Naphthyl acrylates as writing monomers for photopolymers

Patent metadata

Field	Value
Publication number	US-10241402-B2
Application number	US-201515535086-A
Country	US
Kind code	B2
Filing date	Dec 9, 2015
Priority date	Dec 12, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The invention relates to naphthyl urethane acrylates particularly useful as writing monomers in photopolymer formulations for holographic media. The invention further relates to a photopolymer formulation comprising matrix polymers, writing monomers and photoinitiators, wherein the writing monomers comprise a naphthyl urethane acrylate according to the invention, to a holographic medium comprising matrix polymers, writing monomers and photoinitiators, wherein the writing monomers comprise a naphthyl urethane acrylate according to the invention, and also to a display comprising a holographic medium according to the invention.

First claim

The invention claimed is:

1. A photopolymer formulation comprising matrix polymers, writing monomers and photoinitiators, wherein the writing monomers comprise a compound according of formula (I)

a) which is substituted at least one of the carbon atoms 1, 2, 3, 4, 5, 6, 7, 8 with a moiety R arcyl of formula (II)

where in said formula (II)
R 1 is hydrogen or a (C 1 -C 6 )-alkyl group,
X is a carboxamide (—C(O)N—) or a carboxylic ester (—C(O)O—) or a sulphonamide (—SO 2 N—) group,
Y is a saturated or unsaturated or linear or branched optionally substituted moiety having 2-10 carbon atoms or a polyether having from one up to five (—CH 2 —CH 2 —O—)— or (—C(CH 3 )H—CH 2 —O—)— groups or a polyamine having from one to five nitrogen atoms, and
Z is oxygen or sulphur,

b) and the compound of formula (I) is substituted at not less than one of carbon atoms 1, 2, 3, 4, 5, 6, 7, or 8 with a naphthalene moiety of formula (III)

where in said formula (III)
the carbon atoms of the compound of formula (III) are each independently substituted with hydrogen, halogen, a cyano group, a nitro group or an optionally substituted alkyl, alkenyl, alkynl, aralkyl, aryl or heteroaryl group or an optionally substituted alkoxy or alkylthio group or any substituted carbamoyl group, which also may be linked bridgingly to a moiety of formula (I), or a trifluoromethyl group or a trifluoromethoxy group or a moiety R arcyl′ of formula (IV),

where in said formula (IV)
R 1 ′ is hydrogen or a (C1-C6)-alkyl group,
X′ is a carboxamide (—C(O)N—) or a carboxylic ester (—C(O)O—) or a sulphonamide (—SO 2 N—) group,
Y′ is a saturated or unsaturated or linear or branched optionally substituted moiety having 2-10 carbon atoms or a polyether having from one to five (—CH 2 —CH 2 —O—)— or (—C(CH 3 )H—CH 2 —O—)— groups or a polyamine having from one to five nitrogen atoms, and
Z is oxygen or sulphur,

the remaining carbon atoms of the compound of formula (I) are each independently substituted with hydrogen, halogen, a cyano group, a nitro group or an optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl group or an optionally substituted alkoxy or alkylthio group or a trifluoromethyl group or a trifluoromethoxy group.

2. The photopolymer formulation according to claim 1 , wherein it is substituted with the moiety of formula (III) on the carbon atom in position 5 of formula (I), wherein the moiety of formula (III) is preferably bonded to the carbon atom in position 5 via the carbon atom in position 8′.

3. The photopolymer formulation according to claim 1 , wherein it is substituted with the moiety R arcyl of formula (II) on the carbon atom in position 6 of formula (I).

4. The photopolymer formulation according to claim 1 , wherein the moiety of formula (III) is substituted with the moiety R′ of formula (IV) on the carbon atom in position 7′.

5. The photopolymer formulation according to claim 1 , wherein X is carboxamide in moiety R arcyl and/or X is carboxamide in moiety R′.

6. The photopolymer formulation according to claim 1 , wherein R 1 is hydrogen or a CH 3 moiety in moiety R arcyl and/or R 1′ is hydrogen or a CH 3 moiety in moiety R′.

7. The photopolymer formulation according to claim 1 , wherein Y is a —CH 2 —CH 2 moiety in moiety R arcyl and/or Y′ is a —CH 2 —CH 2 moiety in moiety R′.

8. The photopolymer formulation according to claim 1 , wherein Z and/or Z′ are oxygen.

9. A holographic medium comprising the photopolymer formulation according to claim 1 .

10. The holographic medium according to claim 9 , wherein the matrix polymers are crosslinked matrix polymers.

11. The holographic medium according to claim 9 , wherein the holographic medium comprises at least a fluorourethane as additive.

12. The holographic medium according to claim 9 , wherein the holographic medium is a film.

13. The holographic medium according to claim 9 , wherein the holographic medium contains at least one exposed hologram.

14. A display comprising a holographic medium according to claim 9 .

15. The holographic medium according to claim 9 , having a refractive index modulation Δn in the range from 0.037 to 0.060.

Assignees

• Covestro Deutschland Ag

Inventors

• Rölle Thomas
• Berneth Horst
• Bruder Friedrich-Karl
• Hönel Dennis
• Kostromine Serguei
• Fäcke Thomas

Classifications

• C08F20/38

  Esters containing sulfur · CPC title

• C08L75/04

  Polyurethanes · CPC title

• C07C323/43

  Y being a hetero atom · CPC title

• C07C271/48 Primary

  to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms · CPC title

• G03H2260/12

  Photopolymer · CPC title