JPS61112086A - Aminosilane coupling agent - Google Patents
Aminosilane coupling agentInfo
- Publication number
- JPS61112086A JPS61112086A JP59233677A JP23367784A JPS61112086A JP S61112086 A JPS61112086 A JP S61112086A JP 59233677 A JP59233677 A JP 59233677A JP 23367784 A JP23367784 A JP 23367784A JP S61112086 A JPS61112086 A JP S61112086A
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- Prior art keywords
- formula
- compound
- hydrocarbon residue
- hydrocarbon group
- coupling agent
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明は、
式：
％式％）
（式中、Ａは芳香族炭化水素基、Ｂは炭化水素基、Ｄは
１〜６個の炭素原子を有する脂肪族炭化水？１Ｒ′は水
素又は１〜４個の炭素原子を有する炭１ヒ水素基、Ｒｎ
は水素又は１〜４個の炭素原子をイ１する脂肪族炭化水
素基又は芳香族炭化水素基てあり、ａは１〜３である）
の化合物、および／まｌこは
〔トＩＮＡＮＩ−ＩＢＤ） Ｓｉ （
ＯＲ’ ） Ｘ ＝ａ
４−ａ＋
〔■］（式中、Ａ、Ｂ、Ｄ、Ｒ’ 、Ｒ″
およ１ｃＦａｔ、を前記定義と同じであり、Ｘはハロゲ
ンである）の化合物を含有するアミノシラン系カップリ
ング剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the formula: %Formula %) (wherein A is an aromatic hydrocarbon group, B is a hydrocarbon group, and D is an aliphatic hydrocarbon having 1 to 6 carbon atoms) ?1R' is hydrogen or a carbon arsenic group having 1 to 4 carbon atoms, Rn
is hydrogen or an aliphatic hydrocarbon group or aromatic hydrocarbon group containing 1 to 4 carbon atoms, and a is 1 to 3)
compound, and/maruko [toINANI-IBD]
OR' ) X = a
4-a+
[■] (In the formula, A, B, D, R', R''
and 1cFat, where X is the same as defined above, and X is a halogen.
本発明に使用する前記式（Ｉ）および（ＩＩ）の新規な
アミノシラン系化合物は、
式：
％式％）
（式中、Ｒはエポキシ基、イソシアネート基又はハロゲ
ンを含有する炭化水素基であり、ａは１〜３であり、Ｒ
′は水素又は１〜４個の炭素原子を有する炭化水素基で
ある）の化合物と、式：
（式中、ＲＬＪは水素又は１〜４個の炭素原子を有する
脂肪族炭化水素基又は芳香族炭化水素基であり、Ａは芳
香族炭化水素基である）の化合物とを反応さゼることに
より製造することができる。The novel aminosilane compounds of formulas (I) and (II) used in the present invention have the following formula: %formula%) (wherein R is an epoxy group, an isocyanate group, or a halogen-containing hydrocarbon group, a is 1 to 3, R
' is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms) and a compound of the formula: (wherein RLJ is hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms or an aromatic A is a hydrocarbon group, and A is an aromatic hydrocarbon group).
シラン化合物は、ガラス繊維の処理剤としてよく知られ
ているが、従来この用途に供せられている 例えばγ−
アミノプロピルトリメトキシシラン、γ−グリシドキシ
プロピルトリメトキシシランなどは耐熱性が不十分であ
り、最近とみに耐熱性を要求される電子部品材料である
積層板などの用途に供することができない。Silane compounds are well known as treatment agents for glass fibers, and conventionally used for this purpose, such as γ-
Aminopropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, and the like have insufficient heat resistance and cannot be used for applications such as laminates, which are electronic component materials that require heat resistance these days.
本発明者は、かかる用途に十分耐え得るガラスミｍ用処
理剤を鋭意検討し、芳香族環を有したジアミノ化合物と
エポキシ基、イソシアネート基またはハロゲンを有する
シラン化合物との付加または縮合によって生成する本発
明のごときアミノシラン化合物を見い出した。The inventors of the present invention have made extensive studies on a treatment agent for glass shavings that can sufficiently withstand such uses, and have discovered a treatment agent for glass shavings produced by the addition or condensation of a diamino compound having an aromatic ring and a silane compound having an epoxy group, an isocyanate group, or a halogen. An aminosilane compound according to the invention has been discovered.
本発明のアミノシラン系カップリング剤を製造するのに
用いられる式（ＩＩＩ）および（ＩＶ）の化合物の好適
例においては、式（ＩＩＩ）中のエポキシ基を含有する
炭化水素基としては、β−（３，１エポキシシクロヘキ
シル）エチル、γ−グリシドキシプロピル、４ （３，
４−エポキシ）フェニル等があり、イソシアネート基を
含有する炭化水素基としてはγ−イソシアネートプロピ
ルがあり、ハロゲンを含有する炭化水素基としては、２
−り口【」エチル、３−クロロプロピル等があり、また
式（［Ｖ）中の芳香族アミノ化合物としては、ｐ−ジア
ミノベンゼン、４．４′−ジアミノジフェニルスルホン
、４．４′−ジアミノジフェニルエーテル、４．４′
−ジアミノシフ１ニルメタン等がある。また前記式（Ｉ
）、（ｎ）および（ｒＶ）中の八としては、例えばフェ
ニル、ジノエニルメタン、ジフェニルエーテル又はジフ
ェニルスルホン等があり、またＢとしては、例えばシク
ロヘキサノール、２−ヒドロキシプロポキシまたはウレ
イド等があるがその他の炭化水素基でもよい。In preferred examples of the compounds of formulas (III) and (IV) used to produce the aminosilane coupling agent of the present invention, the epoxy group-containing hydrocarbon group in formula (III) is β- (3,1 epoxycyclohexyl)ethyl, γ-glycidoxypropyl, 4 (3,
4-epoxy) phenyl, etc., hydrocarbon groups containing isocyanate groups include γ-isocyanatepropyl, and hydrocarbon groups containing halogens include 2
Examples of aromatic amino compounds in the formula ([V) include p-diaminobenzene, 4,4'-diaminodiphenylsulfone, 4,4'-diamino diphenyl ether, 4.4'
-Diamino Schiff 1-nylmethane, etc. Also, the formula (I
), (n) and (rV) include, for example, phenyl, dinoenylmethane, diphenyl ether or diphenyl sulfone, and B includes, for example, cyclohexanol, 2-hydroxypropoxy or ureido, but other carbonized It may also be a hydrogen group.
また本発明の７ミノシランを得るために、溶剤を使用す
ることが望ましく好適例としては、エポキシ基またはア
ミノ基と反応する官能基を含有しない溶媒であるが、特
に本発明の７ミノシランが可溶化するジメチルアセタミ
ド、ジメチルアセタミドなどを使用することが望ましい
。触媒については、アミノ基とエポキシ基の反応または
アミノ基とハロゲン化炭化水素から脱塩酸を行なえる、
脱！Ｘ酸剤などの使用も可能である。In addition, in order to obtain the 7-minosilane of the present invention, it is desirable to use a solvent, and a preferred example is a solvent that does not contain a functional group that reacts with an epoxy group or an amino group. It is desirable to use dimethylacetamide, dimethylacetamide, etc. As for the catalyst, it can perform the reaction between amino groups and epoxy groups or dehydrochloride from amino groups and halogenated hydrocarbons.
Get off! It is also possible to use X acid agents and the like.
次に、本発明を具体的に説明するために本発明の実施例
を示す。以下の実施例は、本発明を限定するものではな
い。「部」はすべて重量部である。Next, examples of the present invention will be shown in order to specifically explain the present invention. The following examples do not limit the invention. All "parts" are parts by weight.
実施例１
あらかじめ内部を乾燥窒素で置換した２１の四ツ目フラ
スコに、４．４′ −ジアミノシフ１ニルメタン２９７
．５部（１，５モル）とジメチルスルホ腓シト８３２．
９部を添加し、窒素下で溶液が１３０℃になるまで加熱
撹拌する。内容物の温度が１３０℃に達した後、滴下ロ
ートからβ−（３，４−一エボキシシロクヘキシル）エ
チルトリメトキシシラン３６９．６（１（１，５モル）
を１時間かけてゆっくり滴下する。この添加操作は、還
流冷却塔を付して行ない、内容物が系外に漏洩すること
を防止する。Example 1 Into a 21-meter four-eye flask whose interior was previously purged with dry nitrogen, 297 g of 4,4'-diaminosif-1-nylmethane was added.
．． 5 parts (1.5 mol) and dimethyl sulfonate 832.
Add 9 parts and heat and stir under nitrogen until the solution reaches 130°C. After the temperature of the contents reached 130°C, 369.6 (1 (1.5 mol)) of β-(3,4-mono-epoxysiloxhexyl)ethyltrimethoxysilane was added from the dropping funnel.
Slowly drip over 1 hour. This addition operation is carried out using a reflux cooling tower to prevent the contents from leaking out of the system.
１３０℃で還流不反応を１０時間以上行ない、赤外分光
光度計を用い、９１０ｃｍ”に１ポ１シに起因する特性
吸収のないことを確認してから、反応系をゆっくり冷部
する。After refluxing and unreacting at 130° C. for 10 hours or more, and using an infrared spectrophotometer to confirm that there is no characteristic absorption attributable to the 1-polymer at 910 cm, the reaction system is slowly cooled down.
溶媒を除去した生成物は、ＩＲおよび元素分相から下記
分子式に相当するしのであることを確認した。The product from which the solvent was removed was confirmed by IR and elemental phase separation to be a compound having the following molecular formula.
０Ｈ
◎ＩＲ分析
ｕ−ＯＨ１２６０ｃｍ−’
Ｌ／＝ＮＨ１３１０ｃｍ−１
部元素分析
Ｃ（％） Ｈ（％）Ｓｉ（％）
計算値 ６４．８ ８．２ ６．３分析値 ６４
．４ ８．１ ６．５実施例２
あらかじめ内部を乾燥窒素で置換した２１の四ツ目フラ
スコに、４．４′−ジアミノジフェニルエーテル３００
．３部（１，５モル）とジメチルホルマミド８２８．６
部を添加し、窒素雰囲気下で溶液が１２０℃になるまで
加熱攪拌する。内容物の温度が１２０℃に達した後、滴
下ロートからγ−イソシアネートプロピルトリメトキシ
シラン３７１．１部（１，５モル）を１時間かけて滴下
する。これらの反応操作は、還流冷却器を付して行ない
、内容物が系外に留出することを防止する。0H ◎IR analysis u-OH1260cm-' L/=NH1310cm-1 Elemental analysis C (%) H (%) Si (%) Calculated value 64.8 8.2 6.3 Analysis value 64
．． 4 8.1 6.5 Example 2 4.4'-diaminodiphenyl ether 300%
．． 3 parts (1.5 mol) and dimethylformamide 828.6
of the solution was added, and the solution was heated and stirred under a nitrogen atmosphere until the temperature reached 120°C. After the temperature of the contents reached 120° C., 371.1 parts (1.5 mol) of γ-isocyanatepropyltrimethoxysilane was added dropwise from the dropping funnel over 1 hour. These reaction operations are carried out using a reflux condenser to prevent the contents from distilling out of the system.
１２０℃で反応を５時間行ない、赤外分光光度計を用い
、２２７０ｃｍ”付近のイソシアネート基に起因する特
性吸収が消失したことを６部認してから、反応系をゆっ
くり冷却する。The reaction was carried out at 120° C. for 5 hours, and after confirming with an infrared spectrophotometer that the characteristic absorption due to isocyanate groups around 2270 cm” had disappeared, the reaction system was slowly cooled.
溶媒を除去した生成物は、ＩＲ，１５よひ元素弁＋ｌｉ
から下記の分子式に相当するものであることを確認した
。The product from which the solvent has been removed is IR, 15 elemental valve + li
It was confirmed that it corresponds to the following molecular formula.
◎ＩＲ分析
シーＮＨＣＯＮ、Ｈ−１６９０ｃｍ−’◎元素分析
Ｃ（％） Ｈ（％）Ｓｉ（％）
計算値 ５６．３ ６．７ ６．９
分析値 ５６．０ ６．６ ７．０
実施例３
あらかじめ内部を乾燥窒素で置換した２１の四ツ目フラ
スコに４．４′ −ジアミノジノ１ニルスルホン３７２
．８部（１，５モル）とジメチルスルホ■シト８２９．
４部を添加し、窒素雰囲気下で溶液が１４０℃になるま
で加熱攪拌する。内容物の温度が１４０℃に達した後、
滴下ロートからγ−クロロプロピルトリメトキシシラン
２９７．８部を滴下する。これらの反応操作は、還流冷
却器を付して行ない、内容物が系外に留出 −すること
を防止する。◎IR analysis sea NHCON, H-1690cm-'◎Elemental analysis C (%) H (%) Si (%) Calculated value 56.3 6.7 6.9 Analysis value 56.0 6.6 7.0 Example 3. Add 372 4,4'-diaminodino-1-nylsulfone to a 21-meter four-eye flask whose interior was previously purged with dry nitrogen.
．． 8 parts (1.5 mol) and dimethyl sulfosite 829.
4 parts of the solution were added, and the solution was heated and stirred under a nitrogen atmosphere until the temperature reached 140°C. After the temperature of the contents reaches 140℃,
297.8 parts of γ-chloropropyltrimethoxysilane is added dropwise from the dropping funnel. These reaction operations are carried out using a reflux condenser to prevent the contents from distilling out of the system.
１４０℃で反応を２０時間行ない、赤外分光光度計を用
い、６８０ ｃｍ−１付近の塩化アルキルに起因する特
性吸収を消失したことを確認してから、反応系をゆっく
り冷却する。The reaction is carried out at 140° C. for 20 hours, and after confirming using an infrared spectrophotometer that the characteristic absorption caused by alkyl chloride around 680 cm −1 has disappeared, the reaction system is slowly cooled.
溶媒を除去した生成物は、ＩＲおよび元素分析から下記
の分子式に相当するものであることを確認した。The product from which the solvent was removed was confirmed to correspond to the following molecular formula from IR and elemental analysis.
◎ＩＲ分析
ｙ＝ＮＨＣｌ １６６０ｃｍ−１◎元素分析
Ｃ（％） Ｈ（％）Ｓｉ（％）
ｉｔＷｌｌ ４８．４ ６．１ ６．３分析値 ４
８．３ ６．０ ６．４
実施例４
その他、各種の反応例を第１表に示す。但し、表中の溶
媒は下記の略号を使用する。◎IR analysis y=NHCl 1660cm-1 ◎Elemental analysis C (%) H (%) Si (%) itWll 48.4 6.1 6.3 Analysis value 4
8.3 6.0 6.4 Example 4 Other reaction examples are shown in Table 1. However, the following abbreviations are used for solvents in the table.
ＤＭＳＯニジメチルスルホキシド
Ｄ−ＡＣニジメチルアセタミド
ＤＭＦ ：ジメチルホルマミド
ｌ−ＩＭＰＡ：ヘキサメチルホスホルアミド試験例１
実施例１および２で得られた新規アミノシラン化合物を
使用した１ボ羊シ樹脂積閤板の耐熱性と含水率を測定し
た結果を第２表に示す。また、比較のためγ−アミノプ
ロピルトリ１トキシシラン〈日本ユニカー−Ａ−１１０
０）およびγ−グリシド１ジプロピルトリメトキシシラ
ン（日本ユニカーｉ＋ＩＡ−１８７＞の結果も併記する
。DMSO Ni-dimethyl sulfoxide D-AC Ni-dimethyl acetamide DMF: Dimethylformamide l-IMPA: Hexamethylphosphoramide Test Example 1 1-year resin production using the new aminosilane compound obtained in Examples 1 and 2 Table 2 shows the results of measuring the heat resistance and moisture content of the board. For comparison, γ-aminopropyltri-1-toxysilane <Nippon Unicar-A-110>
0) and γ-glycid 1 dipropyltrimethoxysilane (Nippon Unicar i+IA-187>) are also shown.
ガラスクロスの処理
実施例１および２で得られた新規アミノシラン化合物を
メタノールに溶解し、固型分０．５％の溶液を調製する
。γ−アミツブ０ピルトリエトキシシランは、蒸留水に
溶解し、固型分０．５％の溶液を調製し、またγ−グリ
シドキシプロビルトリメトキシシランは、あらかじめ酢
酸でｐＨ４に調整した蒸留水に溶解し、固型分１．０％
の溶液を調製する。Treatment of Glass Cloth The novel aminosilane compounds obtained in Examples 1 and 2 are dissolved in methanol to prepare a solution with a solid content of 0.5%. γ-Amitobyltriethoxysilane was dissolved in distilled water to prepare a solution with a solid content of 0.5%. Soluble in water, solid content 1.0%
Prepare a solution of
上記のそれぞれの溶液に脱油したガラスクロス（日東紡
績（ＩＩＷＥ−１８Ｋ）を浸漬し、スクイズロールで絞
り１１０℃×１０分間乾燥する。A deoiled glass cloth (Nitto Boseki (IIWE-18K)) was immersed in each of the above solutions, squeezed with a squeeze roll and dried at 110°C for 10 minutes.
ラミネート試ハの作
表面処理したガラスフ［１スにＦ Ｒ−４タイプの■ボ
キシ樹脂（油化シ１ルＴボヤシ■１とコート１０４５−
Ａ−７０）を含浸させ、１４０℃×１０分間乾燥してプ
レプリグとする。このブレプラグ８枚を重ね、上下に銅
箔を重ね、１７０℃×４０ ｋｇ／ｃｍｘ ７０分の条
件で成型する。全面エツチングによって銅箔を除去し、
５０Ｘ５０ｍｍの試片を切り出す。Preparation of laminate test surface treated glass sheet [1st surface] FR-4 type ■boxy resin (oil chemical 1 T-boss ■1 and coat 1045-
A-70) and dried at 140° C. for 10 minutes to obtain a prepreg. Eight of these blur plugs were stacked, copper foil was layered on top and bottom, and molded at 170°C x 40 kg/cm x 70 minutes. The copper foil is removed by etching the entire surface,
Cut out a 50x50mm specimen.
評価方法
（１）ハンダ耐熱試験
試片を１３３℃のプレッシャークツカーで処理また後、
２６０℃のハンダ浴に２０秒間浸漬する。試片面のふく
れ、またははがれが起こるプレッシャークツカーでの処
理時間を求める。Evaluation method (1) After treating the solder heat resistance test specimen with a pressure cooker at 133℃,
Immerse in a 260°C solder bath for 20 seconds. Determine the processing time in a pressure cutter that causes blistering or peeling of the specimen surface.
（２）吸水試験
丁
紙片を１３３℃のプレッシャークツカーで１８０分処理
した後、２３℃の蒸留水に２４時間浸漬し、吸水率を求
める。(2) Water absorption test A piece of paper is treated in a pressure cooker at 133°C for 180 minutes, then immersed in distilled water at 23°C for 24 hours to determine the water absorption rate.
試験例２
％＋１の化合物３および６の新規アミノシラン化合物を
使用したボリアミノビスンレイミド樹脂積層板の耐熱性
と含水率を測定した結果を第３表に示す。また、比較の
ためγ−７ミノブロピルトリエトキシシランおよびγ−
グリシドキシプロピルトリメト判ジシランの結果も併記
する。Test Example 2 Table 3 shows the results of measuring the heat resistance and moisture content of polyamino bisunreimide resin laminates using the new aminosilane compounds of Compounds 3 and 6 at %+1. For comparison, γ-7minopropyltriethoxysilane and γ-
The results for glycidoxypropyltrimethodisilane are also listed.
ガラスクロスの処理
新規アミノシラン化合物および比較例に用いるシラン化
合物の水溶液は、試験例１と同様にして調製する。Treatment of Glass Cloth Aqueous solutions of the new aminosilane compound and the silane compounds used in the comparative examples are prepared in the same manner as in Test Example 1.
上記のそれぞれの溶液に脱油したガラスクロス（日東紡
績ＵＷＥ −１１６Ｅ ） ヲｌ１５ｉｉ シ、スクイ
ズロールで絞り１１０℃×１０分間乾燥する。Glass cloth (Nittobo UWE-116E) deoiled with each of the above solutions was squeezed with a squeeze roll and dried at 110°C for 10 minutes.
ラミネート試片の作製
表面処理したガラスクロスにポリ７ミノビスマレイド樹
脂（ローンブーラン社ケルイミド６０１ ）とＮ−メチ
ル２ピロリドンの等均一混合物を含浸させ、１６０℃×
７分間乾燥してブレプリグとする。このプレブリグ８枚
を重ね、上下に銅箔を巾ね、１７０℃×４０にり／ＣＩ
ＩＩＸ ７０分の条件で成型する。２２０℃×１時間の
後硬化後、全面エツチングによって銅箔を除去し、５０
Ｘ５０１１１１の試片を切り出す。Preparation of laminate specimen A surface-treated glass cloth was impregnated with an equal homogeneous mixture of poly7minobismaleide resin (Lonboulin Kelimide 601) and N-methyl 2-pyrrolidone, and heated at 160°C.
Dry for 7 minutes to make a Brepprig. Stack 8 of these prebrigs, cover the top and bottom with copper foil, and heat at 170℃ x 40cm/CI
IIX: Mold for 70 minutes. After post-curing at 220°C for 1 hour, the copper foil was removed by etching the entire surface.
Cut out a specimen of X501111.
評価方法
（１）ハンダ耐熱試験
試片を１５１℃のプレッシャークツカーで処理した後、
２９０℃のハンダ浴に２０秒間浸漬する。試片面のふく
れ、またははがれが起こるプレッシャークツカーでの処
理時間を求める。Evaluation method (1) After treating the solder heat resistance test specimen with a pressure cooker at 151°C,
Immerse in a 290°C solder bath for 20 seconds. Determine the processing time in a pressure cutter that causes blistering or peeling of the specimen surface.
（２）吸水試験
切り出した試片を５０℃の乾燥機で２４時間放置した後
、２３℃の蒸留水に２４時間浸漬し、吸水率を求める。(2) Water absorption test The cut specimen was left in a dryer at 50°C for 24 hours, and then immersed in distilled water at 23°C for 24 hours to determine the water absorption rate.
Claims (1)
１〜６個の炭素原子を有する脂肪族炭化水素基、Ｒ′は
水素又は１〜４個の炭素原子を有する炭化水素基、Ｒ″
は水素又は１〜４個の炭素原子を有する脂肪族炭化水素
基又は芳香族炭化水素基であり、ａは１〜３である）の
化合物、および／または 式： ▲数式、化学式、表等があります▼〔II〕 （式中、Ａ、Ｂ、Ｄ、Ｒ′、Ｒ″およびａは前記定義と
同じであり、Ｘはハロゲンである）の化合物を含有する
アミノシラン系カップリング剤。[Claims] Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, A is an aromatic hydrocarbon group, B is a hydrocarbon group, and D has 1 to 6 carbon atoms. an aliphatic hydrocarbon group, R' is hydrogen or a hydrocarbon group having 1 to 4 carbon atoms, R''
is hydrogen or an aliphatic hydrocarbon group or an aromatic hydrocarbon group having 1 to 4 carbon atoms, and a is 1 to 3), and/or the formula: ▲ Numerical formula, chemical formula, table, etc. ▼ [II] An aminosilane coupling agent containing the compound (wherein A, B, D, R', R'' and a are the same as defined above, and X is a halogen).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59233677A JPS61112086A (en) | 1984-11-06 | 1984-11-06 | Aminosilane coupling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59233677A JPS61112086A (en) | 1984-11-06 | 1984-11-06 | Aminosilane coupling agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61112086A true JPS61112086A (en) | 1986-05-30 |
| JPH0113714B2 JPH0113714B2 (en) | 1989-03-07 |
Family
ID=16958802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59233677A Granted JPS61112086A (en) | 1984-11-06 | 1984-11-06 | Aminosilane coupling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61112086A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0408012A2 (en) * | 1989-07-12 | 1991-01-16 | Dow Corning Toray Silicone Company, Limited | Organosilicon compounds and method for their preparation |
| JPH05105689A (en) * | 1991-10-15 | 1993-04-27 | Shin Etsu Chem Co Ltd | Organic silicon compound |
| WO2000004029A3 (en) * | 1998-07-15 | 2001-05-25 | Great Lakes Chemical Europ | Phenylenediamine silanes as antiozonants and antioxidants for rubbers |
| US6794761B2 (en) * | 2001-04-26 | 2004-09-21 | Intel Corporation | No-flow underfill material |
| JP2004289102A (en) * | 2003-01-29 | 2004-10-14 | Asahi Kasei Chemicals Corp | Thermosetting composition for sealing light emitting element, and light emitting diode |
| US7018427B2 (en) | 2001-09-28 | 2006-03-28 | L'oreal S.A. | Dyeing composition containing a para-aminophenol or para-phenylenediamine compound substituted with a silane radical |
| JP2006241084A (en) * | 2005-03-03 | 2006-09-14 | Tokyo Univ Of Science | Surface-modifying agent, cytophilic material, method for producing cytophilic material and, bone-like transplant and method for producing bone-like transplant |
| JPWO2007004345A1 (en) * | 2005-06-30 | 2009-01-22 | 東レ株式会社 | Photosensitive resin composition and adhesion improver |
| WO2013191203A1 (en) * | 2012-06-20 | 2013-12-27 | 日産化学工業株式会社 | Silicon-containing resist underlayer film-forming composition having sulfone structure and amine structure |
| CN109879903A (en) * | 2019-01-09 | 2019-06-14 | 青岛科技大学 | One kind is novel to prevent old silane coupling agent and preparation method thereof |
| CN112745483A (en) * | 2021-01-15 | 2021-05-04 | 万华化学集团股份有限公司 | Epoxy resin curing agent, preparation method thereof, epoxy resin composition and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156677A (en) * | 1977-06-28 | 1979-05-29 | Union Carbide Corporation | Polymer composite articles containing amino substituted mercapto organo silicon coupling agents |
-
1984
- 1984-11-06 JP JP59233677A patent/JPS61112086A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156677A (en) * | 1977-06-28 | 1979-05-29 | Union Carbide Corporation | Polymer composite articles containing amino substituted mercapto organo silicon coupling agents |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0408012A2 (en) * | 1989-07-12 | 1991-01-16 | Dow Corning Toray Silicone Company, Limited | Organosilicon compounds and method for their preparation |
| JPH0344394A (en) * | 1989-07-12 | 1991-02-26 | Toray Dow Corning Silicone Co Ltd | Organosilicon compound and production thereof |
| JPH05105689A (en) * | 1991-10-15 | 1993-04-27 | Shin Etsu Chem Co Ltd | Organic silicon compound |
| WO2000004029A3 (en) * | 1998-07-15 | 2001-05-25 | Great Lakes Chemical Europ | Phenylenediamine silanes as antiozonants and antioxidants for rubbers |
| US6794761B2 (en) * | 2001-04-26 | 2004-09-21 | Intel Corporation | No-flow underfill material |
| US7018427B2 (en) | 2001-09-28 | 2006-03-28 | L'oreal S.A. | Dyeing composition containing a para-aminophenol or para-phenylenediamine compound substituted with a silane radical |
| JP2004289102A (en) * | 2003-01-29 | 2004-10-14 | Asahi Kasei Chemicals Corp | Thermosetting composition for sealing light emitting element, and light emitting diode |
| JP2006241084A (en) * | 2005-03-03 | 2006-09-14 | Tokyo Univ Of Science | Surface-modifying agent, cytophilic material, method for producing cytophilic material and, bone-like transplant and method for producing bone-like transplant |
| JPWO2007004345A1 (en) * | 2005-06-30 | 2009-01-22 | 東レ株式会社 | Photosensitive resin composition and adhesion improver |
| US7977028B2 (en) * | 2005-06-30 | 2011-07-12 | Toray Industries, Inc. | Photosensitive resin composition and adhesion promoter |
| JP5087923B2 (en) * | 2005-06-30 | 2012-12-05 | 東レ株式会社 | Photosensitive resin composition and pattern forming method |
| WO2013191203A1 (en) * | 2012-06-20 | 2013-12-27 | 日産化学工業株式会社 | Silicon-containing resist underlayer film-forming composition having sulfone structure and amine structure |
| KR20150021542A (en) * | 2012-06-20 | 2015-03-02 | 닛산 가가쿠 고교 가부시키 가이샤 | Silicon-containing resist underlayer film-forming composition having sulfone structure and amine structure |
| CN104395328A (en) * | 2012-06-20 | 2015-03-04 | 日产化学工业株式会社 | Silicon-containing resist underlayer film-forming composition having sulfone structure and amine structure |
| JPWO2013191203A1 (en) * | 2012-06-20 | 2016-05-26 | 日産化学工業株式会社 | Silicon-containing resist underlayer film forming composition having sulfone structure and amine structure |
| US9494862B2 (en) | 2012-06-20 | 2016-11-15 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition containing silicon having sulfone structure and amine structure |
| CN109879903A (en) * | 2019-01-09 | 2019-06-14 | 青岛科技大学 | One kind is novel to prevent old silane coupling agent and preparation method thereof |
| CN112745483A (en) * | 2021-01-15 | 2021-05-04 | 万华化学集团股份有限公司 | Epoxy resin curing agent, preparation method thereof, epoxy resin composition and application |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0113714B2 (en) | 1989-03-07 |
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