JPH03258866A - Fine particle coated with polydimethylsiloxane - Google Patents
Fine particle coated with polydimethylsiloxaneInfo
- Publication number
- JPH03258866A JPH03258866A JP2056086A JP5608690A JPH03258866A JP H03258866 A JPH03258866 A JP H03258866A JP 2056086 A JP2056086 A JP 2056086A JP 5608690 A JP5608690 A JP 5608690A JP H03258866 A JPH03258866 A JP H03258866A
- Authority
- JP
- Japan
- Prior art keywords
- fine particles
- polydimethylsiloxane
- silica
- coated
- group
- 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.)
- Pending
Links
- 239000010419 fine particle Substances 0.000 title claims abstract description 92
- -1 polydimethylsiloxane Polymers 0.000 title claims abstract description 56
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 title claims abstract description 55
- 239000004205 dimethyl polysiloxane Substances 0.000 title claims abstract description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 229910002808 Si–O–Si Inorganic materials 0.000 claims abstract 2
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 14
- 239000003125 aqueous solvent Substances 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 238000001962 electrophoresis Methods 0.000 abstract description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 45
- 239000006185 dispersion Substances 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 14
- 230000002776 aggregation Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000004220 aggregation Methods 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011859 microparticle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000132059 Carica parviflora Species 0.000 description 1
- 235000014653 Carica parviflora Nutrition 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 241000600169 Maro Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、ポリジメチルシロキサン被覆微粒子に関する
。さらに詳しくは、非水溶媒中で非常に安定な分散安定
性を示すポリジメチルシロキサン被覆微粒子に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to polydimethylsiloxane-coated fine particles. More specifically, the present invention relates to polydimethylsiloxane-coated fine particles that exhibit very stable dispersion stability in non-aqueous solvents.
〔従来の技術］
非水溶媒中で固体微粒子の安定な分散状態をうるために
は、２つの因子を考える必要がある。[Prior Art] In order to obtain a stable dispersion state of solid fine particles in a non-aqueous solvent, it is necessary to consider two factors.
その１つは、電気二重層間の静電反発力であり、もう１
つは、ポリマー吸着層間の立体障害である。One is the electrostatic repulsion between electric double layers, and the other is
One is steric hindrance between polymer adsorption layers.
一般に比較的誘電率が小さい非水溶媒を用いるばあいに
は、イオン解離が起こりにくいため、前記静電反発力は
比較的小さいことから、前記立体障害を考慮することが
重要となる。In general, when a non-aqueous solvent having a relatively low dielectric constant is used, ion dissociation is difficult to occur and the electrostatic repulsion is relatively small, so it is important to consider the steric hindrance.
微粒子を非水溶媒中に分散させる一般的な方法としては
、界面活性剤およびポリマーを微粒子表面に吸着させる
方法がある。かかる方法については現在までに数えきれ
ないほどの多くの研究かなされており、微粒子および分
散媒の種類に応じて界面活性剤および吸着ポリマーを選
ぶことによって分散性がかなり改善されることがわかっ
ている。A common method for dispersing fine particles in a nonaqueous solvent is to adsorb a surfactant and a polymer onto the surface of the fine particles. Numerous studies have been conducted on this method to date, and it has been found that dispersibility can be significantly improved by selecting surfactants and adsorbing polymers depending on the type of fine particles and dispersion medium. There is.
他方、微粒子がカーボンブラックであるばあいには、そ
の表面にポリマーを化学結合させること（以下、グラフ
ト化という）により、該カーボンブラックの分散性を向
上させることがふるくから行なわれている。On the other hand, when the fine particles are carbon black, the dispersibility of the carbon black is improved by chemically bonding a polymer to its surface (hereinafter referred to as grafting).
また最近、坪用らは、ポリアクリルアミドなとのポリマ
ーを酸化物微粒子表面にグラフト化させることにより、
水中で安定な分散系かえられることを報告している（「
第２回コロイドおよび界面化学特別討論会要旨集Ｊ
（１９８７）日本化学会コロイドおよび界面化学部会、
ｐ、１１１）。Recently, Tsuboyoshi et al. have also grafted polymers such as polyacrylamide onto the surface of oxide particles.
It has been reported that a stable dispersion system can be transformed in water ("
Abstracts of the 2nd Special Conference on Colloid and Surface Chemistry J
(1987) Colloid and Surface Chemistry Division, Chemical Society of Japan,
p. 111).
［発明か解決しようとする課題］
一般に物理的変化は、熱力学的にいえば全自由エネルギ
ーを減少させる方向に起こるから、分散系においては界
面自由エネルギーが一定のばあいには、界面の面積を減
らす方向の変化、すなわち粒子の凝集が起こる。一方、
吸着性のポリマーなどが存在するばあいには、吸着によ
り界面自由エネルギーが減少することから、ある程度、
凝集を抑制することが可能となる。それゆえ、従来、微
粒子を非水溶媒中に分散させるばあいには、各種の界面
活性剤およびポリマーが分散剤として用いられているが
、これらのほとんどすべては分散剤の微粒子への物理吸
着を利用したものである。しかしながら、その吸着力は
小さいため、分散剤は微粒子から脱着しやすく、長期間
にわたる分散安定性かえられず、またその分散安定性は
温度の影響を受けやすいという問題があった。[Invention or problem to be solved] In general, physical changes occur in the direction of decreasing the total free energy thermodynamically speaking, so in a dispersed system, if the interfacial free energy is constant, the area of the interface A change in direction that reduces the amount of particles occurs, i.e., particle agglomeration. on the other hand,
In the presence of adsorbent polymers, interfacial free energy decreases due to adsorption, so to some extent,
It becomes possible to suppress aggregation. Therefore, when dispersing fine particles in a non-aqueous solvent, various surfactants and polymers have been used as dispersants, but almost all of these have the ability to inhibit the physical adsorption of the dispersant onto the fine particles. It was used. However, since its adsorption power is small, the dispersant is easily desorbed from the fine particles, and long-term dispersion stability cannot be improved, and the dispersion stability is easily affected by temperature.
また、金属や金属酸化物などの比重の大きい微粒子を分
散させるばあいには、微粒子同士の凝集以外に微粒子が
沈降するという問題が生じる。Further, when dispersing fine particles having a high specific gravity such as metals or metal oxides, a problem arises in that the fine particles not only aggregate with each other but also settle.
これに対して、グラフト化された微粒子は、ポリマーか
微粒子表面に共有結合により結合されたものであるため
、微粒子とポリマーとの結合力が非常に大きいという特
徴を有し、さらにグラフト化されているので、かかる微
粒子の見かけ比重が小さいから、沈降に対しても非常に
有効である。On the other hand, since grafted fine particles are covalently bonded to the surface of a polymer or fine particles, they have a characteristic that the bonding force between the fine particles and the polymer is extremely large. Since the apparent specific gravity of such fine particles is small, it is very effective against sedimentation.
しかしながら、従来のグラフト化された微粒子としては
両末端に官能基を有するポリマーによりグラフト化され
たものが用いられており、その一部のポリマーが、微粒
子同士の架橋剤としてのはたらきを有するため、逆に凝
集を促進するという問題があった。However, as conventional grafted fine particles, those grafted with a polymer having functional groups at both ends are used, and some of the polymers act as a cross-linking agent between the fine particles. On the contrary, there was a problem of promoting aggregation.
このように、微粒子へのポリマーのグラフト化は、前記
のごとく、ポリマーと微粒子との結合力が大きいことか
ら、グラフト化に用いられるポリマーによる微粒子同士
の架橋作用をなくすことがてきれば、微粒子の分散安定
化の非常に有効な手段となると考えられる。In this way, grafting of a polymer onto fine particles is possible because, as mentioned above, the bonding force between the polymer and the fine particles is large. This is considered to be a very effective means of stabilizing the dispersion of.
そこで、本発明者らは、前記問題点に鑑みて鋭意研究を
重ねた結果、片末端にのみ官能基を有するポリジメチル
シロキサンで微粒子が付着された被覆微粒子を用いたば
あいには、非水溶媒中における微粒子の分散安定性が著
しく向上することを見出し、本発明を完成するにいたっ
た。Therefore, the present inventors have conducted extensive research in view of the above-mentioned problems, and have found that when coated fine particles are attached with polydimethylsiloxane having a functional group only at one end, non-aqueous It was discovered that the dispersion stability of fine particles in a solvent was significantly improved, and the present invention was completed.
［課題を解決するための手段］
すなわち、本発明は、−数式（Ｉ）：
（式中、ｎは５〜１００の整数、飄は１〜３の整数、Ｘ
はヒドロキシル基または加水分解性基を示す）で表わさ
れるポリジメチルシロキサンと少なくともその表面がシ
リカからなる微粒子の表面に存在するヒドロキシル基と
の反応により、ポリジメチルシロキサンが５ｉ−０−８
ｉ結合で該微粒子に付着されてなるポリジメチルシロキ
サン被ｍ微粒子に関する。[Means for Solving the Problems] That is, the present invention provides - Formula (I): (where n is an integer of 5 to 100, 飄 is an integer of 1 to 3,
represents a hydroxyl group or a hydrolyzable group) and the hydroxyl group present on the surface of the fine particles at least the surface of which is made of silica, the polydimethylsiloxane becomes 5i-0-8.
The present invention relates to polydimethylsiloxane-covered microparticles which are attached to the microparticles through i-bonds.
［作用および実施例コ
本発明のポリジメチルシロキサン被覆微粒子は、片末端
に少なくとも１個のヒドロキシル基または加水分解性基
を有するポリジメチルシロキサンと少なくともその表面
がシリカからなる微粒子の表面に存在するヒドロキシル
基との反応により、該ポリジメチルシロキサンが５ｊ−
０−８ｉ結合により該微粒子に付着されたものである。[Function and Examples] The polydimethylsiloxane-coated fine particles of the present invention consist of polydimethylsiloxane having at least one hydroxyl group or hydrolyzable group at one end and hydroxyl present on the surface of the fine particles, the surface of which is made of silica. By reaction with the group, the polydimethylsiloxane becomes 5j-
It is attached to the fine particles by a 0-8i bond.
本発明に用いられるポリジメチルシロキサンは、一般式
（Ｉ）：
（式中、ｎは５〜ｌｏＯの整数、口は１〜３の整数、Ｘ
はヒドロキシル基または加水分解性基を示す）で表わさ
れ、片末端に少なくとも１個のヒドロキシル基または加
水分解性基を有するものである。The polydimethylsiloxane used in the present invention has the general formula (I): (wherein, n is an integer of 5 to loO,
represents a hydroxyl group or a hydrolyzable group), and has at least one hydroxyl group or hydrolyzable group at one end.
前記一般式（１）において、ｎは前記したごとく、５〜
１００の整数であるが、とくにｌＯ〜５０の整数である
ことが好ましい。ｎは １００をこえるばあいには、微
粒子上に固定されるポリジメチルシロキサンのモル数が
著しく減少し、また５未満であるばあいには、異なるポ
リジメチルシロキサン被覆微粒子上のポリジメチルシロ
キサン間の容積制限効果による反発エネルギーが減少す
る。なお、いずれのばあいにも、その分散安定化効果は
著しく低下する。In the general formula (1), n is 5 to 5, as described above.
It is an integer of 100, and particularly preferably an integer of 10 to 50. When n exceeds 100, the number of moles of polydimethylsiloxane fixed on the fine particles decreases significantly, and when n is less than 5, the number of moles of polydimethylsiloxane fixed on the fine particles coated with different polydimethylsiloxanes decreases. Repulsion energy due to volume restriction effect is reduced. In either case, the dispersion stabilizing effect is significantly reduced.
また、前記Ｘは、ポリジメチルシロキサンの官能基とし
て、シリカ表面に存在するヒドロキシル基と反応するも
のであり、前記のごとく、ヒドロキシル基または加水分
解性基である。かかる加水分解性基としては、たとえば
アミノ基、アルコキシル基、アセチルアセトナト基など
があげられる。前記Ｘは、シリカ表面に存在するヒドロ
キシル基との反応性が高いという点で、ヒドロキシル基
、メトキシ基、エトキシ基およびアミノ基よりなる群か
ら選ばれた少なくとも１種であることがとくに好ましい
。Moreover, the above-mentioned X is a functional group of polydimethylsiloxane that reacts with a hydroxyl group present on the silica surface, and is a hydroxyl group or a hydrolyzable group as described above. Examples of such hydrolyzable groups include amino groups, alkoxyl groups, and acetylacetonato groups. The X is particularly preferably at least one selected from the group consisting of a hydroxyl group, a methoxy group, an ethoxy group, and an amino group in terms of its high reactivity with the hydroxyl group present on the silica surface.
本発明に用いられる片末端に官能基を有するポリジメチ
ルシロキサンは、末端の８１原子に直接前記官能基が結
合している。したがって、グラフト化により前記ポリジ
メチルシロキサンは、少なくともその表面がシリカから
なる微粒子に、５ｉ−０−３ｉ結合で付着されることか
ら、えられるポリジメチルシロキサン被覆微粒子は加水
分解を受けにくいという特徴を有するものとむる。In the polydimethylsiloxane having a functional group at one end used in the present invention, the functional group is directly bonded to 81 atoms at the end. Therefore, by grafting, the polydimethylsiloxane is attached to the fine particles whose surface is at least made of silica through 5i-0-3i bonds, so the resulting polydimethylsiloxane-coated fine particles have the characteristic of being resistant to hydrolysis. Take what you have.
本発明に用いられる微粒子は、少なくとも表面がシリカ
からなるものであればとくに限定はないが、その具体例
としては、たとえばシリカまたはシリカで表面が被覆さ
れたチタニア、アルミナ、酸化鉄などの微粒子があげら
れる。The fine particles used in the present invention are not particularly limited as long as at least the surface is made of silica, but specific examples include fine particles of silica or titania, alumina, iron oxide, etc. whose surfaces are coated with silica. can give.
前記微粒子をシリカで被覆する方法としては、たとえば
シリカゲルを飽和させたケイフッ化水素酸水溶戒からの
析出法、いわゆる液相成膜法（たとえばＪ、 Ｊｐｎ、
Ｓｏｃ、 Ｃｏ１ｏｕｒ Ｍａｔｅｒｉａｌ、 ６１
［１２］ （１９８８）ｐ、６６５参照）などの方法が
あげられる。なお、かかる被覆された表面上のシリカの
厚さにはとくに限定はないが、通常２０〜１００ムであ
ることが好ましい。The method for coating the fine particles with silica includes, for example, a precipitation method from a hydrofluorosilicic acid solution saturated with silica gel, a so-called liquid phase film formation method (for example, J, Jpn,
Soc, Co1our Material, 61
[12] (1988) p. 665). The thickness of the silica on the coated surface is not particularly limited, but it is usually preferably 20 to 100 μm.
前記少なくともその表面がシリカからなる微粒子の平均
粒径にはとくに限定はないが、好ましくは分散安定性を
向上させる効果が大きいという点でサブミクロン（１−
以下）であることが望ましい。There is no particular limitation on the average particle diameter of the fine particles whose surface is made of silica, but it is preferably submicron (1-
below) is desirable.
前記ポリジメチルシロキサンを前記少なくともその表面
がシリカからなる微粒子に付着させる方法にはとくに限
定はないが、その−例をあげれば、たとえば前記微粒子
をポリジメチルシロキサンに添加し、混合撹拌すること
により懸濁液とし、該懸濁液を撹拌しながらポリジメチ
ルシロキサンと微粒子表面のシリカを反応させたのち、
洗浄、乾燥することにより、ポリジメチルシロキサンを
付着させる方法などがあげられる。There are no particular limitations on the method for attaching the polydimethylsiloxane to the fine particles at least the surface of which is made of silica, but for example, the fine particles may be added to polydimethylsiloxane and mixed and stirred. After forming a suspension into a suspension and reacting the polydimethylsiloxane with the silica on the surface of the fine particles while stirring the suspension,
Examples include a method of attaching polydimethylsiloxane by washing and drying.
前記反応においては、温度は１００〜２５０℃、好まし
くは１５０〜２００℃、また反応時間は２時間以上であ
ることが望ましい。前記温度が１００℃未満であるばあ
いおよび反応時間が２時間未満であるばあいには、えら
れるポリジメチルシロキサン被覆微粒子の非水溶媒中で
の分散安定性が低下する傾向があり、また前記温度が２
５０℃をこえるばあいには、ポリジメチルシロキサンの
熱分Ｍ反応が起こる傾向がある。In the reaction, the temperature is preferably 100 to 250°C, preferably 150 to 200°C, and the reaction time is preferably 2 hours or more. When the temperature is less than 100°C and the reaction time is less than 2 hours, the dispersion stability of the obtained polydimethylsiloxane-coated fine particles in a non-aqueous solvent tends to decrease, and the above-mentioned temperature is 2
If the temperature exceeds 50°C, there is a tendency for a thermal M reaction of polydimethylsiloxane to occur.
また、前記乾燥の方法にはとくに限定はないが、たとえ
ば真空乾燥機などを用いて５０〜１００℃で乾燥する方
法などがあげられる。Further, the drying method is not particularly limited, but examples thereof include a method of drying at 50 to 100° C. using a vacuum dryer or the like.
本発明において、前記ポリジメチルシロキサンの付着量
は、微粒子に対して１重量％以上、好ましくは２重量％
以上となるように調整される。かかる付着量が１重量％
未満であるばあいには、異なるポリジメチルシロキサン
被覆微粒子上のポリジメチルシロキサン間の反発作用が
減少する。また、前記付着量は前記反発作用の点から多
いほど好ましいが、その上限はポリジメチルシロキサン
の分子量、微粒子の表面上に存在するヒドロキシル基の
量などによって異なるため、−概には決定することはで
きない。In the present invention, the amount of the polydimethylsiloxane adhered to the fine particles is 1% by weight or more, preferably 2% by weight.
Adjustments are made so that the above is achieved. Such adhesion amount is 1% by weight.
If it is less than 1, the repulsion between polydimethylsiloxanes on different polydimethylsiloxane-coated fine particles is reduced. Further, from the point of view of the repulsion, it is preferable that the amount of adhesion be as large as possible; however, the upper limit cannot be determined in general because it varies depending on the molecular weight of polydimethylsiloxane, the amount of hydroxyl groups present on the surface of the fine particles, etc. Can not.
かくしてえられる本発明のポリジメチルシロキサン被覆
微粒子は、以下に述べる作用により、たとえばポリジメ
チルシロキサン、トルエン、ｎ−ヘキサン、クロロホル
ムなどの非水溶媒中で長期的に良好な分散安定性を示す
が、とくにポリジメチルシロキサン中における分散性に
すぐれたものである。The thus obtained polydimethylsiloxane-coated fine particles of the present invention exhibit good long-term dispersion stability in nonaqueous solvents such as polydimethylsiloxane, toluene, n-hexane, and chloroform due to the effects described below. It has particularly excellent dispersibility in polydimethylsiloxane.
■ 被覆されたポリジメチルシロキサンのエントロピー
斥力により、ポリジメチルシロキサン被覆微粒子は非水
溶媒中での分散状態が安定化される。(2) Due to the entropic repulsion of the coated polydimethylsiloxane, the dispersion state of the polydimethylsiloxane-coated fine particles in the non-aqueous solvent is stabilized.
■ ポリジメチルシロキサンで被覆されることにより、
微粒子表面が疎水化されエンタルピー的な斥力かえられ
る。■ By coating with polydimethylsiloxane,
The surface of the fine particles is made hydrophobic and the enthalpic repulsion is changed.
■ 片末端に官能基を有するポリマーが用いられるため
に、微粒子同士の架橋作用による凝集を防ぐことができ
る。(2) Since a polymer having a functional group at one end is used, aggregation of fine particles due to crosslinking can be prevented.
■ 微粒子の比重を見かけ上小さくすることができるの
で、金属や金属酸化物などの比重の大きな微粒子をたと
えばポリジメチルシロキサンなどに分散させるばあいで
あっても、その沈降を抑制することができる。(2) Since the apparent specific gravity of fine particles can be reduced, sedimentation of fine particles such as metals and metal oxides with high specific gravity can be suppressed even when dispersed in, for example, polydimethylsiloxane.
■ 用いられる微粒子の少むくとも表面がシリカである
ので、ポリジメチルシロキサンが微粒子上に５ｉ−０−
３ｉ結合により付着されることから、ポリジメチルシロ
キサン被覆微粒子は加水分解を受けにくい。■ Since the surface of the fine particles used is silica, polydimethylsiloxane is coated on the fine particles with 5i-0-
Because they are attached through 3i bonds, polydimethylsiloxane-coated microparticles are less susceptible to hydrolysis.
したがって、本発明のポリジメチルシロキサンｍ覆微粒
子は、非水系の溶媒に分散させることにより、塗料、化
粧料の分野はいうに及ばず、長期にわたる分散安定性を
要求される電気泳動を利用した表示素子（たとえば、特
開昭４８−３１０９６号明細書を参照）および異方性双
極子微粒子の懸濁液からなる電気光学素子（以下、ＤＰ
Ｓ素子という）（たとえば、Ａ、Ｍ、Ｍａｒｋｓ。Therefore, by dispersing the polydimethylsiloxane m-coated particles of the present invention in a non-aqueous solvent, they can be used not only in the fields of paints and cosmetics, but also in displays using electrophoresis that require long-term dispersion stability. (for example, see Japanese Patent Application Laid-Open No. 48-31096) and an electro-optical element (hereinafter referred to as DP
S element) (for example, A, M, Marks).
＾ｐｐｌｉｅｄ ０ｐｔｉｅｓ、８．Ｎｏ、７ （１９
６９）参照）に、とくに有効に用いられる。＾pplied 0pties, 8. No. 7 (19
69)), it is particularly effectively used.
本発明のポリジメチルシロキサン被覆微粒子を分散させ
た懸濁液を表示素子として使用するばあいには、懸濁液
の合計量１００部（重量部、以下同様）に対して１〜２
０部、好ましくは５〜ＩＯ部の該微粒子を分散させて使
用することが望ましい。When the suspension in which the polydimethylsiloxane-coated fine particles of the present invention are dispersed is used as a display element, 1 to 2
It is desirable to use 0 parts, preferably 5 to IO parts of the fine particles dispersed.
また、本発明のポリジメチルシロキサン被覆微粒子を分
散させた！＠濁液をＤＰＳ素子として使用するばあいに
は、懸濁液の合計ｆｆｉ １００部に対して１〜２０部
、好ましくは５〜１０部の該微粒子を分散させて使用す
ることが望ましい。Moreover, the polydimethylsiloxane-coated fine particles of the present invention were dispersed! When the suspension is used as a DPS device, it is desirable to use 1 to 20 parts, preferably 5 to 10 parts, of the fine particles dispersed in 100 parts of the total ffi of the suspension.
つぎに、本発明を実施例に基づいて詳細に説明するが、
本発明はかかる実施例に限定されるものではｌい。Next, the present invention will be explained in detail based on examples.
The present invention is not limited to such embodiments.
実施例１〜４
液相成膜法（ＬＰＤ法）にしたがって、２．５ｍｏｌｄ
ｉ−’のシリカ飽和ケイフッ化水素酸溶液１００ｍ１に
０．５ｍｏｌ ｄｔｎ−３のホウ酸３ ｍｌを添加する
ことにより、５１０２−被覆用処理液を調製した。この
処理液を室温（２０℃）で３０分間攪拌したのち、その
５ ｍｌをポリプロピレン製の試験管に入れて５０℃に
保温した恒温槽に浸漬した。処理液の温度が一定になっ
てから、チタニア微粒子２００ｍｇを添加し、マグネチ
ックスクーラーで攪拌しながら３〜５時間処理した。処
理後、遠心分離を行ない、蒸留水で洗浄した。この洗浄
操作を３回繰り返したのちに、１００℃で２０時間乾燥
させることにより、シリカで被覆されたチタニア微粒子
（平均粒径： ０．２ Ｊｆｆｉ、シリカの被覆厚＝０
．０１ 珊）の粉末をえた。かかる粉末２００ｍｇヲ式
：
で表わされるポリジメチルシロキサン（以下、Ｘ−ＰＤ
Ｓという）２０ｆに添加した。そののち、室温で１５分
間ウルトラディスパーサ−（ヤマト科学■製、ＬＫ−２
２）で撹拌することにより、前記チタニア微粒子の粉末
をＸ−ＰＤＳ中に分散させ、懸濁液をえた。この懸濁液
を前記ウルトラディスパーサ−で撹拌しながら、室温（
実施例１）、１００℃（実施例２）、１５０℃（実施例
３）、２００℃（実施例４）にて前記Ｘ−ＰＤＳと微粒
子表面のシリカを２時間それぞれ反応させることにより
、Ｘ−ＰＤＳが付着された微粒子をえた。Examples 1 to 4 2.5 mold according to liquid phase deposition method (LPD method)
A 5102-coating treatment solution was prepared by adding 3 ml of 0.5 mol dtn-3 boric acid to 100 ml of a silica-saturated hydrofluorosilicic acid solution of i-'. After stirring this treatment solution at room temperature (20°C) for 30 minutes, 5 ml of the solution was placed in a polypropylene test tube and immersed in a constant temperature bath kept at 50°C. After the temperature of the treatment liquid became constant, 200 mg of titania fine particles were added, and the treatment was continued for 3 to 5 hours while stirring with a magnetic cooler. After treatment, it was centrifuged and washed with distilled water. After repeating this washing operation three times, the titania particles coated with silica (average particle size: 0.2 Jffi, silica coating thickness = 0) were dried at 100°C for 20 hours.
．． 01 Coral) powder was obtained. 200 mg of such powder is polydimethylsiloxane (hereinafter referred to as X-PD) represented by the formula:
(referred to as S) was added to 20f. After that, use Ultra Disperser (LK-2, manufactured by Yamato Kagaku ■) for 15 minutes at room temperature.
By stirring in step 2), the titania fine particle powder was dispersed in X-PDS to obtain a suspension. This suspension was stirred with the ultra disperser at room temperature (
X- Fine particles to which PDS was attached were obtained.
えられた微粒子を約１４０ｍ１のトルエンで５回洗浄し
たのちに、真空乾燥機中で５０℃にて２０時間以上加熱
することによって乾燥させた。この微粒子を重量平均分
子量２５００のポリジメチルシロキサン中に分散させて
懸濁液をえた。かかる懸濁液の濁度の経時変化より、微
粒子の凝集速度定数を求めた。その結果を第１表に示す
。なお、この凝集速度定数は、凝集が２次反応速度式に
したがうことを確認したうえで、式：ｌ ／τ −ｌ
／τ ＋ｋｔ
（式中、τおよびτ は、それぞれ時間１−１およびｔ
−ｏにおける濁度、ｋは凝集速度定数を示す）により求
めた。The obtained fine particles were washed five times with about 140 ml of toluene, and then dried by heating at 50° C. for 20 hours or more in a vacuum dryer. These fine particles were dispersed in polydimethylsiloxane having a weight average molecular weight of 2,500 to obtain a suspension. The aggregation rate constant of the fine particles was determined from the change in turbidity of the suspension over time. The results are shown in Table 1. In addition, this aggregation rate constant is determined by the formula: l /τ −l after confirming that aggregation follows the second-order reaction rate equation.
/τ +kt (where τ and τ are time 1-1 and t, respectively)
The turbidity at -o, k indicates the aggregation rate constant).
なお、拡散反射ＦＴ−ＩＲ法による微粒子へのＸ−ＰＤ
Ｓの被覆量の測定結果を第１表に併せて示す。In addition, X-PD on fine particles by diffuse reflection FT-IR method
The measurement results of the S coating amount are also shown in Table 1.
また、実施例３で作製されたポリジメチルシロキサン被
覆微粒子の拡散反射ＦＴ−１１？スペクトルをＸＢｒ法
で測定した。測定されたスペクトルを第１図に示す。Moreover, the diffuse reflection of the polydimethylsiloxane-coated fine particles produced in Example 3 FT-11? The spectrum was measured by the XBr method. The measured spectrum is shown in FIG.
比較例１
実施例１〜４で用いられたシリカで被覆されたチタニア
微粒子をＸ−ＰＤＳで付着しなかったほかは、実施例１
〜４と同様にしてポリジメチルシロキサン中に分散され
たチタニア微粒子の凝集速度定数を求めた。その結果を
第１表に示す。Comparative Example 1 Example 1 except that the silica-coated titania fine particles used in Examples 1 to 4 were not attached with X-PDS.
The aggregation rate constant of titania fine particles dispersed in polydimethylsiloxane was determined in the same manner as in 4. The results are shown in Table 1.
［以下余白］
第 １ 表
第１表に示された結果から、反応温度が高いほど、えら
れるポリジメチルシロキサン被覆微粒子のＸ−ＰＤＳの
付着量が大きくなり、それにしたがって、凝集速度定数
が小さくなること、すなわち分散安定性がよくなること
がわかる。とくに、Ｘ−ＰＤＳの付Ｍ量が微粒子に対し
て１重量％以上の範囲で分散安定性が著しく向上するこ
とがわかる。[Left below] Table 1 From the results shown in Table 1, it can be seen that the higher the reaction temperature, the larger the amount of X-PDS attached to the resulting polydimethylsiloxane-coated fine particles, and the smaller the aggregation rate constant accordingly. In other words, it can be seen that the dispersion stability is improved. In particular, it can be seen that the dispersion stability is significantly improved when the amount of M attached to X-PDS is 1% by weight or more based on the fine particles.
また、第１図（７） ２９８８ｃｍ−１ノ吸収は、Ｘ−
ＰＤＳ ツメチル基のＣ−Ｈ伸縮振動に基づくものであ
ることから、Ｘ−ＰＤＳが微粒子表面に結合しているこ
とが確認された。In addition, the absorption at 2988 cm-1 in Figure 1 (7) is
It was confirmed that X-PDS was bonded to the surface of the fine particles because it was based on the C-H stretching vibration of the PDS trimethyl group.
実施例５〜７
一般式（１）においてｎが２０．麿が１、ＸがＯＨであ
るＸ−ＰＩ）Ｓ （実施例５）、一般式（１）において
ｎが２０、−が３、ＸがＯＣＨ，テあルＸ−ＰＤＳ（実
施例６）または一般式（１）においてｎが２０． ｓが
１．ＸがＮｌ２であるＸ−ＰＤＳ（実施例７）をそれぞ
れ用い、反応温度を１００℃にしたほかは実施例１と同
様にしてＸ−ＰＤＳが付着された微粒子をえ、ついでそ
の懸濁液を調製し、Ｘ−ＰＤＳの付着量および凝集速度
定数を求めた。その結果を第２表に示す。Examples 5 to 7 In general formula (1), n is 20. X-PI)S (Example 5) in which Maro is 1 and X is OH, n is 20 in general formula (1), - is 3, In general formula (1), n is 20. s is 1. Fine particles to which X-PDS was attached were obtained in the same manner as in Example 1 except that X-PDS (Example 7) in which X was Nl2 was used and the reaction temperature was 100°C, and then the suspension was The amount of attached X-PDS and the aggregation rate constant were determined. The results are shown in Table 2.
第 ２
表
第２表に示された結果より、Ｘ−ＰＤＳの官能基として
ＯＨ％０ＣＨＪおよびＮｌ２のいずれの官能基を用いた
ばあいにも、微粒子に対して１重量％以上のポリジメチ
ルシロキサンが微粒子表面上に付着され、さらには比較
例１の微粒子に比べてえられた微粒子の分散安定性が著
しく向上することがわかる。Table 2 From the results shown in Table 2, when using any of the functional groups OH%0CHJ and Nl2 as the functional group of X-PDS, polydimethylsiloxane of 1% by weight or more based on the fine particles is attached to the surface of the fine particles, and furthermore, it can be seen that the dispersion stability of the obtained fine particles is significantly improved compared to the fine particles of Comparative Example 1.
［発明の効果］
本発明のポリジメチルシロキサン被覆微粒子は、界面活
性剤または吸着性ポリマーで処理された従来の微粒子に
比べて非水溶媒中への分散安定性が飛躍的に高められた
ものである。[Effects of the Invention] The polydimethylsiloxane-coated fine particles of the present invention have dramatically improved dispersion stability in non-aqueous solvents compared to conventional fine particles treated with surfactants or adsorbent polymers. be.
この微粒子は、顔料および塗料をはじめ、長期間の分散
安定性が要求される電気泳動を利用した表示素子および
ＤＰＳ素子においてきわめて有用である。These fine particles are extremely useful in display elements and DPS elements using electrophoresis, which require long-term dispersion stability, as well as pigments and paints.
才１ 図Sai 1 diagram
第１図は、本発明のヌ施例３でえられたポリジメチルシ
ロキサン被覆微粒子の拡散反射ＦＴ−！Ｒスペクトル図
である。FIG. 1 shows the diffuse reflection FT-! of polydimethylsiloxane-coated fine particles obtained in Example 3 of the present invention. It is an R spectrum diagram.
Claims (1)
はヒドロキシル基または加水分解性基を示す）で表わさ
れるポリジメチルシロキサンと少なくともその表面がシ
リカからなる微粒子の表面に存在するヒドロキシル基と
の反応により、ポリジメチルシロキサンが Ｓｉ−Ｏ−Ｓｉ結合で該微粒子に付着されてなるポリジ
メチルシロキサン被覆微粒子。 ２ 一般式（ I ）において、Ｘがヒドロキシル基、メ
トキシ基、エトキシ基およびアミノ基よりなる群から選
ばれた少なくとも１種である請求項１記載のポリジメチ
ルシロキサン被覆微粒子。 ３ ポリジメチルシロキサンの付着量が前記微粒子に対
して１重量％以上である請求項１記載のポリジメチルシ
ロキサン被覆微粒子。 ４ 前記少なくとも表面がシリカからなる微粒子が、シ
リカ以外の微粒子の表面をシリカで被覆してなる微粒子
である請求項１記載のポリジメチルシロキサン被覆微粒
子。[Claims] 1 General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, n is an integer of 5 to 100, m is an integer of 1 to 3,
is a hydroxyl group or a hydrolyzable group), and the hydroxyl group present on the surface of the fine particles, at least the surface of which is made of silica, causes the polydimethylsiloxane to form a Si-O-Si bond. Polydimethylsiloxane coated fine particles attached to fine particles. 2. The polydimethylsiloxane-coated fine particles according to claim 1, wherein in the general formula (I), X is at least one selected from the group consisting of a hydroxyl group, a methoxy group, an ethoxy group, and an amino group. 3. The polydimethylsiloxane-coated fine particles according to claim 1, wherein the amount of polydimethylsiloxane deposited is 1% by weight or more based on the fine particles. 4. The polydimethylsiloxane-coated fine particles according to claim 1, wherein the fine particles having at least the surface made of silica are fine particles formed by coating the surface of fine particles other than silica with silica.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2056086A JPH03258866A (en) | 1990-03-07 | 1990-03-07 | Fine particle coated with polydimethylsiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2056086A JPH03258866A (en) | 1990-03-07 | 1990-03-07 | Fine particle coated with polydimethylsiloxane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03258866A true JPH03258866A (en) | 1991-11-19 |
Family
ID=13017283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2056086A Pending JPH03258866A (en) | 1990-03-07 | 1990-03-07 | Fine particle coated with polydimethylsiloxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03258866A (en) |
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