US2012237856A1PendingUtilityA1
Selection method for additives in photopolymers
Est. expiryNov 3, 2029(~3.3 yrs left)· nominal 20-yr term from priority
Inventors:Thomas RölleFriedrich-Karl BruderThomas FäckeMarc-Stephan WeiserDennis HönelChristian Diedrich
G11B 7/24044G11B 7/245G03F 7/035G03H 2260/12G03H 1/02G03F 7/0046G11B 7/0065G03H 1/04G16C 20/30G03H 2001/0264G06F 7/548G03F 7/001G16C 10/00
43
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Claims
Abstract
The invention relates to a method for selecting compounds which can be used as additives in photopolymer formulations for producing light holographic media, and to photopolymer formulations which contain at least one softener which are selected according to the claimed method. The invention also relates to the use of photopolymer formulations for producing holographic media.
Claims
exact text as granted — not AI-modified1 .- 11 . (canceled)
12 . A method for selecting compounds which can be used as plasticizers in photopolymer formulations for the production of light holographic media, wherein the method comprises:
a) selecting a compound to be tested, b) carrying out a conformer analysis of the compound to be tested using a suitable computer programme, c) generating an optimization of the geometry of all conformers with the aid of a force field method and the conformer space is then further reduced with the aid of a similarity analysis, d) effecting a quantum chemical optimization of the geometry of the conformers which are energetically most favourable according to the force field optimization with the use of the B-P86 density functional and a triple □ valence basis set, and of the Conductor Like Screening Model (COSMO) in combination with the optimized COSMO radii or, if these do not exist for a given element, with 1.17 times the Bondi valence radius, e) calculating the area (A) in Å 2 and the enclosed volume (V) in Å 3 of the three-dimensional COSMO shielding charge density surfaces of the conformers having the lowest energy, which are obtained as result of the quantum chemical optimization of the geometry, f) dividing into segments, the COSMO shielding charge density surfaces of the conformers having the lowest energy with the aid of a suitable software package, the mean surface shielding charge density (□) of these segments are plotted in the form of a frequency distribution P(□) and the second moments (M 2 ) of this distribution, defined according to the equation:
M
2
=
10
·
∑
i
P
(
σ
i
)
·
σ
i
2
·
Δσ
are determined, □□ being the interval width of the discrete frequency distribution and the charge densities □ being stated in the unit e/nm 2 ,
g) averaging the volumes, areas and second moments of all conformers considered according to their weight in the Boltzmann distribution on the basis of the energies obtained from the quantum chemical optimizations of the geometries,
h) estimating the volatility of the substance according to the computational rule:
TGA
95
≈
207.015
·
M
2
A
+
41.405
·
V
3
-
253.2
,
i) estimating the density of the compound at room temperature with the aid of the equation:
ρ
=
0.89
·
M
V
·
N
A
-
0.2
·
A
V
+
0.01
·
M
2
□ being the density of the pure substance in g/cm 3 , M being the molar mass in g/mol, N A being the Avogadro number, A being the COSMO shielding charge density surface in Å 2 , V being the volume in Å 3 enclosed by the surface and M 2 being the second moment of the surface shielding charge density frequency distribution,
j) using the estimated density in order, with the aid of the Lorentz-Lorenz equation:
n
D
=
2
·
ρ
·
MP
M
+
1
1
-
ρ
·
MP
M
,
to convert the molar polarizability (MP) estimated according to a QSPR approach as accurately as possible into a refractive index at 589 nm (n D 20 )
k) determining whether the volatility of the compound to be tested is >100° C. and the refractive index thereof is ≦1.4600, the compound to be tested being classed as being suitable if both conditions are fulfilled.
13 . The method according to claim 12 , wherein, in step b), the computer program used to carry out the conformer analysis is the conformers module of the Materials Studio program package of Accelrys.
14 . The method according to claim 12 , wherein, in step f), the suitable software package is the program COSMOtherm of COSMOlogic.
15 . The method according to claim 12 , wherein, in step d), a quantum chemical optimization of the geometry of the conformer having the lowest energy according to the force field optimization is effected.
16 . The method according to claim 12 , wherein, in step d), a quantum chemical optimization of the geometry of all conformers in an energy window of 0-4 kJ/mol according to the force field optimization is effected.
17 . The method according to claim 12 , wherein, in step d), a quantum chemical optimization of the geometry of all conformers in an energy window of 0-8 kJ/mol according to the force field optimization is effected.
18 . The method according to claim 12 , wherein, in step k), a check is carried out to determine whether the volatility of the compound to be tested is >120° C. and the refractive index thereof nD is ≦1.4500.
19 . The method according to claim 12 , wherein, in step k), a check is carried out to determine whether the volatility of the compound to be tested is >120° C. and the refractive index thereof nD is ≦1.4400.
20 . The method according to claim 12 , wherein, in step k), a check is carried out to determine whether the volatility of the compound to be tested is >120° C. and the refractive index thereof nD is ≦1.4300.
21 . A photopolymer formulation comprising matrix polymers, writing monomers and photoinitiators, wherein the photopolymer formulation further comprises at least one plasticizer which is selected by the method according to claim 12 and wherein the matrix polymers comprise polyurethanes.
22 . The photopolymer formulation according to claim 21 , wherein the photoinitiators comprise an anionic, cationic or neutral dye and a coinitiator.
23 . The photopolymer formulation according to claim 21 , wherein the at least one plasticizer comprises urethanes, and wherein the urethane is capable of being substituted by at least one fluorine atom.
24 . The photopolymer formulation according to claim 23 , wherein the urethanes have the formula (II)
wherein
n is from 1 to 8 and
R 1 , R 2 , R 3 represent, independently of one another, hydrogen or linear, branched, cyclic or heterocyclic organic radicals which are unsubstituted or optionally also substituted by heteroatoms.
25 . The photopolymer formulation according to claim 24 , wherein at least one of the radicals R1, R2, R3 is substituted by at least one fluorine atom.
26 . The photopolymer formulation according to claim 24 , wherein R1 represents an organic radical having at least one fluorine atom.
27 . The photopolymer formulation according to claim 21 , wherein the writing monomers comprise a monofunctional acrylate of the formula (IV)
wherein
R 7 , R 8 , independently of one another, represent hydrogen or linear, branched, cyclic or heterocyclic organic radicals which are unsubstituted or optionally also substituted by heteroatoms.
28 . The photopolymer formulation according to claim 21 , wherein the writing monomers comprise a polyfunctional writing monomer.
29 . The photopolymer formulation according to claim 21 , wherein, the writing monomers comprise a polyfunctional acrylate.
30 . The photopolymer formulation according to claim 29 , wherein the polyfunctional acrylate has the formula (V)
wherein
n is from 2 to 4 and
R 9 , R 19 , independently of one another, represent hydrogen or linear, branched, cyclic or heterocyclic organic radicals which are unsubstituted or optionally also substituted by heteroatoms.
31 . A method comprising producing in-line holograms, off-axis holograms, full-aperture transfer holograms, white light transmission holograms, Denisyuk holograms, off-axis reflection holograms, edge-lit holograms or holographic stereograms, wherein the holograms or stereograms are produced with the photopolymer formulation according to claim 21 .Cited by (0)
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