EP0847385A1 - Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene - Google Patents
Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetyleneInfo
- Publication number
- EP0847385A1 EP0847385A1 EP96923979A EP96923979A EP0847385A1 EP 0847385 A1 EP0847385 A1 EP 0847385A1 EP 96923979 A EP96923979 A EP 96923979A EP 96923979 A EP96923979 A EP 96923979A EP 0847385 A1 EP0847385 A1 EP 0847385A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- amphiphilic compounds
- compounds according
- acetylene
- acid
- hydrophobic groups
- 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- Withdrawn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 21
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 125000000129 anionic group Chemical group 0.000 title abstract description 8
- 125000001165 hydrophobic group Chemical group 0.000 title abstract description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title abstract description 3
- 238000004140 cleaning Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000005555 metalworking Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- -1 anionic acetylene derivatives Chemical class 0.000 description 44
- 239000002253 acid Substances 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- ZUQAPLKKNAQJAU-UHFFFAOYSA-N acetylenediol Chemical class OC#CO ZUQAPLKKNAQJAU-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000003165 hydrotropic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 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 class CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides 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
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 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
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960003872 benzethonium Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229960003080 taurine Drugs 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
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- 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
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
- C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
Definitions
- the invention relates to anionic amphiphilic compounds with several hydrophilic and hydrophobic groups based on acetylene derivatives.
- amphiphilic substances A wide variety of anionic, cationic, nonionic and zwitterionic compounds are known as amphiphilic substances. The vast majority of these substances consist of a hydrophilic head group and at least one hydrophobic part.
- amphiphilic substances there are ecological reasons, e.g. B. with regard to the reduction of packaging and transport costs, the need to achieve ever greater effect per mass of substance used. Because an optimization by mixing amphiphilic substances requires higher efficiency. In particular, substances with lower critical micelle formation concentrations and / or lower surface and interfacial tensions have to be found in order to be able to significantly reduce the amount of active substance used. In addition, they must be readily available, preferably from easily accessible starting substances.
- cationic surface-active compounds can be obtained by adding long-chain alkyl halides to permethylated alkylenediamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
- Anionic surface-active compounds with at least two hydrophilic and at least two hydrophobic groups have hitherto been produced on the basis of diglycidyl ethers (US Pat. No. 5,160,450, JP 01,304,033, JP 4,124,165).
- diglycidyl ethers are considered toxicologically unsafe and are quite expensive.
- epichlorohydrin is used for their production, which leads to large amounts of residues, so that these compounds are no longer up-to-date from an ecotoxicological and economic point of view.
- amphiphilic anionic compounds which have at least two hydrophilic and at least two hydrophobic groups, are readily water-soluble and have good surfactant properties and high efficiency, and are prepared from readily available technical raw materials without a large amount of undesired by-products can.
- anionic acetylene derivatives which can be prepared by functionalizing acetylene diols.
- the acetylenediols are either prepared by known processes by reacting acetylene with alkali metal hydroxides and then with methyl ketones either in an aqueous or non-aqueous medium (e.g. BSI Shergina et al., Izx, Akad. Nauk SSSR, Ser. Khim., 1977 , (6), 1447 (CA: 8_7_: - 101877); DE 37 11 282, JP 52046009.) or with aldehydes or obtained by coupling two terminal alkynols (e.g. DE 2520735, JP 50108204).
- aqueous or non-aqueous medium e.g. BSI Shergina et al., Izx, Akad. Nauk SSSR, Ser. Khim., 1977 , (6), 1447 (CA: 8_7_:
- Functionalization is the reaction of the alkynyl diols with SO / inert gas (or oleum or chlorosulfonic acid or amidosulfonic acid) and subsequent neutralization with a base (not when using amidosulfonic acid) or with polyphosphoric acid and subsequent neutralization, or with one Halogenacetic acid, a sulton and subsequent neutralization or with a taurine and subsequent neutralization.
- SO / inert gas or oleum or chlorosulfonic acid or amidosulfonic acid
- a base not when using amidosulfonic acid
- polyphosphoric acid and subsequent neutralization or with one Halogenacetic acid, a sulton and subsequent neutralization or with a taurine and subsequent neutralization.
- the compounds according to the invention are all compounds of the general formula (I):
- R to R in the formula (I) have the meanings described below:
- R to R. independently of one another represent hydrogen, an unbranched or branched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 6 to 18, carbon atoms, it being possible for only R or R “and R— or R to stand for hydrogen at the same time.
- r can assume the values 1 to 4, preferably 1 or 2, X and Y independently of one another represent the substituents
- n 0 to 20, preferably 0 to 8
- m 0 to 20, preferably 0 to 12
- n + m 0 to 40, preferably 0 to 20,
- alkoxylate units if present, can be included randomly or in blocks and the order is arbitrary and where M is an alkali, ammonium or alkanolammonium ion or stoichiometrically an alkaline earth metal ion.
- amphiphilic compounds according to the invention are usually characterized by extremely low critical micelle formation concentrations (CMC) and very low surface and interfacial tensions (e.g. against paraffin), which can be attributed to their special structure - at least two hydrophilic groups and at least two hydrophobic groups got to.
- CMC critical micelle formation concentrations
- hydrophilic suspending capacity is about halfway between the conventional ones Surfactants and that of the pentasodium tripolyphosphate is.
- amphiphilic compounds according to this invention are particularly suitable as emulsifiers, demulsifiers, detergents, dispersants and hydro tropics and antistatic agents in industry and in the household, for example in the fields of metalworking, ore extraction, textile auxiliaries, surface finishing, washing and cleaning, cosmetics, Medicine and food processing and preparation.
- nonionic surface-active substances which can be used for a combination are fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, polyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene-ricinoleic acid ethylenediethoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenedioleoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediamine ethylenedioleoxyethoxyethenoethoxyethylene acid ethylenediethoxyethylene acid ethylenedioleoxyethoxyethoxy acid ethylenedioleoxye
- anionic surface-active substances which can be used for combinations include soaps, ether carboxylic acids and their salts, alkyl sulfonates, ⁇ -olefin sulfonates, ⁇ -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 alkylbenzenesulfonates, cumene sulfonates, alkylarylsulfonates, sulfates of polyoxyethylene fatty acid amides and salts of acylamino acids.
- cationic common surface-active substances which can be used for combinations include alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, alkylpyridinium salts, alkylisoquinolinium salts, benzethonium chlorides and cationic acylamino acid derivatives.
- ampholytic surface-active substances examples include amino acids, betaines, sulfobetaines, imidazoline derivatives, soybean oil lipids and lecithin.
- amphiphilic compounds according to the invention can also be combined with one another.
- additives can also be added to the amphiphilic compounds according to the invention.
- Such additives are specially selected for a formulation 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.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
L'invention concerne des composés amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes à base de dérivés d'acétylène.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19532293 | 1995-09-01 | ||
| DE19532293A DE19532293A1 (de) | 1995-09-01 | 1995-09-01 | Anionische amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von Acetylenderivaten |
| PCT/EP1996/002994 WO1997009304A1 (fr) | 1995-09-01 | 1996-07-09 | Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0847385A1 true EP0847385A1 (fr) | 1998-06-17 |
Family
ID=7771015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96923979A Withdrawn EP0847385A1 (fr) | 1995-09-01 | 1996-07-09 | Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0847385A1 (fr) |
| JP (1) | JPH11513032A (fr) |
| AU (1) | AU6418996A (fr) |
| DE (1) | DE19532293A1 (fr) |
| WO (1) | WO1997009304A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19717264A1 (de) | 1997-04-24 | 1998-10-29 | Huels Chemische Werke Ag | Amphiphole Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Di, Oligo- oder Polyenen |
| US7230068B2 (en) * | 2003-10-09 | 2007-06-12 | Ambrx, Inc. | Polymer derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3831822A1 (de) * | 1988-09-19 | 1990-04-05 | Henkel Kgaa | Verfahren zur herstellung von sulfonaten gegebenenfalls ethoxylierter und/oder propoxylierter fettalkohole |
| DE3932492A1 (de) * | 1989-09-28 | 1991-05-02 | Henkel Kgaa | Salze von sulfonierten estern von dicarbonsaeuren mit ungesaettigten fettalkoholen bzw. -alkoxylaten, verfahren zu ihrer herstellung und ihre verwendung als oberflaechenaktive mittel |
| DE4316214A1 (de) * | 1993-05-14 | 1994-11-17 | Henkel Kgaa | Sulfonierte Diester |
| DE4441363A1 (de) * | 1994-11-21 | 1996-05-23 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf Basis von Di-, Oligo- oder Polyolethern |
| DE4445133A1 (de) * | 1994-12-17 | 1996-06-20 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Estern |
-
1995
- 1995-09-01 DE DE19532293A patent/DE19532293A1/de not_active Withdrawn
-
1996
- 1996-07-09 EP EP96923979A patent/EP0847385A1/fr not_active Withdrawn
- 1996-07-09 AU AU64189/96A patent/AU6418996A/en not_active Abandoned
- 1996-07-09 WO PCT/EP1996/002994 patent/WO1997009304A1/fr not_active Application Discontinuation
- 1996-07-09 JP JP9510797A patent/JPH11513032A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9709304A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11513032A (ja) | 1999-11-09 |
| AU6418996A (en) | 1997-03-27 |
| WO1997009304A1 (fr) | 1997-03-13 |
| DE19532293A1 (de) | 1997-03-06 |
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