N-Substituted Imides As Polymerization Initiators

• US 20080132600A1
• Filed: 10/31/2005
• Published: 06/05/2008
• Est. Priority Date: 11/09/2004
• Status: Active Grant

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Powell, Karin, Nesvadba, Peter, Jung, Tunja, Bugnon, Lucienne, Benkhoff, Johannes
• Granted Patent: US 7,723,399 B2
• Time in Patent Office: Days
• US Class Current: 522/167
• CPC Class Codes: C07D 207/404 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
• CPC Class Codes: C07D 207/46 with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 221/14 Aza-phenalenes, e.g. 1,8-naphthalimide
• CPC Class Codes: C08F 4/00 Polymerisation catalysts

Abstract

The invention relates to novel N-substituted imides and polymerizable compositions comprising these N-substituted imides. The invention further relates to the use of N-substituted imides as polymerization initiators. The imides are compounds of the formula (I) and (II) wherein n is 1 or 2; m is 1 or 2; R₁ and R₂ are each, independently of one another, hydrogen, C₁-C₁₈alkyl, C₁-C₁₈alkenyl C₆-C₁₄aryl, aralkyl, C₅-C₁₂cycloalkyl, each of which may be substituted by halogen, C₁-C₄-alkyl, hydroxy, C₁-C₆alkoxy, carbonyl, C₁-C₆alkoxycarbonyl; or R₁ and R₂ together with the adjacent —CO—N—CO— group may form a monocyclic, bicyclic or polycyclic ring, said ring having up to 50 non hydrogen atoms and wherein said ring may contain the structural element (formula III) more than once; R₃ if n is 1, is C₁-C₁₈alkyl, C₆-C₁₄aryl, aralkyl, C₅-C₁₂cycloalkyl, OR₁₀ or SR₁₁, NR₁₂R₁₃; wherein R₃ if n is 2, is C₂-C₁₂alkylene, C₆-C₁₄arylene, xylylene R₄ and R₅, correspond to R₁ and R₂; R₆ if n is 1, is hydrogen, C₁-C₁₈alkyl, C₆-C₁₄aryl, aralkyl, C₅-C₁₂cycloalkyl, NR₁₄R₁₅; wherein R₆ if n is 2, is C₂-C₁₂alkylene, C₆-C₁₄arylene, xylylene; R₇ is hydrogen, C₁-C₁₈alkyl, C₆-C₁₄aryl, aralkyl, C₅-C₁₂cycloalkyl, each of which may be substituted by halogen, C₁-C₄-alkyl, hydroxy, C₁-C₆alkoxy, carbonyl, C₁-C₆alkoxy-carbonyl; or R₇ and R₁₄ or R₇ and R₁₅ form together with the N-atom attached to R₇ a 5-6 membered ring, optionally interrupted by —NH—, —N(C₁-C₈alkyl)-, —O- and/or S-atoms.

Claims

1. Compounds of the formula I and II

2. Compounds according to claim 1, wherein (R₁, R₂) and (R₃, R₄) together with the adjacent —

CO—

N—

CO—

group form a monocyclic, bicyclic or polycyclic ring, resulting in compounds of the formula Ia or IIa

3. Compounds according to claim 1, wherein (R₁, R₂) and (R₃, R₄) together with the adjacent —

CO—

N—

CO—

group form a bicyclic ring resulting in compounds of the formula Ib and IIb

4. Compounds according to claim 2, wherein A and A′

independently are phenylene, cyclohexylene, cyclohexenylene, 1,8-naphthylene or pyridinylene.

5. Compounds according to claim 2, wherein A and A′

independently are ethylene or propylene or ethylene or propylene substituted C₁-C₄alkyl.

6. A thermally curable coating composition, comprising

a) at least an ethylenically unsaturated compound;

b) a thermal initiator effective to enable IR-curing or NIR-curing or to enable microwave curing or to enable ultrasound curing or to enable the convection heat curing of the ethylenically unsaturated compound, wherein the thermal initiator is a N-substituted imide of the formula (I) and/or (II) according to claim 1.

7. A dual curable coating composition, comprising

a) at least an ethylenically unsaturated compound and a second thermal crosslinkable compound;

b) a thermal initiator effective to enable IR-curing or NIR-curing or to enable microwave curing or to enable ultrasound curing or to enable the convection heat curing of the ethylenically unsaturated compound, wherein the thermal initiator is a N-substituted imide of the formula (I) and/or (II) according to claim 1.

8. A double curable coating composition, comprising

a) at least an ethylenically unsaturated compound;

b) a thermal initiator effective to enable IR-curing or NIR-curing or to enable microwave curing or to enable ultrasound curing or to enable the convection heat curing of the ethylenically unsaturated compound, wherein the thermal initiator is a N-substituted imide of the formula (I) and/or (II) according to claim 1;

c) a photoinitiator effective to enable UV-curing of the ethylenically unsaturated compound.

9. (canceled)