WO2014072840A1 - Sulfates d'alkyle gras aqueux hautement actifs fluides - Google Patents

Sulfates d'alkyle gras aqueux hautement actifs fluides Download PDF

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Publication number
WO2014072840A1
WO2014072840A1 PCT/IB2013/052211 IB2013052211W WO2014072840A1 WO 2014072840 A1 WO2014072840 A1 WO 2014072840A1 IB 2013052211 W IB2013052211 W IB 2013052211W WO 2014072840 A1 WO2014072840 A1 WO 2014072840A1
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WIPO (PCT)
Prior art keywords
fatty alkyl
fatty
flowable
ethoxylated
alkyl sulfates
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PCT/IB2013/052211
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English (en)
Inventor
Ramakrishnan GOPALAKRISHNAN
Shekhar UNNATHAN
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Galaxy Surfactants Ltd.
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Publication date
Application filed by Galaxy Surfactants Ltd. filed Critical Galaxy Surfactants Ltd.
Publication of WO2014072840A1 publication Critical patent/WO2014072840A1/fr

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups

Definitions

  • the present invention relates to highly concentrated, aqueous solutions of fatty alkyl sulfates which are homogeneous, flowable, and pumpable at room temperature. It particularly relates to a process for preparing homogeneous, flowable, and pumpable aqueous solutions of fatty alkyl sulfates with an active ingredient content of atleast 65% by weight.
  • Fatty Alkyl Sulphates are widely used class of anionic surfactants. They are suitable for numerous commercial applications by virtue of their excellent foaming properties and their cleaning effect. They are used in household cleaning products, personal care products, institutional cleaners and industrial cleaning processes, as industrial process aids in emulsion polymerisation and as additives during plastics and paint production. Uses in household cleaning products include laundry detergents, hand dishwashing liquids, and various hard surface cleaners. Their neutral flavor, their acceptable compatibility with mucous membrane, and their growth-inhibition effect on the bacteria responsible for plaque also make them particularly suitable for use as a surfactant component in the production of oral hygiene and dental care preparations.
  • the fatty alkyl sulfates are produced industrially, generally by sulfation of suitable fatty alcohols with gaseous SO 3.
  • the fatty alkyl sulfuric acid which forms as crude product in the process is then neutralized in the presence of suitable alkalis, preferably aqueous sodium hydroxide, to give the fatty alkyl sulfates.
  • suitable alkalis preferably aqueous sodium hydroxide
  • surfactant-containing aqueous preparations with a maximum of 30% by weight of fatty alkyl sulfates are obtained.
  • the demerit associated with such low-concentration FAS solution is its transportation; in so doing only small amounts of active substance (maximum 30% by weight) but large amounts of water are transported.
  • aqueous FAS require antimicrobial agents or preservatives to be added to protect it from microbial contamination.
  • One of the ways to overcome the high transportation cost and other problems associated in using low-concentration FAS is to prepare aqueous solutions of FAS with high concentration having minimum amount of water in it.
  • the smooth production and processing of aqueous FAS with high active ingredient content is often hindered by the fact that these solutions are very viscous and not flowable.
  • Aqueous compositions of FAS are generally easily flowable at room temperature up to an active ingredient content of about 30% by weight and display viscosities of up to 500 mPa.s (by Brookfield Viscometer).
  • compositions of FAS with an active ingredient content of more than 30% by weight are temperature dependent, so that these compositions can be made to flow by heating, for example sodium lauryl sulfate with 70% active content is flowable at about 45°C.
  • heating of such compositions is associated with many problems such as heating containers are not universally available, lots of energy is being utilized for heating, providing heating system to the material during transportation is a cumbersome task, and moreover, heating results in decomposition of the product.
  • aqueous fatty alkyl sulphate solutions which are highly concentrated having atleast 65% by weight of active ingredient and yet homogeneous, flowable and pumpable at room temperature can be prepared by slightly modifying the fatty alkyl sulfates to convert some minor portion of it into ethoxylated fatty alkyl sulfates. This modification is done by direct and simple ethoxylation of fatty alcohols with very low moles of ethylene oxide followed by sulfation with certain reaction conditions and then neutralizing it with a base.
  • US Pat No. 6,313,085 (Cognis) teaches to prepare high-concentration flowable aqueous anionic surfactant mixture having solids content in the range from 50 to 80% by weight, comprising 60-90% by weight of alkyl ether sulphates and 10-40% by weight of alkyl sulphates. These are prepared by sulphating the mixture of fatty alcohol and ethoxylated fatty alcohol.
  • US Pat. No. 5,847,183 (Henkel) relates to high-concentration fatty alcohol (ether) sulfates which are obtained by co-sulfating mixtures of fatty alcohol and fatty alcohol ethoxylate. The claimed product is flowable at room temperature.
  • fatty alkyl (ether) sulfates of comparable carbon chain length and degree of ethoxylation prepared by simple and direct ethoxylation of fatty alcohols followed by sulfation are present as cutting-resistant crystallized pastes which are non-flowable and pumpable.
  • fatty alkyl sulfates having concentration of atleast 65% by weight of active ingredient can be made which are homogeneous, flowable and pumpable even at room temperature by simple and direct ethoxylation of fatty alcohols with very low of about 0.3 to 0.8 moles of ethylene oxide, followed by sulfation of the ethoxylated fatty alcohols with certain unique reaction conditions and then neutralizing the sulfated product with a base.
  • the present invention relates to a process for preparing fatty alkyl sulfate aqueous solutions having active ingredient content of atleast 65% by weight and which is homogeneous, flowable and pumpable at room temperature i.e. 25°C.
  • fatty alkyl sulfate aqueous solutions are prepared by (i) ethoxylation of fatty alcohol with very low of about 0.3 to about 0.8 moles of ethylene oxide (EO), and
  • fatty alkyl sulfates which is a mixture of fatty alkyl sulfates and fatty alkyl ether sulfates present in a weight ratio in the range from about 80:20 to 50:50.
  • the process of the present invention provides fatty alkyl sulfate solution containing very low level of dioxane impurity which has never been achieved before in the prior art. It contains less than 3 ppm of dioxane, more preferably less than 2 ppm of dioxane.
  • the fatty alkyl sulfates are produced industrially, generally by sulfation of suitable fatty alcohols with gaseous SO 3.
  • Inventors of the present invention have found that by slightly ethoxylating the fatty alcohol followed by sulfating the ethoxylated fatty alcohols with SO 3 in a certain reaction conditions, allows to produce fatty alkyl sulfates which are highly concentrated and flowable at room temperature i.e. at about 25°C.
  • the present invention relates to a process for preparing highly concentrated fatty alkyl sulfate aqueous solutions which are homogeneous, flowable and pumpable at 25°C.
  • These fatty alkyl sulfate aqueous solutions are prepared by (i) ethoxylation of fatty alcohol with very low of about 0.3 to 0.8 moles of ethylene oxide to produce ethoxylated fatty alcohol of formula (I) as per (eq.l)
  • R is a linear saturated hydrocarbon radical containing 8 to 18 carbon atoms, and n is an average number of EO moles between 0.3 to 0.8, and
  • mole concentration of S0 3 in S0 3 /air mixture is from about 3.5 to 4.5%, and mole ratio of S0 3 to ethoxylated fatty alcohol is from about 1 :1 to 1: 1.1, and
  • the aqueous fatty alkyl sulfates of the present invention is also a mixture of fatty alkyl sulfates and fatty alkyl ether sulfates.
  • Fatty alkyl ether sulfates are the fatty alkyl sulfates ethoxylated with certain number of moles of ethylene oxides.
  • the fatty alkyl sulfates and fatty alkyl ether sulfates are present in a weight ratio in the range from 80:20 to 50:50. Such high amount of fatty alkyl sulfates in such type of mixtures was never achieved before.
  • the active ingredient concentration of the flowable fatty alkyl sulfate solution obtained by the present inventive process is atleast 65% by weight, preferably atleast 68% by weight, and more preferably atleast 70% by weight. Since the aqueous fatty alkyl sulfates of the present invention is a mixture of fatty alkyl sulfates and fatty alkyl ether sulfates, the said active ingredient concentration is the sum of the concentration of both the said sulfates together.
  • the range of the active ingredient concentration is between 65% to 80% by weight, preferably between 68% to 75% by weight.
  • the fatty alkyl sulfates of the present invention have a fatty alkyl chain containing 8 to 18 carbon atoms.
  • the fatty alkyl chain contains 12 to 18 carbon atoms, more particularly 12 to 16 carbon atoms, and still more particularly 12 to 14 carbon atoms.
  • Typical examples of fatty alkyl chain include, caprylyl, capryl, lauryl, myristyl, cetyl, palmityl, stearyl, and the technical mixtures thereof obtained.
  • Preferred examples are lauryl and coco fatty alkyl chain.
  • the aqueous fatty alkyl sulfates obtained by the process of the present invention also contains certain impurities.
  • the impurities mainly found in fatty alcohol (ether) sulfate products are unsulfated fatty (ether) alcohols and 1,4-dioxane.
  • the process of the present invention provides fatty alkyl sulfate solution containing very low level of dioxane impurity which has never been achieved before in the prior art. It contains less than 3 ppm of dioxane, more preferably less than 2 ppm of dioxane.
  • 1,4-dioxane is the most undesirable by-product or impurity formed during the sulfation of ethoxylated alcohols is 1,4-dioxane.
  • 1,4-Dioxane (CAS No. 123-91-1) was declared a Priority Existing Chemical on 3rd May 1994 due to concerns over possible human carcinogenicity, its potential for widespread occupational and public exposure and high degree of partitioning to, and persistence in the aquatic environment.
  • the health risk from 1 ,4-dioxane in laundry detergents has become a matter of considerable debate among public health experts and advocates.
  • the same study group has also tested many other cosmetic and personal care products, as well as other types of household cleaning products for the presence of this chemical.
  • mole concentration of SO j in air sulfating the ethoxylated fatty alcohol with 3.5 to 4.5% mole concentration of SO 3 in air provides a good quality sulfated product. Mole concentration lower than 3.5%, results in decrease in the rate of reaction and the reaction does not complete. If the mole concentration of SO 3 in air is higher than 4.5% then the rate of reaction will be too high, resulting into over-sulfation and leading to high colouration of the product and also the level of impurities including dioxane will increase.
  • sulfating reaction temperature sulfating the ethoxylated fatty alcohol at a temperature from about 40°C to 50°C is required to get a proper sulfated product. Temperature lower than 40°C increases the condensation of SO 3 into droplets which leads to incompletion of reaction, whereas reaction temperature higher than 50°C results to over-sulfation and leading to high colouration of the product and also the level of impurities including dioxane increases.
  • mole ratio of SO ⁇ ethoxylated fatty alcohol mole ratio of SO 3 to ethoxylated fatty alcohol of from about 1: 1 to 1: 1.1 is required to maintain the colour and impurity level within the acceptable limit. Below 1: 1 ratio, the sulfation reaction does not complete and results in lower yields, whereas ratio above 1:1.1 results into high colouration of the product and also the level of impurities including dioxane increases.
  • fatty alkyl sulfate solutions containing very low amount of dioxane. It contains less than 3 ppm of dioxane, preferably less than 2 ppm which ultimately provides a ultra low or trace amount of dioxane in the final shampoo, body wash or other personal and home care cleansing formulations.
  • Ultra low or trace amount means less than 0.5 ppm of dioxane, preferably less than 0.3 ppm of dioxane and more preferably less than 0.2 ppm of dioxane.
  • Such low quantity of dioxane in personal care and home care cleansing formulations is unexpectedly obtained due to the use of aqueous fatty alkyl sulfates which is produced by the process of the present invention.
  • Another benefit of present invention is that the high-concentration, flowable aqueous fatty alkyl sulfate solution obtained does not require any antimicrobial system and is self- preserving due to its high active and high solids content.
  • the present invention relates to a process for preparing an aqueous solution of fatty alkyl sulfates, the solution comprising
  • solution does not contain any antimicrobial and is homogeneous, flowable and pumpable at 25°C.
  • the pH of the fatty alkyl sulfate solution obtained by the present invention is between 6 to 9.
  • novel process to obtain the novel fatty alkyl sulfates of the present invention can be better understood by the following examples.
  • Examples 1, 2, 3, 4 and 5 describe the process of manufacture of novel highly concentrated, flowable fatty alkyl sulfates ethoxylated with 0.3 to 0.8 moles of EO.
  • Examples 6 to 11 illustrates the comparative examples.
  • Examples 12 and 13 describes the preparation of personal care formulations (e.g. shampoo) incorporating the novel compounds of the present invention.
  • Example 1 0.5 mole ethoxylated sodium lauryl (C 12 -14) sulfate
  • the sulfated mass was then continuously fed to the vacuumed wiped film neutraliser where it was neutralised with 22% sodium hydroxide aqueous solution. Vacuum of the neutralizer was maintained in the range of 0.925 - 0.945 kg/cm". The pH of the solution was adjusted in the range of 6-7 by adding acid.
  • the resultant 0.5 mole ethoxylated sodium lauryl sulfate solution contained sodium lauryl sulfate and sodium lauryl ether sulfate in a weight ratio of about 73:27 and the combined or total active ingredient content was 70-72% by weight.
  • the product obtained was homogeneous, flowable and pumpable at 25°C, having dioxane content of 1.9 ppm.
  • Example 2 0.3 mole ethoxylated sodium lauryl (C 12 -14) sulfate
  • the resultant 0.3 ethoxylated sodium lauryl sulfate solution contained a mixture sodium lauryl sulfate and sodium lauryl ether sulfate and the combined or total active ingredient content was 70-72% by weight.
  • the product obtained was homogeneous, flowable and pumpable at 25°C, having dioxane content of 0.86 ppm.
  • Example 3 0.8 mole ethoxylated sodium lauryl (C12-14) sulfate
  • the sulfated mass was continuously fed to the vacuumed wiped film neutraliser where it was neutralised with 22% sodium hydroxide aqueous solution. Vacuum of the neutralizer was maintained in the range of 0.925 - 0.945 kg/cm". The pH of the solution was adjusted in the range of 6-7 by adding acid.
  • the resultant 0.8 ethoxylated sodium lauryl sulfate solution contained a mixture sodium lauryl sulfate and sodium lauryl ether sulfate in a weight ratio of about 50:50 and the combined or total active ingredient content was 70-72% by weight.
  • the product obtained was homogeneous, flowable and pumpable at 25°C, having dioxane content of 2.1 ppm.
  • Example 4 0.5 mole ethoxylated sodium lauryl (Cs-is) sulfate
  • the total active ingredient content was 69- 71% by weight.
  • the product obtained was homogeneous, flowable and pumpable at 25°C, having dioxane content of 2.0 ppm.
  • the total active ingredient content was 68- 70% by weight.
  • the product obtained was homogeneous, flowable and pumpable at 25°C, having dioxane content of about 1.9 ppm.
  • Example 6 Preparation of 0.5 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using mole concentration of 5% of SO 3 in air.
  • Example 7 Preparation of 0.5 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using mole concentration of 3% of SO 3 in air.
  • Example 8 Preparation of 0.3 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using sulfation temperature of 55°C
  • Example 9 Preparation of 0.3 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using sulfation temperature of 35°C
  • Example 10 Preparation of 0.8 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using mole ratio of SO 3 to ethoxylated fatty alcohol of 1 : 1.5
  • Example 11 Preparation of 0.8 mole ethoxylated sodium lauryl (C 12-14 ) sulfate using mole ratio of SO 3 to ethoxylated fatty alcohol of 1:0.5 It was seen that the flowability of all the products were hampered and some of them become non-flowable also. The dioxane content of all the products was too high, of about more than 10 ppm. Also, some products were found to be discoloured.
  • Example 12 Shampoo formulation containing 0.5 mole ethoxylated sodium lauryl (C12- 14) sulfate of example 1
  • the dioxane content was detected to be 0.26 ppm based on the total formulation.
  • Example 13 Shampoo formulation containing 0.3 mole ethoxylated sodium lauryl (C12- 14) sulfate of example 2
  • the dioxane content was detected to be 0.12 ppm based on the total formulation.

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Abstract

La présente invention porte sur un procédé pour la préparation d'une solution aqueuse fluide de sulfates d'alkyle gras à haute concentration, ledit procédé comprenant (i) l'éthoxylation d'un alcool gras avec une très faible quantité d'oxyde d'éthylène d'environ 0,3 à environ 0,8 mole, (ii) la sulfatation de l'alcool gras éthoxylé dans des conditions de réaction particulières et (iii) la neutralisation du produit de sulfatation avec une base aqueuse. La solution de sulfates d'alkyle gras obtenue contient au moins 65 % en poids de mélange de sulfates d'alkyle gras et d'alkyléthersulfates gras en une proportion en poids dans la plage d'environ 80:20 à environ 50:50, le nombre moyen de moles d'oxyde d'éthylène (OE) du mélange étant compris entre 0,3 et 0,8; moins de 3 ppm de dioxane; et de l'eau; la solution ne contenant pas de quelconque agent antimicrobien ou conservateurs et étant homogène, fluide et pompable à 2°C.
PCT/IB2013/052211 2012-11-12 2013-03-20 Sulfates d'alkyle gras aqueux hautement actifs fluides WO2014072840A1 (fr)

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Cited By (7)

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CN104341323A (zh) * 2014-10-30 2015-02-11 中国日用化学工业研究院 一种壬基酚聚氧乙烯醚硫酸盐表面活性剂的生产工艺
CN106380428A (zh) * 2016-08-31 2017-02-08 上海奥威日化有限公司 脂肪醇磺化的方法
CN107602423A (zh) * 2017-08-29 2018-01-19 东明俱进化工有限公司 一种粉末状月桂醇硫酸酯钾盐的生产工艺及其装置
CN109574883A (zh) * 2018-11-29 2019-04-05 四川金桐精细化学有限公司 一种乙氧基化烷基硫酸钠的制备方法
CN112680208A (zh) * 2021-01-06 2021-04-20 中国日用化学研究院有限公司 一种油醇聚氧乙烯醚磺酸盐/硫酸盐的制备工艺
WO2023172859A1 (fr) 2022-03-07 2023-09-14 The Procter & Gamble Company Procédés de fabrication de mélanges de tensioactifs concentrés
EP4249578A1 (fr) 2022-03-07 2023-09-27 The Procter & Gamble Company Procédés de fabrication de mélanges de tensioactifs concentrés

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EP0008060A1 (fr) 1978-08-03 1980-02-20 BASF Aktiengesellschaft Utilisation d'alcools polyvalents, d'acides (hydroxy)carboxyliques et/ou de leurs esters avec des alcools polyvalents comme régulateurs de viscosité
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EP0403148A2 (fr) 1989-06-09 1990-12-19 The Procter & Gamble Company Particules de détergent à haute activité dispersables dans l'eau froide
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EP0603207A1 (fr) 1991-08-20 1994-06-29 Henkel Kgaa Procede de fabrication de granulats tensioactifs.
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DE4339890A1 (de) * 1993-11-23 1995-05-24 Henkel Kgaa Verfahren zur Herstellung wäßriger Lösungen von Ethersulfat-Salzen mit vermindertem Gehalt an 1,4-Dioxan
US5847183A (en) 1995-11-15 1998-12-08 Henkel Corporation Fatty alcohol (ether) sulfates with improved low-temperature behavior
US6780829B1 (en) 1998-12-19 2004-08-24 Cognis Deutschland Gmbh & Co. Kg Tenside granulates comprising fatty alcohol sulfate and olefin sulfonates
US6313085B1 (en) 1999-06-29 2001-11-06 Cognis Deutschland Gmbh High-concentration flowable anionic surfactant mixtures containing alkyl ether sulfates and alkyl sulfates
JP2007131573A (ja) 2005-11-10 2007-05-31 Lion Corp ポリオキシエチレンアルキルエーテル硫酸塩の製造方法
US20100303739A1 (en) 2007-09-14 2010-12-02 Cognis Ip Management Gmbh Highly Concentrated Fatty Alcohol Sulfate Preparation

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Cited By (8)

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CN106380428A (zh) * 2016-08-31 2017-02-08 上海奥威日化有限公司 脂肪醇磺化的方法
CN106380428B (zh) * 2016-08-31 2017-11-03 上海奥威日化有限公司 脂肪醇磺化的方法
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CN112680208A (zh) * 2021-01-06 2021-04-20 中国日用化学研究院有限公司 一种油醇聚氧乙烯醚磺酸盐/硫酸盐的制备工艺
WO2023172859A1 (fr) 2022-03-07 2023-09-14 The Procter & Gamble Company Procédés de fabrication de mélanges de tensioactifs concentrés
EP4249578A1 (fr) 2022-03-07 2023-09-27 The Procter & Gamble Company Procédés de fabrication de mélanges de tensioactifs concentrés

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