TW200902566A - Water-soluble copolymer and aqueous dispersing agent - Google Patents

Water-soluble copolymer and aqueous dispersing agent Download PDF

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Publication number
TW200902566A
TW200902566A TW097110072A TW97110072A TW200902566A TW 200902566 A TW200902566 A TW 200902566A TW 097110072 A TW097110072 A TW 097110072A TW 97110072 A TW97110072 A TW 97110072A TW 200902566 A TW200902566 A TW 200902566A
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Taiwan
Prior art keywords
water
meth
soluble copolymer
reference example
salt
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TW097110072A
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Chinese (zh)
Inventor
Keiichi Bessho
Hiroshi Sakiyama
Tomoaki Seko
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Jsr Corp
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Publication of TW200902566A publication Critical patent/TW200902566A/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/14—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Disclosed is a water-soluble copolymer which enables to sufficiently disperse a dispersoid element having an extremely small particle size and is suitable as an aqueous dispersing agent for ultrafine particles. Also disclosed is an aqueous dispersing agent composed of such a water-soluble copolymer. Specifically disclosed is a water-soluble copolymer which is characterized by being obtained by copolymerizing a monomer composition essentially containing (a) a (meth)acrylic acid (salt), (b) an isoprene sulfonic acid (salt), and (c) at least one compound selected from N-(meth)acryloyl morpholine, N,N-diethyl(meth)acrylamide and N,N-dimethyl(meth)acrylamide.

Description

200902566 九、發明說明 【發明所屬之技術領域】 本發明係關於一種水溶性共聚合物及水性分散劑，更 詳細而言係關於一種可適於使用於作爲使微粒子分散於水 系介質用之水性分散劑的水溶性共聚合物及由此水溶性共 聚合物而成的水性分散劑。 【先前技術】 以往’以碳酸鈣、黏土、氧化鈦、氧化鋁等之無機顏 料；無機氧化物、水泥、石膏等之水硬性無機材料；煤、 焦炭、瀝青等之燃料；染料等，例如作爲使分散於水系介 質中用的分散劑，一般以水性分散劑被廣泛使用。作爲此 種水性分散劑’已知除了如聚丙烯酸及其共聚合物；乙燦 、異丁烯、戊烯、己烯、二異丁烯等之烯烴類與以順丁烯 二酐所代表之α，/3 —不飽和二羧酸酐的共聚合物；聚順 丁烯二酸等之聚羧酸系聚合物等的聚羧酸系分散劑外，還 有萘磺酸之縮合物之鹽；木質磺酸鈉、聚苯乙烯磺酸鈉等 之磺酸系分散劑。如此，水溶性高分子係利用其特性作爲 微粒子用之分散劑，而被廣泛用於工業上，近年來，進— 步期望一種可使超微粒子分散的分散劑。 然而’由以往的水溶性高分子而成的分散劑係對於超 微粒子之分散能尙不充分。 【發明內容】 -5- 200902566 本發明係鑒於以上情形而完成，其目的爲提供一種可 使粒徑極小的分散體充分地分散，適合作爲超微粒子用之 水性分散劑的水溶性共聚合物。 本發明的另一目的爲提供一種具有優異的分散性及分 散穩定性的水性分散劑。 本發明之水溶性共聚合物爲，其特徵爲將含有以（a )(甲基）丙烯酸（鹽）、與（b)異戊二烯磺酸（鹽） 、與（c )至少1種選自N —(甲基）丙烯醯嗎啉、Ν,Ν — 二乙基（甲基）丙烯醯胺、Ν，Ν —二甲基（甲基）丙烯醯 胺之化合物爲必須成分而成的單體組成物藉由共聚合而得 〇 又’本發明之水溶性共聚合物，其特徵爲將含有以（ a)(甲基）丙烯酸（鹽）、與（b，）2—丙烯醯胺一 2-甲基一 1 一丙烷磺酸（鹽）' 與（c)至少1種選自N一（ 甲基）丙烯醯嗎啉、Ν,Ν -二乙基（甲基）丙烯醯胺、 Ν，Ν -二甲基（甲基）丙烯醯胺之化合物爲必須成分而成 的單體組成物藉由共聚合而得。 本發明之水溶性共聚合物，以進而含有（d )羥乙基 (甲基）丙烯酸酯而成之單體組成物藉由共聚合而得者爲 佳。 本發明之水性分散劑，其特徵爲由上述之水溶性共聚 合物而成。 本發明之水溶性共聚合物係可使無機顏料、金屬氧化 物、有機顏料等之微粒子充分地分散於水系介質中，適於 -6- 200902566 作爲超微粒子用之水性分散劑。 [實施發明之最佳形態] 本發明之水溶性共聚合物爲將含有以以下& ( a) $ 分、（b)成分或（b，）成分及（c)成分作爲必須成分的 單體組成物藉由共聚合而求得。 (a) 成分爲由（甲基）丙烯酸及/或其鹽所成之成分 ’其具體例可例舉下述通式（1)所表示之（甲基）丙烧 酸及其鹼金屬鹽或銨鹽。 (b) 成分爲由異戊二烯磺酸（2 —甲基—i，3 一丁二 稀一1 ~磺酸）及/或其鹽所成之成分，其具體例可例舉 下述通式（2)所表示之異戊二烯磺酸及其鹼金屬鹽或銨 鹽〇 (b’）成分爲由2—丙烯醯胺一 2 —甲基一 1 一丙烷磺 酸及/或其鹽所成之成分’其具體例可例舉鹼金屬鹽或銨 鹽。 (c) 成分爲由至少1種選自下述通式（3-1)所表示 & N’M〜二甲基（甲基）丙烯醯胺、下述通式（3-2)所 表不之N，N —二乙基（甲基）丙烯醢胺、及下述通式（3- 3)所表示之N- （甲基）丙烯醯嗎啉之化合物所成之成 分。 其中’ （b)成分及（b，）成分係於可得更高分散性 一點而言，以（b )成分爲佳。 又’本發明中，於單體組成物，作爲（d )成分可使 200902566 含有下述通式（4)所表示之羥乙基（甲基）丙烯酸酯 【化1】200902566 IX. INSTRUCTIONS OF THE INVENTION [Technical Field] The present invention relates to a water-soluble copolymer and an aqueous dispersant, and more particularly to an aqueous dispersion which can be suitably used for dispersing fine particles in an aqueous medium. A water-soluble copolymer of the agent and an aqueous dispersion of the water-soluble copolymer. [Prior Art] Conventionally, inorganic pigments such as calcium carbonate, clay, titanium oxide, and aluminum oxide; hydraulic inorganic materials such as inorganic oxides, cement, and gypsum; fuels such as coal, coke, and pitch; dyes, etc., for example, A dispersant for dispersing in an aqueous medium is generally widely used as an aqueous dispersant. As such an aqueous dispersant, it is known that in addition to polyacrylic acid and its copolymer; olefins such as ethylene, isobutylene, pentene, hexene, diisobutylene and the like, and α, which is represented by maleic anhydride, - a copolymer of an unsaturated dicarboxylic anhydride; a polycarboxylic acid type dispersing agent such as a polycarboxylic acid polymer such as polymaleic acid; a salt of a condensate of naphthalenesulfonic acid; and sodium lignosulfonate; A sulfonic acid-based dispersant such as sodium polystyrene sulfonate. As described above, the water-soluble polymer is widely used in the industry as a dispersing agent for fine particles, and in recent years, a dispersing agent capable of dispersing ultrafine particles has been desired. However, the dispersant made of a conventional water-soluble polymer is insufficient for the dispersion of ultrafine particles. SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object thereof is to provide a water-soluble copolymer which is capable of sufficiently dispersing a dispersion having an extremely small particle diameter and is suitable as an aqueous dispersant for ultrafine particles. Another object of the present invention is to provide an aqueous dispersant having excellent dispersibility and dispersion stability. The water-soluble copolymer of the present invention is characterized in that it contains at least one selected from the group consisting of (a) (meth)acrylic acid (salt), (b) isoprene sulfonic acid (salt), and (c) A compound obtained from a compound of N-(meth)acryloquinone morpholine, hydrazine, hydrazine-diethyl(meth) acrylamide, hydrazine, hydrazine-dimethyl(meth) decylamine The bulk composition is obtained by copolymerization and is a water-soluble copolymer of the present invention, which is characterized by containing (a) (meth)acrylic acid (salt) and (b,) 2 - acrylamide 2-methyl-1-propanesulfonic acid (salt)' and (c) at least one selected from the group consisting of N-(methyl)propene morpholine, hydrazine, hydrazine-diethyl(meth) acrylamide, hydrazine A monomer composition in which a compound of fluorene-dimethyl(meth)acrylamide is an essential component is obtained by copolymerization. The water-soluble copolymer of the present invention is preferably obtained by copolymerization of a monomer composition further containing (d) hydroxyethyl (meth) acrylate. The aqueous dispersion of the present invention is characterized by being composed of the above water-soluble copolymer. The water-soluble copolymer of the present invention can sufficiently disperse fine particles such as an inorganic pigment, a metal oxide or an organic pigment in an aqueous medium, and is suitable as an aqueous dispersant for ultrafine particles in -6-200902566. BEST MODE FOR CARRYING OUT THE INVENTION The water-soluble copolymer of the present invention is a monomer containing an essential component as the following components: <(a)$, (b) or (b,) and (c) The composition was obtained by copolymerization. (a) The component is a component derived from (meth)acrylic acid and/or a salt thereof. Specific examples thereof include (meth)propionic acid and an alkali metal salt thereof represented by the following formula (1). Ammonium salt. (b) The component is a component composed of isoprenesulfonic acid (2-methyl-i, 3-butylene-1-sulfonic acid) and/or a salt thereof, and specific examples thereof include the following The isoprene sulfonic acid represented by the formula (2) and the alkali metal salt or ammonium salt bismuth (b') component thereof are 2-propenylamine 2-methyl-1-propane sulfonic acid and/or a salt thereof Specific examples of the component to be formed include an alkali metal salt or an ammonium salt. (c) The composition is represented by at least one selected from the group consisting of & N'M~dimethyl(meth)acrylamide, represented by the following formula (3-1), and the following formula (3-2) A component derived from a compound of N,N-diethyl(meth)acrylamide and N-(methyl)propene morpholine represented by the following formula (3-3). Among them, the components (b) and (b,) are preferably at a higher dispersibility, and the component (b) is preferred. Further, in the present invention, in the monomer composition, as the component (d), 200902566 may contain a hydroxyethyl (meth) acrylate represented by the following formula (4).

H2P=C COOA1 ⑴ [通式（1)中’R1示氫原子或甲基；A1示氫、鈉、鉀 鋰、銨。] 【化2】 π3 C —H2P = C COOA1 (1) [In the formula (1), R1 represents a hydrogen atom or a methyl group; and A1 represents hydrogen, sodium, potassium, or ammonium. ] [Chemical 2] π3 C —

Hc-Hc-

CH C Α2 2 [通式（2 )中，A2示氫原子、鈉、鉀、鋰、銨。] 【化3】 R2 h2c- CON： CH3 ,CH2CH3 (3 — 1) 【化4】 R3CH C Α 2 2 [In the formula (2), A2 represents a hydrogen atom, sodium, potassium, lithium, or ammonium. ] [Chemical 3] R2 h2c- CON: CH3 , CH2CH3 (3 - 1) [Chemical 4] R3

H2〇=C CON: 、CH2CH3 (3_2) -8- 200902566 【化5】H2〇=C CON: , CH2CH3 (3_2) -8- 200902566 【化5】

/CH2pH2、 ^CHzCH^ Ο (3-3) [通式（3-1 )至通式（3_3 )中，r2、r3及R4示氫原子或 甲基。] 【化6】 h2c=/CH2pH2, ^CHzCH^ Ο (3-3) [In the formula (3-1) to the formula (3-3), r2, r3 and R4 represent a hydrogen atom or a methyl group. ] [6] h2c=

(4) cooch^oh [通式（4)中，R5示氫原子或甲基。] 單體組成物之全單體成分中的（a)成分、（b)成分 或（b’）成分及（c)成分之含有比例係以（a)成分爲20 〜95莫耳％、（b)成分或（b，）成分爲3〜50莫耳％、 (c)成分爲1〜40莫耳％爲佳。各成分之任一者爲脫離 上述範圍，則亦有依分散體之種類，而有所得之共聚合物 分散能變低的情形，故不佳。 又，使單體組成物中含有（d )成分的情形，該（d ) 成分之含有比例係以爲全單體成分中之30莫耳％以下爲 佳、更佳爲5〜20莫耳％。 -9- 200902566 又’單體組成物中，除上述之（a)成分〜（cl)成分 以外，可使含有丨種或2種以上可於此等化合物共聚合的 其匕單體（以下，稱作「其它單體」）。 此種其匕單體之具體例，可例舉稀丙醇、甲基乙稀醇 、乙基乙稀醇、乙烯基乙醇酸等之不飽和醇類；羥丙基（ 甲基）丙稀酸酯、聚乙二醇單（甲基）丙烯酸酯、聚丙二 醇單（甲基）丙烯酸酯、甘油單（甲基）丙烯酸酯、甘油 一（甲基）丙烯酸酯、聚四甲二醇單（甲基）丙烯酸酯、 聚四甲一醇聚四甲二醇二（甲基）丙烯酸酯、丁二醇（甲 基）丙嫌酸酯、己二醇（甲基）丙烯酸酯等之含有羥基之 (甲基）丙烯酸酯類；苯乙烯' α_甲基苯乙烯、乙烯基 甲苯、對甲基苯乙烯等之芳香族乙烯基化合物；（甲基） 丙烯酸甲酯、（甲基）丙烯酸乙酯、（甲基）丙烯酸辛酯 等之（甲基）丙稀酸院基醋類；丁二稀、異戊二儲、2一 氯基—1，3 - 丁二烯、1—氯基—1,3 — 丁二烯等之脂肪族 共軛二烯；（甲基）丙烯腈等之乙烯氰基化合物等。 單體組成物之全單體成分中之其它單體的含有比例以 3 〇莫耳％以下爲佳。 本發明之水溶性共聚合物，例如可以以下地進行來製 造。 亦即，將含有（a)成分、（b)成分或（b’）成分、 (c)成分並且視需要使用的（d)成分及其它單體而成的 單體組成物於適宜的溶劑中，例如，於過氧化氫、過硫酸 鈉、過硫酸鉀等之周知的自由基聚合引發劑的存在下，反 200902566 應溫度一般在20〜200 °C、較佳爲40〜1501：，反應時間 在〇 _ 1〜2 0小時的條件下，使共聚合反應而得到本發明之 水溶性共聚合物。 其中，自由基聚合引發劑的使用量，係對於全單體成 分100重量份，一般爲〇.〇01〜20重量份、較佳爲0.01〜 1 〇重量份。 上述共聚合反應中，爲順利地進行反應，可使用適宜 的聚合反應溶劑。該聚合反應溶劑，可使用水、有機溶劑 、或可與水混合的有機溶劑和與水的混合物。 可作爲聚合反應溶劑使用的有機溶劑之具體例，可列 舉甲醇、乙醇、丙醇、丁醇等之醇類，苯、甲苯 '二甲苯 、乙苯等之芳香族烴、正戊烷、正己烷、環己烷、正庚烷 、辛烷等之脂肪族烴、二乙醚、四氫呋喃、1,4 —二嘌烷 等之醚類等。 聚合反應溶劑之使用量爲所得之水溶性共聚合物之固 形份重量的0.5〜1 0 0倍。 於上述中，藉由控制反應條件，尤其聚合反應溶劑之 量、聚合引發劑之種類及其之量、反應溫度等，可調整所 得之共聚合物的分子量。 又’於共聚合反應中，亦可將供至聚合反應的單體組 成物之全量整批地裝入反應器中來進行聚合反應，或亦可 以逐次地一邊添加單體組成物之一部份或全部而一邊進行 聚合反應。 本發明之水溶性共聚合物以其重量平均分子量爲 -11 - 200902566 2000〜20萬爲佳。此重量平均分子量爲2000以下時，無 法得到充分的分散性能，另一方面，此重量平均分子量超 過20萬時，分散穩定性降低而不佳。 本發明之水溶性共聚合物中，其磺基及羧酸基之陽離 子種係無特別限定，但爲使成爲水溶性者，係以氫、鹼金 屬、鹼土類金屬、銨、胺等爲佳。 上述鹼金屬之具體例，可列舉鈉、鉀等。 上述鹼土類金屬之具體例，可列舉鈣、鎂等。 上述胺之具體例，可列舉甲胺、乙胺、丙胺、二甲胺 、二乙胺、三乙胺、丁胺、二丁胺、三丁胺等之烷基胺； 乙烯二胺、二乙烯三胺、三乙烯四胺等之聚胺、嗎啉、哌 U定。 此等之中，以氫、鈉、鉀爲特佳。 本發明之水溶性共聚合物中，其磺基及羧酸基之陽離 子種係可藉由各種的離子交換手法來與其它種的陽離子種 互相交換。 本發明之水溶性共聚合物係以紅外線吸收光譜，於 1，300〜IdSOcnr1之磺基的吸收、於1,700〜lJOOcnT1之 羧酸基的吸收、於1,6 7 0 cm·1附近之丙烯醯胺系單體的吸 收，藉由N M R測定可確認其構造，又，磺酸量及羧酸量 之測定並以進行元素分析，可確認其構造單位之組成比。 本發明之水溶性共聚合物，藉由導入來自（a)成分 、（b)成分或（b’）成分及（c)成分之各單體的構造單 位，可得控制分散劑分子之擴散或對有機材料及無機材料 -12- 200902566 之吸附能力等的作用’於種種材料中分散性能可爲改善。 本發明之水溶性共聚合物’作爲水性分散劑，於各種 分散可適於使用體之分散。此分散體，可使用固形燃料、 水泥、染料及/或顏料、金屬氧化物等之無機材料。 此種分散體之具體例’可列舉碳黑、超導電碳黑（ Ketjen black)、石墨、木炭粉、碳纖維、鐵、銀、銅、 鉛 '鎳、碳化矽、氧化錫、氧化鐵、氧化鈦、氧化鎂、氧 化鋅、氧化铈、氧化鈣、氧化锆、氧化銻肥粒鐵（Ferrite )、氧化鋁、氫氧化鋁、氫氧化鎂、鈦酸鋇、鈦酸、锆酸 鉛、硼酸鋅、碳酸鋅、雲母、硫酸鋇、碳酸鈣、硫化鉬、 聚四氟乙烯（鐵氟龍）粉、滑石、石棉、二氧化矽珠粒、 玻璃粉、水滑石（hydrotalcite )、鐵酞菁、沸石、海泡 石、硬矽鈣石 '活化黏土、聚合物珠粒等。 混合本發明之水溶性共聚合物與上述分散體之際，作 爲溶劑，以使用水爲佳，視需要亦可添加少量的有機溶劑 。其中’有機溶劑之具體例，可列舉例如作爲單體組成物 之共聚合反應時所使用之聚合反應溶劑。 又，混合本發明之水溶性共聚合物與各種分散體的方 法’係無特別限制，可利用攪拌機、混砂機、pent conditioner、球磨機等周知的方法。 可使用的分散體之粒徑依用途而不同，無法一槪定義 ’ 一般爲0.01〜10/im的範圍。 本發明之水溶性共聚合物與分散體的比例，依應用之 用途、使用方法及分散體之粒徑等而不同，無法一槪定義 -13- 200902566 ，但水溶性共聚合物之使用量係相對於分散體以固形份換 算，一般爲0.01〜200重量％、較佳爲0.1〜100重量％ 〇 分散處理中，作爲分散劑係可單獨使用本發明之水溶 性共聚合物，亦可倂用其它的水溶性聚合物或水分散聚合 物等。其它的聚合物之具體例，可列舉聚酯系樹脂、丙烯 基樹脂、聚苯乙烯樹脂、聚氯乙烯樹脂、聚偏二氯乙烯樹 脂、聚乙烯樹脂、聚丙烯樹脂、聚胺基甲酸酯樹脂、聚醯 胺樹脂、聚乙酸乙烯樹脂、聚乙烯醇樹脂、環氧樹脂、苯 酚樹脂、纖維素系樹脂、聚有機矽氧烷樹脂、聚醯亞胺樹 脂、聚颯樹脂等之水溶性聚合物，水系乳膠樹脂。 又，作爲任意之添加劑，亦可倂用周知的難燃劑、熱 安定劑、抗氧劑、光安定化劑、脫模劑、可塑劑、著色劑 、滑劑、發泡劑等。 本發明之水溶性共聚合物，係有具有對於分散體之高 分散性能、高分散穩定性，故對於分散體漿液可賦予低黏 度化及長時間的靜置穩定性，提高各種特性之性能及經長 時間之使用亦可維持其性能的特徵。 經由組合本發明之水溶性共聚合物與分散體，可適於 種種用途。例如，有益於一般塗料、電路基板用塗料、導 電性材料、電池材料、電池電極材料、電磁波遮蔽材料、 抗靜電塗料、面狀發熱體、電化學反應電極板、電接點材 料、摩擦材料、抗菌材料、滑動材料、硏磨材料、磁氣記 錄媒體、感熱記錄材料、電色材料、光擴散薄膜、通訊電 -14- 200902566 纜用遮水材料、遮光薄膜、隔音片'塑料磁石、x線增感 屏、印刷油墨、農藥粒劑 '電子照像調色劑、合成橡膠或 合成樹脂用乳膠乳化劑、化妝品用界面活性劑等之用途。 【實施方式】 以下’對本發明列舉實施例具體地說明，但本發明不 限定於以下實施例。又’以下實施例中之％及份只要無特 別限定則爲重量基準。 又，實施例中之重量平均分子量（Mw)爲將藉由凝 膠滲透色層分析法（GPC )判定之結果，以聚苯乙烯擴酸 鈉作爲標準樣本，使用作成之檢量線來換算成者。 其中，GP C之測定條件爲如下述。 管柱 1 : G3 000PWXL[TOSOH (股）製] 管柱 2 : GMPWXL[TOSOH (股）製] 管柱 3 : GMPWXL[TOSOH (股）製] 將管柱以1〜3之順序直列地連結，由管柱1 一側導 入試料。 檢驗器：示差折射計RI_8〇21[TOSOH (股）製] 洗提液：水/乙腈/硫酸鈉=2，1 0 0 / 9 〇 〇 /1 5 (重量比） 流速：1 . 0 m 1 /分鐘 溫度：40°C 樣本濃度：〇·2% 樣本注入量：400 // 1 -15- 200902566 參考例1 1 L燒杯中加入8 0 %濃度之丙烯酸[(a )成分]水溶液 203g、40%濃度之2 —甲基一1,3— 丁二烯一1—磺酸鈉[( b )成分]水溶液1 3 7 g、及丙烯醯嗎啉[(c )成分]9 1 g後予 以混合，調製單體組成物。內容積1L之耐壓容器中，裝 入水3 00g及30%過氧化氫水l〇g，內溫成90°C時，將調 製好的單體組成物開始添加於耐壓容器內，維持內溫在 90〜l〇(TC的狀態下一邊攪拌，於1小時後結束單體組成 物之添加。添加結束後，一邊持續攪拌，在90〜100°C 4 小時的條件下，藉由進行單體組成物之共聚合處理，求得 水瑢性共聚合物。 參考例2〜8 單體組成物的調製中，除依據表1所示之摻合處方來 變更各單體之種類及量之外，其餘與參考例1相同地進行 求得水溶性共聚合物。(4) cooch^oh [In the formula (4), R5 represents a hydrogen atom or a methyl group. The content ratio of the component (a), the component (b), the component (b'), and the component (c) in the all monomer component of the monomer composition is 20 to 95 mol% of the component (a). b) The component or (b,) component is preferably 3 to 50 mol%, and the component (c) is preferably 1 to 40 mol%. When any of the components is out of the above range, the dispersion of the obtained copolymer may be lowered depending on the type of the dispersion, which is not preferable. Further, when the monomer composition contains the component (d), the content of the component (d) is preferably 30 mol% or less, more preferably 5 to 20 mol%, based on the total monomer component. -9- 200902566 Further, in the monomer composition, in addition to the above-mentioned components (a) to (cl), it is possible to contain a ruthenium monomer or two or more kinds of ruthenium monomers which can be copolymerized with these compounds (hereinafter, Called "other monomers"). Specific examples of such a fluorene monomer include unsaturated alcohols such as dilute alcohol, methyl ethyl alcohol, ethyl ethylene glycol, and vinyl glycolic acid; and hydroxypropyl (meth) acrylic acid. Ester, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, glycerol mono (meth) acrylate, glycerol mono (meth) acrylate, polytetramethylene glycol mono a hydroxy group-containing acrylate, polytetramethylene polytetramethylene glycol di(meth) acrylate, butane diol (methyl) propyl acrylate, hexane diol (meth) acrylate, etc. Methyl) acrylates; aromatic vinyl compounds such as styrene 'α-methyl styrene, vinyl toluene, p-methyl styrene; methyl (meth) acrylate, ethyl (meth) acrylate, (meth)acrylic acid-based vinegars such as octyl (meth)acrylate; dibutyl, iso-pentyl, 2-chloro-1,3-butadiene, 1-chloro--1 3 — an aliphatic conjugated diene such as butadiene; an ethylene cyano compound such as (meth)acrylonitrile; The content ratio of the other monomer in the all monomer component of the monomer composition is preferably 3 〇 mol% or less. The water-soluble copolymer of the present invention can be produced, for example, in the following manner. That is, a monomer composition containing the component (a), the component (b) or the component (b'), the component (c), and optionally the component (d), and other monomers, in a suitable solvent For example, in the presence of a known radical polymerization initiator such as hydrogen peroxide, sodium persulfate or potassium persulfate, the temperature of the counter 200902566 is generally 20 to 200 ° C, preferably 40 to 1501:, the reaction time. The water-soluble copolymer of the present invention is obtained by copolymerization under conditions of 〇 1 to 20 hours. Here, the amount of the radical polymerization initiator to be used is 100 parts by weight of the total monomer component, and is usually 0.01 to 20 parts by weight, preferably 0.01 to 1 part by weight. In the above copolymerization reaction, a suitable polymerization solvent can be used in order to carry out the reaction smoothly. As the polymerization solvent, water, an organic solvent, or an organic solvent which can be mixed with water and a mixture with water can be used. Specific examples of the organic solvent which can be used as the polymerization solvent include alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene'xylene and ethylbenzene, n-pentane and n-hexane. An aliphatic hydrocarbon such as cyclohexane, n-heptane or octane, or an ether such as diethyl ether, tetrahydrofuran or 1,4-dioxane. The polymerization solvent is used in an amount of from 0.5 to 100 times the weight of the solid content of the obtained water-soluble copolymer. In the above, the molecular weight of the obtained copolymer can be adjusted by controlling the reaction conditions, in particular, the amount of the polymerization solvent, the kind of the polymerization initiator and the amount thereof, the reaction temperature, and the like. Further, in the copolymerization reaction, the entire amount of the monomer composition supplied to the polymerization reaction may be charged into the reactor in batches to carry out the polymerization reaction, or a part of the monomer composition may be added one by one. The polymerization reaction is carried out while or all of them. The water-soluble copolymer of the present invention preferably has a weight average molecular weight of from -11 to 200902566 of from 2,000 to 200,000. When the weight average molecular weight is 2,000 or less, sufficient dispersibility cannot be obtained. On the other hand, when the weight average molecular weight exceeds 200,000, the dispersion stability is not preferable. In the water-soluble copolymer of the present invention, the sulfo group and the cation group of the carboxylic acid group are not particularly limited, but in order to be water-soluble, hydrogen, an alkali metal, an alkaline earth metal, ammonium, an amine or the like is preferred. . Specific examples of the alkali metal include sodium, potassium, and the like. Specific examples of the alkaline earth metal include calcium and magnesium. Specific examples of the above amines include alkylamines such as methylamine, ethylamine, propylamine, dimethylamine, diethylamine, triethylamine, butylamine, dibutylamine, and tributylamine; ethylenediamine and diethylene. A polyamine such as a triamine or a triethylenetetramine, a morpholine or a piperidine. Among these, hydrogen, sodium and potassium are particularly preferred. In the water-soluble copolymer of the present invention, the cation group of the sulfo group and the carboxylic acid group can be exchanged with other kinds of cationic species by various ion exchange methods. The water-soluble copolymer of the present invention has an infrared absorption spectrum, an absorption of a sulfo group at 1,300 to IdSOcnr1, an absorption of a carboxylic acid group at 1,700 to 1,000,000, and a propylene oxime in the vicinity of 1,670 cm·1. The absorption of the amine-based monomer was confirmed by NMR measurement, and the amount of the sulfonic acid and the amount of the carboxylic acid were measured for elemental analysis, and the composition ratio of the structural unit was confirmed. The water-soluble copolymer of the present invention can control the diffusion of the dispersant molecule by introducing a structural unit of each monomer from the component (a), the component (b) or the component (b') and the component (c). The effect on the adsorption capacity of organic materials and inorganic materials -12- 200902566 can be improved in various materials. The water-soluble copolymer " of the present invention" as an aqueous dispersant can be suitably dispersed in a dispersion in various forms. As the dispersion, an inorganic material such as a solid fuel, cement, a dye and/or a pigment, a metal oxide or the like can be used. Specific examples of such a dispersion include carbon black, superconducting carbon black (Ketjen black), graphite, charcoal powder, carbon fiber, iron, silver, copper, lead 'nickel, tantalum carbide, tin oxide, iron oxide, titanium oxide. , magnesium oxide, zinc oxide, cerium oxide, calcium oxide, zirconium oxide, cerium oxide ferrite (ferrite), aluminum oxide, aluminum hydroxide, magnesium hydroxide, barium titanate, titanic acid, lead zirconate, zinc borate, Zinc carbonate, mica, barium sulfate, calcium carbonate, molybdenum sulfide, polytetrafluoroethylene (Teflon) powder, talc, asbestos, cerium oxide beads, glass powder, hydrotalcite, iron phthalocyanine, zeolite, Sepiolite, hard calcareous 'activated clay, polymer beads, etc. When the water-soluble copolymer of the present invention and the above dispersion are mixed, it is preferred to use water as a solvent, and a small amount of an organic solvent may be added as needed. Specific examples of the organic solvent include, for example, a polymerization solvent used in the copolymerization reaction as a monomer composition. Further, the method of mixing the water-soluble copolymer of the present invention and various dispersions is not particularly limited, and a known method such as a stirrer, a sand mixer, a pent conditioner, or a ball mill can be used. The particle size of the dispersion which can be used varies depending on the application, and cannot be defined as a range of generally 0.01 to 10/im. The ratio of the water-soluble copolymer to the dispersion of the present invention varies depending on the application, the method of use, the particle size of the dispersion, and the like, and cannot be defined as -13 to 200902566, but the amount of the water-soluble copolymer is used. It is generally 0.01 to 200% by weight, preferably 0.1 to 100% by weight, based on the solid content of the dispersion. In the dispersion treatment, the water-soluble copolymer of the present invention can be used alone as a dispersant, and it can also be used. Other water-soluble polymers or water-dispersible polymers and the like. Specific examples of other polymers include polyester resins, acryl resins, polystyrene resins, polyvinyl chloride resins, polyvinylidene chloride resins, polyethylene resins, polypropylene resins, and polyurethanes. Water-soluble polymerization of resin, polyamide resin, polyvinyl acetate resin, polyvinyl alcohol resin, epoxy resin, phenol resin, cellulose resin, polyorganosiloxane resin, polyimide resin, polyfluorene resin, etc. Water-based latex resin. Further, as an optional additive, a well-known flame retardant, heat stabilizer, antioxidant, light stabilizer, mold release agent, plasticizer, colorant, slip agent, foaming agent, or the like can be used. The water-soluble copolymer of the present invention has high dispersibility and high dispersion stability to the dispersion, so that the dispersion slurry can be provided with low viscosity and long-term static stability, and various properties can be improved. It can also maintain its performance characteristics over a long period of time. By combining the water-soluble copolymers and dispersions of the present invention, they can be suitably used for various purposes. For example, it is useful for general coatings, coatings for circuit substrates, conductive materials, battery materials, battery electrode materials, electromagnetic wave shielding materials, antistatic coatings, planar heating elements, electrochemical reaction electrode plates, electrical contact materials, friction materials, Antibacterial materials, sliding materials, honing materials, magnetic gas recording media, thermal recording materials, electrochromic materials, light diffusing films, communication power-14- 200902566 Water-blocking materials for cables, light-shielding films, sound-insulating sheets 'plastic magnets, x-rays Intensifying screens, printing inks, pesticide granules 'electrophotographic toners, latex emulsifiers for synthetic rubber or synthetic resins, surfactants for cosmetics, and the like. [Embodiment] Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples. Further, % and parts in the following examples are based on weight unless otherwise specified. Further, the weight average molecular weight (Mw) in the examples is a result of determination by gel permeation chromatography (GPC), and sodium polystyrene is used as a standard sample, and is converted into a calibration curve by using a calibration curve. By. Among them, the measurement conditions of GP C are as follows. Column 1 : G3 000PWXL [manufactured by TOSOH Co., Ltd.] Column 2 : GMPWXL [TOSOH (manufactured by the company)] Column 3 : GMPWXL [TOSOH system] The columns are connected in series in the order of 1 to 3, The sample was introduced from the side of the column 1. Verifier: Differential refractometer RI_8〇21 [manufactured by TOSOH (stock)] Eluent: water / acetonitrile / sodium sulfate = 2,1 0 0 / 9 〇〇 / 1 5 (weight ratio) Flow rate: 1. 0 m 1 /min Temperature: 40 °C Sample concentration: 〇·2% Sample injection amount: 400 // 1 -15- 200902566 Reference example 1 1 Add 80% aqueous solution of acrylic acid [(a) component] 203g, 40 % concentration of 2 -methyl-1,3-butadiene 1-sulfonate [(b) component] aqueous solution 137 g, and propylene morpholine [(c) component] 9 1 g are mixed Modulating the monomer composition. In a pressure vessel having a volume of 1 L, 300 g of water and 30% of hydrogen peroxide water are charged, and when the internal temperature is 90 ° C, the prepared monomer composition is initially added to the pressure vessel and maintained. The internal temperature was stirred at 90 to 1 Torr (the state of TC, and the monomer composition was added after 1 hour. After the completion of the addition, stirring was continued, and the temperature was maintained at 90 to 100 ° C for 4 hours. The copolymerization of the monomer composition was carried out to obtain a water-based copolymer. Reference Examples 2 to 8 In the preparation of the monomer composition, the type and amount of each monomer were changed in addition to the blending recipe shown in Table 1. The water-soluble copolymer was obtained in the same manner as in Reference Example 1 except for the rest.

參考例A〜D 單體組成物的調製中，除依據表1所示之摻合處方來 變更各單體之種類及量之外，其餘與參考例1相同地進行 求得水溶性共聚合物。 -16- 200902566 [表i] AA80% 水溶液 IPS40% 水溶液 AMPS40% 水溶液 (c) 成分單體 HEMA ACMO DMAA DEAA 參考例1 203 137 91 參考例2 198 267 44 參考例3 245 217 24 參考例4 182 199 44 41 參考例5 184 134 89 89 參考例6 198 267 31 參考例7 198 267 40 參考例8 177 322 40 參考例A 269 224 參考例B 283 78 參考例C 590 84 參考例D 200 269 41 表1中，數字之單位爲g。 又，AA示丙烯酸、IPS示2 —甲基一 1,3- 丁二烯一 1 一磺酸鈉、ACMO示丙烯醯嗎啉、DMAA示二甲基丙烯醯 胺、DEAA示二乙基丙烯醯胺、HEMA示羥乙基丙烯酸酯 、AMPS示2-丙烯醯胺一 2—甲基一 1 一丙烷磺酸鈉。 將參考例1〜8及參考例A〜D中所得之水溶性共聚 合物之各個單體組成（莫耳％)及重量平均分子量（Mw )示於表2。 -17- 200902566 [表2] AA IPS AMPS ACMO DMAA DEAA HEMA Mw 參考例1 70 10 20 12000 參考例2 70 20 10 11000 參考例3 80 15 5 12000 參考例4 65 15 10 10 11000 參考例5 65 10 20 5 13000 參考例6 70 20 10 12000 參考例7 70 20 10 13000 參考例8 70 20 10 12000 參考例A 85 15 12000 參考例B 85 15 11000 參考例c 70 30 10000 參考例D 70 20 10 12000 實施例1〜8及比較例1〜5 將參考例1〜8及參考例A〜D中所得之水溶性共聚 合物作爲分散劑使用，於添加有該分散劑的水1 〇 〇 g中， 加入四氧化三鐵[和光純藥（股）製之試藥，一次粒徑約 lOOnm] 10g，搖動1〇分鐘，測定搖動當下之分散液中的固 形份濃度（X )。其後，將分散液加入1 〇 〇 CC的附瓶塞的 量筒，靜置24小時，以注射器輕輕地取樣分散液的上層 部，測定其固形份濃度（Y )。其後，以下述式來算出分 散穩定性之尺度（Z)。其中’Z之値爲接近1〇〇%’分 散性及分散穩定性爲良好。 式 ζ(%)=Υ/Χχΐ〇〇 結果示於表3。 -18- 200902566 [表3] 實施例/比較例 水溶性共聚合物種 水溶性共聚合物添加料 (%對氧化鐵） z(%) 實施例1 參考例1 1.0 95 實施例2 參考例2 1.0 93 實施例3 參考例3 1.0 93 實施例4 參考例4 1.0 93 實施例5 參考例5 1.0 94 實施例6 參考例6 1.0 94 實施例7 參考例7 1.0 93 實施例8 參考例8 1.0 80 比較例1 參考例A 1.0 65 比較例2 參考例B 1.0 53 比較例3 參考例C 1.0 56 比較例4 參考例D 1.0 65 比較例5 0 5 從表3之結果可清楚地瞭解以本發明之水溶性共聚合 物作爲分散劑使用之實施例1〜8中，所求得的分散液之 分散穩定性爲可具優異的分散穩定性。 相對於此，在比較例1〜5中，並無以本發明之水溶 性共聚合物作爲分散劑使用，故所求得之分散液之分散穩 定性爲低。 實施例9〜16及比較例6〜10 以參考例1〜8及參考例A〜D中所求得之水溶性共 聚合物作爲分散劑使用，於添加該分散劑之水1 〇〇g中加 入氧化鈦（金紅石型氧化鈦，一次粒徑1 8 0 nm ) 1 0 g，以 -19- 200902566 5,000rpm攪拌5分鐘後，藉由測定分散液中的氧化鈦之 平均粒徑，評估分散性。又’粒徑係以雷射粒徑解析系統 ;LPA-3000/3100[大塚電子（股）製]來測定。 結果示於表4。 [表4] 實施例/比較例 水溶性共聚合物種 水溶性共聚合物添加料 (%對氧化鐵） 粒徑(nm) 實施例9 參考例1 5.0 185 實施例10 參考例2 5.0 190 實施例11 參考例3 5.0 185 實施例12 參考例4 5.0 186 實施例13 參考例5 5.0 190 實施例14 參考例6 5.0 190 實施例15 參考例7 5.0 188 實施例16 參考例8 5.0 220 比較例6 參考例A 5.0 250 比較例7 參考例B 5.0 225 比較例8 參考例C 5.0 410 比較例9 參考例D 5.0 260 比較例10 ίΕ 0 850 從表4之結果可清楚地瞭解，以本發明之水溶性共聚 合物作爲分散劑使用之實施例9〜1 6中，分散液中之分散 體的粒徑小，對於粒徑小之分散體亦可得優異的分散性。 相對於此，在比較例6〜1 0中，並無以本發明之水溶 性共聚合物作爲分散劑使用，故分散液中之分散體的粒徑 大’對於粒徑小之分散體無獲得到充分的分散能。 -20-In the preparation of the reference examples A to D, the water-soluble copolymer was obtained in the same manner as in Reference Example 1 except that the type and amount of each monomer were changed according to the blending prescription shown in Table 1. . -16- 200902566 [Table i] AA80% Aqueous solution IPS40% Aqueous solution AMPS40% Aqueous solution (c) Component monomer HEMA ACMO DMAA DEAA Reference example 1 203 137 91 Reference example 2 198 267 44 Reference example 3 245 217 24 Reference example 4 182 199 44 41 Reference Example 5 184 134 89 89 Reference Example 6 198 267 31 Reference Example 7 198 267 40 Reference Example 8 177 322 40 Reference Example A 269 224 Reference Example B 283 78 Reference Example C 590 84 Reference Example D 200 269 41 Table 1 In the figure, the unit of the number is g. Further, AA shows acrylic acid, IPS shows 2-methyl-1,3-butadiene-sodium monosulfonate, ACMO shows propylene morpholine, DMAA shows dimethyl acrylamide, and DEAA shows diethyl propylene hydride. The amine, HEMA is hydroxyethyl acrylate, and AMPS is sodium 2-propenylamine-2-methyl-1-propane sulfonate. The monomer composition (mol%) and the weight average molecular weight (Mw) of the water-soluble copolymers obtained in Reference Examples 1 to 8 and Reference Examples A to D are shown in Table 2. -17- 200902566 [Table 2] AA IPS AMPS ACMO DMAA DEAA HEMA Mw Reference Example 1 70 10 20 12000 Reference Example 2 70 20 10 11000 Reference Example 3 80 15 5 12000 Reference Example 4 65 15 10 10 11000 Reference Example 5 65 10 20 5 13000 Reference Example 6 70 20 10 12000 Reference Example 7 70 20 10 13000 Reference Example 8 70 20 10 12000 Reference Example A 85 15 12000 Reference Example B 85 15 11000 Reference Example c 70 30 10000 Reference Example D 70 20 10 12000 Implementation Examples 1 to 8 and Comparative Examples 1 to 5 The water-soluble copolymers obtained in Reference Examples 1 to 8 and Reference Examples A to D were used as a dispersing agent, and added to water 1 〇〇g to which the dispersing agent was added. A ferroferric oxide [manufactured by Wako Pure Chemical Industries Co., Ltd., primary particle size of about 100 nm] 10 g, shaken for 1 minute, and measured the solid concentration (X) in the dispersion under shaking. Thereafter, the dispersion was placed in a measuring cylinder of a stopper of 1 〇 〇 CC, allowed to stand for 24 hours, and the upper portion of the dispersion was gently sampled with a syringe, and the solid concentration (Y) was measured. Thereafter, the scale (Z) of the dispersion stability is calculated by the following formula. Among them, the dispersion of "Z is close to 1%" and the dispersion stability is good. Formula ζ (%) = Υ / Χχΐ〇〇 The results are shown in Table 3. -18- 200902566 [Table 3] Example/Comparative Example Water-soluble copolymer type water-soluble copolymer additive (% iron oxide) z (%) Example 1 Reference Example 1 1.0 95 Example 2 Reference Example 2 1.0 93 Example 3 Reference Example 3 1.0 93 Example 4 Reference Example 4 1.0 93 Example 5 Reference Example 5 1.0 94 Example 6 Reference Example 6 1.0 94 Example 7 Reference Example 7 1.0 93 Example 8 Reference Example 8 1.0 80 Comparison Example 1 Reference Example A 1.0 65 Comparative Example 2 Reference Example B 1.0 53 Comparative Example 3 Reference Example C 1.0 56 Comparative Example 4 Reference Example D 1.0 65 Comparative Example 5 0 5 From the results of Table 3, the water-soluble solution of the present invention can be clearly understood. In Examples 1 to 8 in which the copolymer was used as a dispersant, the dispersion stability of the obtained dispersion was excellent in dispersion stability. On the other hand, in Comparative Examples 1 to 5, since the water-soluble copolymer of the present invention was not used as a dispersing agent, the dispersion stability of the obtained dispersion liquid was low. Examples 9 to 16 and Comparative Examples 6 to 10 The water-soluble copolymers obtained in Reference Examples 1 to 8 and Reference Examples A to D were used as a dispersing agent in water 1 〇〇 g to which the dispersing agent was added. Titanium oxide (rutile-type titanium oxide, primary particle diameter of 180 nm) was added to 10 g, and after stirring at -19-200902566 5,000 rpm for 5 minutes, the dispersion was evaluated by measuring the average particle diameter of titanium oxide in the dispersion. Sex. Further, the particle size was measured by a laser particle size analysis system; LPA-3000/3100 [manufactured by Otsuka Electronics Co., Ltd.]. The results are shown in Table 4. [Table 4] Example/Comparative Example Water-soluble copolymer type water-soluble copolymer additive (% iron oxide) Particle diameter (nm) Example 9 Reference Example 1 5.0 185 Example 10 Reference Example 2 5.0 190 Example 11 Reference Example 3 5.0 185 Example 12 Reference Example 4 5.0 186 Example 13 Reference Example 5 5.0 190 Example 14 Reference Example 6 5.0 190 Example 15 Reference Example 7 5.0 188 Example 16 Reference Example 8 5.0 220 Comparative Example 6 Reference Example A 5.0 250 Comparative Example 7 Reference Example B 5.0 225 Comparative Example 8 Reference Example C 5.0 410 Comparative Example 9 Reference Example D 5.0 260 Comparative Example 10 ίΕ 0 850 From the results of Table 4, it is clear that the water solubility of the present invention In Examples 9 to 16 in which the copolymer was used as a dispersing agent, the dispersion of the dispersion in the dispersion was small, and the dispersion having a small particle size was also excellent in dispersibility. On the other hand, in Comparative Examples 6 to 10, since the water-soluble copolymer of the present invention is not used as a dispersing agent, the particle size of the dispersion in the dispersion liquid is large, and the dispersion having a small particle size is not obtained. To full dispersion energy. -20-

Claims (1)

200902566 十、申請專利範圍 1 . 一種水溶性共聚合物，其特徵爲將含有以（a )( 甲基）丙烯酸（鹽）、與（b)異戊二烯磺酸（鹽）、與 (c )至少1種選自n —(甲基）丙烯醯嗎啉、N，N —二乙 基（甲基）丙烯醯胺、Ν,Ν —二甲基（甲基）丙烯醯胺之 化合物爲必須成分而成的單體組成物藉由共聚合而得。 2 · —種水溶性共聚合物，其特徵爲將含有以（a )( 甲基）丙烯酸（鹽）、與（b，）2—丙烯醯胺一 2—甲基一 1 一丙烷磺酸（鹽）、與（c)至少1種選自N-（甲基） 丙烯醯嗎啉、N，N—二乙基（甲基）丙烯醯胺、Ν,Ν —二甲 基（甲基）丙烯醯胺之化合物爲必須成分而成的單體組成 物藉由共聚合而得。 3. 如申請專利範圍第1項或第2項之水溶性共聚合 物，其爲將進而含有（d)羥乙基（甲基）丙烯酸酯而成 之單體組成物藉由共聚合而得。 4. 一種水性分散劑，其特徵爲由申請專利範圍第1 項至第3項中任一項之水溶性共聚合物而成。 -21 - 200902566 七、指定代表圖： (一） 、本案指定代表圖為：無 (二） 、本代表圖之元件代表符號簡單說明：無 八、本案若有化學式時，請揭示最能顯示發明特徵的化學 式：無200902566 X. Patent Application No. 1. A water-soluble copolymer characterized by containing (a) (meth)acrylic acid (salt), (b) isoprene sulfonic acid (salt), and (c At least one compound selected from the group consisting of n-(methyl)propene morpholine, N,N-diethyl(meth) acrylamide, hydrazine, hydrazine-dimethyl(meth) decylamine is a must The monomer composition obtained by the composition is obtained by copolymerization. 2 · a water-soluble copolymer characterized by containing (a) (meth)acrylic acid (salt), and (b,) 2 - acrylamide- 2-methyl-1-propane sulfonic acid ( Salt), and (c) at least one selected from the group consisting of N-(methyl) propylene morpholine, N,N-diethyl(meth) acrylamide, hydrazine, hydrazine-dimethyl(methyl) propylene A monomer composition in which a compound of decylamine is an essential component is obtained by copolymerization. 3. The water-soluble copolymer according to claim 1 or 2, which is obtained by copolymerization of a monomer composition further comprising (d) hydroxyethyl (meth) acrylate . An aqueous dispersant characterized by being a water-soluble copolymer of any one of claims 1 to 3. -21 - 200902566 VII. Designated representative map: (1) The representative representative of the case is: No (2), the representative symbol of the representative figure is a simple description: No. 8. If there is a chemical formula in this case, please reveal the best display invention. Chemical formula of the feature: none
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