GB2288600A - Polyalkyl ethers based on ethylene and propylene oxides and 2-haloacetates - Google Patents

Polyalkyl ethers based on ethylene and propylene oxides and 2-haloacetates Download PDF

Info

Publication number
GB2288600A
GB2288600A GB9507982A GB9507982A GB2288600A GB 2288600 A GB2288600 A GB 2288600A GB 9507982 A GB9507982 A GB 9507982A GB 9507982 A GB9507982 A GB 9507982A GB 2288600 A GB2288600 A GB 2288600A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
compounds
alkyl
employed
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.)
Withdrawn
Application number
GB9507982A
Other versions
GB9507982D0 (en
Inventor
Umberto Cazzaniga
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.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB9507982D0 publication Critical patent/GB9507982D0/en
Publication of GB2288600A publication Critical patent/GB2288600A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • C09K23/44—Ether carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or 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
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
    • C23C22/60—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using alkaline aqueous solutions with pH greater than 8
    • C23C22/63—Treatment of copper or alloys based thereon
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F1/00—Etching metallic material by chemical means
    • C23F1/10—Etching compositions
    • C23F1/14—Aqueous compositions
    • C23F1/16—Acidic compositions
    • C23F1/18—Acidic compositions for etching copper or alloys thereof

Description

2288600 IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS The invention
relates to surface active agents useful in various applications, e.g. as emollients in cosmetic compositions, especially in skin care compositions and also in personal care products. Such personal care products include shampoos, bath foams and bath showers, where lauryl ether sulphate is used as a soap. However, lauryl ether sulphate (LES) has irritant properties. These are reduced by the use, in combination with LES, of betaines, which themselves are irritants, yet in combination with LES reduce the irritant properties to below that of either component alone. In addition, betaines act as softening agents. Yet the betaines show some disadvantages, for example the presence of reaction salts, the possible presence of undesirable side products and a scanty lime dispersing powder.
It has been found that these disadvantages can be alleviated by using, instead of betaines, the new compounds of formula I below.
According to the invention there is provided a compound of formula I R-O-(P0).-(E0).-CH2-COOR, (I) in which m is 1 to 4; n is 2 to 20 (preferably 3 to 20); R is C,-1,alkyl or C8-, 8alkertyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,-,,alkyl, a cation (for example an alkali metal cation such as NA' or K) and ammonium groups (for example those derived from reacting the acid with triethanolan-iine or monoethanolamine) 2 Case 150-5771 Preferably R, is R,' where R,' is selected from hydrogen, potassium, sodium, lithium, triethanolammonium, monoethanolammonium and C,-,,alkyl.
l Preferably m is 1, 2 or 3, more preferably 1 or 2.
Preferably n is 5 to 11, more preferably 7 to 11, most preferably 7.
It has been found that the compounds of formula 1 are almost totally biodegradable, nonirritant and non-toxic. Further, compounds of formula I can be used in liquid form which makes them easier to formulate.
In particular, it has been found that the higher the amount of EO present, the less irritant properties the compounds of formula I have. In particular, EO levels where n is 7-11 show this interesting effect.
Preferred compounds according to the invention are those of formula Ib R-O-(P0).-(E0).-CH2-COOC,-1,alkyI (Ib) in which R, PO, EO, m and n are as defined above.
Preferred compounds of formula Ib are of the formula Ib' R-O-(P0).-(E0),,.-CH2-CO0C8-1galkyl (Ib') where R, PO, EO and m are as defined above and n' is 7-11.
Further according to the invention there is provided a process for prgparing a detergent composition in which there is used as a detergent, a compound of forinla I R-0-(P0).-(E0)jCH2-COOR, (I) 3 in which Case 150-5771 m is 1 to 4; n is 2 to 20 (preferably 3 to 20); R is C,-1,aIkyl or C,-1, alkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,_1.alkyl, a cation (for example an alkali metal cation such as NA' or K) and ammonium groups (for example those derived from reacting the acid with triethanolamine or monoethanolamine).
Preferably, in the compounds of formula 1 when used as a detergent, R is C, alkyl or C10-14alkyl and n is 5-7.
When compounds of formula I are used as detergents, these can be formulated into creams and milks for cosmetics.
Still further according to the invention there is provided a process for the preparation of an emulsion in which there is used, as an emulsifier, a compound of formula I R-O-(P0).-(EO),-CH2-COOR, (I) in which m is 1 to 4; n is 2 to 20 (preferably 3 to 20); R isC8-1,alkyl or C,-1, alkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,-,salkyl, a cation (for example an alkali metal cation such as NA or K) and ammonium groups (for example those derived from reacting the acid with 4 Case 150-5771 triethanolamine or monoethanolamine).
Preferably compounds of formula I where R is C16-1.alkyl and n is 10-14 are good emulsifiers.
Such emulsifiers are useful in cosmetic emulsions, more specifically for oil in water and water in oil systems, and as emulsifiers for polymerisation in emulsion. They can also be used in metal drilling and cutting oils.
The compounds of formula I can be prepared by reacting 1 mol of a compound of formula R Cl-CH2-COORIO (11) where RIO is Ne or K with 1 mol of a compound of formula M RO-(P0).-(E0).-RIO (M) to form a product of formula IV R-0-(P0),j-(E0),,-CH2-COORIO followed by reacting with H2S04 to form a compound of formula V R-O-(po),,i-(E0),,-CH2-COOH (V) Where R, in the compound of formula 1 is other than hydrogen and C&Igalkyl, the compound of formula V can be reacted with a compound of formula VI RI-OH (V1) Case 150-5771 where R,. is a cation or an ammonium group.
Where R,, in the compound of formula 1 is C8-1salkyl, esterification of the compound of formula V can be carried out with the appropriate alkanol at high temperature (e.g. 150170Q or with a biocatalyst such as lipase at 40-50T.
A very high degree of carboxylation can be achieved (i.e. 90-95%) when n is 7-11 in compounds of formula I.
Further according to the invention there is provided a composition comprising i) lauryl ether sulphate (hereinafter defined as LES); and ii) a compound of formula I R-0-(P0).-(E0)jCH2-COOR, (1) in which m is 1 to 4; n is 2 to 20 (preferably 3 to 20); R is C,-,,alkyl or C8-1, alkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,_1.alkyl, a cation (for example an alkali metal cation such as NA' or K) and ammonium groups (for example those derived from reacting the acid with triethanolamine or monoethanolamine).
Preferably the amount of compound of formula 1 present in such a composition is 20-40% based on the weight of LES present.
The compounds of formula I are useful as surface active agents, and are suitable as emulsifiers, dispersing agents, lubricants, wetting agents, levelling agents, softening agents and 6 Case 150-5771 the like in the textile, leather, paper, lacquer, personal care, e.g., toiletries, cosmetics, etc., and rubber industries. For instance, they can be used as wetting, softening or lubricating agents in the treating and finishing 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 1 are useful for any of the following uses: a) as emulsifiers for insecticide compositions and agricultural sprays such as DDT, 2,4-D and the like; b) as additives to petroleum products, hydraulic fluids, lubricating oils, cutting oils and greases; as coating aids for use in coating compositions comprising a hydrophilic, film-forming colloid; d) as tackifiers in the adhesive layer of adhesive tapes in, e.g., the photographic industry; e) as foaming agents, emulsifying agents and softening agents in a wide variety of food products; as emulsifiers for polymerisation in emulsion; and g) as solubilisers for UV-absorbers, antioxydants, flame retarders appied in polymer substrates or in lacquers, coatings, etc.
c) f) The compounds of the present invention are especially useful as the essential emollient component in skin care compositions, e.g., skin creams, lotions, etc. Their incorporation serves to enhance not only the moisturizing and conditioning properties of the skin care compositions but the tactile properties as well. Such skin care compositions will normally contain from 0.5 to 15% by weight of compounds of formula I, preferably from 1 to 13%, and more preferably from 1.5 to 12%. The compounds of formula 1 are preferably employed as the sole emollient component, totally replacing conventional fatty ester emollients such as isopropyl myristate, isopropyl myristate, isopropyl palmitate and similar compounds. Alternatively, the compounds of formula I may be employed in combination with conventional fatty ester emollients, thereby reducing the amount of conventional fatty ester emollient that needs to be employed.
1 7 Case 150-5771 The skin care compositions can contain other ingredients commonly found in such compositions. For example, fatty alcohols may be employed to assist in stabilizing the composition and in providing a cosmetically acceptable viscosity. In general, aC,4 to C22 substantially saturated alkanol is employed. Typical examples of suitable fatty alcohols are cetyl alcohol and stearyl alcohol.
Emulsifiers may also be employed and such may be cationic e.g., quaternary ammonium compounds such a dimethyl distearyl ammonium chloride, amphoteric such as betaines or sulfobetaines and nonionic such as polyethylene glycol monostearate.
In order to improve the lubricity of the skin care compositions, a lubricant is generally employed. This may be a silicone oil such as dimethylpolysiloxane or other conventional polysiloxane.
If desired, a humectant may be present in the skin care compositions. Typical humectants which may be employed include propylene glycol and polyethylene glycol.
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 or lotion, a semi-liquid thick cream, or a paste.
The skin care compositions, in general, comprise from 13-10%, preferably from 2-8.5%, of a fatty alcohol; from 1.5-12%, preferably from 2-10%, of an emulsifying agent; and from 0.75-50%, preferably from 1-35%, of a lubricant, all percentages being by weight.
Other conventional additives typically employed in skin care compositions may be utilized. Fragrance oils, which mask the odor and provide cosmetic appeal, can be employed. Nontoxic and compatible dyes may be utilized to color the compositions, as desired. Preservatives, such as methyl paraben, propyl paraben and others may be utilized.
In addition, other ingredients can be employed beneficially to provide skin-care compositions 8 Case 150-5771 tailored to a specific use. For example, a sun screen additive such as octyl dimethyl paraaminobenzoic acid can be employed. To provide skin protection, skin protectant such as zinc oxide and the like can be employed. As a medicament, an essential oil such as menthol can be employed.
The skin care compositions of the invention exhibit good consistency, apply evenly to the skin, are absorbed rapidly and dry quickly, leaving the skin with a soft and smooth appearance. On application, they have good tactile properties without feeling oily or greasy to the touch.
The following examples in which all parts are by weight and all temperatures in degrees centigrade illustrate the invention.
Example 1
711 parts of the starting product C8H17(CA0)3-(C2HAS-OH are put into a reactor equipped with a cooling jacket connected to a thermocryostat and fitted with a stirrer. With continuous stirring and starting at 30' 174.8 parts of sodium monochloracetate and 60 parts of caustic soda are added alternatively in small portions. The temperature should be kept at about 50 and only at the end of addition (after 3 to 4 hours) the temperature can raise to 75 and is kept at this level for 2 to 3 hours. After cooling to SO' and again under stirring, 600 parts of water containing 75 parts of sulfuric acid 98% is added. The temperature raises to 90' and stirring is continued for 20 to 30 minutes after which the stirrer is stopped and the reaction mixture is let to separate. The oily layer on top of the mixture constitutes the product of formula CgH17(C3H60)3-(C2H40)5-0-CH2COOH Using the same procedure and the appropriate reactants the following compounds can be 9 Case 150-5771 produced C12-14H25-29(C3H60)1-(C.2H40)7-0-CH2COOH Example 2 C12-14H25-29(C3H60)2-(C.2H40)2-0-CH2COOH Example 3 C16-18H33-37(C3H60)2-(C2H40)10-0-CH2COOH Example 4 Application Example A For metal working (cutting and drilling) the following composition can be used as an autoemulsifiable oil:
petroleum distillate (d--0.85 and viscosity=1.2 E) 36.44 % C,,-,,H33-37(e.H40)10-0-CH2COOH 2.62% compound of Example 1 boric acid ether alkylolamide of fatty acid 2-butanol water 1.54% 31.20% 16.70% 4.20% 7.30% Application Example B A solution for blackening copper in electronic parts has the following composition:
sodium chlorite solution (31%) 44.1% sodium hydroxide solution (30%)12.5% compound of Example 2 0.2% water 43.2% A solution for engraving copper has the following composition:
sulfuric acid 98% hydrogen peroxide (111 vol.) compound of Example 2 water Application Example c 10.9% 10.0% 0.5% 78.6% A degreasing detergent for textiles has the following composition:
d-limonene compound of Example 1 polyethylene glycol 20 sorbitane mlaurate ethoxylated oleylamine propylene glycol methylether ethoxylated sec. alcohol water Application Example D 28.0% 6.7% 0.6% 4.9% 11.8% 9.0% 39.0% An alcaline detergent for dish washers has the following composition:
sodium carbonate sodium tripolyphosphate sodium metasilicate.5 H20 sodium hypochlorite (12% active chlorine) compound of Example 3 water Case 150-5771 4.0% 10.0% 10.0% 10.0% 8.0% 58.0% 11 Application Example E Case 150-5771 A degreasing microemulsion for use in the pickle bath of the leather making has the following composition:
compound of Example 1 d-limonene polyethylene glycol 20 sorbitane mlaurate ethoxylated oleylamine propylene glycol methylether water Application Example F 11.0% 33.0% 1.0% 8.0% 3.0% 44.0% A fatting liquor for thin skins in the leather making has the following composition:
compound of Example 4 ethoxylated cetyloleyl alcohol soja lecithine oleic soap sodium dodecylbenzene sulfonate 2-butoxyethanol preservative water 6.5 % 10.0% 30.0% 11.0% 10.0% 10.0% 0.2% 22.3 % 12

Claims (1)

  1. CLAIMS:
    1. A compound of formula 1 R-0-(P0).j-(E0)cCH27COOR, in which (I) m is 1 to 4; n is 2 to 20; R is C,-1salkyl or C&Ialkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, Cg-lgalkyl, a cation and ammonium groups 2. A compound according to claim 1 of formula Ib R-O-(P0).-(E0)n-CH2-COOCs.18alkyl (Ib) in which R, PO, EO, m and n are as defined in claim 1.
    3. A compound according to claim 2 of formula Ib' R-O-(PO).0),,.-CH2-COOC,-,salkyl (Ib') where R, PO, EO and m are as defined in claim 1 and n' is 7-11.
    4. The use as a detergent of a compound of formula I R-0-(P0).-(E0)jCH2-COOR, Case 150-5771 (I) 13 in which m is 1 to 4; n is 2 to 20 (preferably 3 to 20); R is C..1,alkyl or C,-1,alkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,-,,alkyl, a cation and ammonium groups.
    Case 150-5771 The use, according to claim 4, of a compound of formula I in which R isCMA4alkyl and n is 5-7.
    The use as an emulsifier of a compound of formula I R-O-(P0).-(E0).-CH2-COOR, (I) in which m is 1 to 4; n is 2 to 20; R is C,-18alkyl or C&I,alkenyl; PO is propylene oxide; EO is ethylene oxide; R, is selected from hydrogen, C,_1. alkyl, a cation and ammonium groups.
    The use according to claim 6 of a compound of formula I in which R is C16. ,, alkyl and n is 10-14.
    8. A compound substantially as herein described with reference to any one of the Examples.
GB9507982A 1994-04-20 1995-04-19 Polyalkyl ethers based on ethylene and propylene oxides and 2-haloacetates Withdrawn GB2288600A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9407778A GB9407778D0 (en) 1994-04-20 1994-04-20 Improvements in or relating to organic compounds

Publications (2)

Publication Number Publication Date
GB9507982D0 GB9507982D0 (en) 1995-06-07
GB2288600A true GB2288600A (en) 1995-10-25

Family

ID=10753795

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9407778A Pending GB9407778D0 (en) 1994-04-20 1994-04-20 Improvements in or relating to organic compounds
GB9507982A Withdrawn GB2288600A (en) 1994-04-20 1995-04-19 Polyalkyl ethers based on ethylene and propylene oxides and 2-haloacetates

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB9407778A Pending GB9407778D0 (en) 1994-04-20 1994-04-20 Improvements in or relating to organic compounds

Country Status (6)

Country Link
JP (1) JPH083153A (en)
DE (1) DE19514413A1 (en)
ES (1) ES2119629B1 (en)
FR (1) FR2719040B1 (en)
GB (2) GB9407778D0 (en)
IT (1) IT1279391B1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0897906A2 (en) * 1997-02-19 1999-02-24 Nof Corporation Process for producing a polyoxyalkylenecarboxylic acid
EP0955394A2 (en) * 1998-05-05 1999-11-10 KM Europa Metal AG Process for producing a protective coating on the interior surface of a copper pipe
US6303564B1 (en) 1997-12-02 2001-10-16 Clariant Gmbh Detergents, cleaning compositions and disinfectants comprising chlorine-active substances and fatty acid alkyl ester ethoxylates
WO2013087285A1 (en) * 2011-12-12 2013-06-20 Unilever Plc Laundry compositions and uses

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19959590A1 (en) * 1999-12-10 2001-06-13 Henkel Kgaa Metal treatment emulsion and metal working process

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB669936A (en) * 1948-09-01 1952-04-09 Sandoz Ltd Process for the preparation of polyether derivatives of acetic acid and their salts
GB1302880A (en) * 1969-12-31 1973-01-10

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH650764A5 (en) * 1980-11-28 1985-08-15 Sandoz Ag ALKYL-polyoxyalkylene CARBOXYLATE.
IT1175314B (en) * 1983-12-28 1987-07-01 Anic Spa PROCEDURE FOR THE PREPARATION OF ALKALINE METAL SALTS OF POLYETHOXYCARBOXYLIC ACIDS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB669936A (en) * 1948-09-01 1952-04-09 Sandoz Ltd Process for the preparation of polyether derivatives of acetic acid and their salts
GB1302880A (en) * 1969-12-31 1973-01-10

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0897906A2 (en) * 1997-02-19 1999-02-24 Nof Corporation Process for producing a polyoxyalkylenecarboxylic acid
EP0897906A3 (en) * 1997-02-19 1999-05-12 Nof Corporation Process for producing a polyoxyalkylenecarboxylic acid
US6303564B1 (en) 1997-12-02 2001-10-16 Clariant Gmbh Detergents, cleaning compositions and disinfectants comprising chlorine-active substances and fatty acid alkyl ester ethoxylates
EP0955394A2 (en) * 1998-05-05 1999-11-10 KM Europa Metal AG Process for producing a protective coating on the interior surface of a copper pipe
EP0955394A3 (en) * 1998-05-05 2000-04-12 KM Europa Metal AG Process for producing a protective coating on the interior surface of a copper pipe
WO2013087285A1 (en) * 2011-12-12 2013-06-20 Unilever Plc Laundry compositions and uses

Also Published As

Publication number Publication date
JPH083153A (en) 1996-01-09
DE19514413A1 (en) 1995-10-26
FR2719040A1 (en) 1995-10-27
ES2119629A1 (en) 1998-10-01
ES2119629B1 (en) 1999-07-01
ITRM950251A0 (en) 1995-04-20
ITRM950251A1 (en) 1996-10-20
GB9407778D0 (en) 1994-06-15
FR2719040B1 (en) 1997-07-11
GB9507982D0 (en) 1995-06-07
IT1279391B1 (en) 1997-12-10

Similar Documents

Publication Publication Date Title
CA1305065C (en) Skin conditioning/cleansing compositions containing propoxylated glycerol derivatives
US5130056A (en) Cleaning agent and process for its preparation
US4766153A (en) Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same
US6117915A (en) Fatty alcohol phosphate ester emulsifier compositions
CA1112174A (en) 2-acrylamido-2-methylpropane sulfonic acid salt polymer as lubricant in personal care product
US5424469A (en) Process for preparing polyglycerol fatty acid ester mixtures and use in cosmetic, pharmeceutical and chemical preparations
EP0278370B1 (en) Novel fatty acid-lactic acid ester
JPH0231759B2 (en)
US6977238B1 (en) Method for making stable aqueous foaming surfactant
US4198311A (en) Skin conditioning toilet bar
US4759875A (en) Oxo-derived mild surfactant blends
US4420410A (en) Personal care cleansing agent
EP0404331B1 (en) Cosmetic composition
US5395542A (en) Liquid detergent composition
US3060096A (en) Cosmetic preparation and process for manufacture thereof
GB2288600A (en) Polyalkyl ethers based on ethylene and propylene oxides and 2-haloacetates
US4980084A (en) Water rinsable petroleum jelly compositions
US4879399A (en) Ether sulfates of a mixture of branched 1-decanols
GB2185488A (en) Alkoxylated decanol sulphate surfactants and their use in shampoo compositions
US4744924A (en) Cosmetic detergent base
CA1209007A (en) Surfactant product
US4250193A (en) Cosmetics
US5834516A (en) Meadowfoam betaines in personal care applications
EP0273619B1 (en) Cosmetic composition
TW201809246A (en) Enhanced solubilization using a combination of extended chain surfactants

Legal Events

Date Code Title Description
732E Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)