WO2008086931A1 - Dithiolene metal complex colorless ir absorbers - Google Patents

Dithiolene metal complex colorless ir absorbers Download PDF

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Publication number
WO2008086931A1
WO2008086931A1 PCT/EP2007/064102 EP2007064102W WO2008086931A1 WO 2008086931 A1 WO2008086931 A1 WO 2008086931A1 EP 2007064102 W EP2007064102 W EP 2007064102W WO 2008086931 A1 WO2008086931 A1 WO 2008086931A1
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WIPO (PCT)
Prior art keywords
unsubstituted
substituted
compounds
independently
alkyl
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.)
Ceased
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PCT/EP2007/064102
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English (en)
French (fr)
Inventor
Urs Lehmann
Daniel Heizler
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.)
BASF Schweiz AG
Original Assignee
Ciba Holding AG
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 Ciba Holding AG filed Critical Ciba Holding AG
Priority to EP07857732.7A priority Critical patent/EP2101986B1/en
Priority to US12/520,889 priority patent/US20100021833A1/en
Priority to JP2009545845A priority patent/JP2010516823A/ja
Priority to CN200780047902.9A priority patent/CN101610893B/zh
Publication of WO2008086931A1 publication Critical patent/WO2008086931A1/en
Anticipated expiration legal-status Critical
Priority to US15/255,418 priority patent/US9738611B2/en
Priority to US15/623,699 priority patent/US9920087B2/en
Priority to US15/837,371 priority patent/US10112964B2/en
Ceased legal-status Critical Current

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    • B29K2055/00—Use of specific polymers obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of main groups B29K2023/00 - B29K2049/00, e.g. having a vinyl group, as moulding material
    • B29K2055/02—ABS polymers, i.e. acrylonitrile-butadiene-styrene polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/003—PET, i.e. poylethylene terephthalate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/006—PBT, i.e. polybutylene terephthalate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2069/00—Use of PC, i.e. polycarbonates or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2077/00—Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
    • B29K2081/04—Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
    • B29K2081/06—PSU, i.e. polysulfones; PES, i.e. polyethersulfones or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0085—Copolymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0088—Blends of polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0012—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular thermal properties
    • B29K2995/0017—Heat stable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0018—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular optical properties, e.g. fluorescent or phosphorescent
    • B29K2995/002—Coloured
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0018—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular optical properties, e.g. fluorescent or phosphorescent
    • B29K2995/0026—Transparent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0018—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular optical properties, e.g. fluorescent or phosphorescent
    • B29K2995/0026—Transparent
    • B29K2995/0027—Transparent for light outside the visible spectrum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
    • B41M3/14—Security printing

Definitions

  • the invention relates to the use of specific dithiolene metal complexes as colorless IR absorbers.
  • the invention relates also to novel dithiolene metal complexes.
  • IR absorbers meet a significant technical need in a wide range of applications, such as security printing (bank notes, credit cards, identity cards, passports etc.), invisible and IR readable bar codes, the laser-welding of plastics, the curing of surface-coatings using IR radiators, the drying and curing of print, the fixing of toners on paper, optical filters for PDPs (plasma display panels), laser marking, the heating of plastics preforms etc.
  • IR absorbers such as, for example, quinone-diimmonium or aminium salts, polymethines (e.g. cyanines, squaraines, croconaines), phthalocyanines and naphthalocyanines, dithiolene and other metal complexes.
  • polymethines e.g. cyanines, squaraines, croconaines
  • phthalocyanines and naphthalocyanines e.g. cyanines, squaraines, croconaines
  • phthalocyanines and naphthalocyanines naphthalocyanines
  • dithiolene and other metal complexes e.g., dithiolene and other metal complexes.
  • Newer structures such as, for example, quaterrylene diimides, have also recently become known.
  • inorganic substances such as, for example, lanthanum hexaboride, indium tin oxide (ITO), antimony tin oxide (ATO) in nano- particulate form and coated mica materials ("Lazerflair” from Merck).
  • IR absorbers for example for security printing, are available, for example, from “American Dye Source”, but virtually all of them have an absorption in the VIS range of the spectrum (from 400 to 700 nm).
  • substituents Ri to R 6 or R 1 to R 4 are Ci-Ci 8 alkyl radicals they are preferably unsubstituted Ci-Ci 8 alkyl radicals, more preferably Ci-C 8 alkyl radicals, including straight- chain and branched and also cyclic alkyl radicals.
  • the following may be mentioned as examples: propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, 2-ethylhexyl, n-octyl, cyclopentyl, cyclohexyl.
  • substituents Ri to R 6 or R 1 to R 4 are CrCi 8 alkenyl radicals they are preferably unsubstituted CrCi 8 alkenyl radicals, more preferably CrC 6 alkenyl radicals. Examples may be vinyl or allyl.
  • substituents Ri to R 6 or R 1 to R 4 are aryl groups, they are preferably unsubstituted aryl groups, for example, phenyl, naphthyl, anthryl or phenanthryl groups.
  • substituents R 1 to R 6 or R 1 to R 4 are heteroarylalkyl radicals they are preferably unsubstituted heteroarylalkyl radicals which denotes that a heteroaromatic ring is bonded directly to an alkyl group.
  • the heteroaromatic ring is, for example, imidazolyl, pyridyl, thienyl, furyl, thiazolyl, indolyl, quinolinyl, pyrazolyl, pyrazyl, pyridazyl or pyrimidinyl.
  • the substituents R 7 and R 8 are preferably CrC 6 alkyl radicals.
  • Xi, X 2 and X 3 are each independently of the others sulfur or oxygen,
  • Ri, R2, R3, R 4 are each independently of the others -N(CrC 6 alkyl) 2 , unsubstituted
  • Colorless IR absorbers can be used in all fields of application that depend on the IR absorber's remaining invisible. The following uses may be mentioned by way of example: security printing (bank notes, credit cards, identity cards, passports etc.), invisible and IR readable bar codes, the laser-welding of plastics, the curing of surface-coatings using IR radiators, the drying and curing of print, the fixing of toners on paper, laser marking (plastics materials, paper, wood etc.) and the heating of plastics preforms. (Claim 5)
  • the IR absorbers of formulae I and Il can also be in the form of mixtures with further known IR absorbers, especially mixtures with polymethines (cyanines, squaraines and croconaines). Such IR absorber mixtures are suitable especially for security printing, (claim 8)
  • the IR absorbers are used in a concentration of from 10 ppm to 10 %, preferably 100 ppm to 2 % depending on the chosen application.
  • the laser welding is preferably carried out using an ND:YAG laser at 1064 nm or using a diode laser at 980 nm or 940 nm, and the concentration of IR absorber is, for example, from 5 to 500 ppm, preferably from 10 to 100 ppm.
  • the dithiolenes according to the invention are suitable especially for welding transparent plastics materials, such as polypropylene, polyvinylbutyral, polyamide, polycarbonate, polycarbonate-polyethylene terephthalate blends, polycarbonate-polybutylene terephthalate blends, polycarbonate- acrylonitrile-styrene-acrylonitrile copolymer blends, polycarbonate-acrylonitrile-butadiene- styrene copolymer blends, polymethyl methacrylate-acrylonitrile-butadiene-styrene co- polymer blends (MABS), polyethylene terephthalate, polybutylene terephthalate, polymethyl methacrylate, polybutyl acrylate, polymethyl methacrylate-polyvinylidene difluoride blends, acrylonitrile-butadiene-styrene copolymers (ABS), st
  • Especially advantageous in welding is the use of two identically transparent plastics workpieces, for example colorless-transparent/colorless-transparent or colored-transparent/colored-transparent.
  • IR absorber is added to the printing ink.
  • Suitable printing inks are water-based, oil-based or solvent-based printing inks, based on pigment or dye, for inkjet printing, flexographic printing, screen printing, intaglio printing, offset printing, laser printing or letterpress printing and for use in electrophotography.
  • the invention relates also to novel dithiolene compounds of formulae I and Il wherein M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, Xi is oxygen and X 2 and X3 are oxygen or sulfur,
  • Ri, R2, R3, R 4 , R5 and R 6 are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted CrCi 8 alkyl, Ci-Ci 8 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted Ci-Ci 8 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7 and R 8 , each independently of the other, being unsubstituted or substituted Ci-Ci 8 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl. (Claim 9)
  • the invention relates also to novel dithiolene compounds of formulae I and Il wherein M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, Xi, X 2 and X3 are each independently of the others sulfur or oxygen, Ri, R2, R3, R 4 , R5 and R 6 are NR 7 R 8 , wherein R 7 and R 8 are each independently of the other unsubstituted or substituted Ci-Ci 8 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl. (claim 10).
  • -NR 7 R 8 is -N(Ci-C 6 alkyl) 2
  • novel dithiolene compounds like the known dithiolene compounds, are suitable for use in security printing (bank notes, credit cards, identity cards, passports etc.), invisible and IR readable barcodes, the laser-welding of plastics, the curing of surface-coatings using IR radiators, the curing and drying of print, the fixing of toners on paper, laser marking (plastics, paper, wood etc.) and the heating of plastics preforms etc.
  • novel dithiolene compounds of formulae I and Il are suitable for use as optical filters for plasma display panels (PDPs).
  • PDPs plasma display panels
  • 0.333 part of platinum dichloride is added to a solution of 0.541 part of the product from example 3a and 1.085 parts of Lawesson's reagent in 50 parts of toluene.
  • the reaction mixture is maintained at 1 10 0 C for 90 minutes and filtered while hot, and 500 parts of n- hexane are added to the filtrate after cooling.
  • the resulting precipitate is filtered off and dried, yielding 0.5 part of product (absorption maximum 994 nm).
  • Example 6a The compound from Example 2 is oxidised with atmospheric oxygen in dichloromethane at reflux temperature to form the corresponding oxo compound. Its absorption maximum is found at 968 nm.
  • Example 6a Preparation of
  • Example A1 (Security printing) 1 1.9 parts of vinyl chloride, 2.1 parts of vinyl acetate, 10 parts of ethoxypropanol, 75.5 parts of methyl ethyl ketone and 0.5 part of the product from Example 1 are shaken together with 150 g of glass beads for 30 minutes in a Skandex mixer.
  • the resulting printing ink is applied to contrast paper using a doctor blade (film thickness when damp: 6 ⁇ m).
  • the print is visually colorless, but is clearly visible in the IR range using an IR-viewing device (cut-off filter 715 nm).
  • the fastness to light is excellent.
  • Example A1 By proceeding as indicated in Example A1 but using the IR absorber from Example 2, there accordingly is likewise obtained a colorless print having excellent fastness to light, which is clearly visible in the infrared range using an IR-viewing device.
  • Example A3 (Laser-welding of plastics material) Using an injection-moulding machine, the IR absorber from Example 1 is incorporated into a polycarbonate disc having a thickness of 2 mm (concentration: 100 ppm). Using an Nd:YAG laser, the resulting, virtually colorless disc is welded at a power of 30 watt and a rate of advance of 20 mm/s to a second 1 mm-thick pure polycarbonate disc not containing IR absorber. The resulting weld is characterised by an excellent bond, unchanged transparency, no melt irruptions and no bubbling. Under heavy mechanical loading, breakage of the discs does not occur at the welded seam.
  • Example A4 (Laser-welding of plastics material) By proceeding as indicated in Example A3 but using the IR absorber from Example 2, a virtually colorless polycarbonate disc is likewise obtained which has excellent welding properties. The resulting weld has unchanged transparency, the welding leaves no melt irruptions or bubbling and the strength of the weld is excellent. Examples A5 and A6

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Toxicology (AREA)
  • Health & Medical Sciences (AREA)
  • Electromagnetism (AREA)
  • Thermal Sciences (AREA)
  • Printing Methods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Optical Filters (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)
  • Laser Beam Processing (AREA)
PCT/EP2007/064102 2007-01-17 2007-12-18 Dithiolene metal complex colorless ir absorbers Ceased WO2008086931A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP07857732.7A EP2101986B1 (en) 2007-01-17 2007-12-18 Dithiolene metal complex colorless ir absorbers
US12/520,889 US20100021833A1 (en) 2007-01-17 2007-12-18 Dithiolene metal complex colorless ir absorbers
JP2009545845A JP2010516823A (ja) 2007-01-17 2007-12-18 ジチオレン金属錯体の無色ｉｒ吸収剤
CN200780047902.9A CN101610893B (zh) 2007-01-17 2007-12-18 二硫醇烯金属配合物无色ir吸收剂
US15/255,418 US9738611B2 (en) 2007-01-17 2016-09-02 Dithiolene metal complex colorless IR absorbers
US15/623,699 US9920087B2 (en) 2007-01-17 2017-06-15 Dithiolene metal complex colorless IR absorbers
US15/837,371 US10112964B2 (en) 2007-01-17 2017-12-11 Dithiolene metal complex colorless IR absorbers

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EP07100657 2007-01-17

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US15/255,418 Continuation US9738611B2 (en) 2007-01-17 2016-09-02 Dithiolene metal complex colorless IR absorbers
US15/255,418 Division US9738611B2 (en) 2007-01-17 2016-09-02 Dithiolene metal complex colorless IR absorbers

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WO2012152584A1 (en) 2011-05-06 2012-11-15 Basf Se Chromophores with perfluoroalkyl substituents
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RU2575644C2 (ru) * 2010-11-24 2016-02-20 Басф Се Применение арил-или гетероарил-замещенных дитиоленовых металлокомплексов в качестве ик-поглотителей
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WO2020079154A1 (en) 2018-10-18 2020-04-23 Basf Se Microparticle composition comprising an organic ir absorbing pigment
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RU2765644C1 (ru) * 2020-08-19 2022-02-01 Акционерное общество "Гознак" (АО "Гознак") Способ получения пигмента на основе замещенных дитиоленовых комплектов никеля

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