EP2467462A1 - Konzentrierte wässrige lösung eines amphoteren tensids, im besonderen betain, und herstellungsverfahren dafür - Google Patents

Konzentrierte wässrige lösung eines amphoteren tensids, im besonderen betain, und herstellungsverfahren dafür

Info

Publication number
EP2467462A1
EP2467462A1 EP10752624A EP10752624A EP2467462A1 EP 2467462 A1 EP2467462 A1 EP 2467462A1 EP 10752624 A EP10752624 A EP 10752624A EP 10752624 A EP10752624 A EP 10752624A EP 2467462 A1 EP2467462 A1 EP 2467462A1
Authority
EP
European Patent Office
Prior art keywords
weight
aqueous solution
concentrated aqueous
amphoteric surfactant
concentration
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
EP10752624A
Other languages
English (en)
French (fr)
Other versions
EP2467462B1 (de
Inventor
Fabrizio Guala
Elisabetta Merlo
Giovanni Villa
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.)
Zschimmer and Schwarz Italiana SpA
Original Assignee
Zschimmer and Schwarz Italiana SpA
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 Zschimmer and Schwarz Italiana SpA filed Critical Zschimmer and Schwarz Italiana SpA
Publication of EP2467462A1 publication Critical patent/EP2467462A1/de
Application granted granted Critical
Publication of EP2467462B1 publication Critical patent/EP2467462B1/de
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C11D3/323—Amides; Substituted amides urea or derivatives thereof
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/92—Sulfobetaines ; Sulfitobetaines

Definitions

  • the present invention refers to a concentrated aqueous solution of an amphoteric surfactant, particularly betaine, and a method for the preparation thereof.
  • Amphoteric surfactants exhibit excellent foaming and detergent properties, combined with a very good dermatological compatibility and an ability to decrease the irritating power of anionic surfactants conventionally used in the cosmetic field, such as sodium lauryl/laurylethGxy sulfate.
  • Amphoteric surfactants are used as raw materials for preparing both detergents, such as for example washing-up liquids, and cosmetic products, such as for example shampoos and bath foams.
  • alkyl betaines and particularly alkyl amidobetaines, acquired a particular importance from the commercial point of view. Among these, the most important is doubtlessly cocamidopropyl betaine.
  • Amphoteric surfactants are marketed in the form of concentrated aqueoas solutions. The tendency in this area is of increasing as much as possible the concentration of the active substance in the aqueous solutions to be marketed.
  • conventional amphoteric surfactant aqueous solutions particularly alkylamido propyl betaine, are characterized by a concentration of about 30% of active matter and 35% as the dry residue.
  • European patent EP 0560114 Bl describes adding a desired amount of free fatty acids, optionally in combination with glycerol.
  • fatty acids are quite expensive additives and their presence in a detergent or cosmetic product not always is considered as acceptable, since frequently fatty acids form as processing residues, which implies that limitations may be imposed to the concentration thereof in the finished product, Moreover, a sensible reduction in the viscosity of surfactant solutions is only observed at free fatty acid concentration values higher than 1% by weight.
  • US patent 5962708 intends to reduce the viscosity of a betaine solution by adding hydroxycar- boxylic acids or salts thereof, more particuiariy sodium citrate. Such additives are even more expensive than fatty acids, which makes this technical solution very little attractive,
  • US patent application US 20060110354 describes the use of at least one sulfate, particularly sodium sulfate from 0.01 % to 5% by weight. However, sulfates are also considered as impurities, the presence of which not always is desirable in finished formulations.
  • One object of the present invention is thus of providing a concentrated aqueous solution of an amphoteric surfactant, preferably betaine, which does not exhibit the drawbacks of the prior art.
  • a concentrated amphoteric surfactant aqueous solution as defined in the preamble of claim 1, characterised in that it comprises urea at a concentration of from 0.01% to 5% by weight of the total weight of the solution.
  • the inventors have surprisingly found that adding a small amount of urea to a concentrated amphoteric surfactant aqueous solution is sufficient to reduce the viscosity at values equal to or lower than 3000 cps, preferably equal to or lower than 1000 cps (viscosity as measured with a model LV Brookfseld viscosimeter at 2O 0 C, 20 r.p.m., spindle 3).
  • Urea is added in a suitable amount during or after the synthesis of the amphoteric surfactant.
  • the urea concentration ranges from 0.01% to 5% by weight, preferably from 0.1% to 3% by weight, more preferably from 0.1% to 0.5% by weight, of the total weight of the surfactant solution.
  • the amphoteric surfactant is selected from the group consisting of alky] betaines, alkylamido betaines, aminopropionates, aminoglycinates, imidazolinum betaines. sulfobetaines and any mixture thereof.
  • aSkylamido betaines are alkylamidopropyl betaines of formula (1):
  • R is a linear or branched, saturated or unsaturated alkyl group having from 6 to 22 carbon atoms, or a mixture of linear or branched, saturated or unsaturated alkyl groups having an average of 6 to 22 carbon atoms.
  • a preferred value for R is the alkyl group from coconut fatty acids. The average composition of coconut fatty acids, derived from coconut oil. is specifically described in US 5 354 906. Such a description is hereby incorporated as reference,
  • Solutions of alkylamido propyl betaines of formula (I) contain electrolyte salts that neutralize the charges and are preferably selected from alkaline or alkaline earth metal chlorides or chlorides with other monovalent (such as for example Cu+), divalent (such as for example Pb2+), trivalent (such as for example A13+), polyvalent (such as for example Sn4+ or NH4+) cations or with amine bases selected from triethanolamine, monoethanolamine, diethanolamine.
  • electrolyte salts that neutralize the charges and are preferably selected from alkaline or alkaline earth metal chlorides or chlorides with other monovalent (such as for example Cu+), divalent (such as for example Pb2+), trivalent (such as for example A13+), polyvalent (such as for example Sn4+ or NH4+) cations or with amine bases selected from triethanolamine, monoethanolamine, diethanolamine.
  • the concentration of the amphoteric surfactant in the concentrated aqueous solution of the invention ranges from 25% to 60% by weight, more preferably from 35% to 48% by weight, of the total weight of the solution.
  • the concentrated amphoteric surfactant aqueous solution comprises sodium phosphate as a further component capable of decreasing the viscosity and prevent gelation of the solution during storage.
  • the concentration of sodium phosphate ranges between 0 and 5%, preferably between 0.01 % and 5%, even more preferably between 0.1% and 3% and even more preferably between 0.1% and 0.5% by weight, of the total weight of the solution.
  • Sodium phosphate is used in the form of Na3PO4, NaH2PO4, Na2HPO4 or any combination thereof.
  • a preferred composition according to the invention comprises the following ingredients:
  • amphoteric surfactant preferably alkylamido propyl betaines of formula (I): from 25% to 60% by weight;
  • the aqueous solution of the invention does not include further active substances.
  • manufacturing residues may be present, such as for instance electrolyte salts as mentioned previously (particularly sodium chloride) the amount of which, if present, generally adds up to 5- 10% by weight, unreacted raw materials and small amounts of free fatty acids or salts thereof.
  • the quantity of free fatty acids or salts thereof is maintained as much as possible at very low levels.
  • the aqueous solution of the invention can be acidic, neutral or basic, the pH value thereof being preferably comprised between 1 and 9.
  • a preferred embodiment of the invention is a concentrated amphoteric surfactant aqueous solution as previously defined, having a pH value comprised between 1 and 5, more preferably comprised between 4.0 and 4,9. Further preferred pH ranges are the following: from 4.0 to 4.5; from 4,0 to 4,4; from 4.0 to 4,3; from 4,0 to 4.2: and from 4.0 to 4.1.
  • one advantage of the present invention is that urea can be added during the course of the synthesis reaction for the surfactant or. alternatively, it can be added to the already-synthesized surfactant, during the processing of the final product. Adding urea to the already-synthesized surfactant is to be preferred when the surfactant viscosity must be adjusted at an extremely precise value. Sodium phosphate instead is added at the end of the synthesis reaction for the surfactant.
  • another object of the present invention is a method according to the preamble of claim 10, characterized in that it comprises synthesizing the said amphoteric surfactant in the presence of a quantity of urea suitable to provide a concentration from 0.01% to 5% by weight, preferably from 0.1% to 3% by weight preferably from 0.1% to 0.5% by weight, of the total weight of the solution.
  • the method of the invention is characterized in that it comprises adding, to said amphoteric smfactant, a quantity of urea suitable to provide a concentration from 0,01% to 5% by weight preferably from 0,3% to 3% by weight, preferably from 0.1% to 0.5% by weight, of the total weight of the solution.
  • Both the above-described method embodiments may include adding, to the amphoteric surfactant, a quantity of sodium phosphate suitable to provide a concentration comprised between 0 and 5% by weight, preferably comprised between 0.01% and 5% by weight, even more preferably comprised between 0.1% and 3% by weight and even more preferably comprised between 0.1% and 0.5% by weight, of the total weight of the solution.
  • Examples of synthesis reactions for the amphoteric surfactant are quatemization of fatty amines or fatty acid am ⁇ doammes with halocarboxylic acids or salts thereof, to give alkyl betames or al- kylamido betaines.
  • Example 3 was repeated, with the exception that the reaction of the coconut fatty acid with N 5 N- dimethyl aminopropylarnine was carried out in the presence of 0.81 g (corresponding to 0.3% by weight, on the basis of the final composition) urea.
  • the mixture was adjusted with water at a concentration of active substance of 45% by weight with a Brooklield viscosity at 20 0 C of 210 cps,

Landscapes

  • 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)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP10752624.6A 2009-08-19 2010-08-17 Konzentrierte wässrige lösung eines amphoteren tensids, im besonderen betain, und herstellungsverfahren dafür Not-in-force EP2467462B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITTO2009A000650A IT1395286B1 (it) 2009-08-19 2009-08-19 Soluzione acquosa concentrata di tensioattivo anfotero, particolarmente betaina, e procedimento per la sua preparazione
PCT/IB2010/053704 WO2011021149A1 (en) 2009-08-19 2010-08-17 Concentrated aqueous solution of an amphoteric surfactant particularly betaine, and method for the preparation thereof

Publications (2)

Publication Number Publication Date
EP2467462A1 true EP2467462A1 (de) 2012-06-27
EP2467462B1 EP2467462B1 (de) 2014-12-17

Family

ID=41728269

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10752624.6A Not-in-force EP2467462B1 (de) 2009-08-19 2010-08-17 Konzentrierte wässrige lösung eines amphoteren tensids, im besonderen betain, und herstellungsverfahren dafür

Country Status (5)

Country Link
EP (1) EP2467462B1 (de)
ES (1) ES2532735T3 (de)
IT (1) IT1395286B1 (de)
RU (1) RU2559885C2 (de)
WO (1) WO2011021149A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2720120C2 (ru) * 2018-10-08 2020-04-24 Общество с ограниченной ответственностью "Газпром добыча Краснодар" Композиция пав для поддержания стабильной эксплуатации обводняющихся газовых и газоконденсатных скважин в условиях падающей добычи

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3145734A1 (de) * 1981-11-19 1983-05-26 Hoechst Ag, 6230 Frankfurt Bis-betain-aminoxide, verfahren zu deren herstellung und diese enthaltende reinigungsmittel
DE4207386C2 (de) 1992-03-09 1997-02-13 Goldschmidt Ag Th Wäßrige flüssige Lösung eines Betains mit mindestens 40 Gew.-% Festkörpergehalt
NZ247673A (en) * 1992-06-03 1994-10-26 Colgate Palmolive Co High foaming aqueous liquid detergent containing non-ionic surfactant supplemented by anionic and betaine surfactants
US5840676A (en) * 1994-12-15 1998-11-24 Colgate-Palmolive Company Microemulsion light duty liquid cleaning compositions
ATE185592T1 (de) * 1995-03-01 1999-10-15 Weigert Chem Fab Reinigungsmittel für chirurgische instrumente
DE19515883A1 (de) 1995-04-29 1996-10-31 Witco Surfactants Gmbh Verfahren zur Herstellung hochkonzentrierter fließfähiger wäßriger Lösungen von Betainen
GB9726969D0 (en) * 1997-12-19 1998-02-18 Unilever Plc Mousse-forming shampoo compositions
ATE362507T1 (de) * 2002-10-23 2007-06-15 Cognis Ip Man Gmbh Konzentrierte grenzflächenaktive zubereitungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2011021149A1 *

Also Published As

Publication number Publication date
RU2559885C2 (ru) 2015-08-20
IT1395286B1 (it) 2012-09-05
EP2467462B1 (de) 2014-12-17
ITTO20090650A1 (it) 2011-02-20
ES2532735T3 (es) 2015-03-31
WO2011021149A1 (en) 2011-02-24
RU2012110236A (ru) 2013-09-27

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