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Irgacure 184

Manufactured by BASF
Sourced in Japan, United States, Germany

IRGACURE 184 is a photoinitiator used in ultraviolet (UV) curing applications. It is a colorless to pale yellow liquid that initiates the polymerization process when exposed to UV light. The core function of IRGACURE 184 is to generate free radicals that catalyze the curing of various coatings, inks, and adhesives.

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17 protocols using irgacure 184

1

Polymerizable Pressure Sensitive Adhesive Composition

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Example 7

An acrylic pressure sensitive adhesive polymer was obtained by reacting butyl acrylate/methyl methacrylate/2-hydroxyethyl acrylate=62/10/28 (mass ratio). The acrylic pressure sensitive adhesive polymer was reacted with methacryloyl oxyethyl isocyanate to obtain a polymerizable high-molecular compound (B2) (polystyrene equivalent weight-average molecular weight=600,000) so that 80 mol of the methacryloyl oxyethyl isocyanate would react in terms of 100 mol of the 2-hydroxyethyl acrylate in the acrylic pressure sensitive adhesive polymer. A pressure sensitive adhesive composition B was obtained by mixing, in a solvent, 100 mass parts of the polymerizable high-molecular compound (B2), 3 mass parts of a photopolymerization initiator (α-hydroxycyclohexyl phenyl ketone (“IRGACURE 184” available from BASF SE)), 8 mass parts (solid content equivalent) of a cross-linker (polyvalent isocyanato compound (“BHS-8515” available from TOYOCHEM CO., LTD.), and 0.15 mass parts of a polymerizable branched polymer (B1) (“OD-007” available from Nissan Chemical Industries, Ltd., polystyrene equivalent weight-average molecular weight=14,000).

A semiconductor-related-member processing sheet was obtained by performing the same operation as in Example 6 except that the obtained pressure sensitive adhesive composition B was used as substitute for the pressure sensitive adhesive composition A.

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2

Solvent-Developable Photosensitive Composition

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Example 8

A solvent-developable photosensitive composition No. 8 was obtained by mixing 20 parts of UA-306H pentaerythritol triacrylate hexamethylene diisocyanate urethane prepolymer (binder resin, manufactured by Kyoeisha Chemical Co., Ltd.), 80 parts of KAYARAD DPCA-60 (dipentaerythritol caprolactone-modified acrylate, manufactured by Nippon Kayaku Co., Ltd.) and 5 parts of IRGACURE 184 (photoradical polymerization initiator, manufactured by BASF Ltd.).

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3

Curable Epoxy Composition Synthesis

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Example 1

Epiclon 1055 (bisphenol A type epoxy compound, epoxy equivalent weight: 450 to 500 g/eq; softening point: 64° C. to 74° C.) from DIC Corporation as a solid epoxy compound, YD-128 (liquid bisphenol A type epoxy compound, epoxy equivalent weight: 184 to 190 g/eq) from Kukdo Chemical Co., Ltd. as a liquid epoxy compound, CN110NS (bisphenol A type epoxy acrylate, liquid phase) from Sartomer as a bisphenol type (meth)acrylate, YP-50 (bisphenol A type phenoxy resin, molecular weight: 60,000 to 80,000 g/mol) as a phenoxy resin, Irgacure 184 from BASF as a photo radical initiator and CPI-101A from SAN-APRO as a photo cationic initiator were introduced into a reactor in a weight ratio of about 15:10:15:58:1:1 (Epiclon 1055:YD-128:CN110NS:YP-50:Irgacure 184:CPI-101A), diluted appropriately with methyl ethyl ketone, and then the inside of the reactor was replaced with nitrogen and homogenized to prepare a curable composition. In the case of the curable composition of Example 1, the heat treating (aging) temperature at the time of evaluating physical properties was about 50° C., and the time was about 1 hour.

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4

Synthesis of Silica Particle-Containing Compositions

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Example 20

Into light and dark brown glass bottles, 6.7 g of the PGM dispersions (15) and (16) of hydrophobic silica fine particles synthesized in Examples 15 and 16, 2.0 g of an acrylic monomer (SR351S (trimethylol propane triacrylate, manufactured by SARTOMER), SR492 (propoxylated trimethylol propane triacrylate manufactured by SARTOMER), SR444 (pentaerythritol triacrylate manufactured by SARTOMER), or KAYARD DPHA (dipentaerythritol hexaacrylate manufactured by Nippon Kayaku Co., Ltd.), 11.3 g of propylene glycol monomethyl ether, and 0.06 g of Irgacure 184 (photo radical polymerization initiator manufactured by BASF SE) were charged and stirred until the mixtures became uniform to obtain silica particle-containing compositions.

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5

Synthesis of Silica Particle-Containing Compositions

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Example 19

Into light and dark brown glass bottles, 6.7 g of the MIBK dispersions (4), (5), and (6) of hydrophobic silica fine particles synthesized in Examples 4 to 6, 2.0 g of an acrylic monomer (SR351S (trimethylol propane triacrylate, manufactured by SARTOMER), SR492 (propoxylated trimethylol propane triacrylate manufactured by SARTOMER), SR444 (pentaerythritol triacrylate manufactured by SARTOMER), or KAYARD DPHA (dipentaerythritol hexaacrylate manufactured by Nippon Kayaku Co., Ltd.), 11.3 g of methyl isobutyl ketone, and 0.06 g of Irgacure 184 (photo radical polymerization initiator manufactured by BASF SE) were charged and stirred until the mixtures became uniform to obtain silica particle-containing compositions.

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6

Synthesis of (Meth)Acrylic Polymer for UV Curing

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Example 11

The following ingredients were mixed, and the mixture was applied to have a thickness of 100 μm in such a manner that it was sandwiched between PET sheets having subjected to a mold release treatment on one side (available from Nippa Corporation, having a thickness of 50 μm) with a spacer interposed therebetween, and irradiated with ultraviolet rays at an irradiance of 3000 mJ/cm2 using a chemical lamp (FL20SBL, available from TOSHIBA CORPORATION) to obtain the (meth)acrylic polymer (11).

Isobornyl Acrylate 65 Parts by Weight

Cyclic trimethylolpropane formal acrylate (#200) 25 parts by weight

(2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl acrylate (MEDOL-10) 5 parts by weight

4-hydroxybutyl acrylate (4HBA) 5 parts by weight IRGACURE 184 (available from BASF) 0.2 parts by weight

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7

MOPS-Coated Silica Microspheres for Photocurable Applications

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Silica microspheres (5 μm, Sekisui Chemical,
Japan) and 25 × 25 × 0.5 mm silica slides (Daico MFG, Japan)
were coated with MOPS (Shin-Etsu, Japan) monolayers via siloxane (Si—O—Si)
bond formation (Scheme 1). The silica slides and microspheres were placed in boiling deionized
(DI) water to activate the hydroxyl groups on their surfaces. They
were then treated for 2 h in a solution containing MOPS in one of
a set of concentrations (0.02, 0.05, 0.1, 0.2, and 0.5 wt %) and 5
wt % HCl in ethanol, which had been stirred for 2 h in advance. The
coated slides were then washed with ethanol and dried under nitrogen.
The coated microspheres were washed and centrifuged twice in ethanol
to remove excess MOPS and were subsequently collected and suspended
in ethanol. The mixtures were ultrasonicated for 10 min for dispersion.
Prior to the placement on the XY piezo stage, 3 wt % IRGACURE 184
(1-hydroxycyclohexyl-phenylketone, BASF, Japan) was added to each
suspension as the photoinitiator. The effect of photoinitiator concentration
was evaluated, and the UV exposure time was found to reach a threshold
when an IRGACURE 184 concentration exceeding 3 wt % was used. A 30
μm thick shim ring spacer was placed on each coated slide. The
desired volume of the coated microsphere suspension was injected into
the sample case and then sealed with a glass coverslip.
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8

Formulation of UV-Curable Resin Composition

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Example 3

Amount
Component(% by weight)
CN 99119%
(aliphatic urethane resin, from Sartomer)
Alkoxylated aliphatic diacrylate13%
(SR 9209A, from Sartomer)
Vinyl pyrrolidone13%
(vinyl ester, from ISP Corporation)
Isobornyl Acrylate20.25%  
(IBOA, SR506A from Sartomer)
Stabilizer 1%
(75:25 blend of vinyl pyrrolidone:hydroqunione
monomethyl ether (MEHQ))
Slip agent1.5% 
(TEGO 450)
Photoinitiator1.75%  
(ESACURE 1 from Lamberti)
Photoinitiator 2%
2,4,6 Trimethylbenzoyl diphenyl phosphine oxide
(TPO from BASF)
Photoinitiator 2%
1-hydroxycyclohexyl phenyl ketone
(Irgacure-184 from BASF)
Fire retardant additive25%
(CEASEFIRE AC3W from Cote-L Industries)
Antimicrobial additive0.5% 
(IONPURE)

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9

Semiconductor-related-member Processing Protocol

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Example 5

A semiconductor-related-member processing sheet was obtained by performing the same operation as in Example 1 except that the composition of the pressure sensitive adhesive composition in Example 1 was changed as follows:

i) as a polymerizable high-molecular compound (B2), 100 mass parts of a reaction product obtained by reacting methacryloyl oxyethyl isocyanate with an acrylic polymer (2-ethylhexyl acrylate/vinyl acetate/2-hydroxyethyl acrylate=40/40/20 (mass ratio), polystyrene equivalent weight-average molecular weight=550,000) so that the equivalent amount of the methacryloyl oxyethyl isocyanate would be 80% to the 2-hydroxyethyl acrylate;

ii) 8.75 mass parts of an epoxy group-containing compound (“Seikaseven SS02-063” available from Dainichiseika Color & Chemicals Mfg. Co., Ltd.);

iii) as a cross-linker (C), 1 mass part of an isocyanate component (“BHS-8515” available from TOYOCHEM CO., LTD.); and

iv) 3 mass parts of a photopolymerization initiator (“IRGACURE 184” available from BASF SE).

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10

Formulation of UV-Curable Coatings

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Example 1

Amount
(% by weight)
ComponentFormula 1Formula 2
CN 99114%12.25-13.75%
(aliphatic urethane resin, from Sartomer)
Dipropylene glycol diacrylate12%9.35%  
(DPGDA, from Sartomer)
Vinyl pyrrolidone12%15.25%  
(vinyl ester, from ISP Corporation)
Isobornyl Acrylate24.24%  17%
(IBOA, SR506A from Sartomer)
Stabilizer 1% 1%
(75:25 blend of vinyl
pyrrolidone:hydroqunione
monomethyl ether (MEHQ))
Methyl methacrylate resin 3%1.9
(MB 2823 from Dianal)
Crosslinkable surface agent1.5%  1.5%*
(TEGO 2250/TEGO450*)
Photoinitiator1.75%  1.75%  
(ESACURE 1 from Lamberti)
Photoinitiator 2% 2%
2,4,6 Trimethylbenzoyl diphenyl
phosphine oxide (TPO from BASF)
Photoinitiator 3% 3%
1-hydroxycyclohexyl phenyl ketone
(Irgacure-184 from BASF)
Fire retardant additive25%25%
(CEASEFIRE AC3W from Cote-L
Industries)
Antimicrobial additive0.5% 0.5% 
(IONPURE)
Silica-based flatting agent 2.5% 
(EVONIK EXP 3600)
Solvent (Propylene Glycol Monomethyl 5%
Ether Acetate)
Fumed silica (DEGUSSA R-202)0.5-1.5%

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