JP2019529358A - Defi及びタウレートアミド混合物並びにそのプロセス - Google Patents
Defi及びタウレートアミド混合物並びにそのプロセス Download PDFInfo
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- JP2019529358A JP2019529358A JP2019508934A JP2019508934A JP2019529358A JP 2019529358 A JP2019529358 A JP 2019529358A JP 2019508934 A JP2019508934 A JP 2019508934A JP 2019508934 A JP2019508934 A JP 2019508934A JP 2019529358 A JP2019529358 A JP 2019529358A
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- defi
- ata
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- taurate
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- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 35
- -1 taurate amide Chemical class 0.000 title claims abstract description 29
- 229940104261 taurate Drugs 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 29
- 239000000194 fatty acid Substances 0.000 claims description 29
- 229930195729 fatty acid Natural products 0.000 claims description 29
- 150000004665 fatty acids Chemical class 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 21
- 229960003080 taurine Drugs 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical group 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 13
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 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 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229940045998 sodium isethionate Drugs 0.000 description 3
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 2
- UKSFMDODPANKJI-UHFFFAOYSA-M sodium;2-[methyl(octadecanoyl)amino]ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)N(C)CCS([O-])(=O)=O UKSFMDODPANKJI-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JJKVMNNUINFIRK-UHFFFAOYSA-N 4-amino-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(N)C=C1 JJKVMNNUINFIRK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
a)脂肪酸(例えば、C8〜C22、好ましくはC10〜C18脂肪酸)、脂肪酸対タウリン及び/又はタウリン塩の比が1.2:1〜10:1、好ましくは1.5:1〜8:1、より好ましくは1.5:1〜5:1であるタウリン及び/又はタウリン酸塩並びに触媒を200℃以下、好ましくは180℃〜195℃の温度で合わせるステップであって、述べた通り、少量の(以下のステップ(b)において使用される)イセチオン酸アルカリ金属塩が初期の反応において存在してもよいが、これが最小限(使用されることになる(すべて又はほとんどすべてがステップ(b)において使用される)イセチオン酸塩全体の好ましくは10%未満、典型的には1%未満である、ステップと、
b)反応(典型的には、これは約1〜2時間になり、ATAの収率は、80%以上、好ましくは81〜100%、より好ましくは82〜95%である。)が完了したら、大部分又はすべてのイセチオン酸アルカリ金属塩をアルキルタウレートアミド及び残留脂肪酸の混合物に200℃以下、好ましくは180〜195℃の温度で加えるステップ(この第2のステップの後のDEFIの最終収率は、45〜85%、好ましくは55〜85%の範囲になり得る。)と
を含む。
1)プロセスの第1の部分において、脂肪酸(例えば、C8〜C22脂肪酸)、(脂肪酸対タウリン及び/又はタウリン酸塩の比が1.2:1〜10:1、好ましくは1.5:1〜8:1、より好ましくは1.5:1〜5:1である)タウリン及び/又はタウリン塩並びに触媒を180℃〜200℃の温度で合わせるステップと、
2)反応の第1の部分が完了したら(典型的には1〜2時間以内)、大部分又はすべてのイセチオン酸アルカリ金属塩を混合物に200℃以下、好ましくは180℃〜195℃の温度で加えるステップと
を含む。典型的には、触媒は、第2のステップにおいて使用されない。
RNHCH2CH2SO3H
(式中、Rは、例えば、水素又はメチルでもよい。)
を有するタウリン(例えば、2−アミノエタンスルホン酸)、又は硫酸基上の水素が、その代わりに、ナトリウム又はカリウム対イオンなどの対イオンであるタウリン酸塩と合わせられる。理論上、酸及び塩の混合物を使用することができる。
「L」値を測定するためのプロトコル
生成物の色は、ハンターLabカラースケールにより評価される。これは、当業者に周知のカラースケールである(例えば、L、a及びbの式が定義されている、ハンターLabによる“Application Note”,“Insight on Color”,Vol.8,No.9を参照されたい)。ハンタースケールにおいて、重要なパラメータは、白色度の反射度であるL値になる。
本発明の実施例の手順
機械式撹拌装置、冷却器、溶媒トラップ/受器及び熱電対/窒素(N2)流入口を備えた四つ口の250ml丸底フラスコ内にN−メチルタウリンナトリウム(12.5g、55%溶液、1eq.)を加えた。N2流を0.2リットル/分(LPM)に設定した。水を除去するため、N−メチルタウリンの溶液を約150℃まで加熱した。反応温度を約190℃まで上げ、ラウリン酸(42.89g、5eq.)及び酸化亜鉛(0.7g、0.2eq.)を加えた。反応混合物を190℃で1時間撹拌した。
Claims (15)
- DEFIとアルキルアミドタウレートとの混合物を調製するためのプロセスであって、
a)前記プロセスの第1の部分において、C8〜C22脂肪酸、脂肪酸対タウリン及び/又はタウリン酸塩の比が1.2:1〜10:1であるタウリン及び/又はタウリン塩並びに触媒を200℃以下、好ましくは180℃〜195℃の温度で合わせるステップと、
b)反応の第1の部分が完了したら、90超〜100%のイセチオン酸アルカリ金属塩を前記混合物に200℃以下、好ましくは180℃〜195℃の温度で加えるステップと
を含む、プロセス。 - 脂肪酸対タウリン及び/又はタウリン酸塩の比が1.5:1〜8:1である、請求項1又は2に記載のプロセス。
- 脂肪酸対タウレート及び/又はタウリン塩の前記比が1.5:1〜5:1である、請求項2に記載のプロセス。
- 前記触媒が、有機酸若しくは無機酸、強酸又は前記2の混合物の多価金属イオン塩である、請求項1から3のいずれかに記載のプロセス。
- 前記触媒が金属酸化物触媒である、請求項1から4のいずれか一項に記載のプロセス。
- 前記触媒が、ZnO、MgO又はCaOである、請求項5に記載のプロセス。
- ステップ(a)の反応温度が、200℃以下、好ましくは180℃〜195℃の温度である、請求項1から6のいずれかに記載のプロセス。
- ステップ(b)において加えられるイセチオン酸アルカリ金属塩が、180℃〜195℃の温度で加えられる、請求項1から7のいずれかに記載のプロセス。
- アルキルタウレートアミドは、80〜96のDEFI及びATA混合物のL値により定義される褐変が実質的にない、請求項1から8のいずれかに記載のプロセス。
- 請求項1から9のいずれかにより得ることができる、DEFIとアルキルアミドタウレートとの混合物。
- 80〜96のATA/DEFI混合物のL値を有する、請求項10に記載の混合物。
- DEFI対ATAの比が、0.1:1〜7:1、好ましくは0.4:1〜7:1である、請求項10又は11に記載の混合物。
- 80〜96、好ましくは90〜96のATA/DEFI混合物のL値を有する、DEFIとアルキルアミドタウレートとの混合物。
- DEFI対ATAの比が、0.1:1〜7:1、好ましくは0.4:1〜7:1である、請求項13に記載の混合物。
- 最終混合物中のDEFI対ATAの前記比を制御するための、請求項1から9のいずれか一項に記載のプロセスの使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16191203 | 2016-09-28 | ||
EP16191203.5 | 2016-09-28 | ||
PCT/EP2017/072312 WO2018059889A1 (en) | 2016-09-28 | 2017-09-06 | Defi and taurate amide mixtures and processes thereof |
Publications (2)
Publication Number | Publication Date |
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JP2019529358A true JP2019529358A (ja) | 2019-10-17 |
JP7094503B2 JP7094503B2 (ja) | 2022-07-04 |
Family
ID=57044877
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JP2019508934A Active JP7094503B2 (ja) | 2016-09-28 | 2017-09-06 | Defi及びタウレートアミド混合物並びにそのプロセス |
Country Status (10)
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---|---|
US (2) | US11274075B2 (ja) |
EP (1) | EP3519384B1 (ja) |
JP (1) | JP7094503B2 (ja) |
CN (1) | CN109689622A (ja) |
BR (1) | BR112019003540B1 (ja) |
CA (1) | CA3033228A1 (ja) |
EA (1) | EA037627B1 (ja) |
MX (1) | MX2019002587A (ja) |
WO (1) | WO2018059889A1 (ja) |
ZA (1) | ZA201900998B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2960280A1 (en) * | 2014-06-26 | 2015-12-30 | E.T.C. S.r.l. | Photocrosslinkable compositions, patterned high k thin film dielectrics and related devices |
BR112020003992B1 (pt) * | 2017-10-03 | 2023-01-10 | Unilever Ip Holdings B.V. | Processos para fabricar alquil taurato amidas |
CN111072524A (zh) * | 2019-12-23 | 2020-04-28 | 张家港格瑞特化学有限公司 | 采用高温结晶制备脂肪酰基氨基酸表面活性剂的方法 |
Citations (4)
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JP2002205923A (ja) * | 2001-01-09 | 2002-07-23 | Shiseido Co Ltd | 染毛料 |
US6562874B1 (en) * | 1999-12-07 | 2003-05-13 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Compositions comprising combination of DEFI and modified DEFI and methods of making |
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JP2016506376A (ja) * | 2013-05-08 | 2016-03-03 | ギャラクシー サーファクタンツ エルティディ.Galaxy Surfactants Ltd. | O−アシルイセチオン酸塩とn−アシルアミノ酸界面活性剤とのブレンド |
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US4405526A (en) * | 1981-08-24 | 1983-09-20 | Lever Brothers Company | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
US4536338A (en) * | 1983-11-09 | 1985-08-20 | Lever Brothers Company | Process for manufacture of fatty acid esters of hydroxy sulfonates |
DE4432366A1 (de) * | 1994-09-12 | 1996-03-14 | Henkel Kgaa | Milde Detergensgemische |
US7166136B2 (en) * | 2001-01-09 | 2007-01-23 | Shiseido Company, Ltd. | Hairdye preparation |
GB0912468D0 (en) * | 2009-07-17 | 2009-08-26 | Innospec Ltd | Composition and method |
-
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US6562874B1 (en) * | 1999-12-07 | 2003-05-13 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Compositions comprising combination of DEFI and modified DEFI and methods of making |
JP2002205923A (ja) * | 2001-01-09 | 2002-07-23 | Shiseido Co Ltd | 染毛料 |
JP2009057383A (ja) * | 2007-08-30 | 2009-03-19 | Clariant Internatl Ltd | イセチオネート、タウレート及びベタインの水性濃厚液 |
JP2016506376A (ja) * | 2013-05-08 | 2016-03-03 | ギャラクシー サーファクタンツ エルティディ.Galaxy Surfactants Ltd. | O−アシルイセチオン酸塩とn−アシルアミノ酸界面活性剤とのブレンド |
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SOFW JOURNAL, vol. 133, JPN6022013620, 2007, pages 56 - 62, ISSN: 0004748136 * |
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US11780806B2 (en) | 2023-10-10 |
US20220169597A1 (en) | 2022-06-02 |
ZA201900998B (en) | 2020-05-27 |
JP7094503B2 (ja) | 2022-07-04 |
CA3033228A1 (en) | 2018-04-05 |
EA037627B1 (ru) | 2021-04-23 |
EP3519384B1 (en) | 2020-04-22 |
US11274075B2 (en) | 2022-03-15 |
BR112019003540A2 (pt) | 2019-05-21 |
US20210284605A1 (en) | 2021-09-16 |
EA201990270A1 (ru) | 2019-08-30 |
CN109689622A (zh) | 2019-04-26 |
EP3519384A1 (en) | 2019-08-07 |
BR112019003540B1 (pt) | 2022-06-21 |
WO2018059889A1 (en) | 2018-04-05 |
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