Compounds with oxime ester and/or acyl groups

• US 9,127,017 B2
• Filed: 05/24/2012
• Issued: 09/08/2015
• 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-Philippe, Gaudreault, Philippe, Nguyen, My T.
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/122,126
• Publication Number:
  US 20140200350A1
• Time in Patent Office: 1,202 Days
• Field of Search: 548/416, 548/418, 548/441, 549/41, 549/456, 560/129
• 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—, —O—, —S—, or —C(═O)— and B represents a bond, —CH₂—, —NH—, —O—, —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 being:

2. The compound of claim 1, further comprising an acyl group, wherein the acyl group is —

C(═

O)—

R₃₀, wherein R₃₀ is optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, or aryl, each of which optionally comprising one or more oxygen atom, sulfur atom, nitrogen atom, carbonyl group, carbamate group, carbamide group, and/or ester group.

3. The compound of claim 2, 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 L is hydrogen or C₁-C₆ alkyl,

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, and

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.

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

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

6. The compound of claim 5, being of formula:

7. The compound of claim 6, wherein R₆ is alkyl optionally substituted with —

O—

C_1-6 alkyl.

8. The compound of claim 7, wherein R₆ is methyl.

9. The compound of claim 6, R₇ represents C₁-C₁₂ alkyl optionally substituted with phenyl;

C₄-C₁₀ cycloalkyl;

or phenyl optionally substituted with C₁-C₆ alkyl.

10. The compound of claim 9, wherein R₇ is methyl.

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

S-arylene, —

NH-arylene, and —

N(aryl)-arylene of LK 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 L is hydrogen or C₁-C₆ alkyl,

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, and

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.

12. The compound of claim 6, wherein

-LK-E₁ represents:

13. The compound of claim 6, wherein

each Q₁₁, Q₁₂, and Q₁₃, when present, represents one -E₁ of formula —

CR₆═

N—

O—

(C═

O)—

R₇, wherein R₆ represents C₁-C₁₂ alkyl optionally substituted with —

O-L, wherein L is C₁-C₆ alkyl, and R₇ represents C₁-C₁₂ alkyl;

all R₂₂, when present, represent hydrogen; and

all R₂₁, when present, represent hydrogen or C₁-C₁₂ alkyl.

14. The compound of claim 6, wherein:

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

CR₆═

N—

O—

(C═

O)—

R₇, wherein R₆ represents C₁-C₁₂ alkyl optionally substituted with —

O-L, wherein L is C₁-C₆ alkyl, and R₇ represents C₁-C₁₂ alkyl;

all R₂₂, when present, represent hydrogen;

all R₂₁, when present, represents hydrogen or C₁-C₁₂ alkyl; and

LK represents

15. The compound of claim 6, wherein each of Q₁₁, Q₁₂, and Q₁₃, when present, represents hydrogen, each R₂₂, when present, represents one —

N(R₁₉)-phenyl wherein R₁₉ represents C₁-C₁₂ alkyl, and every pair of R₂₁ attached to a common carbon atom represent =E₂ wherein R₇ represents C₁-C₁₂ alkyl.

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