Long-wave absorbing photoinitiators

Patent metadata

Field	Value
Publication number	US-11401287-B2
Application number	US-202117178678-A
Country	US
Kind code	B2
Filing date	Feb 18, 2021
Priority date	Feb 21, 2020
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

Compounds according to general formula (I)in which M is Ge or Sn, RAr isR1, R2, R3, R4, R5, independently of one another in each case, are —H, —F, —Cl, —OR6, —SR6, —N(R6)2, —CF3, —CN, —NO2, —COOR6, —CONHR6, a branched, cyclic or preferably linear C1-20 alkyl, C2-20 alkenyl, C1-20 alkyloxy or a C2-20 alkenoxy radical, which can be interrupted one or more times by O, S or —NR6— and substituted by one or more polymerizable groups and/or radicals R6, R6 is H, a branched, cyclic or preferably linear C1-20 alkyl or C2-20 alkenyl radical, R7 is a chemical bond, an n-valent aromatic radical or a branched, cyclic or preferably linear C1-20 alkylene radical, which can be interrupted one or more times by O, S or —NR6— and substituted by one or more polymerizable groups, ═O and/or radicals R6, n is 2 or 3 and m is 0 or 1. The compounds are particularly suitable as photoinitiators for radical polymerization and in particular for the production of dental materials.

First claim

The invention claimed is:

1. A compound according to general formula (I)

in which the variables have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H, —F, —Cl, —OR 6 , —SR 6 , —N(R 6 ) 2 , —CF 3 , —CN, —NO 2 , —COOR 6 , —CONHR 6 , a branched, cyclic or linear C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkyloxy or a C 2-20 alkenoxy radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups and/or radicals R 6 ,
R 6 in each case independently of one another H, a branched, cyclic or linear C 1-20 alkyl or C 2-20 alkenyl radical,
R 7 an n-valent aromatic radical or a branched, cyclic or linear C 2-20 alkylene radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups, ═O and/or radicals R 6 ,
n 2 or 3,
m 0 or 1.

2. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H, —F, —Cl, —OR 6 , —CF 3 , —CN, —COOR 6 , —CONHR 6 , a linear C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkyloxy or a C 2-20 alkenoxy radical, which can be interrupted one or more times by O or S and which can be substituted by one or more polymerizable groups and/or radicals R 6 ;
R 6 H, an aromatic radical or a linear C 1-10 alkyl radical, C 2-10 alkenyl radical,
R 7 a branched or linear n-valent C 2-10 alkylene radical, which can be interrupted one or more times by O or S and which can be substituted by one or more polymerizable groups, ═O and/or radicals R 6 ,
n 2,
m 0 or 1.

3. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H or a C 1-3 alkyl radical,
R 7 an n-valent benzene radical or an n-valent, linear C 2-8 alkyl radical,
n 2,
m 0 or 1.

4. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H or methyl,
R 7 an n-valent benzene radical or an n-valent, linear C 2-6 alkyl radical,
n 2,
m 0 or 1.

5. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge or Sn
RAr

R 7

n 2
m 1.

6. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge
RAr

R 7

n 3
m 1.

7. The compound according to claim 1 , wherein the variables of formula (I) have the following meanings:
M Ge
RAr

R 7 C 2 -C 8 alkylene, particularly preferably —C 4 H 8 —
n 2
m 0.

8. A composition which comprises at least one compound according to general formula (I)

in which the variables have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H, —F, —Cl, —OR 6 , —SR 6 , —N(R 6 ) 2 , —CF 3 , —CN, —NO 2 , —COOR 6 , —CONHR 6 , a branched, cyclic or linear C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkyloxy or a C 2-20 alkenoxy radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups and/or radicals R 6 ,
R 6 in each case independently of one another H, a branched, cyclic or linear C 1-20 alkyl or C 2-20 alkenyl radical,
R 7 an n-valent aromatic radical or a branched, cyclic or linear C 2-20 alkylene radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups, ═O and/or radicals R 6 ,
n 2 or 3,
m 0 or 1; and
at least one polymerizable monomer.

9. The composition which comprises at least one compound according to general formula (I)

in which the variables have the following meanings:
M Ge or Sn,
RAr

R 1 , R 2 , R 3 , R 4 , R 5 independently of one another in each case —H, —F, —Cl, —OR 6 , —SR 6 , —N(R 6 ) 2 , —CF 3 , —CN, —NO 2 , —COOR 6 , —CONHR 6 , a branched, cyclic or linear C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkyloxy or a C 2-20 alkenoxy radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups and/or radicals R 6 ,
R 6 in each case independently of one another H, a branched, cyclic or linear C 1-20 alkyl or C 2-20 alkenyl radical,
R 7 an n-valent aromatic radical or a branched, cyclic or linear C 2-20 alkylene radical, which can be interrupted one or more times by O, S or —NR 6 — and which can be substituted by one or more polymerizable groups, ═O and/or radicals R 6 ,
n 2 or 3,
m 0 or 1; and
at least one radically polymerizable monomer.

10. The composition according to claim 9 , which comprises 0.001 to 3 wt.-% of the at least one compound according to general formula (I), relative to the total mass of the composition.

11. The composition according to claim 10 , which comprises 0.001 to 1 wt.-% of the at least one compound according to general formula (I), relative to the total mass of the composition.

12. The composition according to claim 10 , which comprises 0.005 to 0.5 wt.-% of the at least one compound according to general formula (I), relative to the total mass of the composition.

13. The composition according to claim 9 , which comprises at least one mono- or multifunctional (meth)acrylate or a mixture thereof as the at least one radically polymerizable monomer.

14. The composition according to claim 9 , which comprises
(a) 0.001 to 3 wt.-% of at least one compound of general formula (I),
(b) 1 to 99.9 wt.-% of at least one radically polymerizable monomer,
(c) 0 to 85

Assignees

• Ivoclar Vivadent Ag

Inventors

• Moszner Norbert
• Catel Yohann
• Fässler Pascal
• Haas Michael
• Radebner Judith
• Stüger Harald

Classifications

• C07F7/2208

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C07F7/30 Primary

  Germanium compounds · CPC title

• C08K9/06

  with silicon-containing compounds · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• C08K3/40

  Glass · CPC title