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Ciba Specialt
`Coating Effects
`
`Chem-10515
`
`
`
`
`
`Ciba '
`
`Ciba® CGI 403 Photoinitiator
`
`A Comparison of CGI 403 to Irgacure® 819
`
`CGI 403 and Irgacure 819 are both bis—acylphosphine oxide (BAPO) photoinitiators, which exhibit similar
`‘ properties. In Table 1, the relevant physical properties of CGI 403 and Irgacure 819 are compared. It is found, for
`example, that .both are solid yellow powders. The molecular weights are also similar. Both have long wavelength
`absorption tails that extend up to 430 nm. The solubilities in common solvents and monomers are also qualitatively
`similar.
`
`The photophysics and reactivity of both CGI 403 and Irgacure 819 are similar‘m]: both undergo rapid (< 1 nsee)
`bond cleavage from the excited state triplet manifold with very high efficiencies and both undergo permanent
`photobleaching upon excitation.
`
`Table 1. Comarison ofCGI 403 and Ir_aeure 819 uhotoinitiators
`— CGI 403
`Composition
`
`Ir-acure 819
`
`Chemical Identity
`
`bis(2,6-Dimethoxybenzoyl)-
`(2,4,4-trimethylpentyl)
`.hos hine oxide
`
`bis(2,4,6-trimethylbenzoyl)~
`phenylphosphine oxide
`
`162881-264
`417.97
`Yellow -owder
`127—132
`
`
`
`Thermal Gravlmetrlc
`Analysis [1] :
`5% wt loss temp. (°C)
`10% wt loss temp. (°C)
`15% wt loss tem: .
`
`Absorption Spectra,
`Extinction coefficients
`
`(mL/g.cm) at mercury lines:
`254 nm a
`302 nm :
`313 nm :
`365 nm :
`
`405 nm :
`435 um :
`
`'
`
`. q
`-
`Exhibit No» m
`Deponent'.
`DatelRPfi:W
`Hunter + Gem, InchB
`
`Edition: 02.08.01, Tarrytown
`
`2001 Ciba Specialty Chemicals Corporation
`
`Page 1 of5
`
`DSM IP Assets B.V. - Ex. No. 2100
`
`Coming v. DSM
`|PR2013-00049
`
`DSM IP Assets B.V. - Ex. No. 2100
`Corning v. DSM
`IPR2013-00049
`
`

`

`Ciba Specialty Chemicals
`
`
`
`
`
`Coating Effects
`
`Table 1 cont.
`
`Solubility in Common
`MonomerSISolvents [2]
`(wt% dissolved at 22°C):
`Acetone :
`
`n~Butyl Acetate :
`[BOA :
`IDA :
`PEA :
`HDDA:
`TrPGDA :
`TMPTA :
`Ln
`TMPEOTA :
`
`[1] TGA in N; at 10°Cfmin.
`[2] IBOA = isobornyl acrylatc; IDA = isodecyl acrylate; PEA = 2-phenoxyethyl acrylate; HDDA = hexane diol
`diacrylate; TrPGDA = tripropyleneglycol diacrylate; TMPTA = trimethyolpropanc triacrylate; TMPEOTA =
`trimethylolpropane ethoxytriacrylate.
`
`vmumn—nmu‘a—-U4‘:-
`
`Absorption Spectra of CGl-403 and Irgacure 819 in methanol
`
`'
`
`2.5
`
`2.0
`
`Absorbance
`
`
`
`300
`
`350
`
`400
`
`Wavelengths (nm)
`
`Figure 1. Comparison of the electronic absorption spectra of CGI 403 and Irgacure 319 at l x 1041 glmL
`concentration in methanol. Pathlength = 1 cm.
`
`Edition: 02.08.01, Tarrytown
`
`2001 Ciba Specialty Chemicals Corporation
`
`Page 2 of 5
`
`

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`
`Absorption Spectra of CGI-403 vs. lrgacure 819
`at equal molarity, in methanol
`
`
`
`
`o
`
`lrgacure 819 (1 mglmL)
`
`
`
`
`—-~— CGI-403 (1.2 mgr'mL)
`
`
`
`
`
`
`
` Absorbance
`
`
`
`
`
`
`
`380
`
`400
`
`420
`
`440
`
`460
`
`wavlength (nm)
`
`
`
`Figure 2. Absorption spectra of CGI 403 and lrgacure 819 at equal molar concentrations in methanol.
`
`the long wavelength spectra are effectively superimposable at equal
`As shown in the absorption spectra (Fig. 2),
`molar concentrations. On a weight basis this means that a spectral match at long wavelengths is obtained when [CGI
`403], wt% = l.2*[Irgacure 819], wt%.
`
`For composites and gel coating applications, the CGI 403 and the Irgcaure 819 photoinitiators were found to be
`essentially equivalent [4] (Fig. 3). For example, the lrgacure 1800 and lrgacure 1850 (which are CGI 403flrgacure
`184 blends) had very similar effects on the cure response compared to the lrgacure 819i’lrgacure 184. blend.
`
`For white pigmented inks, the percent double bond conversion and cure speed using lrgacure 819 were, however,
`higher compared to CGI 403 on'an equal weight basis. This difference is explained in part by the difference in
`MW’s. The performance of two BAPOr'oL-HK. blends for a white screen ink is given in Fig. 4.
`
`Edition: 02.08.01, Tarrytown
`
`2001 Ciba Specialty Chemicals Corporation
`
`, Page 3 of 5
`
`

`

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`Ciba Specialty Chemlcals
`
`Coating Effects
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`12 T...........................................................................................................
`MetalHallde Lamp atz=2o cm
`25‘.
`Hetron 922 Vinyl Estero'Styrene +1 pph Photolnitiator
`if
`
`I
`“g
`"3
`7'
`3:35
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`10
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`E“
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`“'3fl
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`319
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`TPO
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`851
`
`184
`
`369
`
`1300
`
`907'
`
`2959‘“
`
`
`
`Figure 3. Effect of photoinitiator to cure composites and thick polymer coatings. Note that fastest cure speeds were
`obtained with BAPOfaHK blends.
`
`Formulation:
`Plgment:
`Screen:
`Substrate:
`
`aliphurethsne diacrylate .’ epoxy diamylate I HDDA ITMF'TA (22.51) .’ 275;) I 25p .-‘ 15p)
`25% TiO2 (Rutile)
`-
`140T
`Aluminum foil
`
`Cure:
`
`2x80 Wicm mp Hg lamp
`
`
`
`a dry rub resistance
`(mimin)
`'0' YI
`
`2% CO] 403
`+ 2% Irgacure 184
`
`_
`
`1% lrgacure 319
`+ 3 % Irgacure 184
`
`Figure 4. Comparison of photocuring efficiencies of a white screen ink using various BAPOfct-HK photoinitiators.
`
`Edition: 02.08.01, Tarrytown
`
`2001 Ciba Specialty Chemicals Corporation
`
`Page 4 of 5
`
`

`

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`Ciba Specialty Chemlcals
`Coating Effects
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`
`References
`
`2.
`
`l. U. Kolczak, G. Rist, K. Dietliker, and J. Wirz: “Reaction mechanism of monoacyl- and bisacylphosphine oxide
`photoinitiators studied by ”13-, ‘30-, and 'H-CIDNP and ESR”, J. Am. Chem. Soc, 118, 6477-6489 {1996).
`S. Jockusch, I. V. Koptyug, P. F. McGarry, G. W. Sluggett, N. J. Turro, D. M. Watkins, J. AM. Chem. Soc.,
`119,11495-11501(1997}.
`3. D. G. Leppard, M. Koehler, A. Valet: “Alkylphenylbisacylphosphine oxides and photoinitiator mixtures”, US
`Patent 6,020,528 (2000).
`E. V. Sitzmann, D. A. Wostratzky, D. A. Bramer, W. Al-Akhdar: “Impact of photoinitiators on the light cure
`response of composites”, Radtech Report, 14 (5), pp. 28-40, September/October (2000).
`
`4.
`
`Trademark
`
`Important Notice
`
`IRGACURE and DAROCUR are registered trademarks.
`
`IMPORTANT: The following supersedes Buyer’s documents. SELLER
`MAKES NO REPRESENTATION OR WARRANT, EXPRESS OR
`IMPLIED, INCLUDING OF MERCHANTABILITY OR FITNESS FOR .
`A PARTICULAR PURPOSE. No statements herein are to be construed as
`
`inducements to infringe any relevant patent. Under no circumstances shall
`Seller be liable for incidental, consequential or indirect damages for
`alleged negligence, breach of warranty, strict liability, tort or contract
`arising in connection with the product(s). Buyer’s sole remedy and Seller’s
`role liability for any claims shall be Buyer‘s purchase price. Data and
`results are based on controlled or lab work and must be confirmed by
`Buyer by testing for its intended conditions or use. The product(s) has not
`been tested for, and is therefore not recommended for, uses for which
`prolonged contact with mucous membranes, abraded skin, or blood is
`intended; or for uses for implantation within the human body is intended.
`
`Edition: 02.08.01, Tarrytown
`
`2001 Ciba Specialty Chemicals Corporation
`
`Page 5 of 5
`
`

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