Photopolymer formulation for producing holographic media

Patent metadata

Field	Value
Publication number	US-9098065-B2
Application number	US-201113883911-A
Country	US
Kind code	B2
Filing date	Nov 4, 2011
Priority date	Nov 8, 2010
Publication date	Aug 4, 2015
Grant date	Aug 4, 2015

Abstract

The invention relates to a photopolymer formulation, comprising at least one polyol component, a polyisocyanate component, a write monomer, a photoinitiator, and a catalyst, wherein the photopolymer formulation has an activation temperature >8300 K. The invention further relates to a method for producing a holographic medium, to a holographic medium that can be obtained according to the method according to the invention, and to the use of a holographic medium according to the invention for producing a hologram.

First claim

The invention claimed is:

1. A method for preparing a photopolymer formulation comprising mixing a polyol component, a polyisocyanate component, a writing monomer, a photoinitiator, and a catalyst to form a liquid mixture and determining an activation temperature of the liquid mixture, wherein the photopolymer formulation has the activation temperature ≧8300 K, and wherein the activation temperature is determined by determining both the storage modulus G′ and the loss modulus G″ of the mixture over a measurement time t, at least until the condition of the gel point G′=G″=G Gel at time t Gel is reached, at temperatures T=303 K, 313 K, 328 K, 343 K and 353 K using a plate-plate measuring system of a rheometer at a plate spacing of 250 μm in the oscillation mode at a constant frequency f of 10 Hz and a regulated deformation amplitude of 10%; establishing a logarithmic plot of t Gel versus the respective inverse absolute temperature 1/T at which t Gel was determined; and using linear regression to determine the activation temperature T Akt as per the formula
ln( t Gel /min)= T Akt /T+A
as the slope of the straight line in the plot.

2. The method of claim 1 , wherein the activation temperature is ≧8700 K.

3. The method of claim 1 , wherein the polyol component has primary OH groups.

4. The method of claim 1 , wherein the polyisocyanate component is an aliphatic polyisocyanate or an aliphatic prepolymer.

5. The method of claim 1 , wherein the writing monomer comprises at least one monofunctional and one multifunctional urethane (meth)acrylate.

6. The method of claim 1 , wherein the photoinitiator comprises a combination of dyes by whose absorption spectra the spectral region from 400 to 800 nm is at least partly covered with at least one coinitiator adapted to the dyes.

7. The method of claim 1 , wherein said photopolymer formulation further comprises a plasticizer.

8. The method of claim 7 , wherein said plasticizer is a compound of formula (VI)

wherein
m is ≧1 and ≦8; and
R 8 , R 9 , and R 10 are, independently of each other, hydrogen or an optionally heteroatom-substituted linear, branched, cyclic, or heterocyclic organic radical.

9. The method of claim 1 , wherein the catalyst has the formula (II)
RSnL 3   (II)

wherein
R is an optionally heteroatom-substituted linear or branched alkyl radical containing from 1 to 30 carbon atoms; and
each L is, independently of the others, an − O 2 C—R 3 group, wherein R 3 is an optionally heteroatom-substituted linear or branched alkyl radical containing from 1 to 30 carbon atoms, an alkenyl radical containing from 2 to 30 carbon atoms, or an optionally substituted and optionally polycyclic aromatic or heteroaromatic ring.

10. The method of claim 9 , wherein R is a linear or branched alkyl radical containing from 1 to 12 carbon atoms and/or R3 is a linear or branched alkenyl radical containing from 2 to 17 carbon atoms or alkyl radical containing from 1 to 17 carbon atoms optionally substituted with heteroatoms.

11. The method of claim 1 , wherein the catalyst has the formula (III) or (IV)
Bi(III)M 3   (III),

Sn(II)M 2   (IV),

wherein
each M is, independently of the others, an − O 2 C—R 4 group wherein R 4 is a saturated or unsaturated or heteroatom-substituted C 1 - to C 19 -alkyl radical or C 2 - to C 19 alkenyl radical.

12. The method as claimed in claim 1 , characterized in that the catalyst the general formula (V)
FeQ 3   (V),

where each Q is independently of the others an organic anion of formula (Va),

where R 5 and R 7 are each independently of each other an optionally heteroatom-substituted C 1 - to C 18 -alkyl radical or C 2 -C 18 alkenyl radical, especially a C 1 - to C 10 -alkyl radical and more preferably a C 1 - to C 4 -alkyl radical or R 5 and R 6 combine to form a bridge, for example from —CH 2 —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —, —CH═CH—CH═CH—, or an optionally heteroatom-substituted aromatic or heteroaromatic ring and R 6 is methyl or hydrogen.

13. A process for producing a holographic medium comprising
(I) preparing a photopolymer formulation according to the method of claim 1 ;
(II) processing the photopolymer formulation at a processing temperature into the form desired for the holographic medium; and
(III) curing the photopolymer formulation in the desired form by urethane formation at a crosslinking temperature above the processing temperature.

14. The process of claim 13 , wherein the photopolymer formulation is processed in step II) into the form of a film.

15. The process of claim 14 , wherein the photopolymer formulation is applied flat to a carrier substrate.

16. The process of claim 13 , wherein the processing temperature is ≧15 and ≦40° C.

17. The process of claim 13 , wherein the crosslinking temperature is ≧60 and ≦100° C.

Assignees

• Hönel Dennis
• Weiser Marc-Stephan
• Bruder Friedrich-Karl
• Rölle Thomas
• Fäcke Thomas
• Berneth Horst
• Bayer Ip Gmbh

Inventors

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

Classifications

• G11B7/245

  containing a polymeric component · CPC title

• C08G18/242

  organometallic compounds containing tin-carbon bonds · CPC title

• G03H2260/14

  Photoresist · CPC title

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• G03F7/001

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