JPH04257552A - Novel cationic compound, its production and surfactant comprising the compound - Google Patents
Novel cationic compound, its production and surfactant comprising the compoundInfo
- Publication number
- JPH04257552A JPH04257552A JP1989091A JP1989091A JPH04257552A JP H04257552 A JPH04257552 A JP H04257552A JP 1989091 A JP1989091 A JP 1989091A JP 1989091 A JP1989091 A JP 1989091A JP H04257552 A JPH04257552 A JP H04257552A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- formula
- compound
- alkyl group
- 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.)
- Pending
Links
- 150000001767 cationic compounds Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000004094 surface-active agent Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 title abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000005526 alkyl sulfate group Chemical group 0.000 claims description 5
- -1 amine chloride Chemical class 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004949 mass spectrometry Methods 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QIKIJFUVHGOQOK-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-dimethyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC(O)CCl QIKIJFUVHGOQOK-UHFFFAOYSA-M 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000007794 irritation Effects 0.000 description 4
- JSCRBGDMRPOYAZ-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCNCCO JSCRBGDMRPOYAZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JTTBZVHEXMQSMM-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-dodecyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC(O)CCl JTTBZVHEXMQSMM-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- KWTFEBYZFYIHFO-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNCCO KWTFEBYZFYIHFO-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- KDRUIMNNZBMLJR-UHFFFAOYSA-N 2-isopropylaminoethylamine Chemical compound CC(C)NCCN KDRUIMNNZBMLJR-UHFFFAOYSA-N 0.000 description 1
- KTLIZDDPOZZHCD-UHFFFAOYSA-N 3-(2-aminoethylamino)propan-1-ol Chemical compound NCCNCCCO KTLIZDDPOZZHCD-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- PFKRTWCFCOUBHS-UHFFFAOYSA-N dimethyl(octadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)C PFKRTWCFCOUBHS-UHFFFAOYSA-N 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000774 hypoallergenic effect Effects 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- OWKYZAGJTTTXOK-UHFFFAOYSA-N n'-propylpropane-1,3-diamine Chemical compound CCCNCCCN OWKYZAGJTTTXOK-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【0001】0001
【産業上の利用分野】本発明は新規なカチオン化合物及
びその製造方法に関するものである。更に詳細には、皮
膚に対して温和な作用を有し、しかも優れた柔軟性を有
する頭髪用リンス基剤として有用なカチオン化合物及び
その製造方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel cationic compound and a method for producing the same. More specifically, the present invention relates to a cationic compound useful as a hair rinse base that has a mild effect on the skin and excellent flexibility, and a method for producing the same.
【0002】0002
【従来の技術及び発明が解決しようとする課題】近年、
リンス基剤などに使用される界面活性剤は、界面活性能
のほかに安全性、眼や皮膚に対する低刺激性などの諸特
性に優れているものが要望されている。現在使用されて
いるリンス基剤は以下のようなカチオン活性剤が良く知
られている。[Prior art and problems to be solved by the invention] In recent years,
Surfactants used in rinse bases and the like are required to have excellent properties, such as safety and low irritation to the eyes and skin, in addition to surfactant ability. Among the currently used rinse bases, the following cationic activators are well known.
【0003】<モノアルキルトリメチルアンモニウム塩
><Monoalkyltrimethylammonium salt>
【0004】0004
【化7】[C7]
【0005】<ジアルキルジメチルアンモニウム塩><Dialkyldimethylammonium salt>
【
0006】[
0006
【化8】[Chemical formula 8]
【0007】しかしながら、これらのカチオン活性剤は
リンスとして使用する場合、安全性は良くても皮膚に対
する刺激性に問題があることが多い。このため柔軟性に
優れ、且つ、安全性が高く、低刺激性である活性剤の出
現が強く望まれている。However, when these cationic active agents are used as a rinse, although they are safe, they often have problems with skin irritation. Therefore, there is a strong desire for an active agent that has excellent flexibility, high safety, and low irritation.
【0008】[0008]
【課題を解決するための手段】本発明者らは上記現状に
鑑み、頭髪用リンス基剤として柔軟性に優れ、且つ安全
性が高く、低刺激性である化合物に関して鋭意検討を行
った結果、下記一般式(1) で表される新規カチオン
化合物が本発明の目的に合致することを見出し、本発明
を完成させるに至った。[Means for Solving the Problems] In view of the above-mentioned current situation, the present inventors have conducted intensive studies on compounds that are highly flexible, highly safe, and hypoallergenic as hair rinse bases. The present inventors have discovered that a novel cationic compound represented by the following general formula (1) meets the objectives of the present invention, and have completed the present invention.
【0009】即ち、本発明は、一般式(1)That is, the present invention provides general formula (1)
【0010
】0010
]
【化9】[Chemical formula 9]
【0011】〔式中、R1は直鎖又は分岐の炭素数7〜
21のアルキル基又はアルケニル基、R2,R3は同一
又は異なる炭素数1〜3のアルキル基、R4は直鎖又は
分岐の炭素数8〜22のアルキル基又はアルケニル基、
X はH 又は炭素数1〜3のアルキル基あるいはヒド
ロキシアルキル基、Y はH 又はヒドロキシ基、A
はOH、ハロゲン原子又は炭素数1〜4のアルキル硫酸
基を表す。m は2又は3の整数を表す。n は0又は
1〜5の整数を表し、 n=1の場合は Y=H 又は
ヒドロキシ基を表し、n =0,2,3,4,5の場合
は Y=H を表す。〕で表される新規なカチオン化合
物及びその製造方法並びにこの化合物からなる界面活性
剤を提供するものである。[In the formula, R1 is a straight chain or branched chain having 7 to 7 carbon atoms]
21 alkyl group or alkenyl group, R2 and R3 are the same or different alkyl group having 1 to 3 carbon atoms, R4 is a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms,
X is H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, Y is H or a hydroxy group, A
represents OH, a halogen atom, or an alkyl sulfate group having 1 to 4 carbon atoms. m represents an integer of 2 or 3. n represents 0 or an integer from 1 to 5; when n=1, it represents Y=H or a hydroxy group; when n=0, 2, 3, 4, 5, it represents Y=H. The present invention provides a novel cationic compound represented by the following formula, a method for producing the same, and a surfactant comprising this compound.
【0012】以下、本発明について詳細に説明する。前
記一般式(1) で表されるカチオン化合物に関する報
告は従来の文献、特許公報等になく、かかる本発明のカ
チオン化合物は新規である。上記一般式(1) で表さ
れる本発明のカチオン化合物は、次の2つの製造方法<
1>又は<2>で製造することができる。The present invention will be explained in detail below. There are no reports regarding the cationic compound represented by the general formula (1) in conventional literature, patent publications, etc., and the cationic compound of the present invention is novel. The cationic compound of the present invention represented by the above general formula (1) can be produced by the following two methods.
1> or <2>.
【0013】製造方法<1> 「イミダゾリン化」 一般式(5)Manufacturing method <1> "Imidazolinization" General formula (5)
【0014】[0014]
【化10】[Chemical formula 10]
【0015】〔式中、R1は直鎖又は分岐の炭素数7〜
21のアルキル基又はアルケニル基、R’はH 又は炭
素数1〜3のアルキル基を表す。〕で表される脂肪酸又
は脂肪酸エステルと、一般式(6)
H2N(CH2)m NHX
(6)〔式中、X はH 又は炭素数1〜3のア
ルキル基あるいはヒドロキシアルキル基を表す。m は
2又は3の整数を表す。〕で表されるジアミンとを、脂
肪酸又は脂肪酸エステル(5)に対してジアミン(6)
を1〜3倍モル用いて反応させて、一般式(7)[In the formula, R1 is a straight chain or branched chain having 7 to 7 carbon atoms]
21 alkyl group or alkenyl group, R' represents H or an alkyl group having 1 to 3 carbon atoms. ] A fatty acid or fatty acid ester represented by the general formula (6) H2N(CH2)m NHX
(6) [Wherein, X represents H, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group. m represents an integer of 2 or 3. ] and diamine (6) to fatty acid or fatty acid ester (5).
was reacted using 1 to 3 times the mole of the general formula (7).
【0016】[0016]
【化11】[Chemical formula 11]
【0017】〔式中、R1, X, mは前記と同じ意
味を有する。〕で表されるイミダゾリンを生成せしめる
。[In the formula, R1, X, and m have the same meanings as above. ] is produced.
【0018】「アミドアミン化」次いでイミダゾリン(
7)をアルカリ条件下、加水分解することにより一般式
(2)[0018] "Amido-amination" followed by imidazoline (
7) under alkaline conditions to give the general formula (2)
【0019】[0019]
【化12】[Chemical formula 12]
【0020】〔式中、R1, X, mは前記と同
じ意味を有する。〕で表されるアミドアミンを生成せし
める。[In the formula, R1, X, and m have the same meanings as above. ] is produced.
【0021】「カチオン化」次いでアミドアミン(2)
と一般式(3)“Cationation” then amidoamine (2)
and general formula (3)
【0022】[0022]
【化13】[Chemical formula 13]
【0023】〔式中、R2, R3は同一又は異なる炭
素数1〜3のアルキル基、R4は直鎖又は分岐の炭素数
8〜22のアルキル基又はアルケニル基、Y はH 又
はヒドロキシ基、A はOH、ハロゲン原子又は炭素数
1〜4のアルキル硫酸基を表す。Z はハロゲン原子を
表す。n は0又は1〜5の整数を表し、 n=1の場
合は Y=H 又はヒドロキシ基を表し、n =0,2
,3,4,5の場合は Y=H を表す。〕で表される
カチオン化剤とを、アミドアミン(2) に対してカチ
オン化剤(3) を1〜3倍モル用いて反応せしめるこ
とにより製造することができる。[In the formula, R2 and R3 are the same or different alkyl groups having 1 to 3 carbon atoms, R4 is a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms, Y is H or a hydroxy group, A represents OH, a halogen atom, or an alkyl sulfate group having 1 to 4 carbon atoms. Z represents a halogen atom. n represents 0 or an integer from 1 to 5; when n=1, Y=H or a hydroxy group; n = 0,2
, 3, 4, and 5 represent Y=H. ] can be produced by reacting cationizing agent (3) with 1 to 3 times the mole of amidoamine (2).
【0024】本製造方法を式で具体的に示せば以下の様
である。[0024] The present manufacturing method can be concretely illustrated by the following formula.
【0025】[0025]
【化14】[Chemical formula 14]
【0026】〔式中、R1, R2,R3,R4, R
’,X, Y, Z, A, m, nは前記と同じ意
味を有する。〕脂肪酸又は脂肪酸エステル(5)とジア
ミン(6) との反応は、減圧下、加熱することにより
脱水反応を行いイミダゾリン(7) を合成する。その
後、アルカリ触媒存在下加水分解反応を行うことにより
高選択的にアミドアミン(2) を合成できる。[In the formula, R1, R2, R3, R4, R
', X, Y, Z, A, m, n have the same meanings as above. ] In the reaction between the fatty acid or fatty acid ester (5) and the diamine (6), a dehydration reaction is carried out by heating under reduced pressure to synthesize the imidazoline (7). Thereafter, amidoamine (2) can be synthesized with high selectivity by carrying out a hydrolysis reaction in the presence of an alkali catalyst.
【0027】アミドアミン(2) とカチオン化剤(3
) との反応は、通常アミドアミン(2) のアルコー
ル溶液にカチオン化剤(3)の水溶液を滴下した後に、
pHを8〜12に保つことが好ましく、その為に水酸化
ナトリウム、水酸化カリウム等のアルカリ溶液を必要に
応じて反応溶液中に仕込むことが行われる。反応時、反
応系のpHを前記範囲に維持するのは、アミドアミン(
2) とカチオン化剤(3) とを反応させるためであ
る。それは反応速度の点でpH8以上のアルカリ側であ
ることが好ましく、またpH12を超えるとカチオン化
剤(3) が加水分解を起こすので好ましくない。反応
は常温でも進行するが、温度が高いほど反応は速くなる
。しかし、温度、pHが高いとカチオン化剤(3) の
加水分解が促進されるため、100 ℃以下、好ましく
は90℃以下である。Amidamine (2) and cationizing agent (3)
) The reaction with cationizing agent (3) is usually carried out by dropping an aqueous solution of cationizing agent (3) into an alcoholic solution of amidoamine (2).
It is preferable to maintain the pH at 8 to 12, and for this purpose, an alkaline solution such as sodium hydroxide or potassium hydroxide is added to the reaction solution as necessary. During the reaction, amidoamine (
This is to cause the reaction between 2) and the cationizing agent (3). From the viewpoint of reaction rate, it is preferable to use an alkaline pH of 8 or more, and a pH exceeding 12 is not preferable because the cationizing agent (3) will undergo hydrolysis. The reaction proceeds even at room temperature, but the higher the temperature, the faster the reaction. However, if the temperature and pH are high, hydrolysis of the cationizing agent (3) is promoted, so the temperature is 100°C or lower, preferably 90°C or lower.
【0028】本製造方法において、カチオン化剤(3)
とアミドアミン(2) とのモル比は、通常1/1〜
3/1が好ましく、更に好ましくは 1.1/1〜 1
.5/1である。
この範囲よりカチオン化剤(3) が少ない場合は反応
率が低下し、この範囲よりカチオン化剤(3) が多い
場合にはカチオン化剤(3) 又はカチオン化剤(3)
の加水分解物が反応混合物中に多く残存するので好ま
しくない。アミドアミン(2)とカチオン化剤(3)
との反応終点は、反応中のアミドアミン(2)の残量を
高速液体クロマトグラフィーを用いて分析することによ
り確認することができる。[0028] In this production method, the cationizing agent (3)
The molar ratio of and amidoamine (2) is usually 1/1 to
3/1 is preferable, more preferably 1.1/1 to 1
.. It is 5/1. If the amount of cationizing agent (3) is less than this range, the reaction rate will decrease, and if the amount of cationizing agent (3) is more than this range, cationizing agent (3) or cationizing agent (3) will decrease.
This is not preferable because a large amount of the hydrolyzate remains in the reaction mixture. Amidamine (2) and cationizing agent (3)
The end point of the reaction can be confirmed by analyzing the remaining amount of amidoamine (2) during the reaction using high performance liquid chromatography.
【0029】本製造方法における反応溶液は、水溶液、
又は水溶液とエタノール、イソプロピルアルコール等の
低級アルコールや、1,3 −プロパンジオール、プロ
ピレングリコール等のジオール類との混合溶液のいずれ
でも差支えない。[0029] The reaction solution in this production method is an aqueous solution,
Alternatively, a mixed solution of an aqueous solution and a lower alcohol such as ethanol or isopropyl alcohol, or a diol such as 1,3-propanediol or propylene glycol may be used.
【0030】製造方法<2>
「イミダゾリン化」と「アミドアミン化」について
は、製造方法<1>に記載した方法にて行った。Production method <2>"Imidazolination" and "amide amination" were carried out by the method described in production method <1>.
【0031】「カチオン化」アミドアミン(2) と一
般式(4)“Cationized” amidoamine (2) and general formula (4)
【0032】[0032]
【化15】[Chemical formula 15]
【0033】〔式中、R2, R3, R4,
A は前記の意味を有する。〕で表されるカチオン化
剤(グリシジルトリアルキルアンモニウム塩)とを反応
させて、一般式(1’)[In the formula, R2, R3, R4,
A has the meaning given above. ] by reacting with a cationizing agent (glycidyl trialkylammonium salt) represented by the general formula (1')
【0034】[0034]
【化16】[Chemical formula 16]
【0035】〔式中、R1, R2, R3, R4,
X, A, m は前記の意味を有する。〕で表され
る化合物を得る。[In the formula, R1, R2, R3, R4,
X, A, m have the meanings given above. ] is obtained.
【0036】本製造方法を式で具体的に示せば以下の様
である。[0036] This manufacturing method can be concretely illustrated by the following formula.
【0037】[0037]
【化17】[Chemical formula 17]
【0038】〔式中、R1, R2, R3, R4,
R’,X, A, m は前記と同じ意味を有する。
〕グリシジルトリアルキルアンモニウム塩(4) とア
ミドアミン(2) との反応において、グリシジルトリ
アルキルアンモニウム塩(4) とアミドアミン(2)
とのモル比は1/1〜3/1である。モル比がこの範
囲を下廻る場合は反応性が低下し、またモル比がこの範
囲を超える場合には反応混合物中にグリシジルトリアル
キルアンモニウム塩(4) の加水分解物が多く残存す
るので好ましくない。また反応温度は30〜120 ℃
、好ましくは50〜90℃である。反応温度がこの範囲
より低い場合は反応速度が遅く、この範囲を超える場合
には着色等が起こるので好ましくない。アミドアミン(
2) とグリシジルトリアルキルアンモニウム塩(4)
との反応において、反応性を確保し、一定の反応を進
行させる為には、適当量のアルカリ水溶液を仕込み、p
Hを8〜12に維持することが好ましい。pHがこの範
囲未満の場合は反応速度が遅くなり、この範囲を超える
場合は副生成物が多く生成し収率が低下する。[In the formula, R1, R2, R3, R4,
R', X, A, m have the same meanings as above. ] In the reaction between glycidyltrialkylammonium salt (4) and amidoamine (2), glycidyltrialkylammonium salt (4) and amidoamine (2)
The molar ratio with is 1/1 to 3/1. If the molar ratio is below this range, the reactivity will decrease, and if the molar ratio exceeds this range, a large amount of the hydrolyzate of the glycidyl trialkylammonium salt (4) will remain in the reaction mixture, which is undesirable. . Also, the reaction temperature is 30-120℃
, preferably 50 to 90°C. If the reaction temperature is lower than this range, the reaction rate will be slow, and if it exceeds this range, coloring etc. will occur, which is not preferable. Amidamine (
2) and glycidyl trialkylammonium salt (4)
In the reaction with p.
It is preferred to maintain H between 8 and 12. If the pH is less than this range, the reaction rate will be slow, and if it exceeds this range, many by-products will be produced and the yield will be reduced.
【0039】また、本製造方法<2>においてイミダゾ
リル化及びアミドアミン化の条件は製造方法<1>に記
載した通りである。本発明の反応は全て空気中で行って
も良いし、不活性ガス雰囲気中で行っても良いが、着色
等の点で不活性ガス雰囲気下が好ましい。Furthermore, in the present production method <2>, the conditions for imidazolylation and amidoamination are as described in production method <1>. All reactions of the present invention may be carried out in air or in an inert gas atmosphere, but an inert gas atmosphere is preferable from the viewpoint of coloring and the like.
【0040】本発明に用いられる前記一般式(5)で表
される脂肪酸又は脂肪酸エステルとしては、例えばカプ
リル酸、カプリン酸、ラウリン酸、ミリスチン酸、パル
ミチン酸、ステアリン酸、ベヘン酸、或いはヤシ組成、
牛脂組成等を持つ脂肪酸又はこれら脂肪酸のエステルが
挙げられ、また前記一般式(6) で表されるジアミン
としてはエチレンジアミン、N −メチルエチレンジア
ミン、N −エチルエチレンジアミン、N −イソプロ
ピルエチレンジアミン、アミノエチルエタノールアミン
、 N−(2−ヒドロキシプロピル)エチレンジアミン
、N −(3−ヒドロキシプロピル)エチレンジアミン
、N −メチルトリメチレンジアミン、N −エチルト
リメチレンジアミン、N −プロピルトリメチレンジア
ミンなどを挙げることが出来る。The fatty acid or fatty acid ester represented by the general formula (5) used in the present invention includes, for example, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, or coconut acid. ,
Examples of fatty acids having a beef tallow composition and esters of these fatty acids include ethylenediamine, N-methylethylenediamine, N-ethylethylenediamine, N-isopropylethylenediamine, and aminoethylethanolamine. , N-(2-hydroxypropyl)ethylenediamine, N-(3-hydroxypropyl)ethylenediamine, N-methyltrimethylenediamine, N-ethyltrimethylenediamine, N-propyltrimethylenediamine, and the like.
【0041】[0041]
【発明の効果】本発明方法によって取得された化合物は
界面活性を有し、かかる化合物を主成分とした界面活性
剤は柔軟性に優れ、且つ低刺激性であるために頭髪用リ
ンス基剤として供することができる。[Effects of the Invention] The compound obtained by the method of the present invention has surface activity, and the surfactant containing such a compound as a main component has excellent flexibility and low irritation, so it can be used as a hair conditioner base. can be provided.
【0042】[0042]
【実施例】次に、本発明を実施例に基づいて詳細に説明
するが、本発明の範囲はこれらによって限定されるもの
ではない。EXAMPLES Next, the present invention will be explained in detail based on Examples, but the scope of the present invention is not limited by these.
【0043】実施例1
カチオン化〔化合物(1) の合成〕
撹拌器、冷却管、温度計、滴下漏斗を備えた1リッ
トル容−4ツ口フラスコに、2−ラウロイルアミノエチ
ル−2−ヒドロキシエチルアミン286 g(1モル)
、エタノール286gを仕込み、撹拌しながら70〜8
0℃まで加熱した。その後、上記混合物を撹拌しながら
、pH電極を液中に挿入し、40%水酸化ナトリウム水
溶液を滴下しpHを10とした。次に、3−クロロ−2
−ヒドロキシプロピル−N −ステアリル−N,N −
ジメチルアンモニウムクロライド(MW426) の3
0%水溶液1846g(1.3 モル)を2時間で滴下
した。この間、pH10を維持する為、40%水酸化ナ
トリウムを適宜滴下した。3−クロロ−2−ヒドロキシ
プロピル−N −ステアリル−N,N −ジメチルアン
モニウムクロライドの滴下が終了した後、pH10を維
持しながら加熱と攪拌を継続し、1時間毎に高速液体ク
ロマトグラフィーにて2−ラウロイルアミノエチル−2
−ヒドロキシエチルアミンの残量を確認した。Example 1 Cationization [Synthesis of Compound (1)] 2-Lauroylaminoethyl-2-hydroxyethylamine was placed in a 1 liter four-necked flask equipped with a stirrer, a condenser, a thermometer, and a dropping funnel. 286 g (1 mole)
, add 286g of ethanol, and add 70~8g while stirring.
Heated to 0°C. Thereafter, a pH electrode was inserted into the mixture while stirring the mixture, and a 40% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 10. Next, 3-chloro-2
-Hydroxypropyl-N-stearyl-N,N-
Dimethylammonium chloride (MW426) 3
1846 g (1.3 mol) of a 0% aqueous solution was added dropwise over 2 hours. During this time, 40% sodium hydroxide was appropriately added dropwise to maintain the pH at 10. After the dropwise addition of 3-chloro-2-hydroxypropyl-N-stearyl-N,N-dimethylammonium chloride was completed, heating and stirring were continued while maintaining the pH of 10, and every hour 2 -Lauroylaminoethyl-2
-The remaining amount of hydroxyethylamine was confirmed.
【0044】3−クロロ−2−ヒドロキシプロピル−N
−ステアリル−N,N −ジメチルアンモニウムクロ
ライドの滴下が終了した6時間後に、2−ラウロイルア
ミノエチル−2−ヒドロキシエチルアミンの系内濃度が
1%になったのを確認した後、反応を終了した。3-chloro-2-hydroxypropyl-N
Six hours after the dropping of -stearyl-N,N-dimethylammonium chloride was completed, the reaction was terminated after confirming that the concentration of 2-lauroylaminoethyl-2-hydroxyethylamine in the system had reached 1%.
【0045】この反応液を電気透析装置を用いて精製し
た後、一部蒸発乾固し、IR分析、質量分析により前記
一般式(1) の化合物、N −(2−ラウロイルアミ
ノエチル)−N−(2−ヒドロキシエチル)−N −〔
3− (N’−ステアリル−N’,N’ −ジメチルア
ンモニオ)−2−ヒドロキシプロピル〕アミンクロライ
ド(下記構造式を有する)が得られた。After purifying this reaction solution using an electrodialyzer, it was partially evaporated to dryness, and the compound of general formula (1), N-(2-lauroylaminoethyl)-N, was determined by IR analysis and mass spectrometry. -(2-hydroxyethyl)-N-[
3-(N'-stearyl-N',N'-dimethylammonio)-2-hydroxypropyl]amine chloride (having the following structural formula) was obtained.
【0046】[0046]
【化18】[Chemical formula 18]
【0047】IR分析、質量分析結果
<IR分析>
1650cm−1(6.06μ)に於いてアミド特有の
強い吸収が認められた。Results of IR analysis and mass spectrometry <IR analysis> Strong absorption characteristic of amide was observed at 1650 cm -1 (6.06 μ).
【0048】<質量分析>
装 置;日本電子(株)製 SX−102 型
質量分析型
測定条件;導入方法 直接
;イオン化法 FAB(Fast Atom Bomb
erdment)分析結果;フラグメントイオン分子量
640, 226
主要ピーク2本が認められ、640は(M+−Cl)イ
オンピークであり、上記構造のカチオン化合物であるこ
とを確認した。<Mass spectrometry> Equipment: Model SX-102, manufactured by JEOL Ltd. Measurement conditions: Introduction method: Direct; Ionization method: FAB (Fast Atom Bomb)
erdment) Analysis results; fragment ion molecular weight: 640, 226 Two main peaks were observed, and 640 was the (M+-Cl) ion peak, confirming that it was a cationic compound with the above structure.
【0049】実施例2
原料脂肪酸にステアリン酸を用いて合成した2−ステア
ロイルアミノエチル−2−ヒドロキシエチルアミンを2
−ラウロイルアミノエチル−2−ヒドロキシエチルアミ
ンの代わりに用い、カチオン化剤として3−クロロ−2
−ヒドロキシプロピル−N −ラウリル−N,N −ジ
メチルアンモニウムクロライドを3−クロロ−2−ヒド
ロキシプロピル−N −ステアリル−N,N −ジメチ
ルアンモニウムクロライドの代わりに用いる以外は実施
例1と同様に行い、取得された化合物は下記の構造を有
するものであることを実施例1と同様の方法で確認した
。Example 2 2-stearoylaminoethyl-2-hydroxyethylamine synthesized using stearic acid as a raw fatty acid was
-Used in place of lauroylaminoethyl-2-hydroxyethylamine, as a cationizing agent 3-chloro-2
-Hydroxypropyl-N-lauryl-N,N-dimethylammonium chloride was used in place of 3-chloro-2-hydroxypropyl-N-stearyl-N,N-dimethylammonium chloride, but in the same manner as in Example 1, It was confirmed in the same manner as in Example 1 that the obtained compound had the following structure.
【0050】[0050]
【化19】[Chemical formula 19]
【0051】IR分析、質量分析結果
<IR分析>1650cm−1(6.06μ)に於いて
アミド特有の強い吸収が認められた。Results of IR analysis and mass spectrometry <IR analysis> Strong absorption characteristic of amide was observed at 1650 cm -1 (6.06 μ).
【0052】<質量分析>実施例1と同様の条件で行っ
た。<Mass spectrometry> It was carried out under the same conditions as in Example 1.
【0053】分析結果;フラグメントイオン分子量64
0, 310
主要ピーク2本が認められ、640は(M+−Cl)イ
オンピークであり、上記構造のカチオン化合物であるこ
とを確認した。Analysis result: Fragment ion molecular weight 64
0, 310 Two main peaks were observed, and 640 was the (M+-Cl) ion peak, confirming that it was a cationic compound with the above structure.
【0054】実施例3
カチオン化剤として3−クロロ−2−ヒドロキシプロピ
ル−N −ラウリル−N,N −ジメチルアンモニウム
クロライドを3−クロロ−2−ヒドロキシプロピル−N
−ステアリル−N,N −ジメチルアンモニウムクロ
ライドの代わりに用いる以外は実施例1と同様に行い、
取得された化合物は下記の構造を有するものであること
を実施例1と同様の方法で確認した。Example 3 3-chloro-2-hydroxypropyl-N-lauryl-N,N-dimethylammonium chloride was used as a cationizing agent.
-Producted in the same manner as in Example 1 except for using instead of -stearyl-N,N-dimethylammonium chloride,
It was confirmed in the same manner as in Example 1 that the obtained compound had the following structure.
【0055】[0055]
【化20】[C20]
【0056】<質量分析>実施例1と同様の条件で行っ
た。<Mass spectrometry> It was carried out under the same conditions as in Example 1.
【0057】分析結果;フラグメントイオン分子量55
6, 226
実施例4
原料脂肪酸にステアリン酸を用いて合成した2−ステア
ロイルアミノエチル−2−ヒドロキシエチルアミンを2
−ラウロイルアミノエチル−2−ヒドロキシエチルアミ
ンの代わりに用いる以外は実施例1と同様に行い、取得
された化合物は下記の構造を有するものであることを実
施例1と同様の方法で確認した。Analysis result: Fragment ion molecular weight 55
6, 226 Example 4 2-stearoylaminoethyl-2-hydroxyethylamine synthesized using stearic acid as a raw fatty acid
The same procedure as in Example 1 was carried out except that -lauroylaminoethyl-2-hydroxyethylamine was used instead, and it was confirmed in the same manner as in Example 1 that the obtained compound had the following structure.
【0058】[0058]
【化21】[C21]
【0059】<質量分析>実施例1と同様の条件で行っ
た。<Mass spectrometry> It was carried out under the same conditions as in Example 1.
【0060】分析結果;フラグメントイオン分子量72
4, 310
実施例5
原料ジアミンとして N−プロピル−1,3 −トリメ
チレンジアミンを用いて合成した2−ラウロイルアミノ
プロピルプロピルアミンを2−ラウロイルアミノエチル
−2−ヒドロキシエチルアミンの代わりに用い、カチオ
ン化剤として3−クロロプロピル−N −ステアリル−
N,N −ジメチルアンモニウムクロライドを3−クロ
ロ−2−ヒドロキシプロピル−N −ステアリル−N,
N −ジメチルアンモニウムクロライドの代わりに用い
る以外は実施例1と同様に行い、取得された化合物は下
記の構造を有するものであることを実施例1と同様の方
法で確認した。Analysis result: Fragment ion molecular weight 72
4,310 Example 5 2-Lauroylaminopropylpropylamine synthesized using N-propyl-1,3-trimethylenediamine as a raw material diamine was used instead of 2-lauroylaminoethyl-2-hydroxyethylamine, and cationization was performed. 3-chloropropyl-N-stearyl- as an agent
N,N-dimethylammonium chloride to 3-chloro-2-hydroxypropyl-N-stearyl-N,
The same procedure as in Example 1 was carried out except that N-dimethylammonium chloride was used instead, and it was confirmed in the same manner as in Example 1 that the obtained compound had the following structure.
【0061】[0061]
【化22】[C22]
【0062】IR分析、質量分析結果
<IR分析>1650cm−1(6.06μ)に於いて
アミド特有の強い吸収が認められた。Results of IR analysis and mass spectrometry <IR analysis> Strong absorption characteristic of amide was observed at 1650 cm -1 (6.06 μ).
【0063】<質量分析>実施例1と同様の条件で行っ
た。<Mass spectrometry> It was carried out under the same conditions as in Example 1.
【0064】分析結果;フラグメントイオン分子量63
6, 240
主要ピーク2本が認められ、636は(M+−Cl)
イオンピークであり、上記構造のカチオン化合物である
ことを確認した。Analysis result: Fragment ion molecular weight 63
6,240 Two main peaks were observed, and 636 was (M+-Cl)
It was an ion peak, and it was confirmed that it was a cationic compound with the above structure.
【0065】実施例6
カチオン化剤として、3−クロロ−2−ヒドロキシプロ
ピル−N −ステアリル−N,N −ジメチルアンモニ
ウムクロライドの代わりに2,3 −オキシプロピル−
N−ステアリル−N,N −ジメチルアンモニウムクロ
ライドを用いる以外は実施例1と同様の条件で行い、取
得された化合物は実施例1に示した化合物と同様である
ことを実施例1と同様の方法で確認した。Example 6 As a cationizing agent, 2,3-oxypropyl- was used instead of 3-chloro-2-hydroxypropyl-N-stearyl-N,N-dimethylammonium chloride.
It was carried out under the same conditions as in Example 1 except that N-stearyl-N,N-dimethylammonium chloride was used, and the obtained compound was the same as the compound shown in Example 1. I confirmed it.
【0066】試験例
実施例1〜5で得られた界面活性剤、従来柔軟性が優れ
ていることが知られている下記に示す対照化合物1につ
いて、下記に示す方法により皮膚刺激性及び柔軟性を評
価した。結果を表1に示す。Test Example The surfactants obtained in Examples 1 to 5 and the control compound 1 shown below, which is conventionally known to have excellent flexibility, were tested for skin irritation and flexibility by the method shown below. was evaluated. The results are shown in Table 1.
【0067】<対照化合物1>花王(株)製コータミン
86P(ステアリルトリメチルアンモニウムクロライド
)・皮膚刺激性試験
ヒトに対する24時間閉鎖貼付試験を行った。即ち、2
0人の被検者に界面活性剤を有効分として0.2 %含
有する水溶液0.1 mlをしみ込ませたパッチテスト
用絆創膏を24時間貼付し、貼付除去後24時間後に刺
激性を判定した。判定結果ははっきりした紅斑を示した
ものを陽性とし、その陽性率で示した。<Control Compound 1> Cortamine 86P (stearyltrimethylammonium chloride) manufactured by Kao Corporation - Skin irritation test A 24-hour closed patch test on humans was conducted. That is, 2
A patch test plaster impregnated with 0.1 ml of an aqueous solution containing 0.2% active surfactant was applied to 0 subjects for 24 hours, and irritation was determined 24 hours after removal. . The test result was determined to be positive if it showed clear erythema, and was expressed as a positive rate.
【0068】・柔軟性評価試験
各種界面活性剤1%、高級アルコール3%、プロピレン
グリコール3%となるように調整したアルコール乳化液
を、トリートメント剤の入れていないシャンプーで洗髪
した髢に髢の10重量%塗布し、1分間放置する。その
後40℃の温水で一定時間濯ぎ、タオルドライしてWE
T 時の評価を行った。その後ドライヤーで髢を乾燥さ
せ、DRY 時の評価を行った。評価結果は良好な場合
を○とし、好ましくない場合を×、中間の場合を△とし
た。・Flexibility evaluation test An alcohol emulsion adjusted to contain 1% of various surfactants, 3% of higher alcohols, and 3% of propylene glycol was applied to hair that had been washed with a shampoo containing no treatment agent. Apply % by weight and leave for 1 minute. After that, rinse with warm water at 40℃ for a certain period of time, towel dry and wash.
Evaluation was performed at T time. Thereafter, the hair was dried with a hair dryer, and a dry evaluation was performed. The evaluation results were evaluated as ◯ for good results, × for unfavorable results, and △ for intermediate results.
【0069】[0069]
【表1】[Table 1]
Claims (4)
ル基又はアルケニル基、R2,R3は同一又は異なる炭
素数1〜3のアルキル基、R4は直鎖又は分岐の炭素数
8〜22のアルキル基又はアルケニル基、X はH 又
は炭素数1〜3のアルキル基あるいはヒドロキシアルキ
ル基、Y はH 又はヒドロキシ基、A はOH、ハロ
ゲン原子又は炭素数1〜4のアルキル硫酸基を表す。m
は2又は3の整数を表す。 n は0又は1〜5の整数を表し、 n=1の場合は
Y=H 又はヒドロキシ基を表し、n =0,2,3,
4,5の場合は Y=H を表す。〕で表されるカチオ
ン化合物。Claim 1: General formula (1) [In the formula, R1 is a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms, and R2 and R3 are the same or different groups having 1 to 3 carbon atoms] alkyl group, R4 is a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms, X is H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, Y is H or a hydroxy group, A is OH, Represents a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. m
represents an integer of 2 or 3. n represents 0 or an integer from 1 to 5, and if n=1
Y=H or represents a hydroxy group, n =0,2,3,
4 and 5 represent Y=H. ] A cationic compound represented by
ル基又はアルケニル基、m は2又は3の整数を表す。 X はH 又は炭素数1〜3のアルキル基あるいはヒド
ロキシアルキル基を表す。〕で表されるアミドアミンと
、一般式(3) 【化3】 〔式中、R2, R3は同一又は異なる炭素数1〜3
のアルキル基、R4は直鎖又は分岐の炭素数8〜22の
アルキル基又はアルケニル基、Y はH 又はヒドロキ
シ基、A はOH、ハロゲン原子又は炭素数1〜4のア
ルキル硫酸基を表す。n は0又は1〜5の整数を表し
、 n=1の場合は Y=H 又はヒドロキシ基を表し
、n =0,2,3,4,5の場合は Y=H を表す
。Z はハロゲン原子を表す。〕で表されるカチオン化
剤とを反応させることを特徴とする請求項1記載の一般
式(1) で表されるカチオン化合物の製造方法。[Claim 2] General formula (2) [In the formula, R1 represents a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms, and m represents an integer of 2 or 3. X represents H, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group. ] and the general formula (3) [Formula, R2 and R3 are the same or different carbon atoms 1 to 3]
R4 represents a linear or branched alkyl group or alkenyl group having 8 to 22 carbon atoms, Y represents H or a hydroxy group, A represents OH, a halogen atom, or an alkyl sulfate group having 1 to 4 carbon atoms. n represents 0 or an integer from 1 to 5; when n=1, it represents Y=H or a hydroxy group; when n=0, 2, 3, 4, 5, it represents Y=H. Z represents a halogen atom. A method for producing a cationic compound represented by the general formula (1) according to claim 1, characterized in that the cationic compound is reacted with a cationizing agent represented by the following.
ル基又はアルケニル基、m は2又は3の整数を表す。 X はH 又は炭素数1〜3のアルキル基あるいはヒド
ロキシアルキル基を表す。〕で表されるアミドアミンと
、一般式(4) 【化5】 〔式中、R2, R3は同一又は異なる炭素数1〜3の
アルキル基、R4は直鎖又は分岐の炭素数8〜22のア
ルキル基又はアルケニル基、A はOH、ハロゲン原子
又は炭素数1〜4のアルキル硫酸基を表す。〕で表され
るカチオン化剤とを反応させることを特徴とする一般式
(1’)【化6】 〔式中、R1, R2, R3, R4, X, A,
m は前記の意味を有する。〕で表されるカチオン化
合物の製造方法。[Claim 3] General formula (2) [In the formula, R1 represents a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms, and m represents an integer of 2 or 3. X represents H, an alkyl group having 1 to 3 carbon atoms, or a hydroxyalkyl group. [In the formula, R2 and R3 are the same or different alkyl groups having 1 to 3 carbon atoms, and R4 is a linear or branched alkyl group having 8 to 22 carbon atoms. The alkyl group or alkenyl group, A represents OH, a halogen atom, or an alkyl sulfate group having 1 to 4 carbon atoms. [In the formula, R1, R2, R3, R4, X, A,
m has the meaning given above. ] A method for producing a cationic compound represented by
れるカチオン化合物からなる界面活性剤。4. A surfactant comprising a cationic compound represented by the general formula (1) according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1989091A JPH04257552A (en) | 1991-02-13 | 1991-02-13 | Novel cationic compound, its production and surfactant comprising the compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1989091A JPH04257552A (en) | 1991-02-13 | 1991-02-13 | Novel cationic compound, its production and surfactant comprising the compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04257552A true JPH04257552A (en) | 1992-09-11 |
Family
ID=12011792
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1989091A Pending JPH04257552A (en) | 1991-02-13 | 1991-02-13 | Novel cationic compound, its production and surfactant comprising the compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04257552A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7824667B2 (en) | 2001-04-30 | 2010-11-02 | Cognis Ip Management Gmbh | Use of cationic preparations |
-
1991
- 1991-02-13 JP JP1989091A patent/JPH04257552A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7824667B2 (en) | 2001-04-30 | 2010-11-02 | Cognis Ip Management Gmbh | Use of cationic preparations |
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