JPH0443060B2 - - Google Patents
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- Publication number
- JPH0443060B2 JPH0443060B2 JP58196203A JP19620383A JPH0443060B2 JP H0443060 B2 JPH0443060 B2 JP H0443060B2 JP 58196203 A JP58196203 A JP 58196203A JP 19620383 A JP19620383 A JP 19620383A JP H0443060 B2 JPH0443060 B2 JP H0443060B2
- Authority
- JP
- Japan
- Prior art keywords
- mole
- carbon atoms
- alcohol
- group
- ethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- -1 betaine compound Chemical class 0.000 claims description 15
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002280 amphoteric surfactant Substances 0.000 claims description 8
- 229960003237 betaine Drugs 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940043348 myristyl alcohol Drugs 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- VRYGRLBNIVQXMY-UHFFFAOYSA-M sodium;acetic acid;chloride Chemical compound [Na+].[Cl-].CC(O)=O VRYGRLBNIVQXMY-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Description
本発明はベタイン化合物、更に詳しくは新規な
両性界面活性ベタイン化合物およびその製法に関
するものである。
近時両性界面活性剤に属するベタイン化合物は
広汎なPH範囲で界面活性を有し、しかもアニオ
ン、非イオン、カチオンの何れのタイプの界面活
性剤とも相溶性を有することから各産業分野で広
く利用されるに至つている。
本発明者はかゝる両性界面活性剤の有用性に着
目し鋭意新規な両性界面活性剤の研究を行つた結
果本発明に到達したもので、即ち、本発明は一般
式
（ただしＲは炭素数８〜24のアルキル，アルケ
ニル基，R′はエチレン／またはプロピレン、ｎ
は１〜50の整数、R1，R2は−C2H4OH，または
The present invention relates to betaine compounds, and more particularly to novel amphoteric surfactant betaine compounds and methods for producing the same. Recently, betaine compounds, which belong to amphoteric surfactants, are widely used in various industrial fields because they have surface activity over a wide PH range and are compatible with any type of surfactant: anionic, nonionic, or cationic. It has come to be. The present inventor focused on the usefulness of such amphoteric surfactants and conducted intensive research on new amphoteric surfactants, and as a result arrived at the present invention. (However, R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene/or propylene, n
is an integer from 1 to 50, R 1 and R 2 are −C 2 H 4 OH, or
【式】基である）で表わせるベタイ
ン化合物を新規な両性界面活性剤として提案する
ものである。
本発明のベタイン化合物は次の反応によつて合
成される。
(1) ROH＋ｎ（R′O）→RO（R′O）oＨ
（ただしＲは炭素数８〜24のアルキル，アルケ
ニル基，R′はエチレン／またはプロピレン、ｎ
は１〜50の整数、R1，R2は−C2H4OH，または
We propose a betaine compound represented by the following formula as a new amphoteric surfactant. The betaine compound of the present invention is synthesized by the following reaction. (1) ROH+n(R′O)→RO(R′O) o H (However, R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene/or propylene, n
is an integer from 1 to 50, R 1 and R 2 are −C 2 H 4 OH, or
【式】基である）、Ｍは一価のアル
カリ金属である。）
反応(1)は炭素数８〜24の高級アルコール、例え
ばオクタノール、デカノール、ラウリルアルコー
ル、ミリスチルアルコール、セチルアルコール、
ステアリルアルコール、ベヘニルアルコール、オ
レイルアルコール、炭素数11〜15のオキソ法混合
アルコール、炭素数12のセカンダリーアルコー
ル、トリテシルアルコール、１モルに公知の方法
でエチレンオキサイドまたは／およびプロピレン
オキサイドを１〜50モル付加させるものである
が、経済性および有用性の面からはラウリルアル
コール、ミリスチルアルコール、オレイルアルコ
ール、トリデシルアルコール、炭素数11〜15のオ
キソ法混合アルコール１モルにエチレンオキサイ
ドを３〜10モル付加させたものが好ましい。また
プロピレンオキサイドのみの付加物は有用性がな
い。
反応(2)はかくして得られた高級アルコールアル
キレンオキサイド付加物１モルにエピハロゲンヒ
ドリン、好ましくはエピクロルヒドリンまたはエ
ピプロムヒドリン１モルをルイス酸触媒下40〜
100℃で反応せしめる。
反応(3)は反応(2)で得られた末端ハロゲン化物１
モルにジエタノールアミンまたはジイソプロパノ
ールアミン、好ましくはジエタノールアミンを常
圧もしくは加圧下、望ましくは加圧下80〜180℃
で反応させ、次いで100℃以下でアルカリ例えば
苛性カリ、苛性ソーダ１モルの水溶液を加える
か、予じめアルカリ１モルを加え閉環エポキサイ
ド化し後ジアルカノールアミンを加え常圧下60〜
90℃で反応せしめる。
反応(4)はかくして得られた三級アミン化合物に
50〜100℃にてモノハロゲン酢酸塩好ましくはモ
ノクロル酢酸塩を反応せしめる。また反応(4)に於
いてモノハロゲン酢酸塩１モルと苛性ソーダ、苛
性カリなどを１モル加え反応せしめ、本発明の化
合物の塩として得ることも可能である。何れも５
〜30時間反応せしめる。反応(4)で得られた本発明
のベタイン化合物は場合により脱水過を行うこ
とによつて精製品が得られる。
本発明のベタイン化合物はその精製品を得る
時、何れもIRスペクトルで3470，2930，2870，
1640，1600，1470，1270，1110，（cm-）に吸収が
認められる。本発明のベタイン化合物は優れた両
性界面活性剤で、洗浄剤、浸透剤、発泡剤、湿潤
剤およびAE剤などに使用される。
次に本発明の実施例を示す。
実施例 １
ラウリルアルコール１モルにエチレンオキサイ
ド６モルを付加したポリ(6)オキシエチレンラウリ
ルエーテル１モル450ｇを四ツ口コルベンに採り、
BF3エーテラート0.5ｇを加え70℃に昇温し撹拌
しながらエピクロルヒドリン１モル92.5ｇを徐々
に30分を要し滴下し後同温度で８時間撹拌した。
その後BF3に見合う苛性ソーダ40％水溶液0.35ｇ
を加え120℃に昇温し30分N2ガスを導入して脱
水、脱エーテルを行い過し、常温で淡黄色液
状、OHV104、Cl分6.5％のラウリルポリ(6)オキ
シエチルヒドロキシプロピルクロライド538ｇを
得た。
次いでラウリルポリ(6)オキシエチルヒドロキシ
プロピルクロライド0.8モル434ｇをオートクレー
ブに採りジエタノールアミン0.8モル77.6ｇを加
え120℃に昇温し４時間反応させた後、冷却し四
ツ口コルベンに移し60℃で苛性ソーダ40％水溶液
80ｇを加え、次いでモノクロル酢酸ソーダ50％水
溶液192.8ｇを加え80℃で18時間反応せしめた。
その後N2ガスを導入し105℃にて脱水し、過し
常温で淡黄褐色液状、水分0.1％、Cl：0.01％、
Ｎ：2.10％PH（１％水溶液）7.1のベタイン化物
478ｇを得た。本品については後記のテストに供
する。
実施例 ２
ミリスチルアルコール１モルにプロピレンオキ
サイド２モル、エチレンオキサイド５モルを付加
したポリ(2)オキシプロピレンポリ(5)オキシエチレ
ンミリスチルエーテル544ｇを四ツ口コルベンに
採りBF3エーテラート0.6ｇを加え70℃に昇温し
撹拌しながらエピプロムヒドリン１モル127ｇを
徐々に30分を要し滴下し後同温度で８時間撹拌し
た。その後苛性ソーダ40％液0.39ｇを加え120℃
に昇温し脱水、脱エーテル化を30分行い、次いで
過し、常温で淡黄色液状、OHV82.5、Br：
11.7％のミリスチルポリ(2)オキシプロピルポリ(5)
オキシエチルヒドロキシプロピルプロマイド666
ｇを得た。
次いで得られたポリ(2)オキシプロピルポリ(5)オ
キシエチルヒドロキシプロピルプロマイド0.8モ
ル536.8ｇを四ツ口コルペンに採り、ジプロパノ
ールアミン0.8モル234.4ｇを加え90℃で10時間反
応させアミン価が０となり反応終了を確認し、50
℃に冷却し苛性ソーダ40％水溶液192.8ｇを加え、
次いでモノクロル酢酸ソーダ50％水溶液192.8ｇ
を加え80℃で24時間反応せしめた。その後N2ガ
スを導入し105℃にて脱水し過し、常温で淡黄
褐色液状、水分0.05％、Br：０％、Ｎ：1.29％、
PH（１％）6.8のベタイン化物716ｇを得た。
本品については後記のテストに供する。
実施例 ３〜18
実施例１および実施例２と同様に表１の如く実
施例３〜15を合成した。
これらについては後記のテストに供する。
実施例で得られた合成物の溶解性と界面活性実
施例１〜18についての溶解性と界面活性について
表２に示す。表２の通り実施例１〜18の合成物は
何れも優れた界面活性を有する。[Formula] is a group), M is a monovalent alkali metal. ) Reaction (1) is a higher alcohol having 8 to 24 carbon atoms, such as octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol,
Add 1 to 50 moles of ethylene oxide or/and propylene oxide to 1 mole of stearyl alcohol, behenyl alcohol, oleyl alcohol, oxo mixed alcohol having 11 to 15 carbon atoms, secondary alcohol having 12 carbon atoms, tritacyl alcohol, by a known method. However, from the viewpoint of economy and usefulness, it is recommended to add 3 to 10 moles of ethylene oxide to 1 mole of lauryl alcohol, myristyl alcohol, oleyl alcohol, tridecyl alcohol, or oxo mixed alcohol having 11 to 15 carbon atoms. Preferably. Also, adducts of only propylene oxide have no utility. Reaction (2) is to react 1 mole of the higher alcohol alkylene oxide adduct thus obtained with 1 mole of epihalogenhydrin, preferably epichlorohydrin or epipromhydrin, under a Lewis acid catalyst for 40 to 40 minutes.
Let it react at 100℃. Reaction (3) is the terminal halide 1 obtained in reaction (2).
mol of diethanolamine or diisopropanolamine, preferably diethanolamine, at normal pressure or under pressure, preferably at 80 to 180°C under pressure.
Then, at 100℃ or less, add an alkali such as caustic potash or a 1 mol aqueous solution of caustic soda, or add 1 mol of an alkali in advance to form a ring-closing epoxide, then add dialkanolamine and react under normal pressure for 60 to 70 minutes.
Let it react at 90℃. Reaction (4) results in the tertiary amine compound thus obtained.
A monohalogen acetate, preferably a monochloroacetate, is reacted at 50 to 100°C. It is also possible to obtain the salt of the compound of the present invention by adding and reacting 1 mol of monohalogen acetate with 1 mol of caustic soda, caustic potash, etc. in reaction (4). All 5
Allow to react for ~30 hours. The betaine compound of the present invention obtained in reaction (4) can be optionally dehydrated to obtain a purified product. When the betaine compound of the present invention is purified, its IR spectrum shows 3470, 2930, 2870,
Absorption is observed at 1640, 1600, 1470, 1270, 1110, (cm - ). The betaine compound of the present invention is an excellent amphoteric surfactant and is used in cleaning agents, penetrating agents, foaming agents, wetting agents, AE agents, etc. Next, examples of the present invention will be shown. Example 1 450 g of 1 mole of poly(6)oxyethylene lauryl ether, which is obtained by adding 6 moles of ethylene oxide to 1 mole of lauryl alcohol, was placed in a four-necked colben.
0.5 g of BF 3 etherate was added, the temperature was raised to 70°C, and while stirring, 92.5 g of epichlorohydrin (1 mol) was gradually added dropwise over 30 minutes, followed by stirring at the same temperature for 8 hours.
Then 0.35 g of 40% aqueous solution of caustic soda corresponding to BF 3
The temperature was raised to 120°C, and N2 gas was introduced for 30 minutes for dehydration and deetherification. 538g of lauryl poly(6)oxyethylhydroxypropyl chloride was obtained as a pale yellow liquid at room temperature, OHV104, and Cl content of 6.5%. Obtained. Next, 434 g of lauryl poly(6) oxyethyl hydroxypropyl chloride (0.8 mol) was placed in an autoclave, 0.8 mol (77.6 g) of diethanolamine was added thereto, the temperature was raised to 120°C, the reaction was allowed to proceed for 4 hours, the temperature was raised to 120°C, and the reaction was allowed to proceed for 4 hours. % aqueous solution
Then, 192.8 g of a 50% aqueous solution of monochlorosodium acetate was added and reacted at 80° C. for 18 hours.
After that, N2 gas was introduced and dehydrated at 105℃, and at room temperature it became a pale yellowish brown liquid, moisture 0.1%, Cl: 0.01%,
N: 2.10% PH (1% aqueous solution) 7.1 betainate
Obtained 478g. This product will be subjected to the tests described below. Example 2 544 g of poly(2) oxypropylene poly(5) oxyethylene myristyl ether prepared by adding 2 moles of propylene oxide and 5 moles of ethylene oxide to 1 mole of myristyl alcohol was placed in a four-necked colben, and 0.6 g of BF 3 etherate was added thereto. The temperature was raised to .degree. C., and while stirring, 1 mole of epipromhydrin (127 g) was gradually added dropwise over 30 minutes, followed by stirring at the same temperature for 8 hours. Then add 0.39g of 40% caustic soda solution and heat to 120℃.
Dehydration and de-etherification were carried out for 30 minutes at a temperature raised to
11.7% myristyl poly(2)oxypropyl poly(5)
Oxyethyl hydroxypropyl bromide 666
I got g. Next, 0.8 mol 536.8 g of the obtained poly(2)oxypropylpoly(5)oxyethylhydroxypropyl bromide was placed in a four-necked Colpen, 0.8 mol 234.4 g of dipropanolamine was added, and the amine value was reacted at 90°C for 10 hours. 0, confirming the completion of the reaction, and 50
Cool to ℃, add 192.8 g of 40% caustic soda aqueous solution,
Next, 192.8g of 50% aqueous solution of monochloroacetic acid soda
was added and reacted at 80°C for 24 hours. After that, N2 gas was introduced and dehydrated and filtered at 105℃, leaving a light yellowish brown liquid at room temperature, moisture 0.05%, Br: 0%, N: 1.29%,
716 g of a betainate with a pH (1%) of 6.8 was obtained. This product will be subjected to the tests described below. Examples 3 to 18 Examples 3 to 15 were synthesized in the same manner as in Examples 1 and 2 as shown in Table 1. These will be subjected to the tests described later. Solubility and surface activity of the compounds obtained in Examples Table 2 shows the solubility and surface activity of Examples 1 to 18. As shown in Table 2, the compounds of Examples 1 to 18 all have excellent surface activity.
【表】【table】
【表】【table】
【表】【table】
【表】
溶解性は実施例１〜18：１ｇ、テスト液：99ｇ
を混合し20℃での状態を示す。[Table] Solubility is Examples 1 to 18: 1g, test solution: 99g
The state after mixing and at 20℃ is shown.
Claims (1)
ニル基、R′はエチレンおよび／またはプロピレ
ン、ｎは１〜50の整数、R1，R2は−C2H4OHま
たは【式】である）で表わされる両 性界面活性ベタイン化合物。 ２ 炭素数８〜24の高級アルコール１モルにエチ
レンオキサイドおよび／またはプロピレンオキサ
イドを１〜50モル付加させたポリオキシアルキレ
ンアルキルエーテルまたはポリオキシアルキレン
アルケニルエーテル１モルにエピハロゲンヒドリ
ン１モルを反応させ、末端−OH基を
【式】基（但しＸはハロゲン原 子）と置換せしめ、次いでジエタノールアミンま
たはジイソプロパノールアミン１モルとアルカリ
１モルとを反応させ末端−Ｘ基を【式】基 （ただしR1，R2はヒドロキシエチルまたはヒドロ
キシイソプロピル）と置換せしめ得られた化合物
をモノハロゲン酢酸塩１モルと反応せしめること
を特徴とする両性界面活性ベタイン化合物の製造
法。 ３ 一般式中Ｒがラウリル，トリデシル，テトラ
デシル，オレイルおよび炭素数11〜15の混合アル
キル基、R′がエチレン、ｎが２〜10、R1，R2が
ヒドロキシエチルであることを特徴とする特許請
求範囲第１項記載の両性界面活性ベタイン化合
物。[Claims] 1. The following general formula (R is an alkyl or alkenyl group having 8 to 24 carbon atoms, R' is ethylene and/or propylene, n is an integer of 1 to 50, and R 1 and R 2 are -C 2 H 4 OH or [Formula] ) is an amphoteric surfactant betaine compound. 2. Reacting 1 mole of epihalogenhydrin with 1 mole of polyoxyalkylene alkyl ether or polyoxyalkylene alkenyl ether obtained by adding 1 to 50 moles of ethylene oxide and/or propylene oxide to 1 mole of higher alcohol having 8 to 24 carbon atoms, The terminal -OH group is replaced with a [Formula] group ( wherein 1. A method for producing an amphoteric surface-active betaine compound, characterized in that R 2 is substituted with hydroxyethyl or hydroxyisopropyl) and the resulting compound is reacted with 1 mol of monohalogen acetate. 3 In the general formula, R is lauryl, tridecyl, tetradecyl, oleyl, or a mixed alkyl group having 11 to 15 carbon atoms, R' is ethylene, n is 2 to 10, and R 1 and R 2 are hydroxyethyl. An amphoteric surfactant betaine compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58196203A JPS6089456A (en) | 1983-10-21 | 1983-10-21 | Ampholytic surface-active betaine compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58196203A JPS6089456A (en) | 1983-10-21 | 1983-10-21 | Ampholytic surface-active betaine compound and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6089456A JPS6089456A (en) | 1985-05-20 |
| JPH0443060B2 true JPH0443060B2 (en) | 1992-07-15 |
Family
ID=16353906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58196203A Granted JPS6089456A (en) | 1983-10-21 | 1983-10-21 | Ampholytic surface-active betaine compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6089456A (en) |
-
1983
- 1983-10-21 JP JP58196203A patent/JPS6089456A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6089456A (en) | 1985-05-20 |
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