Compounds with oxime ester and/or acyl groups

• US 9,382,259 B2
• Filed: 07/16/2015
• Issued: 07/05/2016
• Est. Priority Date: 05/25/2011
• Status: Expired due to Fees

• Current Assignee: American Dye Source, Inc.
• Original Assignee: American Dye Source, Inc.
• Inventors: Tremblay-Morin, Jean-Philipe, Nguyen, My T., Gaudreault, Philippe
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/801,223
• Publication Number:
  US 20160016964A1
• Time in Patent Office: 355 Days
• Field of Search: 548/416, 568/326, 549/59, 549/70
• US Class Current: 1/1
• CPC Class Codes: C07C 13/62 with more than three condensed rings
• CPC Class Codes: C07C 251/48 with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 251/64 by carboxylic acids
• CPC Class Codes: C07C 251/66 with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 2603/54 containing more than five condensed rings
• CPC Class Codes: C07C 323/47 to oxygen atoms
• CPC Class Codes: C07C 49/665 a keto group being part of a condensed ring system
• CPC Class Codes: C07C 49/792 containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 209/56 Ring systems containing three or more rings
• 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 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 307/92 Naphthofurans; Hydrogenated naphthofurans
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 333/78 condensed with rings other than six-membered or with ring systems containing such rings
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 487/14 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: C08F 4/00 : Polymerisation catalysts

Abstract

There are provided compounds comprising optionally substituted (FORMULA I) fused with one or two optionally substituted (FORMULA II), wherein A and E each independently represent —CH₂—, —NH—, -0-, —S—, or —C(═O)— and B represents a bond, —CH₂—, —NH—, -0-, —S—, or —C(═O)—, said compound having directly or indirectly attached thereto at least one acyl and/or oxime ester group. Such compounds are useful inter alias as photoinitiators.

Claims

1. A compound of formula:

2. The compound of claim 1, being of formula:

3. The compound of claim 1, wherein said alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, and aryl in R₃₀ is substituted with one or more:

polyethylene glycol chain,

C₁-C₁₂ alkyl optionally substituted with one or more;

—

NR₈R₉,

—

O-L,

—

S-L, and/or

phenyl optionally substituted with one or more;

C₁-C₆ alkyl, halogen, nitrile, alkyloxy, COOR₁₀, and/or C₂-C₁₂ alkylcarboxyl;

C₄-C₁₀ cycloalkyl, C₂-C₁₂ alkenyl, C₄-C₁₀ cycloalkenyl, C₂-C₁₂ alkynyl, C₄-C₁₀ cycloalkynyl, each of which being optionally substituted by alkyl and/or —

O-L, and/or

aryl, such as phenyl, thiophenyl, biphenyl and naphthyl, each of which being optionally substituted with one or more;

C₁-C₆ alkyl,

halogen,

nitrile,

alkyloxy,

—

COOR₁₀, and/or

C₂-C₁₂ alkylcarboxyl,

wherein R₈ is independently hydrogen, C₁-C₁₂ alkyl;

C₄-C₁₀ cycloalkyl;

C₁-C₁₂ alkenyl;

C₄-C₁₀ cycloalkenyl;

C₂-C₁₂ alkynyl;

C₄-C₁₀ cycloalkynyl;

C₁-C₁₂ haloalkyl;

or optionally substituted aryl, and

wherein each of R₉ and R₁₀ is independently hydrogen, C₁-C₁₂ alkyl;

C₄-C₁₀ cycloalkyl;

C₁-C₁₂ alkenyl;

C₄-C₁₀ cycloalkenyl;

C₂-C₁₂ alkynyl;

C₄-C₁₀ cycloalkynyl;

C₁-C₁₂ haloalkyl;

or

optionally substituted aryl.

4. The compound of claim 3, wherein R₃₀ is linear alkyl, phenyl or thiophenyl, all of which being optionally substituted with a linear alkyl or with —

O-L.

5. The compound of claim 4, wherein R₃₀ is methyl, 2-methylphenyl, phenyl, thiophenyl, or 4-methoxyphenyl.

6. The compound of claim 1, wherein -LK—

is optionally substituted alkylene, cycloalkylene, alkenylene, cycloalkenylene, alkynylene, cycloalkynylene, arylene, —

S-arylene, —

NH-arylene, or —

N(aryl)-arylene, each of which optionally comprising one or more oxygen atom, sulfur atom, nitrogen atom, carbonyl group, carbamate group, carbamide group, and/or ester group.

7. The compound of claim 6, wherein the alkylene, cycloalkylene, alkenylene, cycloalkenylene, alkynylene, cycloalkynylene, arylene, —

S-arylene, —

NH-arylene, and —

N(aryl)-arylene are substituted with one or more;

polyethylene glycol chain,

C₁-C₁₂ alkyl optionally substituted with one or more;

—

NR₈R₉,

—

O-L,

—

S-L, and/or

phenyl optionally substituted with one or more;

C₁-C₆ alkyl, halogen, nitrile, alkyloxy, COOR₁₀, and/or C₂-C₁₂ alkylcarboxyl;

C₄-C₁₀ cycloalkyl, C₂-C₁₂ alkenyl, C₄-C₁₀ cycloalkenyl, C₂-C₁₂ alkynyl, C₄-C₁₀ cycloalkynyl, each of which being optionally substituted by alkyl and/or —

O-L, and/or

aryl, such as phenyl, biphenyl and naphthyl, or aryloyl, such as benzoyl, each of which being optionally substituted with one or more;

C₁-C₆ alkyl,

halogen,

nitrile,

alkyloxy,

—

COOR₁₀, and/or

C₂-C₁₂ alkylcarboxyl,

wherein R₈ is independently hydrogen, C₁-C₁₂ alkyl;

C₄-C₁₀ cycloalkyl;

C₁-C₁₂ alkenyl;

C₄-C₁₀ cycloalkenyl;

C₂-C₁₂ alkynyl;

C₄-C₁₀ cycloalkynyl;

C₁-C₁₂ haloalkyl;

or optionally substituted aryl, and

wherein each of R₉ and R₁₀ is independently hydrogen, C₁-C₁₂ alkyl;

C₄-C₁₀ cycloalkyl;

C₁-C₁₂ alkenyl;

C₄-C₁₀ cycloalkenyl;

C₂-C₁₂ alkynyl;

C₄-C₁₀ cycloalkynyl;

C₁-C₁₂ haloalkyl;

or

optionally substituted aryl.

8. The compound according to claim 1, wherein:

-LK-E₁ represents;

9. The compound of claim 2, wherein

each Q₁₁, Q₁₂, and Q₁₃ represents one -LK-E₁ or -E₁, wherein E₁ is of formula —

C(═

O)—

R₃₀, wherein R₃₀ represents C₁-C₁₂ linear alkyl, phenyl, phenyl substituted with alkyl or alkyloxy, or thiophenyl;

all R₂₂ represent hydrogen;

all R₂₁ represent C₁-C₁₂ alkyl, and

-LK—

represents 2-phenylene or 4-phenylene,

provided that the compound comprises three acyl groups.

10. The compound of claim 1, being: