Holographic media and photopolymers

• US 8,329,773 B2
• Filed: 02/16/2010
• Issued: 12/11/2012
• Est. Priority Date: 02/17/2009
• Status: Active Grant

• Current Assignee: Covestro Deutschland AG
• Original Assignee: Bayer Materialscience AG (Covestro AG)
• Inventors: Fäcke, Thomas, Bruder, Friedrich-Karl, Weiser, Marc-Stephan, Rölle, Thomas, Hönel, Dennis
• Primary Examiner(s): McClendon, Sanza
• Application Number:
  US12/706,248
• Publication Number:
  US 20110065827A1
• Time in Patent Office: 1,029 Days
• Field of Search: 522/90, 522/97, 522/96, 522/151, 522/152, 522/173, 522/174, 522/162, 522/164, 522/166, 522/170, 430/269, 430/270.1, 430/280.1, 430/281.1, 430/284.1, 430/286.1
• US Class Current: 522/97
• CPC Class Codes: C08G 18/4244 containing oxygen in the form of ether groups
• CPC Class Codes: C08G 18/4887 containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/735 containing one isocyanate or isothiocyanate group linked to a primary carbon atom and at least one isocyanate or isothiocyanate group linked to a tertiary carbon atom
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C08G 18/776 phosphorus
• CPC Class Codes: C08G 18/7887 having two nitrogen atoms in the ring
• CPC Class Codes: G03F 7/001 Phase modulating patterns, e.g. refractive index patterns
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence
• CPC Class Codes: G03H 1/02 Details of features involved during the holographic process; Replication of holograms without interference recording
• CPC Class Codes: G03H 2001/0264 Organic recording material
• CPC Class Codes: G03H 2260/12 Photopolymer

Abstract

The invention relates to holographic media containing specific photopolymers, a process for the production thereof, and unsaturated glycidyl ether acrylate urethanes as writing monomers which are suitable for the preparation of photopolymers.

Claims

1. A photopolymer composition comprising

a) an unsaturated glycidyl ether acrylate urethane of formula (1a), formula (1b), or mixtures thereof

2. The photopolymer composition of claim 1, wherein

R1 is oxyphenyl, oxybromophenyl, oxydibromophenyl, or oxynaphthyl;

R2 is derived from an acid R2-COOH, wherein R2-COOH is selected from the group consisting of acrylic acid, methacrylic acid, 3-acrylyloxypropionic acid, or an adduct of hydroxyethyl and hydroxybutyl acrylate with maleic anhydride; and

R is derived from an n-functional isocyanate R(NCO)_n, wherein R(NCO)_n, is selected from the group consisting of 2,6-hexamethylene diisocyanate, 2,4,4-trimethyl-1,6-hexamethylene diisocyanate, isocyanatomethyl-1,8-octane diisocyanate, tris(p-isocyanatophenyl) thiophosphates, tris(4,4′

- and/or 2,4′

-) diisocyanatodicyclohexylmethane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane, diisocyanatodicyclohexylmethane 2,4- and/or 2,6-toluidene diisocyanate, and trimers of hexamethylene diisocyanate having an isocyanurate and/or iminooxadiazinetrione structure.

3. The photopolymer composition of claim 1, wherein said unsaturated glycidyl ether acrylate urethane of a) has a refractive index at 405 nm of greater than 1.53.

4. The photopolymer composition of claim 1, wherein said crosslinked binder is a two-component polyurethane system.

5. The photopolymer composition of claim 4, wherein said two-component polyurethane system comprises, as the isocyanate component, oligo- and polyisocyanates of aliphatic diisocyanates comprising an isocyanurate, allophanate, biuret, uretdione, or iminooxadiazinedione structure, and the polyol component comprises polyethylene/polypropylene glycols having a polypropylene content of at least 70% and a functionality of from 1.9 to 2.5 and/or polyester-polyether-polyester block polyols based on polytetrahydrofurans having a number average molecular weight of from 400 to 1400 g/mol and s-caprolactone, wherein said polyester-polyether-polyester block polyols have a number average molecular weight of from 1500 to 4000 g/mol.

6. A process for producing a medium for recording visual holograms, comprising applying the photopolymer composition of claim 1 to a substrate or in a mould and curing said photopolymer composition.

7. The medium for recording visual holograms produced by the process of claim 6.

8. An optical element or image comprising the medium of claim 7.

9. A glycidyl ether acrylate urethane of formula (1a) or (1b)