DE102012011034A1 - New silicate-phosphate materials useful e.g. as components for optical or optoelectronic applications, preferably glasses with special properties, and for controlled release fertilizers, and as adhesion promoter for coating organic polymers - Google Patents

Abstract

Silicate-phosphate materials (I) are new. Silicate-phosphate materials of formula (A b+>) n/b[(Si1) x(Si2) y(P1) zO (2x+2y+2.5z+n/2-m/2-s/2)(R11) m(R12) s](n ->) r (I) are new. A : cation; R11, R12 : alkyl or aryl (both optionally functionalized), OR, halo or OH; Si1 : hexa-coordinated Si; Si2 : tetra-coordinated Si; P1 : tetra-coordinated P; b : 1-3 (for low-molecular weight cations) or greater than 1 (for polymeric cations); n : 0-12; x, y : 0-12; and z : 1-12; or x+y : greater than z (excess of alkoxy- or halosilane); m, n, s : 0, 1-12; and r : >= 1. Independent claims are also included for: (1) preparing (I); (2) preparing molecular, oligomeric and polymeric silicate-phosphate materials, comprising reacting anhydrous phosphoric acid with a higher alkoxy- and/or chlorosilane having more than one silicon atom, or with a monosilane; and (3) use of (I) as a component for optical and/or optoelectronic applications, preferably transparent materials or glasses with special properties e.g. refractive index, density, transparency and chemical resistance, where specific functions are caused by material intrinsic properties or by the properties of fillers and/or molecular or polymeric additives, preferably laser dyes or luminescent components.

Description

The present invention relates to a class of substances consisting of phosphate units and silicon as the second or third main component (in addition to oxygen and phosphorus) and varying proportions of carbon and hydrogen and optionally further hetero elements such as nitrogen and / or metals. In addition to the described class of substances and methods for producing the class of substance different uses are claimed.

Phosphates or orthophosphates contain the PO ₄ unit and are derived from the orthophosphoric acid H ₃ PO ₄ , which contains the P atom without exception in the oxidation state +5 [1]. Furthermore, numerous oligo- and polyphosphates, phosphoric acid esters and the phosphorus pentoxide P ₂ O ₅ belong to the class of compounds which contains the mentioned PO _{4 building} blocks. Of technical importance are, inter alia, phosphate glasses, which are usually three-crosslinking per PO ₄ unit due to the five-valence of phosphorus [2]. According to their structure, such glasses can be divided into three groups: glasses with long phosphate chains, glasses with shorter phosphate chains and glasses with phosphate invitglass structures [1]. Another subdivision into glasses with poly, meta- and ultraphosphate structures.

The majority (80%) of the white phosphorus produced is burned to phosphorus (V) oxide, which is used as the starting material for phosphoric acid production and for the preparation of various phosphates [3]. Phosphoric acid can be formed by condensation reactions (dehydration) of diphosphoric acid (H ₄ P ₂ O ₇ ) and corresponding salts forming diphosphates (pyrophosphates) M ' ₄ P ₂ O ₇ . In a continued reaction, poly- or cyclo-phosphates are formed. Cyclophosphates are often called metaphosphates. Polyphosphates and metaphosphates are therefore polymers of the salts of phosphoric acid [4]. In the presence of alkoxysilanes, however, preference is given to the formation of Si-OP groups with elimination of alcohols.

Orthophosphates and related phosphorus compounds are used for numerous applications. Among them are u. a. Flame retardant [5] for the plastics, wood and textile industry. In terms of quantity, the greatest importance for the use of phosphates lies in the areas of fertilizers, detergent and food additives as well as feed and corrosion inhibitors [3]. Furthermore, phosphorus-containing silicate glasses are the starting material for bioactive and biocompatible glass ceramics and hybrid materials (bone substitutes and dentures) [2b].

Anhydrous phosphoric acid itself is mainly used (80-90%) for the production of industrial phosphates such as calcium or sodium phosphate [6]. It is also used in the acidification of beverages and in the treatment of metal surfaces [6], as well as in phosphoric acid fuel cells (PAFC, Phosphoric Acid Fuel Cell) [7]. Crystalline, anhydrous phosphoric acid is also known as a reagent in the biochemical field [8, 9] and as a catalyst in hydrocarbon rearrangement process [10], z. B. the Friedel-Crafts alkylation.

Almost all silicates are based on tetrahedral SiO ₄ units, which are linked exclusively via vertices, ie Si-O-Si units, and contain the Si atoms in the oxidation number + IV [11]. Edges or even surface joins are virtually absent in silicates. Rarely one encounters SiO _{6 building} blocks in silicates. Here, the silicon atom is octahedrally coordinated or "hypercoordinated".

The silicates can be derived from the monosilicic acid H ₄ SiO ₄ . Condensation gives rise to amorphous and (partly) crystalline islet, group, ring, chain, band-layer and framework silicates, which as a rule contain metals as counterions in addition to the elements oxygen, hydrogen and silicon. But even without additional metals are starting from the silica very many commercially relevant materials available whose properties are usually determined by the strong morphology. Porous silica gels and fumed silica find z. As applications as adsorbents, for drying, storage or cleaning of gases, liquids and solids, for the purification and decolorization of liquids, for detoxification, for gelatinization, for chromatographic separation or as matting agents in paints, coatings and plastics. Furthermore, silicate (hybrid) materials find a wide variety of applications as components for building materials. Silica hybrid materials, ceramics and glasses are used in many mass markets, for example as a matrix or filler. In addition, many "high technology fields" are known, including in the fields of semiconductor devices, high temperature resistant materials or glass fibers.

In the literature, three classes of substances are mentioned, which in addition to tetrahedral SiO ₄ units also contain phosphate units and partially six-coordinate silicon. So there are a few crystalline phases such as SiP ₂ O ₇ , Si ₅ P ₆ O ₂₅ , and RbSiP ₄ O ₁₃ [12, 13, 14]. These differ from the SiPOs according to the invention in that they contain no terminal radicals R.

In addition, there are phosphate-silicate glasses, which are obtained from melts at correspondingly high temperatures [15]. These also contain no terminal organic radicals R. They can contain significant amounts of hydroxyl groups and even water despite the high production temperatures.

Another group of silicate-containing phosphate materials mentioned in the literature can be prepared under aqueous conditions by the sol-gel process [16]. The materials thus contain larger amounts of water. It can not produce anhydrous SiPOs.

The invention has for its object to develop new materials that contain not only tetrahedral SiO ₄ units but also phosphate units and partially six-coordinate silicon and can be easily produced. By combining the properties of the phosphate and silicate-based materials, new fields of application for these substances should be demonstrated.

According to the invention the object is achieved by compounds of the general formula {A ^{b +} _{n / b} [Si ^VI _x Si ^IV _y Si ^IV _z O _{(2x + 2y + 2.5z + n / 2 -m / 2- s / 2)} R ' _m R'' _s ] ^n- (Solvent) _p · (other components such as fillers / organic polymers) _q } _r . correspond, solved, being
A = cation,
R 'and R''independently of one another = OR (alkoxy), halogen, OH, alkyl (if appropriate functionalized), aryl (if appropriate functionalized)
and
b = 1 to 3 for low molecular weight cations and b> 1 for polymeric cations
n = 0 to 12
x = 0 to 12 where x + y> z (excess of alkoxy- or halosilane)
y = 0 to 12;
z = 1 to 12;
m = 0.1 to 12,
s = 0.1 to 12.

The variables "p" and "q" are independently equal to or greater than zero and allow flexible proportions of solvents, molecular or polymeric compounds as well as active and passive fillers to be part of the materials according to the invention. The variable "r" may be equal to or greater than one and indicates that the SiPOs of the invention may be molecular or polymeric substances.

The Roman numerals in the general formula mean
Si ^IV = hexahedral (octahedral) coordinated silicon atoms,
Si ^IV = fourfold (tetrahedral) coordinated silicon atoms,
P ^IV = quadruple (tetrahedral) coordinated phosphorus atoms.

The cation A can be a mono-, di- and trivalent metal cation, ie M ¹⁺ , M ²⁺ and M ^{3 +} , a complexed metal cation with monodentate ligands, ie, for example, [M (L) ₆ ] ⁺ or a complexed metal cation with be multidentate chelating ligands. Also possible are a complex cation such as ammonium ions, ie NR ₄ ⁺ or NRR'R''R ''' ⁺ , oxonium ions, phosphonium ions, etc. as well as all protonated (neutral) bases such as pryridinium ions, etc. as well as oligomeric and polymeric cations such as z. [RR'R''N- (R '''-NRR') _n -NRR'R ''] ^{(n + 2) +}

To make the formula more comprehensible, is on the to directed. The following example structures for the claimed class of substance or the general formula of the SiOPs according to the invention are listed:

: A ¹⁺ ₆ [Si ^VI ₃ S ^IV ₁₂ P ^IV ₁₈ O _{(6 + 24 + 45 + 3 - 6 - 0)} (OEt) ₁₂ R '' ₀ ] ^6-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₆ P ^IV ₉ O _{(2 + 12 + 22.5 + 1 -} 1.5-3) (OH) ₃ (OEt) ₆ ] ^2-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₆ P ^IV ₆ O _{(2 + 12 + 15 + 1 - 3 - 3)} (OEt) ₆ Me ₆ ] ^2-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₆ P ^IV ₆ O _{(2 + 12 + 15 +} 1-6-0) (OEt) ₁₂ R " ₀ ] ^2-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₉ P ^IV ₆ O _{(2 + 18 + 15 +} 1-6-0) (OEt) ₁₂ R " ₀ ] ^2-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₉ P ^IV ₆ O _{(2 + 18 + 15 + 1 - 4.5 - 1.5} Me ₉ (OEt) ₃ ] ^2-

A ¹⁺ ₂ [Si ^VI ₁ Si ^IV ₆ P ^IV ₁₀ O _{(2 + 12 + 25 + 1 - 3 - 0)} Me ₆ R " ₀ ] ^2-

The main characteristic of these substances according to the invention is that they are prepared by reacting pure (ie anhydrous or crystalline) phosphoric acid with alkoxysilanes such as Si (OEt) ₄ (TEOS), Si (OMe) ₄ (TMOS), RSi (OR ') ₃ , R ₂ Si (OR ') ₂ and chlorine-containing alkoxysilanes such as ClSi (OR) ₃ or chlorosilanes etc. in anhydrous (water content <0.1%) organic solvents at room temperature or comparatively very low calcination temperatures can be produced. The novel synthetic approach allows the preparation of (anhydrous) hybrid polymers consisting of PO ₄ units (tetrahedra), SiO ₄ units (tetrahedra) and / or SiO ₆ units (octahedra) and RSiO ₃ - or R ₂ SiO ₂ - Units (tetrahedra having organic radicals or other substituents, ie R = H, alkyl, aryl, alkoxy, including functionalized variants having carbonyl, carboxyl, ether, ester, amide, halogen radicals or heterocycles, etc.) Anhydrous crystalline phosphoric acid is reacted in a dry organic solvent with an alkoxysilane such as TEOS or an alkoxysilane mixture, resulting in partial or complete elimination of alcohol compounds mainly PO-Si bridges and depending on the stoichiometric ratios and starting materials used also POP and / or Si Furthermore, the class of substance according to the invention contains different proportions of Si-OR end groups this end group is based on 24 silicon atoms or 12 phosphorus atoms 0.1 (ie x = y = z = 12 and m = s = 0.1 in the general formula on page 3). The SiPOs according to the invention are characterized in that they are prepared under virtually anhydrous conditions, and therefore the products contain no or only very small amounts of water. Since an alkoxysilane excess is generally used (Si-OR groups: P-OH group ratio> 1), all condensation reactions which can lead to water formation are suppressed. In addition, water leads to the formation of the corresponding alcohols under alkoxysilane hydrolysis. At the same time, due to their acidity, the POH groups present in the phosphoric acid tend to deprotonate and coordinate to SiO ₄ units to form more highly coordinated silicate units, especially SiO ₆ octahedra.

By subsequent to the synthesis of calcination or thermal aging of the products initially obtained at room temperature can be converted and modified, usually more crosslinked (ie higher condensed) structures arise. These contain less alkoxy and OH end groups per unit volume and more Si-OP and / or POP and / or Si-O-Si bridges. During synthesis, drying and thermal aging, the following chemical reactions occur predominantly (R = org. Substituent): ≡P-OH + RO-Si → PO-Si + ROH P-OH + P-OR → POP + ROH Si-OH + Si-OR → Si-O-Si + ROH

As well as, to a lesser extent, redistribution and exchange reactions: 2Si-OP → Si-O-Si + POP P-OH + Si-OR → P-OR + Si-OH

The following reactions are suppressed by the alkoxysilane excess, or run only to a small extent, ie the equilibria are far on the left: P-OH + ROH → P-OR + H ₂ O 2P-OH → POP + H ₂ O 2Si-OH → Si-O-Si + H ₂ O HO-Si + ROH → RO-Si + H ₂ O

In addition, the POH groups of the phosphoric acid can be bound by the use of auxiliary bases (preferably amines), which additionally suppresses the formation of free water. If chlorine-containing silanes are used, preference is given to using tertiary amines, such as triethylamine, as the "HCl scavenger". In addition, further reactions take place: Si-Cl + HO-P → Si-OP + HCl Si-Cl + ROH → Si-OR + HCl Si-Cl + H ₂ O → Si-OH + HCl HOl + Et ₃ N → [Et ₃ NH] Cl POH + Et ₃ N → [Et ₃ NH] OP

The deprotonation of the POH groups promotes the formation of SiO ₅ units. The molecular, oligomeric and / or polymeric structural units may be present ionically, ie as salts, or uncharged. Examples of syntheses of the SiPOs according to the invention are shown ,

The new class of compound is useful as an organic-inorganic hybrid material and / or glassy product, i. H. Base or matrix material for receiving different functional components such as pigments and / or (luminescent) dyes, magnetic components, optical brighteners, laser dyes, components of optoelectronic components, homogeneous or heterogeneous (photo) catalysts, active ingredients or nutrients, catalysts, etc. The SiPOs according to the invention Depending on the present morphology and composition with small amounts of additives or without additional components are used, for example as flame retardants, fire extinguishing agents, Kunstoffadditive, as an electrolyte, as (long-term) fertilizer or fertilizer component, for corrosion protection, as bioactive or biocompatible materials, as Adsorbents, support materials o. Ä., And as a starting material for other phosphorus, oxygen and silicon-containing materials.

The invention will be explained in more detail by means of the following exemplary embodiments: All reactions were carried out under protective gas (argon) using the standard Schlenk technique and predominantly under normal atmospheric conditions. Commercially available starting materials were used and dried according to the appropriate laboratory regulations.

Example 1: Synthesis SiPO-1.1

Under inert conditions, crystalline phosphoric acid (0.64 g, 6.5 mmol) (Aldrich) is dissolved in 46 ml of dried diethyl ether, followed by dropwise addition of Si (OEt) ₄ (1.59 g, 7.6 mmol, AcrosOrganics). During the addition, a white precipitate forms. After 96 hours of stirring at room temperature, the solid is separated using a Schlenk frit, washed with diethyl ether and dried under vacuum. ²⁹ Si NMR (79.51 MHz, CP MAS): δ = -101, -110, -212 ppm; ³¹ P-NMR (162.02 MHz, CP-MAS): δ = -0.6, -11.3, -22.5, -29.9 ppm; ¹³ C-NMR (100.65 MHz, CP-MAS): δ = 14.62, 17.72, 61.40 ppm; IR (KBr): v = 3600-2600 (s, v OH ··· H, v CH, br), 2380 (m, v P (O) CH, br), 1646 (m, δ P (O) OH , br), 1200-1000 (s, v Si-O, PO, Si-OP, CO, br) cm ^-1 .

Example 2: Synthesis of SiPO-1.2

In an oven 0.73 g SiPO-1.1 are heated under inert conditions (N ₂ ) to 500 ° C within 1.5 hours and held at this temperature for two hours. ²⁹ Si NMR (79.51 MHz, CP MAS): δ = -119, -212 ppm; ³¹ P-NMR (162.02 MHz, CP-MAS): δ = -43.5 ppm; (0.49 g, mass loss of 33%).

Example 3: Synthesis of SiPO-2

Under inert conditions, crystalline phosphoric acid (0.46 g, 4.7 mmol) (Aldrich) is dissolved in 20 ml of dried diethyl ether and triethylamine (1.43 g, 14.1 mmol) is added dropwise. This is followed by the addition of ClSi (OEt) ₃ (2.80 g, 14.1 mmol). The mixture is stirred for 72 hours at room temperature, the solid (NEt ₃ HCl) filtered off and the solvent separated by means of cold distillation. ¹ H-NMR (400.13 MHz, CDCl _3): δ 1.23 (6H, CH _3), 3.82, 3.94 (4H, CH ₂₎ ppm; ²⁹ Si NMR (79.49 MHz, CDCl _3): δ = -82.4 (s, Si (OEt) _4), -91.8 (d, ² J ⁽²⁹ Si ³¹ P) = 5.5 Hz, Si-OP) ppm; ³¹ P-NMR (161.98 MHz, CDCl _3): δ = -33.4 ppm.

Example 4: Production of SiPO-1.3

SiPO-2 is dissolved in chloroform and stored at 18 ° C. ₂₄ H ₆₀ O ₃₆ P ₆ Si ₇ .2 (C ₆ H ₁₆ N) .4 (CHCl ₃ ), M = 1989.04, triclinic, space group P-1, a = 11.4825 (3) Å, b = 15.5104 (4) Å, c = 25.7924 (8) Å, α = 94.538 (2) °, β = 98.483 (2) °, γ = 95.689 (2) °, V = 4500.4 (2) Å ³ , T = 200 (2) K , Z = 2, μ = 0.644 mm ^-1 , 71593 measured reflections, 20118 independent reflections (R _int = 0.0978). The final R values for I> 2σ (I) are: R ₁ = 0.0782, wR ₂ = 0.2207; for all data: R ₁ = 0.1218, wR ₂ = 0.2453. The "goodness off" against F ² is 1,069.

literature

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Claims (16)

Silicate-phosphate materials (SiPOs) of the general formula {A ^{b +} _{n / b} [Si ^VI _x Si ^IV y ^P IV _z O _{(2x + + 2.5z + n / 2-m / 2 -s / 2)]} R ' _m R'' _s ] ^n- } _r , where A = cation, R' and R '' independently of one another = OR (alkoxy), halogen, OH, alkyl (if appropriate functionalized), aryl (if appropriate functionalized) Si ^VI = hexahedral (octahedral) coordinated silicon, Si ^IV = quadruplet (tetrahedral) coordinated silicon, P ^IV = quadruple (tetrahedral) coordinated phosphor and b = 1 to 3 for low molecular weight cations and b> 1 for polymeric cations, n = 0 to 12, x = 0 to 12, where x + y> z (excess of alkoxy or halosilane) y = 0 to 12, z = 1 to 12, m = 0.1 to 12, n = 0.1 to 12 and r ≥ 1. Silicate-phosphate materials (SiPOs) according to claim 1, characterized in that variable proportions of solvents, molecular or polymeric compounds and active and passive fillers are included. Process for the preparation of silicate-phosphate materials (SiPOs) characterized in that anhydrous (crystalline) phosphoric acid H ₃ PO ₄ with alkoxysilanes (RO) _x SiR _4-x (x = 1-4) and / or chlorosilanes of the type Cl _x SiR _4-x (x = 1-4) in organic (anhydrous, H ₂ O contents <0.1%) solvents is reacted. Process for the preparation of molecular, oligomeric and polymeric silicate-phosphate materials (SiPOs), characterized in that anhydrous (crystalline) phosphoric acid H ₃ PO ₄ with higher alkoxy and / or chlorosilanes having more than one silicon atom or mixtures thereof or with Monosilanes is implemented. Process for the preparation of silicate-phosphate materials, characterized in that in the reaction products obtained according to claim 3 or 4, the solvent is removed and the reaction products are dried at temperatures below 40 ° C. A process for the preparation of silicate-phosphate materials, characterized in that the reaction products obtained according to claim 3,4 or 5 are calcined at temperatures of 40-400 ° C. A process for the preparation of silicate-phosphate materials, characterized in that the reaction product obtained according to claim 6 is heated to temperatures of 400 to 1000 ° C. Process for the preparation of silicate phosphate materials according to Claims 3 to 7, characterized in that active and / or passive fillers and / or molecular or polymeric additives are added to the starting materials. Use of the silicate phosphate materials (SiPOs) according to claim 1 and 2 as a component for optical and / or optoelectronic applications (transparent materials, glasses with special properties such as refractive index, density, transparency, chemical resistance), whereby certain functions by material intrinsic Properties or by the properties of fillers and / or molecular or polymeric additives (eg laser dyes or luminescent components). Use of the silicate phosphate materials (SiPOs) according to claim 1 and 2 as a component for flame retardants or protective layers (for plastics, textiles, wood products, paper, cardboard, plastering, insulating materials and building material composites). Use of the silicate-phosphate materials (SiPOs) according to claim 1 and 2 as a component for long-term fertilizer. Use of the silicate-phosphate materials (SiPOs) according to claim 1 and 2 as a matrix or encapsulation material for (sensitive) functional components such as biologically active molecules, active substances or nutrients. Use of the silicate phosphate materials (SiPOs) according to claim 1 and 2 as corrosion protection (component) z. B. for surface treatments. Use of the silicate-phosphate materials (SiPOs) according to claim 1 and 2 as a primer z. As for the coating of organic polymers or metallic materials or biomaterials with each other or with non-metallic-inorganic materials. Use of the silicate-phosphate materials (SiPOs) according to claim 1 and 2 for the production of materials or components in which electrical, electronic, acoustic or magnetic properties are made available. Use of the silicate-phosphate materials (SiPOs) according to claim 1 and 2 for the preparation of catalysts or catalyst components.

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