JPH0575770B2 - - Google Patents
Info
- Publication number
- JPH0575770B2 JPH0575770B2 JP2475983A JP2475983A JPH0575770B2 JP H0575770 B2 JPH0575770 B2 JP H0575770B2 JP 2475983 A JP2475983 A JP 2475983A JP 2475983 A JP2475983 A JP 2475983A JP H0575770 B2 JPH0575770 B2 JP H0575770B2
- Authority
- JP
- Japan
- Prior art keywords
- vinylcarbazole
- graphite fluoride
- polymerization
- graphite
- polymer
- 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 - Lifetime
Links
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 24
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 230000002687 intercalation Effects 0.000 description 3
- 238000009830 intercalation Methods 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 alicyclic hydrocarbons Chemical class 0.000 description 2
- 230000002528 anti-freeze Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
Description
【発明の詳細な説明】
本発明はフツ化黒鉛と高分子化合物のグラフト
複合体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a graft composite of graphite fluoride and a polymer compound.
従来、フツ化黒鉛は水との接触角が140°と大き
いことから、潤滑材料、撥水材料、凍結・防雪材
料などの多くの用途で注目されてきた。しかしな
がら、これらの用途に使用するに際しては、成型
性が悪いためこれにグリースを混合して潤滑材料
として使用したり、また種々のカーボンまたは樹
脂と混合して、離型、撥水性を向上させて使用し
ており、使用上に問題点があつた。 Since graphite fluoride has a large contact angle with water of 140°, it has attracted attention for many uses such as lubricating materials, water-repellent materials, and anti-freeze/snow materials. However, when using it for these purposes, it has poor moldability, so it is mixed with grease and used as a lubricating material, or mixed with various carbons or resins to improve mold release and water repellency. I am using it and have had some problems with it.
本発明はフツ化黒鉛の使用を簡便にし、その用
途を拡大するために、成型も容易で、フツ化黒鉛
の特性を保持する新規なフツ化黒鉛と高分子化合
物のグラフト複合体を提供するにある。 In order to simplify the use of graphite fluoride and expand its applications, the present invention provides a new graft composite of graphite fluoride and a polymer compound that is easy to mold and retains the characteristics of graphite fluoride. be.
本発明者は、前記目的を達成すべく研究の結
果、Ｎ−ビニルカルバゾールはフツ化黒鉛と溶液
中で接触させると、Ｎ−ビニルカルバゾールが重
合し、フツ化黒鉛とグラフトした複合体が生成す
ること。またＮ−ビニルカルバゾールと同時に他
のビニル単量体とを存在させると、共重合体がグ
ラフトした複合体を生成することが分かつた。こ
の知見に基いて本発明を完成したものである。 In order to achieve the above object, the present inventor conducted research and found that when N-vinylcarbazole is brought into contact with graphite fluoride in a solution, the N-vinylcarbazole polymerizes to form a composite grafted with graphite fluoride. thing. It has also been found that when N-vinylcarbazole and other vinyl monomers are present simultaneously, a composite in which the copolymer is grafted is produced. The present invention was completed based on this knowledge.
本発明において用いるフツ化黒鉛は、例えば黒
鉛をフツ素電解によつてフツ素化して得られ、そ
の化学構造は（CF2）o、及び（CF）oで表わされる
一群の化合物である。 The fluorinated graphite used in the present invention is obtained, for example, by fluorinating graphite by fluorine electrolysis, and its chemical structure is a group of compounds represented by (CF 2 ) o and (CF) o .
フツ化黒鉛とＮ−ビニルカルバゾール重合体の
グラフト複合体は溶媒中でＮ−ビニルカルバゾー
ルとフツ化黒鉛とを接触させてＮ−ビニルカルバ
ゾールを重合させることによつて製造し得られ
る。フツ化黒鉛は通常粉末として使用され、
100μｍ以下であることが望ましい。 A graft composite of graphite fluoride and N-vinylcarbazole polymer can be produced by bringing N-vinylcarbazole and graphite fluoride into contact with each other in a solvent to polymerize N-vinylcarbazole. Graphite fluoride is usually used as a powder,
It is desirable that the thickness is 100 μm or less.
その溶媒としては、Ｎ−ビニルカルバゾールが
溶解して重合を妨げないものであればよく、例え
ばトルエン、ベンゼンなどの芳香族炭化水素、ｎ
−ヘキサン、ｎ−ペンタンなどの脂肪族炭化水
素、シクロヘキサンなどの脂環型炭化水素、テト
ラヒドロフランなどのエーテル類が挙げられる。 The solvent may be any solvent as long as it dissolves N-vinylcarbazole and does not interfere with polymerization, such as aromatic hydrocarbons such as toluene and benzene, n-vinylcarbazole, etc.
Examples include aliphatic hydrocarbons such as -hexane and n-pentane, alicyclic hydrocarbons such as cyclohexane, and ethers such as tetrahydrofuran.
Ｎ−ビニルカルバゾールは単独で重合し、フツ
化黒鉛とグラフトする。重合が始まると、フツ化
黒鉛の存在下で重合しない単量体の重合を開始さ
せる能力を有する。従つて、他のビニル単量体を
主体として重合させたいときには、Ｎ−ビニルカ
ルバゾールは少量使用すればよい。その量は他の
ビニル単量体の1/10モル程度でよい。Ｎ−ビニル
カルバゾール以外の他のビニル単量体とては、Ｎ
−ビニルカルバゾールと共重合し得るものであれ
ばよい。例えば、メタクリル酸メチル、メタクリ
ル酸エチルなどのメタクリル酸アルキルエステ
ル、アクリル酸メチル、アクリル酸エチルなどの
アクリル酸アルキルエステル、アクリロニトリ
ル、メタクリロニトリル、酢酸ビニルなどが挙げ
られる。 N-vinylcarbazole is polymerized alone and grafted with fluorinated graphite. Once polymerization begins, it has the ability to initiate the polymerization of monomers that do not polymerize in the presence of fluorinated graphite. Therefore, when it is desired to polymerize mainly with other vinyl monomers, a small amount of N-vinylcarbazole may be used. The amount thereof may be about 1/10 mole of other vinyl monomers. Vinyl monomers other than N-vinylcarbazole include N-
- Any material may be used as long as it can be copolymerized with vinyl carbazole. Examples include methacrylic acid alkyl esters such as methyl methacrylate and ethyl methacrylate, acrylic acid alkyl esters such as methyl acrylate and ethyl acrylate, acrylonitrile, methacrylonitrile, and vinyl acetate.
これらのビニル単量体がＮ−ビニルカルバゾー
ルを溶解する場合には、溶媒なしに製造し得られ
る。 When these vinyl monomers dissolve N-vinylcarbazole, they can be produced without a solvent.
重合は液の温度を一旦０℃以下に下げて均一に
混合させた後、所定の反応温度例えば40〜80℃に
上げて重合させることが好ましい。この重合によ
つて、フツ化黒鉛の層間化合物の表面にグラフト
する。 In the polymerization, it is preferable to once lower the temperature of the liquid to 0° C. or below to mix uniformly, and then raise the temperature to a predetermined reaction temperature, for example, 40 to 80° C., for polymerization. Through this polymerization, grafting occurs on the surface of the intercalation compound of graphite fluoride.
反応を停止させるにはイオン重合を停止するも
のを加えることによつて行うことができる。例え
ばメタノールを加えれば停止する。 The reaction can be stopped by adding something that stops ionic polymerization. For example, adding methanol will stop it.
なお、フツ化黒鉛と重合するＮ−ビニルカルバ
ゾールのグラフト点は、Ｎ−ビニルカルバゾール
の表面に少量存在する酸素に関係していると考え
られる。この酸素を起点にしてＮ−ビニルカルバ
ゾールのビニル基同士が重合していき、フツ化黒
鉛のＮ−ビニルカルバゾールグラフト重合体が生
成されるもとの推定される。そして、本発明で得
られる重合体はモノマーであるＮ−ビニルカルバ
ゾールを溶解するメチルアルコールに不溶性とな
る程度の分子量を持つ重合体を意味する。 The grafting point of N-vinylcarbazole that polymerizes with fluorinated graphite is considered to be related to the small amount of oxygen present on the surface of N-vinylcarbazole. It is presumed that the vinyl groups of N-vinylcarbazole polymerize with each other using this oxygen as a starting point, and an N-vinylcarbazole graft polymer of graphite fluoride is produced. The polymer obtained in the present invention means a polymer having a molecular weight that is insoluble in methyl alcohol that dissolves the monomer N-vinylcarbazole.
得られるフツ化黒鉛と高分子化合物のグラフト
複合体は、トルエンなどの溶媒に良分散性を示
し、この溶液を用いることによつて均一な被覆や
シートを作ることができる。また共重合成分を適
当に選ぶことによつて熱可塑性を持ち、この性質
を利用してバルクな成型物を得ることができる。
そしてこれらはフツ化黒鉛の性質を有しており、
潤滑性、撥水性、凍結防止の各材料として使用し
得られる。また、フツ素供給剤としても利用し得
られる。例えば、Li+イオンと組み合せて電池を
作る材料として応用できる。また、これを他の高
分子材料中に混合することも容易で、これにより
型離れのよい樹脂を作ることができ、エンヂニア
リングプラスチツクとして広く利用することがで
きる優れた性質を有している。 The resulting grafted composite of graphite fluoride and a polymer compound exhibits good dispersibility in a solvent such as toluene, and by using this solution, a uniform coating or sheet can be made. In addition, by appropriately selecting copolymerization components, it has thermoplasticity, and this property can be used to obtain bulk molded products.
These have the properties of graphite fluoride,
It can be used as a lubricating, water repellent, and antifreeze material. It can also be used as a fluorine supplying agent. For example, it can be used as a material for making batteries when combined with Li + ions. Furthermore, it can be easily mixed into other polymeric materials, making it possible to create a resin with good mold release properties, which has excellent properties that can be widely used as engineering plastics.
実施例 １
平均粒子径約1μｍのフツ化黒鉛層間化合物１
ｇを100mlのナス型フラスコに入れ、真空乾燥器
で80℃で24時間乾燥した。このフツ化黒鉛をトル
エン３ml中に懸濁させた。一方トルエン３mlにＮ
−ビニルカルバゾール１ｇを溶解し、前記両液を
０℃に下げて均一液とした後、両液を混合した。
この混合液を80℃に上げ、撹拌しながら60分重合
させた。重合後メタノールを加えて重合物を沈殿
させ、沈殿物を乾燥し、ソツクスレーで未反応の
Ｎ−ビニルカルバゾールをメタノールで20時間抽
出し、重合収率を求めた。重合収率は90％であつ
た。この重合生成物をベンゼンで10時間抽出して
グラフト率を求めたところ80％であつた。この重
合体を再びトルエン中に分散させると、安定なコ
ロイド分散液が得られた。Example 1 Fluorinated graphite intercalation compound 1 with an average particle diameter of approximately 1 μm
g was placed in a 100 ml eggplant-shaped flask and dried in a vacuum dryer at 80°C for 24 hours. This fluorinated graphite was suspended in 3 ml of toluene. Meanwhile, add 3 ml of toluene to N
- 1 g of vinylcarbazole was dissolved, and both solutions were lowered to 0° C. to make a homogeneous solution, and then both solutions were mixed.
This mixture was raised to 80°C and polymerized for 60 minutes while stirring. After polymerization, methanol was added to precipitate the polymer, the precipitate was dried, and unreacted N-vinylcarbazole was extracted with methanol using Soxhlet for 20 hours to determine the polymerization yield. The polymerization yield was 90%. This polymerization product was extracted with benzene for 10 hours to determine the grafting rate, which was 80%. When this polymer was again dispersed in toluene, a stable colloidal dispersion was obtained.
実施例 ２
実施例１におけるトルエンに代え、ニトロベン
ゼン６mlを使用したところ、重合収率は90％、グ
ラフト率は75％であつた。Example 2 When 6 ml of nitrobenzene was used in place of toluene in Example 1, the polymerization yield was 90% and the grafting rate was 75%.
実施例 ３
実施例１におけるフツ化黒鉛層間化合物１ｇを
同化合物0.1ｇに、またＮ−ビニルカルバゾール
に代え、Ｎ−ビニルカルバゾール0.1ｇとメタク
リレート1.0ｇを使用した。重合収率は60％、グ
ラフト率は300％であつた。Example 3 1 g of the fluorinated graphite intercalation compound in Example 1 was replaced with 0.1 g of the same compound, and 0.1 g of N-vinylcarbazole and 1.0 g of methacrylate were used instead of N-vinylcarbazole. The polymerization yield was 60% and the grafting rate was 300%.
実施例 ４
実施例３におけるメタクリレートに代え、スチ
レン0.1ｇを使用した。重合収率は72％、グラフ
ト率は350％であつた。Example 4 Instead of methacrylate in Example 3, 0.1 g of styrene was used. The polymerization yield was 72% and the grafting rate was 350%.
なお、上記実施例でのグラフト率とは、ベンゼ
ンで10時間抽出しても、なお、残存するポリＮ−
ビニルカルバゾールを意味する。 In addition, the grafting rate in the above example refers to the amount of polyN-N-
means vinylcarbazole.
Claims (1)
Ｎ−ビニルカルバゾールと他のビニル単量体との
混合物を加熱下に混合することを特徴とするフツ
化黒鉛とＮ−ビニルカルバゾール系重合体のグラ
フト複合体の製造方法。1. Graft composite of graphite fluoride and N-vinylcarbazole polymer, which is characterized in that graphite fluoride is mixed with N-vinylcarbazole or a mixture of N-vinylcarbazole and another vinyl monomer under heating. manufacturing method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2475983A JPS59152916A (en) | 1983-02-18 | 1983-02-18 | Grafted composite of fluorinated graphite and polymeric compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2475983A JPS59152916A (en) | 1983-02-18 | 1983-02-18 | Grafted composite of fluorinated graphite and polymeric compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59152916A JPS59152916A (en) | 1984-08-31 |
| JPH0575770B2 true JPH0575770B2 (en) | 1993-10-21 |
Family
ID=12147072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2475983A Granted JPS59152916A (en) | 1983-02-18 | 1983-02-18 | Grafted composite of fluorinated graphite and polymeric compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59152916A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101831039B (en) * | 2010-05-11 | 2011-11-16 | 武汉工程大学 | Polyvinyl carbazole/graphene composite material and synthetic method and application thereof |
| CN104974316B (en) * | 2015-05-13 | 2017-11-21 | 武汉工程大学 | A kind of graphene/polymethylacrylic acid 2 (N carbazyls) ethyl ester brush composite and its preparation method and application |
-
1983
- 1983-02-18 JP JP2475983A patent/JPS59152916A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59152916A (en) | 1984-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4731408A (en) | Processable conductive polymers | |
| CN107141680B (en) | A kind of preparation method of modified graphene oxide/PMMA composite material | |
| CA1263784A (en) | Processable conductive polymers | |
| Chen et al. | Study of self‐crosslinking acrylate latex containing fluorine | |
| US5688870A (en) | Process for preparing water dispersible polymer powders | |
| Lee et al. | Synthesis of core‐shell latexes by redox initiation at ambient temperatures | |
| US3634366A (en) | Polymerizing method | |
| US3875262A (en) | Stabilized organosols through the inter-reaction of functional groups on the stabilizer and dispersed polymers | |
| JPH0575770B2 (en) | ||
| CN110358033B (en) | Monodisperse amphoteric ion exchange thermosetting resin microsphere and preparation method thereof | |
| US5112450A (en) | Processable conductive polymers | |
| US2794787A (en) | Modified gelatins obtained by polymerizing an alkenyl carbonamide in an aqueous gelatin solution | |
| JPS63284201A (en) | Preparation of organosol of fluorine-containing polymer | |
| KR101943473B1 (en) | Preparing method of polymer particle | |
| JPS61225254A (en) | Fine particle having uniform particle size and production thereof | |
| CN110437356B (en) | Super absorbent resin, preparation method and application thereof | |
| JPH0480928B2 (en) | ||
| US3796774A (en) | Graft copolymer having an alkyl vinyl ether polymer backbone | |
| JPH0527643B2 (en) | ||
| JPS59217715A (en) | Production of carbon-containing polystyrene resin | |
| KR100466450B1 (en) | Emulsifier-free emulsion polymeric composition containing hydroxy alkyl acryl phosphate metal salt | |
| JPS629243B2 (en) | ||
| JPH0337201A (en) | Production of elastic acrylic particle | |
| JPS62209106A (en) | Vinyl chloride polymer latex and production thereof | |
| CN116284551A (en) | Quick-drying high-molecular emulsion with strong wet adhesion and preparation method thereof |