Water-based dithiolene infrared inkjet inks

• US 7,204,941 B2
• Filed: 04/02/2004
• Issued: 04/17/2007
• Est. Priority Date: 04/07/2003
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Papadakis, Alexandra Artemis, Ridley, Damon Donald, Starling, Scott Matthew, Vonwiller, Simone Charlotte, Silverbrook, Kia, Lapstun, Paul
• Primary Examiner(s): Gulakowski, Randy
• Assistant Examiner(s): Kugel, Timothy J.
• Application Number:
  US10/815,625
• Publication Number:
  US 20040196344A1
• Time in Patent Office: 1,110 Days
• Field of Search: 252/587
• US Class Current: 252/587
• CPC Class Codes: G06F 3/014 Hand-worn input/output arrangements, e.g. data gloves
• 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: G06K 7/10554 Moving beam scanning
• CPC Class Codes: G06K 7/10623 Constructional details
• CPC Class Codes: G06K 7/10693 for omnidirectional scanning
• CPC Class Codes: G06K 7/10722 Photodetector array or CCD scanning
• CPC Class Codes: G06K 7/10772 Moved readers, e.g. pen, wand
• CPC Class Codes: G06Q 10/00 Administration; Management
• CPC Class Codes: G06Q 10/087 Inventory or stock management, e.g. order filling, procurement or balancing against orders
• CPC Class Codes: G06Q 20/20 Point-of-sale [POS] network systems
• CPC Class Codes: G06Q 30/02 Marketing; Price estimation or determination; Fundraising
• CPC Class Codes: G06Q 30/0207 Discounts or incentives, e.g. coupons or rebates
• CPC Class Codes: G06Q 30/0212 Chance discounts or incentives
• CPC Class Codes: G06Q 30/0217 involving input on products or services in exchange for incentives or rewards
• CPC Class Codes: G06Q 30/0236 Incentive or reward received by requiring registration or ID from user
• CPC Class Codes: G06Q 30/0259 based on store location
• CPC Class Codes: G06Q 30/0267 Wireless devices
• CPC Class Codes: G06Q 30/0601 Electronic shopping [e-shopping]
• CPC Class Codes: H04N 25/59 by controlling the amount of charge storable in the pixel, e.g. modification of the charge conversion ratio of the floating node capacitance
• CPC Class Codes: H04N 25/671 for non-uniformity detection or correction
• CPC Class Codes: H04N 25/745 : Circuitry for generating timing or clock signals
• CPC Class Codes: H04N 25/75 : Circuitry for providing, modifying or processing image signals from the pixel array
• CPC Class Codes: H04N 25/767 : Horizontal readout lines, multiplexers or registers
• CPC Class Codes: H04N 25/778 : comprising amplifiers shared between a plurality of pixels, i.e. at least one part of the amplifier must be on the sensor array itself
• CPC Class Codes: H04N 3/1568 : for disturbance correction or prevention within the image-sensor, e.g. biasing, blooming, smearing correction circuits H04N25/62
• CPC Class Codes: H04N 5/33 : Transforming infrared radiation cameras or camera modules for generating image signals from infrared radiation H04N23/20; circuitry of SSIS for transforming infrared radiation into image signals H04N25/20

Abstract

The present invention provides an IR-absorbing dye suitable for formulating a water-based inkjet ink, said dye being of formula (I):

wherein:

• M is selected from Ni, Pd or Pt;
• R¹⁰ and R¹¹ are independently selected from C_1-30 hydrocarbyl, or R¹⁰ and R¹¹ together are joined to form a C_2-30 hydrocarbylene group;
• R¹² and R¹³ are independently selected from C_1-30 hydrocarbyl, or R¹² and R¹³ together are joined to form a C_2-30 hydrocarbylene group;
• wherein at least one of R¹⁰, R¹¹, R¹² or R¹³ comprises a hydrophilic group.

Dyes of this type are especially suitable for use in NETPAGE and Hyperlabel systems.

Claims

1. An IR-absorbing dye suitable for formulating a water-based inkjet ink, said dye being of formula (I):

2. A substrate having a dye according to claim 1 disposed thereon.

3. The substrate of claim 2, wherein said dye is disposed in the form of coded data.

4. The substrate of claim 3 comprising an interface surface and wherein the coded data is disposed over a substantial portion of said interface surface.

5. The substrate of claim 4, which is a paper sheet, a label, a tag, a packaging material or a product item.

6. The dye of claim 1, wherein at least one of R¹⁰, R¹¹, R¹² or R¹³ comprises a moiety suitable for reducing intermolecular interactions.

7. The dye of claim 6, wherein said moiety suitable for reducing intermolecular interactions is a bridged cyclic group.

8. The dye of claim 7, wherein R¹⁰ and R¹¹ together are joined to form a bridged cyclic group.

9. The dye of claim 7, wherein R¹² and R¹³ together are joined to form a bridged cyclic group.

10. The dye of claim 6, wherein said moiety suitable for reducing intermolecular interactions is a polymer.

11. An IR-absorbing dye according to claim 1, said dye being of formula (II):

12. The dye of claim 11, wherein j is 1 and k is 2.

13. The dye of claim 12 comprising a —

C(C_1-4 alkyl)₂—

bridging group.

14. The dye of claim 11, wherein M is Ni.

15. The dye of claim 11, wherein n is 1.

16. The dye of claim 11, wherein W is a substituent comprising a group of formula —

CO₂Z, —

SO₃Z, —

OSO₃Z, —

PO₃Z₂ or —

OPO₃Z₂, wherein Z is H or a water-soluble cation.

17. The dye of claim 11, wherein W is of formula —

(CH₂)_t—

SO₃Z, wherein t is 0 or an integer from 1 to 6, and Z is H or a water-soluble cation.

18. The dye of claim 11, wherein W is of formula —

CH₂SO₃H, —

CH₂SO₃Na or —

CH₂SO₃K.

19. An inkjet ink comprising a dye according to claim 1.

20. An inkjet printer comprising a printhead in fluid communication with at least one ink reservoir, wherein said at least one ink reservoir comprises an inkjet ink according to claim 19.

21. The inkjet printer of claim 20, wherein said printhead comprises:

a plurality of nozzles;

a bubble forming chamber corresponding to each of the nozzles respectively, the bubble forming chambers adapted to contain ejectable liquid; and

a heater element disposed in each of the bubble forming chambers

respectively, the heater element configured for thermal contact with the

ejectable liquid;

such that,

heating the heater element to a temperature above the boiling point of the ejectable liquid forms a gas bubble that causes the ejection of a drop of the ejectable liquid from the nozzle;

wherein,

the heater element is suspended in the ink chamber such that during use at least a portion of the heater element is encircled by, and in direct contact with, the ejectable fluid.

22. An ink cartridge for an inkjet printer, said ink cartridge comprising an inkjet ink according to claim 19.

23. The ink cartridge of claim 22, wherein said cartridge comprises:

a housing defining a plurality of storage areas wherein at least one of the storage areas contains colorant for printing information that is visible to the human eye and at least one of the other storage areas contains an inkjet ink according to claim 19.

24. The dye of claim 1, wherein said hydrophilic group is of formula —

CO₂Z, —

SO₃Z, —

OSO₃Z, —

PO₃Z₂ or —

OPO₃Z₂, wherein Z is H or a water-soluble cation.

25. The dye of claim 24, wherein Z is selected from Li⁺, Na⁺ or K⁺.

26. A method of enabling entry of data into a computer system via a printed form, the form containing human-readable information and machine-readable coded data, the coded data being indicative of an identity of the form and of a plurality of reference points of the form, the method including the steps of:

receiving, in the computer system and from a sensing device, indicating data regarding the identity of the form and a position of the sensing device relative to the form, the sensing device, when placed in an operative position relative to the form, generating the indicating data using at least some of the coded data;

identifying, in the computer system and from the indicating data, at least one field of the form; and

interpreting, in the computer system, at least some of the indicating data as it relates to the at least one field,

wherein said coded data comprises an IR-absorbing dye according to claim 1.

27. The method of claim 26 in which the at least one field is associated with at least one zone of the form, the identifying step including identifying that the position of the sensing device is within the at least one zone.

28. The method of claim 27 in which the indicating data includes movement data regarding movement of the sensing device relative to the form, the sensing device generating the movement data using at least some of the coded data, the identifying step including identifying that the movement of the sensing device is at least partially within the at least one zone.

29. A method of enabling entry of data into a computer system via a printed form, the form containing human-readable information and machine-readable coded data, the coded data being indicative of at least one field of the form, the method including the steps of:

receiving, in the computer system and from a sensing device, indicating data regarding the at least one field and including movement data regarding movement of the sensing device relative to the form, the sensing device, when moved relative to the form, generating the data regarding said at least one field using at least some of the coded data and generating the data regarding its own movement relative to the form; and

interpreting, in the computer system, at least some of said indicating data as it relates to said at least one field,

wherein said coded data comprises an IR-absorbing dye according to claim 1.

30. The method of claim 29 in which the sensing device generates the movement data using at least some of the coded data.

31. The method of claim 26 or claim 29 in which the at least one field is an action field and the interpreting step includes sending a message to an application associated with the action field.

32. The method of claim 31 in which the action field is a form submission action field and the message includes form data derived from at least one other field of the form.

33. The method of claim 26 or 29 in which the form is disposed on a surface of a product item and in which the coded data is indicative of an identity of the product item.

34. The method of claim 33 in which the coded data is formed from a plurality of coded data portions, each coded data portion being indicative of the identity of the product item.

35. The method of claim 33 in which the coded data is indicative of at least one of a Universal Product Code or an Electronic Product Code associated with the product item.

36. The method any one of claims 27, 28 and 29 in which the at least one field is a text field and the interpreting step includes converting at least some of the movement data to text.

37. The method any one of claims 27, 28 and 29 in which the at least one field is a drawing field.

38. The method any one of claims 27, 28 and 29 in which the at least one field is a checkbox field and the interpreting step includes interpreting at least some of the movement data as a check mark.

39. The method any one of claims 27, 28 and 29 in which the at least one field is a signature field and the interpreting step includes verifying that at least some of the movement data represents a signature of a user associated with the sensing device.

40. A method of enabling entry of data into a computer system via a product item, the product item having a printed surface containing human-readable information and machine-readable coded data, the coded data being indicative of an identity of the product item, the method including the steps of:

(a) receiving, in the computer system and from a sensing device, indicating data regarding the identity of the product item, the sensing device, when placed in an operative position relative to the product item, generating the indicating data using at least some of the coded data; and

(b) recording, in the computer system and using the indicating data, information relating to the product item,

wherein said coded data comprises an IR-absorbing dye according to claim 1.

41. A method of enabling retrieval of data from a computer system via a product item, the product item having a printed surface containing human-readable information and machine-readable coded data, the coded data being indicative of an identity of the product item, the method including the steps of:

(a) receiving, in the computer system and from a sensing device, indicating data regarding the identity of the product item, the sensing device, when placed in an operative position relative to the product item, generating the indicating data using at least some of the coded data;

(b) retrieving, in the computer system and using the indicating data, information relating to the product item; and

(c) outputting, from the computer system and to an output device, the information relating to the product item, the output device selected from the group comprising a display device and a printing device,

wherein said coded data comprises an IR-absorbing dye according to claim 1.

42. The method of claim 40 or 41 in which the coded data is formed from a plurality of coded data portions, each coded data portion being indicative of the identity of the product item.

43. The method of claim 40 or 41 in which the coded data is indicative of at least one of a Universal Product Code or an Electronic Product Code associated with the product item.

44. The method of any one of claims 26, 29, 40 or 41 in which the coded data is substantially invisible to an unaided human eye.

45. The dye of claim 1, wherein said hydrophilic group is a sulfonic acid group or a metal salt thereof.

46. The dye of claim 1, wherein said hydrophilic group is —

SO₃Na or —

SO₃K.

47. The dye of claim 1, wherein M is Ni.

48. An inkjet ink comprising a dye according to claim 1 and a singlet oxygen quencher.

49. An inkjet ink comprising a dye according to claim 1, said dye being preselected to minimize visible absorption by reducing intermolecular interactions between adjacent dye molecules.