトラメチ
ルチウラムジスルフィド及びテトラエチルチウラムジス
ルフィドより選ばれる少なくとも１種とを有効成分とし
て含有することを特徴とする水中生物付着防止剤を提供
するものである。That is, the present invention provides: (Wherein, R represents a methyl group or a trifluoromethyl group). A shellfish adhesion inhibitor containing a 3′-isopropyl-benzanilide compound represented by the following formula (2). And at least one selected from 3'-isopropyl-benzanilide compounds represented by the formula (I) described in (1), and (b) N- (2 ', 4', 6'-trichlorophenyl) maleimide, 2,3- At least one selected from dichloro-N- (2 ', 6'-diethylphenyl) maleimide, 2,3-dichloro-N- (2'-methyl-6'-ethylphenyl) maleimide, tetramethylthiuram disulfide and tetraethylthiuram disulfide An object of the present invention is to provide an underwater biofouling inhibitor characterized by containing one kind as an active ingredient.
本発明の式（Ｉ）の３′−イソプロピル−ベンズアニ
リド化合物は、３′−イソプロピル−２−メチルベンズ
アニリド、３′−イソプロピル−２−トリフルオロメチ
ルベンズアニリドである。The 3'-isopropyl-benzanilide compound of the formula (I) of the present invention is 3'-isopropyl-2-methylbenzanilide, 3'-isopropyl-2-trifluoromethylbenzanilide.
なお本発明の水中生物付着防汚剤の実施態様は特に制
限は無く、適宜、塗料、乳剤、水和剤として使用され
る。例えば、本発明の水中生物付着防止剤を塗膜形成剤
に配合して防汚塗料に調製し、これを船底、水中構築
物、あるいは冷却用水取り入れ路壁などに塗布すること
によって水中生物の付着繁殖を防止することができる。
この際、塗膜形成剤としては慣用のもの例えば、油ワニ
ス、合成樹脂、合成ゴム、ロジンなどが用いられる。さ
らに顔料などを使用しても差し支え無い。また防汚塗料
を調製する場合は、式（Ｉ）の化合物は塗膜が形成でき
る限りにおいて濃度に上限はないが防汚塗料に対し、１
〜30重量％、好ましくは10〜20重量％の割合で配合す
る。また（イ）の式（Ｉ）の化合物と（ロ）の化合物よ
りそれぞれ混合して用いる場合は、式（Ｉ）の化合物を
１〜30重量％の割合、好ましくは５〜20重量％の割合で
配合する。また（ロ）の化合物を５〜30重量％の割合、
好ましくは10〜20重量％の割合で配合することができ
る。また冷却用水の取水路における水中生物の付着繁殖
を防止する目的では、本発明の水中生物付着防止剤を溶
液、または乳剤の形で取水路の中へ添加してもよい。溶
液として使用する場合は、 ｉ）式（Ｉ）の３′−イソプロピル−ベンズアニリド化
合物より選択して用いるが、ii）または（イ）の式
（Ｉ）の化合物より選ばれる少なくとも１種と、（ロ）
より選ばれる少なくとも１種を併用し、さらに塗膜形成
剤を配合して溶媒に溶解した溶液とする。これを水中生
物の付着繁殖を防止する目的で繁殖用魚網、定置用魚網
などへ塗布することができる。長期間防汚効果を持続さ
せるには、塗料の形で適用するのが望ましい。また溶媒
としては、本発明の化合物が溶け易い芳香族炭化水素溶
媒が用いられる。例えばトルエン、キシレン、クメン、
ナフサなどを使用するが、必要によりアルコール類、ケ
トン類などを用いても差し支え無い。可塑剤としては、
例えばジオクチルフタレート（DOP）、塩素化パラフィ
ンなどや着色のため、着色顔料、体質顔料を加えても差
し支え無い。またさらに防汚期間の延長のため、亜酸化
銅を混合しても差し支え無い。The embodiment of the antifouling agent for biofouling in water of the present invention is not particularly limited, and is suitably used as a paint, an emulsion or a wettable powder. For example, the underwater organism adhesion inhibitor of the present invention is mixed with a film-forming agent to prepare an antifouling paint, which is then applied to the bottom of a ship, an underwater structure, or a cooling water intake road wall to thereby attach and propagate an underwater organism. Can be prevented.
At this time, as the coating film forming agent, a conventional one such as oil varnish, synthetic resin, synthetic rubber, rosin and the like are used. Further, pigments or the like may be used. When an antifouling paint is prepared, the concentration of the compound of formula (I) has no upper limit as long as a coating film can be formed.
-30% by weight, preferably 10-20% by weight. When each of the compound of the formula (I) and the compound of the formula (I) is mixed and used, the compound of the formula (I) is used in a proportion of 1 to 30% by weight, preferably 5 to 20% by weight. Mix in. A compound of (b) in a ratio of 5 to 30% by weight;
Preferably, it can be blended at a ratio of 10 to 20% by weight. Further, for the purpose of preventing the adhesion and propagation of aquatic organisms in the cooling water intake channel, the underwater organism adhesion inhibitor of the present invention may be added to the intake channel in the form of a solution or an emulsion. When used as a solution, i) is selected from the 3'-isopropyl-benzanilide compounds of the formula (I), and ii) or at least one selected from the compounds of the formula (I) of (a); B)
At least one selected from the above is used in combination, and a film forming agent is further blended to form a solution dissolved in a solvent. It can be applied to breeding fish nets, stationary fish nets, etc. for the purpose of preventing the adherent propagation of aquatic organisms. In order to maintain the antifouling effect for a long time, it is desirable to apply the composition in the form of a paint. As the solvent, an aromatic hydrocarbon solvent in which the compound of the present invention is easily soluble is used. For example, toluene, xylene, cumene,
Naphtha or the like is used, but alcohols and ketones may be used if necessary. As a plasticizer,
For example, dioctyl phthalate (DOP), chlorinated paraffin, or the like, or a coloring pigment or extender for coloring may be added. In order to further extend the antifouling period, cuprous oxide may be mixed.
（発明の効果） 本発明の水中生物付着防止剤は、水中生物に対し幅広
いスペクトルと高い付着防止効果を示す。さらに本発明
の水中生物付着防止剤は塗料として調製した場合に再結
することなく安定であり、防汚性能を十分に発揮する。(Effect of the Invention) The anti-adhesion agent for aquatic organisms of the present invention exhibits a broad spectrum and a high anti-adhesion effect to aquatic organisms. Furthermore, the anti-biological-in-water agent of the present invention is stable without recombination when it is prepared as a paint, and exhibits sufficient antifouling performance.
（実施例） 以下実施例により、本発明を詳細に説明する。なお、
実施例、比較例に示される％は重量％を示す。(Examples) Hereinafter, the present invention will be described in detail with reference to examples. In addition,
The percentages shown in Examples and Comparative Examples indicate weight percentages.
使用する化合物は以下の通りである。 The compounds used are as follows.
１）イ）本発明の３′−イソプロピル−ベンズアニリド
化合物 〔化合物１〕 ３′−イソプロピル−２−メチルベンズアニリド 〔化合物２〕 ３′−イソプロピル−２−トリフルオロメチルベンズア
ニリド ２）比較化合物 〔化合物３〕（特公昭61−15843号特許請求の範囲に含
まれる化合物） ３′−メチル−２−メチルベンズアニリド 〔化合物４〕（特公昭61−15843号記載の化合物） ３′−メチル−２−トリフルオロメチルベンズアニリド 〔化合物５〕（特開昭59−167504号記載の化合物） ３′−イソプロポキシ−２−メチルベンズアニリド ３）ロ）群より選んだ化合物 〔化合物６〕 Ｎ−（２′,4′,6′−トリクロロフェニル）マレイミド 〔化合物７〕 2,3−ジクロロ−Ｎ−（２′,6′−ジエチルフェニル）
マレイミド 〔化合物８〕 テトラメチルチウラムジスルフィド 実施例１ 人工海水中でふ化したタテジマフジツボのノープリウ
ス幼生を、ケイ藻を飼料として付着期幼生であるキープ
リウス幼生へ馴養し供試生物とした。この幼生10個体を
含む人工海水19mlを直径5cmのシャーレに移した。供試
化合物10mgをシクロヘキサンと界面活性剤ツイーン−80
（Tween−80;アトラスパウダー社製）とが10:1からなる
乳化液で1gの乳剤として、人工海水で所定の濃度に希釈
する。この1mlを上記試験用シャーレに添加した。シャ
ーレは20℃恒温室へ静置し、24時間後の死亡個数を調
べ、この試験を３回繰り返し半数致死濃度（以下LC50を
示す。）を求めた。その結果を表１に示す。1) a) 3'-isopropyl-benzanilide compound of the present invention [Compound 1] 3'-isopropyl-2-methylbenzanilide [Compound 2] 3'-isopropyl-2-trifluoromethylbenzanilide 2) Comparative compound [Compound 3] (compound included in the claims of JP-B-61-15843) 3'-methyl-2-methylbenzanilide [Compound 4] (compound described in JP-B-61-15843) 3'-methyl-2- Trifluoromethylbenzanilide [Compound 5] (compound described in JP-A-59-167504) 3'-Isopropoxy-2-methylbenzanilide 3) A compound selected from the group 3) [Compound 6] N- (2 ' , 4 ', 6'-Trichlorophenyl) maleimide [Compound 7] 2,3-dichloro-N- (2', 6'-diethylphenyl)
Maleimide [Compound 8] Tetramethylthiuram disulfide Example 1 Naprius larvae of hatchlea barnacles hatched in artificial seawater were acclimated to caprius larvae, which are attachment-stage larvae, using diatoms as feed and used as test organisms. 19 ml of artificial seawater containing 10 larvae was transferred to a petri dish having a diameter of 5 cm. 10 mg of the test compound was added to cyclohexane and the surfactant Tween-80.
(Tween-80; manufactured by Atlas Powder Co., Ltd.) and diluted to a predetermined concentration with artificial seawater as 1 g of an emulsion containing 10: 1. 1 ml of this was added to the test petri dish. The petri dish was allowed to stand in a constant temperature room at 20 ° C., the number of deaths after 24 hours was examined, and this test was repeated three times to obtain a half-lethal concentration (hereinafter referred to as LC 50 ). Table 1 shows the results.
（海水浸漬試験） 実施例２ ３′−イソプロピル−２−メチルベンズアニリド（化
合物１）をＮ−（2,4,6−トリクロロフェニル）マレイ
ミド（化合物６）と1:2（重量比）の割合に配合し、さ
らにこれを下記の割合で配合して実験用小型アトライタ
ーで50ミクロン迄分散して防汚塗料を調製した。 (Seawater immersion test) Example 2 Ratio of 3'-isopropyl-2-methylbenzanilide (Compound 1) to N- (2,4,6-trichlorophenyl) maleimide (Compound 6) at 1: 2 (weight ratio) This was further blended in the following proportions and dispersed to 50 microns using a small laboratory attritor to prepare an antifouling paint.
（配合） （配合％） 化合物１ 10 化合物６ 20 アロプレンＲ−10 10（ICI 社製塩化ゴム樹脂） ロジン ７ DOP １ 弁柄 10 タルク 10 亜鉛華 ６ シェルゾールＡ 26 合計 100％ この防汚塗料を、離形剤等の油脂をキシレンで十分洗
い落としたFRP板（300×100×3mm）上に１回に5gずつ、
２回刷毛塗りして試験板を調製した。この試験板を鉄枠
にはめ込み、浸漬用筏から水中に吊るし、1.5mの深さの
所に維持した。海水中に浸漬しておいた試験板を４ケ
月、８カ月、12ケ月目に引き上げて付着した動物類、藻
類などの生物の付着度を付着面積の全面積に対する百分
率として表し、その結果を第２表に示す。(Blend) (Blend%) Compound 1 10 Compound 6 20 Alloprene R-10 10 (chlorinated rubber resin manufactured by ICI) Rosin 7 DOP 1 Red stalk 10 Talc 10 Zinc flower 6 Shellsol A 26 100% in total 5 g of this antifouling paint at a time on a FRP board (300 x 100 x 3 mm), in which the fats and oils such as the release agent were thoroughly washed with xylene,
Test plates were prepared by brushing twice. The test plate was fitted into an iron frame, suspended from a raft for immersion in water, and maintained at a depth of 1.5 m. The test plates immersed in seawater were pulled up at 4 months, 8 months, and 12 months, and the degree of adhesion of organisms such as animals and algae that adhered was expressed as a percentage of the total area of the attached area, and the results were expressed as percentages. The results are shown in Table 2.
実施例３〜５ 前記の化合物１〜８（化合物３、４以外）を用い混
合、配合し、実施例２と同様に化合物の合計が30％とな
るよう配合して塗料を調製した。他は同様の方法で、海
中浸漬試験を行った。結果を第２表に示す。Examples 3 to 5 The above-mentioned compounds 1 to 8 (other than compounds 3 and 4) were mixed and blended, and similarly to Example 2, blended so that the total amount of the compounds was 30% to prepare a coating material. Other than that, the sea immersion test was performed by the same method. The results are shown in Table 2.
実施例６ 実施例２の防汚塗料で、室温で保管し、塗料安定性試
験（３ケ月）に供した塗料を実施例２と同様の方法で海
中浸漬試験を行った。その結果を第２表に示す。ただ
し、実施例６は他の実施例より３ケ月遅れて海中浸漬試
験を行った。その結果を第２表に示す。Example 6 The antifouling paint of Example 2 stored at room temperature and subjected to a paint stability test (3 months) was subjected to a sea immersion test in the same manner as in Example 2. Table 2 shows the results. However, in Example 6, the underwater immersion test was performed three months later than the other examples. Table 2 shows the results.
比較例１ FRP板（300×100×3mm）に付着している離型剤等の油
脂をキシレンで十分洗い落とした試験板を調製し、無塗
装のままブランクとして実施例２と同様の方法で海中浸
漬試験を行った。その結果を第２表に示す。COMPARATIVE EXAMPLE 1 A test plate was prepared by thoroughly removing the oils and fats such as the release agent adhering to the FRP plate (300 × 100 × 3 mm) with xylene. An immersion test was performed. Table 2 shows the results.
比較例２ 化合物の１の代わりに３′−イソプロポキシ−２−メ
チルベンズアニリド（化合物５）を同量配合した以外は
実施例２と同様に塗料を調製し、同様の方法で海水浸漬
試験を行った。その結果を第２表に示す。Comparative Example 2 A coating material was prepared in the same manner as in Example 2 except that the same amount of 3'-isopropoxy-2-methylbenzanilide (Compound 5) was used instead of Compound 1, and a seawater immersion test was carried out in the same manner. went. Table 2 shows the results.
比較例３ 比較例２の防汚塗料で、室温で保管し、塗料安定性試
験（３ケ月）に供した塗料を実施例２と同様の方法で海
中浸漬試験を行った。その結果を第２表に示す。ただ
し、比較例３は他の比較例より３ケ月遅れて海中浸漬試
験を行った。また、この時の塗膜は100ミクロン以上の
粒が多くあった。その結果を第２表に示す。Comparative Example 3 The antifouling paint of Comparative Example 2, which was stored at room temperature and subjected to a paint stability test (3 months), was subjected to a sea immersion test in the same manner as in Example 2. Table 2 shows the results. However, in Comparative Example 3, the underwater immersion test was performed three months later than the other Comparative Examples. In addition, the coating film at this time had many particles of 100 microns or more. Table 2 shows the results.
（塗料安定性試験） 実施例２〜５及び比較例２の防汚塗料を室温で保管
し、３ケ月経過した時点で塗料の粒度を測定した。その
結果を第３表に示す。また、粒度の測定はJIS K54004.
4.Aの方法に準じて行った。 (Paint Stability Test) The antifouling paints of Examples 2 to 5 and Comparative Example 2 were stored at room temperature, and the particle size of the paint was measured after 3 months. Table 3 shows the results. The measurement of particle size is JIS K54004.
Performed according to the method of 4.A.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ (Ａ０１Ｎ 37/22 47:26） (56)参考文献 特開 昭54−59325（ＪＰ，Ａ) 特開 昭53−72823（ＪＰ，Ａ) 特開 昭64−6238（ＪＰ，Ａ) 特開 昭59−167504（ＪＰ，Ａ) 特開 平１−143804（ＪＰ，Ａ) 特開 昭52−133939（ＪＰ，Ａ) 特公 昭61−15843（ＪＰ，Ｂ２) (58)調査した分野(Int.Cl.6，ＤＢ名) A01N 37/18 - 37/32 ＣＡ（ＳＴＮ)──────────────────────────────────────────────────の Continuation of the front page (51) Int.Cl. 6 Identification symbol FI (A01N 37/22 47:26) (56) References JP-A-54-59325 (JP, A) JP-A-53-72823 ( JP, A) JP-A-64-6238 (JP, A) JP-A-59-167504 (JP, A) JP-A-1-143804 (JP, A) JP-A-52-133939 (JP, A) 61-15843 (JP, B2) (58) Fields investigated (Int. Cl. 6 , DB name) A01N 37/18-37/32 CA (STN)
Claims (2)
す。）て表される３′−イソプロピル−ベンズアニリド
化合物を有効成分とする貝類付着防止剤。(1) Expression (In the formula, R represents a methyl group or a trifluoromethyl group.) A shellfish adhesion inhibitor comprising a 3'-isopropyl-benzanilide compound represented by the following formula:
３′−イソプロピル−ベンズアニリド化合物より選ばれ
る少なくとも１種と、 （ロ）Ｎ−（２′,4′,6′−トリクロロフェニル）マレ
イミド、2,3−ジクロロ−Ｎ−（２′,6′−ジエチルフ
ェニル）マレイミド、2,3−ジクロロ−Ｎ−（２′−メ
チル−６′−エチルフェニル）マレイミド、テトラメチ
ルチウラムジスルフィド及びテトラエチルチウラムジス
ルフィドより選ばれる少なくとも１種とを有効成分とし
て含有することを特徴とする水中生物付着防止剤。2. (a) at least one selected from the 3'-isopropyl-benzanilide compounds represented by the formula (I) according to claim 1, and (b) N- (2 ', 4', 6 ' -Trichlorophenyl) maleimide, 2,3-dichloro-N- (2 ', 6'-diethylphenyl) maleimide, 2,3-dichloro-N- (2'-methyl-6'-ethylphenyl) maleimide, tetramethyl An underwater biofouling inhibitor comprising as an active ingredient at least one selected from thiuram disulfide and tetraethylthiuram disulfide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25191290A JP2899093B2 (en) | 1990-09-25 | 1990-09-25 | Underwater organism adhesion inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25191290A JP2899093B2 (en) | 1990-09-25 | 1990-09-25 | Underwater organism adhesion inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04134003A JPH04134003A (en) | 1992-05-07 |
| JP2899093B2 true JP2899093B2 (en) | 1999-06-02 |
Family
ID=17229811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25191290A Expired - Fee Related JP2899093B2 (en) | 1990-09-25 | 1990-09-25 | Underwater organism adhesion inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2899093B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4785154B2 (en) * | 2008-12-25 | 2011-10-05 | 株式会社エス・ディー・エス バイオテック | Preservative for wood preservation and method of wood treatment |
| GB2516216B (en) * | 2013-06-04 | 2016-01-06 | Honda Motor Co Ltd | Fixture of tilt detector |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6115843B2 (en) | 2016-02-17 | 2017-04-19 | パナソニックＩｐマネジメント株式会社 | Oral hygiene equipment |
-
1990
- 1990-09-25 JP JP25191290A patent/JP2899093B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6115843B2 (en) | 2016-02-17 | 2017-04-19 | パナソニックＩｐマネジメント株式会社 | Oral hygiene equipment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04134003A (en) | 1992-05-07 |
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