US20100021833A1 - Dithiolene metal complex colorless ir absorbers - Google Patents
Dithiolene metal complex colorless ir absorbers Download PDFInfo
- Publication number
- US20100021833A1 US20100021833A1 US12/520,889 US52088907A US2010021833A1 US 20100021833 A1 US20100021833 A1 US 20100021833A1 US 52088907 A US52088907 A US 52088907A US 2010021833 A1 US2010021833 A1 US 2010021833A1
- Authority
- US
- United States
- Prior art keywords
- unsubstituted
- substituted
- laser
- absorbers
- colorless
- 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.)
- Abandoned
Links
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 35
- 150000004696 coordination complex Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 12
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 12
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 239000011593 sulfur Substances 0.000 claims abstract description 10
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 9
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- 229910052737 gold Inorganic materials 0.000 claims abstract description 7
- 229910052738 indium Inorganic materials 0.000 claims abstract description 7
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 7
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 7
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 7
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 238000007639 printing Methods 0.000 claims description 20
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- 238000000034 method Methods 0.000 claims description 18
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- 239000000463 material Substances 0.000 claims description 13
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- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000010330 laser marking Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims 8
- 238000002835 absorbance Methods 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- -1 2-ethylhexyl Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000003466 welding Methods 0.000 description 6
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 239000013078 crystal Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- GGVMPKQSTZIOIU-UHFFFAOYSA-N quaterrylene Chemical group C12=C3C4=CC=C2C(C2=C56)=CC=C5C(C=57)=CC=CC7=CC=CC=5C6=CC=C2C1=CC=C3C1=CC=CC2=CC=CC4=C21 GGVMPKQSTZIOIU-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B13/00—Conditioning or physical treatment of the material to be shaped
- B29B13/02—Conditioning or physical treatment of the material to be shaped by heating
- B29B13/023—Half-products, e.g. films, plates
- B29B13/024—Hollow bodies, e.g. tubes or profiles
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- 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).
- the invention accordingly relates to the use of compounds of formula I and/or II as colorless IR absorbers
- M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti,
- X 1 , X 2 and X 3 are each independently of the others sulfur or oxygen
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently of the others hydrogen
- NR 7 R 8 unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 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 C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, a further IR absorber optionally being added to the compounds
- substituents R 1 to R 6 or R 1 to R 4 are C 1 -C 18 alkyl radicals they are preferably unsubstituted C 1 -C 18 alkyl radicals, more preferably C 1 -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 R 1 to R 6 or R 1 to R 4 are C 1 -C 18 alkenyl radicals they are preferably unsubstituted C 1 -C 18 alkenyl radicals, more preferably C 1 -C 6 alkenyl radicals. Examples may be vinyl or allyl.
- substituents R 1 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 C 1 -C 6 alkyl radicals.
- M is Ni, Pd, Pt,
- X 1 , X 2 and X 3 are each independently of the others sulfur or oxygen
- 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 compounds of formulae I and II are used in security printing and printing of bar codes. (claim 7 )
- the IR absorbers of formulae I and II can 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.
- plastics components are welded to one another.
- 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), styren
- Especially advantageous in welding is the use of two identically transparent plastics workpieces, for example colorless-transparent/colorless-transparent or colored-trans-parent/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 II wherein
- M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti,
- X 1 is oxygen and X 2 and X 3 are oxygen or sulfur
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 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 C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl.
- the invention relates also to novel dithiolene compounds of formulae I and II wherein
- M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti,
- X 1 , X 2 and X 3 are each independently of the others sulfur or oxygen
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are NR 7 R 8 , wherein R 7 and R 8 are each independently of the other unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl. (claim 10 ).
- —NR 7 R 8 is —N(C 1 -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 II are suitable for use as optical filters for plasma display panels (PDPs).
- PDPs plasma display panels
- the compound is known from J. Chem. Soc., Dalton Trans 1998, 3731-3736, and its preparation is described therein.
- 1,3-Diisopropyl-4,5-dioxo-imidazoline-2-thione is reacted under reflux conditions with metallic nickel and Lawesson's reagent
- 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 110° 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 2 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 9 990 nm 10 1020 nm 11 996 nm 12 999 nm 13 1009 nm 14 991 nm 15 1002 nm 16 1007 nm 17 1006 nm 18 1003 nm 19 1011 nm 20 1007 nm 21 1003 nm 22 1005 nm 23 1002 nm 24 903 nm
- 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.
- the IR absorber from Example 1 is incorporated into a polycarbonate disc having a thickness of 2 mm (concentration: 100 ppm).
- 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 A3 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.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Thermal Sciences (AREA)
- Electromagnetism (AREA)
- Printing Methods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Optical Filters (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Laser Beam Processing (AREA)
Applications Claiming Priority (3)
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EP07100657.1 | 2007-01-17 | ||
EP07100657 | 2007-01-17 | ||
PCT/EP2007/064102 WO2008086931A1 (en) | 2007-01-17 | 2007-12-18 | Dithiolene metal complex colorless ir absorbers |
Related Parent Applications (1)
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PCT/EP2007/064102 A-371-Of-International WO2008086931A1 (en) | 2007-01-17 | 2007-12-18 | Dithiolene metal complex colorless ir absorbers |
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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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US15/255,418 Active US9738611B2 (en) | 2007-01-17 | 2016-09-02 | Dithiolene metal complex colorless IR absorbers |
US15/623,699 Active US9920087B2 (en) | 2007-01-17 | 2017-06-15 | Dithiolene metal complex colorless IR absorbers |
US15/837,371 Active US10112964B2 (en) | 2007-01-17 | 2017-12-11 | Dithiolene metal complex colorless IR absorbers |
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US15/623,699 Active US9920087B2 (en) | 2007-01-17 | 2017-06-15 | Dithiolene metal complex colorless IR absorbers |
US15/837,371 Active US10112964B2 (en) | 2007-01-17 | 2017-12-11 | Dithiolene metal complex colorless IR absorbers |
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US (4) | US20100021833A1 (zh) |
EP (1) | EP2101986B1 (zh) |
JP (4) | JP2010516823A (zh) |
CN (1) | CN101610893B (zh) |
WO (1) | WO2008086931A1 (zh) |
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US9267042B2 (en) | 2008-10-27 | 2016-02-23 | Datalase Ltd. | Coating composition for marking substrates |
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2007
- 2007-12-18 JP JP2009545845A patent/JP2010516823A/ja active Pending
- 2007-12-18 EP EP07857732.7A patent/EP2101986B1/en active Active
- 2007-12-18 WO PCT/EP2007/064102 patent/WO2008086931A1/en active Application Filing
- 2007-12-18 US US12/520,889 patent/US20100021833A1/en not_active Abandoned
- 2007-12-18 CN CN200780047902.9A patent/CN101610893B/zh active Active
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2013
- 2013-06-17 JP JP2013126953A patent/JP5733804B2/ja not_active Expired - Fee Related
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2014
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- 2017-06-15 US US15/623,699 patent/US9920087B2/en active Active
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US9333786B2 (en) | 2007-07-18 | 2016-05-10 | Datalase, Ltd. | Laser-sensitive coating formulations |
US20120129090A1 (en) * | 2008-10-23 | 2012-05-24 | Basf Se | Heat absorbing additives |
US8853314B2 (en) * | 2008-10-23 | 2014-10-07 | Datalase Ltd. | Heat absorbing additives |
US9267042B2 (en) | 2008-10-27 | 2016-02-23 | Datalase Ltd. | Coating composition for marking substrates |
US9260614B2 (en) | 2010-11-24 | 2016-02-16 | Basf Se | Use of aryl or heteroaryl substituted dithiolene metal complexes as IR absorbers |
US9388206B2 (en) | 2011-05-06 | 2016-07-12 | Basf Se | Chromophores with perfluoroalkyl substituents |
US20160018576A1 (en) * | 2013-04-10 | 2016-01-21 | Asahi Glass Company, Limited | Infrared cut filter, solid-state imaging device, and imaging/display apparatus |
US10345498B2 (en) * | 2013-04-10 | 2019-07-09 | AGC Inc. | Infrared cut filter, solid-state imaging device, and imaging/display apparatus |
US20180354191A1 (en) * | 2015-07-23 | 2018-12-13 | Hewlett-Packard Development Company, L.P. | Three-dimensional (3d) printing method |
Also Published As
Publication number | Publication date |
---|---|
EP2101986A1 (en) | 2009-09-23 |
JP2015057492A (ja) | 2015-03-26 |
US20170285232A1 (en) | 2017-10-05 |
CN101610893A (zh) | 2009-12-23 |
EP2101986B1 (en) | 2017-03-22 |
US20180099988A1 (en) | 2018-04-12 |
JP2017078173A (ja) | 2017-04-27 |
US9738611B2 (en) | 2017-08-22 |
CN101610893B (zh) | 2015-02-11 |
JP5733804B2 (ja) | 2015-06-10 |
US9920087B2 (en) | 2018-03-20 |
JP6526615B2 (ja) | 2019-06-05 |
JP2013216674A (ja) | 2013-10-24 |
JP6358930B2 (ja) | 2018-07-18 |
US10112964B2 (en) | 2018-10-30 |
US20160368940A1 (en) | 2016-12-22 |
JP2010516823A (ja) | 2010-05-20 |
WO2008086931A1 (en) | 2008-07-24 |
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