EP0482687B1 - Composition coulable liquide concentrée - Google Patents

Composition coulable liquide concentrée Download PDF

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Publication number
EP0482687B1
EP0482687B1 EP91202510A EP91202510A EP0482687B1 EP 0482687 B1 EP0482687 B1 EP 0482687B1 EP 91202510 A EP91202510 A EP 91202510A EP 91202510 A EP91202510 A EP 91202510A EP 0482687 B1 EP0482687 B1 EP 0482687B1
Authority
EP
European Patent Office
Prior art keywords
composition
weight
internal olefin
salt
sulphonates
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
Application number
EP91202510A
Other languages
German (de)
English (en)
Other versions
EP0482687A1 (fr
Inventor
Johan Stapersma
Roelof Van Ginkel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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Filing date
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Publication of EP0482687A1 publication Critical patent/EP0482687A1/fr
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Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/201—Monohydric alcohols linear
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • 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
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/2017—Monohydric alcohols branched
    • 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
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear
    • 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/06—Ether- or thioether carboxylic acids
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the invention relates to a concentrated, liquid, pourable composition
  • a concentrated, liquid, pourable composition comprising an alkali or earth alkali metal or ammonium salt or a salt of an organic base of an internal olefin sulphonic acid, having 8 to 26 carbon atoms.
  • a detergent composition comprising an alkali or earth alkali metal or ammonium salt or a salt of an organic base of an internal olefin sulphonic acid, having from 8 to 26 carbon atoms, and containing at least 25% by weight of beta-hydroxysulphonate, calculated on the total amount of sulphonate.
  • compositions with 50 to 90% by weight of beta-hydroxysulphonate are used.
  • compositions may contain other surfactants of anionic, nonionic, amphoteric or cationic type and depending upon the formulations to be used the compositions may contain builders, sequestring agents, bleaching agents, bleach activators, greyness-preventing agents, soil release polymers, foam control agents, fluorescent whiteners, enzymes and perfumes.
  • the compositions are thus suitable for a number of applications such as solid and liquid laundry detergents, dishwash detergents, cleaning agents, liquid soaps, shampoos and liquid scouring agents.
  • the invention relates to a concentrated liquid, pourable composition
  • a concentrated liquid, pourable composition comprising:
  • inventive compositions are easily storageable, handlable and transportable. Furthermore, they may be easily spray-dried or converted into less concentrated compositions.
  • the internal olefin sulphonate contains at least 25% by weight of beta-hydroxy sulphonate, preferably at least 50%, more preferably more than 70% by weight of beta-hydroxy sulphonate.
  • Preferred internal olefin sulphonic acids contain from 13 to 24 carbon atoms.
  • the sulphonic acids may be present in the form of their salts with sodium, potassium, ammonium or an organic base.
  • the internal olefin sulphonates are generally prepared by reacting in a film reactor an internal olefin having from 8 to 26 carbon atoms with a sulphonating agent, in a mol ratio of sulphonating agent to internal olefin of 1.3 to 0.9, preferably 1.15 to 0.95, while cooling the reactor with a cooling means having a temperature not exceeding 35 °C and allowing the reaction product of the sulphonating step to neutralize and hydrolyze.
  • the internal olefins used as starting material are those having 8 to 26 carbon atoms, preferably 13 to 24 carbon atoms.
  • Examples of the internal olefins are those having the general formula: wherein each of R 1 , R 2 , R 3 and R 4 independently are linear or branched alkyl groups or hydrogen and the total carbon number of R 1 , R 2 , R 3 and R 4 is from 6 to 24, and wherein at least one of R 1 and R 2 and one of R 3 and R 4 is an alkyl group.
  • the neutralization/hydrolysis step is carried out directly after the sulphonating step. An ageing step is consequently avoided or minimized.
  • the sulphonation may be carried out batchwise, semi-continuously or continuously, preferably continuously.
  • the neutralization/hydrolysis is preferably carried out continuously and at a temperature of 20 to 50 °C, preferably 30 to 45 °C.
  • Hydrolysis is preferably carried out continuously and at temperatures of 140-190 °C.
  • aqueous base For the neutralization/hydrolysis an aqueous base is generally used. To prepare concentrated products, the amount of water is regulated accordingly.
  • Component c) may be included in the composition at the same time when water is added.
  • This third component is a lower alcohol, a nonionic surfactant, a polyethylene glycol, a polypropylene glycol, a salt-tolerant anionic surfactant or a mixture thereof.
  • lower alcohols examples include methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol, tert.butanol, a pentanol or a hexanol, ethylene glycol, propylene glycol, a linear or branched C 1 to C 6 mono-alkylether of mono- or di-ethylene glycol, a linear or branched C 1 to C 6 mono-alkylether of mono- or di-propylene glycol, or a mixture thereof.
  • nonionic surfactants are C 7 to C 18 -alcohols that are alkoxylated with ethylene oxide and/or propylene oxide with a minimum degree of alkoxylation of 2.
  • nonionic surfactants are C 6 to C 12 -alkylphenols, alkoxylated with ethylene oxide and/or propylene oxide with a minimum degree of alkoxylation of 2.
  • nonionic surfactants are hydrophilic C 8 to C 18 -alkyl polyglycosides with 1 to 4 carbohydrate units.
  • Polyethylene glycols may have a molecular weight from 300 to 5000, preferably from 800 to 4000.
  • Polypropylene glycols may have a molecular weight from 250 to 4000, preferably from 400 to 2500.
  • salt-tolerant anionic surfactants are a C 8 to C 18 -alcoholalkoxy carboxylate salt with a degree of alkoxylation of 1 to 10, or C 6 to C 10 aliphatic or aromatic sulphonates.
  • composition according to the invention may comprise some impurities, such as unreacted olefin and inorganic salt.
  • impurities such as unreacted olefin and inorganic salt.
  • the amounts of them generally do not exceed about 5% by weight each, calculated on the internal olefin sulphonate.
  • the sulphur trioxide was prepared by burning sulphur in dry air followed by conversion of the sulphur dioxide to sulphur trioxide over a vanadium pentoxide catalyst at about 450 °C.
  • the reactor was cooled by flowing water of a temperature of 8 to 11 °C along the outside of the stainless steel reactor tube.
  • the internal olefin mixture (either A, or B or C) flowed along the inner part of the reactor wall as a flowing film in downward direction and was allowed to react cocurrently with the sulphur trioxide, which was introduced at the same time in the top of the reactor, diluted with air. The reaction proceeded continuously.
  • the reaction mixture coming out of the falling film sulphonation reactor was conducted into a continuous neutralization loop, provided with a combined pump/high sheer mixer and two heat exchangers, and having a volume of about 26 litres; in that continuous neutralization loop the reaction mixture coming from the sulphonation reactor was subjected to neutralization/hydrolysis at 30-45 °C by, at the same time, continuously introducing into the loop streams of i) a concentrated (50% by weight) aqueous sodium hydroxide solution, ii) water, and iii) water plus nonionic surfactant and intimately mixing these streams by means of the combined pump/high sheer mixer and recycling in the neutralization loop.
  • the recycle rate in the loop was about 20 times greater than the intake rate of the reaction mixture coming from the film reactor.
  • the average residence time of the neutralization/hydrolysis mixture in the continuous neutralization loop was dependent on the precise composition of a particular product and of the initial olefin feed rate, and amounted to 40-55 min.
  • the intake rate of the concentrated aqueous sodium hydroxide stream was adjusted on the basis of alkalinity measurements in the end-product (i.e. after the continuous hydrolysis step), which was aimed to be slightly basic.
  • the amounts of water (total) and nonionic surfactant were calculated on the basis of the desired composition.
  • the anionic active matter concentration was actually measured in the end-product (i.e. after the continuous hydrolysis step) during the production.
  • compositions given in the Table are all liquid and pourable at 20 °C and can be pumped at that temperature, whilst this holds also for the materials during production in the continuous neutralization loop and the continuous hydrolysis reactor. Reducing during production the amount of nonionic surfactant in Examples 1 and 7 to zero leads to products that can not be pumped through the neutralization/hydrolysis reactor even in spite of the higher temperature in the neutralization loop.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Claims (11)

  1. Composition coulable, liquide, concentrée, comprenant:
    a) de 60 à 90% en poids d'un sel de métal alcalin ou alcalino-terreux ou d'ammonium, ou d'un sel d'une base organique, d'un acide oléfinesulfonique interne, comportant 8 à 26 atomes de carbone, ces oléfinesulfonates internes comportant au moins 25% en poids de β-hydroxysulfonates;
    b) de 8 à 38% en poids d'eau; et
    c) de 2 à 32% en poids d'un alcool inférieur, d'un tensioactif non ionique, d'un polyéthylèneglycol, d'un polypropylèneglycol, d'un tensioactif anionique tolérant aux sels, ou d'un mélange de ceux-ci.
  2. Composition selon la revendication 1, dans laquelle les oléfinesulfonates internes comprennent au moins 50% en poids de β-hydroxysulfonates.
  3. Composition selon la revendication 1 ou 2, dans laquelle les oléfinesulfonates internes comprennent au moins 70% en poids de β-hydroxysulfonates.
  4. Composition selon une ou plusieurs des revendications 1-3, dans laquelle le groupement acide oléfinesulfonique interne comprend de 13 à 24 atomes de carbone.
  5. Composition selon une ou plusieurs des revendications 1-4, dans laquelle l'alcool inférieur est le méthanol, l'éthanol, le propanol, l'isopropanol, le butanol, l'isobutanol, le t-butanol, le pentanol ou l'hexanol, l'éthylèneglycol, le propylèneglycol, un éther monoalkylique en C1 à C6, linéaire ou ramifié, de mono- ou de di-éthylèneglycol, un éther monoalkylique en C1 à C6, linéaire ou ramifié, de mono- ou de dipropylèneglycol, ou un mélange de ceux-ci.
  6. Composition selon une ou plusieurs des revendications 1-4, dans laquelle le tensioactif non ionique est un alcool en C7 à C18 qui est alcoxylé avec de l'oxyde d'éthylène et/ou de l'oxyde de propylène, avec un degré minimum d'alcoxylation de 2.
  7. Composition selon une ou plusieurs des revendications 1-4, dans laquelle le tensioactif non ionique comprend un alkylphénol en C6 à C12, alcoxylé avec de l'oxyde d'éthylène et/ou de l'oxyde de propylène, avec un degré minimum d'alcoxylation de 2.
  8. Composition selon une ou plusieurs des revendications 1-4, dans laquelle le tensioactif non ionique comprend un alkylpolyglycoside hydrophile en C8 à C18, avec 1 à 4 motifs glucide.
  9. Composition selon une ou plusieurs des revendications 1-4, comprenant du polyéthylèneglycol ayant une masse moléculaire de 300 à 5 000, de préférence de 800 à 4 000.
  10. Composition selon une ou plusieurs des revendications 1-4, comprenant du polypropylèneglycol ayant une masse moléculaire de 250 à 4 000, de préférence de 400 à 2 500.
  11. Composition selon une ou plusieurs des revendications 1-4, dans laquelle le tensioactif anionique tolérant aux sels comprend un sel alcoolalcoxycarboxylate en C8 à C18, avec un degré d'alcoxylation de 1 à 10, ou un sulfonate aliphatique ou aromatique en C6 à C10.
EP91202510A 1990-10-26 1991-09-26 Composition coulable liquide concentrée Expired - Lifetime EP0482687B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909023366A GB9023366D0 (en) 1990-10-26 1990-10-26 Concentrated,liquid,pourable composition
GB9023366 1990-10-26

Publications (2)

Publication Number Publication Date
EP0482687A1 EP0482687A1 (fr) 1992-04-29
EP0482687B1 true EP0482687B1 (fr) 1996-06-12

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EP (1) EP0482687B1 (fr)
DE (1) DE69120205T2 (fr)
GB (1) GB9023366D0 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8403044B2 (en) 2009-05-05 2013-03-26 Stepan Company Sulfonated internal olefin surfactant for enhanced oil recovery
EP3467081A4 (fr) * 2016-05-31 2019-12-18 Kao Corporation Composition d'agent nettoyant pour fibres
EP3467080B1 (fr) * 2016-05-31 2023-03-22 Kao Corporation Composition détergente pour produit textile
EP3467196B1 (fr) * 2016-05-31 2024-11-27 Kao Corporation Procédé de nettoyage de vêtements

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Publication number Priority date Publication date Assignee Title
EP2261298A1 (fr) 2009-06-10 2010-12-15 Shell Internationale Research Maatschappij B.V. Procédé de récupération d'hydrocarbures améliorés
EP2186783A3 (fr) 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation d'oléfines
EP2186784A3 (fr) 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation et la récupération d'oléfines
EP2186785A3 (fr) 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Procédé pour la séparation des oléfines des paraffines
BR112013028322A2 (pt) 2011-05-27 2017-01-10 Shell Int Research composição de recuperação de hidrocarboneto, artigo conformado, e, processo para tratar uma formação contendo hidrocarboneto e para preparar uma composição de recuperação de hidrocarboneto
AR090958A1 (es) 2012-05-09 2014-12-17 Shell Int Research Metodo para la recuperacion mejorada de hidrocarburos
JP6215629B2 (ja) * 2012-09-20 2017-10-18 花王株式会社 内部オレフィンスルホン酸塩組成物及びこれを含有する洗浄剤組成物
WO2014119726A1 (fr) * 2013-02-01 2014-08-07 花王株式会社 Composition de sulfonate d'oléfine interne
WO2014119728A1 (fr) 2013-02-01 2014-08-07 花王株式会社 Composition de sulfonate d'oléfine interne
WO2014119727A1 (fr) 2013-02-01 2014-08-07 花王株式会社 Composition de sulfonate d'oléfine interne
MX2015010817A (es) * 2013-03-06 2015-11-30 Shell Int Research Composicion de sulfonato de olefina interna.
JP2015178466A (ja) * 2014-03-19 2015-10-08 ロレアル 内部オレフィンスルホン酸塩及び１種のポリマー懸濁剤を含有する起泡性組成物
JP2015178467A (ja) * 2014-03-19 2015-10-08 ロレアル 内部オレフィンスルホン酸塩及び１種の起泡増強剤又は起泡増進剤を含有する起泡性組成物
KR102657749B1 (ko) 2015-10-19 2024-04-17 쉘 인터내셔날 리써취 마트샤피지 비.브이. 스타이렌의 제조 방법
EP3467083B1 (fr) * 2016-05-31 2021-03-31 Kao Corporation Composition d'agent nettoyant liquide pour article en fibres
AU2017272752B2 (en) 2016-05-31 2021-10-07 Kao Corporation Liquid detergent composition for textile products
EP3162872A1 (fr) * 2016-06-24 2017-05-03 Shell Internationale Research Maatschappij B.V. Composition de sulfonate oléfine interne et son utilisation dans la récuperation ameliorée du pétrole
JP7051685B2 (ja) * 2016-08-09 2022-04-11 花王株式会社 界面活性剤組成物
RU2748253C2 (ru) * 2016-12-26 2021-05-21 Као Корпорейшн Способ обработки текстильного продукта
US11584881B2 (en) * 2017-06-30 2023-02-21 Dow Global Technologies Llc Low-temperature stabilized surfactant blend for enhanced oil recovery

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0351928A1 (fr) * 1988-07-20 1990-01-24 Shell Internationale Researchmaatschappij B.V. Procédé pour la préparation de sulfonates d'oléfines internes

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Publication number Priority date Publication date Assignee Title
JPS55111455A (en) * 1979-02-20 1980-08-28 Lion Corp Transparent aqueous solution of olefinsulfonate
JPS61247799A (ja) * 1985-04-26 1986-11-05 ライオン株式会社 高濃度界面活性剤スラリ−

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0351928A1 (fr) * 1988-07-20 1990-01-24 Shell Internationale Researchmaatschappij B.V. Procédé pour la préparation de sulfonates d'oléfines internes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8403044B2 (en) 2009-05-05 2013-03-26 Stepan Company Sulfonated internal olefin surfactant for enhanced oil recovery
EP3467081A4 (fr) * 2016-05-31 2019-12-18 Kao Corporation Composition d'agent nettoyant pour fibres
EP3467080B1 (fr) * 2016-05-31 2023-03-22 Kao Corporation Composition détergente pour produit textile
EP3467196B1 (fr) * 2016-05-31 2024-11-27 Kao Corporation Procédé de nettoyage de vêtements

Also Published As

Publication number Publication date
DE69120205D1 (de) 1996-07-18
GB9023366D0 (en) 1990-12-05
EP0482687A1 (fr) 1992-04-29
DE69120205T2 (de) 1997-02-06

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