Oxime ester

• US 9,051,397 B2
• Filed: 10/04/2011
• Issued: 06/09/2015
• Est. Priority Date: 10/05/2010
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Kura, Hisatoshi, Kunimoto, Kazuhiko, Tanaka, Keita, Nishimae, Yuichi, Yamagami, Ryuhei
• Primary Examiner(s): McPherson, John A
• Application Number:
  US13/824,678
• Publication Number:
  US 20130188270A1
• Time in Patent Office: 1,344 Days
• Field of Search: 548/311.4, 548/420, 544/142, 522/14, 522/36, 522/39, 522/63, 430/7, 430/280.1
• US Class Current: 1/1
• CPC Class Codes: B33Y 70/00 Materials specially adapted for additive manufacturing
• CPC Class Codes: C07D 209/80 [b, c]- or [b, d]-condensed
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: G02B 5/223 containing organic substances, e.g. dyes, inks or pigments
• CPC Class Codes: G03F 7/0007 Filters, e.g. additive colour filters; Components for display devices
• CPC Class Codes: G03F 7/029 Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
• CPC Class Codes: G03F 7/031 Organic compounds not covered by group G03F7/029
• CPC Class Codes: G03F 7/105 having substances, e.g. indicators, for forming visible images

Abstract

Compounds of the formula (I), wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ for example independently of each other are hydrogen, C₁-C₂₀alkyl, (II), COR₁₆ or NO₂, provided that at least one pair of R₁ and R₂, R₂ and R₃, R₃ and R₄, R₅ and R₆, R₆ and R₇, or R₇ and R₈ is (III); R₉, R₁₀, R₁₁ and R₁₂ for example independently of each other are hydrogen, C₁-C₂₀alkyl which optionally substituted; or R₉, R₁₀, R₁₁, and R₁₂ independently of each other are unsubstituted or substituted phenyl; X is CO or a direct bond; R₁₃ is for example C₁-C₂₀alkyl which optionally is substituted, C₂-C₁₂alkenyl, C₄-C₈cycloalkenyl, C₂-C₁₂alkinyl, C₃-C₁₀-cycloalkyl, phenyl or naphthyl both of which are optionally substituted; R₁₄ is for example hydrogen, C₃-C₈cycloalkyl, C₂-C₅alkenyl, C₁-C₂₀alkoxy, C₁-C₂₀alkyl, phenyl or naphthyl; R₁₅ is for example C₆-C₂₀aryl or C₅-C₂₀heteroaryl; R₁₆ is for example C₆-C₂₀aryl which is unsubstituted or substituted by one or more C₁-C₂₀alkoxy or C₁-C₂₀alkyl; are in particular suitable as photoinitiators for color filter applications.

Claims

1. A compound of formula I:

2. The compound according to claim 1,

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, and R₈ are independently hydrogen, C₁-C₂₀alkyl,

3. The compound according to claim 1, wherein

R₁, R₂, R₃, R₄, R₅, R₆, R₇, and R₈ are independently hydrogen,

or R₁ and R₂, R₃ and R₄, or R₅ and R₆, are together independently

4. A photopolymerizable composition, comprising:

an ethylenically unsaturated photopolymerizable compound; and

as a photoinitiator, the compound of claim 1.

5. The photopolymerizable composition according to claim 4,

wherein an ethylenically unsaturated photopolymerizable compound is a resin obtained by a process comprising reacting a saturated or unsaturated polybasic acid anhydride with a product obtained by a process comprising reacting an epoxy resin and an unsaturated monocarboxylic acid.

6. The photopolymerizable composition according to claim 4, further comprising:

an additional photoinitiator;

an additional additive;

or

any combination thereof.

7. The photopolymerizable composition according to claim 6, as the additional additive, the photopolymerizable composition comprises a pigment or a mixture of pigments.

8. The photopolymerizable composition according to claim 6, as the additional additive, the photopolymerizable composition comprises a dispersant or a mixture of dispersants.

9. The photopolymerizable composition according to claim 4, comprising 0.05 to 25% by weight of the photoinitiator, or the photoinitiator and additional photoinitiator, based on a total weight of the photopolymerizable composition.

10. The photopolymerizable composition according to claim 4 as the additional additive, the photopolymerizable composition comprises a photosensitizer.

11. The photopolymerizable composition according to claim 4, further comprising a binder polymer.

12. A process for photopolymerization of a compound comprising an ethylenically unsaturated double bond, comprising:

irradiating the photopolymerizable composition according to claim 4 with electromagnetic radiation from 150 to 600 nm, with electron beam, or with X-rays.

13. The process according to claim 12,

wherein the process is suitable for producing a pigmented and nonpigmented paint and varnish, a powder coating, a printing ink, a printing plate, an adhesive, a pressure sensitive adhesive, a dental compositions, a gel coat, a photoresist for an electronic, an electroplating resist, an etch resist, both liquid and dry films, a solder resist, a resist to manufacture color filters for a variety of display applications, a resist to generate a structure in manufacturing process of a plasma-display panel, an electroluminescence display and an LCD, a spacer for LCD, for holographic data storage (HDS), as a composition for encapsulating electrical and electronic components, for producing a magnetic recording material, an micromechanical part, a waveguide, an optical switch, a plating mask, an etch mask, a colour proofing system, a glass fibre cable coating, a screen printing stencil, for a producing three-dimensional object with stereolithography, as an image recording material, for a holographic recording, a microelectronic circuit, a decolorizing material, a decolorizing material for an image recording material, for an image recording material using a microcapsule, as a photoresist material for a UV and visible laser direct imaging system, as a photoresist material used for an forming dielectric layer in a sequential build-up layer of a printed circuit board.

14. A process for coating a coated substrate, comprising:

coating on a surface of the coated substrate with the composition according to claim 4.

15. A process for photographic production of a relief image, the process comprising:

exposing the coated substrate according to claim 14 in an imagewise

removing unexposed portions with a developer.

16. A process for preparing the compound according to claim 1, comprising:

reacting corresponding oxime compound with an acyl halide of formula II or an anhydride of formula III

17. A color filter prepared by a process comprising providing red, green, and blue picture elements, and a black matrix, all comprising a photosensitive resin and a pigment on a transparent substrate;

and

providing a transparent electrode either on a surface of the transparent substrate or on a surface of a layer of the color filter,

wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder, and the compound according to claim 1 as a photopolymerization initiator.

18. A process for photopolymerization of a composition comprising an ethylenically unsaturated photopolymerizable compound, the process comprising:

applying the compound according to claim 1.

19. A compound of formula (IA)