CS216263B1 - Complexones of the monoanine type with hydroxyalkyl group in the molecule with surface-active properties - Google Patents
Complexones of the monoanine type with hydroxyalkyl group in the molecule with surface-active properties Download PDFInfo
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- CS216263B1 CS216263B1 CS480A CS480A CS216263B1 CS 216263 B1 CS216263 B1 CS 216263B1 CS 480 A CS480 A CS 480A CS 480 A CS480 A CS 480A CS 216263 B1 CS216263 B1 CS 216263B1
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- Czechoslovakia
- Prior art keywords
- molecule
- type
- hydroxyalkyl group
- ppm
- monoanine
- Prior art date
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- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- OIIWPAYIXDCDNL-UHFFFAOYSA-M sodium 3-(trimethylsilyl)propionate Chemical compound [Na+].C[Si](C)(C)CCC([O-])=O OIIWPAYIXDCDNL-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004876 x-ray fluorescence Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- YGEVMZLRIOFHSG-UHFFFAOYSA-L disodium dodecanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O YGEVMZLRIOFHSG-UHFFFAOYSA-L 0.000 description 1
- QNICMVJKCYAMIK-UHFFFAOYSA-L disodium octadecanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O QNICMVJKCYAMIK-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- Detergent Compositions (AREA)
Description
Vynález sa týká komplexónov monoamínového typu s hydroxyalkylovou skupinou v molekule obecného vzorcaThe invention relates to complexes of a monoamine type with a hydroxyalkyl group in a molecule of the general formula
R-N-CH2-COOXR-N-CH2-COOX
Ί ch2-ch2-oh s povrchovoaktívnymi vlastnostami.2 ch 2 -ch 2 -oh with surface-active properties.
V súčasnosti sú známe 2-amino-(N-2-hydroxyetyl-N-karboxymetyl) mastné kyseliny s uhlíkatým reťazoom do C3. Tieto látky •boli študované viacerými autormi: Djatlova N. M. a kol.: Ž. neorg. chim. 10, 1131 (1965), Schwiarzenbaoh G., Anderegg G., Schneider W., Seen H.: Helv. chim. acta 38, 1147 (1955), Jokl V., Majer J., Mazáčová M.: Chem. zvěsti 18, 585 (1964), Chabereck S., Martell A.: J. Am. Chem. Soc. 76, 215 (1954), Majer J., Riečanská E.: Chem. zvěsti 22, 15 (1968). Doteraz známe 2namino-(N-2-1hydroxyetyl-N-karboxymetyl) mastné kyseliny nemajú povrchovo<tíw vlastnosti a nemožno ioh zařadit medzi tenzidy. Nevýhody .známého stavu odstraňujú komplexóny monoamínového typu s hydroxyalkylovou skupinou v molekule, ktoré majú oproti doteraz známým komplexónom povrehovoaktívne vlastnosti pri zachovaní chelatačných vlastností. Látky majú široká možnost využitia v praxi.Presently known are 2-amino- (N-2-hydroxyethyl-N-carboxymethyl) fatty acids with a carbon chain up to C 3 . These substances have been studied by several authors: Djatlova NM et al .: Ž. non-org. chim. 10, 1131 (1965), Schwiarzenbaoh, G., Anderegg, G., Schneider, W., Seen, H .: Helv. chim. acta 38, 1147 (1955), Jokl V, Majer J., Mazacova M .: Chem. rumors 18, 585 (1964), Chabereck, S., Martell, A .: J. Am. Chem. Soc. 76, 215 (1954); Majer J., Riečanská E. Chem. rumors 22, 15 (1968). Prior art 2namino- (N-1 2-hydroxyethyl-N-carboxymethyl) fatty acid surfactants are not <TIW ioh characteristics and can include the surfactant. Disadvantages of the prior art eliminate the monoamine-type hydroxyalkyl group complexes in the molecule, which have post-surfactant properties over the previously known complexons while retaining chelating properties. Substances have a wide range of practical applications.
Podstatou vynálezu sú komplexóny monoamínového typu s hydroxyalkylovou skupinou v molekule obecného vzorcaThe present invention provides monoamine-type complexes with a hydroxyalkyl group in a molecule of formula
R-N-CH2-COOXR-N-CH2-COOX
I ch2-ch2-oh kde R = CH3—(CH2)n—CH—COOX n = 3—17 (I ch 2 -ch 2 -oh where R = CH 3 - (CH 2 ) n —CH — COOX n = 3–17 (
X = H, Na, K, NH4 +, CH3, C2H5, C3H7 s povrohovoaktívnymi vlastnostami. Připravené látky sa vyznačujú povrchovoaktívnymi vlastnostami pri zachovaní chelatačných vlastností. Rozširujú škálu doteraz známých amíotenzidov alkylbetaínového typu a sú široké možnosti ich využitia v praxi.X = H, Na, K, NH 4 + , CH 3 , C 2 H 5 , C 3 H 7 with superficially active properties. The prepared compounds exhibit surface-active properties while maintaining chelating properties. They broaden the range of alkylbetaine-type amine-surfactants known so far and are widely used in practice.
Příklad 1Example 1
2-ammo-(N-2-hydroxyetyl-Njkariboxymetyl) laurová kyselina C16H31ŇO52-amino- (N-2-hydroxyethyl-N kariboxymetyl j) lauric acid C16H31ŇO5
2-.amÍno-(N-2-hydroxyetyl-N-karboxymetyl) laurová kyselina a jej soli bola připravená spósobom karboxyalkyláoie amínov s halogénkyselinami vo vodnoalkoholickom prostředí pri pH 9 až 11 postupom podía čs. autorského osvedčenia2-amino- (N-2-hydroxyethyl-N-carboxymethyl) lauric acid and its salts were prepared by the method of carboxyalkylation of amines with haloacids in a hydroalcoholic medium at pH 9-11 using the procedure described in U.S. Pat. author's certificate
Výťažok: 79,5 % teorie.Yield: 79.5% of theory.
Totožnost látky bola potvrdená.The identity of the substance was confirmed.
Elementárna analýza:Elemental analysis:
Ci6H31NO5 ΐθονθί * % C = 60,54, θ/ο Η = 9,84, % N = 4,41 nájdené:Ci 6 H 31 NO 5 ΐθονθί *% C = 60.54, θ / ο 9 = 9.84,% N = 4.41 found:
% C = 60,75, % H = 9,96, % N = 4,51 Teplota topenia: 86,5—87 °C Ή — NMR spektrum sodnej soli: spektrometer Tesla BS 487 A (80 MHz), rozpúšťadlo D2O, standard trimetylsilylpropionan sodný — d4, δ [ppm]% C = 60.75,% H = 9.96,% N = 4.51 Melting point: 86.5—87 ° C Ή - Sodium salt NMR spectrum: Tesla BS 487 A (80 MHz) spectrometer, solvent D 2 O, sodium trimethylsilylpropionate standard - d 4 , δ [ppm]
CH3 - 0,81 ppm (t, 3H)., - (CH2)9 - 1,37 ppm (m, 18H); HO-CH2-CH2- 2,59 ppm (t, 2H); HO-CH2-CH2- 3,59 ppm (t, 2H); HOOC-CH2- 2,96 ppm (s, 2H); -CH-COOH 4,25 ppm (t, 1Ή).CH 3 - 0.81 ppm (t, 3H). - (CH 2 ) 9 - 1.37 ppm (m, 18H); HO-CH 2 -CH 2 - 2.59 ppm (t, 2H); HO-CH 2 -CH 2 - 3.59 ppm (t, 2H); HOOC-CH 2 - 2.96 ppm (s, 2H); -CH-COOH 4.25 ppm (t, 1H).
Povrchová aktivita:Surface activity:
hodnoty povrchového napátia γ [N/m.10*3] vodných roztokov dvojsodnej soli 2-amino(N-2-hydroxyetyl-N-karboxymetyl) laurovéj kyseliny v závislosti na teplote a koncentrácii.surface tension values of γ [N / m.10 * 3 ] aqueous solutions of 2-amino (N-2-hydroxyethyl-N-carboxymethyl) lauric acid disodium salt as a function of temperature and concentration.
Koncentr.Conc.
Chelatačné vlastnosti 2-amino-(N-2-hydroxyetyl-N-karboxymetyl) laurovej kyselinyChelating properties of 2-amino- (N-2-hydroxyethyl-N-carboxymethyl) lauric acid
VýťaKovový Analýza, %_ Che- žok ión teoretické nájdené lát chelátuExtract Analysis,% _ The ion of the theoretical chelate found
1 Obsah kovu stanovený rádionuklidovou róntgenflorescenčnou analýzou; zdroj 241Am/ /Ag, energia 22,2 keV a 60 keV; detekcia polovodičový Si/Li detektor. K stanoveniu sa využila selekcia charakteristického žiarenia Kol. 1 Metal content determined by radionuclide X-ray fluorescence analysis; source 241 Am / / Ag, energy 22.2 keV and 60 keV; detection semiconductor Si / Li detector. The determination of characteristic radiation K ol was used for the determination.
Příklad 2Example 2
2-amino (N-2-hydroxyetyl-N-karboxymetyl) stearová kyselina C22H43NO5 2-amino (N-2-hydroxyethyl-N-carboxymethyl) stearic acid C 22 H 43 NO 5
2-amino (N-2-hydroxyetyl-N-karboxymetyl) stearová kyselina a jej soli bola připravená ispósobom karboxyalkylácie amínov s halogénkyselinami vo vodnoalkalickom prostředí pri pH 9 až 11 postupom podía čs. autorského osvedčenia č. (PV 3-80).2-Amino (N-2-hydroxyethyl-N-carboxymethyl) stearic acid and its salts were prepared by the method of carboxyalkylation of amines with haloacids in aqueous alkaline medium at pH 9-11 by the procedure of Cd. of the author's certificate no. (PV 3-80).
Výfažok: 81,8 % teorie.Yield: 81.8% of theory.
Totožnost látky bola potvrdená.The identity of the substance was confirmed.
Elementárna analýza:Elemental analysis:
C22H43NO5 ΐθΟΓθΐ · % C = 65,80, % H = 10,80, % N = 3,48 nájdené:C 22 H 43 NO 5 %θΟΓθΐ ·% C = 65.80,% H = 10.80,% N = 3.48 found:
%C = 66,12, % H = 11,00, % N = 3,47 Teplota topenia: 114—115 °C 1H— NMR spektrum sodnej soli:% C = 66.12,% H = 11.00,% N = 3.47 Melting point: 114-115 ° C 1 H-NMR spectrum of sodium salt:
spektrometer Tesla BS 487 A (80 MHz), rozpúšťadlo D2O, standard trimetylsilylpropionan sodný — id4, á [ppm]Tesla BS 487 A (80 MHz) spectrometer, D 2 O solvent, sodium trimethylsilylpropionate standard - id 4 , α [ppm]
CHS— 0,85 ppm (t, 3H); —(CH2)i5— 1,35 ppm (m, 3OH); HO-CH2-CH2- 2,66 ppm (t, 2H):, HO-CH2-CH2- 3,61 ppm (t, 2H); HOOC-CH2- 3,05 ppm (s, 2H); HOOC-CH- 4,21 ppm (t, 1H).CHS = 0.85 ppm (t, 3H); - (CH 2 ) 15 - 1.35 ppm (m, 3OH); HO-CH 2 -CH 2 - 2.66 ppm (t, 2H) :, HO-CH 2 -CH 2 - 3.61 ppm (t, 2H); HOOC-CH 2 - 3.05 ppm (s, 2H); HOOC-CH- 4.21 ppm (t, 1 H).
Povrchová aktivita:Surface activity:
hodnoty povrchového napátia γ [N/m.10-3] vodných roztokov dvojsodnej soli 2-amino(N-2-hydroxyetyl-N-karboxymetyl) stearovej kyseliny v závislosti na teplote a koncentrácii.surface tension values of γ [N / m.10 -3 ] aqueous solutions of 2-amino (N-2-hydroxyethyl-N-carboxymethyl) stearic acid disodium salt as a function of temperature and concentration.
Koncentr.Conc.
Pri koncentráciách 5 g/l a 10 g/l látka neholá rozpustná pri teplotách merania.At concentrations of 5 g / l and 10 g / l the substance does not shave soluble at the measurement temperatures.
Chelatačné vlastnosti 2-amino- (N-2-hydroxyetyl-N-karboxymetyl) stearovej kyseliny:Chelating properties of 2-amino- (N-2-hydroxyethyl-N-carboxymethyl) stearic acid:
Kovový iónMetal ion
VýťaAnalýza % Che- žok teoretické nájdené lát chelátuExtractionAnalysis% Cheese theoretical found chelate
+ Obsah kovu stanovený rádionuklidovou rontgenfloresceňčnou analýzou; zdroj M1Am·/ /Ag, energia 22;2keV a 60keV; detekcia polovodičový Si/Li detektor. K stanovému sa využila selekcia charakteristického žiarenia Kal. + Metal content determined by radionuclide X-ray fluorescence analysis; source M1 Am · / / Ag, energy 22, 2keV and 60keV; detection semiconductor Si / Li detector. Selection of characteristic irradiation K α1 was used in the tent.
Komplexóny monoamínového typu s hydroxyalkylovou skupinou v molekule s povrchovoaktívnymi vlastnosťami možno použiť ako analytické komplexotvorné činidlá, ako antioxidanty a stabilizátory mastí a emulzií vo farmácii a kozmetike, ďalej ako suroviny pre výrobu detergentov.Monoamine-type hydroxyalkyl complexes in a surface-active molecule can be used as analytical complexing agents such as antioxidants and ointment and emulsion stabilizers in pharmacy and cosmetics, as well as detergent raw materials.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS480A CS216263B1 (en) | 1980-01-02 | 1980-01-02 | Complexones of the monoanine type with hydroxyalkyl group in the molecule with surface-active properties |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS480A CS216263B1 (en) | 1980-01-02 | 1980-01-02 | Complexones of the monoanine type with hydroxyalkyl group in the molecule with surface-active properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216263B1 true CS216263B1 (en) | 1982-10-29 |
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ID=5331423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS480A CS216263B1 (en) | 1980-01-02 | 1980-01-02 | Complexones of the monoanine type with hydroxyalkyl group in the molecule with surface-active properties |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216263B1 (en) |
-
1980
- 1980-01-02 CS CS480A patent/CS216263B1/en unknown
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