Sumitomo Chemical Company, Limited

Sumika Fine Chemicals, Co.,ltd.

Daiei Chemical Co., Ltd.

Sumika Fine Chemical Company, Ltd.

Daili Chemical Company, Limited

Toshio Nakamatsu

Norio Kometani

Kunihiko Imada

Yasuhiro Nishida

Yoshikazu Matsuo

Yasuyuki Suzuki

Yasuo Tezuka

Masanobu Terao

Masaki Fujiwara

Yoshitugu Egashira

Masatoshi Sakai

Naoki Harada

Yoshiaki Hayashi

Tetsuya Miyamoto

Sadaharu Abeta

Masao Nishikuri

Shinichi Watanabe

Seiji Yamada

Toshikazu Moriwaki

Ken Ishihara

Shigetoshi Muneishi

The present invention relates to a production method of 4'-bromomethyl-2-cyanobiphenyl, which includes reacting 4&#x2032;-methyl-2-cyanobiphenyl with bromine in the presence of a radical initiator and an oxidant. According to the present invention, since bromine can be regenerated by reacting hydrogen bromide, which is by-produced with the progress of bromination, with an oxidant, inhibition of bromination by hydrogen bromide, coloring by bromine and the like can be prevented. Thus, 4&#x2032;-bromomethyl-2-cyanobiphenyl useful as a starting material of pharmaceutical products can be produced industrially beneficially.

Production method of 4'-bromomethyl-2-cyanobiphenyl

2-Amino-6-chloropurine having a double cone-like crystal form.

2-amino-6-chloropurine and method for preparing the same

The present invention is directed to a method for preparing 2-amino-6-chloropurine having a double cone-like crystal form, comprising the steps of:

Double cone-like crystal form of 2-amino-6-chloropurine and preparation

A method for producing 1,4-dihydroxy-2-naphthoic acid which comprises the steps of: subjecting 1,4-dihydroxynaphthalene into an alkali metal salt formation reaction in an organic medium capable of dissolving 1,4-dihydroxynaphthalene using an alkali metal alcoholate; and subjecting the salt formation reaction mixture to carboxylation using carbon dioxide gas.

Method for producing 1,4-dihydroxy-2-naphthoic acid

An anthrapyridone compound of the following formula (I) and which is useful for coloring resins: ##STR1## wherein X.sup.1 is hydrogen, --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --SO.sub.2 R.sup.5 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.1 and R.sup.4 are each C.sub.1-4 alkyl, R.sup.2 and R.sup.3 are each hydrogen or C.sub.1-4 alkyl, R.sup.5 is C.sub.1-4 alkyl or hydroxyethyl, R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl, X.sup.2 is hydrogen or imidomethyl of the formula (II): ##STR2## wherein n is a number of 1 to 2, X.sup.4 is hydrogen or carboxylic acid C.sub.1-4 alkyl-ester, X.sup.3 is hydrogen, halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxyl, with the proviso that X.sup.1 is --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --SO.sub.2 R.sup.5 or --SO.sub.2 NR.sup.6 R.sup.7 when X.sup.2 is hydrogen, X.sup.2 is the imidomethyl of the formula (II) when X.sup.1 is the hydrogen, is provided, which is prepared by allowing an .alpha.-haloanthraquinone compound with an acylated primary aromatic amine compound in a nonaqueous medium in the presence of metallic copper or a copper compound.

Anthrapyridone compounds, their production process and their use

A method for producing 2,6-dihydroxybenzoic acid, which comprises heating an aqueous solution which contains a mixture of 2,6-dihydroxybenzoic acid and 2,4-dihydroxybenzoic acid and has a pH value of 4 or more, to selectively decompose 2,4-dihydroxybenzoic acid, and separating 2,6-dihydroxybenzoic acid from the decomposition reaction mixture.

Method for producing 2,6-dihydroxybenzoic acid

A process for producing 2-methyl-1,3-cyclohexanedione which comprises subjecting 1,3-cyclohexanedione, formaldehyde and a dialkylamine to Mannich reaction to obtain a 2-dialkylaminomethyl-1,3-cyclohexanedione, and subjecting the 2-dialkylaminomethyl to hydrogenolysis, and a process for producing 2-methylresorcinol which comprises aromatizing 2-methyl-1,3-cyclohexanedione obtained. According to these processes, it is possible to produce high-purity 2-methylresorcinol and 2-methyl-1,3-cyclohexanedione commercially easily and advantageously.

Process for producing 2-methyl-1,3-cyclohexanedione and

An anthrapyridone compound of the following formula (I), which is useful for coloring synthetic resins: ##STR1## wherein Q is --NH.sub.2, --NHCH.sub.3 or --NHCOZ where Z is phenyl or alkyl which may be substituted; X.sub.1, X.sub.2 and X.sub.3 are each hydrogen, halogen, alkyl, alkoxy, hydroxy, --NHCOR.sup.1, --CONR.sup.2 R.sup.3 m --COR.sup.4, --COOR.sup.5, --SO.sub.2 R.sup.6 or --SO.sub.2 NR.sup.7 R.sup.8 where R.sup.1 and R.sup.4 are each C.sub.1-4 alkyl, R.sup.2 and R.sup.3 are each hydrogen or C.sub.1-4 alkyl, R.sup.5 and R.sup.6 are each alkyl or hydroxyalkyl and R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-4 alkyl, with proviso that when Q is --NHCH.sub.3, X.sub.1, X.sub.2 and X.sub.3 are each hydrogen, halogen, alkoxy, hydroxy, --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --COOR.sup.5, --SO.sub.2 R.sup.6 or --SO.sub.2 NR.sup.7 R.sup.8. Process for producing the anthrapyridone compound is also provided.

Anthrapyridone compounds

A methine compound represented by the following formula and an agent containing the same for coloring resins such as polystyrene, ABS. ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group or a lower carboxylic ester group; R.sup.2 is a lower alkyl group, a lower carboxylic amide group or a lower carboxylic ester group; and X is --SO.sub.2 NR.sup.3 R.sup.4, --SO.sub.2 NCHNR.sup.5 R.sup.6 or --SO.sub.2 R.sup.7, where R.sup.3 and R.sup.4 each is a hydrogen atom, a lower alkyl group or a phenyl group, R.sup.5 and R.sup.6 each is a lower alkyl group, and R.sup.7 is a lower alkyl group or a hydroxyethyl group.

Pyrazole containing methine compounds

An anthrapyridone compound of the following formula (I) and which is useful for coloring resins: ##STR1## wherein X.sup.1 is hydrogen, --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --SO.sub.2 R.sup.5 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.1 and R.sup.4 are each C.sub.1-4 alkyl, R.sup.2 and R.sup.3 are each hydrogen or C.sub.1-4 alkyl, R.sup.5 is C.sub.1-4 alkyl or hydroxyethyl, R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl, X.sup.2 is hydrogen or imidomethyl of the formula (II): ##STR2## wherein n is a number of 1 to 2, X.sup.4 is hydrogen or carboxylic acid C.sub.1-4 alkyl-ester, X.sup.3 is hydrogen, halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxyl, with the proviso that X.sup.1 is --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --SO.sub.2 R.sup.5 or --SO.sub.2 NR.sup.6 R.sup.7 when X.sup.2 is hydrogen, X.sup.2 is the imidomethyl of the formula (II) when X.sup.1 is the hydrogen, is provided, which is prepared by allowing the .alpha.-halonathraquinone compound with an acylated primary aromatic amine compound in a nonaqueous medium in the presence of metallic copper or a copper compound.

A reactive blue dye composition, which comprises a phthalocyanine dye represented by a free acid of the following formula (I), ##STR1## wherein CuPc is a copper phthalocyanine nucleus, W is a C.sub.2 -C.sub.4 alkylene group or a 1,3- or 1,4-phenylene group having one or two sulfo groups, R.sub.1 and R.sub.2 are independently a hydrogen atom or a lower alkyl group, 1 is a number of 1 to 3, m is a number of 0 to 2, and n is a number of 1 to 3, provided that the total number of 1, m and n is 4 or less, and a phthalocyanine dye represented by a free acid of the following formula (II), ##STR2## wherein CuPc, 1, m and n are as defined above, Y.sub.1 and Y.sub.2 are independently a hydrogen atom or a methyl, methoxy or sulfo group, R.sub.3 is a hydrogen atom or a lower alkyl group, and Q is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z in which Z is a splittable group by the action of an alkali, the mixing weight ratio of the dyes (I) to (II) in terms of a copper content being from 80 through 20 to from 20 through 80, which is useful for dyeing or printing fiber materials also in a blend with other color dyes such as yellow and red dyes to give dyed or printed products of a brilliant color excellent in fastness properties with high reproducibility.

Reactive dye composition: mixture of reactive copper phthalocyanine

A water-insoluble disperse dye composition comprising a combination of a dye represented by the following formula (I), ##STR1## wherein X is hydrogen, halogen, lower alkyl or lower alkoxy, in an amount of 95 to 20% by weight, and a dye represented by the following formula (II), ##STR2## wherein Z, Y.sub.1 and Y.sub.2 are independently hydrogen or halogen, and the ring A is a benzene or naphthalene ring unsubstituted or substituted with a carboxylic acid ester group, in an amount of 5 to 80% by weight, which is useful for dyeing polyester fiber materials to obtain dyed products having both extremely high light fastness and excellent thermal resistance.

Light-fast yellow disperse dye composition for polyester

A red reactive dye represented by a free acid of the formula, ##STR1## wherein X is a hydrogen atom, a methyl, methoxy or sulfonic acid group, Y is --CH.dbd.CH.sub.2, --CH.sub.2 CH.sub.2 Y.sub.1 or --CH.sub.2 CH.sub.2 OY.sub.2 (in which Y.sub.1 is a halogen atom, and Y.sub.2 is the residue of polybasic acids), R is a C.sub.1 -C.sub.4 alkyl group, R.sub.1 and R.sub.2 are each a hydrogen atom, a methyl or ethyl group, and the azo group is located on a meta-or para-position of the benzene ring A with respect to the --NR.sub.2 -- group and the sulfonic acid group on the benzene ring A is adjacent to the azo group. This dye is suitable for dyeingcellulose fibers red to afford dyeings superior in fastnesses, acid stability, build-up property, level dyeing property and white dischargeability.

Reactive dye having both monochlorotriozinyl and vinylsulfone type

A method for dyeing polyester fiber materials is disclosed, comprising conducting combination dyeing by a combination of disperse dyes each capable of making up for the color fading of other disperse dye produced upon exposure to sunlight, by the color change thereof in hue caused upon the exposure to sunlight under the same condition.

Method for dyeing polyester fiber materials: disperse dye combinations

A turquoise blue reactive dye represented by a free acid of the formula, ##STR1## wherein [CuPc] is a copper phthalocyanine nucleus, W is ##STR2## in which R.sub.1 and R.sub.2 are each a hydrogen atom or a methyl group and i is an integer of 2 to 6 both inclusive, Y.sub.1 and Y.sub.2 are each a hydrogen atom, a methyl, methoxy or sulfonic acid group, l and m are each a number of 0 to 3, and n is a number of 1 to 3, provided that l+m+n is not more than 4. This dye is suitable for dyeing cellulose fibers to produce a turquoise blue dyed product superior in fastnesses, acid stability, build-up property, level dyeing property, and low-temperature dyeability.

Growing community of inventors

Osaka, Japan

Toshio Nakamatsu