EP0482687A1 - Konzentrierte, flüssige, fliessfähige Zusammensetzung - Google Patents

Konzentrierte, flüssige, fliessfähige Zusammensetzung Download PDF

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Publication number
EP0482687A1
EP0482687A1 EP91202510A EP91202510A EP0482687A1 EP 0482687 A1 EP0482687 A1 EP 0482687A1 EP 91202510 A EP91202510 A EP 91202510A EP 91202510 A EP91202510 A EP 91202510A EP 0482687 A1 EP0482687 A1 EP 0482687A1
Authority
EP
European Patent Office
Prior art keywords
composition
weight
salt
internal olefin
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.)
Granted
Application number
EP91202510A
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English (en)
French (fr)
Other versions
EP0482687B1 (de
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
Original Assignee
Shell Internationale Research Maatschappij BV
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Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of EP0482687A1 publication Critical patent/EP0482687A1/de
Application granted granted Critical
Publication of EP0482687B1 publication Critical patent/EP0482687B1/de
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 R1, R2, R3 and R4 independently are linear or branched alkyl groups or hydrogen and the total carbon number of R1, R2, R3 and R4 is from 6 to 24, and wherein at least one of R1 and R2 and one of R3 and R4 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 C1 to C6 mono-alkylether of mono- or di-ethylene glycol, a linear or branched C1 to C6 mono-alkylether of mono- or di-propylene glycol, or a mixture thereof.
  • nonionic surfactants are C7 to C18-alcohols that are alkoxylated with ethylene oxide and/or propylene oxide with a minimum degree of alkoxylation of 2.
  • nonionic surfactants are C6 to C12-alkylphenols, alkoxylated with ethylene oxide and/or propylene oxide with a minimum degree of alkoxylation of 2.
  • nonionic surfactants are hydrophilic C8 to C18-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 C8 to C18-alcoholalkoxy carboxylate salt with a degree of alkoxylation of 1 to 10, or C6 to C10 aliphatic or aromatic sulphonates.
  • a preferred composition according to the invention comprises from 60 to 90% by weight of component a), from 8 to 38% by weight of water and from 2 to 32% by weight of component c).
  • 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.
  • the product mixture exited continuously into a continuous laminar tubular hydrolysis reactor that was heated externally with oil having a temperature of 170-190 °C, the reactor being provided with a preheater section heated with steam at 6 bar, a cooler, and a constant pressure valve; the volume of the hydrolysis reactor was about 40 litres from which the average residence time for each specific product could be estimated.
  • the product flowing out of the constant pressure valve was analysed and, if necessary, adjustments were made in, for instance, the SO3/olefin ratio, the feed rate of concentrated sodium hydroxide solution, water, etc. on the basis of these analyses. After these adjustments sufficient time was allowed to obtain representative samples which were then collected and analyzed.
  • the specific reaction conditions and analytical data of the products are given in the Table.
  • 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)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP91202510A 1990-10-26 1991-09-26 Konzentrierte, flüssige, fliessfähige Zusammensetzung Expired - Lifetime EP0482687B1 (de)

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 true EP0482687A1 (de) 1992-04-29
EP0482687B1 EP0482687B1 (de) 1996-06-12

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Country Status (3)

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

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2186783A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Herstellung von Olefinen
EP2186785A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Trennung von Olefinen und Paraffinen
EP2186784A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Herstellung und von Rückgewinnung von Olefinen
EP2261298A1 (de) 2009-06-10 2010-12-15 Shell Internationale Research Maatschappij B.V. Verfahren zur erhöhten Kohlenwasserstoffrückgewinnung
WO2012163852A1 (en) 2011-05-27 2012-12-06 Shell Internationale Research Maatschappij B.V. Composition and method for enhanced hydrocarbon recovery
US8403044B2 (en) 2009-05-05 2013-03-26 Stepan Company Sulfonated internal olefin surfactant for enhanced oil recovery
WO2013167646A1 (en) 2012-05-09 2013-11-14 Shell Internationale Research Maatschappij B.V. Method for enhanced hydrocarbon recovery
JP2014076988A (ja) * 2012-09-20 2014-05-01 Kao Corp 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
JP2014167106A (ja) * 2013-02-01 2014-09-11 Kao Corp 内部オレフィンスルホン酸塩組成物
JP2014167107A (ja) * 2013-02-01 2014-09-11 Kao Corp 内部オレフィンスルホン酸塩組成物
WO2014137974A1 (en) * 2013-03-06 2014-09-12 Shell Oil Company Internal olefin sulfonate composition
WO2015141699A1 (en) * 2014-03-19 2015-09-24 L'oreal Foaming composition containing internal olefin sulfonates and one foam-enhancing agent or foam booster
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
EP2952567A4 (de) * 2013-02-01 2016-09-07 Kao Corp Interne olefinsulfonatzusammensetzung
EP3162872A1 (de) * 2016-06-24 2017-05-03 Shell Internationale Research Maatschappij B.V. Interne olefinsulfonatzusammensetzung und verwendung davon bei verbesserter ölgewinnung
JP2017214568A (ja) * 2016-05-31 2017-12-07 花王株式会社 繊維製品用液体洗浄剤組成物
JP2017214567A (ja) * 2016-05-31 2017-12-07 花王株式会社 繊維用洗浄剤組成物
WO2018030328A1 (ja) * 2016-08-09 2018-02-15 花王株式会社 界面活性剤組成物
WO2018123942A1 (ja) * 2016-12-26 2018-07-05 花王株式会社 繊維製品の処理方法
CN109154129A (zh) * 2016-05-31 2019-01-04 花王株式会社 衣物的清洁方法
CN109196081A (zh) * 2016-05-31 2019-01-11 花王株式会社 纤维制品用清洁剂组合物
EP3467082A4 (de) * 2016-05-31 2019-12-18 Kao Corporation Flüssige waschmittelzusammensetzung für textilprodukte
US10815164B2 (en) 2015-10-19 2020-10-27 Shell Oil Company Process for producing styrene
US11584881B2 (en) * 2017-06-30 2023-02-21 Dow Global Technologies Llc Low-temperature stabilized surfactant blend for enhanced oil recovery

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4309317A (en) * 1979-02-20 1982-01-05 Lion Corporation Clear aqueous olefin sulfonate solution
US4715991A (en) * 1985-04-26 1987-12-29 Lion Corporation Aqueous high concentration surfactant slurry containing an olefin sulfonate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8817293D0 (en) * 1988-07-20 1988-08-24 Shell Int Research Process for preparation of internal olefin sulphonates

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4309317A (en) * 1979-02-20 1982-01-05 Lion Corporation Clear aqueous olefin sulfonate solution
US4715991A (en) * 1985-04-26 1987-12-29 Lion Corporation Aqueous high concentration surfactant slurry containing an olefin sulfonate

Cited By (53)

* 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
EP2261298A1 (de) 2009-06-10 2010-12-15 Shell Internationale Research Maatschappij B.V. Verfahren zur erhöhten Kohlenwasserstoffrückgewinnung
EP2186783A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Herstellung von Olefinen
EP2186785A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Trennung von Olefinen und Paraffinen
EP2186784A2 (de) 2010-01-27 2010-05-19 Shell Internationale Research Maatschappij B.V. Verfahren zur Herstellung und von Rückgewinnung von Olefinen
WO2012163852A1 (en) 2011-05-27 2012-12-06 Shell Internationale Research Maatschappij B.V. Composition and method for enhanced hydrocarbon recovery
US10000688B2 (en) 2011-05-27 2018-06-19 Shell Oil Company Composition and method for enhanced hydrocarbon recovery
WO2013167646A1 (en) 2012-05-09 2013-11-14 Shell Internationale Research Maatschappij B.V. Method for enhanced hydrocarbon recovery
US20150129227A1 (en) * 2012-05-09 2015-05-14 Julian Richard BARNES Method for enhanced hydrocarbon recovery
US10030194B2 (en) * 2012-05-09 2018-07-24 Shell Oil Company Method for enhanced hydrocarbon recovery
JP2014076988A (ja) * 2012-09-20 2014-05-01 Kao Corp 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
EP3741834A1 (de) * 2013-02-01 2020-11-25 Kao Corporation Interne olefinsulfonatzusammensetzung
US9861566B2 (en) 2013-02-01 2018-01-09 Kao Corporation Internal olefin sulfonate composition
CN104955933A (zh) * 2013-02-01 2015-09-30 花王株式会社 内部烯烃磺酸盐组合物
JP2014167107A (ja) * 2013-02-01 2014-09-11 Kao Corp 内部オレフィンスルホン酸塩組成物
US10328008B2 (en) 2013-02-01 2019-06-25 Kao Corporation Internal olefin sulfonate composition
JP2014167106A (ja) * 2013-02-01 2014-09-11 Kao Corp 内部オレフィンスルホン酸塩組成物
EP2952566A4 (de) * 2013-02-01 2016-09-07 Kao Corp Interne olefinsulfonatzusammensetzung
EP2952567A4 (de) * 2013-02-01 2016-09-07 Kao Corp Interne olefinsulfonatzusammensetzung
EP2952568A4 (de) * 2013-02-01 2016-10-26 Kao Corp Interne olefinsulfonatzusammensetzung
US9861567B2 (en) 2013-02-01 2018-01-09 Kao Corporation Internal olefin sulfonate composition
US9789045B2 (en) 2013-02-01 2017-10-17 Kao Corporation Internal olefin sulfonate composition
CN105026514A (zh) * 2013-03-06 2015-11-04 国际壳牌研究有限公司 内烯烃磺酸盐组合物
US10184076B2 (en) 2013-03-06 2019-01-22 Shell Oil Company Internal olefin sulfonate composition
WO2014137974A1 (en) * 2013-03-06 2014-09-12 Shell Oil Company Internal olefin sulfonate composition
WO2015141699A1 (en) * 2014-03-19 2015-09-24 L'oreal Foaming composition containing internal olefin sulfonates and one foam-enhancing agent or foam booster
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
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
US10815164B2 (en) 2015-10-19 2020-10-27 Shell Oil Company Process for producing styrene
US10947479B2 (en) 2016-05-31 2021-03-16 Kao Corporation Method for washing clothing
RU2747642C2 (ru) * 2016-05-31 2021-05-11 Као Корпорейшн Детергентная композиция для текстильных продуктов
CN109196081A (zh) * 2016-05-31 2019-01-11 花王株式会社 纤维制品用清洁剂组合物
US11248195B2 (en) 2016-05-31 2022-02-15 Kao Corporation Liquid detergent composition for textile products comprising an internal olefin sulfonate/organic solvent mixture
US11124743B2 (en) 2016-05-31 2021-09-21 Kao Corporation Liquid detergent composition for textile products
JP2017214568A (ja) * 2016-05-31 2017-12-07 花王株式会社 繊維製品用液体洗浄剤組成物
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DE69120205T2 (de) 1997-02-06
GB9023366D0 (en) 1990-12-05
DE69120205D1 (de) 1996-07-18
EP0482687B1 (de) 1996-06-12

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