Fluorescent compounds

Patent metadata

Field	Value
Publication number	US-9670365-B2
Application number	US-201213978837-A
Country	US
Kind code	B2
Filing date	Jan 11, 2012
Priority date	Jan 13, 2011
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

Disclosed are fluorescent compounds with large Stokes-shift and a process for their preparation. More particularly, disclosed are fluorescent compounds that are colorless. The compounds can be used in compositions for inks, paints and plastics, especially in a wide variety of printing systems and are particularly well-suited for security applications.

First claim

The invention claimed is:

1. A compound of formula

wherein
R 1 and R 1′ are each independently hydrogen, C 1 -C 18 alkyl, substituted C 1 -C 18 alkyl, C 6 -C 24 aryl, substituted C 6 -C 24 aryl, C 6 -C 24 heteroaryl, substituted C 6 -C 24 heteroaryl, halogen, or C 1 -C 18 alkoxy;
R 2 and R 2′ are each independently hydrogen, C 1 -C 18 alkyl, substituted C 1 -C 18 alkyl, C 6 -C 24 aryl, substituted C 6 -C 24 aryl, C 6 -C 24 heteroaryl, substituted C 6 -C 24 heteroaryl, halogen, or C 1 -C 18 alkoxy,
R 3 and R 3′ are each independently hydrogen, C 1 -C 19 alkyl, substituted C 1 -C 18 alkyl, C 6 -C 24 aryl, substituted C 6 -C 24 aryl, C 6 -C 24 heteroaryl, substituted C 6 -C 24 heteroaryl, halogen, or C 1 -C 18 alkoxy,
R 4 and R 4′ are each independently hydrogen, C 1 -C 18 alkyl, substituted C 1 -C 18 alkyl, C 6 -C 24 aryl, substituted C 6 -C 24 aryl, C 6 -C 24 heteroaryl, substituted C 6 -C 24 heteroaryl, halogen, or C 1 -C 18 alkoxy, or
one or more pairs of two substituents selected from the group consisting of R 1 and R 2 , R 1′ and R 2′ , R 3 and R 4 , and R 3′ and R 4′ together form a group

wherein
R 105 , R 106 , R 107 , and R 108 are each independently H, C 1 -C 18 alkyl, C 1 -C 18 alkyl interrupted by —O—, C 1 -C 18 alkoxy, or C 1 -C 18 alkoxy interrupted by —O—, and
Y is a linking group.

2. The compound of claim 1 , which is a compound of formula

a compound of formula

wherein R 2 and R 3 are each independently hydrogen or C 1 -C 8 alkyl, or a compound of formula

wherein R 1 and R 4 are each independently C 1 -C 8 alkoxy.

3. The compound of claim 1 , wherein Y is a group of formula —(Y 1 ) n1 —(Y 2 ) n2 —(Y 3 ) n3 —, wherein Y 1 and Y 3 are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 ring carbon atoms, Y 2 is —O—, —S—, —NR 12 —, —SO 2 —, —C(═O)—, —(CR 8 R 9 ) n4 —, —O—(CR 10 R 11 ) n5 —O—, R 8 and R 9 are each independently H or a C 1 -C 8 alkyl group, R 10 and R 11 are each independently H or a C 1 -C 8 alkyl group, R 12 is H, a C 1 -C 8 alkyl group, or a C 6 -C 10 aryl group, n1 is 1 or 2, n2 is 0 or 1, n3 is 0, 1, or 2, n4 is an integer of 1 to 4 and n5 is an integer of 1 to 4.

4. The compound of claim 3 , wherein Y is a group of formula

wherein R 5 , R 6 , R 5′ , R 6′ , R 5″ and R 6″ are each independently a C 1 -C 18 alkyl group or a C 1 -C 18 alkoxy group and R 13 is a C 1 -C 8 alkyl group.

5. The compound of claim 1 , wherein R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ , R 4 and R 4′ are each independently hydrogen, C 1 -C 8 alkoxy, halogen, CF 3 , or C 1 -C 8 alkyl, or one or more pairs of two substituents selected from the group consisting of R 1 and R 2 , R 1′ and R 2′ , R 3 and R 4 , and R 3′ and R 4′ together form a group

6. The compound of claim 1 , which is a compound of formula

wherein R 1 , R 2 , R 3 , R 4 and Y are, alternatively:

Compound
R 1
R 2
R 3
R 4
Y

A-1 
H
H
H
H

A-2 
H
H
H
H

A-3 
H
H
H
H

A-4 
H
H
H
H

A-5 
H
H
H
H

A-6 
H
H
H
H

A-7 
H
H
H
H

A-8 
H
H
H
H

A-9 
H
CH 3
CH 3
H

A-10
H
CH 3
CH 3
H

Assignees

• Eberius Karin
• Huegin Max
• Basf Se

Inventors

• Eberius Karin
• Huegin Max

Classifications

• B41M3/144

  using fluorescent, luminescent or iridescent effects · CPC title

• C09D11/50

  Sympathetic, colour changing or similar inks · CPC title

• C07D413/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• B42D25/29

  Securities; Bank notes · CPC title

• D21H21/40

  Agents facilitating proof of genuineness or preventing fraudulent alteration, e.g. for security paper (watermarking B41M3/10, D21F1/44; security printing B41M3/14; securities or banknotes characterised by colour effects B42D25/29, B42D25/30; testing paper currency or valuable papers for genuineness G07D7/00) · CPC title