EP0636165A1 - Laurylglycinatlysin enthaltende waschmittelzusammensetzungen - Google Patents
Laurylglycinatlysin enthaltende waschmittelzusammensetzungenInfo
- Publication number
- EP0636165A1 EP0636165A1 EP94902024A EP94902024A EP0636165A1 EP 0636165 A1 EP0636165 A1 EP 0636165A1 EP 94902024 A EP94902024 A EP 94902024A EP 94902024 A EP94902024 A EP 94902024A EP 0636165 A1 EP0636165 A1 EP 0636165A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lysine
- detergent compositions
- compositions according
- lauroylglycine
- sodium chloride
- 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- Withdrawn
Links
- 239000004472 Lysine Substances 0.000 title claims abstract description 20
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000003599 detergent Substances 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 238000005187 foaming Methods 0.000 claims abstract description 5
- 238000004140 cleaning Methods 0.000 claims abstract description 4
- 229960003646 lysine Drugs 0.000 claims description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- JWGGSJFIGIGFSQ-UHFFFAOYSA-N N-dodecanoylglycine Chemical compound CCCCCCCCCCCC(=O)NCC(O)=O JWGGSJFIGIGFSQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 claims description 4
- 229960005337 lysine hydrochloride Drugs 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000002845 discoloration Methods 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 238000006073 displacement reaction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000008719 thickening Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 abstract description 6
- 230000002225 anti-radical effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VGMIHYGISGNHKU-UHFFFAOYSA-N (2-aminoacetyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(=O)CN VGMIHYGISGNHKU-UHFFFAOYSA-N 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000007065 protein hydrolysis Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
- 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
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
Definitions
- Detergent compositions have been known for a long time intended in particular for personal hygiene, comprising amino acid acylates derived either from partial hydrolysis of proteins which correspond to acylpeptides, or from total hydrolysis, leading to acylpolyamino acids; Acyl peptides like acylpolyamino acids being generally salified with mineral bases, mainly sodium hydroxide or organic bases like triethanolamine, monoethanolamine.
- the object of the present invention is to provide a detergent for hygienic or household use, characterized in that it comprises the smallest molecule of amino acids: glycine, acylated with the lauric chain.
- the lauroylglycinic acid thus obtained being salified with lysine, the latter resulting from lysine hydrochloride, a highly industrial product, used for animal feed
- Lauroylglycine is described in the literature as an acylamino acid, the acylation yields of which do not exceed 70%, requiring the extraction of free fatty acid, which industrially cannot be retained.
- a lauroyl ⁇ glycine will be produced with an average yield of 90%, by operating according to the following process:
- the lauroylglycine structure whose mp of the anhydrous substance is 118-119 ° corresponds to the following formula and analytical indices:
- Acid index found 225
- the exact dry extract content is determined to know the amount of lysine necessary for salification.
- the pH of such a solution is around 10.5; the hydrochloric acid of the hydrochloride being transformed into sodium chloride, the content of which is between 15 and 16%.
- This solution contains on average 35% of lysine base.
- the demonstration of this structure is carried out by treating HC1 with the lysine lauroylglycinate solution containing NaCl.
- the lauroylglycinic acid precipitates cold, with the formation of lysine hydrochloride.
- lysine is determined by chromatography. precipitate which floats on heating is washed with hot water then treated with 50% of 33% HCl and brought to boiling point with ascending refrigerant for six hours. Chromatography this time reveals the spot of glycine. is also released can be extracted by petroleum ether followed by the measurement of the acid number.
- the invention also being partial salification with lysine, supplemented with an inorganic or organic base, the presence of lysine not being able to be less than 25 or 30% of the salifying agents
- Lysine lauroylglycinate is endowed with anti-free radical properties, highlighted by the discoloration of Diphenylpicrylhydrazyl.
- This type of acylamino acid has a particular affinity for the skin and the hair, leading to the attachment of a protective film.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9215004A FR2699189B1 (fr) | 1992-12-14 | 1992-12-14 | Composition détergentes destinées principalement à l'hygiène corporelle contenant du lauroylglycinate de lysine. |
| FR9215004 | 1992-12-14 | ||
| PCT/FR1993/001234 WO1994013767A1 (fr) | 1992-12-14 | 1993-12-13 | Compositions detergentes contenant du lauroylglycinate de lysine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0636165A1 true EP0636165A1 (de) | 1995-02-01 |
Family
ID=9436535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94902024A Withdrawn EP0636165A1 (de) | 1992-12-14 | 1993-12-13 | Laurylglycinatlysin enthaltende waschmittelzusammensetzungen |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0636165A1 (de) |
| FR (1) | FR2699189B1 (de) |
| WO (1) | WO1994013767A1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3246384A1 (de) * | 2016-05-18 | 2017-11-22 | Basf Se | Wässrige tensid-zusammensetzungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY107820A (en) * | 1990-06-05 | 1996-06-29 | Ajinomoto Kk | Detergent composition. |
| FR2676922B1 (fr) * | 1991-06-03 | 1995-01-20 | Givaudan Lavirotte | Applications en cosmetique de derives n-acyles de melanges d'acides amines issus d'hydrolysats de proteines vegetales. |
-
1992
- 1992-12-14 FR FR9215004A patent/FR2699189B1/fr not_active Expired - Fee Related
-
1993
- 1993-12-13 WO PCT/FR1993/001234 patent/WO1994013767A1/fr not_active Ceased
- 1993-12-13 EP EP94902024A patent/EP0636165A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9413767A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2699189B1 (fr) | 1995-01-27 |
| WO1994013767A1 (fr) | 1994-06-23 |
| FR2699189A1 (fr) | 1994-06-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR |
|
| 17P | Request for examination filed |
Effective date: 19941215 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19961105 |