JPS6356890B2 - - Google Patents
Info
- Publication number
- JPS6356890B2 JPS6356890B2 JP57180958A JP18095882A JPS6356890B2 JP S6356890 B2 JPS6356890 B2 JP S6356890B2 JP 57180958 A JP57180958 A JP 57180958A JP 18095882 A JP18095882 A JP 18095882A JP S6356890 B2 JPS6356890 B2 JP S6356890B2
- Authority
- JP
- Japan
- Prior art keywords
- alkoxysilane
- composition
- alkyl group
- crosslinking
- oxide
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 5
- -1 polyethylene Polymers 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000004079 stearyl 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])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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Description
本発明はビニルアルコキシシランがグラフトさ
れた合成樹脂などのアルコキシシラン結合を含む
化合物に該化合物の縮合触媒が添加されてなるア
ルコキシシラン系架橋性組成物に存する。従来に
おいて、ビニルアルコキシシラン類がグラフトさ
れたポリエチレン―シランゲラフトポリマーと
か、アルコキシシラン共重合ポリエチレン、ポリ
プロピレン等の変性ポリマーを架橋させてより高
次の例えば耐熱性等の性能を付与することが行わ
れている。そして、この架橋を生ぜしめるために
アルコキシシランの縮合を行わせるための縮合触
媒としてはアミン類、酸類やアルキルスズカルボ
キシレート、有機チタン系化合物等の有機金属系
触媒が知られている。しかしながら、これらの縮
合触媒を用いた場合は縮合反応が非常に遅く、実
用化するには、熱水等に浸漬して水処理を行うか
又は組成物に含水塩や潮解性塩等を混入して組成
物中への水分の導入量を増加させて縮合反応を増
速させることが行われて来たが、水処理の採用は
水槽等の装置類や水処理工程が新らたに必要とな
り、又、含水塩、潮解性塩等の添加は組成物の諸
物性を低下させる傾向にあるので、これらは余り
好ましいことでない。
本発明は上記の如き現状にかんがみ、すみやか
に単に空気中の水分ないしは樹脂が自然状況下で
吸着、吸水している程度の水分によつてすみやか
にアルコキシシランの縮合反応が進行して、該縮
合反応が完了し得るアルコキシシラン系架橋性組
成物を提供することを目的として研究せる結果な
されたものであり、その要旨は、アルコキシシラ
ン結合を含む化合物に、
一般式
The present invention resides in an alkoxysilane-based crosslinkable composition prepared by adding a condensation catalyst of the compound to a compound containing an alkoxysilane bond, such as a synthetic resin grafted with vinylalkoxysilane. Conventionally, polyethylene-silane graft polymers grafted with vinyl alkoxysilanes, modified polymers such as alkoxysilane copolymerized polyethylene, and polypropylene have been crosslinked to impart higher performance, such as heat resistance. It is being said. As condensation catalysts for condensing alkoxysilanes to produce this crosslinking, amines, acids, alkyltin carboxylates, organometallic catalysts such as organic titanium compounds are known. However, when these condensation catalysts are used, the condensation reaction is very slow, and for practical use, water treatment must be performed by immersion in hot water, etc., or hydrated salts, deliquescent salts, etc. must be mixed into the composition. It has been attempted to speed up the condensation reaction by increasing the amount of water introduced into the composition, but the adoption of water treatment requires new equipment such as a water tank and a water treatment process. Furthermore, the addition of hydrated salts, deliquescent salts, etc. tends to deteriorate the physical properties of the composition, and is therefore not very desirable. In view of the above-mentioned current situation, the present invention has been developed by simply proceeding with the condensation reaction of alkoxysilane by simply using moisture in the air or moisture to the extent that the resin adsorbs and absorbs water under natural conditions. This was done as a result of research aimed at providing an alkoxysilane-based crosslinking composition in which the reaction can be completed.
【式】（R1はアルキル基、R2は
アルキル基又は他の有機基である）で表わされる
アルキルスズオキシド化合物が添加されてなるこ
とを特徴とするアルコキシシラン系架橋性組成物
に存する。
本発明に用いられる上記アルキルスズオキシド
化合物の一般式におけるR1はアルキル基である
が、とくに炭素数１〜８のアルキル基が好まし
く、又、該アルキル基は分岐していてもよい。
又、上記一般式中のR2はR1と同様アルキル基で
あつてもよく、若しくはアルキル基以外の有機基
であつてもよい。
この有機基としては、その中に酸素や窒素、イ
オウ等の炭素及び水素以外の元素を含んでいても
差支えないものであり、該有機基としては例えば
R′−COO−基（R′はアルキル基）、R′O−CO
−CH2−Ｓ−基、R′O−CO−HC＝CH−COO−
基等が挙げられる。
又、上記化合物の本発明に用いられて好適な例
としてはジメチルスズオキサイド、ジブチルスズ
オキサイド、ジオクチルスズオキサイド、モノメ
チルモノステアリールスズオキサイド、モノメチ
ルモノチオグリコール酸ステアリールエステルメ
ルカプトスズオキサイド、モノオクチルモノチオ
グリコール酸オクチルエステルメルカプトスズオ
キサイド、モノメチルモノステアリールエステル
マレイエートスズオキシド等が挙げられる。
次に本発明におけるアルコキシシラン結合を含
む化合物とは、分子中にアルコキシ基がケイ素に
結合した分子構造を有するものを指し、例えばビ
ニルアルコキシシランがポリエチレン等のポリマ
ーにグラフト結合したビニルアルコキシシラング
ラフトポリマー、ビニルアルコキシシランと他の
単量体との共重合体などの高分子物質やシランカ
ツプリング剤などのアルコキシシラン結合を有す
る低分子物質等が挙げられる。本発明の架橋性組
成物を用意するには前記アルコキシシラン結合を
含む化合物と前記アルキルスズオキサイド化合物
を加え合せて混合すればよいが、使用量としては
前者100重量部に対し通常後者を0.001〜１重量部
用いるのがよい。そして該架橋性組成物がビニル
アルコキシシラングラフトポリマーなどの高分子
物質である場合は、押出機、射出成型機等の適宜
な成形手段を用いて成形したのち大気中に放置し
ておくと、その中に含まれるアルキルスズオキサ
イド化合物の触媒作用により高分子物質中や大気
中の水分とアルコキシシランとが反応してシラノ
ール縮合が生じポリマー同志が架橋して耐熱性な
どが向上する等より高い品質のものとなるのであ
る。勿論架橋速度をより高めるため、熱水に浸漬
したり、水蒸気に接触させる等の処理を行うこと
も可能であるが、大気中に放置する場合及び上記
の熱水等による処理の場合のいずれにおいても、
従来の縮合触媒を用いた場合に比して、本発明組
成物は架橋速度が著るしく早く、短時間で架橋を
完了することが出来るものであり、作業性にすぐ
れたものであると共に、組成物ないしは成形物の
物性を低下せしめる架橋速度向上のための含水塩
や潮解性塩などの添加剤を必要としないので物性
的にも良好なものが得られるのである。
又、本発明組成物は高分子系以外のものであつ
ても該組成物がすみやかに架橋し得るという特徴
を生かして有効に用いられることが出来、例えば
アルコキシシラン結合を含むシランカツプリング
剤に前記アルキルスズオキサイド化合物を加えて
本発明の組成物となし、これをガラス繊維やその
他の補強材ないしは充填剤の表面処理に、樹脂等
との接合性向上を目的として使用することが可能
であり、又、本発明組成物が液状の場合はこれを
塗布したのち架橋することにより硬化し被覆を与
えるのでコーテイング剤としての用途に用いるこ
とも出来る。
本発明のアルコキシシラン系架橋性組成物は上
述の通りの構成のものであるので、この中に含ま
れるアルキルスズオキシド化合物の作用によつて
従来のものに比して架橋速度が極めて早く短時間
で架橋が完了するので作業性にすぐれたものであ
り、又、物性の低下を来たす恐れのある含水塩や
潮解性物質等を架橋促進のために添加する必要が
なく、従つてこのための物性低下を来たすことの
ないものである。
以下実施例にもとづいて説明する。
実施例 １
ポリエチレン（MI＝4.0）100重量部に、ビニ
ルトリメトキシシラン１重量部、ベンゾイルパー
オキサイド１重量部を加えて均一に混合した混合
物を180―220℃で混練押出を行い、ビニルトリメ
トキシシランがグラフトされたポリエチレンを用
意した。
さらに該グラフトされたポリエチレンをアセト
ンに浸漬することにより、過酸化物、未反応ビニ
ルトリメトキシシランの除去を行つて精製した。
かくして用意したグラフト化ポリエチレン100
重量部に、ジブチルスズオキシド（実施例）又は
ジブチルスズシラウレート（比較例）をそれぞれ
第１表に示される量加えて160℃でのロール混練
を５分間行つてシートとなして試験片を用意し
た。この試験片を85℃の熱水に第１表に示される
時間浸漬して引上げ、120℃の熱キシレンに対す
る不溶分の割合（ゲル分率）を測定した所、同表
の通りであつた。An alkoxysilane crosslinking composition characterized in that it contains an alkyltin oxide compound represented by the formula: (R 1 is an alkyl group, R 2 is an alkyl group or another organic group). R 1 in the general formula of the alkyltin oxide compound used in the present invention is an alkyl group, and an alkyl group having 1 to 8 carbon atoms is particularly preferred, and the alkyl group may be branched.
Further, R 2 in the above general formula may be an alkyl group like R 1 or may be an organic group other than an alkyl group. This organic group may contain elements other than carbon and hydrogen, such as oxygen, nitrogen, and sulfur, and examples of the organic group include, for example, R'-COO- group (R' is alkyl group), R′O−CO
-CH 2 -S- group, R'O-CO-HC=CH-COO-
Examples include groups. Examples of the above compounds suitable for use in the present invention include dimethyltin oxide, dibutyltin oxide, dioctyltin oxide, monomethylmonostearyltin oxide, monomethylmonothioglycolic acid stearyl ester mercaptotin oxide, monooctylmonothio Examples include glycolic acid octyl ester mercaptotin oxide, monomethylmonostearyl ester maleate tin oxide, and the like. Next, the compound containing an alkoxysilane bond in the present invention refers to a compound having a molecular structure in which an alkoxy group is bonded to silicon in the molecule, such as a vinylalkoxysilane graft polymer in which vinylalkoxysilane is grafted to a polymer such as polyethylene. , high-molecular substances such as copolymers of vinyl alkoxysilane and other monomers, and low-molecular substances having alkoxysilane bonds such as silane coupling agents. To prepare the crosslinkable composition of the present invention, the compound containing an alkoxysilane bond and the alkyltin oxide compound may be added and mixed, but the amount used is usually 0.001 to 100 parts by weight of the latter to 100 parts by weight of the former. It is preferable to use 1 part by weight. When the crosslinkable composition is a polymeric material such as a vinyl alkoxysilane graft polymer, if it is molded using an appropriate molding means such as an extruder or injection molding machine and then left in the atmosphere, Due to the catalytic action of the alkyltin oxide compound contained in the alkoxysilane, moisture in the polymeric material or the atmosphere reacts with the alkoxysilane, resulting in silanol condensation, which crosslinks the polymers together, improving heat resistance, etc. It becomes something. Of course, in order to further increase the crosslinking rate, it is possible to perform treatments such as immersion in hot water or contact with water vapor, but in either case of leaving it in the air or in the case of the above-mentioned treatment with hot water, etc. too,
Compared to the case where conventional condensation catalysts are used, the composition of the present invention has a significantly faster crosslinking rate, can complete crosslinking in a short time, and has excellent workability. Since there is no need for additives such as hydrated salts or deliquescent salts to improve the crosslinking rate, which degrade the physical properties of the composition or molded product, good physical properties can be obtained. In addition, the composition of the present invention can be effectively used for materials other than polymers by taking advantage of the characteristic that the composition can be quickly crosslinked. For example, it can be used as a silane coupling agent containing an alkoxysilane bond. The composition of the present invention can be prepared by adding the alkyltin oxide compound described above, and this can be used for surface treatment of glass fibers and other reinforcing materials or fillers for the purpose of improving bondability with resins, etc. Furthermore, when the composition of the present invention is in liquid form, it can be applied and then cured by crosslinking to provide a coating, so that it can also be used as a coating agent. Since the alkoxysilane crosslinkable composition of the present invention has the above-mentioned structure, the crosslinking speed is extremely high and shortened compared to conventional compositions due to the action of the alkyltin oxide compound contained therein. It has excellent workability because crosslinking is completed in just a few seconds, and there is no need to add hydrated salts or deliquescent substances to promote crosslinking, which may cause deterioration of physical properties. It is something that will not deteriorate. The following will be explained based on examples. Example 1 100 parts by weight of polyethylene (MI=4.0), 1 part by weight of vinyltrimethoxysilane and 1 part by weight of benzoyl peroxide were added and mixed uniformly. A mixture was kneaded and extruded at 180-220°C to produce vinyltrimethoxysilane. Polyethylene grafted with silane was prepared. The grafted polyethylene was further purified by immersing it in acetone to remove peroxide and unreacted vinyltrimethoxysilane. The thus prepared grafted polyethylene 100
Dibutyltin oxide (example) or dibutyltin silaurate (comparative example) was added in the amounts shown in Table 1 to the parts by weight, and roll kneading was performed at 160°C for 5 minutes to form a sheet to prepare a test piece. . This test piece was immersed in hot water at 85°C for the time shown in Table 1 and pulled out, and the ratio of insoluble matter (gel fraction) to hot xylene at 120°C was measured, and the results were as shown in the table.
【表】【table】
【表】
実施例 ２
ビニルトリメトキシシラン10ｇに、第２表に示
される化合物を加えたものを85℃で５分間加熱し
た後の状態を観察した所、同表の通りであつた。[Table] Example 2 A mixture of 10 g of vinyltrimethoxysilane and the compounds shown in Table 2 was heated at 85°C for 5 minutes, and the results were as shown in the table.
Claims (1)
アルキルスズオキシド化合物が添加されてなるこ
とを特徴とするアルコキシシラン系架橋性組成
物。[Claims] 1. An alkyltin oxide compound represented by the general formula [Formula] (R 1 is an alkyl group, R 2 is an alkyl group or another organic group) is added to a compound containing an alkoxysilane bond. An alkoxysilane crosslinkable composition characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18095882A JPS5971364A (en) | 1982-10-14 | 1982-10-14 | Crosslinkable composition based on alkoxysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18095882A JPS5971364A (en) | 1982-10-14 | 1982-10-14 | Crosslinkable composition based on alkoxysilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5971364A JPS5971364A (en) | 1984-04-23 |
| JPS6356890B2 true JPS6356890B2 (en) | 1988-11-09 |
Family
ID=16092248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18095882A Granted JPS5971364A (en) | 1982-10-14 | 1982-10-14 | Crosslinkable composition based on alkoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5971364A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04235499A (en) * | 1991-01-09 | 1992-08-24 | Sharp Corp | Remote control transmitter |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047476A (en) * | 1989-05-12 | 1991-09-10 | Union Carbide Chemicals And Plastics Company Inc. | Process for crosslinking hydrolyzable copolymers |
| JP2749953B2 (en) * | 1990-05-22 | 1998-05-13 | キヤノン株式会社 | Image forming device |
| CN111902485A (en) * | 2018-03-28 | 2020-11-06 | 株式会社钟化 | Method for producing heat-curable cured product, and heat-curable composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57105446A (en) * | 1980-12-19 | 1982-06-30 | Kanegafuchi Chem Ind Co Ltd | Curable composition |
-
1982
- 1982-10-14 JP JP18095882A patent/JPS5971364A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57105446A (en) * | 1980-12-19 | 1982-06-30 | Kanegafuchi Chem Ind Co Ltd | Curable composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04235499A (en) * | 1991-01-09 | 1992-08-24 | Sharp Corp | Remote control transmitter |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5971364A (en) | 1984-04-23 |
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