Light absorbing compounds for optical polymers

Patent metadata

Field	Value
Publication number	US-9249249-B2
Application number	US-201314415697-A
Country	US
Kind code	B2
Filing date	Jun 25, 2013
Priority date	Jul 23, 2012
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

An optical polymeric material that can substantially block the transmission of ultraviolet light as well as selected portion of violet light. The polymeric material will include monomeric units of one or more lens monomers, and monomeric units of a monomer of formula (I).

First claim

The invention claimed is:

1. An optical polymer comprising: (a) monomeric units of one or more monomers suitable for producing optical polymeric materials and (b) monomeric units of a light-absorbing monomer having formula I

wherein A is NH or NR; B is OH, NH 2 , or F; R 1 and R 2 are independently selected from the group consisting of H, Me, Et, i-propyl, t-butyl, F, Cl, Br, I, OH, OR, NH 2 , NH 3 + , NHR, NR 2 , NH 2 R + , NR 3 + , CN, C(O)OH, C(O)OR, C(O)R, Ar, OAr, SH, SR, S(O)OR, and D; wherein at least one of R 1 and R 2 is D; wherein Ar is an aromatic monovalent radical having 6-10 carbon atoms, and Ar comprises a single ring or a condensed ring system, optionally substituted; D is an aliphatic radical with twelve or fewer carbon atoms that includes an ethylenic polymerizable group and is optionally substituted with oxygen or nitrogen; and R is a C 1 -C 6 alkyl.

2. The optical polymer of claim 1 ; wherein A is NH; and B is OH or NH 2 .

3. The optical polymer of claim 1 ; wherein R 1 is H, Me, Cl or OR, and R 2 is D.

4. The optical polymer of claim 1 ; wherein D is defined by the following formula

wherein R′ is C 2 -C 8 alkylene which may be straight chain or branched; E is O or nothing; and R″ is H or CH 3 .

5. The optical polymer of claim 1 ; wherein the monomeric units of the light-absorbing monomers are represented monomers having formula II

wherein G is H, Me, Cl or OR 5 , R 5 is C 1 -C 4 alkyl, and n is 0, 1, 2, 3, 4, 5 or 6.

6. The optical polymer of claim 1 ; wherein the monomeric units of the light-absorbing monomers are represented by monomers having the formula III

wherein G is H, Me, Cl or OR 5 ; R 5 is C 1 -C 4 alkyl; and n is 0, 1, 2, 3, 4, 5 or 6.

7. The optical polymer of claim 1 ; wherein the monomeric units of the light-absorbing monomers are represented by monomers having the formula IV

wherein A is NH or NR 5 ; G is H, Me, Et, i-propyl, t-butyl, CI or OR 5 ; and R 5 is C 1 -C 4 alkyl; and n is 0, 1, 2, 3, 4, 5 or 6.

8. The optical polymer of claim 1 ; wherein the monomeric units of formula I account for 0.1 wt % to 5 wt % of the polymer material.

9. The optical polymer of claim 1 ; wherein a one-millimeter thick sample of the polymer transmits less than 15% of light having wavelength of 420 nm, and more than 75% of light having wavelength of 450 nm therethrough.

10. The optical polymer of claim 1 ; wherein a one-millimeter thick sample of the polymer transmits less than 30% of light having wavelength of 420 nm, and more than 75% of light having wavelength of 450 nm therethrough.

11. The optical polymer of claim 1 , further comprising monomeric units of a UV-absorbing compound other than the compounds of formula I.

12. The optical polymer of claim 11 ; wherein the UV-absorbing compound other than the compounds of formula I includes a benzotriazole chemical structure.

13. The optical polymer of claim 1 , comprising hydrophilic monomeric units selected from the group consisting of: N-vinyl pyrrolidone, 2-hydroxyethyl methacrylate N, N-dimethyl acrylamide, acrylic acid, and methacrylic acid.

14. The optical polymer of claim 1 , comprising monomeric units of styrene and 2-hydroxyethyl methacrylate, which together account for greater than 50% by weight of the polymer.

15. The optical polymer of claim 1 , comprising monomeric units of N-vinyl-2-pyrrolidone, which accounts for greater than 80% by weight of the polymer.

16. An ophthalmic lens comprising the optical polymer material of claim 1 ; wherein the ophthalmic lens is a contact lens or an intraocular lens.

17. An optical polymer comprising: (a) monomeric units of one or more monomers suitable for producing optical polymeric materials, and (b) monomeric units of a light-absorbing monomer having formula IV

wherein A is NH or NR 5 ; G is H, C 1 -C 4 alkyl, Cl or OR 5 , and R 5 is C 1 -C 4 alkyl; and n is 0, 1, 2, 3, 4, 5 or 6.

18. The optical polymer of claim 17 ; wherein a one-millimeter thick sample of the polymer transmits less than 15% of light having wavelength of 420 nm, and more than 75% of light having wavelength of 450 nm, therethrough.

19. The optical polymer of claim 17 , comprising hydrophilic monomeric units selected from the group consisting of: N-vinyl pyrrolidone, 2-hydroxyethyl methacrylate N,N-dimethyl acrylamide, acrylic acid, and methacrylic acid.

20. The optical polymer of claim 17 , comprising monomeric units of styrene and 2-hydroxyethyl methacrylate, which together account for greater than 50% by weight of the polymer.

21. The optical polymer of claim 17 , comprising monomeric units of N-vinyl-2-pyrrolidone, which accounts for greater than 80% by weight of the polymer.

22. An optical polymer comprising: (a) monomeric units of one or more monomers suitable for producing optical polymeric materials; and (b) monomeric units of a light-absorbing monomer having formula I

wherein A is NH or NR; B is OH, NH 2 , or F; R 1 and R 2 are independently selected from the group consisting of H, Me, Et, i-propyl, t-butyl, F, Cl, Br, I, OH, OR, NH 2 , NH 3 + , NHR, NR 2 , NH 2 R + , NR 3 + , CN, C(O)OH, C(O)OR, C(O)R, Ar, OAr, SH, SR, S(O)OR, and D; wherein at least one of R 1 and R 2 is D; wherein Ar is an aromatic monovalent radical having 6-10 carbon atoms, and Ar comprises a single ring or a condensed ring system, optionally substituted; D is —R 4 , —OR 4 or —C(O)OR 4 , wherein R 4 is an aliphatic radical with four to twelve carbon atoms that includes an ethylenic polymerizable group; and R is a C 1 -C 6 alkyl.

Assignees

• Bausch & Lomb

Inventors

• Awasthi Alok Kumar
• Vanderbilt David P
• Meng Fanqing Richard

Classifications

• C08F220/40

  Esters of unsaturated alcohols {, e.g. allyl (meth)acrylate} · CPC title

• C08F220/306

  and polyethylene oxide chain in the alcohol moiety · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• G02B1/043

  Contact lenses · CPC title

• C08F226/10 Primary

  N-Vinyl-pyrrolidone · CPC title