JPS5973560A - Polymerizable sulfobetaine compound and its preparation - Google Patents
Polymerizable sulfobetaine compound and its preparationInfo
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- JPS5973560A JPS5973560A JP10269282A JP10269282A JPS5973560A JP S5973560 A JPS5973560 A JP S5973560A JP 10269282 A JP10269282 A JP 10269282A JP 10269282 A JP10269282 A JP 10269282A JP S5973560 A JPS5973560 A JP S5973560A
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract
Description
【発明の詳細な説明】
本発明は新規なる重合性スルホベタイン化合物ならびに
その製法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel polymerizable sulfobetaine compound and a method for producing the same.
分子内に第4級アンモニウム基とスルホ基を含み、ビニ
ル付加機構により重合体を形成することのできる単量体
および該単量体を重合さゼて得られる重合体が、カチオ
ンとアニオン性官能基を同一分子内に有し独得の反応性
、界面活性、電気化学的性質、生物化学的性質を示すこ
とから近年注目を集めている。A monomer containing a quaternary ammonium group and a sulfo group in its molecule and capable of forming a polymer by a vinyl addition mechanism, and a polymer obtained by polymerizing this monomer, have cationic and anionic functionalities. It has attracted attention in recent years because it has a group within the same molecule and exhibits unique reactivity, surface activity, electrochemical properties, and biochemical properties.
例えば、特公昭42−11651号には式%式%
で示されるアミンと式
八−一−−0
1
O−S−〇
1
で示されるスルトンを反応させ
(CHz ) m−I H
/
CH2=CR−
\ I
表わされる重合性中ω体を得、これをホモ重合あるいは
共重合させることにより帯電防止剤として優れたポリマ
ーを製造することが、また特開昭56−78834弓に
は
hh
Ctlz =CI−I CON+−1<Cl−12>
3 Nの(C1k ) 3SO:PH3
で示されるスルホベタインとフッ素含有モノマーを共重
合させることにより写真用帯電防止剤として優れている
ポリマーを得ることが夫々示されている。For example, in Japanese Patent Publication No. 42-11651, an amine represented by the formula % is reacted with a sultone represented by the formula 8-1-0 1 O-S-〇1 (CHz) m-I H / CH2= JP-A-56-78834 discloses that it is possible to obtain a polymerizable intermediate ω-isomer represented by CR- \ I and homopolymerize or copolymerize it to produce a polymer excellent as an antistatic agent. CI-I CON+-1<Cl-12>
It has been shown that a polymer excellent as a photographic antistatic agent can be obtained by copolymerizing a sulfobetaine represented by 3N (C1k)3SO:PH3 with a fluorine-containing monomer.
しかしながら従来、知られているこういった重合酸スル
ホベタイン化合物はいづれも重合性不飽和基と、第4級
アンモニウム基ならびにスルホ基なる両イオン性官能基
を分子内に有することのみを特徴とし、これを重合さぜ
た場合ポリマー中に組みこまれた前記官能基の特異的な
界面活性、電気化学的性質を利用しようとする意図を出
るものではなかった。しかもこういつたベタイン化合物
のyA造には、不飽和アミン化合物とスルトン類の反応
が用いられているのであるが、スルトン類に発癌性が認
められるに至り、研究は今日までのところ顕著な進展を
みていない現況にある。However, all of these conventionally known polymeric acid sulfobetaine compounds are characterized only by having a polymerizable unsaturated group and amphoteric functional groups such as a quaternary ammonium group and a sulfo group in the molecule. When this was polymerized, there was no intention to utilize the specific surface activity and electrochemical properties of the functional groups incorporated into the polymer. Moreover, the reaction of unsaturated amine compounds and sultones is used to produce yA of these betaine compounds, but sultones have been recognized to be carcinogenic, and research has made remarkable progress to date. The current situation is that we have not seen the current situation.
本発明者らは、重合性不飽和基と、第4級アンモニウム
基およびスルホ基の両イオン性官能基以外にさらにヒド
ロキシ官能基を分子内に有する下記一般式(1)で示さ
れる化合物が、該ヒドロキシル基の故に親水性に関する
ポリマーの特性例え5−
ば帯電防止効果をさらに一段と改善することができ、ま
たヒドロキシル基が反応性官能基として廟らきポリマー
の三次元架橋点となりうるため架橋性モノマーどして極
めて有用であること、ならびに該化合物が有毒物質のス
ルトン類を用いずど6エ業的有利に製造しうろことを見
出し本発明を完成するに至った。The present inventors have discovered that a compound represented by the following general formula (1) which further has a hydroxy functional group in the molecule in addition to a polymerizable unsaturated group and amphoteric functional groups such as a quaternary ammonium group and a sulfo group, Because of the hydroxyl group, the properties of the polymer related to hydrophilicity, e.g. The present inventors have completed the present invention by discovering that the compound is extremely useful and that it can be produced industrially advantageously without using sultones, which are toxic substances.
すなわち、本発明に従えば、一般式(1)(式中R1は
水素原子またはメチル基;R2は炭素数2〜4のアルキ
レン基;R3およびR4は夫々炭素数1〜4のアルキル
基:R5は炭素数3〜4のヒドロキシアルキレン基)
で示される重合性スルホベタインイト合物が提供せられ
る。That is, according to the present invention, general formula (1) (wherein R1 is a hydrogen atom or a methyl group; R2 is an alkylene group having 2 to 4 carbon atoms; R3 and R4 are each an alkyl group having 1 to 4 carbon atoms; R5 is a hydroxyalkylene group having 3 to 4 carbon atoms) A polymerizable sulfobetaineite compound is provided.
本発明にかかる化合物は文献未記載の新規化合物であっ
て、水性媒体中一般式(n)
6−
(式中R1、R2、R3およびR4は前述の通り)で示
される化合物と、一般式(III)X R5SO3M
・・・(III)(式中R5は前述の
通り、×はハロゲン原子、M+、1アルカリ金属原子)
で示される化合物とを塩基性条件下で反応させることに
より容易且つ有利に製造せられる。The compound according to the present invention is a novel compound that has not been described in any literature, and is a compound represented by the general formula (n) 6- (wherein R1, R2, R3 and R4 are as described above) in an aqueous medium, and a compound represented by the general formula (n) 6- (wherein R1, R2, R3 and R4 are as described above) III)X R5SO3M
...(III) (wherein R5 is as described above, x is a halogen atom, M+, and one alkali metal atom) can be easily and advantageously produced by reacting the compound represented by the formula under basic conditions.
本発明り法において出発原料として用いられる一般式(
IT)で示される化合物は市販されており入手可能であ
るが必要に応じ例えば米国特許第4゜287.363号
記載の方法により容易に製造せられる。代表的なアミン
化合物(II)どじでは例えばジエチルアミノエチルア
クリルアミド、ジエチルアミノエチルアクリルアミド、
ジメチルアミノヘキシルアクリルアミド、ジエチルアミ
ノエチルアクリルアミド、ジエチルアミンプロピルアク
リルアミド、ジエヂルアミノヘキシルアクリル 7−
アミド、ジプロピルアミノエヂルアクリルアミドジプロ
ビルアミノブロビルアクリルアミド、ジプロピルアミノ
ブチルアクリルアミド、ジ111ビルアミノへキシルア
クリルアミド、ジブプルアミノエチルアクリルアミド、
ジブヂルアミノプ「1ピルアクリルアミド、ジエチルア
ミノエチルアクリルアミド、ジブチルアミノヘキシルア
クリルアミドあるいはこれらの対応メタクリルアミドが
あげられる。また他方の反応原料である一般式(III
)で示されるハ【コヒドリンのスルホン酸塩も既知化合
物であって、例えばハロゲノオキシランに亜硫酸水素ナ
トリウムあるいはカリウムを反応させることにより容易
に製造され、その代表的化合物は3−へロー2−ヒト[
1キシ−プロパンスルホン酸ナトリウム、1−メチル−
2−ヒドロキシ−3−ハロープロパンスルホン酸ナトリ
ウム、2−ヒドロキシ−4−ハローブタンスルホン酸す
l〜リウム等である。The general formula (
The compound represented by IT) is commercially available and can be easily prepared, if necessary, by the method described in US Pat. No. 4,287,363. Typical amine compounds (II) include diethylaminoethyl acrylamide, diethylaminoethyl acrylamide,
Dimethylaminohexyl acrylamide, diethylaminoethyl acrylamide, diethylaminepropylacrylamide, diethylaminohexyl acryl 7-amide, dipropylaminoedyl acrylamide dipropylaminobrobyl acrylamide, dipropylaminobutylacrylamide, di-111-bylaminohexyl acrylamide, dibupur aminoethyl acrylamide,
Examples of dibutylaminopyryl acrylamide, diethylaminoethyl acrylamide, dibutylaminohexyl acrylamide, or their corresponding methacrylamides.
The sulfonic acid salt of cohydrin represented by HA [
Sodium 1-xy-propanesulfonate, 1-methyl-
These include sodium 2-hydroxy-3-halopropanesulfonate and sulfur to lithium 2-hydroxy-4-halobutanesulfonate.
反応は水性媒体中、上記両生合物を塩基f1条件下に単
に加熱するだけで容易に進行する。反応媒体としては水
が好ましく使用せられるが所望によリアセl〜ン等水と
混和可能な有機溶剤と水との混合溶媒を使用することも
できる3、上記反応は塩基性条件Fに好都合に進行せし
められ、この場合塩基どしてはアルカリ金属水酸化物、
炭酸化物あるいはアルカリ土類金属の水酸化物、炭酸化
物等が右利に使用せられる。又反応原料のアミン化合物
(If)とハロゲン化物(I[[)の使用割合はほぼ等
モルであるが、後者をやや過剰に、例えば0.1〜0.
4モル過剰に用いることが反応をより確実迅速ならしめ
る十で好ましい。反応は通常常圧下に60〜100℃、
好ましくは80〜100℃で実施せられるが、所望によ
り大気圧以上あるいは以下でより高音あるいは低温を用
いることも可能である。なお反応を水可溶性のラジカル
重合禁1F剤例えばバラニトロソフェノールの少量例え
ば300〜3000 ppmの存在下に実施ずれば早期
重合を防止することができより有利である。このように
して反応は容易に進行し通常時間程度で終了づるが、反
応終了後、反応混合物を酸で中和し、−〇−
減圧で溶媒を除去したあと、適当な極性溶媒例えばメタ
ノール、エタノール、メチルセロソルブ等で抽出し、溶
媒除去の通常手段で目的とする一般式(I>で示される
化合物を分取することができる。かくして得られる本発
明の一般式(I)で示される化合物は一般に水に可溶で
あり、極性溶媒例えばメタノール、エタノール、メチル
セ[1ソルブ、]ニチレングリコール、DMSOに溶【
フる。これら化合物は内部塩構造をもつため、塩基物質
や酸性物質が共存せずども水や有機溶媒に溶ける特性を
有する。The reaction proceeds easily by simply heating both of the above biocompounds under base f1 conditions in an aqueous medium. Water is preferably used as the reaction medium, but if desired, a mixed solvent of water and a water-miscible organic solvent such as lyacerone can also be used.3 The above reaction is conveniently carried out under basic conditions F. In this case, the base is an alkali metal hydroxide,
Carbonates or alkaline earth metal hydroxides, carbonates, etc. are used appropriately. Further, the amine compound (If) and the halide (I[[), which are reaction raw materials, are used in approximately equimolar proportions, but the latter is used in a slight excess, for example, 0.1 to 0.
It is preferable to use a 4 molar excess because it ensures a rapid reaction. The reaction is usually carried out at 60-100°C under normal pressure.
It is preferably carried out at a temperature of 80 to 100°C, but it is also possible to use higher temperatures or lower temperatures above or below atmospheric pressure, if desired. It is more advantageous to carry out the reaction in the presence of a small amount, for example 300 to 3000 ppm, of a water-soluble radical polymerization inhibitor 1F agent, such as varanitrosophenol, in order to prevent premature polymerization. In this way, the reaction proceeds easily and is completed in about the usual time. After the reaction is completed, the reaction mixture is neutralized with an acid, the solvent is removed under reduced pressure, and then a suitable polar solvent such as methanol or ethanol is added. , methyl cellosolve, etc., and the desired compound represented by the general formula (I>) can be fractionated by ordinary means of solvent removal.The compound represented by the general formula (I) of the present invention thus obtained is It is generally soluble in water, and soluble in polar solvents such as methanol, ethanol, methyl ester, nittylene glycol, and DMSO.
Full. Since these compounds have an internal salt structure, they have the property of being soluble in water and organic solvents without the coexistence of basic substances and acidic substances.
また重合性不飽和基の故に前記内部塩の構造特性を高分
子化合物に組みこみ発現でき、例えば電気的特性どして
帯電防止性を与え、界面活1イ1効宋として高分子化合
物に乳化、分散、浸透性をイ;1与することができ各種
高分子化合物の製)盾部r1どして有用である。In addition, because of the polymerizable unsaturated group, the structural characteristics of the internal salt can be incorporated into a polymer compound, such as providing antistatic properties with electrical properties, and emulsifying into a polymer compound as a surface active agent. , dispersion, and permeability, and are useful as shield parts made of various polymer compounds.
以下実施例により本発明を説明する。例文中1.′tに
ことわりなき限り「部」とあるは「重量部」を意味する
。The present invention will be explained below with reference to Examples. Example sentence 1. Unless otherwise specified, "parts" means "parts by weight."
10−
実施例1
反応容器にジメチルアミノプロピルメタクリルアミド1
70部と3−クロル−2−ヒドロキシ−プロパンスルホ
ン酸ソーダ236部、脱イオン水274部、水酸化ナト
リウム5部、p−二1−ロソフェノール1部を混合し8
0℃で5時間攪拌し反応を終了する。反応液を冷却し過
剰の水酸化ナトリウムを塩酸で中和する。反応液中の水
分を減圧下で除去する。さらにメタノール500部を加
え、溶解させると白色結晶を含むサスペンションとなる
。これを口過により白色結晶を除き、得られたn液より
減圧下でメタノールを除ぎアはトン400部で洗浄後、
減圧乾燥により黄白色固体281部を冑だ。本生成物は
NMR,IR分析の結果下記構造式の化合物であること
が確認された。10- Example 1 Dimethylaminopropyl methacrylamide 1 in a reaction vessel
70 parts of sodium 3-chloro-2-hydroxy-propanesulfonate, 236 parts of deionized water, 5 parts of sodium hydroxide, and 1 part of p-21-rosophenol were mixed to produce 8 parts.
The reaction was completed by stirring at 0°C for 5 hours. The reaction solution is cooled and excess sodium hydroxide is neutralized with hydrochloric acid. Water in the reaction solution is removed under reduced pressure. Further, 500 parts of methanol is added and dissolved to form a suspension containing white crystals. The white crystals were removed by passing through the mouth, methanol was removed from the resulting N solution under reduced pressure, and A was washed with 400 parts of ton.
281 parts of a yellowish white solid was removed by drying under reduced pressure. As a result of NMR and IR analysis, this product was confirmed to be a compound having the following structural formula.
第1図にこの化合物のNMRチャートを示す。FIG. 1 shows an NMR chart of this compound.
尚測定はD20溶媒中で実施したく以下すべて同じ)。It should be noted that the measurement is to be carried out in D20 solvent (the same applies hereafter).
[R分析結果
1660cm’ 、1550cm’に一〇 〇 N L
l−による吸収、
1040cvlにSOpによる吸収が認められた。[R analysis result 10 〇 N L at 1660 cm' and 1550 cm'
Absorption by l- and absorption by SOp at 1040cvl were observed.
実施例2
実施例1でジメチルアミノプロピルメタクリルアミドの
かわりにジエチルアミノプロピルメタクリルアミド19
8部を用いる以外は同様の配合と操作により固体305
部を得た。Example 2 Diethylaminopropyl methacrylamide 19 was used instead of dimethylaminopropyl methacrylamide in Example 1.
Solid 305 was obtained by the same formulation and operation except that 8 parts were used.
I got the department.
本化合物は下記構造式を右することがNMR1IR分析
により確認された。It was confirmed by NMR1IR analysis that this compound has the following structural formula.
NMR分析
CHz Cl−13
−
IR分析
1660cm’ 、1550ctvlに一〇ON+−1
−11040cm’に−SOPによる吸収が認められた
。NMR analysis CHz Cl-13 - IR analysis 1660cm', 10ON+-1 at 1550ctvl
Absorption due to -SOP was observed at -11040 cm'.
実施例3
実施例でジメチルアミノプロピルメタクリルアミドのか
わりにジブチルアミノエチルメタクリルアミド212部
を用いる以外は同様の配合と操作により黄白色固体31
9部を得た。Example 3 Yellow-white solid 31
Got 9 copies.
このものの構造は であることが確認された。The structure of this thing is It was confirmed that
13−
NMR分析
Cl−120山C比C山
[R分析
1660ct’ 、1550cm−1に一〇 〇 N
+−1−の、また1040cm−1にSOpの吸収が認
められた。13- NMR analysis Cl-120 mountain C ratio C mountain [R analysis 1660 ct', 100 N at 1550 cm-1
Absorption of SOp was observed at +-1- and at 1040 cm-1.
実施例4
実施例1でジメチルアミノプロピルメタクリルアミドの
かわりにジメチルアミツブデルアクリルアミド170部
を用いる以外は同様の配合ど操作により黄白色固体28
8部を得た。Example 4 A yellowish white solid of 28% was obtained by the same blending procedure as in Example 1 except that 170 parts of dimethylaminopropylmethacrylamide was used instead of dimethylaminopropylmethacrylamide.
I got 8 copies.
このものの構造は CH+ であることが確認された。The structure of this thing is CH+ It was confirmed that
NMR分析 −L/I− δ=5.7〜6.4ppm (C112=CH)。NMR analysis -L/I- δ=5.7-6.4ppm (C112=CH).
1.8〜2.5 (CI’12C1(2C±CH2)C
H3
−
3,2(−N−)
CH3
IR分析
1660cn+−’ 、1540cm−’に−CONH
−の、また1040CIl+′1に−SOPの吸収が認
められた。1.8~2.5 (CI'12C1(2C±CH2)C
H3-3,2(-N-) CH3 IR analysis 1660cn+-', 1540cm-' -CONH
Absorption of -SOP was observed in - and also in 1040CIl+'1.
実施例5
反応容器にジエヂルアミノエヂルアクリルアミド170
部と4−クロル−2−ヒドロキシブタンスルホン酸25
3部、脱イオン水290部、水酸化ナトリウム5部、p
−二トロソフェノール1.2部を仕込み80℃で8時間
攪拌し反応を終了する。Example 5 Dietylaminoedyl acrylamide 170 in the reaction vessel
part and 4-chloro-2-hydroxybutanesulfonic acid 25
3 parts, 290 parts deionized water, 5 parts sodium hydroxide, p
- Add 1.2 parts of nitrosophenol and stir at 80°C for 8 hours to complete the reaction.
冷却後、過剰の水酸化ナトリウムを塩酸で中和する。反
応液より減圧下で水を除去しエタノール600部で溶解
し、得られたサスペンションより口過により固形分を除
去し、残りの0液より減圧下でエタノールを除去した後
アセトン400部で洗浄し減圧乾燥し、黄白色固体29
0部を1qだ1゜このものの構造は
C11z C1−13
であることが確認された。After cooling, excess sodium hydroxide is neutralized with hydrochloric acid. Water was removed from the reaction solution under reduced pressure, dissolved in 600 parts of ethanol, solids were removed from the resulting suspension by filtration, and ethanol was removed from the remaining solution under reduced pressure, followed by washing with 400 parts of acetone. Dry under reduced pressure, yellowish white solid 29
The structure of this product was confirmed to be C11z C1-13.
NMR分析
δ=5.7〜6.411r)III (CI−12=
Cl−1) 。NMR analysis δ=5.7-6.411r)III (CI-12=
Cl-1).
Cl42 CH3
1部分析
1660cm−’ 、1450cn+−”に−〇 〇
N H−の、また1040CIIl′(に−SOPの吸
収が認められた。Cl42 CH3 1 part analysis 1660cm-', 1450cn+-'' -〇 〇
Absorption of NH- and 1040CIIl' (-SOP) was observed.
【図面の簡単な説明】
第1図は本発明にかかる化合物(一般式■、R1=CH
3,R2= Ctlz CD□C1−1□−、R3、R
4=Cl−13。
17−[Brief Description of the Drawings] Figure 1 shows the compound according to the present invention (general formula ①, R1=CH
3, R2= Ctlz CD□C1-1□-, R3, R
4=Cl-13. 17-
Claims (1)
2〜4のアルキレン基;R3およびR4は夫々炭素数1
〜4のアルキル基;R6は炭素数3〜4のヒドロキシア
ルキレン基) で示される重合性スルホベタイン化合物。 (2)R5が−CH2CH(OH) CH2−である
特許請求の範囲第1項記載の化合物。 許請求の範囲第1項記載の化合物。 (4)一般式 (式中、R1は水素原子またはメチル基;Rzは炭素数
2〜4のアルキレン基;R3およびR4は夫々炭素数1
〜4のアルキル基) で示される化合物と、一般式 %式%(1) ′ (式中、R5は炭素数3〜4のとドロ:1ジアルキ
レン基、Xはハロゲン原子:Mはアルカリ金属原子) で示されるアルキレンハロヒドリンスルホンl Jiを
、水性媒体中塩基性条件下で反応させることを特徴とす
る、一般式 (式中R+ 、R2、R3、R4、R6は前述の通り) で示される重合性スルホベタイン化合物の製造方法。 (5)反応をアルカリ金属水酸化物、および/またはア
ルカリ土類金属水酸化物の塩基触媒の存在下に実施する
特許請求の範囲第3項記載の方法。 (6)反応を重合禁止剤の存在下に実施する特許請求の
範囲第3項記載の方法。[Scope of Claims] (1) General formula (wherein R1 is a hydrogen atom or a methyl group; R2 is an alkylene group having 2 to 4 carbon atoms; R3 and R4 are each a carbon number 1
~4 alkyl group; R6 is a hydroxyalkylene group having 3 to 4 carbon atoms) A polymerizable sulfobetaine compound represented by the following. (2) The compound according to claim 1, wherein R5 is -CH2CH(OH)CH2-. A compound according to claim 1. (4) General formula (in the formula, R1 is a hydrogen atom or a methyl group; Rz is an alkylene group having 2 to 4 carbon atoms; R3 and R4 are each a carbon number 1
~4 alkyl group) and a compound represented by the general formula % formula % (1)' (wherein, R5 is a carbon number 3 to 4 dialkylene group, X is a halogen atom, and M is an alkali metal Atom) with the general formula (wherein R+, R2, R3, R4, R6 are as described above), characterized by reacting an alkylene halohydrin sulfone lJi represented by A method for producing a polymerizable sulfobetaine compound as shown. (5) The method according to claim 3, wherein the reaction is carried out in the presence of a base catalyst of an alkali metal hydroxide and/or an alkaline earth metal hydroxide. (6) The method according to claim 3, wherein the reaction is carried out in the presence of a polymerization inhibitor.
Priority Applications (1)
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JP10269282A JPS5973560A (en) | 1982-06-15 | 1982-06-15 | Polymerizable sulfobetaine compound and its preparation |
Applications Claiming Priority (1)
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---|---|---|---|
JP10269282A JPS5973560A (en) | 1982-06-15 | 1982-06-15 | Polymerizable sulfobetaine compound and its preparation |
Publications (1)
Publication Number | Publication Date |
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JPS5973560A true JPS5973560A (en) | 1984-04-25 |
Family
ID=14334298
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JP10269282A Pending JPS5973560A (en) | 1982-06-15 | 1982-06-15 | Polymerizable sulfobetaine compound and its preparation |
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JP (1) | JPS5973560A (en) |
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FR2851572A1 (en) * | 2003-02-20 | 2004-08-27 | Rhodia Chimie Sa | Compositions for cleaning or rinsing hard surfaces, e.g. floors, toilet bowls or glass, containing polybetaine compounds to impart lasting soil deposition and/or adhesion inhibiting properties |
FR2851573A1 (en) * | 2003-02-20 | 2004-08-27 | Rhodia Chimie Sa | Compositions for cleaning or rinsing hard surfaces, e.g. floors, toilet bowls or glass, containing polybetaine compounds to impart lasting soil deposition and/or adhesion inhibiting properties |
JP2015504441A (en) * | 2011-11-29 | 2015-02-12 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing salt of acrylamido-2-methylpropanesulfonic acid (A), acrylamido-2-methylpropanesulfonic acid (A) or a salt thereof, and method for producing a copolymer using the same |
CN105439909A (en) * | 2015-11-19 | 2016-03-30 | 中国石油天然气股份有限公司 | Sulfonate betaine and sulfonate betaine type hydrophobic polymer, and preparation method and application thereof |
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WO2016132993A1 (en) * | 2015-02-17 | 2016-08-25 | 富士フイルム株式会社 | Composition for polymerization, method for producing same, coating composition containing same, method for producing coating composition containing said compositions, and method for producing coating |
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1982
- 1982-06-15 JP JP10269282A patent/JPS5973560A/en active Pending
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FR2851572A1 (en) * | 2003-02-20 | 2004-08-27 | Rhodia Chimie Sa | Compositions for cleaning or rinsing hard surfaces, e.g. floors, toilet bowls or glass, containing polybetaine compounds to impart lasting soil deposition and/or adhesion inhibiting properties |
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JP2010100861A (en) * | 2003-02-20 | 2010-05-06 | Rhodia Chim | Composition for cleaning or rinsing hard surface |
US7923428B2 (en) | 2003-02-20 | 2011-04-12 | Rhodia Chimie | Composition for cleaning or rinsing hard surfaces |
JP2015504441A (en) * | 2011-11-29 | 2015-02-12 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing salt of acrylamido-2-methylpropanesulfonic acid (A), acrylamido-2-methylpropanesulfonic acid (A) or a salt thereof, and method for producing a copolymer using the same |
WO2016132993A1 (en) * | 2015-02-17 | 2016-08-25 | 富士フイルム株式会社 | Composition for polymerization, method for producing same, coating composition containing same, method for producing coating composition containing said compositions, and method for producing coating |
JPWO2016132993A1 (en) * | 2015-02-17 | 2017-08-31 | 富士フイルム株式会社 | Polymerization composition and method for producing the same, coating composition containing the same, method for producing coating composition using these, and method for producing coating |
US10428168B2 (en) | 2015-02-17 | 2019-10-01 | Fujifilm Corporation | Composition for polymerization, method for producing same, composition for a coating containing composition for polymerization, method for producing composition for a coating using composition for polymerization, and method for producing coating |
CN105439909A (en) * | 2015-11-19 | 2016-03-30 | 中国石油天然气股份有限公司 | Sulfonate betaine and sulfonate betaine type hydrophobic polymer, and preparation method and application thereof |
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US20230183174A1 (en) * | 2019-12-16 | 2023-06-15 | Spcm Sa | Novel sulfobetaine monomers, process for preparing same, and uses thereof |
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