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WO2018065070A1 - Aminosiloxanes secondaires et son procédé de production - Google Patents

Aminosiloxanes secondaires et son procédé de production Download PDF

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Publication number
WO2018065070A1
WO2018065070A1 PCT/EP2016/074062 EP2016074062W WO2018065070A1 WO 2018065070 A1 WO2018065070 A1 WO 2018065070A1 EP 2016074062 W EP2016074062 W EP 2016074062W WO 2018065070 A1 WO2018065070 A1 WO 2018065070A1
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WO
WIPO (PCT)
Prior art keywords
general formula
radical
number equal
aminosiloxanes
atoms
Prior art date
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Ceased
Application number
PCT/EP2016/074062
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German (de)
English (en)
Inventor
Alfred Popp
Oliver SCHÄFER
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Wacker Chemie AG
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Wacker Chemie AG
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Publication date
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Priority to PCT/EP2016/074062 priority Critical patent/WO2018065070A1/fr
Publication of WO2018065070A1 publication Critical patent/WO2018065070A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the invention relates to aminosiloxanes, a process for their preparation and use for textile finishing, for cosmetic formulations, the treatment of surfaces, for the preparation of block copolymers or for the binding and removal of carbon dioxide from exhaust gases.
  • aminosiloxanes are among the most important organically functionalized organopolysiloxanes and are used successfully in many different fields of application. These include textile equipment (eg US
  • WO 2009/019161 describes a process for the production of primary and secondary aminoorganyl-triorganylsilanes of the general formula R '3-n R 1 n Si-R 2 -NR 3 R 4 by reacting cyclic or acyclic amines of the general formula H-NR 3 R 4 with (haloorganyl) silanes of the general formula R 3 '_ n R 1 n Si-R 2 -X, where first the (haloorganyl) silane and the amine are reacted, and then releases the amine by addition of a base from the salt formed is, wherein the salt of the base formed at temperature ⁇ 200 ° C is liquid and can be separated.
  • Haloalkylsiloxanes in which the alkyl group between Si and N ⁇ 3 contain methylene units are generally prepared by transition metal-catalyzed reaction of an Si-H group with allyl halides (hydrosilylation) and subsequent nucleophilic substitution of the halide by the desired amine.
  • transition metal catalysts mostly Pt,
  • Allyl halides are harmful substances.
  • allyl chloride is suspected to cause genetic defects or to cause cancer.
  • the invention relates to aminosiloxanes (A) of the general formula 1 in which
  • R 1 , R 4 are independently a substituted or
  • Heteroatom selected from the group consisting of N, O, S, and P may be replaced,
  • R 2 , R 3 are independently a substituted or
  • n is a number equal to 1 or 2 and
  • n is an integer equal to or greater than 0
  • Aminosiloxanes (A) are inexpensive and safe in good
  • Yields can be produced. They are suitable, for example, for textile finishing, for cosmetic formulations, for the treatment of surfaces, for the production of block copolymers and in particular for the binding and removal of carbon dioxide from exhaust gases.
  • the hydrocarbon radicals R 1 , R 4 may be alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.
  • -Pentyl radical Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-octadecyl radical; Cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; Alkenyl radicals, such as the vinyl, 1-propenyl and the 2-propenyl radical; Aryl radicals, such as the pheny
  • a is a number equal to 1, 2, 3, 4, 5 or 6,
  • b is a number equal to 1, 2 or 3,
  • c is a number equal to 1, 2, 3, 4 or 5
  • d is a number equal to 0 or 1
  • e is a number equal to 1, 2, 3, 4, 5 or 6,
  • f is a number equal to 1, 2 or 3,
  • g is a number equal to 1, 2, 3 or 4,
  • h is a number equal to 0 or 1
  • R 6 is a hydrocarbon radical having 1-6 C atoms, in particular ethyl or methyl and
  • R 7 is a hydrocarbon radical having 1-6 C atoms, in particular ethyl or methyl.
  • radicals R 1 , R 4 are independently of each other preferably selected from alkoxyalkyl radicals or alkylaminoalkyl radicals.
  • the radicals R 1 , R 4 independently of one another are an alkoxyalkyl radical, in particular Cl-3-alkoxyCl-3-alkyl radical.
  • the hydrocarbon radicals R 2 , R 3 may be alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.
  • -Pentyl radical Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl residual and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-octadecyl radical; Cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; Alkenyl radicals, such as the vinyl, 1-propenyl and the 2-propenyl radical; Aryl radicals, such as the pheny
  • R 2 , R 3 is the methyl, ethyl, iso and n-propyl, iso and n-butyl, phenyl or vinyl radical.
  • R 2 , R 3 is particularly preferably the methyl or ethyl radical.
  • n preferably has the value 1.
  • m preferably has the value 0 or 1.
  • Another object of the invention is a method for
  • Condensation in the presence of further reactive compounds of the general formula 7 can take place to a product of the general formula (1), or by b) hydrolytic condensation of (haloorganyl) silicium compounds of the general formula (5), wherein the hydrolytic condensation can take place in the presence of further reactive compounds of the general formula 7 to a product the general formula (8) and reaction with amines of the general formula (4),
  • R ' is an acyloxy radical and an alkoxy radical having in each case 1-10 C atoms
  • R '' is a radical of general formula 10
  • X, Y are independently chlorine, bromine or iodine and
  • p is an integer equal to or greater than 3
  • R 1 , R 2 , R 3 , R 4 , n and m have the abovementioned meanings.
  • the amine of general formula (4) is preferably in excess, i. H. in molar ratios based on the proportion of the reactive groups X and Y from 1.1 to 1 to 100 to 1, preferably from 1.5 to 1 to 50 to 1, particularly preferably from 2 to 1 to 20 to 1, in particular from 3 used to 1 to 10 to 1.
  • the base (B) is preferably in molar ratios based on the proportion of the reactive groups X and Y of 0.5 to 1 to 10 to 1, preferably from 0.7 to 1 to 5 to 1, more preferably from 0.8 to 1 to 2 to 1, in particular from 0.9 to 1 to 1.0 to 1 used.
  • step al) and a2) can take place successively or simultaneously. It is also possible to carry out a time-delayed procedure in which the start of step a2), ie the addition of the base (B), is begun after the start but before the end of step al). If a base (B) which has free NH or NH 2 groups is used in the processes according to the invention, step a2), ie the addition of the oligoamine, is preferably carried out after the reaction in step al). Preference is given to using bases (B) which, in process step a2), form salts which, even at temperatures ⁇ 150.degree. C., form particularly preferably ⁇ 100.degree. C. or ⁇ 90.degree. C. liquids. Step al) of the method according to the invention is preferably carried out at temperatures of 50 to 250 ° C. To one
  • temperatures of 50 to 220 ° C, in particular from 80 ° C to 150 ° C have proven to be particularly advantageous.
  • the steps a2) and a3) of the processes according to the invention are carried out at a temperature at which the halide of the base (B) is present as a separate liquid phase, preferably at temperatures of 0-250 ° C., preferably at temperatures of 20 to 150 ° C. and especially preferably carried out at temperatures of 50 to 100 ° C.
  • the pressure in the reaction steps al), a2) and a3) is preferably 0.05 to 2 MPa (abs.), More preferably 0.08 to 1.5 MPa (abs.), In particular 0.09 to 1 MPa (abs .).
  • All reaction steps are preferably carried out under protective gas, e.g. Nitrogen and argon carried out.
  • protective gas e.g. Nitrogen and argon carried out.
  • the processes according to the invention can also have one or more of the following additional process steps:
  • step al) if the amine of the general formula (4) in step al) was used in excess, this excess can be completely or partially separated before the addition of the base (B) in step a2).
  • the separation is preferably carried out by distillation. This measure is preferably used to reduce the solubility of the respective salts or in the organic phase.
  • nonpolar solvents (L) adding one or more nonpolar solvents (L) to the product-containing phase.
  • the additional solvent (L) can be added before, during or after the process steps a1), a2), a3) and a4). This measure serves to reduce the solubility of the respective salts in the organic phase.
  • the nonpolar solvent is added after process step a3), the salts precipitated in this step are separated in an additional separation step, eg filtration.
  • the amounts of salt to be separated off are extremely small compared with the original amount of salt in step a3), and the separation is correspondingly simple.
  • the addition of the nonpolar solvent is carried out before or during step a3), the respective salts from the product phase are forced into the liquid phase, which essentially consists of the halide of the base (B), and are separated together therewith.
  • halides of the base (B) remain in the organic phase during the phase separation in step a3), these are preferably removed by distillation. The same applies to the solvent (L) additionally added if necessary in step a5).
  • a recovery or recycling of the amine of general formula (4) used in step a) optionally in excess and of the amine released in step a2) takes place. If the amine of general formula (4) wholly or at least in part can not be obtained by a simple distillation in sufficient cleanliness, the interfering products, by-products or even residues of in
  • Step a2) added base (B) are separated by one or more further purification steps.
  • a recovery of the base (B) used in step a2) is preferably carried out by salification of the
  • the respective bases in bulk or in aqueous or non-aqueous solution or suspension
  • Ethylenediamine used as the base (B) this separation by distillation is preferably carried out at such high pressure that ethylenediamine and water no longer form an azeotrope.
  • the base (B) is a compound, e.g., an amine which is itself reactive with the silane of the general formula (5)
  • the amine of the general formulas (4) is preferably purified by the said process steps so far that the content of the base (B) in the amines of the general formulas (4) is less than 3%, preferably less than 1% and especially less than 0.5%.
  • the amine of the general formula (4) is used in excess, wherein the excess amine is removed by a step a4) by distillation substantially or at least in parts.
  • the base (B) is added (step a2)) and the salt phase separated (step a3)).
  • the amine of general formulas (2) liberated in step a2) is removed by distillation.
  • the distillate of the amine of the general formula (4) is preferably obtained with such high purity that it is used directly again without further purification.
  • the process step a) both batchwise, eg in stirred tanks, as well as be carried out continuously. The latter z. B.
  • Contacting the product of general formula 6 with water in the second process step (a6) can be carried out by any means known to those skilled in the art. This can be done either discontinuously or continuously.
  • the product of general formula 6 can be stirred or shaken together with water to ensure a particularly good distribution of the components of such a mixture.
  • a particularly preferred embodiment of the process according to the invention is the continuous contacting by passing the product of the general formula 6 through a reaction tube in which optionally also static mixers can be present.
  • the product of the general formula 6 is brought into contact with water in a loop reactor, it being possible where appropriate for the mixing to be improved by static mixers.
  • the ratio of the product of general formula 6 to water. can be targeted by the expert with regard to the desired Properties of the final product can be selected. In this case, the molar amount of water must be sufficient in order to reactivate all hydrolyzable groups R 'present in the product of the general formula 6.
  • the second step (a6) of the process according to the invention can also be carried out in the presence of further hydrolysis-labile compounds of the general formula 7.
  • the second step (a6) of the process according to the invention can also be carried out in the presence of a solvent inert to the reactants.
  • solvents are at 20 ° C (1013 mbar) liquid hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, methylene chloride, petroleum ether.
  • the second step (a6) of the process according to the invention is preferably carried out at temperatures of 20 to 200 ° C., in particular 20 to 100 ° C. More preferably, the reaction temperature is in a range of 40-80 ° C.
  • the residence time T 'in the reaction vessel can be selected from a range of 1 second ⁇ T' ⁇ 24 h.
  • the residence time T ' is in a range of 60 minutes ⁇ T' ⁇ 600 minutes, more preferably in a range of 120 minutes -5 T '-5 480 minutes.
  • the hydrolyzable group R "which is released during the hydrolysis can be separated off either directly in gaseous form or dissolved in an excess of water in its protonated form HR.”
  • the separation can be carried out by any type known to the person skilled in the art.
  • reaction may be carried out by any means known to those skilled in the art. This can be done both discontinuously and continuously.
  • the ratio of the product of the general formula 9 with linear or cyclic siloxanes can be selected by the person skilled in the art specifically with regard to the desired properties of the end product.
  • the reaction may also be in the presence of a solvent inert to the reactants be performed.
  • solvents are at 20 ° C (1013 mbar) liquid hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, methylene chloride, petroleum ether.
  • no additional solvent is used.
  • this step is carried out at temperatures of 20 to 200 ° C, especially at 20 - 150 ° C. More preferably, the reaction temperature is in a range of 40-120 ° C.
  • the residence time T 'in the reaction vessel can be selected from a range of 1 second ⁇ T' ⁇ 24 h.
  • the residence time T ' is in a range of 60 minutes ⁇ T' ⁇ 600 minutes, more preferably in a range of 120 minutes ⁇ T ' ⁇ 480 minutes.
  • Suitable catalyst K for the equilibration is any suitable compound known to the person skilled in the art.
  • equilibration catalysts examples include alkali metal hydroxides, in particular potassium, rubidium and cesium hydroxide, alkali metal alcoholates, quaternary ammonium hydroxides, such as tetramethylammonium hydroxide (TMAH) or its pentahydrate, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide.
  • TMAH tetramethylammonium hydroxide
  • TMAH tetramethylammonium hydroxide
  • benzyltrimethylammonium hydroxide benzyltrimethylammonium hydroxide.
  • Ethylammoniunihydroxid also mixtures thereof, as aqueous or alcoholic solution, Benzyltrimethylammoniumbutylat, ß- hydroxyethyltrimethylammonium 2-ethylhexanoat, quaternary phosphonium hydroxides, such as tetramethylphosphonium hydroxide, tetra- ethylphosphonium hydroxide, tetra-n-butylphosphonium hydroxide and tri-n-butyl-3- [tris - (trimethylsiloxy) silyl] -n-propyl-phosphonium hydroxide, their mixtures, and their silanolates and siloxanolates.
  • quaternary phosphonium hydroxides such as tetramethylphosphonium hydroxide, tetra- ethylphosphonium hydroxide, tetra-n-butylphosphonium hydroxide and tri-n-butyl-3- [tri
  • the alkali metal hydroxides are particularly preferably NaOH, KOH or quaternary ammonium hydroxides, such as tetramethylammonium hydride or benzyltrimethylammonium hydroxide.
  • the equilibration step is preferably carried out with the greatest possible exclusion of atmospheric moisture and preferably in an inert gas atmosphere, such as e.g. Nitrogen and noble gases, preferably nitrogen or argon performed.
  • an inert gas atmosphere such as e.g. Nitrogen and noble gases, preferably nitrogen or argon performed.
  • the reaction mixture obtained can be worked up by any desired methods known hitherto.
  • the calibration catalyst K is deactivated and / or
  • the equilibration catalyst K is deactivated after the end of the equilibration.
  • the reaction mixture is preferably treated thermally, more preferably at least one or more hours heated to 150 ° C.
  • the pressure is first lowered, preferably to 500 to 800 mbar, then on is lowered, preferably to 0.1 to 10 mbar, wherein the cleavage products of the catalysts and further volatile compounds are distilled off. Subsequently, the thus obtained, turbid reaction mixture is filtered, the filtration
  • Catalyst is after equilibration b2) the reaction mixture with inorganic or organic acids or neutralized with CO2 and the salts are then filtered, the filtration can optionally be carried out under an elevated pressure of preferably 2 to 5 bar, to obtain a clear, colorless liquid.
  • amino-siloxane compositions and processes for their preparation shown here have the advantage that the resulting costs can be minimized by economies of scale. Further, the amino-siloxane compositions have relatively low viscosity, high thermal stability, and can be readily provided by the synthetic methods disclosed herein.
  • Formulas is the silicon atom tetravalent.
  • Salt phase (ethylenediamine hydrochloride) at 90 ° C in one
  • Salt phase (ethylenediamine hydrochloride) at 90 ° C in one
  • Octamethylcyclotetrasiloxane presented at 25 ° C. To this mixture was added 0.1 g (0.6 mmol) of tetramethylammonium hydroxide
  • Viscosity (DIN 51562-1) 69 mm2 / s

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Abstract

L'invention concerne des aminosiloxanes (A) de formule générale 1 R1-NH- (CH2)n-R2 2Si-O-[SiR3 2-O]m-SiR2 2-(CH2)n-NH-R4 (1), dans laquelle R1, R4 représentent, indépendamment l'un de l'autre, un radical hydrocarboné substitué ou non substitué, saturé ou insaturé, ramifié ou non ramifié, linéaire ou cyclique, aliphatique ou aromatique, comprenant 1-20 atomes de carbone, un ou plusieurs motifs de méthylène, qui ne sont pas adjacents à un autre hétéroatome choisi dans le groupe contenant N, O, S et P, peuvent être remplacés par un hétéroatome choisi dans le groupe contenant N, O, S et P, R2, R3 représentent, indépendamment l'un de l'autre, un radical hydrocarboné substitué ou non substitué, saturé ou insaturé, ramifié ou non ramifié, linéaire ou cyclique, aliphatique ou aromatique comprenant 1-20 atomes de carbone, n représente un nombre valant 1 ou 2 et m représente un nombre identique ou supérieur à 0 ; un procédé pour la préparation des aminosiloxanes (A) et leur utilisation pour l'apprêt de textiles, pour des formulations cosmétiques, le traitement de surface, pour la préparation de copolymères séquencés ou pour la fixation et l'élimination de dioxyde de carbone de gaz d'échappement.
PCT/EP2016/074062 2016-10-07 2016-10-07 Aminosiloxanes secondaires et son procédé de production Ceased WO2018065070A1 (fr)

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WO2024123784A1 (fr) * 2022-12-06 2024-06-13 Ge Infrastructure Technology Llc Synthèse de disiloxanes à substitution aminoalkyle

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WO2024123784A1 (fr) * 2022-12-06 2024-06-13 Ge Infrastructure Technology Llc Synthèse de disiloxanes à substitution aminoalkyle

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