EP4117813A1 - Zusatzstoff für photokatalytische farben mit aktivierung im sichtbaren spektrum - Google Patents

Zusatzstoff für photokatalytische farben mit aktivierung im sichtbaren spektrum

Info

Publication number
EP4117813A1
EP4117813A1 EP20722377.7A EP20722377A EP4117813A1 EP 4117813 A1 EP4117813 A1 EP 4117813A1 EP 20722377 A EP20722377 A EP 20722377A EP 4117813 A1 EP4117813 A1 EP 4117813A1
Authority
EP
European Patent Office
Prior art keywords
photo
catalytic material
water
acid
triazine
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.)
Pending
Application number
EP20722377.7A
Other languages
English (en)
French (fr)
Inventor
Pier Carlo Ricci
Stefania PORCU
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.)
Universita degli Studi di Cagliari
Original Assignee
Universita degli Studi di Cagliari
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 Universita degli Studi di Cagliari filed Critical Universita degli Studi di Cagliari
Publication of EP4117813A1 publication Critical patent/EP4117813A1/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/063—Titanium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/39—Photocatalytic properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0215—Coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/72—Treatment of water, waste water, or sewage by oxidation
    • C02F1/725—Treatment of water, waste water, or sewage by oxidation by catalytic oxidation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/30—Treatment of water, waste water, or sewage by irradiation
    • C02F1/32—Treatment of water, waste water, or sewage by irradiation with ultraviolet light
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/02—Specific form of oxidant
    • C02F2305/023—Reactive oxygen species, singlet oxygen, OH radical
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/10—Photocatalysts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings

Definitions

  • the present invention relates to compositions for making additives in the field of photo-catalytic paints.
  • the invention relates to compositions capable of extending also in the field of the visible spectrum the activation of the photo-catalytic reaction by the compositions of the invention.
  • the paints based on photo-catalysis currently present on the market are applied on the surface of the materials, and allow the reduction of pollutants present in the environment, so promoting the decomposition of organic and inorganic substances [which can be assimilated to all fine powders or Particulate Matter (PMio) present in the environment in the form of microscopic particles, the aerodynamic diameter of which is equal to or less than 10 pm], and of microbes.
  • PMio Particulate Matter
  • organic and inorganic substances can be mentioned: nitrogen oxides, poly-condensed aromatic substances, benzene, sulfur dioxide, carbon monoxide, formaldehyde, acetaldehyde, methanol, ethanol, benzene, ethyl-benzene, meta-xylene, nitrogen monoxide and dioxide.
  • UV ultraviolet
  • This wavelength is related to the gap between valence band and conduction band of titanium dioxide (material indispensable for the activation of these processes).
  • Flowever, such wavelength, necessary to make the process efficient, is harmful to the sensitivity of the human eye (UV). Therefore it is better that the process be naturally activated by the percentage of UV sunrays (equal to 5%, also as such wavelengths must be screened in the interior lighting). It follows that the paints currently on the market are not therefore suitable for use in interior spaces such as homes, offices, commercial premises and vehicles in general.
  • the first document shows in a comprehensive and detailed way the mechanisms of photo catalysis that are induced on the surface of TiC>2.
  • the second document further indicates the mechanisms that can be used just to extend the absorption and the operation of the photo-catalysis of T1O2 even with wavelengths smaller than the semiconductor band gap.
  • the charge transfer by means of a sensitizer is generally indicated.
  • patents relating to the same subject exist in the patent field.
  • patent document US20100087310A1 describes a sensitizer based on TiC>2 modified with heptazines.
  • the spectroscopic properties of the final product are not satisfactory, as this patent clearly shows in Figures 2 and 6 an absorption spectrum equal to zero for wavelengths greater than 450 nanometers, which however shows particularly low absorption levels, also between 400 and 450 nanometers.
  • the absorption is lower than 5% compared to the maximum peak which instead is present in a deep ultraviolet region. It follows that most of the visible spectrum, which reaches up to approximately 700 nanometers, remains excluded from the potential of the material defined by the patent.
  • EP2188125A1 describes obtaining of an organic/inorganic hybrid material.
  • it is suggested to extend the absorption of the product obtained in the visible field only by controlling the shape and the crystal structure of PO2.
  • the organic portion has the clear role of a "binder” and has no role in the photo-catalytic process, what is reflected in unsatisfactory application characteristics.
  • Figure 1 of the document in question shows that the reduction of NOx using sources with a low content of UV components (400 nanometers) does not exceed 10%.
  • the main disadvantage of the solution described in this document is that it only presents unchanged T1O2, and the composition is not technically capable of operating in the visible field in an efficient way; furthermore, features are not shown with which the samples were lighted with incandescent and fluorescent lamps.
  • patent documents US20100266470A1 and US8367579B2 only describe T1O2 which is placed or not on a very precise inorganic support. The operation of both patents is limited to the use with a very precise support and this represents a disadvantage in the applications of these inventions.
  • modified T1O2 relates to the photo-catalytic compound or hybrid material prepared according to the method of the present invention.
  • This hybrid material comprises an organic part and an inorganic part which interact with each other, making up a new material.
  • FIG. 1 Charge transfer mechanism between the organic part and T1O2;
  • Figure 2 Kubelka-Munk function of T1O2 in the anatase form (dashed lines), wherein the material is obtained following the instructions of patent US20100087310 (dashed and dot lines) and of the new modified T1O2 compound (continuous line);
  • the photo-catalytic material obtained by the process according to the invention is characterized by values of F(R ⁇ ) greater than or equal to 0.2 (F(R ⁇ ) > 0.2), which are measured with wavelength of 450nm and in any case not null for wavelengths between 400 and 600 nm.
  • the Kubelka - Munk function F(R) is defined as wherein k is the absorption coefficient and s the scattering factor, R ⁇ is the diffused reflectance. From this relationship it can be deduced that, by assuming that the scattering coefficient be constant, the Kubelka-Munk function F(R) is proportional to the absorption coefficient k.
  • the absorption has been determined by means of diffused reflectance measurements by using a photo-detector PbS in solid-state and using the KBr as white.
  • the instrument used for the measurements is a UV-Vis-NIR Agilent Technologies Cary 5000;
  • FIG. 4 Photo-catalytic test for the degradation of rhodamine by using a LED lamp as a light source: ( ⁇ ) T1O2 in anatase form, ( ⁇ ) Ti02 anatase obtained by following the instructions of US20100087310 patent, (D) T1O2 modified with the instructions given in the detailed description of the invention.
  • the present invention relates to the process of making a Ti02-based hybrid material, obtained from the combination of precursors for the synthesis of TiC>2 (Anatase) and 6-phenyl-2,4-diamino-1 ,3,5-triazine (organic part).
  • the material is made with the final powder form that can be formulated as a paint with a suitable binder for coating any surface.
  • the hybrid material comprises an organic base which, following an optical excitation in a range between 400 and 600 nanometers (range where T1O2 is unable to absorb the incident photon) has the purpose of absorbing part of the incident radiation and transfer it in a non radiating and efficient way to TiC>2.
  • Such charge transfer occurs by means of the excited levels of the two parts interacting in order to form the hybrid material according to the invention.
  • the T1O2 surface is modified following the formation process in presence of 6-phenyl-2,4-diamino-1 ,3,5-triazine with the presence of new excited levels. These levels can also absorb within the visible part of the electromagnetic spectrum (wavelength less than 600 nm) and efficiently transfer in the conduction band of T1O2 (see Figure 1).
  • the material according to the invention is capable of degrading carbonaceous elements with which it comes into contact, in the presence of light with wavelength between 300 and 600 nm.
  • a characteristic of the semiconducting metal oxides is the strong oxidizing power of their holes h+ h+ which can react with the water absorbed on their surface, as shown in reaction (4). This produces the formation of a highly reactive hydroxyl radical ⁇ OH ⁇ OH). Holes and hydroxyl radicals are both highly oxidizing and as such can be used to oxidize most organic contaminants.
  • reaction (5) it is shown how air oxygen acts as an electron acceptor for the formation of super-oxide ion.
  • Reaction 2 to 5 can occur even if the charge excess is transferred in an efficient way externally of T1O2, for example through the modification of the structure with the following processes which include derivatives of the 6- phenyl-2,4-diamino-1 ,3,5-triazine molecule.
  • the invention therefore consists in the realization of an organic/inorganic hybrid material obtained by the modification of T1O2 with specific treatments (see below) of organic materials based on 6-phenyl-2,4- diamino-1 ,3,5-triazine.
  • Such treatments allow that the hybrid material according to the invention causes the reactions 2 to 5 even as a result of a lighting with electromagnetic waves with wavelengths between 300 and 600 nanometers.
  • Figure 2 shows for comparison the Kubelka-Munk which is proportional to the absorption of the materials T1O2 (anatase), of the material obtained following the procedures described in patent US20100087310 (Example 4) and the hybrid compound (T1O2 modified) obtained through the treatments indicated below.
  • the absorption area also represents the spectral working area of the photo-catalytic material.
  • the ratio between the inorganic part and the organic component can be calculated through the X diffraction spectrum.
  • the X diffraction spectrum in Figure 3 shows 2Q diffraction peaks at 25°, 37°, 48° and 54° (common to the anatase phase of T1O2) and a peak 20 at 26° (typical of the product obtained).
  • the relationship between the peak area at 25° of anatase and the peak at 26° of the hybrid material must be comprised between 20:1 and 1 :1.
  • 6-phenyl-1 ,3, 5-triazine-2, 4-diamine (CAS Number 91-76-9) is solubilized in a solvent selected from: ethanol, diethyl ether, hydrogen chloride, trifluoroacetic acid, acetone, benzene, dimethylformaldehyde.
  • titanium tetrachloride and a reducing agent such as ascorbic acid or formic acid, oxalic acid, lithium aluminum hydride, sodium boron hydride, hydrazine, phosphorous acid
  • a reducing agent such as ascorbic acid or formic acid, oxalic acid, lithium aluminum hydride, sodium boron hydride, hydrazine, phosphorous acid
  • the ratio between the weight of TiCU and the reducing agent is between 8 and 15. Preferably, such ratio should be between 11 and 13.
  • the weight ratio between 6-phenyl-1 ,3, 5-triazine-2, 4-diamine and titanium tetrachloride is between 0.1 and 1 , preferably between 0.3 and 0.4.
  • the obtained solid is preferably washed with standard washings (first in water and then through ethanol or diethyl ether, hydrochloric acid, trifluoracetic acid, acetone, benzene, or dimetilformaldeyde); then it is subjected to a thermal treatment at temperatures between 350 and 500°C for a time between 60 and 240 minutes.
  • the compound thus obtained allows the degradation of pollutants not only with visible artificial light, but also with the daylight diffused in the rooms.
  • the compound can be used to degrade contaminants and pollutants in liquids or gases, in particular in water and in air.
  • the compound can advantageously be applied as a thin layer on various substrates, such as glass, wood, fibers, ceramics, cement, building materials, silicates, metals, paper and plastic. This allows application options in a variety of sectors, such as self-cleaning surfaces in construction, pottery and automotive industry, or in environmental engineering (air-conditioning equipment, equipment for air purification and sterilization, and in purification of water, in particular of drinking water, for example, for antibacterial and antiviral purposes).
  • the compound can be used in interior and exterior coatings, such as paints, plasters, paints and enamels for applications on walls, plaster surfaces, coatings, wallpapers and surfaces in wood, metal, glass or ceramic, or on components such as thermal insulation composites systems and curtain wall elements, as well as road and plastic coatings, plastic films, fibers and paper.
  • the photo-catalyst can also be used in the production of prefabricated concrete elements, concrete paving stones, tiles, ceramics, floors and coatings, wallpapers, fabrics, panels and coating elements for ceilings and walls in indoor and outdoor environments.
  • the compound can be used as such as a powder dispersed in water and can be formulated as a water and solvent paint, mixed with common components known to persons skilled in the art for these applications.
  • any kind of colloidal solutions, thickeners and glues can be used, as long as they do not absorb light in the visible range.
  • a preparation method can involve mixing the hybrid powder with a glue such as a colloidal solution (Cellulose Nitrate) in the ratio of 10 ml per 20 mg. The quantity ratio depends on the use and the final shape to give to the product. The greater the amount of hybrid is in comparison with the initial paint, the greater and quicker the photo-catalytic effect will be.
  • the following examples are illustrative of the invention and in no case they must be considered limitative of the relative scope.
  • the solution is then transferred inside of an autoclave of 30 ml and put in an oven at 180°C for about 8 hours. Once the system has reached the room temperature it is possible to filter the product and perform vacuum washings with water and ethanol in order to eliminate any impurities and the solid obtained is first dried at 60°C for about 12 hours and then calcined at 400°C (10°C/min) for 2 hours in order to obtain the modified T1O2 in its anatase form. With the preparation parameters a ratio of the inorganic part (T1O2) on the polymer part of 20:1 was obtained, defined by the area of the peaks of the XRD diffraction pattern.
  • An alumina substrate is half-covered by a modified T1O2 film (50 mg of a total surface area of 4 cm 2 ) according to the instructions in Example 1 , by depositing it by means of normal material glue (cellulose nitrate) and is placed inside a sealed chamber. Inside the chamber cigarette combustion fumes are introduced. The result is the blackening of the entire surface due to VOCS generated during combustion.
  • normal material glue cellulose nitrate
  • Table 1 Values of light flow measured on an alumina surface blackened with VOC, before and after the irradiation with LED light. Part of the surface itself had previously been coated with a modified T1O2 film obtained with the synthesis reported in Example 1.
  • 6-phenyl-1 ,3, 5-triazine-2, 4-diamine (CAS Number 91-76-9) is placed inside an oven and heated to a temperature between 350 and 500°C. Inside the same oven T1O2 is placed which is already amorphous or in an anatase phase for a time between 60 and 240 minutes.
  • the hybrid system obtained according to this procedure is not stable for photo-catalytic type measurements.
  • Example 2 2 grams of phenyl 1 , 3, 5-triazine-2, 4-diamine are placed in a tubular oven (diameter 2 cm, length 45 cm). Inside the same oven at a distance of 10 cm from the organic compound 50 mg of T1O2 in an anatase phase are placed. The oven is brought to a temperature of 400°C for 45 minutes. With such preparation parameters a ratio of the inorganic part (TiC>2) on the polymeric part of 20:1 was obtained.
  • TiC>2 in anatase phase is preheated, preferably at a temperature between 80 and 120°C.
  • Phenyl-1 ,3, 5-triazine-2, 4-diamine is dissolved in a solution of ethanol or alternatively of diethyl ether, hydrochloric acid, trifluoracetic acid, acetone, benzene, or dimetilformaldeyde and dripped on the preheated TiC>2.
  • the system is thermally treated with temperatures between 350 and 500°C for a time between 60 and 240 minutes.
  • the hybrid system obtained according to this procedure is not stable for photo-catalytic measurements.
  • 6-phenyl-1 ,3, 5-triazine-2, 4-diamine 300 mg are dispersed in 15 ml of ethanol and the system is left under stirring for 30 minutes.
  • 100 mg of T1O2 in anatase phase are placed on the preheated plate at 100°C for 15 minutes.
  • the initial solution of 6-phenyl-1 ,3,5-triazine-2,4- diamine is dripped onto T1O2 with a 1 ml pipette.
  • the obtained compound is then treated at 400°C for 60 minutes.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Catalysts (AREA)
EP20722377.7A 2020-03-12 2020-03-12 Zusatzstoff für photokatalytische farben mit aktivierung im sichtbaren spektrum Pending EP4117813A1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2020/052240 WO2021181136A1 (en) 2020-03-12 2020-03-12 Additive for photocatalytic paints with activation in visible spectrum

Publications (1)

Publication Number Publication Date
EP4117813A1 true EP4117813A1 (de) 2023-01-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP20722377.7A Pending EP4117813A1 (de) 2020-03-12 2020-03-12 Zusatzstoff für photokatalytische farben mit aktivierung im sichtbaren spektrum

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Country Link
EP (1) EP4117813A1 (de)
WO (1) WO2021181136A1 (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9358502B2 (en) * 2007-08-31 2016-06-07 Cristal Usa Inc. Photocatalytic coating
CN108033485A (zh) * 2017-11-17 2018-05-15 中山大学 一种一步法合成TiO2微球高效制氢和降解污染物的方法

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Publication number Publication date
WO2021181136A1 (en) 2021-09-16

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