WO2011021149A1 - Concentrated aqueous solution of an amphoteric surfactant particularly betaine, and method for the preparation thereof - Google Patents
Concentrated aqueous solution of an amphoteric surfactant particularly betaine, and method for the preparation thereof Download PDFInfo
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- WO2011021149A1 WO2011021149A1 PCT/IB2010/053704 IB2010053704W WO2011021149A1 WO 2011021149 A1 WO2011021149 A1 WO 2011021149A1 IB 2010053704 W IB2010053704 W IB 2010053704W WO 2011021149 A1 WO2011021149 A1 WO 2011021149A1
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- aqueous solution
- concentrated aqueous
- amphoteric surfactant
- concentration
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- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 32
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 10
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title description 11
- 229960003237 betaine Drugs 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title 1
- 239000004202 carbamide Substances 0.000 claims abstract description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 20
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims abstract description 14
- 229910000162 sodium phosphate Inorganic materials 0.000 claims abstract description 12
- 239000001488 sodium phosphate Substances 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 13
- 235000011008 sodium phosphates Nutrition 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 5
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 2
- 235000019800 disodium phosphate Nutrition 0.000 claims description 2
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 210000001217 buttock Anatomy 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 7
- 235000013162 Cocos nucifera Nutrition 0.000 description 5
- 244000060011 Cocos nucifera Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000021588 free fatty acids Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- RRBZUCWNYQUCTR-UHFFFAOYSA-N 2-(aminoazaniumyl)acetate Chemical class NNCC(O)=O RRBZUCWNYQUCTR-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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,
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- 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)
Abstract
A low-viscosity concentrated aqueous solution is described, which comprises from 25% to 60% by weight of one or more amphoteric surfactants, preferably alky! amido propyl betaines, and from 0,01% to 5% by weight of urea and/or sodium phosphate. The concentrated aqueous solution of the invention is characterized by a low viscosity, preferably lower than or equal to 3000 cps, as measured with a model LV Brookfield viscosimeter at 20°C, 20 r.p.m., and spindle 3. Methods of preparing the concentrated aqueous solution of the invention are also described.
Description
Concentrated aqueous solution of an amphoteric surfactant particularly betaine, and method for the preparation thereof
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.
Among amphoteric surfactants, 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. However, limitations exist to the possibility of increasing the active substance, as at high concentrations the active substances tend to form an extremely viscous lamellar gel not easy to handle, The increase in viscosity or gelation can likewise occur during storage. For this reason, 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.
Several attempts to obtain low viscosity betaine concentrated aqueous solutions are described in the prior art.
European patent EP 0560114 Bl describes adding a desired amount of free fatty acids, optionally in combination with glycerol. However, 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.
This and other objects are achieved through 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.
Further features of the solution according to the invention are defined in the appended subordinate claims that form an integral part of the specification.
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 2O0C, 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.
Ln a preferred embodiment, the amphoteric surfactant is selected from the group consisting of alky] betaines, alkylamido betaines, aminopropionates, aminoglycinates, imidazolinum betaines. sulfobetaines and any mixture thereof.
More preferably, the aSkylamido betaines are alkylamidopropyl betaines of formula (1):
CHi R - CO - NH - CH3CH2CH2 - N÷ - CH2CCKJ
wherein 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. monoiso- prøpanolamine, triisopropanolamine, 2-aminobutanol, aminoethylpropanediol, arginine, lysine, ornithine, aminomethylpropanol, aminomethylpropanediol, 2-amino-2-hydroxymethyl-l ,3- propanediol. These electrolyte salts may be used individually or as a mixture.
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.
According to another embodiment of the invention, 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;
- urea: from 0.01% to 5% by weight;
- sodium phosphate: from 0.01% to 5%; and
- water: up to 100% by weight.
The aqueous solution of the invention does not include further active substances. However, 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.
Since the problem of the increase in viscosity of a concentrated amphoteric surfactant aqueous solution is mostly encountered with acidic solutions at pH < 5, the use of urea in order to reduce viscosity results particularly advantageous with solutions having such pH values. Consequently, 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.
As previously indicated, 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.
Thus, 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.
In an alternative embodiment, 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 amϊdoammes with halocarboxylic acids or salts thereof, to give alkyl betames or al- kylamido betaines.
The following examples are provided merely by way of illustration and not limitation of the
scope of the invention as defined in the appended claims. Example 1
200 g (0,78 mol) of a coconut fatty acid and 79.7 g (0.78 rnol) of N5N -dimethyl arninopropyia- rnine were inserted into a 2-liter 4-neeked round-bottomed flask fitted with a thermometer, a condenser, a water separator, a nitrogen aspiration tube and a stirrer and were heated under nitrogen at 1800C. The condensation water was continuously removed. The reaction went on until the acidic value of the mixture dropped to under 5. The amine excess was then removed under vacuum. This way, 250 g of coconut fatty acid amidopropyl dimethylamine were obtained and adjusted with water at a concentration of active substance of 45% by weight. The obtained product was basically solid.
Example 2
Example 3 was repeated, with the exception that the reaction of the coconut fatty acid with N5N- 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 200C of 210 cps,
Example 3
Amounts of 0.3% and 0.5% urea by weight were successively added to a eocoarnidopropyi be- taine aqueous preparation with a concentration of the active substance of 45% by weight obtained as described in Example 1. The appearance and viscosity of the pastes were then determined at 200C. The results are reported in Table 1.
Appearance and viscosity of the Amount of added urea
cocoamidopropyl betaine (% by weight)
pastes
0.5
Appearance at 2O0C ssel
5ity at 200C 305 cps
The influence of pH was also assessed on the formulation containing 0.5% urea by weight. The results are reported in Table 2,
E.xamp]e 4
Amounts of 0.3% and 0.5% Na3PO4 by weight were successively added to a cocoamidopropyl betaine aqueous preparation with a concentration of the active substance of 45% by weight obtained as described in Example 1. The appearance and viscosity of the pastes were then determined at 200C. The results are reported in Table 3,
Appearance and viscosity of the Amount of addec Na3PO4
cocoamidopropy] bexaine (% by weig≠)
pastes 0 J 0.3 0.5
Appearance at 20 0C gel liquid liquid
Viscosity at 200C I 360 cps 351 cps
The influence of pH was also assessed on the formulation containing 0.5% Na3PO4 by weight. The results are reported in Table 4.
Table 4
pH 4.2 4.6 4.9 5.5 7.0
Viscosity at 20°C solid
305 306 310 325 (cps) tends to separate
Claims
1. A concentrated amphoteric surfactant aqueous solution with a viscosity lower than or equal to 3000 cps, preferably lower than or equal to 1000 cps, as measured with a model LV Brookfseld viscosirneter at 2O0C, 20 r.p.m., spindle 3, characterized in that it comprises urea at a concentration of from 0.01% to 5% by weight of the total weight of the solution and further characterized in that the concentration of the amphoteric surfactant is comprised between 25% and 60% by weight.
2. The concentrated aqueous solution according to claim 1, wherein the amphoteric surfactant is selected from the group consisting of alky! betaines, alkylamido betaines, aminopropio- nates. aminogSycinates, imidazotinum betaines, sulfobelaines and mixtures thereof.
3. The concentrated aqueous solution according to claim 2, wherein the alkylamido betaines are alkylamido propyl betaines of formula (1):
R - CO - NH - CH2CH3CH: - N" - CH2COO"
CH1
(D
wherein 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 alky! groups having an average of 6 to 22 carbon atoms.
4. The concentrated aqueous solution according to any of claims 1 to 3, having a pH comprised between 1 and 9, preferably between 1 and 5, even more preferably between 4.0 and 4.9.
5. The concentrated aqueous solution according to claim 4, having a pH comprised between 4.0 and 4,5.
6. The concentrated aqueous solution according to any of claims 1 to 5, comprising, in ad- dition to urea, sodium phosphate at a concentration comprised between 0.01 % and 5% by weight more preferably between 0.1% and 3% by weight, even more preferably between 0.1% and 0.5% by weight of the total weight of the solution.
7. The concentrated aqueous solution according to claim 6, wherein the sodium phosphate is selected from the group consisting of Na3PO4, NaH2PO4. Na2HPO4 and any combination thereof.
8. The concentrated aqueous solution according to any of claims 1 to 7, comprising one or more electrolyte salts, preferably at a concentration comprised between 5% and 10% by weight of the total weight of the solution.
9. The concentrated aqueous solution according to any of claims 1 to 8. comprising the amphoteric surfactant at a concentration of from 35% to 48% by weight of the total weight of the solution.
10. The concentrated aqueous solution according to any of claims 1 to 9, comprising urea at a concentration comprised between 0.1 % and 3% by weight, preferably between 0.1 % and 0,5% by weight of the total weight of the solution.
11. A method of preparing a concentrated aqueous amphoteric surfactant solution according to any of claims 3 to 10, characterised in that it comprises synthesizing said amphoteric surfactant in the presence of an amount of urea suitable to provide a concentration from 0.01% to 5% urea by weight of the total weight of the final solution.
12. A method of preparing a concentrated aqueous amphoteric surfactant solution according to any of claims 1 to 10, characterised in that it comprises the step of providing the amphoteric surfactant and the step of adding to said amphoteric surfactant an amount of urea suitable to provide a concentration from 0.01 % to 5% by weight of the total weight of the final solution.
13. The method according to claim 1 1 or 12, further comprising adding to said amphoteric surfactant an amount of sodium phosphate suitable to provide a concentration from 0.01% to 5% by weight of the total weight of the final solution.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10752624.6A EP2467462B1 (en) | 2009-08-19 | 2010-08-17 | Concentrated aqueous solution of an amphoteric surfactant particularly betaine, and method for the preparation thereof |
| RU2012110236/04A RU2559885C2 (en) | 2009-08-19 | 2010-08-17 | Concentrated aqueous solution of amphoteric surfactant, particularly betaine, and method for preparation thereof |
| ES10752624.6T ES2532735T3 (en) | 2009-08-19 | 2010-08-17 | Concentrated aqueous solution of an amphoteric surfactant, particularly betaine, and method for preparing it |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| ITTO2009A000650A IT1395286B1 (en) | 2009-08-19 | 2009-08-19 | AQUEOUS CONCENTRATED SOLUTION OF TENSIOACTIVE ANFOTERO, PARTICULARLY BETAINE, AND PROCEDURE FOR ITS PREPARATION |
| ITTO2009A000650 | 2009-08-19 |
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| WO2011021149A1 true WO2011021149A1 (en) | 2011-02-24 |
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| 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 |
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| Country | Link |
|---|---|
| EP (1) | EP2467462B1 (en) |
| ES (1) | ES2532735T3 (en) |
| IT (1) | IT1395286B1 (en) |
| RU (1) | RU2559885C2 (en) |
| WO (1) | WO2011021149A1 (en) |
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| RU2720120C2 (en) * | 2018-10-08 | 2020-04-24 | Общество с ограниченной ответственностью "Газпром добыча Краснодар" | Composition of surfactant to maintain stable operation of water-flooded gas and gas condensate wells under conditions of falling production |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416808A (en) * | 1981-11-19 | 1983-11-22 | Hoechst Aktiengesellschaft | Bis-betaine-amine oxides, process for their preparation, and cleaning agents containing them |
| EP0573329A2 (en) * | 1992-06-03 | 1993-12-08 | Colgate-Palmolive Company | High foaming nonionic surfactant based liquid detergent |
| US5354906A (en) | 1992-03-09 | 1994-10-11 | Th. Goldschmidt Ag | Aqueous liquid solution of a betaine with a solids content of at least 40% by weight |
| US5840676A (en) * | 1994-12-15 | 1998-11-24 | Colgate-Palmolive Company | Microemulsion light duty liquid cleaning compositions |
| US5962708A (en) | 1995-04-29 | 1999-10-05 | Witco Surfactants Gmbh | Process for preparation of highly concentrated free-flowing aqueous solutions of betaines |
| US20060110354A1 (en) | 2002-10-23 | 2006-05-25 | Joaquin Bigorra Llosas | Concentrated surface-active preparations |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI0730024T1 (en) * | 1995-03-01 | 2000-02-29 | Chemische Fabrik Dr. Weigert (Gmbh & Co.) | Surgical instruments cleaning composition |
| GB9726969D0 (en) * | 1997-12-19 | 1998-02-18 | Unilever Plc | Mousse-forming shampoo compositions |
-
2009
- 2009-08-19 IT ITTO2009A000650A patent/IT1395286B1/en active
-
2010
- 2010-08-17 RU RU2012110236/04A patent/RU2559885C2/en active
- 2010-08-17 EP EP10752624.6A patent/EP2467462B1/en not_active Not-in-force
- 2010-08-17 WO PCT/IB2010/053704 patent/WO2011021149A1/en active Application Filing
- 2010-08-17 ES ES10752624.6T patent/ES2532735T3/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416808A (en) * | 1981-11-19 | 1983-11-22 | Hoechst Aktiengesellschaft | Bis-betaine-amine oxides, process for their preparation, and cleaning agents containing them |
| US5354906A (en) | 1992-03-09 | 1994-10-11 | Th. Goldschmidt Ag | Aqueous liquid solution of a betaine with a solids content of at least 40% by weight |
| EP0560114B1 (en) | 1992-03-09 | 1996-04-17 | Th. Goldschmidt AG | Betaine aqueous liquid solution with at least 40 weight-% of solid content |
| EP0573329A2 (en) * | 1992-06-03 | 1993-12-08 | Colgate-Palmolive Company | High foaming nonionic surfactant based liquid detergent |
| US5840676A (en) * | 1994-12-15 | 1998-11-24 | Colgate-Palmolive Company | Microemulsion light duty liquid cleaning compositions |
| US5962708A (en) | 1995-04-29 | 1999-10-05 | Witco Surfactants Gmbh | Process for preparation of highly concentrated free-flowing aqueous solutions of betaines |
| US20060110354A1 (en) | 2002-10-23 | 2006-05-25 | Joaquin Bigorra Llosas | Concentrated surface-active preparations |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2559885C2 (en) | 2015-08-20 |
| ITTO20090650A1 (en) | 2011-02-20 |
| EP2467462B1 (en) | 2014-12-17 |
| EP2467462A1 (en) | 2012-06-27 |
| IT1395286B1 (en) | 2012-09-05 |
| RU2012110236A (en) | 2013-09-27 |
| ES2532735T3 (en) | 2015-03-31 |
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