DE1493814B2 - USE OF AMINOCARBONIC ACIDS AS VISCOSITY INCREASING AGENTS - Google Patents
USE OF AMINOCARBONIC ACIDS AS VISCOSITY INCREASING AGENTSInfo
- Publication number
- DE1493814B2 DE1493814B2 DE19631493814 DE1493814A DE1493814B2 DE 1493814 B2 DE1493814 B2 DE 1493814B2 DE 19631493814 DE19631493814 DE 19631493814 DE 1493814 A DE1493814 A DE 1493814A DE 1493814 B2 DE1493814 B2 DE 1493814B2
- Authority
- DE
- Germany
- Prior art keywords
- increasing agents
- viscosity increasing
- carbon atoms
- viscosity
- acids
- 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.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 title description 5
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- -1 alkaline earth metal salts Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical class CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/06—Solidifying liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Description
CNCN
R2 COOHR 2 COOH
worin R1 einen gesättigten Kohlenwasserstoffrest mit einer Kettenlänge von 8 bis 22 Kohlenstoffatomen, und R2 einen gesättigten, 1 bis 10 Kohlenstoffatome enthaltenden Kohlenwasserstoffrest bedeuten, als viskositätserhöhende Mittel für unpolare organische Lösungsmittel.wherein R 1 is a saturated hydrocarbon radical with a chain length of 8 to 22 carbon atoms, and R 2 is a saturated hydrocarbon radical containing 1 to 10 carbon atoms, as viscosity-increasing agents for non-polar organic solvents.
Als Verdickungsmittel für organische Lösungsmittel waren bisher nur Seifen (Alkali- oder Erdalkalimetallsalze von Fettsäuren) bekannt, Gemische, die eine solche Seife enthalten, oder Verbindungen bzw. Gemische, die erst nach Zusatz von Alkali ihre verfestigende Wirkung entfalten. Ein Nachteil dieser Verdickungsmittel liegt darin, daß die verdickten Lösungsmittel trüb sind. In einem trüben Medium sind aber Lösungsvorgänge weit schwieriger zu verfolgen und bestimmte optische Messungen nicht mehr durchführbar. Auch können in einem trüben Lösungsmittel Verunreinigungen nicht sofort erkannt werden1. Ein anderer, wesentlich schwerer wiegender Nachteil der vorbekannten Mittel aber ist der, daß diese anorganische Bestandteile (Alkali- oder Erdalkalimetalle) enthalten, die unter Umständen (z. B. bei der Verbrennung) zu unliebsamen Rückständen führen können.The only known thickeners for organic solvents so far have been soaps (alkali or alkaline earth metal salts of fatty acids), mixtures containing such a soap, or compounds or mixtures which develop their strengthening effect only after the addition of alkali. A disadvantage of these thickeners is that the thickened solvents are cloudy. In a cloudy medium, however, solution processes are far more difficult to follow and certain optical measurements can no longer be carried out. Also, impurities cannot be recognized immediately in a cloudy solvent 1 . Another, much more serious disadvantage of the previously known agents is that they contain inorganic constituents (alkali or alkaline earth metals) which under certain circumstances (e.g. during incineration) can lead to undesirable residues.
Diese Nachteile treten nicht auf, wenn als viskositätserhöhende Mittel für unpolare organische Lösungsmittel erfindungsgemäß Aminocarbonsäuren der allgemeinen FormelThese disadvantages do not occur when used as viscosity-increasing agents for non-polar organic solvents according to the invention aminocarboxylic acids of the general formula
CH2NH2 CH 2 NH 2
COOHCOOH
worin R1 einen gesättigten Kohlenwasserstoffrest mit einer Kettenlänge vori"8 bis 22 Kohlenstoffatomen und R2 einen gesättigten, 1 bis 10 Kohlenstoffatome enthaltenden Kohlenwasserstoffrest bedeuten, verwendet werden.in which R 1 is a saturated hydrocarbon radical having a chain length of 8 to 22 carbon atoms and R 2 is a saturated hydrocarbon radical containing 1 to 10 carbon atoms.
Als RrReste in Verbindungen der Formel I kommen in Betracht: Verzweigte oder unverzweigte rgesättigte Kohlenwasserstoffreste mit Kettenlängen von 8 bis 22 Kohlenstoffatomen. Beispiele solcher Alkylgruppen sind: Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tetradecyl, Hexadecyl, Octadecyl, Eicosyl, Docosyl.Possible R r radicals in compounds of the formula I are: Branched or unbranched r-saturated hydrocarbon radicals with chain lengths of 8 to 22 carbon atoms. Examples of such alkyl groups are: octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl.
Als R2-Reste kommen verzweigte oder unverzweigte gesättigte Kohlenwasserstoffreste mit Kettenlängen von 1 bis 10 Kohlenstoffatomen in Betracht. Bevorzugt bedeutet R2 eine niedere verzweigte oder unverzweigte Alkylgruppe mit 1 bis 8 Kohlenstoffatomen, wie Methyl, Äthyl, Propyl, η-Butyl, Isobutyl, n-Pentyl, Isoamyl, Hexyl, Heptyl, Octyl.Suitable R 2 radicals are branched or unbranched saturated hydrocarbon radicals with chain lengths of 1 to 10 carbon atoms. R 2 preferably denotes a lower branched or unbranched alkyl group having 1 to 8 carbon atoms, such as methyl, ethyl, propyl, η-butyl, isobutyl, n-pentyl, isoamyl, hexyl, heptyl, octyl.
Die Aminocarbonsäuren der Formel I können auf an sich bekannte Art (vgl. z. B. die britische Patentworin R3 eine veresterte Carboxylgruppe, R1' einenThe aminocarboxylic acids of the formula I can be in a manner known per se (cf., for example, the British patent where R 3 is an esterified carboxyl group, R 1 'is a
ίο gesättigten oder ungesättigten Kohlenwasserstoffrest
mit einer Kettenlänge von 8 bis 22 Kohlenstoffatomen und R2' einen gesättigten oder ungesättigten, 1 bis
10 Kohlenstöffatome enthaltenden Kohlenwasserstoffrest bedeuten, einerseits zwecks Überführung der
Cyan- in die Aminomethylgruppe mit einem Reduktionsmittel und andererseits zwecks Freisetzung der
veresterten Carboxylgruppe mit einem hydrolysierenden Mittel behandelt.
Die als Ausgangsstoffe verwendeten Verbindungen der Formel II können aus Cyanessigester leicht wie
folgt erhalten werden: Das Natriumsalz des Cyanessigesters
wird in Gegenwart von überschüssigem Cyanessigester in Alkohol mit einem RZ-Halogenid, z. B.
Dodecylbromid, umgesetzt. In die erhaltenen monosubstituierten Cyanessigester kann hierauf auf entsprechende
Art ein zweiter Substituent eingeführt werden, z. B. eine Allylgruppe durch Umsetzung mit AlIyI-bromid.
Die Aminocarbonsäuren der Formel I sind kristalline, in Wasser, kaltem Äthanol, Methanol oder Isopropanol
sehr wenig lösliche Verbindungen. Ihr Schmelzpunkt ist, da stark yonder Aufheizgeschwindigkeit
abhängig, wenig charakteristisch. Meist sintern die Verbindungen bis TO?C"vor dem eigentlichen
Schmelzen. Die Verbindungen ertragen in Substanz Temperaturen von mehr als 500C nur während kurzer
Zeit. Beim Erhitzen auf 1000C und darüber entstehen klebrige Polymerisate.ίο a saturated or unsaturated hydrocarbon radical with a chain length of 8 to 22 carbon atoms and R 2 'mean a saturated or unsaturated hydrocarbon radical containing 1 to 10 carbon atoms, on the one hand for the purpose of converting the cyano into the aminomethyl group with a reducing agent and on the other hand for the purpose of releasing the esterified carboxyl group with treated with a hydrolyzing agent.
The compounds of formula II used as starting materials can easily be obtained from cyanoacetate as follows: The sodium salt of cyanoacetate is in the presence of excess cyanoacetate in alcohol with an RZ halide, e.g. B. dodecyl bromide implemented. A second substituent can then be introduced into the monosubstituted cyanoacetic ester obtained in a corresponding manner, e.g. B. an allyl group by reaction with AlIyI bromide.
The aminocarboxylic acids of the formula I are crystalline compounds which are very sparingly soluble in water, cold ethanol, methanol or isopropanol. Their melting point is not very characteristic because it is strongly dependent on the heating rate. The compounds usually sinter up to TO "C" before the actual melting. The compounds in substance endure temperatures of more than 50 ° C. only for a short time. When heated to 100 ° C. and above, sticky polymers are formed.
Die Aminocarbonsäuren der Formel I wirken viskositätserhöhend. Insbesondere vermögen sie unpolare organische Lösungsmittel, wie Benzin, Petroläther jeglichen SiedebereichSj Tetrachlorkohlenstoff, Benzol usw. zu Gelen zu verdicken. Ein deutlicher viskositätserhöhender Effekt ist bereits bei Konzen-The aminocarboxylic acids of the formula I have a viscosity-increasing effect. In particular, they are capable of non-polar ones organic solvents such as gasoline, petroleum ether, any boiling range Sj carbon tetrachloride, Benzene etc. to thicken into gels. A clear viscosity-increasing effect is already evident with
,45 trationen (Gewicht/Volurnen) in der Größenordnung von 1 Promille zu beobachten. Für praktische Zwecke wird meist eine Konzentration in der Größenordnung von rund 0,5 bis einigen wenigen Prozent genügen.45 trations (weight / volume) in the order of magnitude of 1 per mille were observed. For practical purposes A concentration of around 0.5 to a few percent will usually be sufficient.
Die Viskosität der erhaltenen Lösungen bzw. Gele ist in der Regel nur wenig-temperaturabhängig.The viscosity of the solutions or gels obtained is generally only slightly temperature-dependent.
Der Verdickungseffekt der erfindungsgemäß erhältlichen Aminocarbonsäuren kann durch Zugabe geeigneter Mittel, z. B. von 2-Amino-2-methyl-propandiol-(l,3), aufgehoben werden.The thickening effect of the aminocarboxylic acids obtainable according to the invention can be achieved by adding suitable Medium, e.g. B. of 2-amino-2-methyl-propanediol- (l, 3), To get picked up.
In den unpolaren; tief siedenden organischen Lösungsmitteln entfalten die Verfahrensprodukte ihren gelierenden Effekt zum Teil, erst nach längerem Kochen. Um in solchen Fällen rasch zu einem Gel zu kommen, empfiehlt sich folgendes Vorgehen: Das kristalline Verdickungsmittel wird in Benzol kurz aufgekocht, wobei ein klares Gel entsteht. Dieses Gel wird dann unter vermindertem Druck bei etwa 40 bis 60° C eingedampft. Man erhält so ein amorphes Produkt mit erhöhter Gelierfähigkeit, das nun auch andere Lösungsmittel sehr rasch, z. B. bereits nach kurzem Aufkochen, zum Gelieren bringt.In the non-polar; low-boiling organic solvents the process products partially develop their gelling effect, only after a long time Cook. In order to get a gel quickly in such cases, the following procedure is recommended: The crystalline Thickener is briefly boiled in benzene to form a clear gel. This gel will then evaporated under reduced pressure at about 40 to 60 ° C. An amorphous product is obtained in this way increased gelling ability, which now also other solvents very quickly, z. B. already after a short boil, gel.
Auf Grund ihrer viskositätserhöhenden Wirkung können die Aminocarbonsäuren der Formel I als Ver-Due to their viscosity-increasing effect, the aminocarboxylic acids of the formula I can be used as a
dickungs- bzw. Geliermittel auf den verschiedensten Gebieten Verwendung finden, z. B. als Verdickungs- bzw. Geliermittel für unpolare organische Lösungsmittel in der pharmazeutischen und kosmetischen Industrie; ferner für unpolare organische Lösungsmittel, die für Druckfarben, Anstrichfarben, Lacke, Schmieröle, Fleckenreinigungsmittel oder als Zusätze zu leicht brennbaren Treibstoffen verwendet werden.thickening or gelling agents are used in a wide variety of areas, e.g. B. as thickening or gelling agents for non-polar organic solvents in pharmaceutical and cosmetic Industry; also for non-polar organic solvents that are used for printing inks, paints, varnishes, Lubricating oils, stain cleaners or as additives to highly flammable fuels.
Im folgenden werden einige Anwendungsmöglichkeiten beschrieben:Some possible uses are described below:
a) 1 bis 10 g «-n-Hexadecyl-a-propyl-^-aminopropionsäure werden in 1000 g dünnflüssigem Paraffinöl unter Rühren so lange erwärmt, bis die Lösung vollkommen klar ist. Das so erhaltene viskose öl eignet sich z. B. für Schmierzwecke.a) 1 to 10 g «-n-hexadecyl-a-propyl - ^ - aminopropionic acid are heated in 1000 g of low-viscosity paraffin oil with stirring until the solution is complete it's clear. The viscous oil obtained in this way is suitable, for. B. for lubrication purposes.
b) Eine thixotrope Grundmasse für Lacke und Farben kann wie folgt erhalten werden: 10 g oc-n-Dodecyla-propyl-/?-amino-propionsäure werden in 1000 g Petroläther erwärmt. Man erhält eine gallertartige, zähflüssige Masse, in der geeignete Lackrohstoffe und Farben eingearbeitet werden können. Diese Lacke und ίο Farben fließen aus Behältern, wie z. B. Tuben, nicht aus, haften am Pinsel, lassen sich aber leicht verstreichen. b) A thixotropic base material for lacquers and paints can be obtained as follows: 10 g oc-n-dodecyla-propyl - /? - amino-propionic acid are heated in 1000 g of petroleum ether. A gelatinous, viscous mass is obtained in which suitable paint raw materials and Colors can be incorporated. These varnishes and paints flow from containers such as B. tubes, not from, stick to the brush, but can be easily spread.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1507162A CH415667A (en) | 1962-12-21 | 1962-12-21 | Process for the preparation of aminocarboxylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1493814A1 DE1493814A1 (en) | 1969-05-22 |
| DE1493814B2 true DE1493814B2 (en) | 1973-03-15 |
| DE1493814C3 DE1493814C3 (en) | 1973-10-04 |
Family
ID=4406109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1493814A Expired DE1493814C3 (en) | 1962-12-21 | 1963-11-28 | Use of aminocarboxylic acids as viscosity-increasing agents |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3328436A (en) |
| BE (1) | BE641517A (en) |
| BR (1) | BR6355060D0 (en) |
| CH (1) | CH415667A (en) |
| DE (1) | DE1493814C3 (en) |
| DK (1) | DK123092B (en) |
| ES (1) | ES294734A1 (en) |
| GB (1) | GB992737A (en) |
| NL (2) | NL302183A (en) |
| SE (1) | SE318860B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740421A (en) * | 1966-09-19 | 1973-06-19 | Basf Wyandotte Corp | Polyoxyethylene-polyoxypropylene aqueous gels |
| US3846458A (en) * | 1971-01-07 | 1974-11-05 | Us Agriculture | Arthropod maturation inhibitors |
| US4889646A (en) * | 1987-06-30 | 1989-12-26 | Amoco Corporation | Nitrogen containing dispersants treated with mineral acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB601123A (en) * | 1945-03-16 | 1948-04-28 | James Lincoln | Improvements in the production of synthetic linear condensation polymers |
| GB792486A (en) * | 1954-12-23 | 1958-03-26 | Henkel & Cie Gmbh | A process for the production of ª‡-nitrilocarboxylic acid esters |
-
0
- NL NL137819D patent/NL137819C/xx active
- NL NL302183D patent/NL302183A/xx unknown
-
1962
- 1962-12-21 CH CH1507162A patent/CH415667A/en unknown
-
1963
- 1963-11-28 DE DE1493814A patent/DE1493814C3/en not_active Expired
- 1963-12-03 BR BR155060/63A patent/BR6355060D0/en unknown
- 1963-12-06 US US328483A patent/US3328436A/en not_active Expired - Lifetime
- 1963-12-13 GB GB49235/63A patent/GB992737A/en not_active Expired
- 1963-12-19 BE BE641517A patent/BE641517A/xx unknown
- 1963-12-19 DK DK592863AA patent/DK123092B/en unknown
- 1963-12-19 SE SE14203/63A patent/SE318860B/xx unknown
- 1963-12-20 ES ES294734A patent/ES294734A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6355060D0 (en) | 1973-07-19 |
| NL302183A (en) | |
| GB992737A (en) | 1965-05-19 |
| US3328436A (en) | 1967-06-27 |
| CH415667A (en) | 1966-06-30 |
| BE641517A (en) | 1964-06-19 |
| ES294734A1 (en) | 1964-06-01 |
| DE1493814C3 (en) | 1973-10-04 |
| NL137819C (en) | |
| DK123092B (en) | 1972-05-15 |
| SE318860B (en) | 1969-12-22 |
| DE1493814A1 (en) | 1969-05-22 |
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| Date | Code | Title | Description |
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| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |