CS199072B1 - Tenzides based on complexones of monoamines and process for preparing them - Google Patents
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- CS199072B1 CS199072B1 CS444877A CS444877A CS199072B1 CS 199072 B1 CS199072 B1 CS 199072B1 CS 444877 A CS444877 A CS 444877A CS 444877 A CS444877 A CS 444877A CS 199072 B1 CS199072 B1 CS 199072B1
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- acid
- salt
- reaction mixture
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- ester
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- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000011541 reaction mixture Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910017840 NH 3 Inorganic materials 0.000 claims description 2
- 229940124277 aminobutyric acid Drugs 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 carbon chain fatty acids Chemical class 0.000 description 5
- 239000005639 Lauric acid Substances 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 2
- QUBNFZFTFXTLKH-UHFFFAOYSA-N 2-aminododecanoic acid Chemical compound CCCCCCCCCCC(N)C(O)=O QUBNFZFTFXTLKH-UHFFFAOYSA-N 0.000 description 1
- XELWBYCKQCNAGY-UHFFFAOYSA-N 2-aminohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(N)C(O)=O XELWBYCKQCNAGY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- PBLZLIFKVPJDCO-UHFFFAOYSA-N omega-Aminododecanoic acid Natural products NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 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
- 239000005871 repellent Substances 0.000 description 1
- IOWIQTQXGCMKBS-UHFFFAOYSA-M sodium;2-aminododecanoate Chemical compound [Na+].CCCCCCCCCCC(N)C([O-])=O IOWIQTQXGCMKBS-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Predmetom vynálezu sú tenzidy zo skupiny derivátov Komplexónu I s mastnými kyselinami obecného vzorca R-N-(CH2COOH)2, ktoré predstavujú nové tenzidy s chelatačným účinkom a spósob ich výroby,The present invention relates to surfactants from the group of derivatives of Complexon I with fatty acids of the general formula RN- (CH 2 COOH) 2 , which are novel surfactants with a chelating effect and a process for their preparation,
V súčasnosti sú známe deriváty Komplexónu 1 s mastnými kyselinami s uhlíkatým reťazcom do C6. Tieto látky boli připravené reakciou karboxyalkylácie aminokyselin s halogénoctoyou. kyselinou v alkalickom prostředí viacerými autormi: Kazarinova N. F., Latoš N. I., Postoyskij I. J.: Izv. Sibirsk. Akad. Nauk SSSR (1960), 60; Irving Η. Μ. N. H„ Miles M. G.: J. Chem. Soc. A. (1966), 1268; Uehara A. Kyuno E., Tsuchiya R.: Bull. Chem. Soc. Jap. 41, 2393 (1968). Podfa uvedených práč příprava derivátov Komplexónu I s mastnými kyselinami s uhlíkatým reťazcom do C6 je náročná na čas, ich izolácia je zložitá a výťažky sa pohybujú v rozmedzí 42 až 73 %. Doteraz známe deriváty Komplexónu I nemajú povrchovoaktívne vlastnosti a nemožno ich zařadit’ medzi tenzidy. Nevýhody známého stavu odstraňujú tenzidy na báze komplexónov monoamínového typu a spósob ich výroby podfa vynálezu. Nové připravené deriváty Komplexónu I oproti doteraz známým majú povrchovoaktívne vlastnosti pri zachovaní cholatačných vlastností. Spósob ich výroby je jednoduchý, izólácia požadovaných produktov je rýchla a jednoduchá, výťažky reakcie sú 70 až 90 %. Získavajú sa látky vysokej čistoty. Tieto látky majú širokú možnosť využit ia v praxi.Complexone 1 derivatives with carbon chain fatty acids up to C 6 are currently known. These compounds were prepared by reacting the carboxyalkylation of amino acids with a haloacetate. acid in alkaline environment by several authors: Kazarinova NF, Latos NI, Postoyskij IJ: Izv. Sibirsk. Akad. Nauk USSR (1960) 60; Irving Η. Μ. Miles MG, N. H. J. Chem. Soc. A. (1966) 1268; Uehara A. Kyuno E., Tsuchiya R .: Bull. Chem. Soc. Jap. 41, 2393 (1968). Accordingly, the preparation of Complexon I derivatives with carbon chain fatty acids of up to C 6 is time-consuming, difficult to isolate, and yields ranging from 42 to 73%. The hitherto known complexlex I derivatives have no surface-active properties and cannot be classified as surfactants. Disadvantages of the prior art are eliminated by monoamine type complexone surfactants and a process for their preparation according to the invention. The novel prepared Complexone I derivatives, as compared to the prior art, have surface-active properties while retaining the chelating properties. The method of their preparation is simple, the isolation of the desired products is fast and simple, the reaction yields are 70 to 90%. High purity substances are obtained. These substances have a wide range of practical applications.
Podstatou vynálezu sú tenzidy zo skupiny derivátov Komplexónu I s mastnými kyselinami charakterizované obecným vzorcomThe present invention provides surfactants from the group of complex fatty acid derivatives of complex I characterized by the general formula
R-N-(CH2COOX)2 kdeRN- (CH 2 COOX) 2 where
R = CH3-(CH2)n -CH — COOX n = 3—17R = CH 3 - (CH 2 ) n -CH-COOX n = 3-17
X = H, Na, K, NHt, CH3, C2H5, C3H7 X = H, Na, K, NH 3 , CH 3 , C 2 H 5 , C 3 H 7
Spósob výroby tenzidov podfa vynálezu, klorého podstata spočívá v tom, že sodná alebo draselná sol’ aminomastnej kyseliny sa kondenzuje pn 50 až 160 °C s příslušnou sofou kyseliny monochlórpctovej v molárnom pomere 1:2 až 4 vo vodnoalkoholickom prostředí pri stálej hodnotě pH 9 až 11 za uskutočnenia reakcie v 2 až 20 % koncentrácii príslušnej aminomastnej kyseliny v reakčnej zmesi, pričom reakčný produkt vo formě vofnej kyseliny sa izoluje okyselením zriedenou kyselinou chlorovodíkovou (1:1) na pH 1,2 až 1,8, z ktorého sa po izolácii připraví amónna sof neutralizáciou s hydroxydom amonným, alebo ester zahriatím s 15 až 40 násobným množstvom příslušného bezvodého alkoholu, za súčasného zavádzania plynného chlorovodíka do reakčnej zmesi po dobu 30 až 50 hodin izoláciou esteru desiiláciou.The process for the preparation of the surfactants according to the invention is characterized in that the sodium or potassium salt of the aminobutyric acid is condensed at 50 to 160 ° C with the corresponding monochloroacetic acid salt in a molar ratio of 1: 2 to 4 in a hydroalcoholic medium at a constant pH of 9 to 11 to conduct the reaction at a concentration of 2 to 20% of the corresponding amino fatty acid in the reaction mixture, wherein the free acid reaction product is isolated by acidification with dilute hydrochloric acid (1: 1) to a pH of 1.2 to 1.8, from which Prepare the ammonium salt by neutralization with ammonium hydroxide, or ester by heating with 15 to 40 times the appropriate anhydrous alcohol, while introducing hydrogen chloride gas into the reaction mixture for 30 to 50 hours by isolating the ester by desillation.
Připravené látky predstavujú novů oblast’ v štúdiu komplexónov. Už pri samotnej príprave sa ukázala úplná odlišnost’ v ich chemických a fyzikálnych vlastnostiach oproti doteraz známým derivátom Komplexónu I. Novopripravené látky sa vyznačujú povrchovoaktívnymi vlastnosťami pri zachovaní chelatačných vlastností. Rozšírujú škálu známých amfotenzidov alkylbetatnového typu. Popři širokých možnostiach využitia týchto látok v praxi výhoda vynálezu spočívá aj v dobrých výťažkoch, jednoduchej výrobě a izolácii požadovaných produktov.The prepared substances represent a new area 'in the complexone study. Already in the preparation itself, there was a complete difference in their chemical and physical properties compared with the hitherto known derivatives of Complexon I. The newly prepared substances are characterized by surface-active properties while maintaining chelating properties. They extend the range of known alkyl betatin type amphotensides. In addition to the wide range of uses of these materials in practice, the advantage of the invention is also good yields, easy manufacture and isolation of the desired products.
Příklad 1Example 1
4,0 g (0,019 mol.) aminolaurovej kyseliny sa zneutralizuje s NaHCO3 v 85 ml 70 % etanolu. Pri 80 °C přidá sa k sodnej soli aminolaurovej kyseliny 0,056 mol monochíóroctanu sodného v 55 ml vody a 22 ml 10 % roztoku hydroxidu sodného, aby pH reakčnej zmesi bolo 9 až 11. Reakčná zmes sa zahrieva na vodnom kúpeli za stálého miešania pri 90 °C 24 hodin. Reakčný produkt sa vysuší a priamo použije ako surovina na výrobu detergentov. Reakčný produkt je možno tiež izolovat’ okyselením zriedenou kyselinou chlorovodíkovou (1:1) na pH 1,5. Po odsátí sa produkt premýva na filtri destilovanou vodou až kým filtrát dává neutrálnu reakciu a nereaguje už pozitivně na přítomnost’ halogenu.4.0 g (0.019 mol.) Aminododecanoic acid was neutralized with NaHCO 3 in 85 ml of 70% ethanol. At 80 ° C, 0.056 mol of sodium monochloroacetate in 55 ml of water and 22 ml of 10% sodium hydroxide solution are added to the aminolauric acid sodium salt to bring the pH of the reaction mixture to 9-11. The reaction mixture is heated in a water bath with stirring at 90 °. C 24 hours. The reaction product is dried and used directly as detergent raw material. The reaction product can also be isolated by acidification with dilute hydrochloric acid (1: 1) to pH 1.5. After aspiration, the product is washed on the filter with distilled water until the filtrate gives a neutral reaction and no longer reacts positively to the presence of halogen.
Izolovaná a — amino — (N, N-dioctová) kyselina laurová sa čistí kryštalizáciou zo zmesi kyselina octová — voda (1,5:1).The isolated α-amino- (N, N-diacetic) lauric acid was purified by crystallization from acetic acid-water (1.5: 1).
Výťažok: 90 % teorieYield: 90%
T. t.: 155,5 až 156 °CMp: 155.5-156 ° C
5,0 g (0,015 mol) izolovanej a —amino (N,N — dioctovej) kyseliny laurovej sa zahrieva pod spalným chladičom opatřeným chlórkalciovým uzáverom s 40 násobným množstvom bezvodého etanolu za stálého zavádzania plynného chlorovodíka do reakčnej zmesi po dobu 45 hodin. Po ukončení reakcie sa oddestiluje převážná časť alkoholu, destilačný zbytok sa naleje do pať násobného množstva 1’adovej vody a zneutralizuje s NA2CO3. Vzniklý trietylester a — amino (N,N — dioctovej) kyseliny laurovej sa vy třepe do éteru a izoluje destiláciou.5.0 g (0.015 mol) of isolated α-amino (N, N-di-acetic) lauric acid was heated under an incinerator equipped with a chloro-calcium cap with 40 times the quantity of anhydrous ethanol while continuously introducing hydrogen chloride gas into the reaction mixture for 45 hours. After completion of the reaction, the bulk of the alcohol is distilled off, the residue is poured into five times the amount of 1-ice water and neutralized with NA 2 CO 3 . The resulting α-amino (N, N-diacetic) lauric acid triethyl ester is shaken into ether and isolated by distillation.
Výťažok: 70 % teorieYield: 70%
T. v.: 122 až 124 °C, ηθ 20 — 1,4540 Povrchová aktivita:M.P .: 122 to 124 ° C, η θ 20 - 1.4540
hodnoty povrchového napátia γ [N/m.103] trojsódnej soli a — amino— (N,N —dioctovej) kyseliny laurovej v závislosti na teplote a koncentrácii.surface tension values γ [N / m.10 3 ] of the tri-sodium salt of α-amino- (N, N-diacetic) lauric acid as a function of temperature and concentration.
Koncentr.Conc.
Koncentráciaconcentration
Příklad 2:Example 2:
3,0 g (0,011 mol) aminopalmitovej kyseliny sa zneutralizuje s hydroxidom sódnym v 55 ml 70 % etanolu. Pri 80 °C přidá sa k sodnej soli aminopalmitovej kyseliny 0,033 mol monochlóroctánu sodného v 30 ml vody a 15 ml 9,3 % roztoku hydroxidu sodného, aby pH reakčnej zmesi bolo 9 až 11. Reakčná zmes sa zahrieva na vodnom kúpeli pri 90 °C 14 hodin, keď sa přidá 0,011 mol monochíóroctanu sodného a 20 ml 2 % roztoku hydroxidu sodného a zahrieva sa ďalej ešte 10 hodin pri 90 °C. Reakčný produkt sa vysuší a priamo použije ako surovina pre výrobu detergentov. Reakčný produkt je možno tiež izolovat’ okyselením zriedenou kyselinou chlorovodíkovou (1;) na pH 1,5 a po odsátí sa premýva destilovanou vodou. Izolovaná a — amino — (N,N—dioctová) kyselina palmitová sa čistí kryštalizáciou zo zmesi kyselina octová — voda (1,5:1).3.0 g (0.011 mol) of aminopalmitic acid are neutralized with sodium hydroxide in 55 ml of 70% ethanol. At 80 ° C, 0.033 mol of sodium monochloroacetate in 30 ml of water and 15 ml of 9.3% sodium hydroxide solution are added to the aminopalmitic acid sodium salt to bring the pH of the reaction mixture to 9-11. The reaction mixture is heated in a water bath at 90 ° C. 14 hours when 0.011 mol of sodium monochloroacetate and 20 ml of a 2% sodium hydroxide solution were added and heated at 90 ° C for a further 10 hours. The reaction product is dried and used directly as detergent raw material. The reaction product can also be isolated by acidification with dilute hydrochloric acid (1) to a pH of 1.5 and washed with distilled water after suction. The isolated α-amino- (N, N-diacetic) palmitic acid is purified by crystallization from acetic acid-water (1.5: 1).
Výťažok: 82% teorieYield: 82%
T. t. 155 až 156 °CT. t. Mp 155-156 ° C
Izolovaná a — amino (N,N—dioctová) kyselina palmitová poskytuje neutralizáciou s hydroxidom amonným v molárnom pomere 1:3 trojamónnu sol’ a — amino (N,N—dioctovej) kyseliny palmitovej.The isolated α-amino (N, N-diacetic) palmitic acid provides neutralization with ammonium hydroxide in a 1: 3 molar ratio of the triammonium salt of α-amino (N, N-diacetic) palmitic acid.
Povrchová aktivita:Surface activity:
hodnoty povrchového napátia y [N/m- 10'3] trojsodnej soli a — amino — (N,N — dioctovej) kyseliny palmitovej v závislosti na teplote a koncentráciísurface tension values of y [N / m-10 ' 3 ] trisodium salt of α-amino- (N, N-diacetic) palmitic acid as a function of temperature and concentration
Koncentráciaconcentration
Tenzidy vyrobené týmto sposobom možno pí).užiť ako analytické činidlá, flotačné činidla, katalyzátory, antikorozívne látky, antioxidanty, v energetike, v kozmetike, farmách, chemickom a petrochemickom priemysle, ďalej ako suroviny pre výrobu tergentov, zmákčovadlá, emulgátory a pomocné látky v róznych oblastiach (gumárstve, plastické hmoty, vodoodpudivé úpravy, poťnohospodárstve).Surfactants produced in this manner can be used as analytical agents, flotation agents, catalysts, anticorrosive agents, antioxidants, in the energy, cosmetics, farms, chemical and petrochemical industries, as well as tergent raw materials, wetting agents, emulsifiers and auxiliaries in the in various areas (rubber, plastics, water-repellent treatment, agriculture).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS444877A CS199072B1 (en) | 1977-07-05 | 1977-07-05 | Tenzides based on complexones of monoamines and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS444877A CS199072B1 (en) | 1977-07-05 | 1977-07-05 | Tenzides based on complexones of monoamines and process for preparing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199072B1 true CS199072B1 (en) | 1980-07-31 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS444877A CS199072B1 (en) | 1977-07-05 | 1977-07-05 | Tenzides based on complexones of monoamines and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS199072B1 (en) |
-
1977
- 1977-07-05 CS CS444877A patent/CS199072B1/en unknown
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