DE1262216B - Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agents - Google Patents
Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agentsInfo
- Publication number
- DE1262216B DE1262216B DER43064A DER0043064A DE1262216B DE 1262216 B DE1262216 B DE 1262216B DE R43064 A DER43064 A DE R43064A DE R0043064 A DER0043064 A DE R0043064A DE 1262216 B DE1262216 B DE 1262216B
- Authority
- DE
- Germany
- Prior art keywords
- wetting
- detergents
- agents
- acid
- fatty acid
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 239000003599 detergent Substances 0.000 title claims description 9
- 239000003795 chemical substances by application Substances 0.000 title claims description 8
- 238000009736 wetting Methods 0.000 title claims description 8
- 239000012459 cleaning agent Substances 0.000 title claims description 6
- 230000001804 emulsifying effect Effects 0.000 title claims description 4
- 239000000344 soap Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- -1 alkylammonium ion Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 24
- 244000060011 Cocos nucifera Species 0.000 description 24
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- 150000004665 fatty acids Chemical class 0.000 description 19
- 239000011734 sodium Substances 0.000 description 14
- 159000000000 sodium salts Chemical class 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000004442 acylamino group Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 8
- FUOOLUPWFVMBKG-UHFFFAOYSA-N alpha-amino-isobutyric acid Natural products CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 7
- 239000008399 tap water Substances 0.000 description 7
- 235000020679 tap water Nutrition 0.000 description 7
- 239000013065 commercial product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical class C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 3
- XFLXJCCWLJSPFC-QXMHVHEDSA-N 2-methyl-2-[[(z)-octadec-9-enoyl]amino]propanoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NC(C)(C)C(O)=O XFLXJCCWLJSPFC-QXMHVHEDSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 238000005303 weighing Methods 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
Landscapes
- Chemical & Material Sciences (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. α.:Int. α .:
Nummer
Aktenzeichen:
Anmeldetag:
Auslegetag:number
File number:
Registration date:
Display day:
D 06 mD 06 m
Deutsche Kl.: So-German class: So-
1262216
R 43064IV c/8 ο 15. April 1966 7. März 19681262216
R 43064IV c / 8 ο April 15, 1966 March 7, 1968
Es sind Wasch-, Netz-, Dispergier- und Egalisiermittel bekannt, deren wesentlicher Bestandteil Verbindungen der FormelDetergents, wetting agents, dispersants and leveling agents are known, the essential constituent of which are compounds the formula
R1 — CO — NR2 — CHR3 — COOMeR 1 - CO - NR 2 - CHR 3 - COOMe
sind, worin R1 einen längeren aliphatischen Rest und R2 und R3 entweder Wasserstoff oder andere organische Reste bedeuten. In der Praxis haben sich insbesondere die Abkömmlinge des Sarkosins, also des N-Methylglycins, bewährt. Sie werden vorzugsweise als Netz- und Egalisiermittel und als kosmetische Reinigungsmittel verwendet. In hartem Wasser verlieren sie ihr Wasch-, Netz- und Schaumvermögen zum großen Teil, obwohl sie als verhältnismäßig härteunempfindlich beschrieben worden sind. Sie haben daher als Wasch- und Reinigungsmittel für den Haushalt keine Bedeutung erlangt, werden jedoch zusammen mit Enthärtungsmitteln als industrielle Textilwaschmittel benutzt.are, where R 1 is a longer aliphatic radical and R 2 and R 3 are either hydrogen or other organic radicals. In practice, the derivatives of sarcosine, i.e. N-methylglycine, have proven particularly useful. They are preferably used as wetting and leveling agents and as cosmetic cleaning agents. In hard water they lose their washing, wetting and foaming properties to a large extent, although they have been described as relatively insensitive to hardness. They have therefore gained no importance as household detergents and cleaning agents, but are used together with softening agents as industrial laundry detergents.
Es wurde nun gefunden, daß Salze von Acylaminosäuren der allgemeinen Formel
Grenzflächenaktive Verbindungen als Wasch- und Reinigungsmittel sowie als Netz-,
Dispergier-, Emulgier-
und EgalisiermittelIt has now been found that salts of acylamino acids of the general formula interface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying
and leveling agents
Anmelder:Applicant:
Röhm & Haas G. m. b. H.,Rohm & Haas G. m. B. H.,
6100 Darmstadt, Mainzer Str. 426100 Darmstadt, Mainzer Str. 42
Als Erfinder benannt:Named as inventor:
Dr. Dieter Neher, 6100 Darmstadt; Dr. Günter Schröder, 6101 Ober-Ramstadt-Eiche; Dr. Hans Kraus,Dr. Dieter Neher, 6100 Darmstadt; Dr. Günter Schröder, 6101 Ober-Ramstadt-Eiche; Dr. Hans Kraus,
Heinrich Kniese, 6100 DarmstadtHeinrich Kniese, 6100 Darmstadt
X/X /
R1 — CO — NR2 — C — COOMeR 1 - CO - NR 2 - C - COOMe
worin R1 einen hydrophoben gesättigten oder ungesättigten aliphatischen Rest mit 7 bis 21 Kohlenstoffatomen, R2 Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffatomen, R3 und R4 gleiche oder verschiedene Alkylreste mit 1 bis 4 Kohlenstoffatomen, die auch zu einem Ring geschlossen sein können, oder Aryl- bzw. Aralkylreste und Me ein Äquivalent eines Alkali- oder Erdalkalimetallions, ein Ammonium-, Alkylammonium- oder Alkylolammoniumion bedeutet, mit ausgezeichnetem Erfolg als grenzflächenaktive Stoffe verwendet werden können.wherein R 1 is a hydrophobic, saturated or unsaturated aliphatic radical with 7 to 21 carbon atoms, R 2 is hydrogen or an alkyl radical with 1 to 4 carbon atoms, R 3 and R 4 are identical or different alkyl radicals with 1 to 4 carbon atoms, which are also closed to form a ring or aryl or aralkyl radicals and Me is an equivalent of an alkali or alkaline earth metal ion, an ammonium, alkylammonium or alkylolammonium ion, can be used with excellent success as surfactants.
Typische Acylreste R1 — CO — sind die Reste der Stearinsäure, Palmitinsäure, ölsäure, Linolsäure, Linolensäure, Kokosfettsäuren, Laurinsäure, Ricinolsäure oder Hydroxystearinsäure sowie der Gemische dieser Säuren. Beispiele für die den Acylaminosäuren zugrunde liegenden Aminosäuren sind a-(Methylamino)-isobuttersäure, a-Methyl-a-aminobuttersäure, l-Amino-cyclohexancarbonsäure oder a-Phenyl-a-aminopropionsäure. Besondere Erwähnung verdienen die Acylderivate der a-Aminoisobuttersäure, da diese Säure nicht nur besonders leicht zugänglich ist, sondern auch zu besonders wertvollen grenzflächenaktiven Verbindungen führt.Typical acyl radicals R 1 - CO - are the radicals of stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, coconut fatty acids, lauric acid, ricinoleic acid or hydroxystearic acid and mixtures of these acids. Examples of the amino acids on which the acylamino acids are based are a- (methylamino) isobutyric acid, a-methyl-a-aminobutyric acid, l-amino-cyclohexanecarboxylic acid or a-phenyl-a-aminopropionic acid. The acyl derivatives of α-aminoisobutyric acid deserve special mention, as this acid is not only particularly easily accessible, but also leads to particularly valuable surface-active compounds.
Die angegebenen Acylaminosäuren sind wesentlich weniger härteempfindlich als die bisher bekannten Verbindungen, die 1 oder 2 Wasserstoffatome in der α-Stellung zur Carboxylgruppe tragen. Die nachfolgenden Vergleichsversuche, die nach bekannten Methoden, insbesondere DIN-Vorschriften, durchgeführt worden sind, bestätigen dies an Hand des Schaumvermögens und der Netzkraft.The specified acylamino acids are much less sensitive to hardness than those previously known Compounds which have 1 or 2 hydrogen atoms in the α-position to the carboxyl group. the subsequent comparative tests carried out according to known methods, in particular DIN regulations confirm this on the basis of the foaming power and the wetting power.
TensidSurfactant
C17H33CO - NH - C(CH3J2 - CO2Na Desgleichen mit 30% SeifeC 17 H 33 CO - NH - C (CH 3 J 2 - CO 2 Na Same with 30% soap
— CO — C17H33
R - CO - N(CH3) - CH2 - CO2Na
(R = C7 bis C17, Handelsprodukt)- CO - C 17 H 33
R - CO - N (CH 3 ) - CH 2 - CO 2 Na (R = C 7 to C 17 , commercial product)
Aussehen derAppearance of
Lösung inSolution in
Wasser vonWater from
30° dH.30 ° dH.
fast klar leicht opakalmost clear, slightly opaque
schwach opak stark trübslightly opaque, very cloudy
809 517/607809 517/607
(in Zentimeter
vollentsalztes
WasserFoam v
(in centimeters
fully desalinated
water
Schaumhöhe)
Leitungswasser
von 15° dH.He likes
Foam height)
tap water
of 15 ° dH.
(Untersinkzeit
vollentsalztes
WasserNetzwi
(Sinking time
fully desalinated
water
in Sekunden)
Leitungswasser
von 15° dH.remediation
in seconds)
tap water
of 15 ° dH.
(R2 = C7-C17-GCmISCh)R - CO - NH- - C (CH 3 ) I 2 - CO 2 Na
(R 2 = C 7 -C 17 -GCmISCh)
(R = C7-C17) mit 25% SeifeR-CO-N (CH 3 ) -C (CH 3 J 2 -CO 2 Na
(R = C 7 -C 17 ) with 25% soap
(R2 = C7-C17, Handelsprodukt)R - CO - N (CH 3 ) - CH 2 - CO 2 Na
(R 2 = C 7 -C 17 , commercial product)
Überraschenderweise wird die Härtebeständigkeit der cc-disubstituierten Acylaminosäuren durch einen Zusatz von Seife im allgemeinen nicht beeinträchtigt, sondern in einigen Fällen sogar noch erhöht Diesen Effekt weisen nur die Verbindungen gemäß der Erfindung auf. Dadurch wird die unmittelbare Verwendung von mit Seifen vermischten Rohprodukten sowie die Anwendung in seifehaltigen Flotten ermöglicht. Die in α-Stellung Wasserstoff tragenden Acylaminosäuren dürfen dagegen, wie aus der deutschen Auslegeschrift 1 127 359 (Spalte 5, 2. Absatz) hervorgeht, keine Seifen enthalten, wenn sie in hartem Wasser verwendet werden.Surprisingly, the hardness resistance of the cc-disubstituted acylamino acids by a Soap addition generally does not affect it, but in some cases actually increases it Only the compounds according to the invention have an effect. This makes immediate use of raw products mixed with soaps as well as the use in soap-containing liquors. The acylamino acids carrying hydrogen in the α-position may, however, as from the German Auslegeschrift 1 127 359 (column 5, 2nd paragraph) does not contain soaps if they be used in hard water.
Ein weiterer Vorteil bei der Verwendung der ct-disubstituierten Acylaminosäuren liegt darin, daß sie besonders hautschonend sind. Diese Eigenschaft ist nicht nur für die Anwendung in Hand- und Körperreinigungsmitteln, Zahnpasten und Shampoos von Bedeutung, sondern auch überall da, wo eine häufige Berührung der Haut mit grenzflächenaktiven Stoffen und deren wäßrigen Flotten vorkommt, z. B. beim Einfüllen und Abwiegen des Mittels oder beim Hantieren in Waschflotten oder mit davon benetzten Textilien und Gegenständen.Another advantage of using the ct-disubstituted acylamino acids is that they are particularly kind to the skin. This property is not just for hand and hand use Body cleansers, toothpastes and shampoos matter, but also wherever one frequent contact of the skin with surface-active substances and their aqueous liquors occurs, e.g. B. when filling and weighing the agent or when handling in or with washing liquors Textiles and objects.
Auf Grund dieser Eigenschaften werden die a-disubstituierten Acylaminosäuren mit Erfolg in kosmetischen Wasch- und Reinigungsmitteln, als Textilwaschmittel, besonders für die Wollwäsche, als Geschirrspülmittel, als Netz-, Dispergier-, Emulgier- und Egalisiermittel und allgemein in allen Fällen verwandt, wo hautschonende und härtebeständige Tenside gebraucht werden.Because of these properties, the a-disubstituted acylamino acids are used successfully in cosmetic products Detergents and cleaning agents, as laundry detergents, especially for wool washing, as dishwashing detergents, as wetting, dispersing, emulsifying and leveling agents and generally in all cases used where skin-friendly and hardness-resistant surfactants are needed.
Die Salzbildung kann auch in der Waschflotte vorgenommen werden, indem man die freien Säuren und die erforderlichen basischen Verbindungen getrennt in die Flotte gibt.The salt formation can also be done in the wash liquor by removing the free acids and the required basic compounds are separately in the liquor.
Zur Herstellung der a-disubstituierten Acylaminosäuren setzt man zweckmäßig ein Salz der entsprechenden a-disubstituierten Aminosäure mit einem geeigneten Acylierungsmittel, vorzugsweise einem Fettsäurechlorid, um. Die Verbindungen können jedoch auch durch Verseifen der entsprechenden Acylaminonitrile erhalten werden. Die Herstellung der Verbindungen ist nicht Gegenstand der Erfindung.To prepare the a-disubstituted acylamino acids, it is expedient to use a salt of the corresponding a-disubstituted amino acid with a suitable acylating agent, preferably a fatty acid chloride, around. However, the compounds can also be prepared by saponifying the corresponding acylaminonitriles can be obtained. The preparation of the compounds is not the subject of the invention.
35 Bestimmung der Waschwirkung
a) Mit Baumwolle35 Determination of detergency
a) With cotton
Künstlich angeschmutztes Baumwolltestgewebe wurde in einer Laborwaschmaschine vom Typ Launder-Ometer bei 30 auf 60° C ansteigender Flottentemperatur zweimal gewaschen. Die Waschflotte enthielt bei allen Versuchen mit Ausnahme des Blindversuchs 1 g Tensid pro Liter Leitungswasser von 15° dH. Nach jedem Waschgang wurde der Aufhellungseffekt durch photoelektrische Messung des Reflektionsgrades in Prozent eines Weißstandards ermitteltArtificially soiled cotton test fabric was placed in a Launder-Ometer washed twice at a liquor temperature increasing to 60 ° C. The wash liquor contained in all tests, with the exception of the blind test, 1 g of surfactant per liter of tap water from 15 ° dH. After each wash, the lightening effect was determined by photoelectric measurement of the Degree of reflection determined as a percentage of a white standard
Waschflotte mit 1 gfl des angegebenen Tensids in Leitungswasser von 15= dH.Washing liquor with 1 gfl of the specified surfactant in tap water of 15 = dH.
Reflektionsgrad in Prozent
nach einer Wäsche nach zwei WaschenDegree of reflection in percent
after one wash after two washes
Blindversuch ohne Tensid Blind test without surfactant
R — CO — NH — C(CHa)2 — CO2NaR - CO - NH - C (CHa) 2 - CO 2 Na
R = Alkylreste mit 7 bis 17 C-Atomen Kokosfettsäure-N-{carboxyisopropyl)-amid, Na-SaIz R = alkyl radicals with 7 to 17 carbon atoms coconut fatty acid N- {carboxyisopropyl) amide, Na-SaIz
Gemisch aus 70% Kokosfettsäure-N-(carboxyisopropyl)-amid, Na-SaIz, 30% Kokosfettsäure, Na-SaIz Mixture of 70% coconut fatty acid N- (carboxyisopropyl) amide, sodium salt, 30% coconut fatty acid, sodium salt
Gemisch aus 75% R — CO — N(CH3) —C(CHy2 — CO2Na Kokosfettsäure-N-methyl-N-(carboxyisopropyl)-amid, Na-SaIz, 25% Na-SaIz der Kokosfettsäure Mixture of 75% R - CO - N (CH 3 ) - C (CHy 2 - CO 2 Na coconut fatty acid-N-methyl-N- (carboxyisopropyl) amide, sodium salt, 25% sodium salt of coconut fatty acid
Vergleichsversuch mit R — CO — N(CH3) — CH2 — CO2Na Kokosfettsäuresarcosid, Na-SaIz (Handelsprodukt) Comparison test with R - CO - N (CH 3 ) - CH 2 - CO 2 Na Coconut fatty acid sarcoside, Na salt (commercial product)
23,023.0
24,424.4
5 6 5 6
b) Mit Wolle Künstlich angeschmutztes Wolltestgewebe wurde wie unter a) beschrieben zweimal, jedoch bei 30° C, gewaschen.b) Artificially soiled wool test fabric was washed twice as described under a), but at 30.degree.
Blindversuch ohne Tensid Blind test without surfactant
R — CO — NH — C(CH3)S2 — CO2Na Kokosfettsäure-N-(carboxyisopropyl)-amid, Na-SaIz R - CO - NH - C (CH 3 ) S 2 - CO 2 Na Coconut fatty acid N- (carboxyisopropyl) amide, Na salt
Gemisch aus etwa 75% Kokosfettsäure-N-methyl-N-(carboxyisopropyl)-amid, Na-SaIz, etwa 25% Na-SaIz der Kokosfettsäure ...Mixture of about 75% coconut fatty acid-N-methyl-N- (carboxyisopropyl) -amide, Na salt, about 25% Na salt of coconut fatty acid ...
Vergleichsversuch mit Kokosfettsäuresarcosid (Handelsprodukt) ..Comparative experiment with coconut fatty acid sarcoside (commercial product).
Beständigkeit gegen Wasserhärte nach DIN 53 905Resistance to water hardness according to DIN 53 905
5 ml einer 5%igen Lösung eines Tensids in vollentsalztem Wasser wurden in einem Reagenzglas (DIN 13 395, 30 mm Durchmesser)mit Wasser von 30° dRauf 50 ml aufgefüllt. Nach lOmaligem Umschütteln blieb die Probe 1 Stunde bei 25° C stehen und wurde dann beurteilt.5 ml of a 5% solution of a surfactant in deionized water were placed in a test tube (DIN 13 395, 30 mm diameter) made up to 50 ml with water at 30 °. After shaking 10 times, the sample remained Stand for 1 hour at 25 ° C and was then assessed.
TensidlösungSurfactant solution
AussehenAppearance
C17H33 — CO — NH — C(CH3J2 — CO2NaC 17 H 33 - CO - NH - C (CH 3 J 2 - CO 2 Na
ölsäure-N-{carboxyisopropyl)-amid, Na-SaIz oleic acid-N- (carboxyisopropyl) -amide, sodium salt
Gemisch aus etwa 40% Ulsäure-N-(carboxyisopropyl)-amid, Na-SaIz, 60% Natrium· oleat Mixture of about 40% acid-N- (carboxyisopropyl) -amide, sodium salt, 60% sodium oleat
Gemisch aus etwa 70% R — CO — NH — C(CH3J2 — CO2Na Kokosfettsäure-N-(carboxyisopropyl)-amid, Na-SaIz, 30% Na-SaIz der Kokossäure Mixture of about 70% R - CO - NH - C (CH 3 J 2 - CO 2 Na coconut fatty acid-N- (carboxyisopropyl) -amide, sodium salt, 30% sodium salt of coconut acid
r—\ / NH CO C17H33 r- \ / NH CO C 17 H 33
L-/^ CO2NaL - / ^ CO 2 Na
Ulsäure-N-il-carboxycyclopentyty-amid, Na-SaIz Ulic acid-N-il-carboxycyclopentyty-amide, Na-Salz
R — CO — N(CH3) — CH2 — CO2Na
Kokosfettsäuresarcosid (Handelsprodukt) R - CO - N (CH 3 ) - CH 2 - CO 2 Na
Coconut fatty acid sarcoside (commercial product)
fast klar
opak
leicht opakalmost clear
opaque
slightly opaque
schwach opak
stark trübslightly opaque
very cloudy
Bestimmung des Schaumvermögens 1250 ml einer 0,08%igen Lösung des Tensids inDetermination of the foaming power 1250 ml of a 0.08% solution of the surfactant in
125 mm durch einen mit 2850 U/min rotierenden Propellerrührer aufgeschäumt. Nach 1 Minute wurde vollentsalztem Wasser einerseits und in Wasser von abgeschaltet und nach einer weiteren halben Minute 15° dH. andererseits wurden in einem graduierten 45 die Schaumhöhe in Zentimeter gemessen. Die Tem-Glasstutzen mit einem lichten Durchmesser von peratur der Meßlösung betrug 2O0C.125 mm foamed by a propeller stirrer rotating at 2850 rpm. After 1 minute, deionized water was switched off on the one hand and in water from and after another half a minute 15 ° dH. on the other hand, the foam height was measured in centimeters in a graduated 45. The Tem-glass nozzle with an internal diameter of the measuring solution temperature was 2O 0 C.
Bestimmung der Netzwirkung nach DIN 54 901Determination of the wetting effect according to DIN 54 901
Ein rundes Stück rohen Baumwollgewebes wurde in eine 0,l%ige Lösung eines Netzmittels in vollentsalztem Wasser einerseits und in Leitungswasser andererseits eingehängt und die Zeit bis zum Untersinken des Stoffläppchens gemessen. Die Netzmittellösung hatte eine Temperatur von 20 bis 25° C.A round piece of raw cotton fabric was in a 0.1% solution of a wetting agent in deionized Water on the one hand and in tap water on the other hand, and the time it takes to sink below measured on the cloth flap. The wetting agent solution had a temperature of 20 to 25 ° C.
Entgegen der DIN-Vorschrift wurde die Zeit bis zum Untersinken in einer 0,l%igen Lösung als Vergleichszahl verwendet, während nach der DIN-Vorschrift die Netzmittelkonzentration bei einer Sinkzeit von 100 Sekunden angegeben wird.Contrary to the DIN regulation, the time to sink in a 0.1% solution was used as Comparative number used, while according to the DIN regulation, the wetting agent concentration during a sinking time of 100 seconds is specified.
in vollentsalztem WasserSinking time
in demineralized water
in Leitungswasser von
15° dH.in seconds
in tap water of
15 ° dH.
Gemisch aus etwa 75% Kokosfettsäure-N-(carboxyisopropyl)-
methylamid, Na-SaIz, 25% Kokosfettsäure, Na-SaIz
Vergleichsversuch mit Kokosfettsäuresarcosid Coconut fatty acid N- (carboxyisopropyl) amide, Na salt
Mixture of about 75% coconut fatty acid-N- (carboxyisopropyl) -
methylamide, sodium salt, 25% coconut fatty acid, sodium salt
Comparative experiment with coconut fatty acid sarcoside
16
2416
16
24
16
7012th
16
70
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER43064A DE1262216B (en) | 1966-04-15 | 1966-04-15 | Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agents |
| DE19661543829 DE1543829A1 (en) | 1966-04-15 | 1966-05-24 | Creation of hard-wearing surface-active connections |
| FR99777A FR1519053A (en) | 1966-04-15 | 1967-03-22 | New surfactant compounds insensitive to water hardness and their preparation process |
| GB1687167A GB1130480A (en) | 1966-04-15 | 1967-04-12 | Acylated amino-carboxylic acid derivatives and their use as surfactants |
| NL6705232A NL6705232A (en) | 1966-04-15 | 1967-04-13 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER43064A DE1262216B (en) | 1966-04-15 | 1966-04-15 | Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agents |
| DER0043327 | 1966-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1262216B true DE1262216B (en) | 1968-03-07 |
Family
ID=25991966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER43064A Pending DE1262216B (en) | 1966-04-15 | 1966-04-15 | Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agents |
| DE19661543829 Pending DE1543829A1 (en) | 1966-04-15 | 1966-05-24 | Creation of hard-wearing surface-active connections |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543829 Pending DE1543829A1 (en) | 1966-04-15 | 1966-05-24 | Creation of hard-wearing surface-active connections |
Country Status (3)
| Country | Link |
|---|---|
| DE (2) | DE1262216B (en) |
| GB (1) | GB1130480A (en) |
| NL (1) | NL6705232A (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013149019A1 (en) | 2012-03-30 | 2013-10-03 | Givaudan S.A. | N-acylated methionine derivatives as food flavouring compounds |
| CN104219966B (en) * | 2012-03-30 | 2019-05-28 | 奇华顿股份有限公司 | N- sulphonyl-amino acid derivative as food fragrance compound |
| SG11201405295WA (en) * | 2012-03-30 | 2014-11-27 | Givaudan Sa | N-acyl-amino acid derivatives for improvement of the flavour profile edible|compositions |
| WO2013148997A1 (en) * | 2012-03-30 | 2013-10-03 | Givaudan, S.A. | N-acylated 1 - aminocycloalkyl carboxylic acids as food flavouring compounds |
| CN104219964B (en) | 2012-03-30 | 2016-09-21 | 奇华顿股份有限公司 | N-acyl-proline derivant as food fragrance compound |
| WO2013148991A1 (en) | 2012-03-30 | 2013-10-03 | Givaudan S.A. | N-acyl derivatives of gamma amino - butyric acid and and beta alanine as food flavouring compounds |
| CA2868077C (en) * | 2012-03-30 | 2020-09-29 | Givaudan S.A. | Powder flavour composition |
| WO2015050536A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | N-acylated 2-aminoisobutyric acid compounds and flavour compositions containing them |
| US10674755B2 (en) | 2013-10-02 | 2020-06-09 | Givaudan S.A. | Organic Compounds |
| CN105592720B (en) | 2013-10-02 | 2020-07-07 | 奇华顿股份有限公司 | Organic compounds with taste-improving properties |
| WO2015050535A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| CN105658089B (en) | 2013-10-02 | 2019-07-09 | 奇华顿股份有限公司 | Organic compound |
| US10834950B2 (en) | 2013-10-02 | 2020-11-17 | Givaudan S.A. | Organic compounds |
| WO2015048990A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
-
1966
- 1966-04-15 DE DER43064A patent/DE1262216B/en active Pending
- 1966-05-24 DE DE19661543829 patent/DE1543829A1/en active Pending
-
1967
- 1967-04-12 GB GB1687167A patent/GB1130480A/en not_active Expired
- 1967-04-13 NL NL6705232A patent/NL6705232A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1130480A (en) | 1968-10-16 |
| DE1543829A1 (en) | 1970-01-02 |
| NL6705232A (en) | 1967-10-16 |
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