EP1497405B1 - Zusammensetzung enthaltend eine mischung aus mono- und polylactylalkyllactaten - Google Patents
Zusammensetzung enthaltend eine mischung aus mono- und polylactylalkyllactaten Download PDFInfo
- Publication number
- EP1497405B1 EP1497405B1 EP03725293A EP03725293A EP1497405B1 EP 1497405 B1 EP1497405 B1 EP 1497405B1 EP 03725293 A EP03725293 A EP 03725293A EP 03725293 A EP03725293 A EP 03725293A EP 1497405 B1 EP1497405 B1 EP 1497405B1
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- European Patent Office
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- composition
- alkyl
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- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 16
- 238000005238 degreasing Methods 0.000 claims abstract description 6
- 238000004140 cleaning Methods 0.000 claims abstract description 5
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 alkyl radical Chemical class 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- IKRARXXOLDCMCX-UHFFFAOYSA-N butyl 2-butoxypropanoate Chemical group CCCCOC(C)C(=O)OCCCC IKRARXXOLDCMCX-UHFFFAOYSA-N 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 150000003893 lactate salts Chemical class 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000004310 lactic acid Substances 0.000 description 26
- 235000014655 lactic acid Nutrition 0.000 description 26
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 15
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 11
- 229940116333 ethyl lactate Drugs 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- ZCHWSOYFFAYRLF-UHFFFAOYSA-N ethyl 2,4-dihydroxy-2-methyl-3-oxopentanoate Chemical compound CCOC(=O)C(C)(O)C(=O)C(C)O ZCHWSOYFFAYRLF-UHFFFAOYSA-N 0.000 description 3
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 3
- 230000009965 odorless effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- OZZQHCBFUVFZGT-UHFFFAOYSA-N 2-(2-hydroxypropanoyloxy)propanoic acid Chemical compound CC(O)C(=O)OC(C)C(O)=O OZZQHCBFUVFZGT-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005237 degreasing agent Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000003903 lactic acid esters Chemical group 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- LXSVWFRZICUOLU-UHFFFAOYSA-N 2-butoxypropanoic acid Chemical compound CCCCOC(C)C(O)=O LXSVWFRZICUOLU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SWQJXJOGLNCZEY-NJFSPNSNSA-N helium-6 atom Chemical compound [6He] SWQJXJOGLNCZEY-NJFSPNSNSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- 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
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5022—Organic solvents containing oxygen
Definitions
- the present invention relates to an oligomeric composition of lactic acid esters comprising a mixture of alkyl mono- and polylactyllactates of formula: CH 3 CH (OH) [C (O) OCH (CH 3 )] n-1 CO 2 R (I) in which R represents an alkyl radical having a number of carbon atoms ranging from 1 to 4 and n is an integer equal to 2,3 or 4.
- the invention particularly relates to a composition of ethyl mono- and polylactyllactates.
- This composition can be used alone or in combination with other solvents, especially as cleaning and degreasing agents in the machine and in a non-aqueous medium for solid surfaces such as metal parts, ceramics, glass, plastics having have been soiled with oils or greases and / or their temporary protection. They can also be used for defluxing printed circuits. This defluxing operation consisting in eliminating the welding flux.
- the cleaning agents and / or degreasing must have other characteristics such as in particular having a high flash point, low toxicity, be odorless and not release into the atmosphere volatile organic compounds ( VOCs).
- composition of the present invention generally meets the criteria mentioned above.
- composition of the present invention can also be used to obtain cyclic-cyclic lactides - which are precursors of choice for obtaining polylactides used as biomaterials.
- HV Claborn (US 2,371,281) describes a process for obtaining alkyl lactyllactate by reacting lactide (3,6-dimethyl-1,4-dioxane-2,5-dione) with an alcohol R 1 OH according to the reaction :
- the main fraction (78 g) identified as ethyl lactyllactate is a slightly viscous, colorless and odorless liquid which distills at 110 ° C - 113 ° C at 7.5 mmHg.
- CE Rehberg and MB Dixon (Journal of Amber Chem., 74, page 1609, 1952) which give the physical properties of several alkyl lactyllactates (methyl, ethyl n-propyl, n-butyl, n-hexyl, n -octyl) mention that these compounds can be obtained according to the method of HV Claborn previously mentioned (U5 2,371,281) or that these compounds are by-products in the preparation of simple alkyl lactates in the laboratory stage, the conversion to alkyl lactyllactate being usually of the order of 5% to 20% depends on the alcohol / lactic acid ratio used during the esterification of said lactic acid.
- alkyl lactyllactates can be obtained by transesterification of alkyl lactate in the presence of H 2 SO 4 .
- US 6,191,087 discloses a degreasing composition containing a lactic acid ester.
- the subject of the present invention is therefore a composition
- a composition comprising a mixture of alkyl mono- and polylactylactates of formula: CH 3 CH (OH) [C (O) OCH (CH 3 )] n-1 CO 2 R (I) in which R represents an alkyl radical having a number of carbon atoms ranging from 1 to 4 and n is an integer equal to 2, 3 or 4.
- the alkyl radical is a methyl, ethyl, propyl, isopropyl or n-butyl radical.
- the alkyl radical is an ethyl radical.
- composition according to the invention may furthermore contain an alkyl lactate of formula CH 3 CH (OH) CO 2 R (II) in which R has the same meaning as in formula (I), especially in the range of 0, 1 to 1 part by weight per 100 parts by weight of the mixture L 2 A + L 3 A + L 4 A.
- It may also comprise oligomers of higher molecular masses, that is to say alkyl polylactylates in which n> 4 in particular, from 0.1 to 4 parts by weight per 100 parts by weight of the mixture L 2 A + L 3 A + L 4 A.
- composition of the present invention can be obtained by total conversion esterification of a previously concentrated commercial lactic acid solution, said total conversion being achieved by removing water formed by azeotropic distillation.
- the concentration of commercial lactic acid solutions can be achieved by simple evaporation in one or more steps, at a temperature ranging from 100 ° C to 170 ° C, at atmospheric pressure or under reduced pressure and until a composition is obtained.
- the LAT corresponds to the mass of lactic acid monomer contained in 100 g of the lactic acid composition.
- This mass is determined after saponification at a determined weight (0.1 to 0.3 g) of the oligomeric composition. After neutralization of the reaction mixture, it is analyzed by the high performance liquid chromatography (HPLC) technique with refractometric detection. This analysis can be done on a cation exchange column of the type "SHODEX SH 1011" in using N / 100 sulfuric acid as eluent. This technique makes it possible to determine the mass of lactic acid monomer contained in the tested sample and by simple calculation, the LAT.
- HPLC high performance liquid chromatography
- the concentration reaction is monitored by measuring the weight of water removed and the amount of water in the concentrate determined by the Karl Fisher water test method.
- esterification is carried out in the conventional manner in the presence of an acid catalyst chosen in particular from the group comprising sulfuric acid, phosphoric acid, para-toluenesulfonic acid, methanesulfonic acid and the resins acids such as, for example, Amberlyst A15.
- an acid catalyst chosen in particular from the group comprising sulfuric acid, phosphoric acid, para-toluenesulfonic acid, methanesulfonic acid and the resins acids such as, for example, Amberlyst A15.
- azeotropic distillation By way of illustration of azeotropic entrainers which can be used according to the present invention, mention may be made of cyclohexane or toluene.
- cyclohexane will be used.
- the total conversion esterification of the concentrated lactic acid solution is carried out at temperatures between 70 ° C. and 100 ° C. at atmospheric pressure and with an alcohol / lactic acid molar ratio ranging from 1.3 to 2.
- reaction medium is subjected to a basic treatment in order to neutralize the acid catalyst.
- this treatment is carried out on a bed of basic resin such as Amberlyst resin A21, which resin bed is washed with a solvent such as an alkyl lactact.
- basic resin such as Amberlyst resin A21
- the products of the composition according to the invention were identified by gas chromatography (GC) coupled to a mass spectrometer.
- GC gas chromatography
- composition of the invention may also be obtained from an alkyl lactate of formula (II) by transesterification in the presence of a catalyst selected from alkyl orthotitanates such as ethyl orthotitanate, zirconium acetylacetonate, tributyltin, strong bases such as KOH, NaOH, quaternary ammonium hydroxides.
- a catalyst selected from alkyl orthotitanates such as ethyl orthotitanate, zirconium acetylacetonate, tributyltin, strong bases such as KOH, NaOH, quaternary ammonium hydroxides.
- reaction medium is treated in a known manner in order to eliminate the catalyst used.
- the reaction medium is then concentrated under reduced pressure to remove the unconverted alkyl lactate.
- composition of the present invention is a colorless, odorless liquid having a flash point above 100 ° C.
- a commercial lactic acid composition having a total lactic acid content -LAT of 88.7 and a free water content of 13.3% was used.
- the LAT corresponds to the mass of lactic acid monomer contained in 100 g of the lactic acid composition.
- the LAT is determined as previously described.
- lactic acid is concentrated to a desired LAT.
- the commercial lactic acid composition to be concentrated is introduced into a rotary evaporator and then the water is removed under 100 mbar at a temperature ranging from 60 ° C. to 130 ° C.
- the reaction is monitored by measuring the amount of water removed and the percentage of water in the concentrate determined by the Karl Fisher method.
- the LAT is measured as previously described.
- Condensates at the top of the column are partially returned to the distillation column, partly to a decanter.
- the light phase of settling is recycled to the boiler, the heavy phase is eliminated.
- the reflux ratio is plotted to distill the cyclohexane / ethanol / water ternary azeotrope (75.5% / 19.7% / 4.8%) boiling at 61.2 ° C. It will be ensured throughout the reaction not to exceed this temperature at the top of the column by more than 0.3 to 0.4 ° C. For this, the reflux ratio will be adjusted during the course of handling.
- the reaction lasts about 3:30.
- the end-of-reaction criterion is the following:% H + (expressed as lactic acid) ⁇ 0.5%.
- the medium is cooled and the reaction mixture is treated with 10 g of a strong basic resin of the Amberlyst No. A21 type which is rinsed with 10 g of ethyl lactate.
- the products were identified by chromatography coupled to a mass spectrometer.
- Example 2 Same as Example 1 but replace the sulfuric acid with 6 g of Amberlyst A15.
- the reaction time is 4 hours.
- the effectiveness of said mixture is determined to remove 90% of a stain distributed on a square mesh (8 meshes per cm) 5 ⁇ 5 cm from WEBER in the form of a cylinder with a diameter of 20 mm, the two edges of the generator being 0.5 mm apart.
- the grid is then immersed in 50 ml of mixture to be evaluated with stirring (500 rpm). At the same time, a stopwatch is triggered.
- the grid is raised to 1, 3, 5, 7'30, 10, 12'30, 15 min and is then weighed at time (t) without stopping the stopwatch (duration of this operation about 20 seconds).
- the 90% efficiency time is 45 min.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cleaning By Liquid Or Steam (AREA)
Claims (9)
- Zusammensetzung, enthaltend ein Gemisch von Mono- und Polylactylmilchsäurealkylestern der Formel:
CH3CH(OH)[C(O)OCH(CH3)]n-1CO2R (I)
worin R für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen steht und n eine ganze Zahl mit einem Wert von 2, 3 oder 4 ist. - Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, daß es sich bei dem Alkylrest um einen Methyl-, Ethyl-, Isopropyl- oder n-Butylrest handelt.
- Zusammensetzung nach Anspruch 2, dadurch gekennzeichnet, daß es sich bei dem Alkylrest um einen Ethylrest handelt.
- Zusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß sie- 35 bis 85 Gewichtsteile Lactylmilchsäurealkylester (n=2 in Formel (I)), im folgenden L2A;- 10 bis 60 Gewichtsteile Dilactylmilchsäurealkylester (n=3 in Formel (I)), im folgenden L3A; und- 1 bis 20 Gewichtsteile Trilactylmilchsäurealkylester (n=4 in Formel (I)), im folgenden L4A;enthält, wobei die Summe L2A + L3A + L4A sich auf 100 Gewichtsteile beläuft.
- Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß sie außerdem einen Milchsäurealkylester der Formel CH3CH(OH)CO2R (II), worin R die gleiche Bedeutung wie in Formel (I) besitzt, in einem Anteil von 0,1 bis 1 Gewichtsteil auf 100 Gewichtsteile des Gemischs L2A + L3A + L4A enthält.
- Zusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß sie außerdem Polylactylmilchsäurealkylester (I), in denen n größer als 4 ist, in einem Anteil von 0,1 bis 4 Gewichtsteilen auf 100 Gewichtsteile des Gemischs L2A + L3A + L4A enthält.
- Verwendung einer Zusammensetzung nach einem der Ansprüche 1 bis 6 als Reinigungs- und/oder Entfettungsmittel für Metallteile.
- Verwendung einer Zusammensetzung nach einem der Ansprüche 1 bis 6, die außerdem auch noch mindestens ein Lösungsmittel enthält, als Reinigungs- und/oder Entfettungsmittel für Metallteile.
- Verwendung nach Anspruch 8, dadurch gekennzeichnet, daß es sich bei dem Lösungsmittel um Butoxypropionsäure-n-butylester handelt.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0204591A FR2838435B1 (fr) | 2002-04-12 | 2002-04-12 | Composition comprenant un melange de mono et polylactyllactates d'alkyle |
FR0204591 | 2002-04-12 | ||
PCT/FR2003/000843 WO2003087284A1 (fr) | 2002-04-12 | 2003-03-17 | Composition comprenant un melange de mono- et polylactyllactate d' alkyle |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1497405A1 EP1497405A1 (de) | 2005-01-19 |
EP1497405B1 true EP1497405B1 (de) | 2006-10-04 |
Family
ID=28459780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03725293A Expired - Lifetime EP1497405B1 (de) | 2002-04-12 | 2003-03-17 | Zusammensetzung enthaltend eine mischung aus mono- und polylactylalkyllactaten |
Country Status (9)
Country | Link |
---|---|
US (1) | US20050215453A1 (de) |
EP (1) | EP1497405B1 (de) |
JP (1) | JP2005522570A (de) |
AT (1) | ATE341609T1 (de) |
AU (1) | AU2003227839A1 (de) |
DE (1) | DE60308854T2 (de) |
ES (1) | ES2274230T3 (de) |
FR (1) | FR2838435B1 (de) |
WO (1) | WO2003087284A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2885536B1 (fr) | 2005-05-12 | 2007-07-27 | Roquette Freres | Composition a base d'ethers de dianhydrohexitol pour le traitement d'une matiere autre que le corps humain |
EP2444060B1 (de) * | 2006-07-06 | 2017-08-23 | Stepan Company | Körperpflegezusammensetzung |
WO2008006058A2 (en) * | 2006-07-06 | 2008-01-10 | Stepan Company | Alkyl lactyllactate solvent compositions |
EP2810640A1 (de) | 2013-06-03 | 2014-12-10 | Basf Se | Ester von Oligohydroxycarbonsäuren und deren Verwendung |
EP3250547B1 (de) * | 2015-01-29 | 2019-05-01 | Council of Scientific and Industrial Research | Neuartiges verfahren zur herstellung von hydroxylfunktionellen estern und polyestern daraus |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2371281A (en) * | 1945-03-13 | Lactyuactic esters and process of | ||
US5124166A (en) * | 1987-08-13 | 1992-06-23 | Nabisco, Inc. | Carboxy/carboxylate disubstituted esters as edible fat mimetics |
EP0539398A1 (de) * | 1990-07-16 | 1993-05-05 | E.I. Du Pont De Nemours And Company | Abbaubare schaummaterialien |
US6452051B1 (en) * | 1996-02-22 | 2002-09-17 | Cargill, Inc. | Process for the production of a condensation products of a carboxylic acid |
US6664413B1 (en) * | 1998-11-19 | 2003-12-16 | A. E. Staley Manufacturing Co. | Process for production of esters |
US6191087B1 (en) * | 1999-09-03 | 2001-02-20 | Vertec Biosolvents, Llc | Environmentally friendly solvent |
US6284720B1 (en) * | 1999-09-03 | 2001-09-04 | Vertec Biosolvents, Llc | Environmentally friendly ink cleaning preparation |
FR2802923B1 (fr) * | 1999-12-28 | 2002-03-08 | Roquette Freres | Procede de preparation d'une composition d'ester d'acide lactique et son utilisation en tant que solvant |
-
2002
- 2002-04-12 FR FR0204591A patent/FR2838435B1/fr not_active Expired - Fee Related
-
2003
- 2003-03-17 AU AU2003227839A patent/AU2003227839A1/en not_active Abandoned
- 2003-03-17 WO PCT/FR2003/000843 patent/WO2003087284A1/fr active IP Right Grant
- 2003-03-17 US US10/510,929 patent/US20050215453A1/en not_active Abandoned
- 2003-03-17 AT AT03725293T patent/ATE341609T1/de not_active IP Right Cessation
- 2003-03-17 JP JP2003584228A patent/JP2005522570A/ja active Pending
- 2003-03-17 DE DE60308854T patent/DE60308854T2/de not_active Expired - Fee Related
- 2003-03-17 ES ES03725293T patent/ES2274230T3/es not_active Expired - Lifetime
- 2003-03-17 EP EP03725293A patent/EP1497405B1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
WO2003087284A1 (fr) | 2003-10-23 |
AU2003227839A1 (en) | 2003-10-27 |
US20050215453A1 (en) | 2005-09-29 |
JP2005522570A (ja) | 2005-07-28 |
FR2838435B1 (fr) | 2004-06-18 |
ES2274230T3 (es) | 2007-05-16 |
DE60308854D1 (de) | 2006-11-16 |
ATE341609T1 (de) | 2006-10-15 |
DE60308854T2 (de) | 2007-08-30 |
FR2838435A1 (fr) | 2003-10-17 |
EP1497405A1 (de) | 2005-01-19 |
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