Dibenzoflourenone based chromophores

• US 7,038,066 B2
• Filed: 08/10/2001
• Issued: 05/02/2006
• Est. Priority Date: 05/25/1999
• Status: Expired due to Fees

• Current Assignee: Silverbrook Research Pty Limited
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Silverbrook, Kia
• Primary Examiner(s): POWERS, FIONA
• Application Number:
  US09/927,685
• Publication Number:
  US 20020088064A1
• Time in Patent Office: 1,726 Days
• Field of Search: 549/381, 549/382, 106/31.58
• US Class Current: 549/381
• CPC Class Codes: B41J 2/17513 Inner structure
• CPC Class Codes: B41J 2/17523 Ink connection
• CPC Class Codes: B41J 2/17546 electronically
• CPC Class Codes: B41J 3/51 the printed and recorded information being identical; using type elements with code-generating means
• CPC Class Codes: C09B 5/00 Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks
• CPC Class Codes: G06F 3/0321 by optically sensing the absolute position with respect to a regularly patterned surface forming a passive digitiser, e.g. pen optically detecting position indicative tags printed on a paper sheet constructional details of pen-shaped pointing devices G06F3/03545, G06F3/03542, G06F3/037
• CPC Class Codes: G06F 3/03542 Light pens for emitting or receiving light
• CPC Class Codes: G06F 3/03545 Pens or stylus
• CPC Class Codes: G06V 30/10 Character recognition
• CPC Class Codes: G06V 30/1444 Selective acquisition, locating or processing of specific regions, e.g. highlighted text, fiducial marks or predetermined fields
• CPC Class Codes: H04N 1/00358 Type of the scanned marks
• CPC Class Codes: H04N 1/00376 Means for identifying a mark sheet or area
• CPC Class Codes: H04N 1/32101 Display, printing, storage or transmission of additional information, e.g. ID code, date and time or title
• CPC Class Codes: H04N 1/32128 attached to the image data, e.g. file header, transmitted message header, information on the same page or in the same computer file as the image for information embedded in the image H04N1/32144
• CPC Class Codes: H04N 1/32133 on the same paper sheet, e.g. a facsimile page header
• CPC Class Codes: H04N 1/32144 embedded in the image data, i.e. enclosed or integrated in the image, e.g. watermark, super-imposed logo or stamp
• CPC Class Codes: H04N 1/32771 in response to a request, e.g. for a particular document
• CPC Class Codes: H04N 1/32778 : using a mark-sheet or machine-readable code request
• CPC Class Codes: H04N 2201/3205 : of identification information, e.g. name or ID code H04N2201/3209 takes precedence
• CPC Class Codes: H04N 2201/3207 : of an address
• CPC Class Codes: H04N 2201/3226 : of identification information or the like, e.g. ID code, index, title, part of an image, reduced-size image
• CPC Class Codes: H04N 2201/3242 : of processing required or performed, e.g. for reproduction or before recording H04N2201/3256 and subgroups take precedence
• CPC Class Codes: H04N 2201/3269 : of machine readable codes or marks, e.g. bar codes or glyphs
• CPC Class Codes: H04N 2201/327 : which are undetectable to the naked eye, e.g. embedded codes
• CPC Class Codes: H04N 2201/3271 : Printing or stamping
• CPC Class Codes: H04N 2201/3278 : Transmission

Abstract

An infrared dye, characterized in that the dye comprises a compound that can be described by molecule 1.

Claims

1. An infrared dye wherein the dye comprises of a molecule 1

wherein m and n are the number of fused 6-membered aromatic rings connected to each side of the central moiety such that the first 6-membered aromatic ring, if present, is connected as shown in 1;

and

wherein Q₁ and Q₂ are one of the same or different fused rings shown as 2 whereby one ring shown as 2 is connected at any of the two adjoining positions C₁ to C₄ at any orientation and another ring shown as 2 is connected to any of the two adjoining positions C₅ to C₈ at any orientation of the outer aromatic rings shown in 1 which may also include one or many substituents individually selected from the group consisting of R₁, a fused 5-membered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R₂, and fused polyaromatic rings optionally substituted with one or more substituents selected from R₃ wherein R₁, R₂ and R₃ are individually selected from the group R; and

wherein X₁ and X₂ are individually selected from the group consisting of CO and O; and

wherein Y is individually selected from the group consisting of CO and O; and

wherein Z is individually selected from the group consisting of CO and O; and

Q₃ is 0, 1 or more than 1 substituents that are individually selected from the group consisting of R₁₂, a fused 5-membered ring or a 6-membered aromatic ring optionally substituted with 1 to 4 substituents individually selected from R₁₃, and fused polyaromatic rings optionally substituted with one or more substituents selected from R₁₄ wherein R₁₂, R₁₃ and R₁₄ are individually selected from the group R; and

R is the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halide atom, a hydroxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group;

wherein the infrared dye absorbs strongly in the near infrared region of the spectrum but poorly in the visible region of the spectrum.

2. An infrared dye composition comprising a compound that can be described by molecule 1 according to claim 1.

3. A solvent-based ink composition comprising a compound that can be described by molecule 1 according to claim 1.

4. An infrared absorbing compound according to claim 1 wherein one or more polar group substituents such as —

SO₃H, —

NH₂ and —

CN are utilized.

5. A solvent-based ink according to claim 3 which is ink jet printer ink.