A bridged alkaline earth metal alkylphenate having reduced monomeric alkylphenol is prepared by reacting (a) a 4-alkylphenol, unsubstituted at the ortho positions, (b) an alkaline earth metal oxide or hydroxide, (c) a bridging agent comprising sulfur or a carbonyl compound of 1 to about 6, or to 4 or to 2, carbon atoms, and (d) a 2,6-dialkylphenol. The amount of the 2,6-dialkylphenol is 0.05 to 3 moles per 1 mole of the 4-alkylphenol; if there is a molar excess of the 2,6-dialkylphenol, then the excess is added after initial reaction.

A bridged alkaline earth metal alkylphenate having reduced monomeric alkylphenol is prepared by reacting (a) a 4-alkylphenol, unsubstituted at the ortho positions, (b) an alkaline earth metal oxide or hydroxide, (c) a bridging agent comprising sulfur or a carbonyl compound of 1 to about 6, or to 4 or to 2, carbon atoms, and (d) a 2,6-dialkylphenol. The amount of the 2,6-dialkylphenol is 0.05 to 3 moles per 1 mole of the 4-alkylphenol; if there is a molar excess of the 2,6-dialkylphenol, then the excess is added after initial reaction.

An additive composition includes a specific amount of α-methylstyrenated phenol, can be mixed with a main material part or curing agent part for paint, and can suppress the occurrence of a discoloration issue.

An additive composition includes a specific amount of α-methylstyrenated phenol, can be mixed with a main material part or curing agent part for paint, and can suppress the occurrence of a discoloration issue.

The present invention relates to styrenated phenol useful as a curing agent or a plasticizing agent for an epoxy resin. More particularly, it relates to use of styrenated phenol, which has viscosity and curing properties similar to those of nonylphenol and exhibits superior curing properties for an epoxy resin, as a curing agent or a plasticizing agent for an epoxy-cured paint.

The present invention relates to styrenated phenol useful as a curing agent or a plasticizing agent for an epoxy resin. More particularly, it relates to use of styrenated phenol, which has viscosity and curing properties similar to those of nonylphenol and exhibits superior curing properties for an epoxy resin, as a curing agent or a plasticizing agent for an epoxy-cured paint.

It is to provide a more stable crystal polymorph of a clathrate compound consisting of 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane and 2-phenyl-4-methyl-5-hydroxymethylimidazole (molar ratio 1:2). A novel crystal polymorph of a clathrate compound, consisting of 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane and 2-phenyl-4-methyl-5-hydroxymethylimidazole (molar ratio 1:2) and has diffraction peaks at diffraction angles (2θ) of 11.20°, 13.36°, 14.36°, 18.16°, 19.20°, 19.68°, 20.84°, 21.48°, 22.56°, 23.76° and 24.08° in a powder X-ray diffraction pattern as measured using a CuKα ray, can be obtained by, for example, further recrystallizing a crystal obtained by a conventionally known method or the like.

It is to provide a more stable crystal polymorph of a clathrate compound consisting of 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane and 2-phenyl-4-methyl-5-hydroxymethylimidazole (molar ratio 1:2). A novel crystal polymorph of a clathrate compound, consisting of 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane and 2-phenyl-4-methyl-5-hydroxymethylimidazole (molar ratio 1:2) and has diffraction peaks at diffraction angles (2θ) of 11.20°, 13.36°, 14.36°, 18.16°, 19.20°, 19.68°, 20.84°, 21.48°, 22.56°, 23.76° and 24.08° in a powder X-ray diffraction pattern as measured using a CuKα ray, can be obtained by, for example, further recrystallizing a crystal obtained by a conventionally known method or the like.

The present invention provides a photosensitive composition having excellent heat resistance, low absorbance at the exposure light at wavelengths of g-line, h-line, and i-line, and satisfactory sensitivity even when the thickness of a resist film is increased, and also provides a resist material, a coating film thereof, a novolac phenol resin suitable for these applications, and a method for producing the phenol resin. Specifically, there is provided a novolac phenol resin produced by reacting a phenolic trinuclear compound (A) with formaldehyde under an acid catalyst, the phenolic trinuclear compound (A) including a phenolic trinuclear compound (A1) produced by condensation reaction of dialkyl-substituted phenol with a hydroxyl group-containing aromatic aldehyde and a phenol trinuclear compound (A2) produced by condensation reaction of dialkyl-substituted phenol having alkyl groups at the 2- and 3-positions, 2- and 5-position, the 3- and 4-positions, or 3- and 5-positions with an aromatic aldehyde not having a hydroxyl group, wherein the molar ratio of the phenolic trinuclear compound (A1) to the phenolic trinuclear compound (A2) is 20:80 to 90:10.

The present invention provides a photosensitive composition having excellent heat resistance, low absorbance at the exposure light at wavelengths of g-line, h-line, and i-line, and satisfactory sensitivity even when the thickness of a resist film is increased, and also provides a resist material, a coating film thereof, a novolac phenol resin suitable for these applications, and a method for producing the phenol resin. Specifically, there is provided a novolac phenol resin produced by reacting a phenolic trinuclear compound (A) with formaldehyde under an acid catalyst, the phenolic trinuclear compound (A) including a phenolic trinuclear compound (A1) produced by condensation reaction of dialkyl-substituted phenol with a hydroxyl group-containing aromatic aldehyde and a phenol trinuclear compound (A2) produced by condensation reaction of dialkyl-substituted phenol having alkyl groups at the 2- and 3-positions, 2- and 5-position, the 3- and 4-positions, or 3- and 5-positions with an aromatic aldehyde not having a hydroxyl group, wherein the molar ratio of the phenolic trinuclear compound (A1) to the phenolic trinuclear compound (A2) is 20:80 to 90:10.