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US 11,053,404 B2Granted
Acylphosphine oxide photoinitiators
AssigneeAgfa NV
InventorJohan Loccufier
Life of this patent
Estimating the term…
Abstract
Thiol modified acylphosphine oxide photoinitiators exhibiting improved smell and extractability are disclosed. Also disclosed is a UV curable inkjet ink containing an acylphosphine oxide photoinitiator and a polymerizable compound, wherein the acylphosphine oxide photoinitiator includes one or more acyl groups substituted by a thiol.
Claims10
An acylphosphine oxide photoinitiator selected from the group consisting of:
- or
- the acylphosphine oxide photoinitiator is a compound according to Formula (I) or (IV):
- wherein
- n represents an integer having a value of 0 or 1;
- R2 is selected from the group consisting of hydrogen, an alkyl group, an alkoxy group, a group according to Formula (I-a), a —NH—C(═O)—R26 group, a —NH—C(═O)—O—R27 group, and a —NH—C(═)O—NH—R28 group;
- R26 to R28 are independently selected from the group consisting of an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alkaryl group, an aralkyl group, and a heteroaryl group;
- R1, R3, R4, and R5 are independently selected from the group consisting of hydrogen, an alkyl group, an alkoxy group, and a group according to Formula (I-a);
- at least one of R1 to R5 is a group substituted by a thiol or a group according to Formula (I-a):
- wherein
- Q is a z-valent linking group containing 6 to 30 carbon atoms in which z=k+p+m and z≤6, k=1 to z-p-m, p=0 to 2, and m=1 to 5;
- A is a group according to Formula (I-b):
- wherein
- R1 to R5 have a same meaning as a meaning in Formula (I) in which Q is coupled to the aromatic ring of A in any one of positions occupied by R1 to R5;
- R8 and R9 are independently selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, and an aryloxy group;
- R10 represents an alkyl group substituted by a thiol or an aryl group substituted by a thiol;
- R6 is selected from an alkyl group, an aryl group, an alkoxy group, and an aryloxy group if n=0, and if n=1 R6 represents an alkyl group substituted by a thiol or an aryl group substituted by a thiol;
- R7 is selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, an aryloxy group, and a group according to Formula (I-c):
- wherein
- R1 to R6 and n have a same meaning as a meaning in Formula (I);
- s is an integer having a value of 0 to 4;
- t is an integer having a value of 1 to 5;
- u=s+t+1;
- and
- L represents a u-valent linking group having 2 to 16 carbon atoms;
- R16 and R21 are independently selected from the group consisting of hydrogen, an alkyl group, an alkoxy group, a group according to Formula (I-a), a —NH—C(═O)—R26 group, a —NH—C(═O)—O—R27 group, and a —NH—C(═)O—NH—R28 group;
- R26 to R28 are independently selected from the group consisting of an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alkaryl group, an aralkyl group, and a heteroaryl group;
- R15, R17 to R20, and R22 to R24 are independently selected from the group consisting of hydrogen, an alkyl group, and an alkoxy group;
- at least one of R15 to R19 is a group substituted by a thiol and at least one of R20 to R24 is a group substituted by a thiol;
- and
- R25 is selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alkaryl group, an aralkyl group, an aryl group, a heteroaryl group, an alkoxy group, and an aryloxy group;
- wherein
- one or more of the groups R5, R6, R10, and R15 to R24 are substituted by a thiol represented by Formula (II):
- wherein
- * represents a point of attachment;
- X is selected from the group consisting of O, S, and NR11;
- L represents a divalent linking group including no more than 15 carbon atoms;
- n represents 0 or 1;
- R11 is selected from the group consisting of a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkaryl group, an aralkyl group, an aryl or heteroaryl group, and NR12R13;
- R12 and R13 are independently selected from the group consisting of a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkaryl group, an aralkyl group, an aryl, a heteroaryl group, and an acyl group;
- or
- one of the groups R3, R4, R5, R6, R10, and R15 to R24 are substituted by a thiol represented by Formula (III):
- wherein
- * represents a point of attachment;
- o represents an integer selected from 0 and 1;
- m and n independently represent an integer selected from 1 to 5;
- L represents an n+m-valent linking group including no more than 15 carbon atoms;
- and
- R14 is selected from the group consisting of a hydrogen and an alkyl group.
45 more elements
Dependencies are inferred from the claim text.