Photopolymer formulations for producing holographic media having highly crosslinked matrix polymers

Patent metadata

Field	Value
Publication number	US-9760060-B2
Application number	US-201514826324-A
Country	US
Kind code	B2
Filing date	Aug 14, 2015
Priority date	Nov 8, 2010
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

The invention relates to a photopolymer formulation comprising a polyol component, a polyisocyanate component, a writing monomer, and a photoinitiator, containing a coinitiator and a dye having the formula F An, where F stands for a cationic dye and An″ stands for an anion, wherein the dye having the formula F An comprises a water absorption of =5%. The invention further relates to a holographic medium, in particular in the form of a film, containing a photopolymer formulation according to the invention, to the use of such a medium for recording holograms, and to a special dye that can be used in the photopolymer formulation according to the invention.

First claim

The invention claimed is:

1. A photopolymer formulation comprising a polyol component, a polyisocyanate component, a writing monomer and a photoinitiator containing a coinitiator and a dye of formula
F + An − ,
where
F + represents a cationic dye selected from the group consisting of acridine, xanthene, thioxanthene, phenazine, phenoxazine, tri(het)arylmethane, diamino(het)arylmethane, triamino(het)arylmethane, monomethinecyanine, dimethinecyanine, trimethinecyanine, hemicyanine, nullmethine, naphtholactam and streptocyanine dyes, and
An − is sec-C11- to C18-alkanesulphonate, C13- to C25-alkyl sulphate, branched C8- to C25-alkyl sulphate, optionally branched bis-C6- to C25-alkyl sulphosuccinate, sec- or tert-C4- to C25-alkylbenzenesulphonate, sulphonated or sulphated, optionally mono- or polyunsaturated C8- to C25-fatty acid esters of aliphatic C1- to C8-alcohols of glycerol, bis(sulpho-C2- to C6-alkyl) C3- to C12-alkanedicarboxylic esters, or (sulpho-C2- to C6-alkyl) C6- to C18-alkanecarboxylic esters,
wherein the dye of formula F + An − has a water imbibition of ≦5%, and wherein the anion An− has an AClogP in the range of 1-6.5.

2. The photopolymer formulation according to claim 1 , wherein the dye has a water imbibition of ≦3%.

3. The photopolymer formulation according to claim 1 , wherein the dye has a water imbibition of ≦2%.

4. The photopolymer formulation according to claim 1 , wherein the anion An− has a molar mass >150 g/mol.

5. The photopolymer formulation according to claim 1 , wherein the anion An− has an AClogP in the range of 1-4 and the anion An− has a molar mass >250 g/mol.

6. The photopolymer formulation according to claim 1 , wherein the anion An− has one or more than one linear or branched aliphatic moiety or when it has more than one linear or branched aliphatic moiety, these together have 8 to 36 carbon atoms.

7. The photopolymer formulation according to claim 1 , wherein the polyisocyanate component is an aliphatic polyisocyanate or a prepolymer with primary NCO groups.

8. The photopolymer formulation according to claim 1 , wherein the polyol component is a difunctional polyether, polyester or a polyether-polyester block copolyester with primary OH functions.

9. The photopolymer formulation according to claim 1 , wherein the writing monomer comprises at least a monofunctional and a multifunctional urethane (meth)acrylate.

10. The photopolymer formulation according to claim 1 , wherein it additionally comprises a plasticizer which conforms to general formula (CI)

where s is ≧1 and ≦8 and R 300 , R 301 , R 302 are independently of each other hydrogen, linear, branched, cyclic or heterocyclic unsubstituted or else optionally heteroatom-substituted organic moieties, wherein optionally at least one of R 300 , R 301 , R 302 is substituted with at least a fluorine atom and optionally R 30 ° is an organic moiety with at least one fluorine atom.

11. A holographic medium containing the photopolymer formulation according to claim 1 coated upon a substrate.

12. A process for recording of in-line, off-axis, full-aperture transfer, white light transmission, Denisyuk, off-axis reflection or edge-lit holograms or holographic stereograms, which comprises interferometrically exposing the holographic medium according to claim 11 .

Assignees

• Covestro Deutschland Ag

Inventors

• Berneth Horst
• Roelle Thomas
• Bruder Friedrich-Karl
• Fäcke Thomas
• Weiser Marc-Stephan
• Hönel Dennis

Classifications

• C09B23/166

  containing two or more nitrogen atoms (hydrazon dyes -CH=N-N- C09B26/02) · CPC title

• C09B23/105

  two >CH- groups · CPC title

• G03H2260/12

  Photopolymer · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B17/00

  Azine dyes · CPC title