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GB2185488A - Alkoxylated decanol sulphate surfactants and their use in shampoo compositions - Google Patents

Alkoxylated decanol sulphate surfactants and their use in shampoo compositions Download PDF

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Publication number
GB2185488A
GB2185488A GB08700608A GB8700608A GB2185488A GB 2185488 A GB2185488 A GB 2185488A GB 08700608 A GB08700608 A GB 08700608A GB 8700608 A GB8700608 A GB 8700608A GB 2185488 A GB2185488 A GB 2185488A
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Prior art keywords
mixture
oc3h6
oc2h4
formula
integer
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GB08700608A
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GB8700608D0 (en
GB2185488B (en
Inventor
Robert V Casciani
Anthony Latella
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Sandoz AG
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Sandoz AG
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    • 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
    • A61K8/90—Block copolymers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Polyethers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to novel poly-ether sulphates based on a mixture of branched 1-decanols and to their use as surface active agents. The novel poly-ether sulphates are especially useful as the essential surfactant component in shampoo compositions, which compositions exhibit good foaming properties with little or no irritation potential.

Description

SPECIFICATION Improvements in or relating to organic compounds This invention relates to novel surface active agents particularly useful as surfactants in shampoo compositions.
The invention provides a mixture of compounds of formula I R(OC3H6)m (OC2H4)nOSO3M (I) wherein R is the residue of a mixture of primary, aliphatic alcohols, at least 70 mol % of which is branched 1-decanols, the remaining components consisting essentially of primary, aliphatic alco hols having an average of 8 to 12 carbon atoms; m is an integer from 2 to 13; n is an integer from 6 to 15; and M is a cation.
R is preferably R', where R' is the residue of a mixture of primary, aliphatic alcohols, at least 90 mol YO of which is branched 1-decanols. More preferably, R is R" where R" is the residue of a mixture of primary, aliphatic alcohols, at least 95 mol % of which is branched 1-decanols.
Even more preferably, R is R"' where R"' is the residue of a mixture of primary, aliphatic alcohols, at least 95 mol % of which is branched 1-decanols and the major isomers are trimethyl- 1 -heptanols.
The variable, m, is preferably m' where m' is 3 to 12, more preferably m" where m" is 3 to 10, and most preferably m"' where m"' is 3 to 9.
The variable, n, is preferably n' where n' is 6 to 13, more preferably n" where n" is 6 to 12, and most preferably n"' where n"' is 8 to 12.
M is preferably M' where M' is a cation selected from alkali metal, alkaline earth metal, ammonium, mono-, di- and tri-C2 4alkanolammonium, mono-, di-, tri- and tetra-C14alkylammon- ium, pyridinium and morpholinium. More preferably, M is M" where M" is a cation selected from sodium, potassium, ammonium, mono-, di- and tri-C2 4-alkanolammonium and mono-, di-, tri-and tetra-C, 4alkylammonium. Even more preferably, M is M"' where M"' is a cation selected from sodium, potassium, ammonium and mono-, di- and tri-C2 4aikanolammonium.
Preferred mixtures of compounds are those of formula la R'(OC3H6)m'(OC2H4)'OSO3M' (la) wherein R', m', n' and M' are defined above.
The more preferred mixtures of compounds are those of formula Ib: R"(0C3H6)rn(0C2H4)n"OSO3M" (Ib) wherein R", m", n" and M" are defined above.
The most preferred mixtures of compounds are those of formula Ic: R"'(OC3H6)m..(0C2H4)n.. OSO3M"' (Ic) wherein R"', m"', n"' and M"' are defined above.
The compounds of formula I may be produced by conventional methods. Thus, the novel ether sulphates of this invention may be prepared by sulphating the adduct resulting from the propoxy lation and ethoxylation of a specific mixture of primary, aliphatic alcohols as defined above with a conventional sulphating agent in a manner conventional for the sulphation of similar primary alcohols.
The alkoxylation step is preferably carried out in the presence of a conventional catalyst, for example an alkali metal hydroxide or alkaline earth metal oxide.
Optionally a small amount of a reducing agent, for example sodium borohydride, may be added to the alcohol mixture to reduce discolouration during the alkoxylation reaction.
An amount of propylene oxide calculated to provide the desired degree of propoxylation is introduced and the resulting mixture is allowed to react until the propylene oxide is consumed, as indicated by the reaction pressure no longer decreasing with time. A similar introduction and reaction of a calculated amount of ethylene oxide serves to provide the second block which completes the alkoxylation. Preferably, the alkoxylated product is finally treated with weak acid, e.g., glacial acetic acid, to neutralize any basic catalyst residues.
It should be understood that each separate alkoxylation procedure serves to introduce a desired average number of alkylene oxide units per alcohol molecule. Thus, for example, the initial treatment of an alcohol mixture with m- moles of propylene oxide per mole of alcohol serves to effect the propoxylation of each alcohol moiety with propylene oxide to an average of m propylene oxide moieties per alcohol moiety, although some alcohol moieties will have become combined with more than m propylene oxide moieties and some will have become combined with less than m. The variation in the number of alkylene oxide moieties is not critical as long as the average for the number of units in each block is within the limits set out for the m and n terms in formula I above, which terms, as average values, are other than whole numbers in some instances.
Each alkoxylation is conducted under conventional conditions of temperature and pressure, and preferably under moisture-free conditions. The resulting alkyl polyalkoxide intermediates are then sulphated employing a conventional sulphating agent such as sulphuric acid, sulphamic acid, sulphur trioxide and chlorosulphonic acid, and utilizing either a batch or continuous process. For purposes of this invention, it has been found most suitable to employ chlorosulphonic acid in a batch process.
Typically, the alkyl polyalkoxide intermediate is introduced into a reaction vessel, purged with nitrogen and heated under vacuum to remove trace water. With stirring, a 10% to 20% molar excess of chlorosulphonic acid is then added, dropwise, and the reaction temperature is maintained between 30O and 35"C until addition is complete. After allowing the reaction to proceed for 11/2 to 2 hours, the resultant mixture is then poured onto cracked ice and the pH adjusted to between 6.5 to 7.5 with sodium hydroxide.
The compounds of formula I are useful as surface active agents, for example as emulsifiers, dispersing agents, detergents, wetting agents, levelling agents and the like in the textile, leather, paper, lacquer, toiletries, cosmetics, and rubber industries. For instance, they can be used as wetting agents or detergents in the treating and refining of textiles; and for converting liquid or solid substances which are insoluble in water (such as hydrocarbons, higher alcohols, oils, fats, waxes and resins) into creamy emulsions, clear solutions or fine, stable dispersions.
In addition, the compounds of formula I are valuable emulsifiers for insecticide compositions and agricultural sprays; are valuable for use as additives to petroleum products, hydraulic fluids, lubricating oils, cutting oils and greases; may be employed as coating aids for use in coating compositions comprising a hydrophilic, film-forming colloid; may be employed as tackifiers in the adhesive layer of adhesive tapes in, e.g., the photographic industry; and as foaming agents and emulsifying agents in a wide variety of food products.
The ether sulphates of the present invention are especially useful as the essential surfactant component in hair shampoo compositions. Their incorporation serves not only to enhance the detergency and foaming properties of the shampoo compositions but also to reduce their irritation potential, giving extremely mild shampoo compositions, which also have good tactile properties. Such shampoo compositions will normally contain from about 5% to about 50% of an ether sulphate mixture of formula I, preferably from about 5% to about 40%, and more preferably from about 10% to about 30%.As indicated above, the ether sulphates may be employed as the sole surfactant in the composition, totally replacing the conventional surfactants such as aikyl-EO sulphates, which is the more preferred embodiment of the instant invention, or the ether sulphates may be employed in combination with conventional surfactants, only partially replacing the latter.
The shampoo compositions can contain other ingredients commonly found in such compositions. For example, a fatty alkanolamide, or a mixture thereof, may be employed to assist in foam stabilization, foam boosting and in providing a cosmetically acceptable viscosity. In general, a C8 ,8 mono- or dialkanolamide of the 1:1 variety (prepared by reacting equimolar amounts of the methyl ester of an appropriate carboxylic acid and mono- or dialkanolamine) is employed. A suitable example of a monoalkanolamide is cocomonoethanolamide, and typical examples of suitable dialkanolamides are lauric diethanolamide and cocodiethanolamide.
Conditioners may also be employed and such may be quaternary ammonium compounds such as dimethyl distearyi ammonium chloride and cationic polymers such as Cartaretin F-23 (Sandoz Corporation) and Polymer JR (Union Carbide). These materials are utilized to improve the combability and manageability of damaged hair and to reduce static build-up on dry hair.
In order to improve the sheen of the hair, an oil may be present in the shampoo compositions. Such may be a silicone oil such as dimethylpolysiloxane or other conventional polysiloxanes, olive oil, or a light mineral oii.
The amount of water or aqueous vehicle to be included depends upon the desired consistency of the final product. It is possible to vary the amount of water present to formulate, for example, a thick-flowing liquid, lotion or gel. Inorganic salts such as sodium chloride can also be employed to control the viscosity.
Other conventional additives typically employed in shampoo compositions may be utilized.
Fragrance oils, which mask the odor and provide cosmetic appeal, can be employed. Non-toxic and compatible dyes may be utilized to color the compositions, as desired. Preservatives, such as methyl paraben, propyl paraben and formaldehydes may be utilized.
In addition, other ingredients can be employed beneficially to provide shampoo compositions tailored to a specific use. For example, a sun screen additive such as octyl dimethyl paraaminobenzoic acid can be employed to provide hair protection. Also, products designed to provide dandruff protection can be formulated with agents such as zinc omadine (Olin).
The following examples, in which all parts are by weight and all temperatures are in "C, illustrate the invention.
EXAMPLE 1 Hexapropoxy-dodecaethoxy isodecyl sulphate, Na salt lsC10H21 (OC3H6)6 (OC2H4)120S03Na a) Preparation of hexapropoxy-dodecaethoxy isodecanol To a reaction vessel are added, with stirring, 327 parts of decyl alcohol (a mixture of primary, aliphatic alcohols, at least 90 mol % of which is branched 1-decanols, having a boiling range of 216 to 223 , a specific gravity at 20/20 of 0.838, a refractive index nD20, of 1.440, a pour point of -53.5", a viscosity at 20 of 22.5 centistokes and a solubility in water at 200 of 0.05 g/100 g, and commercially available from Exxon Chemical Co.), 6.5 parts of potassium hydroxide and 0.21 parts of sodium borohydride.After heating the reaction mixture to 60 under vacuum (66 mbar) the system is purged with nitrogen to atmospheric pressure and the evacuation and purging procedure is repeated two additional times to minimize the presence of air.
Finally, the system is evacuated to 66 mbar pressure then heated with agitation to 155 . While maintaining the reaction temperature at 155 , 720 parts of propylene oxide are slowly added by use of a metering valve from a pressurized cylinder at such a rate that the pressure in the reaction vessel approaches and then is maintained at about atmospheric pressure. When the addition of propylene oxide is complete, the reaction mixture is allowed to post-react until the pressure drops to a point where it remains constant for at least 30 minutes. The system is cooled to 60 where the evacuation and purging procedure is repeated twice. Finally, the system is evacuated to 66 mbar pressure and then 1092 parts of ethylene oxide are added by the procedure described above.After the post-react period, the system is cooled to 1200 and a vacuum of 66 mbar is applied for at least one hour to remove unreacted alkylene oxide. The system is cooled to 600, pressurized with nitrogen to atmospheric pressure and neutralized with about 6.3 parts of acetic acid to yield a translucent pale yellow liquid of the formula iso-C10H21 (OC3H6)6 (OC2H4)12 OH which becomes milky white upon cooling and develops a white precipitate upon standing.
b) Preparation of the title compound 258.8 Parts (0.25 moles) of the alcohol alkoxylate prepared in a) above are added to a 3-neck reaction vessel and the system purged with nitrogen for 10 minutes. The reaction vessel is then evacuated and the alcohol alkoxylate therein is heated to 60 to remove any traces of water.
After cooling to room temperature, 40 parts (0.34 moles) of chlorosulphonic acid are added, with stirring, at a rate such that the reaction temperature remains between 30 and 35 throughout the addition. The reaction mixture is then stirred for an additional 90 minutes, after which time it is poured into ice and the pH adjusted to between 7.0 and 7.5 with a 50% solution of sodium hydroxide. Water is then added in an amount of sufficient to adjust the solids level to between 40% and 45%.
EXAMPLE 2 Following essentially the procedure of Example la) and employing the starting alcohol utilized in Example 1, i.e., the decyl alcohol available commercially from Exxon Chemical Co., and the appropriate amounts of propylene oxide and ethylene oxide, the following compounds are obtained: a) iso-C,0H21 (OC3H6)3 (OC2H4)9 OH b) 15oC10H2 (OC3H6)3 (OC2H4)6 OH c) iso-C10H21 (OC3H6)6 (OC2H4)6 OH; and d) iseC10H21 (OC3H6)9 (OC2H4)9 OH.
EXAMPLE 3 Following essentially the procedure of Example 1(b) and using in place of the compound prepared in 1a), an approximately equivalent amount of compounds 2a) to 2d), there is obtained: a) iseClOH21 (OC3H6)3 (OC2H4)9 OS03 Na b) iso-C,0H2l (OC3H6)3 (OC2H4)6 OS03 Na c) iso-C1OH21 (OC3H6)6 (OC2H4)6 OSO3 Na; and d) iso-C,OH21 (OC3H6)9 (OC2H4)9 OS03 Na, respectively EXAMPLE 4 The following represent typical formulations useful as shampoo compositions.
Percent A B C Example 1 (41.7% act.) 32.0 40.0 Example 3a) (40.7% act.) - - 35.0 lauramide diethanol amine 6.0 2.0 cocoamido hydroxypropyl sultaine (45% act.) - 6.0 dye 0.2 0.2 0.2 perfume 0.2 0.2 0.2 water q.s. q.s. q.s.
Total 100.0 100.0 100.0 pH (adjusted with citric acid or 6.0 6.0 7.0 sodium hydroxide)

Claims (15)

1. A mixture of compounds of formula R(OC3H6)m (OC2H4)n OSO3M (I) wherein R is the residue of a mixture of primary, aliphatic alcohols, at least 70 mol % of which is branched 1-decanols, the remaining components consisting essentially of primary, aliphatic alcohols having an average of 8 to 12 carbon atoms; m is an integer 2 to 13; n is an integer 6 to 15; and M is a cation.
2. A mixture of compounds according to Claim 1 of formula la, R' (OC3H6)m (OC2H4)n OSO3M' (la) wherein R' is the residue of a mixture of primary, aliphatic alcohols, at least 90 mol % of which is branched 1-decanols; m' is an integer 3 to 12; n' is an integer 6 to 13; and M' is a cation selected from alkali metal, alkaline earth metal, ammonium, mono-, di- and tri C2 4alkanolammonium and mono-, di-, tri- and tetra-C14alkylammonium.
3. A mixture of compounds according to Claim 2 of formula Ib, R" (OC3H6)m (OC2H4)n. OSO3M" (Ib) wherein R" is the residue of a mixture of primary, aliphatic alcohols, at least 95 mol % of which is branched 1-decanols; m" is an integer 3 to 10; n" is an integer 6 to 12; and M" is a cation selected from sodium, potassium, ammonium, mono-, di- and tri-C24alkanolam- monium and mono-, di-, tri- and tetra-C1 4alkylammonium.
4. A mixture of compounds according to Claim 3 of formula Ic R"' (OC3H6)m"' (OC2H4)n... OSO3M"' (Ic) wherein R"' is the residue of a mixture of primary, aliphatic alcohols, at least 95 mol % of which is branched 1-decanols and the major isomers are trimethyl-1-hepthanols; m"' is an integer 3 to 9; n"' is an integer 8 to 12; and M"' is a cation selected from sodium, potassium, ammonium and mono-, di- and tri-C2 4alkano- lammonium.
5. A mixture of compounds according to Claim 4 having the formula iso-C,OH21 (OC3H6)6 (OC2H4)120SO3Na.
6. A mixture of compounds according to Claim 4 having the formula iso-C10H21 (OC3H6)3 (OC2H4)9 OSO3Na.
7. A mixture of compounds according to Claim 3 having the formula, iso-C10H21 (OC3H6)3 (OC2H4)6 OSO3Na.
8. A mixture of compounds according to Claim 3 having the formula, iSO-C1OH21 (OC3H6)6 (OC2H4)6 OSO3Na.
9. A mixture of compounds according to Claim 4 having the formula, iso-C 10H21 (OC3H6)9 (OC2H4)9 OSO3Na.
10. A mild shampoo composition comprising, as the essential surfactant component, from 5% to 50% by weight of a mixture of compounds according to Claim 1.
11. A composition according to Claim 10 wherein the essential surfactant component is present in an amount of from 5% to 40% by weight.
12. A composition according to Claim 11 wherein the essential surfactant component is present in an amount of from 10% to 30% by weight.
13. A composition according to Claim 10 wherein the essential surfactant component is a mixture of compounds having the formula, isoC 10H21 (OC3H6)6 (OC2H4)12 OSO3Na.
14. A composition according to Claim 10 wherein the essential surfactant component is a mixture of compounds having the formula, iso-C,OH2, (OC3H6)3 (OC2H4)9 OSO3Na.
15. A shampoo composition as described in any one of Examples 6 A to C.
GB8700608A 1986-01-15 1987-01-12 Alkoxylated aliphatic alcohol sulphates and shampoo compositions containing them Expired GB2185488B (en)

Applications Claiming Priority (1)

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US81918186A 1986-01-15 1986-01-15

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GB2185488A true GB2185488A (en) 1987-07-22
GB2185488B GB2185488B (en) 1989-10-25

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JP (1) JPS62246549A (en)
BE (1) BE1000131A4 (en)
CH (1) CH668266A5 (en)
DE (1) DE3700280A1 (en)
FR (1) FR2593083B1 (en)
GB (1) GB2185488B (en)
IT (1) IT1216779B (en)
NL (1) NL8700035A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012009539A3 (en) * 2010-07-15 2013-05-10 The Procter & Gamble Company Method of cleansing hair
CN115124709A (en) * 2022-06-29 2022-09-30 东营市金美化工有限公司 Polyether demulsifier with decyltetradecanol as starting agent, preparation method and application thereof

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8718886D0 (en) * 1987-08-10 1987-09-16 Ici America Inc Composition
DE10318079A1 (en) * 2003-04-17 2004-10-28 Cognis Deutschland Gmbh & Co. Kg Use of alkoxylated polyol derivatives for treating textiles
DE102004007152A1 (en) * 2004-02-12 2005-08-25 Basf Ag Novel alkyl ether sulfates useful as anionic surfactants in detergents, cleansing or cosmetic compositions or chemical-technical applications have alkylene oxide units between the alcohol component and sulfate group
JP2009221257A (en) * 2008-03-13 2009-10-01 Nippon Shokubai Co Ltd Polyalkylene glycol compound and its use
JP5235101B2 (en) * 2008-06-16 2013-07-10 花王株式会社 Aqueous hair cleanser
JP5571367B2 (en) * 2008-12-25 2014-08-13 花王株式会社 Surfactant composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1445997A (en) * 1973-11-06 1976-08-11 Unilever Ltd Process for sulphating ethoxylated secondary alcohols
US4051047A (en) * 1976-03-24 1977-09-27 Chevron Research Company Group II metal mixed salts of two different organic acids in lubricant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012009539A3 (en) * 2010-07-15 2013-05-10 The Procter & Gamble Company Method of cleansing hair
CN103687583A (en) * 2010-07-15 2014-03-26 宝洁公司 How to clean your hair
US8765651B2 (en) 2010-07-15 2014-07-01 The Procter & Gamble Company Method of cleansing hair
US8883698B2 (en) 2010-07-15 2014-11-11 The Procter & Gamble Co Compositions comprising a near terminal-branched compound and methods of making the same
CN115124709A (en) * 2022-06-29 2022-09-30 东营市金美化工有限公司 Polyether demulsifier with decyltetradecanol as starting agent, preparation method and application thereof

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GB8700608D0 (en) 1987-02-18
DE3700280A1 (en) 1987-07-16
FR2593083A1 (en) 1987-07-24
JPS62246549A (en) 1987-10-27
BE1000131A4 (en) 1988-04-19
GB2185488B (en) 1989-10-25
FR2593083B1 (en) 1988-11-25
CH668266A5 (en) 1988-12-15
IT8747520A0 (en) 1987-01-13
NL8700035A (en) 1987-08-03
IT1216779B (en) 1990-03-14

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