JPS6151561B2 - - Google Patents
Info
- Publication number
- JPS6151561B2 JPS6151561B2 JP59151172A JP15117284A JPS6151561B2 JP S6151561 B2 JPS6151561 B2 JP S6151561B2 JP 59151172 A JP59151172 A JP 59151172A JP 15117284 A JP15117284 A JP 15117284A JP S6151561 B2 JPS6151561 B2 JP S6151561B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- hydroxyethyl
- weight
- product
- aminoethyl
- 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
Links
- 239000003599 detergent Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000000774 hypoallergenic effect Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 235000019864 coconut oil Nutrition 0.000 description 9
- 239000003240 coconut oil Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 150000002462 imidazolines Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- -1 N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl]decanoic acid amide Chemical compound 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000004400 mucous membrane Anatomy 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 229940047670 sodium acrylate Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- 206010015946 Eye irritation Diseases 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 231100000013 eye irritation Toxicity 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- VJSLRFYBDKLPBX-UHFFFAOYSA-N 3-[2-carboxyethyl-[2-[dodecanoyl(2-hydroxyethyl)amino]ethyl]amino]propanoic acid Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCN(CCC(O)=O)CCC(O)=O VJSLRFYBDKLPBX-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- UPOFBZZSDRYRHB-UHFFFAOYSA-N 1-(2-heptadecyl-4,5-dihydroimidazol-1-yl)ethanol Chemical compound CCCCCCCCCCCCCCCCCC1=NCCN1C(C)O UPOFBZZSDRYRHB-UHFFFAOYSA-N 0.000 description 1
- RDBONSWKYPUHCS-UHFFFAOYSA-N 1-undecyl-4,5-dihydroimidazole Chemical compound CCCCCCCCCCCN1CCN=C1 RDBONSWKYPUHCS-UHFFFAOYSA-N 0.000 description 1
- MRYLNLOZWBPZLC-UHFFFAOYSA-N 2-(2-aminoethyl)dodecanamide Chemical compound CCCCCCCCCCC(C(N)=O)CCN MRYLNLOZWBPZLC-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- IUXDBQYGCOYGJJ-UHFFFAOYSA-N 3-[2-carboxyethyl-[2-[2-hydroxyethyl(octanoyl)amino]ethyl]amino]propanoic acid Chemical compound CCCCCCCC(=O)N(CCO)CCN(CCC(O)=O)CCC(O)=O IUXDBQYGCOYGJJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- 206010010726 Conjunctival oedema Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000007696 Kjeldahl method Methods 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- BFGXGUQFDXCYSL-UHFFFAOYSA-N ON1C(=NCC1)CCCCCCCCCCC Chemical compound ON1C(=NCC1)CCCCCCCCCCC BFGXGUQFDXCYSL-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000003766 combability Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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 description 1
- 125000002704 decyl 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])* 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 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 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 231100000286 mucous membrane, eye irritation or corrosion testing Toxicity 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Description
本発明は、皮ふ、眼、粘膜などに対する刺激の
少ない洗髪剤に関するものである。さらに詳しく
いえば、本発明は、一般式
（式中のＲは炭素原子７〜17個をもつ脂肪族炭
化水素基、Ｍは水素原子又はアルカリ金属原子で
ある）
で表わされる特定のジ置換脂肪族カルボン酸アミ
ドアミンを洗剤成分として含有する低刺激性洗髪
剤に関するものである。
これまで、置換アミドアミン型両性界面活性剤
としては、直鎖状脂肪族カルボン酸とアミノエチ
ルエタノールアミンとの反応により得られる、一
般式
（式中のR′は長鎖状脂肪族炭化水素残基、
M″は水素原子又はアルカリ金属原子である）で
表わされる化合物が知られている（米国特許第
3262951号及び第3941817号明細書）。
このような両性界面活性剤は、洗浄剤、繊維処
理剤、帯電防止剤、香粧品基剤などとして使用さ
れている。ところで、シヤンプー、リンスのよう
な洗髪剤の洗剤成分として界面活性剤を用いる場
合には、皮ふ、眼、粘膜などに対する刺激のない
ものもしくは少ないものが要求されるが、前記の
一般式（）の置換アミドアミン型両性界面活性
剤はこの点において十分満足すべきものとはいえ
ないため、洗髪剤用としては不適当であつた。
本発明者らは、皮ふ、眼、粘膜に対する刺激が
少ない洗髪剤を開発すべく鋭意研究を重ねた結
果、前記一般式（）で表わされるジ置換脂肪族
カルボン酸アミドアミンを洗剤成分として用いる
ことによりその目的を達成しうることを見出し、
この知見に基づいて本発明をなすに至つた。
前記一般式（）で表わされる本発明化合物の
例としては、Ｎ―（２―ヒドロキシエチル）―Ｎ
―〔ジ―（２―カルボキシエチル）アミノエチ
ル〕オクタン酸アミド、Ｎ―（２―ヒドロキシエ
チル）―Ｎ―〔ジ―（２―カルボキシエチル）ア
ミノエチル〕デカン酸アミド、Ｎ―（２―ヒドロ
キシエチル）―Ｎ―〔ジ―（２―カルボキシエチ
ル）アミノエチル〕ドデカン酸アミド、Ｎ―（２
―ヒドロキシエチル）―Ｎ―〔ジ―（２―カルボ
キシエチル）アミノエチル〕ステアリン酸アミ
ド、Ｎ―（２―ヒドロキシエチル）―Ｎ―〔ジ―
（２―カルボキシエチル）アミノエチル〕ラウリ
ン酸アミド、Ｎ―（２―ヒドロキシエチル）―Ｎ
―〔ジ―（２―カルボキシエチル）アミノエチ
ル〕ヤシ油脂肪酸アミド及びそれらのナトリウム
塩、カリウム塩などをあげることができる。
これらの化合物は、例えば一般式
（式中のＲは前記と同じ意味をもつ）
で表わされるイミダゾリン誘導体に、アクリル酸
アルキルエステル及び水を反応させ、その生成物
を水酸化アルカリでけん化することにより得るこ
とができる。
前記一般式（）で表わされるイミダゾリン誘
導体の例としては、２―位がオクチル基、ノニル
基、デシル基、ウンデシル基、ドデシル基、ペン
タデシル基、ヘキサデシル基、ヘプタデシル基の
ようなアルキル基や、オクテニル基、デセニル
基、ペンタデセニル基などのアルケニル基により
置換されている１―（２―ヒドロキシエチル）―
イミダゾリンをあげることができる。
また、のイミダゾリン誘導体と反応させるアク
リル酸アルキルエステルとしては、アクリル酸メ
チル、アクリル酸エチルのような低級アルキルエ
ステルが好ましい。このアクリル酸アルキルエス
テルは、イミダゾリン誘導体１モル当り、1.3〜
2.0モルの割合で使用される。この量が2.0モルよ
りも多くなると最終生成物中に未反応のアクリル
酸ナトリウムが多く存在するようなるし、またこ
の量が1.3モルよりも少ないと未反応アミンが多
くなり収率が低下する。
このアクリル酸アルキルエステルと同時に反応
に供される水の量は、イミダゾリン誘導体１モル
当り少なくとも１モル好ましくは2.0〜3.0モルの
範囲で選ばれる。この量が、1.0モルよりも少な
いと副生物である第二級アミンの量が増加し、目
的物の収率が低下する。
イミダゾリン誘導体とアクリル酸アルキルエス
テルと水との反応は、室温ないし100℃、好まし
くは60〜80℃の温度で行うのがよい。反応に要す
る時間は通常30分ないし４時間の範囲であるが、
多くの場合60分で約99％の転化率が得られる。こ
の反応は、所望ならばアルカリ触媒の存在下で行
うこともできるが、触媒は特に必要ではない。
このようにして得られる付加生成物は、単離さ
れることなくそのまま次の水酸化アルカリによる
けん化処理に供される。このけん化は、前記の反
応生成物に、使用したアクリル酸アルキルエステ
ルとほぼ等モル量の水酸化アルカリを加え、50〜
100℃に加熱することによつて行われる。けん化
に要する時間は通常70℃において約２時間程度で
ある。
このようにして得られた反応生成物を減圧蒸留
し、その中に含まれている低分子量成分を留去す
ると、目的化合物又はこれを主体として含む反応
生成物が白色固体として残留する。このようにし
て得られる目的化合物の白色固体は薄層クロマト
グラフイーにかけたところ、１個のスポツトを示
し、純品であることが確認された。また、このも
のが前記一般式（）の構造を有することは赤外
線吸収スペクトル、核磁気共鳴スペクトル及び元
素分析などによつて確認された。
これらの化合物は従来の類似構造をもつ界面活
性剤と比較し、皮ふ、眼、粘膜に対する刺激性が
著しく低いという特徴を有している。
本発明の洗髪剤は、前記一般式（）で表わさ
れる化合物を洗剤成分として含有するもので、シ
ヤンプーやヘアーリンスの形に調製して用いられ
る。その中の前記化合物の含有量としては、これ
までのシヤンプーやヘアーリンスにおいて通常使
用されている洗剤成分の場合に必要とされる濃度
と特に変わりはなく、少なくとも２重量％以上の
濃度で使用目的に応じ適宜選択される。また、本
発明の洗髪剤には洗剤成分の外に、シヤンプーや
ヘアーリンスに慣用されている各種の添加剤例え
ば保存剤、香料、色素などを添加することもでき
るし、眼、粘膜などの刺激を生じない範囲の濃度
で他の界面活性剤を併用することもできる。
次に参考例、実施例により本発明をさらに詳細
に説明する。
参考例 １
かきまぜ機、冷却管及び温度計を備えた２容
の四つ口フラスコに、１―ヒドロキシエチル―２
―ウンデシルイミダゾリン268g（1.0モル）とア
クリル酸エチル200g（2.0モル）とを装入し、25
〜35℃で30分間かきまぜたのち、水36g（2.0モ
ル）を添加する。この際発熱して温度が70℃まで
上昇するので、この温度において２時間反応させ
たのち、エチルアルコール400mlと水酸化ナトリ
ウム80g（2.0モル）を加え、さらに70℃において
３時間けん化反応を行う。反応終了後、反応生成
物中を減圧蒸留してエチルアルコールを除くこと
により、白色固体として、Ｎ―（２―ヒドロキシ
エチル）―Ｎ―〔ジ―（２―カルボキシエチル）
アミノエチル〕ウンデカンカルボン酸アミドのジ
ナトリウム塩473gが得られる。このものは薄層
クロマトグラフイーの結果、１個のスポツトを示
すことから単品であることが確認された。炭水素
分析の結果は、炭素55.62％（理論値55.67％）、
水素は8.39％（理論値8.50％）であつた。またケ
ルダール法による窒素分析の結果は5.78％（理論
値5.90％）であつた。
参考例 ２
ヤシ油脂肪酸（平均分子量200、AV280）から
製造された１―ヒドロキシエチル―２―アルキル
イミダゾリン268g（1.0モル）とアクリル酸エチ
ル200g（2.0モル）を、参考例１と同じフラスコ
中に入れ、25〜30℃で30分間かきまぜる。次いで
水36g（2.0モル）を添加すると発熱して70℃まで
昇温する。この温度で２時間反応したのち、水
539gを加え、さらに50％水酸化ナトリウム水溶
液16g（2.0モル）を加え、70℃で２時間加熱して
けん化させる。反応混合物を減圧蒸留し、蒸発残
分39.4％を得た。このようにしてPH12.6を示すＮ
―（２―ヒドロキシエチル）―Ｎ―〔ジ―（２―
カルボキシエチル）アミノエチル〕ヤシ油脂肪酸
アミドのジナトリウム塩を得た。このものは、未
反応アミン及びアクリル酸ナトリウムをそれぞれ
0.2重量％、0.1重量％含んでいた。
参考例 ３
アクリル酸エチルの量を150g（1.5モル）けん
化反応時に加える水の量を494g、50％水酸化ナ
トリウム水溶液の量を120g（1.5モル）にする以
外は、参考例２と同じ条件で実験を繰り返すこと
により、蒸発残分40重量％としてPH12.9の反応生
成分を得た。このものはＮ―（２―ヒドロキシエ
チル）―Ｎ―〔ジ―（２―カルボキシエチル）ア
ミノエチル〕ヤシ油脂肪酸アミドのジナトリウム
塩40重量％とＮ―（２―ヒドロキシエチル）―Ｎ
―（２―カルボキシエチルアミノエチル）ヤシ油
脂肪酸アミドのナトリウム塩60重量％からなる混
合物で未反応アミンとアクリル酸ナトリウムをそ
れぞれ0.3重量％ずつ含んでいた。
参考例 ４
原料イミダゾリン誘導体として、１―ヒドロキ
シエチル―２―ヘプタデシルイミダゾリン352g
（1.0モル）を用い、他は参考例２と全く同様に処
理してＮ―（２―ヒドロキシエチル）―Ｎ―〔ジ
―（２―カルボキシエチル）アミノエチル〕ステ
アリン酸アミドのジナトリウム塩の水溶液を得
た。このもののPHは12.5で蒸発残分は43.3重量％
であり、不純物として未反応アミン0.2重量％と
アクリル酸ナトリウム0.1重量％を含んでいた。
参考例 ５
１―ヒドロキシ―２―ウンデシルイミダゾリン
268g（1.0モル）及びアクリル酸メチル172g（2.0
モル）を用い、他の条件は参考例２と全く同様に
して実験を繰り返し、Ｎ―（２―ヒドロキシエチ
ル）―Ｎ―〔ジ―（２―カルボキシエチル）アミ
ノエチル〕ウンデカンカルボン酸アミドのジナト
リウム塩を得た。このもののPHは12.5であり蒸発
残分は40.3重量％で、未反応アミン0.2重量％、
アクリル酸ナトリウム0.1重量％を含んでいた。
参考例 ６
米国特許第3941817号明細書の方法に従い、か
きまぜ機、温度計、窒素吹込管及び真空ポンプに
接続した冷却管を備えた１容の四つ口フラスコ
中に、ヤシ油脂肪酸メチルエステル（平均分子量
200、AV280）214g（1.0モル）とアミノエチルエ
タノールアミン107g（1.03モル）及び25％ナトリ
ウムメトキシジメチルアルコール溶液を装入し、
窒素圧150mmHg以下で徐々に加熱し、100〜105℃
で31gのメチルアルコールを回収した。この残留
分として、Ｎ―ヤシ油アシル―Ｎ―ヒドロキシエ
チルエチレンジアミン286gを得た。
次いで窒素吹込管を滴下漏斗に代え、水375g
を加え、さらにモノクロル酢酸94.5g（1.0モル）
を加え、45℃まで冷却した。次に50重量％の水酸
化ナトリウム水溶液160g（2.0モル）を外温が55
℃を超えないように注意しながら、10分間にわた
つて添加した。添加完了後50〜60℃で３時間反応
させ、次いで80〜90℃で２時間反応させた。この
ようにして、Ｎ―（２―ヒドロキシエチル）―Ｎ
―（２―カルボキシメチル）アミノエチルヤシ油
脂肪族酸アミドのナトリウム塩を得た。
比較例
参考例１で得た化合物（試料Ａ）、参考例２で
得た化合物（試料Ｂ）及び参考例６得た化合物
（試料Ｃ）をそれぞれ８重量％の水溶液とし、そ
の0.1mlを１群３羽の白色家兎の雄に施こし、ド
レイズ法による眼刺激性試験を行つた。その結果
を第１表に示す。
The present invention relates to a hair wash that is less irritating to the skin, eyes, mucous membranes, etc. More specifically, the present invention relates to the general formula (In the formula, R is an aliphatic hydrocarbon group having 7 to 17 carbon atoms, and M is a hydrogen atom or an alkali metal atom.) It relates to irritating hair washes. Until now, substituted amidoamine type amphoteric surfactants have the general formula: (R′ in the formula is a long-chain aliphatic hydrocarbon residue,
M'' is a hydrogen atom or an alkali metal atom) is known (U.S. Patent No.
3262951 and 3941817). Such amphoteric surfactants are used as detergents, fiber treatment agents, antistatic agents, cosmetic bases, and the like. By the way, when a surfactant is used as a detergent ingredient in a hair wash such as a shampoo or conditioner, it is required to have no or little irritation to the skin, eyes, mucous membranes, etc. Substituted amidoamine type amphoteric surfactants cannot be said to be fully satisfactory in this respect and are therefore unsuitable for use in hair washes. As a result of intensive research to develop a hair wash that is less irritating to the skin, eyes, and mucous membranes, the present inventors found that by using a disubstituted aliphatic carboxylic acid amidoamine represented by the general formula () as a detergent component, Discovering that it is possible to achieve that purpose,
Based on this knowledge, the present invention was accomplished. Examples of the compound of the present invention represented by the general formula () include N-(2-hydroxyethyl)-N
-[Di-(2-carboxyethyl)aminoethyl]octanoic acid amide, N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl]decanoic acid amide, N-(2-hydroxyethyl) ethyl)-N-[di-(2-carboxyethyl)aminoethyl]dodecanoic acid amide, N-(2
-Hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl]stearic acid amide, N-(2-hydroxyethyl)-N-[di-
(2-carboxyethyl)aminoethyl]lauric acid amide, N-(2-hydroxyethyl)-N
- [Di-(2-carboxyethyl)aminoethyl] coconut oil fatty acid amide and their sodium and potassium salts. These compounds may have, for example, the general formula It can be obtained by reacting an imidazoline derivative represented by (R in the formula has the same meaning as above) with an acrylic acid alkyl ester and water, and saponifying the product with an alkali hydroxide. Examples of imidazoline derivatives represented by the general formula () include alkyl groups such as octyl, nonyl, decyl, undecyl, dodecyl, pentadecyl, hexadecyl, and heptadecyl groups at the 2-position, and octenyl groups. 1-(2-hydroxyethyl)- substituted with an alkenyl group such as a decenyl group, a pentadecenyl group, etc.
Imidazolines can be given. Further, as the acrylic acid alkyl ester to be reacted with the imidazoline derivative, lower alkyl esters such as methyl acrylate and ethyl acrylate are preferable. This acrylic acid alkyl ester is 1.3 to 1 mole of imidazoline derivative.
Used in a proportion of 2.0 mol. If this amount is more than 2.0 mol, there will be a large amount of unreacted sodium acrylate in the final product, and if this amount is less than 1.3 mol, there will be more unreacted amine, resulting in a lower yield. The amount of water to be reacted simultaneously with this acrylic acid alkyl ester is selected to be at least 1 mol, preferably in the range of 2.0 to 3.0 mol, per 1 mol of imidazoline derivative. If this amount is less than 1.0 mol, the amount of secondary amine as a by-product will increase and the yield of the target product will decrease. The reaction between the imidazoline derivative, the acrylic acid alkyl ester, and water is preferably carried out at a temperature of room temperature to 100°C, preferably 60 to 80°C. The time required for the reaction is usually in the range of 30 minutes to 4 hours, but
Conversion rates of about 99% are often obtained in 60 minutes. This reaction can be carried out in the presence of an alkaline catalyst if desired, but a catalyst is not particularly required. The addition product thus obtained is directly subjected to the next saponification treatment with alkali hydroxide without being isolated. This saponification is carried out by adding alkali hydroxide in an amount approximately equimolar to the acrylic acid alkyl ester used to the above reaction product, and
This is done by heating to 100°C. The time required for saponification is usually about 2 hours at 70°C. When the reaction product thus obtained is distilled under reduced pressure to remove the low molecular weight components contained therein, the target compound or a reaction product mainly containing it remains as a white solid. When the white solid of the target compound thus obtained was subjected to thin layer chromatography, it showed one spot and was confirmed to be a pure product. Furthermore, it was confirmed by infrared absorption spectrum, nuclear magnetic resonance spectrum, elemental analysis, etc. that this product has the structure of the general formula (). These compounds are characterized by significantly lower irritation to the skin, eyes, and mucous membranes than conventional surfactants with similar structures. The hair wash of the present invention contains the compound represented by the above general formula () as a detergent component, and is prepared and used in the form of shampoo or hair rinse. The content of the above-mentioned compound in it is not particularly different from the concentration required for detergent ingredients normally used in conventional shampoos and hair rinses, and the concentration is at least 2% by weight for the purpose of use. be selected as appropriate. In addition to the detergent ingredients, the hair wash of the present invention may contain various additives commonly used in shampoos and hair rinses, such as preservatives, fragrances, and pigments, and may also cause irritation to the eyes and mucous membranes. Other surfactants can also be used in combination at concentrations within a range that does not cause. Next, the present invention will be explained in more detail with reference to Reference Examples and Examples. Reference Example 1 In a 2-volume four-necked flask equipped with a stirrer, condenser, and thermometer, add 1-hydroxyethyl-2.
- Charge 268 g (1.0 mol) of undecyl imidazoline and 200 g (2.0 mol) of ethyl acrylate,
After stirring for 30 minutes at ~35°C, 36g (2.0 moles) of water is added. At this time, heat is generated and the temperature rises to 70°C, so after reacting at this temperature for 2 hours, 400 ml of ethyl alcohol and 80 g (2.0 mol) of sodium hydroxide are added, and the saponification reaction is further carried out at 70°C for 3 hours. After the reaction is complete, the reaction product is distilled under reduced pressure to remove ethyl alcohol, resulting in N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)] as a white solid.
473 g of the disodium salt of aminoethyl undecanecarboxylic acid amide is obtained. As a result of thin layer chromatography, this product was confirmed to be a single product as it showed one spot. The result of hydrocarbon analysis is carbon 55.62% (theoretical value 55.67%),
Hydrogen was 8.39% (theoretical value 8.50%). Further, the result of nitrogen analysis using the Kjeldahl method was 5.78% (theoretical value 5.90%). Reference Example 2 268 g (1.0 mol) of 1-hydroxyethyl-2-alkylimidazoline produced from coconut oil fatty acid (average molecular weight 200, AV 280) and 200 g (2.0 mol) of ethyl acrylate were placed in the same flask as in Reference Example 1. Stir for 30 minutes at 25-30℃. Next, when 36 g (2.0 mol) of water is added, heat is generated and the temperature rises to 70°C. After reacting at this temperature for 2 hours, water
Add 539 g, and further add 16 g (2.0 mol) of a 50% aqueous sodium hydroxide solution, and saponify by heating at 70°C for 2 hours. The reaction mixture was distilled under reduced pressure to obtain an evaporation residue of 39.4%. In this way, N showing PH12.6
-(2-Hydroxyethyl)-N-[G-(2-
Carboxyethyl) aminoethyl] disodium salt of coconut oil fatty acid amide was obtained. This product contains unreacted amine and sodium acrylate, respectively.
It contained 0.2% by weight and 0.1% by weight. Reference Example 3 Same conditions as Reference Example 2 except that the amount of ethyl acrylate was 150 g (1.5 mol), the amount of water added during the saponification reaction was 494 g, and the amount of 50% aqueous sodium hydroxide solution was 120 g (1.5 mol). By repeating the experiment, a reaction product with a pH of 12.9 was obtained as an evaporation residue of 40% by weight. This product contains 40% by weight of disodium salt of N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl] coconut oil fatty acid amide and N-(2-hydroxyethyl)-N
-(2-Carboxyethylaminoethyl) A mixture consisting of 60% by weight of sodium salt of coconut oil fatty acid amide, containing 0.3% by weight each of unreacted amine and sodium acrylate. Reference example 4 352 g of 1-hydroxyethyl-2-heptadecyl imidazoline as a raw material imidazoline derivative
(1.0 mol) and treated in the same manner as in Reference Example 2 to prepare disodium salt of N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl]stearamide. An aqueous solution was obtained. The pH of this product is 12.5 and the evaporation residue is 43.3% by weight.
It contained 0.2% by weight of unreacted amine and 0.1% by weight of sodium acrylate as impurities. Reference example 5 1-hydroxy-2-undecylimidazoline
268g (1.0 mol) and 172g (2.0 mol) of methyl acrylate
The experiment was repeated using exactly the same conditions as in Reference Example 2, using N-(2-hydroxyethyl)-N-[di-(2-carboxyethyl)aminoethyl]undecanecarboxylic acid amide. The sodium salt was obtained. The pH of this product is 12.5, the evaporation residue is 40.3% by weight, unreacted amine is 0.2% by weight,
It contained 0.1% by weight of sodium acrylate. Reference Example 6 According to the method described in US Pat. No. 3,941,817, coconut oil fatty acid methyl ester ( average molecular weight
200, AV280) 214 g (1.0 mol) and aminoethylethanolamine 107 g (1.03 mol) and 25% sodium methoxy dimethyl alcohol solution were charged.
Gradually heat to 100-105℃ under nitrogen pressure of 150mmHg or less
31g of methyl alcohol was recovered. As the residue, 286 g of N-coconut acyl-N-hydroxyethylethylenediamine was obtained. Next, replace the nitrogen blowing pipe with a dropping funnel and add 375g of water.
and then 94.5g (1.0mol) of monochloroacetic acid.
was added and cooled to 45°C. Next, add 160 g (2.0 mol) of a 50% by weight aqueous sodium hydroxide solution to an external temperature of 55%.
The mixture was added over a period of 10 minutes, being careful not to exceed the temperature. After the addition was completed, the reaction was carried out at 50-60°C for 3 hours, and then at 80-90°C for 2 hours. In this way, N-(2-hydroxyethyl)-N
-(2-Carboxymethyl)aminoethyl coconut oil fatty acid amide sodium salt was obtained. Comparative Example The compound obtained in Reference Example 1 (Sample A), the compound obtained in Reference Example 2 (Sample B), and the compound obtained in Reference Example 6 (Sample C) were each made into an 8% by weight aqueous solution, and 0.1 ml of the solution was added to 1 An eye irritation test using the Draize method was conducted on three groups of male white rabbits. The results are shown in Table 1.
【表】
試料Ａ及びＢすなわち本発明で用いる化合物
は、角膜に全く障害を生じることがなく、また虹
彩充血もみられなかつた。結膜浮腫が少し認めら
れたが、特に問題になる程度ではなく、非常に眼
刺激性の低いことが分つた。
実施例 １
代表例としてＮ―（２―ヒドロキシエチル）―
Ｎ―〔ジ―（２―カルボキシエチル）―アミノエ
チル〕ヤシ油脂肪酸アミドのジナトリウム塩（試
料Ｂ）を用い、以下に示す組成により低刺激性シ
ヤンプーを調製した。
このものは眼刺激性はほとんど示さなかつた。
成 分 重量％
試料Ｂ 15
ヤシ油脂肪酸ジエタノールアミド ３
クエン酸―水塩 ２
ｐ―ヒドロキシ安息香酸エチル 0.5
保存剤、香料、色素 適 量
脱イオン水 バランス
実施例 ２
実施例１と同じ化合物を用い、以下に示す組成
物により乳液状ヘアーリンスを調製した。
成 分 重量％
試料Ｂ ２
ジステアリルジメチルアンモニウムクロリド ３
エチレングリコールモノステアレート １
ポリオキシエチレンオレイルアルコール １
グリセリン ５
香料、色素 適 量
脱イオン水 バランス
このものは眼刺激性をほとんど示さず、洗髪し
た毛髪に対して、くし通りをよくする効果が認め
られた。
実施例 ３
実施例１と同じ化合物を用い、以下に示す組成
物により液体洗髪剤を調製した。
成 分 重量％
試料Ｂ 18
ラウリン酸ジエタノールアミド ５
クエン酸―水塩 １
香料、色素 適 量
脱イオン水 バランス
このものは眼刺激性を示さないものであつた。[Table] Samples A and B, that is, the compounds used in the present invention, did not cause any damage to the cornea, and no iris hyperemia was observed. Although a small amount of conjunctival edema was observed, it was not of a particular degree of concern, and it was found that the eye irritation was extremely low. Example 1 As a representative example, N-(2-hydroxyethyl)-
A hypoallergenic shampoo was prepared using the disodium salt of N-[di-(2-carboxyethyl)-aminoethyl] coconut oil fatty acid amide (sample B) with the composition shown below. This product showed almost no eye irritation. Ingredient weight% Sample B 15 Coconut oil fatty acid diethanolamide 3 Citric acid hydrate 2 Ethyl p-hydroxybenzoate 0.5 Preservatives, fragrances, pigments Appropriate amount of deionized water Balance Example 2 Using the same compound as Example 1, A milky hair rinse was prepared using the composition shown below. Ingredient weight % Sample B 2 Distearyldimethylammonium chloride 3 Ethylene glycol monostearate 1 Polyoxyethylene oleyl alcohol 1 Glycerin 5 Fragrance, pigment Appropriate amount Deionized water Balance This product shows almost no eye irritation, and washes hair. However, the effect of improving combability was observed. Example 3 Using the same compounds as in Example 1, a liquid hair wash was prepared with the composition shown below. Ingredient weight % Sample B 18 Lauric acid diethanolamide 5 Citric acid hydrate 1 Flavor, pigment Appropriate amount of deionized water Balance This product did not cause eye irritation.
Claims (1)
化水素基、Ｍは水素原子又はアルカリ金属原子で
ある） で表わされるジ置換脂肪族カルボン酸アミドアミ
ンを洗剤成分として含有することを特徴とする低
刺激性洗髪剤。[Claims] 1. General formula (In the formula, R is an aliphatic hydrocarbon group having 7 to 17 carbon atoms, and M is a hydrogen atom or an alkali metal atom.) It is characterized by containing a disubstituted aliphatic carboxylic acid amidoamine represented by the following as a detergent component. Hypoallergenic hair wash.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15117284A JPS6034904A (en) | 1984-07-23 | 1984-07-23 | Hair wash having low irritation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15117284A JPS6034904A (en) | 1984-07-23 | 1984-07-23 | Hair wash having low irritation |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14435676A Division JPS5368721A (en) | 1976-12-01 | 1976-12-01 | Disubstd. aliphatic carboxylic acid amide amines, and detergents and cosmeticcompositions containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6034904A JPS6034904A (en) | 1985-02-22 |
| JPS6151561B2 true JPS6151561B2 (en) | 1986-11-10 |
Family
ID=15512884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15117284A Granted JPS6034904A (en) | 1984-07-23 | 1984-07-23 | Hair wash having low irritation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6034904A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63193286A (en) * | 1987-01-28 | 1988-08-10 | シンボル テクノロジイズ インコーポレイテッド | Bar code sign reader with both or either of spot dimensions and working distance made variable |
| JPH01133659U (en) * | 1988-03-02 | 1989-09-12 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993918A (en) * | 1956-04-02 | 1961-07-25 | John J Mccabe Jr | Novel compositions of matter and methods for preparing them |
| JPS5265141A (en) * | 1975-11-25 | 1977-05-30 | Kao Corp | Corrosion inhibitor for metals |
-
1984
- 1984-07-23 JP JP15117284A patent/JPS6034904A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993918A (en) * | 1956-04-02 | 1961-07-25 | John J Mccabe Jr | Novel compositions of matter and methods for preparing them |
| JPS5265141A (en) * | 1975-11-25 | 1977-05-30 | Kao Corp | Corrosion inhibitor for metals |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63193286A (en) * | 1987-01-28 | 1988-08-10 | シンボル テクノロジイズ インコーポレイテッド | Bar code sign reader with both or either of spot dimensions and working distance made variable |
| JPH01133659U (en) * | 1988-03-02 | 1989-09-12 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6034904A (en) | 1985-02-22 |
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