JPH0524127B2 - - Google Patents
Info
- Publication number
- JPH0524127B2 JPH0524127B2 JP58195107A JP19510783A JPH0524127B2 JP H0524127 B2 JPH0524127 B2 JP H0524127B2 JP 58195107 A JP58195107 A JP 58195107A JP 19510783 A JP19510783 A JP 19510783A JP H0524127 B2 JPH0524127 B2 JP H0524127B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- hair
- shampoo
- alkyl
- polyglycol ether
- 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 - Lifetime
Links
- 239000002453 shampoo Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- -1 Olefin Sulfonate Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 229920000151 polyglycol Polymers 0.000 claims description 8
- 239000010695 polyglycol Substances 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 150000003944 halohydrins Chemical class 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims description 3
- 229920000233 poly(alkylene oxides) Chemical group 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 230000003750 conditioning effect Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010019049 Hair texture abnormal Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001792 White test Methods 0.000 description 2
- 229920006317 cationic polymer Polymers 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 1
- 150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- VYIGXNQKBVNZHX-UHFFFAOYSA-N S(=O)(=O)(OOC=C)OOC=C.C(CCCCCCCCCCC)OCCCCCCCCCCCC Chemical compound S(=O)(=O)(OOC=C)OOC=C.C(CCCCCCCCCCC)OCCCCCCCCCCCC VYIGXNQKBVNZHX-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical class [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003788 bath preparation Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000003766 combability Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000003648 hair appearance Effects 0.000 description 1
- 150000002402 hexoses Chemical group 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002851 polycationic polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000009145 protein modification Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/594—Mixtures of polymers
Description
本発明は整髪用シヤンプーおよび洗身用整剤に
関するものである。
シヤンプー、シヤワーおよび合成のアニオン性
界面活性剤をベースとする浴用製剤で以洗髪した
後では、毛髪はしばしば美容的に不満足な状態に
ある。濡れているときには、髪すきが困難であ
り、鈍い感じである。乾かしたあとは、洗い髪は
静電気をおびる傾向があり、その結果、洗いたて
の髪がよく知られている「ひらひら状態」がおこ
る。その上、洗いたての髪はしばしばつやのない
外観をもつ。これらの理由のために、洗髪または
シヤンプー使用後に、調整用製剤を髪に付与する
ことが知られている。これらの場合における製剤
はたいていの場合、カチオン活性界面活性剤を含
むリンス液またはクリーム様ローシヨンである。
ある種の物質を通常のシヤンプーへ添加して洗髪
時にある調整効果を得ることも知られている。こ
の種のタイプの物質は例えば、水溶性プロテイン
またはプロテイン変性生成物、ポリカチオン性ポ
リマー、例えば、DE−OSNo.21 50 899に記載の
種類のアミノポリカルバミド樹脂、US−PSNo.
3816616に記載の種類のポリカチオン性セルロー
ズ誘導体、あるいはUS−PSNo.4292212に記載の
種類のポリカチオン性グア誘導体、を含む。カチ
オン性または四級アンモニウム基を含む多くの他
の水溶性ポリマーがこの目的のために提唱されて
きた。
既知の毛髪調整用添加物のすべてに共通する一
つの欠点は、アニオン性の洗髪用製剤の中で使用
するときに少くとも一部それらの効果が減殺され
ることにある。特に強い効果をもつ製品はしばし
ば髪への過度の吸着を示し、その結果、乾いた髪
の弾性、腰、および恰好を損なう。
従つて、本発明の目的は、適当な毛髪回復用添
加剤の存在によつて、濡れているときに髪を容易
にすることができそしてまた乾いた髪を特に弾
性、腰、つやおよび恰好を含めた満足できる美容
的性質をもつたままにする、周知のきわめて泡立
ちのよいアニオン性の洗滌用活性物質をベースと
するシヤンプー調合物を提供することである。
アニオン性洗滌用活性物質をベースとするシヤ
ンプーの毛髪保護性質はポリカチオン性グア誘導
体、硬化可能のカチオン性重縮合生成物、親水性
脂肪酸エステルおよび水溶性ポリビニルピロリド
ンの組合せ物をシヤンプーへ添加することによつ
て特に効果的に改善し得ることが、ここに発見さ
れたのである。従つて、本発明は、アニオン性洗
滌用活性物質;と
0.1から4重量%の3−(トリメチルアミノ)−
2−ヒドロキシプロピルグア塩化物、
0.5から5重量%の、反応性アミオ基およびポ
リアルキレンオキサイド基を含む水溶性ポリアミ
ンとエピクロロヒドリンまたは分子中に一つより
多くのエポキサイド基および/またはハロヒドリ
ン基を含む化合物との易水溶性で硬化可能な重縮
合生成物、
1から4重量%の、グリセリンと4から20モル
のエチレンオキサイドとのエチレンオキサイド付
加物と1から2モルのC8−C18脂肪酸とのエステ
ル化生成物、
0.1から1重量%の、平均分子量が少くとも
10000であるポリビニルピロリドン、
を含むことを特徴とする標準的セツトアツプ剤;
との水溶液をベースとする毛髪調整用シヤンプー
に関するものである。
3−(トリメチルアミノ)−2−ヒドロキシプロ
ピルグア塩化物はUS−PSNo.3589978から知られ
るカチオン性グア誘導体である。そこに記載され
ている生成物は基本単位として、一つのグルコシ
ド結合によつて結合した2個のマンノース単位と
このマンノース単位のヒドロキシル基の一つへ結
合した1個のガラクトース単位を含んでいる。平
均的には、ヘキソーズ環の各々は3個の遊離のヒ
ドロキシル基を担持している。これらの遊離ヒド
ロキシル基は反応性四級アンモニウム化合物と反
応してカチオン性ポリマーを与える。本発明に従
うシヤンプー中に使用するカチオン性ポリマーは
「コスメデイア(R)−グアC261」の名称で商業的に
入手できる。
反応性アミノ基とポリアルキレンオキサイド基
を含む水溶性ポリアミンとエピクロロヒドリンま
たは分子中に一つより多くのエポキサイドおよ
び/またはハロヒドリン基を含む化合物との易水
溶性の硬化可能重縮合生成物はDE−PSNo.
2363871から知られる。そこに記載されているカ
チオン性重縮合生成物のうち、上述特許の生成物
Fとして生成される重縮合物は本発明による毛髪
調整用シヤンプーの製造において特に好適であ
る。このタイプの一つの製品は例えばポリクオー
トH(R)の名称で商業的に入手できる。
グリコールと4から20モルのエチレンオキサイ
ドとのエチレンオキサイド付加物と1から2モル
のC8−C18脂肪酸とのエステル化生成物はDE−
ASNo.20 24 051から知られる。その中で記述され
ているエステル化生成物のうち、7.4モルのエチ
レンオキサイドと1モルのグリセリンとの付加と
それに続くこの付加物1モルとC8−C18ココナツ
ツ油脂肪酸1モルとのエステル化によつて得られ
る部分エステルは、本発明による毛髪調整用シヤ
ンプーの中での使用に特に適している。この組成
を有する製品は例えばセチオールHE(R)の名称で
商業的に入手できる。
平均分子量が10000から70000の範囲にあるポリ
ビニルピロリドンは例えばコリドン(R)およびルビ
スコール(R)の名称で商業的に入手できる。
K−値が約30に相当する、平均分子量が約
40000のポリビニルピロリドンは本発明による毛
髪調整用シヤンプーの製造に特に好適である。
最終的シヤンプー中の本質的調整剤の上記混合
物の濃度は重量で1.7−14%の範囲であつてよく、
2−8重量%の範囲が好ましい。
上述の各種の本質的調整剤の比は変動があつて
よい。一般的には、この比はグア誘導体約1部対
ポリクオート(R)H0.5−4部対セチオール(R)HE0.5
−4部対PVP0.15−0.5部である。
本発明による毛髪調整用シヤンプーは好ましく
は、水溶性アニオン性の洗滌活性物質として、ア
ルキル基中に8から18個好ましくは12から16個の
炭素原子を含むアルキル硫酸半エステルのアルカ
リ金属、マグネシウム、アンモニウムおよび/ま
たはC2−C3アルカノールアンモニウムの塩、あ
るいは、アルキル基中に8から18個好ましくは12
から16個の炭素原子と分子中に1から6個のグリ
コールエーテル基を含むアルキルポリグリコール
エーテル硫酸半エステル、を含む。その他の好適
であるアニオン性洗滌活性物質は、10から18個の
炭素原子を含む一級および二級線状アルカンスル
ホン酸塩、10から18個の炭素原子を含むオレフイ
ンのスルホン化において得られる種類のアルケン
スルホン酸塩およびヒドロキシアルカンスルホン
酸塩、C8−C18脂肪酸アルキロールアミドポリグ
リコールエーテル硫酸塩、C8−C18脂肪酸モノグ
リセライド硫酸塩、アルキル基中に8から18個の
炭素原子を含むスルホン琥珀酸モノアルキルエス
テルあるいはアルキル基中に6から10個の炭素原
子を含むジアルキルエステル、アルキル基中に8
から18個の炭素原子を含みかつ分子中に2から6
個のポリグリコールエーテル基を含むアルキルポ
リグリコールエーテルカルボン酸塩、および、ア
シル基中に8から18個の炭素原子を含むアシルサ
ルコシン、アシルタウライドおよびアシルイセチ
オネート、である。
一般的には、シヤンプー中のアニオン性界面活
性剤の濃度は約5から約50重量%の範囲にあつて
もよく、好ましい範囲は約8から約30重量%であ
る。
好ましいアニオン性界面活性剤はナトリウムラ
ウリルポリグリコールエーテル硫酸塩と脂肪酸ア
ルコール硫酸塩との重量で約2:1から1:1の
比の混合物から成る。脂肪酸アルコール硫酸塩は
好ましくは約10−14個の炭素原子、好ましくは12
−14個の炭素原子をもつアルコール成分を含んで
いる。存在するアニオン性界面活性剤の合計量と
本質的調整剤の混合物との比は約10:1から1:
1、好ましくは2.5:1から1.5:1の範囲にあつ
てよい。
さらに、本発明による毛髪調整用シヤプーは、
C8−C18脂肪酸アルキロールアミド型の増粘剤の
ような標準的添加剤およびセツトアツプ剤、例え
ばエチレングリコールジエステル型の不透明剤、
アルカリまたはアンモニウムの燐酸塩またはクエ
ン酸塩のようなPH安定剤、ホルムアルデヒドまた
はp−ヒドロキシ安息香酸エステルのような保存
剤、染料、芳香付与剤、およびふけ止め剤または
セイボスタチツクス(sebostatice)のような既
知の毛髪美容活性物質、を含んでよい。
本発明による組成物をもつ毛髪調整用シヤンプ
ーはそれらで以て洗つた髪の毛髪調整的性質にお
ける予想外の顕著な改善によつて区別される。例
えば、本発明による毛髪調整用シヤンプンーのい
わゆる濡れ時の髪すき性(wet combability)は
調整用成分のうち一つだけ例えばコスメデイアグ
ア(R)C261のみを含むシヤンプーと相対的にかなり
改善される。このことはその他の本質的諸成分が
濡れ時の髪すき性に自らはほとんどまたは全く影
響をもたないのでより一層驚くべきことである。
類似の驚くべき相乗的効果は各種要素、すなわ
ち、つや、触感、および帯電防止性、いわゆる
「調整効果(conditioning effect)」、を検討すれ
ば観察することができる。
乾いた毛髪の触感(弾性)とつやは本発明によ
るシヤンプーにより、本発明による場合に必要と
される諸成分の例えば一つだけを含む慣用的シヤ
ンプーの場合よりも大きい程度に改善される。最
後に、髪が乾いた後に静電気を発現する傾向は本
発明による調整用シヤンプーを使用することによ
つて相当に軽減される毛髪はひらひらする傾向が
減り、より容易にすくことができ、その形状はよ
り長く保たれる。
本発明による毛髪調整用シヤンプーで以て得ら
れる毛髪美容効果は以下の実施例において慣用シ
ヤンプーと比較することによつて示される。
実施例
本発明によるシヤンプー調合物(No.1からNo.
3)は本発明によるシヤンプー必要諸成分を全く
含まない(No.10)かあるいは一部のみを含む(No.
4からNo.9)類似のシヤンプー調合物と一緒に比
較の目的で試験した。
性能−試験シヤンプー調合物を第1表に示す。
実施例 1
濡れ時の髪すき性の測定(実験室試験)
濡れ時の髪すき性を髪すき抵抗、すなわち櫛を
毛髪の房の中で引くのに必要な力、を測定するこ
とによつて決定した。修正した抗張試験機
(Zwick Company of Einsingen u¨ber Ulm/
Danubeが製造するようなタイプ1402)を使用し
た。試験装置は“Riechstoffe、Aromen、
Kosmetika、No.12/1977”325頁、第2および3
欄において記載されている。
一定条件下での漂白とパーマネントウエーブに
よつて予め損傷を与えた標準化した髪房を使用し
た。これらの房を手の温かさの水の中で第1表に
示すシヤンプーで以て洗い、澄明水で以てすすい
だ。
誤差を最小にするために、髪すき抵抗は被検シ
ヤンプーの各々について15回測定し、平均値を計
算した。平均の髪すき抵抗値は白試験値の%で記
されている。白試験値は10重量%のナトリウムラ
ウリルエーテルジエテノキシ硫酸塩を含む水溶液
によるシヤンプー洗いと澄明水によるすすぎの後
に測定した。
TECHNICAL FIELD The present invention relates to shampoos for hair styling and preparations for washing the body. After washing with shampoos, showers and bath preparations based on synthetic anionic surfactants, the hair is often in a cosmetically unsatisfactory condition. When wet, combing the hair is difficult and feels dull. After drying, washed hair tends to pick up static electricity, resulting in the well-known "flutter" of freshly washed hair. Moreover, freshly washed hair often has a lackluster appearance. For these reasons, it is known to apply conditioning formulations to the hair after washing or shampooing. The formulation in these cases is most often a rinse or cream-like lotion containing a cationically active surfactant.
It is also known to add certain substances to conventional shampoos to obtain certain conditioning effects during hair washing. Substances of this type are, for example, water-soluble proteins or protein modification products, polycationic polymers, such as aminopolycarbamide resins of the type described in DE-OS No. 21 50 899, US-PS No.
3816616, or polycationic guar derivatives of the type described in US-PS No. 4292212. Many other water-soluble polymers containing cationic or quaternary ammonium groups have been proposed for this purpose. One drawback common to all known hair conditioning additives is that their effectiveness is at least partially diminished when used in anionic hair washing formulations. Products with particularly strong effects often exhibit excessive adsorption to the hair, thus impairing the elasticity, elasticity and shape of dry hair. It is therefore an object of the present invention to make it possible, by the presence of suitable hair restoration additives, to make the hair easier when wet and also to improve the dry hair in particular its elasticity, elasticity, shine and appearance. The object of the present invention is to provide shampoo formulations based on known highly lathering anionic cleansing actives which retain satisfactory cosmetic properties including: The hair-protecting properties of shampoos based on anionic cleansing active substances are achieved by adding to the shampoo a combination of polycationic guar derivatives, curable cationic polycondensation products, hydrophilic fatty acid esters and water-soluble polyvinylpyrrolidone. It has now been discovered that improvements can be made particularly effectively by Accordingly, the present invention provides an anionic detersive active substance; and from 0.1 to 4% by weight of 3-(trimethylamino)-
2-hydroxypropyl guachloride, 0.5 to 5% by weight of a water-soluble polyamine containing reactive amio groups and polyalkylene oxide groups and epichlorohydrin or more than one epoxide group and/or halohydrin group in the molecule 1 to 4% by weight of ethylene oxide adducts of glycerin and 4 to 20 mol of ethylene oxide and 1 to 2 mol of C 8 -C 18 esterification products with fatty acids, from 0.1 to 1% by weight, with an average molecular weight of at least
10,000 polyvinylpyrrolidone;
This invention relates to a hair conditioning shampoo based on an aqueous solution of. 3-(Trimethylamino)-2-hydroxypropyl guar chloride is a cationic guar derivative known from US-PS No. 3589978. The products described there contain as basic units two mannose units linked by one glucosidic bond and one galactose unit linked to one of the hydroxyl groups of this mannose unit. On average, each hexose ring carries three free hydroxyl groups. These free hydroxyl groups react with reactive quaternary ammonium compounds to give cationic polymers. The cationic polymer used in the shampoo according to the invention is commercially available under the name " Cosmedea® -Guar C261". Readily water-soluble curable polycondensation products of water-soluble polyamines containing reactive amino groups and polyalkylene oxide groups with epichlorohydrin or compounds containing more than one epoxide and/or halohydrin group in the molecule are DE−PSNo.
Known from 2363871. Among the cationic polycondensation products described therein, the polycondensation product produced as product F of the above-mentioned patent is particularly suitable for the production of the hair conditioning shampoo according to the invention. One product of this type is commercially available, for example under the name Polyquat H (R) . Esterification products of ethylene oxide adducts of glycols with 4 to 20 moles of ethylene oxide and 1 to 2 moles of C8 - C18 fatty acids are DE-
Known from ASNo.20 24 051. Among the esterification products described therein, the addition of 7.4 mol of ethylene oxide with 1 mol of glycerin followed by the esterification of 1 mol of this adduct with 1 mol of C 8 -C 18 coconut oil fatty acid The partial esters obtained by are particularly suitable for use in hair conditioning shampoos according to the invention. Products with this composition are commercially available, for example under the name Cetiol HE (R) . Polyvinylpyrrolidones with average molecular weights in the range 10,000 to 70,000 are commercially available, for example under the names Kollidon (R) and Rubiscoll (R) . The average molecular weight is approximately 30, corresponding to a K-value of approximately 30.
40,000 polyvinylpyrrolidone is particularly suitable for producing the hair conditioning shampoo according to the invention. The concentration of said mixture of essential modifiers in the final shampoo may range from 1.7-14% by weight;
A range of 2-8% by weight is preferred. The ratios of the various essential modifiers mentioned above may vary. Generally, this ratio is approximately 1 part guar derivative to 0.5-4 parts Polyquat (R) H to 0.5 parts Cetiol (R) HE.
-4 parts vs. 0.15-0.5 parts of PVP. The hair conditioning shampoo according to the invention preferably comprises, as water-soluble anionic cleansing active substances, alkali metals, magnesium, alkyl sulfate half-esters containing 8 to 18, preferably 12 to 16 carbon atoms in the alkyl group; Ammonium and/or C 2 -C 3 alkanol ammonium salts or 8 to 18, preferably 12
Alkyl polyglycol ether sulfate half esters containing from 16 carbon atoms and from 1 to 6 glycol ether groups in the molecule. Other suitable anionic detersive actives are primary and secondary linear alkanesulfonates containing 10 to 18 carbon atoms, of the type obtained in the sulfonation of olefins containing 10 to 18 carbon atoms. Alkenesulfonates and hydroxyalkanesulfonates, C8 - C18 fatty acid alkylolamide polyglycol ether sulfates, C8 - C18 fatty acid monoglycerides sulfates, sulfones containing 8 to 18 carbon atoms in the alkyl group Succinic acid monoalkyl ester or dialkyl ester containing 6 to 10 carbon atoms in the alkyl group, 8 to 10 carbon atoms in the alkyl group
containing 18 carbon atoms and 2 to 6 carbon atoms in the molecule
and acyl sarcosines, acyl taurides and acyl isethionates containing from 8 to 18 carbon atoms in the acyl group. Generally, the concentration of anionic surfactant in the shampoo may range from about 5 to about 50% by weight, with a preferred range of about 8 to about 30% by weight. A preferred anionic surfactant comprises a mixture of sodium lauryl polyglycol ether sulfate and fatty alcohol sulfate in a ratio of about 2:1 to 1:1 by weight. The fatty acid alcohol sulfate preferably has about 10-14 carbon atoms, preferably 12
- Contains an alcohol component with 14 carbon atoms. The ratio of the total amount of anionic surfactant present to the mixture of essential modifiers is about 10:1 to 1:
1, preferably in the range of 2.5:1 to 1.5:1. Furthermore, the hair conditioning shampoo according to the present invention includes:
Standard additives and setting agents such as thickeners of the C8 - C18 fatty acid alkylolamide type, e.g. opacifiers of the ethylene glycol diester type,
PH stabilizers such as alkali or ammonium phosphates or citrates, preservatives such as formaldehyde or p-hydroxybenzoic acid esters, dyes, fragrances, and antidandruff agents or sebostatices. may include known hair cosmetic actives, such as. Hair conditioning shampoos with the compositions according to the invention are distinguished by an unexpectedly significant improvement in the conditioning properties of hair washed with them. For example, the so-called wet combability of the shampoo for hair conditioning according to the present invention is considerably improved compared to a shampoo containing only one of the conditioning ingredients, such as Cosmediagua (R) C261. . This is all the more surprising since the other essential ingredients have little or no effect on wet hair combing properties.
A similar surprising synergistic effect can be observed when considering various factors: gloss, feel, and antistatic properties, the so-called "conditioning effect." The feel (elasticity) and shine of dry hair are improved by the shampoo according to the invention to a greater extent than with conventional shampoos which contain, for example, only one of the ingredients required in the case according to the invention. Finally, the tendency of the hair to develop static electricity after drying is considerably reduced by using the conditioning shampoo according to the invention; the hair has a reduced tendency to flutter, can be combed more easily, and its shape is kept longer. The hair cosmetic effects obtained with the hair conditioning shampoo according to the invention are demonstrated in the following examples by comparison with conventional shampoos. Examples Shampoo formulations according to the invention (No. 1 to No.
3) does not contain any necessary ingredients for the shampoo according to the present invention (No. 10) or contains only some of them (No. 3).
No. 4 to No. 9) were tested together with similar shampoo formulations for comparative purposes. Performance-Test Shampoo formulations are shown in Table 1. Example 1 Measurement of hair combing ability when wet (laboratory test) Hair combing ability when wet is measured by measuring hair combing resistance, that is, the force required to pull a comb through a lock of hair. Decided. Modified tensile testing machine (Zwick Company of Einsingen u¨ber Ulm/
Type 1402) as manufactured by Danube was used. The test equipment was “Riechstoffe, Aromen,
Kosmetika, No. 12/1977” 325 pages, 2nd and 3rd
It is described in the column. Standardized hair tresses were used that had been previously damaged by bleaching and permanent waving under constant conditions. The tresses were washed in hand-warm water with the shampoo shown in Table 1 and rinsed with clear water. To minimize errors, hair combing resistance was measured 15 times for each shampoo tested and the average value calculated. The average hair combing resistance value is expressed as a percentage of the white test value. White test values were determined after shampooing with an aqueous solution containing 10% by weight of sodium lauryl ether diethenoxy sulfate and rinsing with clear water.
【表】【table】
【表】
実施例 2
毛髪美容的性質の試験(美容院試験)
毛髪美容的性質の試験の評価をいわゆる片側
(halfside)試験を使用して髪の質が相互に異な
る10人の実験対象者について実施した。試験は訓
練された美容師によつて実施された。片側試験は
二つの毛髪処理用製剤の、あるいは一つの毛髪処
理用製剤と一つの標準品との、比較試験を実験対
象者について用いた。これらの試験において、本
発明によるヘアーシヤンプーNo.1を標準として使
用した。第2表に示し比較点数はヘアーシヤンプ
ーNo.4からNo.10がシヤンプーNo.1の評価から異な
つている程度についての一つの尺度である。
手順と評価
実験対象者の毛髪を濡らし、真中で分けた。標
準シヤンプーを試験対象者5人の頭の左半分へ付
与し、比較用シヤンプーを右側半分へ各々の場合
(洗滌前)に5gの等しい量で付与した。他の5
人の実験対象者の場合には、彼らの頭の他の半分
は同じ製品で以て処理した。両側を同じようにし
てシヤンプーで洗い水ですすいだ。この主洗いに
は、シヤンプーをもう一度2.5gの量で頭の同じ
側へ付与し、すり込んで泡を形成させそして完全
に澄明水ですすぎ出した。
洗滌中および洗滌後において、次の第2表に示
した規準を別々に二つの側の各々について美容師
によつて評価した。評価は点数(1=∧優秀、2=∧
良、3=∧可、4=∧不良)を与えることによつて
実施した。10人の実験対象者について与えられた
点数から、平均値を同じ製品について計算した。
標準生成物の平均値を比較用製品についての平均
値から差引いた。10人の実験対象者についての評
価の平均値においてこのようにして得られた対の
差を下の第2表に示す。
結果:比較用シヤンプーはすべて標準シヤンプー
(本発明によるシヤンプーNo.1)よりその毛髪
美容的性質において劣つていると判断された。[Table] Example 2 Test for hair cosmetic properties (hair salon test) The so-called half-side test was used to evaluate the test for hair cosmetic properties on 10 experimental subjects with mutually different hair qualities. carried out. The test was conducted by a trained cosmetologist. One-sided tests were used to compare two hair treatment formulations, or one hair treatment formulation and one standard product, on experimental subjects. In these tests, hair shampoo No. 1 according to the invention was used as standard. The comparison scores shown in Table 2 are a measure of the degree to which hair shampoos No. 4 to No. 10 differ from the evaluation of shampoo No. 1. Procedure and Evaluation The hair of the experimental subjects was wetted and parted down the middle. The standard shampoo was applied to the left half of the head of the five test subjects and the comparison shampoo was applied to the right half in equal amounts of 5 g in each case (before washing). other 5
In the case of human test subjects, the other half of their heads were treated with the same product. Wash both sides in the same way with shampoo and rinse with water. For this main wash, Shampoo was again applied in an amount of 2.5 g to the same side of the head, rubbed in to form a lather and rinsed out thoroughly with clear water. During and after washing, the criteria listed in Table 2 below were evaluated by the beautician on each of the two sides separately. Evaluation is based on points (1 = ∧ excellent, 2 = ∧
Good, 3=∧fair, 4=∧bad). From the scores given for the 10 experimental subjects, an average value was calculated for the same product.
The average value for the standard product was subtracted from the average value for the comparative product. The pairwise differences thus obtained in the mean values of the ratings for the 10 experimental subjects are shown in Table 2 below. Results: All comparative shampoos were judged to be inferior in their hair cosmetic properties to the standard shampoo (shampoo No. 1 according to the invention).
Claims (1)
アニオン性洗剤塩;と (a) 0.1〜4重量%の3−(トリメチルアミノ)−
2−ヒドロキシプロピルグア塩化物、 (b) 0.5〜5重量%の、反応性アミノ基及びポリ
アルキレンオキサイド基を含む水溶性ポリアミ
ンとエピクロロヒドリン又は分子中に一個より
多くのエポキサイド及び/又はハロヒドリン基
を含む化合物との易水溶性で硬化可能な重縮合
生成物、 (c) 1〜4重量%の、グリセリンと4〜20モルの
エチレンオキサイドとのエチレンオキサイド付
加物と1〜2モルのC8〜C18脂肪酸とのエステ
ル化生成物、及び (d) 0.1〜1重量%の、平均分子量が10000〜
70000であるポリビニルピロリドン、からなり、
(a):(b):(c):(d)の重量比が1:0.5〜4:0.5〜
4:0.15〜0.5である、1.7〜14重量%の整髪剤
混合物;とからなり、前記洗剤と前記整髪剤混
合物との重量比が10:1〜1:1である、整髪
用シヤンプー。 2 前記アニオン性洗剤塩が、C8〜C18アルキル
硫酸塩、分子中に1〜6個のグリコールエーテル
基を有するC8〜C18アルキルポリグリコールエー
テル、C10〜C18アルカンスルホン酸塩、C10〜C18
オレフインスルホン酸塩、C8〜C18脂肪酸アルキ
ルアミドポリグリコールエーテル硫酸塩、C8〜
C18脂肪族モノグリセライド硫酸塩、C8〜C18アル
キルスルホ琥珀酸塩、C6〜C10ジアルキルスルホ
琥珀酸塩、分子中に2〜6個のポリグリコールエ
ーテル基を有するC8〜C18アルキルポリグリコー
ルエーテルカルボン酸塩、C8〜C18アシルタウラ
イド、及びC8〜C18アシルイセチオネートからな
る群から選択される、アルカリ金属、マグネシウ
ム、アンモニウム、又はC2〜C3アルカノールア
ンモニウムの塩である、請求項1記載のシヤンプ
ー。 3 2〜8重量%の前記整髪剤混合物が存在す
る、請求項2記載のシヤンプー。 4 前記アニオン性洗剤が8〜30重量%の量で存
在する、請求項3記載のシヤンプー。 5 前記洗剤と前記整髪剤混合物との重量比が
2.5:1〜1.5:1である、請求項4記載のシヤン
プー。 6 前記アニオン性洗剤が2:1〜1:1の重量
比の前記C8〜C18アルキルポリグリコールエーテ
ル硫酸塩とC8〜C18アルキル硫酸塩との混合物で
ある、請求項2ないし5いずれか記載のシヤンプ
ー。Claims: 1. An anionic detergent salt in an aqueous solution of 5 to 50% by weight in an aqueous medium; and (a) 0.1 to 4% by weight of 3-(trimethylamino)-
(b) 0.5 to 5% by weight of a water-soluble polyamine containing reactive amino groups and polyalkylene oxide groups and epichlorohydrin or more than one epoxide and/or halohydrin in the molecule; readily water-soluble and curable polycondensation products with compounds containing groups, (c) 1 to 4% by weight of ethylene oxide adducts of glycerin and 4 to 20 mol of ethylene oxide and 1 to 2 mol of C esterification products with 8 to C18 fatty acids, and (d) 0.1 to 1% by weight, with an average molecular weight of 10000 to
consisting of polyvinylpyrrolidone, which is 70,000;
The weight ratio of (a):(b):(c):(d) is 1:0.5~4:0.5~
1.7 to 14% by weight of a hair styling agent mixture having a ratio of 4:0.15 to 0.5; and a weight ratio of the detergent to the hair styling agent mixture being 10:1 to 1:1. 2. The anionic detergent salt is a C8 to C18 alkyl sulfate, a C8 to C18 alkyl polyglycol ether having 1 to 6 glycol ether groups in the molecule, a C10 to C18 alkanesulfonate, C10 ~ C18
Olefin Sulfonate, C8 ~ C18 Fatty Acid Alkylamide Polyglycol Ether Sulfate, C8 ~
C18 aliphatic monoglyceride sulfate, C8 to C18 alkyl sulfosuccinate, C6 to C10 dialkyl sulfosuccinate, C8 to C18 alkyl with 2 to 6 polyglycol ether groups in the molecule of an alkali metal, magnesium, ammonium, or C2 - C3 alkanol ammonium selected from the group consisting of polyglycol ether carboxylates, C8 -C18 acyl taurides, and C8 - C18 acyl isethionates. The shampoo according to claim 1, which is a salt. 3. Shampoo according to claim 2, wherein from 2 to 8% by weight of said hair styling agent mixture is present. 4. Shampoo according to claim 3, wherein said anionic detergent is present in an amount of 8 to 30% by weight. 5 The weight ratio of the detergent and the hair styling agent mixture is
The shampoo according to claim 4, wherein the ratio is 2.5:1 to 1.5:1. 6. Any of claims 2 to 5, wherein the anionic detergent is a mixture of the C8 - C18 alkyl polyglycol ether sulfate and C8 - C18 alkyl sulfate in a weight ratio of 2:1 to 1:1. Shampoo as described.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK4637/82 | 1982-10-19 | ||
DK463782A DK155912C (en) | 1982-10-19 | 1982-10-19 | HAIR CONDITIONING SHAMPOO |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59102996A JPS59102996A (en) | 1984-06-14 |
JPH0524127B2 true JPH0524127B2 (en) | 1993-04-06 |
Family
ID=8135341
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58195107A Granted JPS59102996A (en) | 1982-10-19 | 1983-10-18 | Shampoo |
Country Status (21)
Country | Link |
---|---|
JP (1) | JPS59102996A (en) |
AU (1) | AU555029B2 (en) |
BE (1) | BE898006A (en) |
CA (1) | CA1214728A (en) |
CH (1) | CH658383A5 (en) |
DE (1) | DE3336609C2 (en) |
DK (1) | DK155912C (en) |
ES (1) | ES8601683A1 (en) |
FI (1) | FI81003C (en) |
FR (1) | FR2534473B1 (en) |
GR (1) | GR79410B (en) |
HK (1) | HK61091A (en) |
IT (1) | IT1170517B (en) |
MX (1) | MX156772A (en) |
NL (1) | NL8303609A (en) |
NO (1) | NO160049C (en) |
NZ (1) | NZ205951A (en) |
PH (1) | PH19337A (en) |
PT (1) | PT77506B (en) |
SE (1) | SE461829B (en) |
ZA (1) | ZA837646B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9000237D0 (en) * | 1990-01-10 | 1990-03-07 | Unilever Plc | Shampoo composition |
FR2977796B1 (en) * | 2011-07-12 | 2014-12-19 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE POLYAMINE, AT LEAST ONE POLYOL AND AT LEAST ONE ANIONIC ASSOCIATIVE THICKENING POLYMER |
FR2977795B1 (en) * | 2011-07-12 | 2014-06-27 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE FATTY POLYAMINE, AT LEAST ONE POLYOL AND AT LEAST ONE NON-IONIC POLYURETHANE |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2024051C3 (en) * | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Use of the esterification products of glycerol-ethylene oxide adducts with fatty acids as refatting agents in cosmetic preparations |
NL7104188A (en) * | 1971-03-29 | 1972-10-03 | Hair setting agent - contng hetero polysaccharide as active constituent | |
US4292212A (en) * | 1978-11-29 | 1981-09-29 | Henkel Corporation | Shampoo creme rinse |
US4298494A (en) * | 1979-03-27 | 1981-11-03 | Lever Brothers Company | Shampoo |
US4321256A (en) * | 1979-07-19 | 1982-03-23 | Lever Brothers Company | Shampoo containing a polyglycol-polyamine condensation resin and a phosphate ester |
-
1982
- 1982-10-19 DK DK463782A patent/DK155912C/en active
-
1983
- 1983-10-07 DE DE3336609A patent/DE3336609C2/en not_active Expired - Fee Related
- 1983-10-10 MX MX199074A patent/MX156772A/en unknown
- 1983-10-13 ZA ZA837646A patent/ZA837646B/en unknown
- 1983-10-13 NZ NZ205951A patent/NZ205951A/en unknown
- 1983-10-14 GR GR72708A patent/GR79410B/el unknown
- 1983-10-14 PT PT77506A patent/PT77506B/en not_active IP Right Cessation
- 1983-10-17 FR FR8316480A patent/FR2534473B1/en not_active Expired
- 1983-10-17 IT IT49165/83A patent/IT1170517B/en active
- 1983-10-17 BE BE0/211714A patent/BE898006A/en not_active IP Right Cessation
- 1983-10-18 ES ES526540A patent/ES8601683A1/en not_active Expired
- 1983-10-18 SE SE8305711A patent/SE461829B/en not_active IP Right Cessation
- 1983-10-18 AU AU20265/83A patent/AU555029B2/en not_active Ceased
- 1983-10-18 CA CA000439189A patent/CA1214728A/en not_active Expired
- 1983-10-18 NO NO833796A patent/NO160049C/en unknown
- 1983-10-18 JP JP58195107A patent/JPS59102996A/en active Granted
- 1983-10-18 FI FI833802A patent/FI81003C/en not_active IP Right Cessation
- 1983-10-19 PH PH29718A patent/PH19337A/en unknown
- 1983-10-19 CH CH5696/83A patent/CH658383A5/en not_active IP Right Cessation
- 1983-10-19 NL NL8303609A patent/NL8303609A/en not_active Application Discontinuation
-
1991
- 1991-08-08 HK HK610/91A patent/HK61091A/en unknown
Also Published As
Publication number | Publication date |
---|---|
NO160049B (en) | 1988-11-28 |
NZ205951A (en) | 1986-04-11 |
PT77506A (en) | 1983-11-01 |
HK61091A (en) | 1991-08-16 |
DK155912B (en) | 1989-06-05 |
CH658383A5 (en) | 1986-11-14 |
GR79410B (en) | 1984-10-22 |
SE8305711L (en) | 1984-04-20 |
FI833802A (en) | 1984-04-20 |
DE3336609A1 (en) | 1984-04-19 |
NO833796L (en) | 1984-04-24 |
DK463782A (en) | 1984-04-20 |
PH19337A (en) | 1986-03-21 |
ES526540A0 (en) | 1985-11-01 |
NL8303609A (en) | 1984-05-16 |
IT1170517B (en) | 1987-06-03 |
CA1214728A (en) | 1986-12-02 |
JPS59102996A (en) | 1984-06-14 |
FR2534473B1 (en) | 1985-07-19 |
MX156772A (en) | 1988-09-30 |
FI833802A0 (en) | 1983-10-18 |
NO160049C (en) | 1989-03-08 |
BE898006A (en) | 1984-04-17 |
FI81003B (en) | 1990-05-31 |
DE3336609C2 (en) | 1993-11-18 |
SE8305711D0 (en) | 1983-10-18 |
AU2026583A (en) | 1984-05-03 |
SE461829B (en) | 1990-04-02 |
ZA837646B (en) | 1985-09-25 |
AU555029B2 (en) | 1986-09-11 |
DK155912C (en) | 1989-10-23 |
FI81003C (en) | 1990-09-10 |
PT77506B (en) | 1986-02-12 |
ES8601683A1 (en) | 1985-11-01 |
FR2534473A1 (en) | 1984-04-20 |
IT8349165A0 (en) | 1983-10-17 |
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