IP Library Granted Patent US 9,760,060
Granted Patent B2
US 9,760,060 · App. 14/826,324 · Granted Sep 12, 2017

Photopolymer formulations for producing holographic media having highly crosslinked matrix polymers

Inventors: Horst Berneth (Leverkusen, DE); Thomas Roelle (Leverkusen, DE); Friedrich-Karl Bruder (Krefeld, DE); Thomas Fäcke (Leverkusen, DE); Marc-Stephan Weiser (Leverkusen, DE); Dennis Hönel (Zülpich-Wichterich, DE)
Assignee: Covestro Deutschland AG
G03H1/024C09B11/12C09B17/00C09B21/00C09B23/04C09B23/06C09B23/083C09B23/105C09B23/166C09B49/12C09B55/009C09B57/00C09B69/06C09B69/065G03C1/00G03F7/0045G03F7/035G03H1/00G11B7/245G03H2260/12G03H2260/14G11B7/24044
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Quick Facts
Patent No.
US 9,760,060
App. No.
14/826,324
Granted
Sep 12, 2017
Kind
B2
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.

Claims (18)

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 .

Assignments (3)
CHANGE OF NAME Recorded Mar 23, 2017
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 042103/0813 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2017
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER MATERIALSCIENCE AG
Reel/Frame 041675/0614 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2015
From: BERNETH, HORST; ROLLE, THOMAS; BRUDER, FRIEDRICH-KARL; FACKE, THOMAS; WEISER, MARC-STEPHAN; HONEL, DENNIS
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 036326/0952 →
Priority Claims (1)
EP 10190324 · Nov 8, 2010 · regional
Continuity (2)
Division 13883008
Related Publication 20160054704A1 · Feb 25, 2016