Compounds for optically active devices

Patent metadata

Field	Value
Publication number	US-11001576-B2
Application number	US-201816485847-A
Country	US
Kind code	B2
Filing date	Feb 14, 2018
Priority date	Feb 15, 2017
Publication date	May 11, 2021
Grant date	May 11, 2021

Abstract

The present invention relates to novel compounds, particularly to compounds comprising a photoactive unit, said novel compounds being particularly suitable for compositions and ophthalmic devices as well as to compositions and ophthalmic devices comprising such compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
X is O, S or NR 0 ,
X 0 is O or S,
d is 0 or 1,

is selected from the group consisting of

wherein * denotes a linkage to [—R 2 —R 1 ],
R is at each occurrence independently H, F, OH, a linear or branched alkyl group having 1 to 4 C atoms, a linear or branched hydroxyalkyl group having 1 to 4 C atoms or a linear or branched partially or fully fluorinated alkyl group having 1 to 4 C atoms,
R′ is at each occurrence independently H, F, a linear or branched, non-halogenated, partially or completely halogenated alkyl group having 1 to 20 C atoms, a linear or branched hydroxyalkyl group having 1 to 20 C atoms, a non-halogenated, partially or completely halogenated cycloalkyl group having 3 to 6 C atoms, a linear or branched, non-halogenated, partially or completely halogenated alkoxy group having 1 to 20 C atoms, a linear or branched, non-halogenated, partially or completely halogenated thioalkyl group having 1 to 20 C atoms,
R 0 is at each occurrence independently a linear or branched alkyl group having 1 to 10 C atoms or a cycloalkyl group having 3 to 6 C atoms,
R 1 is a polymerizable group selected from the group consisting of alkenyl groups of formula (1), trialkoxysilyl groups, dialkoxyalkylsilyl groups, silyl groups of formula (2), silyl groups of formula (3) and silyl groups of formula (4),

wherein
X 4 is O, S, C(═O), or C(═O)O,
R 7 , R 8 , R 9 are at each occurrence independently of each other H, F, a linear or branched, non-fluorinated, partially or completely fluorinated alkyl having 1 to 20 C atoms or aryl with 6 to 14 C atoms,
c is 0 or 1,
* denotes a linkage to [—R 2 —];
wherein, in the trialkoxysilyl groups and dialkoxyalkylsilyl groups the alkyl and/or alkoxy groups are each independently linear or branched having 1 to 6 C atoms;

wherein
alkyl means at each occurrence independently of each other a linear or branched alkyl group having 1 to 6 C atoms, and
* denotes at each occurrence independently of each other a linkage to [—R 2 —],

—R 2 — is (C(R) 2 ) o —, —(C(R) 2 ) p —X 1 —(C(R) 2 ) q —(X 2 ) s —(C(R) 2 ) r —(X 3 ) t —(C(R) 2 ) u —, or a cycloalkylene group having 5 or 6 C atoms substituted with at least one R which is different from H,
o is 1 to 20,
X 1 , X 2 , X 3 are at each occurrence independently O, S or NR 0 ,
s, t are at each occurrence independently is 0 or 1,
p, q are at each occurrence independently 1 to 10,
r, u are at each occurrence independently 0 to 10,
wherein the overall number of atoms for —(C(R) 2 ) p —X 1 —(C(R) 2 ) q —(X 2 ) s —(C(R) 2 ) r —(X 3 ) t —(C(R) 2 ) u — is up to 20 atoms,
R 3 , R 4 , R 5 , R 6 are at each occurrence independently R′.

2. The compound according to claim 1 , wherein

is

3. The compound according to claim 1 , wherein d is 1.

4. The compound according to claim 1 , wherein d is 1 and X and X 0 are 0.

5. The compound according to claim 1 , wherein at least one R′ is not H.

6. The compound according to claim 1 , wherein at least two R′ are not H.

7. The compound according to claim 1 , wherein at least four R′ are not H.

8. The compound according to claim 1 , wherein R 3 , R 4 , R 5 , R 6 at each occurrence are identical.

9. The compound according to claim 1 , wherein R 2 is —(C(R) 2 ) o —.

10. The compound according to claim 1 , wherein R 1 is an acryl or methacryl radical.

11. An oligomer or polymer comprising a polymerized compound of formula I according to claim 1 .

12. A composition comprising at least one compound of formula (I) according to claim 1 and/or an oligomer or polymer comprising a polymerized compound of formula (I).

13. An article comprising at least one compound of formula (I) according to claim 1 or at least one oligomer or polymer comprising a polymerized compound of formula (I).

14. The article according to claim 13 , which is a blank which may be transformed into an eye implant or is an eye implant.

15. A process of forming an article of claim 13 , comprising
providing a composition comprising at least one compound of formula (I) and/or an oligomer or polymer comprising a polymerized compound of formula (I);
subsequently forming the article of said composition.

16. A process of changing an optical property of an article according to claim 13 , comprising exposing said article to irradiation having a wavelength of at least 200 nm and at most 1500 nm.

17. The article according to claim 13 , which is an intraocular lens.

Assignees

• Merck Patent Gmbh

Inventors

• Dobelmann-Mara Lars
• Riedmueller Stefan
• Schraub Martin

Classifications

• C07D409/12

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

• C07D407/12 Primary

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

• C08F126/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08F128/06

  by a heterocyclic ring containing sulfur · CPC title

• C07D209/12

  Radicals substituted by oxygen atoms · CPC title