DE19529767A1 - Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives - Google Patents
Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivativesInfo
- Publication number
- DE19529767A1 DE19529767A1 DE19529767A DE19529767A DE19529767A1 DE 19529767 A1 DE19529767 A1 DE 19529767A1 DE 19529767 A DE19529767 A DE 19529767A DE 19529767 A DE19529767 A DE 19529767A DE 19529767 A1 DE19529767 A1 DE 19529767A1
- Authority
- DE
- Germany
- Prior art keywords
- amphiphilic compounds
- compounds according
- amphiphilic
- hydrophobic groups
- acid derivatives
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 125000001165 hydrophobic group Chemical group 0.000 title abstract description 7
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000004140 cleaning Methods 0.000 claims abstract description 3
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 3
- 238000000605 extraction Methods 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- -1 demulsifiers Substances 0.000 abstract description 43
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 abstract description 2
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 230000003165 hydrotropic effect Effects 0.000 abstract description 2
- 238000005555 metalworking Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000271915 Hydrophis Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000004442 acylamino group Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229960003872 benzethonium Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000003549 soybean oil Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/28—Aminocarboxylic acids
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
Abstract
Description
Die Erfindung betrifft amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von Aminobernsteinsäurederivaten.The invention relates to amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives.
Als amphiphile Substanzen sind eine große Vielfalt an anionischen, katio nischen, nichtionischen und zwitterionischen Verbindungen bekannt. Die weitaus meisten dieser Substanzen bestehen aus einer hydrophilen Kopf gruppe und wenigstens einem hydrophoben Teil.A wide variety of anionic, katio are as amphiphilic substances African, nonionic and zwitterionic compounds known. The By far most of these substances consist of a hydrophilic head group and at least one hydrophobic part.
Bei den amphiphilen Substanzen gibt es aus ökologischen Gründen, z. B. bezüglich der Verringerung des Verpackungs- und Transportaufwandes, die Notwendigkeit, immer größere Wirkung pro Masse an eingesetzter Substanz zu erzielen. Da eine Optimierung durch Mischung von amphiphilen Substan zen nur begrenzt weiterführt, sind neue amphiphile Substanzen mit einem höheren Wirkungsgrad erforderlich. Es müssen daher insbesondere Stoffe mit niedrigeren kritischen Micellbildungskonzentrationen und/oder niedrigeren Ober- und Grenzflächenspannungen gefunden werden, um die Ein satzmengen an Wirksubstanz deutlich reduzieren zu können. Zudem müssen sie leicht, am besten aus leicht zugänglichen Ausgangssubstanzen, erhält lich sein.In the case of amphiphilic substances, there are ecological reasons, e.g. B. with regard to the reduction of packaging and transport costs, the Necessity, ever greater effect per mass of substance used to achieve. Since an optimization by mixing amphiphilic substance zen continues to be limited, are new amphiphilic substances with one higher efficiency required. In particular, therefore, there must be substances with lower critical micelle formation concentrations and / or lower surface and interfacial tensions can be found around the A to be able to significantly reduce the amount of active substance. Also have to it easily, preferably from easily accessible starting substances be.
Erste Lösungsansätze in Richtung auf leistungsfähigere amphiphile Sub stanzen durch Verdoppelung eines Teils der Struktur (hydrophile Kopfgrup pe, hydrophobe Gruppe) sind bereits bekannt. So können kationische grenzflächenaktive Verbindungen durch die Addition von langkettigen Al kylhalogeniden an permethylierte Alkylendiamine erhalten werden [R. Zana, M. Benrraou, R. Rueff, Langmuir, Z (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].First approaches towards more powerful amphiphilic sub punch by doubling part of the structure (hydrophilic head group pe, hydrophobic group) are already known. So cationic surface-active compounds through the addition of long-chain Al alkyl halides on permethylated alkylenediamines can be obtained [R. Zana, Benrraou, M., Rueff, R., Langmuir, Z (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
Anionische grenzflächenaktive Verbindungen mit wenigstens zwei hydrophi len und wenigstens zwei hydrophoben Gruppen sind bisher auf der Basis von Diglycidylethern hergestellt worden (US 5 160 450, JP 01 304 033, JP 4 124 165). Diglycidylether gelten jedoch als toxikologisch bedenklich und sind recht teuer. Darüber hinaus wird für ihre Herstellung Epichlor hydrin verwendet, was zu großen Mengen an Reststoffen führt, so daß diese Verbindungen unter ökotoxikologischen wie auch ökonomischen Gesichtspunk ten nicht mehr zeitgemäß sind.Anionic surfactant compounds with at least two hydrophi len and at least two hydrophobic groups have so far been based on Diglycidyl ethers have been prepared (US 5 160 450, JP 01 304 033, JP 4 124 165). However, diglycidyl ethers are considered toxicologically unsafe and are quite expensive. In addition, Epichlor is used for their manufacture hydrin used, which leads to large amounts of residues, so this Connections from an ecotoxicological as well as an economic point of view are out of date.
Es bestand daher die Aufgabe, amphiphile Verbindungen aufzufinden, die wenigstens zwei hydrophile und wenigstens zwei hydrophobe Gruppen aufwei sen, gute Tensideigenschaften sowie einen hohen Wirkungsgrad zeigen, und aus technisch leicht verfügbaren Rohstoffen ohne großen Anfall von uner wünschten Nebenprodukten hergestellt werden können.The task was therefore to find amphiphilic compounds that have at least two hydrophilic and at least two hydrophobic groups sen, good surfactant properties and high efficiency, and from technically readily available raw materials without a large desired by-products can be produced.
Die Aufgabe wird erfindungsgemäß durch amphiphile N,N′-Dialkyl-N,N′-di bernsteinsäurediester, die durch die Addition von N,N′-Dialkyldiaminen an zwei Äquivalente Maleinsäure und anschließende Veresterung mit Alkoholen oder Alkoholethoxylaten hergestellt werden können, gelöst.The object is achieved by amphiphilic N, N'-dialkyl-N, N'-di succinic acid diester by the addition of N, N'-dialkyldiamines two equivalents of maleic acid and subsequent esterification with alcohols or alcohol ethoxylates can be prepared.
Bei den erfindungsgemäßen Verbindungen handelt es sich also um Verbindun gen der allgemeinen Formel (I)The connections according to the invention are therefore connections gene of the general formula (I)
wobei R, R¹, R², R³, R⁴, M und M¹ in der Formel (I) die im folgenden be
schriebenen Bedeutungen haben:
R und R⁴ stehen unabhängig voneinander für einen unverzweigten oder ver
zweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 1 bis
22, vorzugsweise 6 bis 18, Kohlenstoffatomen. Es seien als Substituenten
R und R⁴ im einzelnen die Reste Methyl, Ethyl, n-Propyl, n-Butyl, n-Pen
tyl, n-Hexyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl, n-Dodecyl,
n-Tridecyl, n-Tetradecyl, n-Pentadecyl, n-Hexadecyl, n-Heptadecyl n-Oc
tadecyl, n-Nonadecyl, n-Eicosyl, n-Uneicosyl, n-Docosyl und ihre ver
zweigtkettigen Isomeren sowie die entsprechenden einfach, zweifach oder
dreifach ungesättigten Reste genannt.where R, R¹, R², R³, R⁴, M and M¹ in formula (I) have the meanings described below:
R and R⁴ independently of one another represent an unbranched or ver branched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 6 to 18, carbon atoms. They are as substituents
R and R⁴ in particular the residues methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n- Dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl n-oc tadecyl, n-nonadecyl, n-eicosyl, n-uneicosyl, n-docosyl and their branched chain isomers and the corresponding simple , called double or triple unsaturated residues.
R² bedeutet einen aliphatischen oder aromatischen, cyclischen oder acy clischen Spacer mit 2 bis 16, vorzugsweise 2 bis 12 Kohlenstoffatomen und 0 bis 6 Sauerstoff- und/oder Stickstoffatomen, der darüber hinaus noch verzweigt sein kann. M und M¹ bedeuten Alkali-, Ammonium, Alkanolammonium oder 1/2 Erdalkali.R² means an aliphatic or aromatic, cyclic or acy clische spacer with 2 to 16, preferably 2 to 12 carbon atoms and 0 to 6 oxygen and / or nitrogen atoms, or more can be branched. M and M¹ mean alkali, ammonium, alkanolammonium or 1/2 alkaline earth.
R¹ und R³ stehen unabhängig voneinander für einen unverzweigten oder ver zweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 1 bis 18, vorzugsweise 1 bis 6, Kohlenstoffatomen. Es seien als Substituenten R¹ und R³ im einzelnen die Reste Methyl, Ethyl, n-Propyl, n-Butyl, n-Pen tyl, n-Hexyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl, n-Dodecyl, n-Tridecyl, n-Tetradecyl, n-Pentadecyl, n-Hexadecyl, n-Heptadecyl, n-Oc tadecyl, und ihre verzweigtkettigen Isomeren sowie die entsprechenden einfach, zweifach oder dreifach ungesättigten Reste genannt.R¹ and R³ independently represent an unbranched or ver branched, saturated or unsaturated hydrocarbon radical with 1 to 18, preferably 1 to 6, carbon atoms. They are as substituents R¹ and R³ in particular the residues methyl, ethyl, n-propyl, n-butyl, n-pen tyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-oc tadecyl, and their branched chain isomers and the corresponding called single, double or triple unsaturated residues.
Die erfindungsgemäßen amphiphilen Verbindungen zeichnen sich meist durch extrem niedrige kritische Micellbildungskonzentrationen (CMC) und sehr niedrige Oberflächen- und Grenzflächenspannungen (z. B. gegen Paraffin) aus, was auf ihre besondere Struktur - wenigstens zwei hydrophile Gruppen und wenigstens zwei hydrophobe Gruppen - zurückgeführt werden muß. Dar über hinaus weisen die meisten von ihnen ein recht hohes hydrophiles Sus pendiervermögen auf, das etwa auf halbem Wege zwischen dem konventionel ler Tenside und dem des Pentanatriumtripolyphosphats liegt. Einige dieser Verbindungen sind extrem schnelle Netzmittel.The amphiphilic compounds according to the invention are usually characterized by extremely low critical micelle levels (CMC) and very low surface and interfacial tensions (e.g. against paraffin) from what is due to their special structure - at least two hydrophilic groups and at least two hydrophobic groups - must be recycled. Dar moreover, most of them have a rather high hydrophilic sus pendulum ability, about halfway between the conventional ler surfactants and that of pentasodium tripolyphosphate. Some of these Connections are extremely fast wetting agents.
Die amphiphilen Verbindungen gemäß dieser Erfindung eignen sich insbeson dere als Emulgatoren, Demulgatoren, Detergenzien, Dispergatoren und Hy drotropica sowie Antistatika in Industrie und Haushalt, beispielsweise auf den Gebieten Metallbearbeitung, Erzgewinnung, Oberflächenveredelung, Kunststoffherstellung, Textilhilfsmittel, Waschen und Reinigen, insbeson dere von Textilien oder von harten Oberflächen, Kosmetik, Medizin und Nahrungsmittelverarbeitung und -zubereitung.The amphiphilic compounds according to this invention are particularly suitable others as emulsifiers, demulsifiers, detergents, dispersants and hy drotropica and antistatic agents in industry and household, for example in the fields of metalworking, ore extraction, surface finishing, Plastic production, textile auxiliaries, washing and cleaning, in particular of textiles or hard surfaces, cosmetics, medicine and Food processing and preparation.
Hierbei können sie mit allen gängigen anionischen, nichtionischen, katio nischen und ampholytischen grenzflächenaktiven Substanzen kombiniert wer den. Als Beispiele für nichtionische grenzflächenaktive Substanzen, die für eine Kombination eingesetzt werden können, seien Fettsäureglyceride, Fettsäurepolyglyceride, Fettsäureester, Ethoxylate höherer Alkohole, Po lyoxyethylenfettsäureglyceride, Polyoxyethylenpropylenglykolfettsäure ester, Polyoxyethylensorbitanfettsäureester, Polyoxyethylen-Rhizinusöl- oder gehärtete Rhizinusöl-Derivate, Polyoxyethylenlanolinderivate, Poly oxyethylenfettsäureamide, Polyoxyethylenalkylamine, Alkanolamine, Alkyl aminoxide, Derivate von Eiweißhydrolysaten, Hydroxymischether, Alkylpoly glycoside und Alkylglucamide genannt. Als Beispiele für anionische grenz flächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien Seifen, Ethercarbonsäuren und deren Salze, Alkylsulfonate, α-Ole finsulfonate, α-Sulfofettsäurederivate, Sulfonate höherer Fettsäureester, höhere Alkoholsulfate, Alkoholethersulfate, Hydroxymischethersulfate, Salze von Phosphatestern, Tauride, Isethionate, lineare Alkylbenzolsul fonate, Cumolsulfonat, Alkylarylsulfonate, Sulfate der Polyoxyethylen fettsäureamide und Salze von Acylaminosäuren genannt.You can use all common anionic, nonionic, katio niche and ampholytic surfactants combined the. As examples of nonionic surfactants, the can be used for a combination are fatty acid glycerides, Fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, Po lyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene castor oil or hardened castor oil derivatives, polyoxyethylene lanolin derivatives, poly oxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkanol amines, alkyl amine oxides, derivatives of protein hydrolyzates, hydroxy mixed ethers, alkyl poly called glycosides and alkyl glucamides. As examples of anionic borders surface-active substances that can be used for combinations, be soaps, ether carboxylic acids and their salts, alkyl sulfonates, α-oils finsulfonates, α-sulfofatty acid derivatives, sulfonates of higher fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hydroxy mixed ether sulfates, Salts of phosphate esters, taurides, isethionates, linear alkylbenzenesul fonates, cumene sulfonate, alkylarylsulfonates, sulfates of polyoxyethylene called fatty acid amides and salts of acylamino acids.
Als Beispiele für kationische gängige grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien Alkyltrimethylammonium salze, Dialkyldimethylammoniumsalze, Alkyldimethylbenzylammoniumsalze, Alkylpyridiniumsalze, Alkylisochinoliniumsalze, Benzethoniumchloride und kationische Acylaminosäurederivate genannt.As examples of common cationic surfactants that combinations that can be used are alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, Alkylpyridinium salts, alkylisoquinolinium salts, benzethonium chlorides and called cationic acylamino acid derivatives.
Als Beispiele für ampholytische grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien Aminosäuren, Betaine, Sul fobetaine, Imidazolinderivate, Sojaöllipide und Lecithin genannt.As examples of ampholytic surfactants used for Combinations can be used, be amino acids, betaines, sul called fobetaine, imidazoline derivatives, soybean oil lipids and lecithin.
Darüber hinaus können die erfindungsgemäßen amphiphilen Verbindungen auch für sich miteinander kombiniert werden. In addition, the amphiphilic compounds according to the invention can also can be combined with each other.
Den erfindungsgemäßen amphiphilen Verbindungen können ebenfalls gängige Additive zugesetzt werden. Solche Additive werden speziell für eine For mulierung ausgewählt und umfassen üblicherweise anorganische Salze, wie Natriumchlorid und -sulfat, sowie Builder, Hydrotropica, UV-Absorber, Weichmacher, Chelatbildner, Viskositätsmodifizierer und Riechstoffe.The amphiphilic compounds according to the invention can also be common Additives are added. Such additives are specifically for a For mulation selected and usually include inorganic salts such as Sodium chloride and sulfate, as well as builders, hydrotropics, UV absorbers, Plasticizers, chelating agents, viscosity modifiers and fragrances.
Die obengenannten Verbindungen lassen sich aus N,N′-dialkylierten Diami nen und zwei Äquivalenten Maleinsäure bei Temperaturen von 80 bis 180°C herstellen. Nach der erfolgten zweifachen Addition an das Diamin erfolgt die Veresterung mit zwei Äquivalenten Alkohol oder Alkoholalkoxylat, hiermit läßt sich die Hydrophilie der Produkte genau abstimmen, in Gegen wart eines Katalysators, vorzugsweise eines basischen Katalysators, bei Temperaturen von 60 bis 190°C. Die Neutralisation erfolgt mit wäßrigen Alkali- oder Erdalkalihydroxiden oder wäßrigem Ammoniak oder Alkanolami nen.The above compounds can be made from N, N'-dialkylated diami NEN and two equivalents of maleic acid at temperatures from 80 to 180 ° C produce. After the double addition to the diamine is carried out esterification with two equivalents of alcohol or alcohol alkoxylate, this allows the hydrophilicity of the products to be fine-tuned, in counter were a catalyst, preferably a basic catalyst Temperatures from 60 to 190 ° C. The neutralization is carried out with aqueous Alkali or alkaline earth metal hydroxides or aqueous ammonia or alkanolami nen.
Claims (6)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19529767A DE19529767A1 (en) | 1995-08-12 | 1995-08-12 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives |
| AU66998/96A AU6699896A (en) | 1995-08-12 | 1996-07-16 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives |
| PCT/EP1996/003114 WO1997007089A1 (en) | 1995-08-12 | 1996-07-16 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19529767A DE19529767A1 (en) | 1995-08-12 | 1995-08-12 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives |
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| Publication Number | Publication Date |
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| DE19529767A1 true DE19529767A1 (en) | 1997-02-13 |
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|---|---|---|---|
| DE19529767A Withdrawn DE19529767A1 (en) | 1995-08-12 | 1995-08-12 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives |
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| Country | Link |
|---|---|
| AU (1) | AU6699896A (en) |
| DE (1) | DE19529767A1 (en) |
| WO (1) | WO1997007089A1 (en) |
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| WO2001030355A1 (en) | 1999-10-25 | 2001-05-03 | Laboratoire Theramex | Contraceptive medicine based on a progestational agent and an oestrogen and preparation method |
| US6593273B2 (en) | 2000-10-06 | 2003-07-15 | Monsanto Technology Llc | Method for reducing pest damage to corn by treating transgenic corn seeds with pesticide |
| US6586365B2 (en) | 2000-10-06 | 2003-07-01 | Monsanto Technology, Llc | Method for reducing pest damage to corn by treating transgenic corn seeds with clothianidin pesticide |
| CN106732168A (en) * | 2016-12-15 | 2017-05-31 | 钦州市钦南区科学技术情报研究所 | A kind of surface activator composition and preparation method thereof |
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| US3077487A (en) * | 1959-06-17 | 1963-02-12 | Victor Chemical Works | Lower alkylene and lower alkylenephenylene-lower alkylene polyamine bis n, n'-lower alkylene di and tri carboxylic acids, esters, salts, and chelates |
| CH575909A5 (en) * | 1972-08-21 | 1976-05-31 | Ciba Geigy Ag | |
| US5332505A (en) * | 1992-10-02 | 1994-07-26 | Betz Laboratories, Inc. | Method for inhibiting silica and silicate deposition |
-
1995
- 1995-08-12 DE DE19529767A patent/DE19529767A1/en not_active Withdrawn
-
1996
- 1996-07-16 AU AU66998/96A patent/AU6699896A/en not_active Abandoned
- 1996-07-16 WO PCT/EP1996/003114 patent/WO1997007089A1/en active Application Filing
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| AU6699896A (en) | 1997-03-12 |
| WO1997007089A1 (en) | 1997-02-27 |
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