JP3835639B2 - Heat resistant amino-modified silicone emulsion composition - Google Patents
Heat resistant amino-modified silicone emulsion composition Download PDFInfo
- Publication number
- JP3835639B2 JP3835639B2 JP16423097A JP16423097A JP3835639B2 JP 3835639 B2 JP3835639 B2 JP 3835639B2 JP 16423097 A JP16423097 A JP 16423097A JP 16423097 A JP16423097 A JP 16423097A JP 3835639 B2 JP3835639 B2 JP 3835639B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- modified silicone
- carbon atoms
- amino
- 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 - Fee Related
Links
Landscapes
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Colloid Chemistry (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は繊維処理剤、離型剤、艶出剤、潤滑剤として有用である耐熱性の良好なアミノ変性シリコーンエマルジョン組成物に関する。
【０００２】
【従来の技術】
従来より、アミノ変性シリコーンは柔軟剤、離型剤、撥水剤、艶出剤、潤滑剤などの用途に使用されている。これらのアミノ変性シリコーンは、使用時に加熱処理される場合が多く、従って耐熱性が要求されている。シリコーンオイルに酸化防止剤を添加して耐熱性を向上させる（ＵＳＰ−3328350 、特開昭60-106891 号公報、特公平7-37628 号公報参照）方法が知られており、アミノ変性シリコーンに酸化防止剤を添加して耐熱性を向上させる（特公平7-119358号公報参照）方法も知られている。しかし、耐熱性アミノ変性シリコーンエマルジョン組成物については、今まで報告されていない。
【０００３】
【発明が解決しようとする課題】
本発明はアミノ変性シリコーンを主成分とした耐熱性の優れたエマルジョン組成物を提供するものである。
【０００４】
【課題を解決するための手段】
本発明者らは、アミノ変性シリコーンに酸化防止剤及び特定の界面活性剤を添加することにより、アミノ変性シリコーンエマルジョン組成物の耐熱性が格段に向上させられることを見出し、本発明を完成した。
すなわち、本発明は下記（Ａ）〜（Ｃ）成分を水中に乳化分散してなる耐熱性アミノ変性シリコーンエマルジョン組成物である。
（Ａ）下記一般式（化５）で示されるアミノ変性シリコーン 100重量部、
【化５】
（Ｂ）酸化防止剤 0.01〜20重量部、
（Ｃ）ＨＬＢ６〜16の非イオン性界面活性剤 ５〜 100重量部。
【０００５】
【発明の実施の形態】
以下に本発明について詳しく説明する。
まず、本発明における（Ａ）成分の一般式（化１）において式中のＲは同一又は異種の炭素数１〜20のアルキル基又は炭素数６〜20のアリール基であり、具体的にはメチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、テトラデシル基、オクタデシル基、フェニル基、トリル基、ナフチル基等あるいはこれらの炭素原子に結合した水素原子の一部または全部をハロゲン原子、水酸基などで置換した一価の有機基などが挙げられる。好ましくは、メチル基である。次に、Ｘは一般式-Q-(NH-Q')p-NH2 で表されるアミノ基であり、ＱおよびＱ’は同一又は異種の炭素数１〜10の２価有機基であり、具体的にはメチレン基、ジメチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基及びこれらの炭素原子の一部を酸素原子、硫黄原子のような他の原子で置換したもの、これらの炭素原子の有する水素原子の一部又は全部を他のハロゲン原子、水酸基などで置換したもの等があげられる。好ましくは、ジメチレン基またはトリメチレン基である。Ｙは前出のＸ、Ｒまたは炭素数１〜５のアルコキシ基、水酸基のいずれかであり、炭素数１〜５のアルコキシ基としては、メトキシ基、エトキシ基、ブトキシ基、プロポキシ基などがあげられる。ｐは０，１，２のいずれかである。製造面からｐとしては０または１が好ましい。また、10≦ｍ≦10,000、０≦ｎ≦100 であり、好ましくは50≦ｍ≦1,000 、０≦ｎ≦10である。
【０００６】
このようなアミノ変性シリコーンの具体例としては、下記式（化６）〜（化１６）で示される化合物を挙げることができるが、本発明はこれらに限定されるものではない。
【化６】
次に本発明における（Ｂ）成分の酸化防止剤はアミノ基の熱酸化性の劣化を抑制する為に使用するものであり、下記式（化１７）、（化１８）などで示されるヒンダードフェノール類、PhNHPhNHPh、PhNHPh、下記式（化１９）及び（化２０）などで示される芳香族アミン類、ヒンダードフェノール基含有オルガノポリシロキサン、芳香族アミノ基含有オルガノポリシロキサンなどが挙げられるが、特に好ましいものは、アミノ変性シリコーンとの相溶性の面から一般式（化２）で示される芳香族アミノ基含有オルガノポリシロキサンである。
【化１７】
本発明における（Ｂ）成分の添加量としては（Ａ）成分のアミノ変性シリコーン 100重量部に対して0.01〜20重量部である。0.01重量部未満では耐熱性の向上効果が弱く、20重量部を超えて添加しても耐熱性の向上効果は変わらず、かえってシリコーンエマルジョンの安定性が悪くなるため0.01〜20重量部が好ましく、より好ましくは、 0.1〜５重量部である。
【０００９】
次に本発明における（Ｃ）成分のＨＬＢ６〜16の非イオン性界面活性剤は、（Ａ）、（Ｂ）両成分を水中で乳化分散させるための界面活性剤であるが、このＨＬＢが16を超えると得られるシリコーンエマルジョンの耐熱性が不十分なものとなるし、ＨＬＢが６未満であるとシリコーンエマルジョンの乳化安定性が悪くなるため、ＨＬＢは６〜16であることが好ましく、より好ましくは10〜14である。
【００１０】
本発明における（Ｃ）成分の非イオン性界面活性剤の具体例としてはポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンアルキルエーテル、ソルビタン脂肪酸エステル等が挙げられる。中でも乳化安定性の面からポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンアルキルエーテルが好ましい。この添加量は（Ａ）成分のアミノ変性シリコーン 100重量部に対して５〜 100重量部である。５重量部未満ではアミノ変性シリコーンの乳化安定性が悪くなり 100重量部を超えるとアミノ変性シリコーンの特性を阻害する恐れがあるから５〜 100重量部が好ましく、より好ましくは10〜50重量部である。
【００１１】
なお、これらの成分からなるシリコーンエマルジョン組成物にその特性向上のために各種添加剤として帯電防止剤、浸透剤、増粘剤、消泡剤、顔料、無機粉体、防腐剤等を適宜配合することは差し支えない。
【００１２】
【実施例】
以下に実施例により本発明を更に詳細に説明するが、本発明の組成物はこれらによって限定されるものではない。
（実施例１）
下記式（化２１）で示されるアミノ変性シリコーン150g、
【化２１】
【化２２】
この組成物の耐熱性を下記の方法で測定、評価し結果を（表１）に示した。以下の実施例、比較例についてもこの方法により耐熱性を評価した。
【００１３】
［耐熱性の測定、評価方法（ゲル化度）］
アルミシャーレ（直径60mm、深さ10mm）にエマルジョン2.0gを精秤し、 105℃で１時間予備乾燥後、 150℃で24時間加熱した後の残分についてクロロホルムへの不溶分含有率をゲル化度として算出し、耐熱性を評価した。ゲル化度が小さいほど、耐熱性に優れていることを意味する。
【００１４】
（実施例２）
実施例１で使用した式（化２１）で示されるアミノ変性シリコーン150g、式（化２２）で示される芳香族アミノ基含有オルガノポリシロキサン0.5g、乳化剤としてポリオキシエチレンラウリルエーテル［ＥＯ：10モル、ＨＬＢ：14.0］50g 、水800gの混合物を実施例１と同様の方法でホモミキサーで乳化し、さらに高圧ホモジナイザーで２次乳化を行ないエマルジョンを得た。
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００１５】
（実施例３）
下記式（化２３）で示されるアミノ変性シリコーン150g、
【化２３】
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００１６】
（実施例４）
下記式（化２４）で示されるアミノ変性シリコーン150g、
【化２４】
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００１７】
（実施例５）
下記式（化２５）で示されるアミノ変性シリコーン150g、
【化２５】
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００１８】
（実施例６）
下記式（化２６）で示されるアミノ変性シリコーン150g、
【化２６】
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００１９】
（比較例１）
実施例１で使用した式（化２１）で示されるアミノ変性シリコーン150g、式（化２２）で示される芳香族アミノ基含有オルガノポリシロキサン0.5g、乳化剤としてポリオキシエチレンラウリルエーテル［ＥＯ：４モル、ＨＬＢ：9.6 ］15g 、ポリオキシエチレンラウリルエーテル［ＥＯ：23モル、ＨＬＢ：16.9］15g 、水820gの混合物を実施例１と同様にしてホモミキサーで乳化し、さらに高圧ホモジナイザーで２次乳化を行ないエマルジョンを得た。
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００２０】
（比較例２）
実施例１で使用した式（化２１）で示されるアミノ変性シリコーン150g、乳化剤としてポリオキシエチレンラウリルエーテル［ＥＯ：10モル、ＨＬＢ：14.0］15g 、水835gの混合物を実施例１と同様にしてホモミキサーで乳化し、さらに高圧ホモジナイザーで２次乳化を行ないエマルジョンを得た。
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００２１】
（比較例３）
実施例１で使用した式（化２１）で示されるアミノ変性シリコーン150g、式（化２２）で示される芳香族アミノ基含有オルガノポリシロキサン0.1g、乳化剤としてポリオキシエチレンラウリルエーテル［ＥＯ：10モル、ＨＬＢ：14.0］５g 、水845gの混合物を実施例１と同様にしてホモミキサーで乳化し、さらに高圧ホモジナイザーで２次乳化を行ないエマルジョンを得た。
この組成物の耐熱性を測定し、結果を（表１）に示した。
【００２２】
【表１】
【発明の効果】
本発明の耐熱性アミノ変性シリコーンエマルジョン組成物は耐熱性が格段に優れているため、高温での安定性が要求される繊維処理剤、離型剤、艶出剤、潤滑剤などの用途に有用である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an amino-modified silicone emulsion composition having good heat resistance and useful as a fiber treatment agent, a release agent, a polish, and a lubricant.
[0002]
[Prior art]
Conventionally, amino-modified silicones have been used for applications such as softeners, mold release agents, water repellents, polishes, and lubricants. These amino-modified silicones are often heat-treated at the time of use, and therefore heat resistance is required. A method of improving the heat resistance by adding an antioxidant to silicone oil (see USP-3328350, JP-A-60-106891, JP-B-7-37628) is known, and is oxidized to amino-modified silicone. A method for improving the heat resistance by adding an inhibitor (see Japanese Patent Publication No. 7-119358) is also known. However, no heat-resistant amino-modified silicone emulsion composition has been reported so far.
[0003]
[Problems to be solved by the invention]
The present invention provides an emulsion composition having amino-modified silicone as a main component and excellent in heat resistance.
[0004]
[Means for Solving the Problems]
The present inventors have found that the heat resistance of the amino-modified silicone emulsion composition can be remarkably improved by adding an antioxidant and a specific surfactant to the amino-modified silicone, and have completed the present invention.
That is, the present invention is a heat-resistant amino-modified silicone emulsion composition obtained by emulsifying and dispersing the following components (A) to (C) in water.
(A) 100 parts by weight of amino-modified silicone represented by the following general formula (Formula 5)
[Chemical formula 5]
(B) 0.01 to 20 parts by weight of an antioxidant,
(C) 5 to 100 parts by weight of HLB 6 to 16 nonionic surfactant.
[0005]
DETAILED DESCRIPTION OF THE INVENTION
The present invention is described in detail below.
First, in the general formula (Formula 1) of the component (A) in the present invention, R in the formula is the same or different alkyl group having 1 to 20 carbon atoms or aryl group having 6 to 20 carbon atoms, specifically, Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, tetradecyl group, octadecyl group, phenyl group, tolyl group, naphthyl group, etc., or these carbon atoms And monovalent organic groups in which some or all of the hydrogen atoms bonded to are substituted with halogen atoms or hydroxyl groups. Preferably, it is a methyl group. Next, X is an amino group represented by the general formula —Q— (NH—Q ′) p —NH 2 , and Q and Q ′ are the same or different divalent organic groups having 1 to 10 carbon atoms. Specifically, a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a nonamethylene group, a decamethylene group, and a part of these carbon atoms are oxygen atoms. And those substituted with other atoms such as a sulfur atom, and those obtained by substituting some or all of the hydrogen atoms of these carbon atoms with other halogen atoms, hydroxyl groups, and the like. Preferably, it is a dimethylene group or a trimethylene group. Y is any one of the above-mentioned X and R, or an alkoxy group having 1 to 5 carbon atoms and a hydroxyl group. Examples of the alkoxy group having 1 to 5 carbon atoms include a methoxy group, an ethoxy group, a butoxy group, and a propoxy group. It is done. p is either 0, 1, or 2. From the standpoint of production, p is preferably 0 or 1. Further, 10 ≦ m ≦ 10,000 and 0 ≦ n ≦ 100, preferably 50 ≦ m ≦ 1,000 and 0 ≦ n ≦ 10.
[0006]
Specific examples of such amino-modified silicones include compounds represented by the following formulas (Chemical Formula 6) to (Chemical Formula 16), but the present invention is not limited thereto.
[Chemical 6]
Next, the antioxidant of the component (B) in the present invention is used to suppress the deterioration of the thermal oxidation property of the amino group, and is a hindered represented by the following formulas (Chemical Formula 17) Examples include phenols, PhNHPhNHPh, PhNHPh, aromatic amines represented by the following formulas (Chemical Formula 19) and (Chemical Formula 20), hindered phenol group-containing organopolysiloxanes, aromatic amino group-containing organopolysiloxanes, and the like. Particularly preferred is an aromatic amino group-containing organopolysiloxane represented by the general formula (Chemical Formula 2) from the viewpoint of compatibility with amino-modified silicone.
Embedded image
The addition amount of the component (B) in the present invention is 0.01 to 20 parts by weight with respect to 100 parts by weight of the amino-modified silicone of the component (A). If it is less than 0.01 parts by weight, the effect of improving heat resistance is weak, and even if added in excess of 20 parts by weight, the effect of improving heat resistance is not changed, and on the contrary, the stability of the silicone emulsion is deteriorated, so 0.01 to 20 parts by weight is preferable. More preferably, it is 0.1 to 5 parts by weight.
[0009]
Next, the nonionic surfactants HLB6 to 16 as component (C) in the present invention are surfactants for emulsifying and dispersing both components (A) and (B) in water. The heat resistance of the resulting silicone emulsion is insufficient when the amount exceeds 1, and the emulsion stability of the silicone emulsion is deteriorated when the HLB is less than 6. Therefore, the HLB is preferably 6 to 16, more preferably. Is 10-14.
[0010]
Specific examples of the nonionic surfactant of the component (C) in the present invention include polyoxyethylene alkylphenyl ether, polyoxyethylene alkyl ether, sorbitan fatty acid ester and the like. Of these, polyoxyethylene alkylphenyl ether and polyoxyethylene alkyl ether are preferred from the viewpoint of emulsion stability. This addition amount is 5 to 100 parts by weight with respect to 100 parts by weight of the amino-modified silicone as the component (A). If it is less than 5 parts by weight, the emulsification stability of the amino-modified silicone is deteriorated, and if it exceeds 100 parts by weight, the properties of the amino-modified silicone may be impaired, so 5 to 100 parts by weight is preferable, and more preferably 10 to 50 parts by weight. is there.
[0011]
In addition, an antistatic agent, a penetrating agent, a thickener, an antifoaming agent, a pigment, an inorganic powder, an antiseptic, etc. are appropriately added as additives to the silicone emulsion composition comprising these components in order to improve its properties. There is no problem.
[0012]
【Example】
The present invention will be described in more detail with reference to the following examples, but the composition of the present invention is not limited thereto.
Example 1
150 g of amino-modified silicone represented by the following formula (Chemical Formula 21)
Embedded image
Embedded image
The heat resistance of this composition was measured and evaluated by the following method, and the results are shown in Table 1. The heat resistance of the following examples and comparative examples was also evaluated by this method.
[0013]
[Measurement and evaluation method of heat resistance (degree of gelation)]
Weigh accurately 2.0 g of emulsion in an aluminum petri dish (diameter 60 mm, depth 10 mm), and after pre-drying at 105 ° C for 1 hour, heat the residue at 150 ° C for 24 hours to gel the insoluble content in chloroform. It was calculated as a degree to evaluate the heat resistance. The smaller the degree of gelation, the better the heat resistance.
[0014]
(Example 2)
150 g of amino-modified silicone represented by the formula (Chemical Formula 21) used in Example 1, 0.5 g of an aromatic amino group-containing organopolysiloxane represented by the formula (Chemical Formula 22), polyoxyethylene lauryl ether [EO: 10 mol as an emulsifier , HLB: 14.0] A mixture of 50 g and 800 g of water was emulsified with a homomixer in the same manner as in Example 1, and further subjected to secondary emulsification with a high-pressure homogenizer to obtain an emulsion.
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0015]
Example 3
150 g of amino-modified silicone represented by the following formula (Chemical Formula 23)
Embedded image
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0016]
Example 4
150 g of amino-modified silicone represented by the following formula (Chemical Formula 24)
Embedded image
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0017]
(Example 5)
150 g of amino-modified silicone represented by the following formula (Formula 25),
Embedded image
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0018]
(Example 6)
150 g of amino-modified silicone represented by the following formula (Chemical Formula 26)
Embedded image
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0019]
(Comparative Example 1)
150 g of amino-modified silicone represented by the formula (Chemical Formula 21) used in Example 1, 0.5 g of an aromatic amino group-containing organopolysiloxane represented by the formula (Chemical Formula 22), polyoxyethylene lauryl ether [EO: 4 mol as an emulsifier , HLB: 9.6] 15 g, polyoxyethylene lauryl ether [EO: 23 mol, HLB: 16.9] 15 g, and water 820 g were emulsified with a homomixer in the same manner as in Example 1 and further subjected to secondary emulsification with a high-pressure homogenizer. And an emulsion was obtained.
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0020]
(Comparative Example 2)
In the same manner as in Example 1, a mixture of 150 g of amino-modified silicone represented by the formula (Chemical Formula 21) used in Example 1, 15 g of polyoxyethylene lauryl ether [EO: 10 mol, HLB: 14.0] as an emulsifier, and 835 g of water was used. The mixture was emulsified with a homomixer and further subjected to secondary emulsification with a high-pressure homogenizer to obtain an emulsion.
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0021]
(Comparative Example 3)
150 g of an amino-modified silicone represented by the formula (Chemical Formula 21) used in Example 1, 0.1 g of an aromatic amino group-containing organopolysiloxane represented by the formula (Chemical Formula 22), polyoxyethylene lauryl ether [EO: 10 mol as an emulsifier , HLB: 14.0] and a mixture of 5 g of water and 845 g of water were emulsified with a homomixer in the same manner as in Example 1, followed by secondary emulsification with a high-pressure homogenizer to obtain an emulsion.
The heat resistance of this composition was measured, and the results are shown in Table 1.
[0022]
[Table 1]
【The invention's effect】
Since the heat-resistant amino-modified silicone emulsion composition of the present invention is remarkably excellent in heat resistance, it is useful for applications such as fiber treatment agents, mold release agents, polishes, and lubricants that require stability at high temperatures. It is.
Claims (1)
（Ａ）下記一般式（化１）で示されるアミノ変性シリコーン 100重量部、
（Ｂ）下記一般式（化２）で示される芳香族アミノ基含有オルガノポリシロキサンからなる酸化防止剤 0.01〜20重量部、
(A) 100 parts by weight of an amino-modified silicone represented by the following general formula (Formula 1)
(B) 0.01 to 20 parts by weight of an antioxidant comprising an aromatic amino group-containing organopolysiloxane represented by the following general formula (Formula 2) :
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16423097A JP3835639B2 (en) | 1997-06-20 | 1997-06-20 | Heat resistant amino-modified silicone emulsion composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16423097A JP3835639B2 (en) | 1997-06-20 | 1997-06-20 | Heat resistant amino-modified silicone emulsion composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1112286A JPH1112286A (en) | 1999-01-19 |
| JP3835639B2 true JP3835639B2 (en) | 2006-10-18 |
Family
ID=15789153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16423097A Expired - Fee Related JP3835639B2 (en) | 1997-06-20 | 1997-06-20 | Heat resistant amino-modified silicone emulsion composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3835639B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4854872B2 (en) * | 2001-06-20 | 2012-01-18 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Water repellent polish |
| JP4716043B2 (en) * | 2007-09-21 | 2011-07-06 | 信越化学工業株式会社 | Room temperature curable organopolysiloxane composition |
| JP5829965B2 (en) * | 2012-03-29 | 2015-12-09 | Ｊｘ日鉱日石エネルギー株式会社 | Succinimide compound, lubricating oil additive and lubricating oil composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0647787B2 (en) * | 1985-08-14 | 1994-06-22 | 日華化学株式会社 | Silicone fiber treatment agent |
| JPS6461576A (en) * | 1987-08-27 | 1989-03-08 | Lion Corp | Gloss preventing composition |
| US5132443A (en) * | 1990-10-02 | 1992-07-21 | General Electric Company | Aminofunctional silicone compositions and methods of use |
| JP3624262B2 (en) * | 1997-04-11 | 2005-03-02 | 信越化学工業株式会社 | Textile treatment composition |
| JP3449886B2 (en) * | 1997-06-02 | 2003-09-22 | 信越化学工業株式会社 | Film-forming composition and cosmetic using the same |
| JP3949777B2 (en) * | 1997-06-20 | 2007-07-25 | 三菱レイヨン株式会社 | Carbon fiber precursor acrylic fiber |
-
1997
- 1997-06-20 JP JP16423097A patent/JP3835639B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1112286A (en) | 1999-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6878770B2 (en) | Aqueous organosilicon compositions | |
| JP2821494B2 (en) | Polydiorganosiloxane, process for producing the same, and fiber coating agent containing the same | |
| KR101594929B1 (en) | Organo-functional silicone in emulsion systems and process for preparing same | |
| JPS61155449A (en) | Siloxane composition | |
| US5496401A (en) | Aqueous emulsion containing an oxidatively crosslinked aminopolysiloxane | |
| US4125470A (en) | Band-ply lubricant concentrates | |
| JP2001139690A (en) | Fluorine-containing polysiloxane, its production method, and fiber treating agent composition | |
| JPH0711000A (en) | Preparation of organopolysiloxane | |
| US4537691A (en) | Silicone-based working fluid composition | |
| US4045390A (en) | Silicone rubber compositions | |
| JP3835639B2 (en) | Heat resistant amino-modified silicone emulsion composition | |
| CA1253655A (en) | Stabilized blends of thiofunctional polysiloxane fluids and organopolysiloxane fluids and a process for stabilizing the same | |
| CA2013012A1 (en) | Ultraviolet cured gels with controlled modulus and viscosity | |
| US6417310B1 (en) | Method for preparing branched organopolysiloxane | |
| US7396872B2 (en) | Greasy silicone composition | |
| KR19980071047A (en) | How to stabilize siloxane polymers | |
| JP3978566B2 (en) | Process for producing branched organopolysiloxane emulsion | |
| JPH0480078B2 (en) | ||
| US4515702A (en) | Heat-resistant silicone fluid compositions | |
| US5445751A (en) | Fluorosilicone lubricant compositions | |
| US5036114A (en) | Acrylamide polysiloxane composition with improved heat stability | |
| JP2021121684A (en) | Organosilicone emulsion composition | |
| US4460726A (en) | Method for stabilizing organopolysiloxanes | |
| JPS60248732A (en) | Organopolysiloxane latex containing phosphoric acid ester group | |
| US5356549A (en) | Silicone grease |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060405 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060530 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20060530 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060719 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20060720 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090804 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120804 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150804 Year of fee payment: 9 |
|
| LAPS | Cancellation because of no payment of annual fees |