EP2531547A1 - Nouveau siloxane organomodifié possédant des fonctions amine primaires, nouveau siloxane organomodifié possédant des fonctions ammonium quaternaires et leur procédé de production - Google Patents

Nouveau siloxane organomodifié possédant des fonctions amine primaires, nouveau siloxane organomodifié possédant des fonctions ammonium quaternaires et leur procédé de production

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Publication number
EP2531547A1
EP2531547A1 EP10798357A EP10798357A EP2531547A1 EP 2531547 A1 EP2531547 A1 EP 2531547A1 EP 10798357 A EP10798357 A EP 10798357A EP 10798357 A EP10798357 A EP 10798357A EP 2531547 A1 EP2531547 A1 EP 2531547A1
Authority
EP
European Patent Office
Prior art keywords
ammonium
radicals
group
ammonia
formula
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Withdrawn
Application number
EP10798357A
Other languages
German (de)
English (en)
Inventor
Frauke Henning
Wilfried Knott
Horst Dudzik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Goldschmidt GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Evonik Goldschmidt GmbH filed Critical Evonik Goldschmidt GmbH
Publication of EP2531547A1 publication Critical patent/EP2531547A1/fr
Withdrawn legal-status Critical Current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
    • C07F7/18—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen

Definitions

  • Novel organomodified siloxanes with primary amino functions novel organomodified siloxanes with quaternary ammonium functions and the process for their preparation
  • the invention relates to novel organomodified siloxanes having primary amino functions and to novel organomodified siloxanes having quaternary ammonium functions and to the process for their preparation.
  • Aminoalkyl-functional alkoxysilanes are used as adhesion promoters in coatings or adhesives and sealants. They are prepared by the platinum (0) -catalyzed hydrosilylation of allyl chloride, as described by way of example in DE 10104966 A1. Due to side reactions arise propene, chloropropane and propylchlorosilane, so that a distillative purification of the product is required.
  • the haloalkyl of the thus obtained 3-Chlorpropylchlorsilane can be further functionalized according to EP 1273612 A1 manifold, for example by reaction with ammonia, hydrogen sulfide, alkali metal or ammonium sulfides, -rhodaniden, or methacrylates.
  • the functional chlorosilanes can be converted into the corresponding alkoxysilanes.
  • the method often require high amounts of catalyst and lead due to rearrangements of the double bonds and limited addition selectivities to product mixtures consisting of the branched alpha and beta as well as the linear gamma isomer of aminopropylsilane.
  • the silane mixtures must be purified by distillation before further use. Due to the comparatively high amounts of catalyst and the yield losses owing to the side reactions and the required distillative purification, the hydrosilylation of allylamine is associated with high costs.
  • Aminopropylalkoxysilanes can be converted to polysiloxanes by means of hydrolysis and condensation reactions. Due to the basic amino function, preference is given to using alkaline catalysts, such as, for example, KOH, ammonium hydroxide or carboxylate.
  • alkaline catalysts such as, for example, KOH, ammonium hydroxide or carboxylate.
  • EP 1580215 A1 and the documents cited therein are hereby incorporated by reference.
  • This synthesis route has limitations. In the synthesis of aminofunctional polysiloxanes with high functionality density, the price of the expensive specialty silane increasingly increases the cost of the material and at the same time the yield is reduced by the amount of alcohol liberated during the hydrolysis. In the case of base-catalyzed equilibration reactions of polysiloxanes with amino groups, it is furthermore possible for silazanes to occur as by-products.
  • EP 1008614 A2 claims linear polydimethylsiloxanes whose chain ends are each SiC-linked with an allyl polyether and an alkanolamine or alkanolalkylamine are.
  • the preparation is carried out from a linear, epoxy- and polyether-functional polydimethylsiloxane by titanium-catalyzed epoxide ring opening, for example with diethanolamine at 80 ° C.
  • Polysiloxanes with primary amino functions are not preparable and unreacted by the described procedure.
  • US 2008/0314518 A1 describes the reaction of amino-functional silanes or ethylenediamine in situ with glycidoxypropyltriethoxysilane for the preparation of an aqueous two-component adhesion promoter.
  • the crosslinking required for good adhesion is ensured because an amino function reacts with more than one of the excess epoxy rings added.
  • the prior art discloses siloxanes having no more than two amino functions and poorer synthetic groups.
  • Aminofunctional siloxanes and in particular their charged derivatives which are accessible to quaternary nitrogen compounds by reaction of the amino function with various acids or else by their alkylation, have pronounced electrostatic affinity towards surfaces and consequently ensure good substantivity of the compounds.
  • the substantivity of the aminosiloxane as its ability to electrostatically anchor on substrates goes hand in hand with its density of functionality, ie. with the number of uncharged or even charge-carrying nitrogen functions based on the molecular weight.
  • the goal of providing aminosiloxanes of arbitrary substantivity is to state that the prior art lacks selective and inexpensive synthetic approaches to siloxanes containing more than one or two primary amino functions per siloxane chain.
  • the epoxide ring opening with ammonia does not remain at the stage of the primary amine.
  • the formed primary and secondary amines are stronger nucleophiles and compete with the ammonia for reaction with the epoxide ring.
  • the amino-functional polysiloxanes described in EP 1 00861 4 A2 are of low molecular weight and have only one terminal amino function per chain.
  • the EP 1 956038 A1 also describes only linear terminal amino-functional intermediates. Subsequent reactions of the primary amines formed in the first case lead to chain extension and not to cross-linking control.
  • An object of the present invention is to selectively and inexpensively produce siloxanes having primary amino functions and other organomodifications.
  • the aim is to ensure a high yield of primary amino acids while avoiding the formation of secondary amines.
  • Another object of the present invention is to develop a low cost process for producing high chemoselectivity siloxanes for the formation of primary amino groups.
  • An object of the invention is therefore a process for the preparation of siloxanes carrying selectively primary amino groups by reacting laterally epoxy-modified siloxanes with gaseous, dissolved or in situ generated ammonia.
  • Another object of the present invention is to modify siloxanes not only at the chain ends but also laterally with primary amino functions to achieve higher functionality densities.
  • the invention relates to siloxanes of the general formula 1
  • a 0 to 32; preferably 1 to 22, in particular 2;
  • a1 0 to 10, preferably 1 to 5, in particular 2;
  • a2 0 to 32; preferably 1 to 22, in particular 2;
  • a3 0 to 10; preferably 1 to 5, in particular 2;
  • b 0 to 600, preferably 10 to 500, in particular 20 to 400
  • b1 0 to 50, preferably 0.1 to 20, in particular 2 to 10;
  • b2 0 to 50, preferably 0.1 to 20, in particular 1 to 10;
  • b3 0 to 50, preferably 1 to 20, in particular 2 to 10;
  • b1 + 0 and / or b2 + 0 and / or b3 ⁇ 0 and / or a2 ⁇ 0 and / or a3 is 0 and it is preferred that at least two of the factors a2, a3, b1 , b2, and b3 ⁇ 0. independently of one another identical or different linear or branched hydrocarbon radicals having 1 to 30 carbon atoms or else aromatic hydrocarbon radicals having 6 to 30 carbon atoms, preferably methyl or phenyl, in particular methyl; independently of one another identical or different organic radicals which carry a primary amino function, preferably radicals which, in addition to the amino function, carry a hydroxyl group, in particular selected from the group
  • x 0 to 100 preferably> 0, in particular 1 to 50
  • y is 0 to 100, preferably> 0, in particular 1 to 50,
  • R ' is independently of one another an optionally substituted, for example, alkyl, aryl or haloalkyl or haloaryl substituted, alkyl or aryl group having 1 to 12 carbon atoms, wherein within a radical R 4 and / or of a molecule of the formula I with each other Substituents R 'may be present, and
  • R IV a given substitute, eg. B. halogen-substituted, saturated or unsaturated hydrocarbon radical having from 1 to 50, preferably from 3 to 30, carbon atoms, in particular a decyl, dodecyl, tetradecyl or hexadecyl radical, independently of one another, identical or different linear, cyclic or branched, optionally olefinic unsaturated or aromatic hydrocarbon radicals having from 1 to 30 carbon atoms, which are with the, Heteroatoms O, N, S, P containing groups or halogen atoms may be substituted and preferably no primary or secondary amine functions, preferably alkanol radicals, carboxylic acid radicals or carboxylic acid ester radicals, in particular hydrocarbon radicals having 5 to 30 carbon atoms such as a dodecenyl, tetradecyl, hexadecyl - or octadecyl and
  • R 5 independently of one another are identical or different radicals R 1 , R 2 , R 3 or R 4 , preferably R 1 , in particular methyl, phenyl, dodecyl or hexadecyl.
  • the various monomer units of the structural units indicated in the formulas can be constructed in blocks with any number of blocks and any sequence or statistical distribution.
  • the indices used in the formulas are to be regarded as statistical averages.
  • the invention further ionic adducts of the amino-functional siloxanes of the invention with protic reactants H + A ".
  • the adduct is in the form -NH 3 + A" before.
  • the anions A " are identical or different counterions to the positive charges on the protonated, primary amino groups selected from inorganic or organic anions of the acids H + A " , and their derivatives.
  • Preferred anions are, for example, chloride, sulfate and hydrogen sulfates, carbonate and bicarbonate, phosphate and hydrogen phosphates, acetate and homologous carboxylates with linear or branched, saturated or olefinically unsaturated alkyl chains, aromatic carboxylates, carboxylates formed from amino acids, citrates, malonates, fumarates, maleates, substituted ones and unsubstituted succinates and carboxylates formed from L-hydroxycarboxylic acids, such as lactate.
  • the aminosiloxanes and their ionic adducts according to the invention can be present in dissociation equilibria.
  • the invention furthermore relates to the quaternary ammonium compounds of the formula 2 deriving from the alkylation of the primary amine function
  • radicals R 1 , R 3 , R 4 and R 5 likewise fulfill the abovementioned definition, and
  • R 8 independently of one another, identical or different organic radicals carry the ammonium functions;
  • suitable radicals R 8 are preferably identical or different radicals selected from the group
  • OR 9 are independently identical or different linear or branched hydrocarbon radicals having 1 to 30 carbon atoms or aromatic hydrocarbon radicals having 6 to 30 carbon atoms, preferably methyl or ethyl;
  • the compounds of the formula 1 according to the invention are reacted with the alkylating reagents.
  • the alkylating reagents for this purpose, in particular known to those skilled Alkyl miching reagentien such.
  • the invention furthermore relates to preparations in the form of solutions, emulsions, dispersions and / or mixtures comprising the compounds of the formulas 1 or 2 according to the invention. These preparations may contain further additives and Aggregates include, for example, but not limited to selected from the group of fillers, emulsifiers, dyes, pigments.
  • the invention further relates to the use of the aminofunctional siloxanes of the formulas 1 or 2 according to the invention as emulsifiers for cosmetic preparations, compatibilizers for plastic blends, release agents, water repellents, dispersants for color pigments and fillers, additives for textile finishing (plasticizers), conditioners for hair, primers for Surface coating / adhesion promoter, additive for corrosion protection formulations, PU foam stabilizer, defoamer and / or wetting agent.
  • Another object of the invention is the process for the preparation of the aminosiloxanes of the formula 1 according to the invention.
  • the compounds of the formula I according to the invention are prepared from epoxy-functional compounds of the formula 3
  • radicals R 1 , R 3 , R 4 and R 5 likewise fulfill the abovementioned definition
  • R 10 are independently identical or different organic epoxy radicals.
  • Suitable epoxy radicals R 10 are for example preferably identical or different radicals selected from the group
  • the epoxy-functional siloxanes which can carry further substituents are prepared as described in the prior art-for example in EP 0415208 A2-by means of transition metal-catalyzed hydrosilylation. Subsequently, the ring-opening reaction is carried out with introduction of ammonia, with or without use of solvents, at atmospheric pressure or in an autoclave at overpressure.
  • the ammonia can also be generated in situ from compounds which split off ammonia, for example when the temperature increases.
  • a variety of common solvents is suitable for the preparation according to the invention of the amino-functional siloxanes.
  • the solvent is selected according to its solubility for starting material and product.
  • the solvent should behave substantially inert to both the ammonia and the epoxy-functional precursor under the chosen reaction conditions.
  • aromatic hydrocarbons but also ethers or alcohols are suitable.
  • Toluene, xylene, methanol, ethanol, propanol and its isomers, in particular 2-propanol, are preferably used.
  • higher reaction temperatures of up to 150 ° C preferably 60 ° C to 130 ° C can be set because the reaction gas remains in the closed system.
  • the pressure build-up in the closed autoclave during heating in the range of 1 to 50 bar, preferably 5 to 20 bar.
  • a closed pressure reactor is filled with ammonia gas via a gassing device, a predetermined pressure of 1 to 50 bar, preferably 5 to 20 bar, can be set during the filling.
  • the reaction times may in this case be 1 to 10 hours, preferably 1 to 5 hours.
  • a particular advantage of the process at pressures of greater than 1 bar and at temperatures above 50 ° C. is that shorter reaction times of less than 12 hours can be achieved in comparison with the prior art.
  • the higher local concentration of ammonia in the dissolved phase also has a positive influence on the selectivity, since the ratio of ammonia to the primary amine formed, ie the reagents competing for the ring opening, is increased in favor of the ammonia.
  • Preferred process pressures are in the range of 2 to 50 bar, in particular 5 to 20 bar.
  • reaction is carried out without pressure, then a minimum temperature of 50 ° C, preferably of 60 ° C, required for a rapid reaction with acceptable selectivity.
  • pressureless reaction it may be advantageous to accelerate the epoxy ring opening by means of suitable catalysts.
  • suitable catalysts it is possible to use heterogeneous or homogeneous catalysts from the range of acids, Lewis acids or bases as well as metal salts or complexes, or transition metal salts or complexes.
  • the reaction can be carried out in a one-pot process or else continuously. After completion of the reaction, the product is distilled to remove residual ammonia and optionally also the solvent used.
  • a pH adjustment can be carried out by means of solid or dissolved buffer systems. If a pH value adjustment with solid salts is carried out, this is followed by a fi ltration step. It is not necessary to carry out a filtration in the case of the starting of the roducts.
  • Ammonia can be used as a reagent not only molecular gaseous or in the form of a saturated solution, but can also be used in chemically bound form.
  • amine and / or ammonium compounds which liberate ammonia at elevated temperatures with decomposition or else in ammonia in solution, for example ammonium halides, ammonium carbonate and / or or -hydrogencarbonate, ammonium sulfate and / or hydrogen sulfate, ammonium sulfamate, ammonium phosphate, hydrogen peroxide and / or dihydrogen phosphate, ammonium cyanate, ammonium carboxylates such as ammonium acetate, ammonium hydrogen oxalate and / or oxalate, ammonium hydrogen citrate, ammonium benzoate , Ammonium formate, ammonium carbamate, ammonium lac
  • ammonia can be generated in situ from hydroxylamine, hydroxylamine-O-sulfonic acid or amidosulfonic acid or urotropin (hexamethylenetetramine) by decomposition under the chosen reaction conditions.
  • carboxylic acid amides or carbamates can be formed by subsequent reactions on the amine function formed and / or carboxylic acid esters or corresponding sulfuric acid esters or phosphoric acid esters on the hydroxyl function formed.
  • compounds such as, for example, organomodified polysiloxanes, which may have multiple monomer units in multiple, may be randomly distributed (random oligomer) or ordered (block oligomer) in these compounds. Information on the number of units in such compounds is to be understood as statistical averages, averaged over all corresponding compounds.
  • the gas volumetrically determined conversion is quantitative after 2 hours. After distillation on a rotary evaporator at 10 to 20 mbar and 140 ° C to obtain a clear, liquid product having an epoxide content of 0.32 wt .-% epoxy-oxygen.
  • a gel bes, liquid product with an amine content of 0.2 wt .-% of primary amine nitrogen (theor., 0.27%, 74% yield), ⁇ 0.01% by weight of secondary amine nitrogen and 0.14% by weight of tertiary amine nitrogen (theor. 0.16% by weight of methylimidazole).
  • a slightly cloudy, yellowish product having a viscosity of 3209 mPa * s at 25 ° C. and an amine content of 0.35% by weight is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un procédé de production de siloxanes portant sélectivement des groupes amino primaires par réaction avec de l'ammoniac et les composés ainsi produits.
EP10798357A 2010-02-03 2010-12-29 Nouveau siloxane organomodifié possédant des fonctions amine primaires, nouveau siloxane organomodifié possédant des fonctions ammonium quaternaires et leur procédé de production Withdrawn EP2531547A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010001531A DE102010001531A1 (de) 2010-02-03 2010-02-03 Neuartige organomodifizierte Siloxane mit primären Aminofunktionen, neuartige organomodifizierte Siloxane mit quaternären Ammoniumfunktionen und das Verfahren zu deren Herstellung
PCT/EP2010/070855 WO2011095261A1 (fr) 2010-02-03 2010-12-29 Nouveau siloxane organomodifié possédant des fonctions amine primaires, nouveau siloxane organomodifié possédant des fonctions ammonium quaternaires et leur procédé de production

Publications (1)

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EP2531547A1 true EP2531547A1 (fr) 2012-12-12

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Country Status (8)

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US (2) US20120282210A1 (fr)
EP (1) EP2531547A1 (fr)
JP (1) JP2013518945A (fr)
CN (1) CN102741326B (fr)
BR (1) BR112012019049A2 (fr)
CA (1) CA2788748A1 (fr)
DE (1) DE102010001531A1 (fr)
WO (1) WO2011095261A1 (fr)

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WO2011095261A1 (fr) 2011-08-11
US20150080593A1 (en) 2015-03-19
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JP2013518945A (ja) 2013-05-23
DE102010001531A1 (de) 2011-08-04
BR112012019049A2 (pt) 2016-09-13
US9695202B2 (en) 2017-07-04
CN102741326B (zh) 2015-07-15
CA2788748A1 (fr) 2011-08-11

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