# US 2017/0285232 A1 · Dithiolene Metal Complex Colorless IR Absorbers

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- Number: US 2017/0285232 A1
- Document ID: US20170285232A1
- Status: Published application
- Kind: A1
- Application number: 15/623,699
- Filed: 2017-06-15
- Published: 2017-10-05
- Earliest claimed: 2007-01-17
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Urs Lehmann; Daniel Heizler
- Web page: https://patentgrep.com/patent/US20170285232A1

## CPC

- C07F 15/045: {without a metal-carbon linkage}
- B29B 13/024: {Hollow bodies, e.g. tubes or profiles}
- B29C 65/1677: {making use of an absorber or impact modifier}
- B29C 66/71: {characterised by the composition of the plastics material of the parts to be joined (welding bar compositions B29C65/125)}
- C07D 233/84: Sulfur atoms
- C07D 233/86: Oxygen and sulfur atoms, e.g. thiohydantoin
- C07D 233/88: Nitrogen atoms, e.g. allantoin
- C07D 239/22: with hetero atoms directly attached to ring carbon atoms
- C07F 11/00: Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F 15/0066: {without a metal-carbon linkage}
- C07F 15/0093: {without a metal-carbon linkage}
- G02B 5/208: {for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation}
- G02B 5/22: Absorbing filters {(G02B5/201 - G02B5/208 take precedence)}
- G02B 5/223: {containing organic substances, e.g. dyes, inks or pigments}
- B29C 35/0272: {using lost heating elements, i.e. heating means incorporated and remaining in the formed article (for preforms with internal stresses B29C61/0625; joining using lost heating elements B29C65/34; making electrically conductive articles B29C70/882)}
- B29C 65/00: Joining {or sealing} of preformed parts {, e.g. welding of plastics materials}; Apparatus therefor {(general aspects of processes or apparatus for joining preformed parts B29C66/00; using porous material formed by internal pressure generated therein for joining preformed parts B29C44/1228, B29C44/326)}
- B29C 65/1616: {Near infrared radiation [NIR], e.g. by YAG lasers}
- B29C 65/1674: {making use of laser diodes (B29C65/167 takes precedence)}
- B29C 66/7332: {at least one of the parts to be joined being coloured}
- B29C 66/73366: {both parts to be joined being transparent or translucent to visible light}
- B29C 66/73921: {characterised by the materials of both parts being thermoplastics}
- B29C 2035/0822: {using IR radiation}
- B29K 2023/12: {PP, i.e. polypropylene}
- B29K 2025/08: {Copolymers of styrene, e.g. AS or SAN, i.e. acrylonitrile styrene (B29K2055/02 takes precedence)}
- B29K 2027/16: {PVDF, i.e. polyvinylidene fluoride}
- B29K 2033/08: {Polymers of acrylic acid esters, e.g. PMA, i.e. polymethylacrylate}
- B29K 2033/12: {Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate}
- B29K 2055/02: ABS polymers, i.e. acrylonitrile-butadiene-styrene polymers
- B29K 2067/00: Use of polyesters {or derivatives thereof}, as moulding material
- B29K 2067/003: {PET, i.e. poylethylene terephthalate}
- B29K 2067/006: {PBT, i.e. polybutylene terephthalate}
- B29K 2069/00: Use of PC, i.e. polycarbonates {or derivatives thereof}, as moulding material
- B29K 2077/00: Use of {PA, i.e.} polyamides, e.g. polyesteramides {or derivatives thereof}, as moulding material
- B29K 2081/04: {Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof}
- B29K 2081/06: {PSU, i.e. polysulfones; PES, i.e. polyethersulfones or derivatives thereof}
- B29K 2105/0085: {Copolymers}
- B29K 2105/0088: {Blends of polymers}
- B29K 2995/0017: Heat stable
- B29K 2995/002: Coloured
- B29K 2995/0026: Transparent
- B29K 2995/0027: for light outside the visible spectrum
- B41M 3/14: Security printing {(securities B42D25/29)}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- 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
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)

## Abstract

The invention relates to the use of compounds of formulae (I) and/or (II) as colorless IR absorbers wherein M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, X1, X2 and X3 are each independently of the others sulfur or oxygen, R1, R2, R3, R4, R5 and R6 are each independently of the others hydrogen, NR7R8, unsubstituted or substituted C1-C18alkyl, C1-C18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C1-C18alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R2 and R8, each independently of the other, being unsubstituted or substituted C1-C18alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, a further IR absorber optionally being added to the compounds of formulae (I) and (II). The invention relates also to novel dithiolene compounds of formulae (I) and (II) wherein X1 is oxygen and X2 and X3 are oxygen or sulfur. The invention relates furthermore to novel dithiolene compounds of formulae (I) and (II) wherein R1 to R6 arc NR7R8.

## Claims

### Claim at position 1

-11. (canceled)

### Claim 12

A method of using colorless IR absorbers comprising
a) treating a material with a compound of formula I and/or II
wherein
M is Ni, Pd, Pt,
X1 is oxygen,
X2 and X3 are each independently of the other sulfur or oxygen,
R1, R2, R3, R4, R5 and R6 are each independently of the others hydrogen, NR7R8, unsubstituted or substituted C1-C18alkyl, C1-C18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C1-C18alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R7 and R8, each independently of the other, being unsubstituted or substituted C1-C18alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl,
wherein the material is a security print, an invisible and IR readable bar code, a laser-welded plastic, a dried print, a fixed toner on paper, a laser marked plastic, or a heated preform,
optionally a further IR absorber; and
b) using the treated material of a) for security printing, invisible and IR readable bar codes, laser-welding of plastics, drying of print, fixing of toners on paper, laser marking, and heating of plastics preforms.

### Claim 13 (depends on 12)

The method of claim 12, wherein for formulae I and II
R1, R2, R3, R4, R5 and R6 are NR7R8, wherein R7 and R8 are each independently of the other unsubstituted or substituted C1-C18alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl.

### Claim 14 (depends on 12)

The method according to claim 12, wherein R1, R2, R3, R4 are each independently of the others —N(C1-C6alkyl)2, unsubstituted C1-C8alkyl, —(CH2)n-[O—(CH2)m]k—OCH3 with n=2-6, m=2 or 3, k=1-6; vinyl or allyl, —(CH2)q-phenyl with q=1-6.

### Claim 15 (depends on 12)

The method of claim 12, wherein the compound of formulae I or II is selected from the group consisting of

### Claim 16 (depends on 12)

The method of claim 12, wherein the material is treated with a compound of formula I
wherein
M is Ni, Pd, or Pt,
X1 is oxygen,
X2 is sulfur or oxygen,
R1, R2, R3, and R4, are each independently of the others hydrogen, NR7R8, unsubstituted C1-C18alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted C1-C18alkenyl,
R7 and R8, each independently of the other, being unsubstituted C1-C18alkyl.

### Claim 17 (depends on 12)

The method of claim 12 wherein the material is treated with a compound of formula I
wherein
M is Ni, Pd, or Pt,
X1 and X2 are each independently of the other sulfur or oxygen,
R1, R2, R3, and R4, are NR7R8, wherein R7 and R8 are each independently of the other unsubstituted C1-C18alkyl.

### Claim 18 (depends on 17)

The method of claim 17, wherein R7 and R8 are each independently of the other unsubstituted C1-C6alkyl.

### Claim 19 (depends on 12)

The method according to claim 12, wherein step b) is using the treated material for laser-welding of plastics.

### Claim 20 (depends on 12)

The method according to claim 12, wherein step b) is using the treated material for security printing or producing invisible and IR readable bar codes.

### Claim 21 (depends on 1)

The method according to claim 1, wherein the further IR absorbers are polymethines.