TW438881B - Long-term effective anti-electrostatic agent with reactiveness and manufacturing method thereof - Google Patents

Long-term effective anti-electrostatic agent with reactiveness and manufacturing method thereof Download PDF

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TW438881B
TW438881B TW86108166A TW86108166A TW438881B TW 438881 B TW438881 B TW 438881B TW 86108166 A TW86108166 A TW 86108166A TW 86108166 A TW86108166 A TW 86108166A TW 438881 B TW438881 B TW 438881B
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Taiwan
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antistatic agent
patent application
item
scope
group
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TW86108166A
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Chinese (zh)
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Yung-Ching Shen
Ling-Yu Jeng
Ju-Shiung Li
Tzai-Wei Tzeng
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Ind Tech Res Inst
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Priority to JP10034684A priority patent/JP2974209B2/en
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Abstract

A long-term effective anti-electrostatic agent with reactiveness and manufacturing method thereof are disclosed, which include a compound containing amino groups and a compound containing epoxy groups are put into a reactor in an appropriate ratio and by slowly stirring and heating the mixture, an anti-electrostatic agent having reactive functional groups is formed at an appropriate temperature. The present invention is characterized in that the compound containing amino groups and the compound containing epoxy groups are readily reactive and the manufacturing method is quite simple. The anti-electrostatic agent of the present invention has reactive functional groups and it can react with a polymer as it is added therein. The anti-electrostatic agent that is a polymer is enduring, long-term effective, and excellent in surface property, therefore, those drawbacks in the prior art can be improved and it can be used broadly in many industries.

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438881 177[)tv^.dot:/Vicv002 A 7 ___B7_____ 五、發明説明(I ) 本發明是有關於-1種抗靜電劑及其製造方法,且特別 是有關於一種具有反應性與長效性之抗靜電劑及其製造方 法,本發明係利用含胺基(Amine, NH2)之化合物和含環氧 基(Epoxy)之化合物反應而生成此具反應性與長效性之抗 靜電劑。 習知之抗靜電劑,係屬於一種添加劑,而且多爲低分 子量之四級胺鹽類或添加導電性碳黑等來增加其抗靜電 性,如:美國專利第5,128,473號以及日本專利第平3_ 49,053號,此類產品在使用時,其低分子量之四級胺鹽易 因遷移而流失1且放置時間久時在闻分子表面易有潮濕之 現象,而影響其使用之性質。且添加過量時,易影響高分 子之物性;而摻有導電碳黑者,一方面會有脫碳之影響, 另一方面不僅限制其顏色之範圍,且與高分子亦有相容性 之問題。 經濟部中央樣隼局員工消費合作社印裝 - --1 n^li 1^1 In ^ftfe ^^^1 mu、一-^ (請先閲讀背面之注項再填寫本頁) 另一類習知之抗靜電劑爲利用有機矽化合物,作爲導 電高分子,摻混在高分子中或塗佈在高分子表面,此類高 分子不易和其他高分子相容,故以塗佈者居多,如:美國 專利第5,008,328號以及第4,584,342號專利,即爲此類 之化合物。此類產品通常爲添加型之產品,其抗靜電性之 持久性及耐擦拭水洗性較反應型之抗靜電劑差。 而美國專利第 5,356,959 、 4,931,506 、 5,262,460、 5,051,475號等,均是將添加聚氧乙院 (Polyethylene Oxide ; PE0)入闻分子中,雖然聚氧乙院 具有0H基,此0H基爲反應性官能基,但是因爲其反應性 3 本紙張尺度適用中國國家榡準(CNS ) A4規格(210X 297公釐) 438881 I 77〇twf.dot ^ic/002 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(工) 慢'反應時間長,所以需要在高溫下以促進其反應,然而 高溫卻會造成高分子的裂解。 因此,本發明的目的就是在提供一種具有反應性之長 效型抗靜電劑及其製造方法,以改善上述習知技藝之缺 點。 根據本發明的目的,提出一種具有反應性之長效型抗 靜電劑,其分子結構如第1圖所示之(I)與(π)。 化合物(I)爲具有環氧基之抗靜電劑,而化合物(II)爲 具有胺基之抗靜電劑,因爲環氧基與胺基均爲反應官能 基,化合物(I)與化合物(II)具有反應性,可反應至聚合 物上,因此本發明之抗靜電劑具有反應性與長效性。 在化合物(I)與(11)中,R2、 R4與仏爲含烷氧 (Alkylene Oxde)基鏈段(Cham),其分子量爲介於 550〜2020(g/mole)之間;而Ri、 R;與Ri爲分子量介於 44~ 20 00(g/mole)之間的的芳香烴(Aromatic Hydrocarbon) 基鏈段(Chain)或脂肪烴(Hydrocarbon)基鏈段,或含鹵 素取代基之芳香烴鏈段或脂肪烴基鏈段。該烷氧基之結構 爲-tRo_〇1iT,其中R(1爲2或3個碳原子之烴基,η爲 10〜45之數値。 根據本發明的目的,提出-種抗靜電劑之製造方法, 包括= 將含胺基之化合物與含環氧官能基之化合物,依適當 之比例放入反應器中,其中較佳之比例爲當量數比値 1/2〜2。並徐徐加溫攪拌,在溫度30~18(TC下,使含胺基 4 本紙張尺度適用中國國家標隼(CNS ) A4規格(2丨0 X 297公釐) ^n' nn ........... m - - I 1^1 1^1 一"J (讀先聞讀背面之注意事項再填寫本頁) 4 3 88 8 1 1 770twf.doc/Vic 002 A7 經濟部中央標準局貝工消費合作社印— 五、發明説明(夕) 之化合物與含環氧官能基之化合物反應而生成含反應官能 基之抗靜電劑。此外,在反.應中亦可以添加觸媒,如: 酚、醋酸、水、醇類、硝基苯、Dioxane、甲苯、二異丙 基醚(Di-i-propyl Ether)等以加速其反應。本發明之抗 靜電劑的分子結構中的環氧基以及胺基係具反應性之官能 基,而院氧基(Alkylene Oxide)鏈段則係提供抗靜電性。 其中,製造抗靜電劑所使用的含胺基之化合物的分子 結構爲H2N-Rv或者爲H2N-RS-NH2,其中R7、Rs爲含有烷氧 基之鏈段,其分子量約介於550〜2020(g/mole)之間,該烷 氧基之結構爲寸心-〇戈,其中R。爲2或3個碳原子之烴 基,η爲10〜45之數値。 而含環氧基化合物之結構爲>_R,<5,.其中R9 爲分子量介於44〜2000(g/mole)之間的芳香烴(Aromatic Hydrocarbon)鏈段(Cha i η)或脂肪烴(Hydrocarbon)基鏈 段(Cham),或者是含鹵素取代基之芳香烴基鏈段或脂肪 烴基鏈段。 本發明之特徵之一是利用胺基與環氧基之化合物的反 應性大,且抗靜電劑之製造方法非常簡單,可以使用之產 業相當廣泛,例如可應用在樹脂、塑膠加工業、特用化學 品業、塗料業以及電子資訊產品業等產業上,因此本發明 之抗靜電劑係一種高附加價値之產品。 本發明之特徵之二是本發明之抗靜電劑係屬於反應型 因此不會有習知之低分子量四級胺鹽的缺點,而且可以有 效地改善習知技藝中因爲加入導電碳黑而產生脫碳,而造 5 1 ~. - «(I ^ (請先閱讀背面之注意事項再填寫本頁) 本紙浪尺度適用中國國家橾準(CNS ) A4规格(210X29?公釐) 經濟部中央標隼局員工消費合作社印家 4388 8 1 1 770twf.doc· Vic/Ο 02 A7 B7 五、發明説明(y) 成限制其顏色之範圍以及與高分子之相容性等問題。 本發明之特徵之Η是本發明之抗靜電劑因爲具有反應 性官能基,因此具有耐久性與長效性,且表面特性佳。 爲讓本發明之上述和其他目的、特徵、和優點能更明 顯易懂,下文特舉一較佳實施例,並配合所附圖式,作詳 細說明如下: 圖式之簡單說明: 第1圖,係繪示依照本發明之一種具有反應性之長效 型抗靜電劑之分子結構圖。 第1表,係繪示依照本發明之第四實施例所製得之抗 靜電劑與不同比例之交聯劑產生反應後,產物的抗靜電性 比較。 第一實施例 爲達成本發明之(Π的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入口。將長春公司所製造的含環氧 基之化合物ΒΕ-188(重量平均分子量爲380,環氧當量爲 85〜195)約152克與Huntsman公司所製造的含胺基之化合 物M-1000(重量平均分子量爲1000,胺當量爲500)約200 克置入反應瓶中。然後在約爲30〜70 t的溫度中進行約1 小時的反應,即可獲得含環氧基之抗靜電劑。 第二實施例 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 6 (請先閲讀背面之注^^項再填寫本頁) 本紙張尺度適用中國國家標準(CNS > A4規格(210X297公釐) 438881 177〇twt\doc/Vit:/〇〇2 A7 _B7___ 五、發明説明(厂) 度計、加料口、氮氣通入口。將長春公司所製造的含環氧 基之化合物BE-188約76克與Huntsman公司所製造的含胺 基之化合物M-2070(重量平均分子量爲2000,胺當量爲 1000)約200克置入反應瓶中。然後在約爲50~8(TC的溫度 中進行約1小時的反應,即可獲得含環氧基之抗靜電劑。 第三實施例 爲達成本發明之目的,提供-實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶内具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入口。將含環氧基之化合物TBBADE (Tetra-bromo Bisphenol A Diglycidyl ether)(重量平 均分子量656,環氧當量328)約131克與Huntsman公司 所製造的含胺基之化合物M-2070約200克置入反應瓶中。 然後在約爲30〜80 SC的溫度中進行約1小時的反應,即可 獲得含環氧基之抗靜電劑D 第四實施例 經濟部中央標準局員4消費合作社印繁 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供…反應瓶,此反應瓶内具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入口。將Shell公司製造的含環氧 基之化合物Epikote 1007(重量平均分子量2900,環氧當 量1750〜2100)約193克與Huntsman公司所製造的含胺基 之化合物M-1000約25克置入反應瓶中。然後在約爲 60-150 t的溫度中進行約1小時的反應,即可獲得含環氧 基之抗靜電劑。 第五實施例 7 本紙ί長尺度適用中國國家標準{ CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 4 3 88 8 1 L 770twi'.doc. Vic/002 A7 B7 五、發明説明(& ) 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入口。將Shell公司製造的含環氧 基之化合物Epikote 1007約]93克與Huntsman公司所製 造的含胺基之化合物M-2070約50克置入反應瓶中。然後 在約爲60〜150 t的溫度中進行約1小時的反應 > 即可獲得 含環氧基之抗靜電劑。 第六實施例 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入U。將含環氧基之化合物 BDDE(Butane Diol Diglycidyl Ether)(重量平均分子量 202 ,環氧當量100)約80克與Huntsman公司所製造的含 胺基之化合物M- 1000約200克置入反應瓶中。然後在約爲 5(M00 °C的溫度中準行約1小時的反應,即可獲得含環氧 基之抗靜電劑。 第七實施例 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 度計、加料ΙΊ、氮氣通入U。將含環氧基之化合物 DGE(Diglycidyl Ether)(重量平均分子量130,環氧當 量65)約26克與Huntsman公司所製造的含胺基之化合物 M-2070約200克置入反應瓶中。然後在約爲30~70 t的溫 度中進行約30分鐘的反應,即可獲得含環氧基之抗靜電 8 t^i ^n·- n ^^^1 ml ^^^1 nn nkk I- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 4388 8 1 1 7 7 01 w f. d 〇 g V ΐ c ; 0 0 2 Α7 ---- Β7 五、發明説明()438881 177 [) tv ^ .dot: / Vicv002 A 7 ___B7_____ V. Description of the Invention (I) The present invention relates to -1 antistatic agents and a method for manufacturing the same, and in particular, to a reactive and long-lasting agent. An antistatic agent and a method for manufacturing the same, the present invention uses a compound containing an amine group (Amine, NH2) and an epoxy group (Epoxy) compound to react to form this reactive and long-acting antistatic agent. Conventional antistatic agents are an additive, and are mostly low molecular weight quaternary amine salts or the addition of conductive carbon black to increase their antistatic properties, such as: US Patent No. 5,128,473 and Japanese Patent No. 3_49,053 No. When using this kind of product, its low molecular weight quaternary amine salt is easily lost due to migration 1 and when it is left for a long time, it is easy to have moisture on the surface of the molecule, which affects its use properties. And if it is added in excess, it will easily affect the physical properties of the polymer; while the conductive carbon black will have the effect of decarburization on the one hand, on the other hand, it will not only limit the range of its color, but also have compatibility problems with the polymer. . Printed by the Consumer Cooperatives of the Central Bureau of Economic Affairs of the Ministry of Economic Affairs---1 n ^ li 1 ^ 1 In ^ ftfe ^^^ 1 mu, one-^ (Please read the note on the back before filling this page) Another type of knowledge The antistatic agent is an organic silicon compound. As a conductive polymer, it is mixed in the polymer or coated on the surface of the polymer. Such polymers are not easily compatible with other polymers, so most of them are coated, such as: US patent Patent Nos. 5,008,328 and 4,584,342 are such compounds. This type of product is usually an additive product. Its antistatic durability and resistance to wiping and washing are inferior to those of reactive antistatic agents. And US Patent Nos. 5,356,959, 4,931,506, 5,262,460, 5,051,475, etc., are added with polyoxyethylene (PE0) into the molecule, although the polyoxyethylene has a 0H group, this 0H group is a reactive functional group , But because of its reactivity 3 this paper size is applicable to China National Standard (CNS) A4 specification (210X 297 mm) 438881 I 77〇twf.dot ^ ic / 002 A7 B7 Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 2. Description of the invention (Work) Slow 'Reaction time is long, so it needs to be at high temperature to promote its reaction, but high temperature will cause the polymer to crack. Therefore, an object of the present invention is to provide a reactive long-acting antistatic agent and a method for manufacturing the same, so as to improve the shortcomings of the conventional techniques. According to the object of the present invention, a long-acting antistatic agent having reactivity is proposed, and its molecular structure is as shown in (I) and (π) in FIG. 1. Compound (I) is an antistatic agent having an epoxy group, and compound (II) is an antistatic agent having an amine group, because the epoxy group and the amine group are both reactive functional groups, the compound (I) and the compound (II) It has reactivity and can react to polymers, so the antistatic agent of the present invention has reactivity and long-acting properties. In compounds (I) and (11), R2, R4 and fluorene are Alkylene Oxde-containing segments (Cham), and their molecular weight is between 550 ~ 2020 (g / mole); and Ri, R; and Ri are aromatic hydrocarbon (Chain) or aliphatic hydrocarbon (Chain) segment with molecular weight between 44 ~ 200 (g / mole), or aromatic with halogen substituent Hydrocarbon segment or aliphatic hydrocarbyl segment. The structure of the alkoxy group is -tRo_〇1iT, where R (1 is a hydrocarbon group of 2 or 3 carbon atoms, and η is a number of 10 to 45. According to the purpose of the present invention, the manufacture of an antistatic agent is proposed. The method includes: putting the compound containing an amine group and the compound containing an epoxy functional group into a reactor in an appropriate ratio, and the preferred ratio is an equivalent number ratio of 値 1/2 ~ 2. Under the temperature of 30 ~ 18 (TC), the paper size of the paper containing amine group 4 is applicable to the Chinese National Standard (CNS) A4 specification (2 丨 0 X 297 mm) ^ n 'nn .......... m--I 1 ^ 1 1 ^ 1 一 " J (Read the notes on the back and then fill out this page) 4 3 88 8 1 1 770twf.doc / Vic 002 A7 Shellfish Consumption of the Central Standards Bureau of the Ministry of Economic Affairs Cooperative seal — 5. Description of the invention (Even) Compounds with epoxy functional groups react to form antistatic agents with reactive functional groups. In addition, catalysts can also be added in the reaction, such as: phenol, acetic acid , Water, alcohols, nitrobenzene, Dioxane, toluene, Di-i-propyl Ether, etc. to accelerate the reaction. In the molecular structure of the antistatic agent of the present invention The epoxy and amine groups are reactive functional groups, while the Alkylene Oxide segment provides antistatic properties. Among them, the molecular structure of the amine-containing compound used in the manufacture of antistatic agents is H2N -Rv or H2N-RS-NH2, where R7 and Rs are segments containing alkoxy groups, and their molecular weight is between about 550 ~ 2020 (g / mole). Where R. is a hydrocarbon group of 2 or 3 carbon atoms, η is a number from 10 to 45. And the structure of the epoxy-containing compound is > _R, < 5, where R9 is a molecular weight between 44 and 2000. (g / mole) between aromatic hydrocarbon (Cha i η) or aliphatic hydrocarbon (Hydrocarbon) segment (Cham), or halogen-containing aromatic hydrocarbon segment or aliphatic hydrocarbon segment One of the features of the present invention is that the compounds using amine groups and epoxy groups are highly reactive, and the method of manufacturing antistatic agents is very simple, and the industries that can be used are quite wide. For example, they can be used in resin, plastic processing industry, special In the chemical industry, coating industry and electronic information product industry, the present invention The antistatic agent is a product with a high added price. The second feature of the present invention is that the antistatic agent of the present invention is reactive, so it does not have the disadvantages of the conventional low molecular weight quaternary amine salt, and can effectively improve the practice. In the know-how, the decarburization occurs due to the addition of conductive carbon black, which results in 5 1 ~.-«(I ^ (Please read the precautions on the back before filling out this page) The standard of this paper is applicable to China National Standard (CNS) A4 (210X29? Mm) The Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China 4388 8 1 1 770twf.doc · Vic / Ο 02 A7 B7 V. Description of the invention (y) Limit the range of its color and its relationship with polymers Capacitive issues. A feature of the present invention is that the antistatic agent of the present invention has a reactive functional group, so it has durability and long-lasting properties, and has excellent surface characteristics. In order to make the above and other objects, features, and advantages of the present invention more comprehensible, a preferred embodiment is given below in conjunction with the accompanying drawings for detailed description as follows: Brief description of the drawings: FIG. 1 Is a diagram showing the molecular structure of a reactive long-acting antistatic agent according to the present invention. Table 1 shows the comparison of the antistatic properties of the products after the antistatic agents prepared according to the fourth embodiment of the present invention react with the crosslinkers in different proportions. The first embodiment is to achieve the invention (Π), an embodiment is provided to manufacture the antistatic agent. A reaction bottle is provided. The reaction bottle has a stirrer, a retort tube, a thermometer, a feeding port, and a nitrogen gas inlet. Approximately 152 g of epoxy-containing compound Β-188 (weight average molecular weight: 380, epoxy equivalent: 85 ~ 195) manufactured by Changchun Company and amine group-containing compound M-1000 (weight average manufactured by Huntsman) The molecular weight is 1000, and the amine equivalent is 500). About 200 grams are put into the reaction flask. Then, the reaction is performed at a temperature of about 30 to 70 t for about 1 hour to obtain an epoxy-containing antistatic agent. Second Example In order to achieve the purpose of the present invention, an example is provided to manufacture the antistatic agent. A reaction bottle is provided, which has a stirrer, a retort tube, and a temperature of 6 (please read the note ^^ on the back first) (Fill in this page) This paper size applies to Chinese national standards (CNS > A4 size (210X297 mm) 438881 177〇twt \ doc / Vit: / 〇〇2 A7 _B7___ 5. Description of the invention (factory) Nitrogen is passed through the inlet. About 76 grams of epoxy-containing compound BE-188 and about 200 grams of amine-containing compound M-2070 (weight average molecular weight 2000, amine equivalent 1000) manufactured by Huntsman were placed in a reaction flask. The reaction is performed at a temperature of 50-8 ° C for about 1 hour, and an antistatic agent containing an epoxy group can be obtained. The third embodiment provides an embodiment to manufacture the antistatic agent for the purpose of the invention. Provide a reaction flask with a stirrer, a retort tube, a thermometer, a feed port, and a nitrogen inlet. The epoxy-containing compound TBBADE (Tetra-bromo Bisphenol A Diglycidyl ether) (weight average molecular weight 656, ring Oxygen equivalent 328) about 131 grams and about 200 grams of the amine group-containing compound M-2070 manufactured by Huntsman company were placed in a reaction flask. Then, the reaction was carried out at a temperature of about 30 to 80 SC for about 1 hour, that is, Obtaining an epoxy-containing antistatic agent D. Fourth embodiment. Member of the Central Standards Bureau of the Ministry of Economic Affairs. 4. Consumer cooperatives. Infantry. In order to achieve the purpose of the invention, an example is provided to manufacture this antistatic agent. Built-in stirrer Return distillation tube, thermometer, feed port, and nitrogen inlet. About 193 grams of epoxy-containing compound Epikote 1007 (weight average molecular weight 2900, epoxy equivalent 1750 ~ 2100) manufactured by Shell company and amine containing Huntsman company About 25 grams of the basic compound M-1000 is placed in a reaction bottle. Then, the reaction is performed at a temperature of about 60-150 t for about 1 hour to obtain an antistatic agent containing an epoxy group. Fifth Embodiment 7 This paper is a long-scale application of the Chinese National Standard {CNS) A4 (210X297 mm) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 4 3 88 8 1 L 770twi'.doc. Vic / 002 A7 B7 5 &Amp; Description of the Invention In order to achieve the purpose of the present invention, an embodiment is provided to manufacture the antistatic agent. A reaction bottle is provided. The reaction bottle has a stirrer, a retorting tube, a thermometer, a feeding port, and a nitrogen gas inlet. About 93 grams of Epikote 1007, an epoxy group-containing compound manufactured by Shell Company, and about 50 grams of an amine-group-containing compound M-2070 manufactured by Huntsman, were placed in a reaction bottle. Then, the reaction is performed for about 1 hour at a temperature of about 60 to 150 t. An epoxy-containing antistatic agent can be obtained. Sixth Embodiment To achieve the purpose of the present invention, an embodiment is provided to manufacture the antistatic agent. A reaction bottle is provided. The reaction bottle has a stirrer, a retorting tube, a thermometer, a feeding port, and a nitrogen inlet. About 80 grams of epoxy-containing compound BDDE (Butane Diol Diglycidyl Ether) (weight average molecular weight 202, epoxy equivalent 100) and about 200 grams of amine group-containing compound M-1000 manufactured by Huntsman were placed in a reaction bottle . Then, the reaction can be performed for about 1 hour at a temperature of about 5 ° C (M00 ° C), and an antistatic agent containing an epoxy group can be obtained. A seventh embodiment is provided to achieve the purpose of the present invention. An embodiment is provided to manufacture this. Antistatic agent. A reaction bottle is provided. The reaction bottle has a stirrer, a retort tube, a thermometer, a feed Ί, and nitrogen gas flowing into U. The epoxy-containing compound DGE (Diglycidyl Ether) (weight average molecular weight 130, ring Oxygen equivalent 65) Approximately 26 grams and about 200 grams of the amine-containing compound M-2070 manufactured by Huntsman are placed in a reaction flask. Then, the reaction is performed at a temperature of about 30 to 70 t for about 30 minutes, Obtain antistatic containing epoxy group 8 t ^ i ^ n ·-n ^^^ 1 ml ^^^ 1 nn nkk I- (Please read the precautions on the back before filling this page) This paper size applies to Chinese national standards (CNS) A4 specifications (210X297 mm) 4388 8 1 1 7 7 01 w f. D 〇g V ΐ c; 0 0 2 Α7 ---- Β7 V. Description of the invention ()

經濟部中央樣準局員工消費合作社印製 第八實施例 爲達成本發明之目的,提供一實施例以製造此抗靜電 劑。提供一反應瓶,此反應瓶內具有攪拌器、迴餾管、溫 度計、加料口、氮氣通入口。將長春公司所製造的含環氧 基之化合物BE-188約19克與Huntsfflan公司所製造的含胺 基之化合物ED-2001(重量平均分子量2〇⑽,環氧當量5〇〇) 約200克置入反應瓶中。然後在約爲5〇〜1〇〇t:的溫度中進 行約1小時的反應,即可獲得含胺基之抗靜電劑。 第九實施例 第一表係繪示依照本發明第四實施例所得之抗靜電劑 與不「《]比例之交聯劑產生反應後,產物之抗靜電性比較。 請參照第一表’取三次第四實施例所得的含環氧基之抗靜 電劑分別加入含胺基之交聯劑,如:MEA(Mon〇ethanolPrinted by the Employees' Cooperative of the Central Sample Bureau of the Ministry of Economic Affairs. Eighth Embodiment To achieve the purpose of the invention, an embodiment is provided to manufacture the antistatic agent. A reaction bottle is provided. The reaction bottle has a stirrer, a retorting tube, a thermometer, a feeding port, and a nitrogen gas inlet. About 19 grams of epoxy-containing compound BE-188 manufactured by Changchun Company and amine group-containing compound ED-2001 (weight average molecular weight 20, epoxy equivalent 500) manufactured by Huntsfflan, about 200 grams Place into reaction flask. Then, the reaction is carried out at a temperature of about 50 to 100 t: for about 1 hour, and an antistatic agent containing an amine group can be obtained. The first table of the ninth embodiment is a comparison of the antistatic properties of the products after the reaction between the antistatic agent obtained in accordance with the fourth embodiment of the present invention and the cross-linking agent having a non- "" ratio. Please refer to the first table. The epoxy-containing antistatic agent obtained in the fourth embodiment three times was added with an amine-containing cross-linking agent, such as: MEA (Monoethanol

Amine)以及 Huntsman 公司所製造的 ED2〇〇l 與 EDR-148。 然後分別在約爲SO〜丨沁它的溫度中進行約1小時的交聯反 應’即可得到具有抗靜電的環氧樹脂,而且由第一表中產 可知本麵之抗靜糊之抗靜電性效果很 好。 - -'n^i n^— im ^^^1 — gf ^^^1 ^ (請洗閲讀背面之注意事項再填寫本頁} 本紙張尺度適用中國國家樣準 a4胁⑽乂297公董) 438881 I77〇twf.doc. Vic:G02 A7 B7 五、發明説明(2) 重量百分比_ 重量百分比 重量百分比 (%) (%) (%) 第四實施例所得 88 54 72.9 之抗靜電劑 MEA 12 0 0 ED2001 0 42.7 27.1 EDR14S 0 3.3 0 產物之表面電阻 101°.5 108.2 1〇9·5 値(Ω/Π) 第1表 . *ΜΒΜΗ \· . 0¾. 、ν'° .(請免閲讀背面之注意事項再填寫本頁) 經濟部中央標率局員工消費合作社印裝 本發明之特徵之一是利用胺基與環氧基之化合物的反 應性大,且抗靜電劑之製造方法非常簡單,可以使用之產 業相當廣泛,例如可應用在樹脂、塑膠加工業、特用化學 品業、塗料業以及電子資訊產品業等產業上,因此本發明 之抗靜電劑係一種高附加價値之產品。 本發明之特徵之二是本發明之抗靜電劑係屬於反應型 因此不會有習知之低分子量四級胺鹽的缺點,而且可以有 效地改善有習知技藝中因爲加入導電碳黑而產生脫碳,而 造成限制其顏色之範圍與高分子之相容性等問題。 本發明之特徵之三是本發明之抗靜電劑因爲具有反應 性官能基,因此具有耐久性與長效性,且表面特性佳。 雖然本發明已以一較佳實施例揭露如上,然其並非用 1 0 本紙張尺度適用中國國家標準(CNS ) A4规格< 210X297公釐) /0024388 8 1 1 770twl'.dot A7 B7 五、發明説明(1 )以限定本發明,任何熟習此技藝者,在不脫離本發明之精 神和範圍內,當可作各種之更動與潤飾,因此本發明之保 護範圍當視後附之申請專利範圍所界定者爲準。 請 咣 閱 1¾ 之 注 意 事 項 再 本 頁 經濟部中央標準局員工消費合作社印繁 本紙張尺度適用中國國家標隼(CNS ) A4規格(2!0X297公釐)Amine) and ED2000 and EDR-148 manufactured by Huntsman. Then, the cross-linking reaction is performed for about 1 hour at a temperature of about SO ~ 丨 Q. It can obtain an antistatic epoxy resin, and the antistatic properties of the antistatic paste can be found from the first table. good results. --'n ^ in ^ — im ^^^ 1 — gf ^^^ 1 ^ (Please wash and read the notes on the back before filling out this page} This paper size applies to the Chinese national standard a4 ⑽ 乂 ⑽ 乂 297 公 董) 438881 I77〇twf.doc. Vic: G02 A7 B7 V. Description of the invention (2) Weight percentage _ weight percentage weight percentage (%) (%) (%) 88 54 72.9 antistatic agent MEA 12 0 0 ED2001 0 42.7 27.1 EDR14S 0 3.3 0 The surface resistance of the product is 101 °. 5 108.2 1〇9 · 5 値 (Ω / Π) Table 1. * ΜΒΜΗ \ ·. 0¾., Ν '°. (Please avoid reading the back Note: Please fill in this page again.) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. One of the characteristics of the present invention is that the use of amine and epoxy-based compounds is highly reactive, and the method of manufacturing antistatic agents is very simple. The used industry is quite wide, for example, it can be applied to industries such as resin, plastic processing industry, special chemical industry, coating industry and electronic information product industry. Therefore, the antistatic agent of the present invention is a product with a high added price. The second feature of the present invention is that the antistatic agent of the present invention is reactive, so it does not have the disadvantages of the conventional low-molecular-weight quaternary amine salt, and can effectively improve the dehydration caused by the addition of conductive carbon black in the conventional techniques. Carbon, which causes problems such as limiting the range of its color and compatibility with polymers. The third characteristic of the present invention is that the antistatic agent of the present invention has a reactive functional group, so it has durability and long-lasting properties, and has good surface characteristics. Although the present invention has been disclosed as above with a preferred embodiment, it does not use 10 paper sizes to apply Chinese National Standard (CNS) A4 specifications < 210X297 mm) / 0024388 8 1 1 770twl'.dot A7 B7 V. Explanation of the invention (1) To limit the present invention, anyone skilled in the art can make various modifications and retouches without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention shall be regarded as the scope of patents attached The ones defined shall prevail. Please read the notes of 1¾. Reprinted on this page. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. The paper size is applicable to China National Standard (CNS) A4 (2! 0X297 mm).

Claims (1)

8 8 8 4.附8 8 8 4. Attached ABCD 申請專利範 修正日期:90年1 第80108166號專利申請案 申請專利範園修正本 種具有反應性之長效型抗靜電劑,該抗靜電劑具有反應 性官能基,該抗靜電劑之分子結構如下所示: OH OH I [>- R,-CH-CH2-N-CH2-CH-R3- nll^lll^il— I n — (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局負工消費合作社印策 其中: 爲含有燒氧基(Alkylene Oxide)之鏈段(Chain),該虎氧基 之結構爲十R〇 — O·^·,其中匕爲2或3個碳原子之經基’ n爲 10〜45之數値;以及 心、R3爲分子量介於44~2000(g/mole)之間的含烴基 (Hydrocarbon)鏈段。 2. 如申請專利範圍第1項所述之抗靜電劑,其中R2的分子量 介於550〜2020(g/mole)之間。 3. 如申請專利範圍第1項所述之抗靜電劑,其中&與&所含 烴基爲C】5~C靡之芳香烴基(Aromatic Hydrocarbon)。 4. 如申請專利範園第1項所述之抗靜電劑,其中心與民所含 烴基爲 C2~C18之脂肪烴基(Aliphatic Hydrocarbon)。 5. 如申請專利範圍第1項所述之抗靜電劑,其中氏與&所含 烴基爲含鹵素取代基之C15~C2()()之芳香烴基。 19001-86108166.doc. 訂 丨線_ 本紙張尺度適用中國國家標準(CNS ) A4规格(2丨0X2?7公釐} 4 3 88 B 1ABCD patent application amendment date: 1990 1 No. 80108166 Patent application application patent amendment Amends this kind of reactive long-acting antistatic agent, the antistatic agent has a reactive functional group, the molecule of the antistatic agent The structure is as follows: OH OH I [>-R, -CH-CH2-N-CH2-CH-R3- nll ^ lll ^ il— I n — (Please read the notes on the back before filling this page) Economy The Central Bureau of Standards, Ministry of Work, and Consumer Cooperatives printed policies among them: It is a chain containing Alkylene Oxide, and the structure of the tiger oxygen is ten R0—O · ^ ·, where the dagger is 2 or 3. The number of carbon atoms via n ′ is 10 to 45; and R3 is a hydrocarbon group with a molecular weight between 44 and 2000 (g / mole). 2. The antistatic agent according to item 1 of the scope of patent application, wherein the molecular weight of R2 is between 550 and 2020 (g / mole). 3. The antistatic agent as described in item 1 of the scope of patent application, wherein the hydrocarbon groups contained in & and & are C] 5 ~ C aromatic aromatic hydrocarbon groups (Aromatic Hydrocarbon). 4. The antistatic agent as described in item 1 of the patent application park, the center and the public contain a C2 ~ C18 aliphatic hydrocarbon group (Aliphatic Hydrocarbon). 5. The antistatic agent as described in item 1 of the scope of the patent application, wherein the hydrocarbon groups contained in H & are aromatic hydrocarbon groups of C15 ~ C2 () () containing halogen substituents. 19001-86108166.doc. Order 丨 Line_ This paper size applies to China National Standard (CNS) A4 (2 丨 0X2? 7mm) 4 3 88 B 1 申請專利範園 經濟哪中央榡準局員工消費合作枉印裂 6_如申請專利範圍第1項所述之抗靜電劑,其中匕與民所含 烴基爲含卤素取代基之c2~c]s之脂肪烴基。 7. —種具有反應性之長效型抗靜電劑,該抗靜電劑具有反應 性官能基,該抗靜電劑之分子結構如下所示: OH OH H2N—R4—NH—CH2—CH - Rj—CH—CH2—NH 一 & _ c〇>_ 其中: A、h爲含有烷氧基(Alkylene Oxide)之鏈段(Chain),該烷 氧基之結構爲十匕一〇女,其中心爲2或3個碳原子之烴基,n爲 10〜45之數値;以及 R5爲分子量介於44〜2000(g/mole)之間的含烴基(Hydrocarbon) 鏈段。 8. 如申請專利範圍第7項所述之抗靜電劑,其中心與心分子 量介於550〜2020(g/mole)之間。 9. 如申請專利範圍第7項所述之抗靜電劑,其中&所舍烴基 爲Ci5~C咖之芳香煙基(Aromatic Hydrocarbon)。 10·如申請專利範圍第7項所述之抗靜電劑,其中心所含烴基 爲匸2~〇丨8之脂肪烴基(Aliphatic Hydrocarbon)。 11. 如申請專利範圍第7項所述之抗靜電劑,其中匕所含烴基 爲含鹵素取代基之C,5~C200之芳香烴基。 12. 如申請專利範圍第7項所述之抗靜電劑,其中心所含烴基 爲含函素取代基之C2〜C18之脂肪烴基。 2 19001-861G8166.doc. -装—-----ir------^ (請先閱讀背面之注意事項再填寫本頁) ( 210χ297公釐)- 4 3 88 8 1 AS B8 C8 D8 六、申請專利範圍 13.—種具有反應性之長效型抗靜電劑之製造方珐,其包括 使當量數比値爲1/2〜2之含胺基之化合物與含環氧基之化合物在 30-200¾溫度下進行反應以生成該抗靜電劑,其中該具有反應性 之長效型抗靜電劑之分子結構爲: OH OH —Rj-CH—CH2—N—CH2—CH~R3~~ R, —-f t m· tt {請先閲讀背面之注$項再填寫本頁) 或 OH OH I 經濟部中央標準局員工消費合作社印掣 H2N-R4-NH-CH广CH—RrCH-CHrNH-R^-N!^ ; 〇0 <z 其中R2、R4、氏爲含有烷氧基(Alkylene Oxide)之鏈段 (Chain),該烷氧基之結構爲十心一0七,其中化爲2或3個竣原 子之烴基,η爲10~45之數値;以及 R、R3、&爲分子量介於44~2000(g/mole)之間的含烴基 (Hydrocarbon)鍵段。 M.如申請專利範圍第13項所述之抗靜電劑之製造方法,其 中該含胺基之化合物的結構爲: h2n-r7 其中: 尺7爲含有娱·氧基(Alkylene Oxide)之鏈段(Chain)。 19001-86108i66.doc. 訂 本紙張尺度適用中國國家標準(CMS ) A4規格(210X297公釐) 4 3S88 1 A8 B8 C8 D8 經濟部中央標準局負工消費合作社印製 申請專利範園 15·如申請專利範圍第14項所述之抗靜電劑之製造方法,其 中該燒氧基之分子量爲55〇〜2020(g/mole)之間。 16·如申請專利範圍第Μ項所述之抗靜電劑之製造方法,其 申該烷氧基之結構爲—0女,其中心爲2或3個碳原子之煙 基,η爲10〜45之數値。 17_如申請專利範園第n項所述之抗靜電劑之製造方法,其 中該含胺基之化合物的結構爲: h2n-r8-nh2 其中: 爲含烷氧基之鏈段。 18.如申請專利範圍第17項所述之抗靜電劑之製造方法,其 中該烷氧基之分子量爲550〜2020(g/mole)之間。 19·如申請專利範圍第17項所述之抗靜電劑之製造方法,其 中該烷氧基之結構爲〇士,其中&爲2或3個碳原子之煙 基,η爲10〜45之數値。 20. 如申請專利範圍第13項所述之抗靜電劑之製造方法,其 中該含環氧基之化合物的結構爲: ί>— ^—<3 其中: R9爲含烴基之鍵段。 21. 如申請專利範圍第20項所述之抗靜電劑之製造方法,其 中R9的分子量介於44〜2000(g/mole)之間。 4 19001-86108166.doc, 本紙張尺度適用中國國家標準(CNS)A4规格(210X297公釐) ---------裳------訂--------線 先聞讀背面之注意事項再填寫本頁) Α8 Β8 C8 D8 4388 8 ί 申請專利範圍 22.如_請專利範圍第20項所述 中該烴基爲Circ2〇〇之芳香煙基。&靜電劑之製造方法,其 ㈣利範圍第㈣所述之抗靜電劑之製造方法,龙 τ魏基爲<VC18之脂防烴基。 々在其 24_如申請專利範園第2〇爾述之抗靜電劑之製造方法 中該經基爲含卣素取代基之CirC2。。之芳香烴基。 、 25·如申請專利範園第20項所述之抗靜電劑之製造方法,其 中該地基爲含卣素取代基之C2〜C1S之脂肪烴基。 I--------裝—: f請先閲鲭背面之注意事項再填寫本I} η 經濟部中央標準局员工消費合作社印製 19001-86108166.doc. 本紙張尺度速用中國國家標準(CNS ) A4规格(2丨OX297公釐)Applying for a patent Fanyuan Economics, the Central Government Procurement Bureau employee consumer cooperation seal 6_ The antistatic agent described in the first scope of the patent application, in which the hydrocarbon group contained in the compound is a halogen-containing substituent c2 ~ c] s The aliphatic hydrocarbon group. 7. A long-acting antistatic agent with reactivity, the antistatic agent has a reactive functional group, and the molecular structure of the antistatic agent is as follows: OH OH H2N—R4—NH—CH2—CH-Rj— CH—CH2—NH 1 & _ c〇> _ where: A and h are Chains containing Alkylene Oxide, the structure of this alkoxy group is ten females, its center Is a hydrocarbon group of 2 or 3 carbon atoms, n is a number of 10 to 45; and R5 is a hydrocarbon group (Hydrocarbon) segment having a molecular weight between 44 and 2000 (g / mole). 8. The antistatic agent as described in item 7 of the scope of patent application, the center and cardiac molecular weight of which is between 550 ~ 2020 (g / mole). 9. The antistatic agent as described in item 7 of the scope of patent application, wherein the & hydrocarbon group is Ciro-Cro aromatic aromatic carbon (Aromatic Hydrocarbon). 10. The antistatic agent as described in item 7 of the scope of patent application, wherein the center of the antistatic agent is an aliphatic hydrocarbon group of 匸 2 ~ 〇8. 11. The antistatic agent as described in item 7 of the scope of patent application, wherein the hydrocarbon group contained in the dagger is an aromatic hydrocarbon group of C, 5 ~ C200 containing a halogen substituent. 12. The antistatic agent as described in item 7 of the scope of patent application, wherein the hydrocarbon group contained in the center is an aliphatic hydrocarbon group of C2 to C18 containing a functional group substituent. 2 19001-861G8166.doc. -Packing --------- ir ------ ^ (Please read the notes on the back before filling out this page) (210 × 297 mm)-4 3 88 8 1 AS B8 C8 D8 VI. Application scope of patent 13. A kind of reactive long-acting antistatic agent manufacturing enamel, which includes an amine group-containing compound and an epoxy group-containing compound having an equivalent ratio 値 of 1/2 to 2 The compound is reacted at a temperature of 30-200¾ to form the antistatic agent. The molecular structure of the reactive long-acting antistatic agent is: OH OH —Rj-CH—CH2—N—CH2—CH ~ R3 ~ ~ R, —-ftm · tt (Please read the note on the back before filling in this page) or OH OH I Printed by the Consumer Consumption Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs H2N-R4-NH-CH 广 CH—RrCH-CHrNH- R ^ -N! ^; 〇0 < z where R2, R4, and 氏 are chains containing an alkoxy group (Alkylene Oxide), the structure of the alkoxy group is ten hearts and one seven, which is transformed into A hydrocarbon group of 2 or 3 atoms, η is a number from 10 to 45; and R, R3, & is a hydrocarbon group (Hydrocarbon) bond with a molecular weight between 44 and 2000 (g / mole). M. The method for manufacturing an antistatic agent as described in item 13 of the scope of the patent application, wherein the structure of the amine-containing compound is: h2n-r7 where: Rule 7 is a segment containing Alkylene Oxide (Chain). 19001-86108i66.doc. The size of the paper used for this edition is applicable to the Chinese National Standard (CMS) A4 (210X297 mm) 4 3S88 1 A8 B8 C8 D8 Printed by the Central Consumers Bureau of the Ministry of Economic Affairs and Consumer Cooperatives for patent application. The method of manufacturing the antistatic agent according to item 14 of the patent scope, wherein the molecular weight of the oxyalkoxy group is between 55 and 2020 (g / mole). 16. The manufacturing method of the antistatic agent as described in item M of the scope of the patent application, the structure of the alkoxy group is -0 female, the center is an nicotyl group of 2 or 3 carbon atoms, and η is 10 ~ 45 The number of puppets. 17_ The method for manufacturing the antistatic agent according to item n of the patent application park, wherein the structure of the amine-containing compound is: h2n-r8-nh2 where: is an alkoxy-containing segment. 18. The method for manufacturing an antistatic agent according to item 17 of the scope of the patent application, wherein the molecular weight of the alkoxy group is between 550 and 2020 (g / mole). 19. The method for manufacturing an antistatic agent as described in item 17 of the scope of the patent application, wherein the structure of the alkoxy group is 0 °, where & is a nicotyl group of 2 or 3 carbon atoms, and η is 10 to 45 Count. 20. The manufacturing method of the antistatic agent according to item 13 of the scope of the patent application, wherein the structure of the epoxy group-containing compound is: ί > — ^ — < 3 where: R9 is a hydrocarbon group-containing bond segment. 21. The method for manufacturing an antistatic agent as described in item 20 of the scope of patent application, wherein the molecular weight of R9 is between 44 and 2000 (g / mole). 4 19001-86108166.doc, This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) --------- Shang -------- Order -------- line First read the notes on the back and then fill out this page) Α8 Β8 C8 D8 4388 8 ί Patent scope 22. As mentioned in the 20th item of the patent scope, the hydrocarbon group is the aromatic nicotine group of Circ2OO. & The manufacturing method of the electrostatic agent is the manufacturing method of the antistatic agent described in the second range of the scope of the invention. Longtau Weiji is a lipid antihydrocarbon group of < VC18. (2) In the method for manufacturing an antistatic agent as described in Patent Application Park No. 20, the base is CirC2 containing a halogen compound. . Aromatic hydrocarbon. 25. The method for manufacturing the antistatic agent according to item 20 of the patent application park, wherein the foundation is a C2 ~ C1S aliphatic hydrocarbon group containing a halogen compound. I -------- install—: f Please read the notes on the back of the mackerel before filling in this I} η Printed by the Staff Consumer Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs, 19001-86108166.doc. Standard (CNS) A4 specification (2 丨 OX297 mm)
TW86108166A 1997-06-13 1997-06-13 Long-term effective anti-electrostatic agent with reactiveness and manufacturing method thereof TW438881B (en)

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TW86108166A TW438881B (en) 1997-06-13 1997-06-13 Long-term effective anti-electrostatic agent with reactiveness and manufacturing method thereof
JP10034684A JP2974209B2 (en) 1997-06-13 1998-02-17 Reactive and persistent antistatic agent and method for producing the same

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US8353740B2 (en) 2005-09-09 2013-01-15 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
US7708904B2 (en) 2005-09-09 2010-05-04 Saint-Gobain Ceramics & Plastics, Inc. Conductive hydrocarbon fluid
KR101336838B1 (en) * 2012-05-15 2013-12-04 이용수 Colorless antistatic agent for electronic materials, menufactruirng method of it and ultraviolet-curable antistatic coating agent using the antistatic agent, coating material using it

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