Holographic media with improved light sensitivity

Patent metadata

Field	Value
Publication number	US-9804490-B2
Application number	US-201415105138-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Dec 20, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

The present invention provides a novel photopolymer formulation comprising matrix polymers, writing monomer and a photoinitiator and further comprising a compound of formula (1)

where A 1 , A 2 and A 3 are each independently hydrogen, fluorine, chlorine, bromine or iodine, R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, cyano, nitro, amino, alkylimino, azide, isonitrile, enamino, formyl, acyl, carboxyl, carboxylate, carboxamide, orthoester, sulphonate, phosphate, organosulphonyl, organosulphoxidyl, optionally fluorinated alkoxy or an optionally substituted aromatic, heteroaromatic, aliphatic, araliphatic, olefinic or acetylenic radical while suitable radicals may be connected together via bridge of any desired substitution, or in that two or more compounds of formula (I) may be connected together via at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 , in which case these radicals therein constitute a 2- to 4-tuply functional bridge, with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is not hydrogen. Further subjects of the invention are a photopolymer comprising matrix polymers, a writing monomer and photoinitiator, a holographic medium comprising a photopolymer formulation of the present invention or being obtainable by use thereof, the use of a holographic medium of the present invention and also a process for producing a holographic medium by using a photopolymer formulation of the present invention.

First claim

The invention claimed is:

1. A photopolymer formulation comprising matrix polymers, writing monomer and a photoinitiator, and a compound of formula (I)

where
A 1 , A 2 and A 3 are each independently hydrogen, fluorine, chlorine, bromine or iodine,
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from hydrogen, fluorine, chlorine, bromine or iodine with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is not hydrogen.

2. The photopolymer formulation according to claim 1 , wherein A 1 , A 2 and A 3 are all either fluorine, chlorine, bromine or iodine.

3. The photopolymer formulation according to claim 1 , wherein the matrix polymers are in a three-dimensionally crosslinked state.

4. The photopolymer formulation according to claim 1 , wherein the matrix polymers are polyurethanes.

5. The photopolymer formulation according to claim 4 , wherein the polyurethanes are prepared by reacting at least one polyisocyanate component with at least one isocyanate-reactive component.

6. A photopolymer comprising matrix polymers, writing monomer, a photoinitiator, and a compound of foimula (I)

where
A 1 , A 2 and A 3 are each independently hydrogen, fluorine, chlorine, bromine or iodine,
R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, cyano, isonitrile, carboxamide, orthoester, sulphonate, phosphate, organosulphonyl, organosulphoxidyl, or optionally fluorinated alkoxy, with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is not hydrogen.

7. The photopolymer according to claim 6 , wherein A 1 , A 2 and A 3 are each independently fluorine, chlorine, bromine or iodine.

8. The photopolymer according to claim 6 , wherein the matrix polymers are in a three-dimensionally crosslinked state.

9. The photopolymer according to claim 6 , wherein the matrix polymers are polyurethanes.

10. The photopolymer according to claim 9 , wherein the polyurethanes are prepared by reacting at least one polyisocyanate component with at least one isocyanate-reactive component.

11. The holographic medium in the form of a film being formed upon a substrate, comprising the photopolymer according to claim 6 .

12. The holographic medium according to claim 11 , wherein holographic information has been exposed into the photopolymer.

13. A process comprising providing the holographic medium according to claim 11 , and recording using an exposure process to produce at least one of in-line, off-axis, full-aperture transfer, white light transmission, reflection, Denisyuk, off-axis reflection, edge-lit or holographic stereograms, for production of optical elements, images or image depictions.

14. The process according to claim 13 , wherein the hologram is written by a pulsed laser.

15. A process for producing the holographic medium according to claim 11 , the process comprising applying the photopolymer on a substrate.

16. A photopolymer formulation comprising matrix polymers, writing monomer and a photoinitiator, and a compound of formula (I)

where
A 1 , A 2 and A 3 are each independently hydrogen, fluorine, chlorine, bromine or iodine,
R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, cyano, isonitrile, carboxamide, orthoester, sulphonate, phosphate, organosulphonyl, organosulphoxidyl, or optionally fluorinated alkoxy,-with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is not hydrogen,

wherein the matrix polymers are polyurethanes and wherein the polyurethanes are prepared by reacting at least one polyisocyanate component with at least one isocyanate-reactive component and wherein the at least one polyisocyanate component is an oligomerized aliphatic and/or cycloaliphatic di- or triisocyanates.

17. A photopolymer formulation comprising matrix polymers, writing monomer and a photoinitiator, and a compound of formula (I)

where
A 1 , A 2 and A 3 are each independently hydrogen, fluorine, chlorine, bromine or iodine,

R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, cyano, isonitrile, carboxamide, orthoester, sulphonate, phosphate, organosulphonyl, organosulphoxidyl, or optionally fluorinated alkoxy, with the proviso that at least one of the radicals R 1 , R 2 , R 3 , R 4 and R 5 is not hydrogen, wherein the photoinitiator is a mixture of one or more dyes with ammonium alkylarylborate(s).

Assignees

• Covestro Deutschland Ag

Inventors

• Rölle Thomas
• Berneth Horst
• Bruder Friedrich-Karl
• Hönel Dennis
• Fäcke Thomas
• Walze Günther
• Hagen Rainer
• Diedrich Christian

Classifications

• G03F7/001 Primary

  Phase modulating patterns, e.g. refractive index patterns · CPC title

• G03H1/02

  Details {of features involved during the holographic process; Replication of holograms without interference recording} · CPC title

• G03H2001/0264

  Organic recording material · CPC title

• C08L75/04

  Polyurethanes · CPC title

• G03F7/035

  the binders being polyurethanes · CPC title