公开(公告)号：US20200089116A1

公开(公告)日：2020-03-19

申请号：US16616012

申请日：2018-05-28

Applicant: Central Glass Company, Limited

Inventor： Yuzuru KANEKO ,  Tsubasa ITAKURA ,  Ryo NADANO

IPC: G03F7/039 ,  G03F7/004 ,  G03F7/20

Abstract: Provided is a fluorine-containing polymer which has no perfluoroalkyl group of 4 or more carbon atoms and which, when formed together with a photoacid generator into a film, shows water repellency after film formation, but becomes hydrophilic by the action of an acid generated under light irradiation, and thus serves as a pattern forming material capable of forming a film with high sensitivity and resolution. A fluorine-containing polymer according to the present invention has a repeating unit of the formula (1) where R1 is a hydrogen atom, a fluorine atom or a C1-C10 alkyl group; R2 to R5 are each independently a hydrogen atom or a C1-C10 alkyl group; X is a single bond or a divalent group; Y is a C1-C3 fluoroalkyl or carboxylate (—COOR) group; R is a C1-C3 fluoroalkyl group; and seven or less of hydrogen atoms contained in the substituent group may be substituted with fluorine.

公开(公告)号：US20240124632A1

公开(公告)日：2024-04-18

申请号：US18266329

申请日：2021-12-02

Applicant: Central Glass Company, Limited

Inventor： Ryo NADANO ,  Satoru MIYAZAWA ,  Yuzuru KANEKO

IPC: C08F220/24 ,  C07C67/08 ,  C07C67/54 ,  C07C69/653

CPC classification number: C08F220/24 ,  C07C67/08 ,  C07C67/54 ,  C07C69/653

Abstract: Provided is a method for producing a fluorine-containing polymer with little lot-to-lot variation in weight average molecular weight. The method for producing a fluorine-containing polymer of the present invention relates to a method for producing a fluorine-containing polymer containing a repeating unit of formula (1) and a repeating unit of formula (2), which includes: fluorine-containing monomer synthesis including reacting a diol of formula (3) with at least one selected from the group consisting of unsaturated carboxylic acids, esters of the unsaturated carboxylic acids, acid halides of the unsaturated carboxylic acids, and anhydrides of the unsaturated carboxylic acids, to obtain a composition containing a fluorine-containing monomer of formula (4) as a main reaction product and a fluorine-containing monomer of formula (5) as a minor reaction product; fluorine-containing monomer purification including removing the fluorine-containing monomer of formula (5) from the composition to adjust the amount of the fluorine-containing monomer of formula (5), expressed in parts per million based on the mass of the fluorine-containing monomer of formula (4), to 1500 ppm or less; and polymerization including performing a polymerization reaction of the composition obtained after the fluorine-containing monomer purification to give the fluorine-containing polymer containing the repeating unit of formula (1) and the repeating unit of formula (2),

公开(公告)号：US20190031587A1

公开(公告)日：2019-01-31

申请号：US16071829

申请日：2016-12-01

Applicant: Central Glass Company, Limited

Inventor： Asami INAZU ,  Eri NISHIZAWA ,  Shinya AKIBA ,  Ryo NADANO

IPC: C07C45/41 ,  C07C47/14 ,  C07C41/50 ,  C07C43/317 ,  B01J31/24

CPC classification number: C07C45/41 ,  B01J31/24 ,  B01J31/2447 ,  B01J2523/821 ,  C07B61/00 ,  C07C41/50 ,  C07C43/317 ,  C07C47/14

Abstract: Disclosed is an industrial method for efficient production of an α,α-difluoroaldehyde compound, which includes reaction of an α,α-difluoroacetate with hydrogen gas (H2) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target α,α-difluoroaldehyde compound with a high conversion rate and high selectivity.

公开(公告)号：US20220081575A1

公开(公告)日：2022-03-17

申请号：US17421507

申请日：2020-01-07

Applicant: CENTRAL GLASS COMPANY, LIMITED

Inventor： Masutaka SHINMEN ,  Takuya OKADA ,  Junki YAMAMOTO ,  Ryo NADANO ,  Tatsuo MIYAZAKI

IPC: C09D7/20 ,  C07C211/03 ,  B05D1/00

Abstract: The selective film deposition method according to an embodiment of the present disclosure includes depositing a film of an organic matter represented by the following formula (1) on a substrate having a structure where a first surface region containing at least one of a metal or a metal oxide and a second surface region containing a nonmetallic inorganic material are both exposed, selectively in the first surface region than in the second surface region, wherein N represents a nitrogen atom; and R1 represents a C1-C30 hydrocarbon group optionally containing a hetero atom or a halogen atom, R2, R3, R4, and R5 each independently represent a hydrogen atom or a C1-C10 hydrocarbon group optionally containing a hetero atom or a halogen atom, where the hydrocarbon group covers a branched or cyclic hydrocarbon group when containing 3 or more carbon atoms.

公开(公告)号：US20170197899A1

公开(公告)日：2017-07-13

申请号：US15326808

申请日：2015-06-19

Applicant: Central Glass Company, Limited

Inventor： Masaaki TAKEDA ,  Shinya AKIBA ,  Ryo NADANO

IPC: C07C45/86 ,  C07C41/50

CPC classification number: C07C45/86 ,  C07C41/50 ,  C07C43/313 ,  C07C47/14

Abstract: A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a “2,2-difluoroacetaldehyde-alcohol composite system” in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the “2,2-difluoroacetaldehyde-alcohol composite system” formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

公开(公告)号：US20240043593A1

公开(公告)日：2024-02-08

申请号：US18266348

申请日：2021-12-02

Applicant: Central Glass Company, Limited

Inventor： Ryo NADANO ,  Satoru MIYAZAWA ,  Yuzuru KANEKO

IPC: C08F220/24

CPC classification number: C08F220/24

Abstract: Provided is a fluorine-containing polymer for use in a film-forming solution capable of forming a film that is less likely to leave a residue when immersed in a developer. The fluorine-containing polymer of the present invention contains a repeating unit represented by the following formula (1), and a repeating unit represented by the following formula (2) in an amount, expressed in parts per million based on a mass of the repeating unit of formula (1), of 1500 ppm or less:




wherein R1 and R2 are each independently a hydrogen atom, a methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or t-butyl group; R3 and R4 are each independently a hydrogen atom, a methyl group, or an ethyl group; R5 is a hydrogen atom or a trifluoromethyl group; and R6 is a hydrogen atom, a chlorine atom, a methyl group, or a trifluoromethyl group.

公开(公告)号：US20210317065A1

公开(公告)日：2021-10-14

申请号：US17268270

申请日：2018-09-25

Applicant: Central Glass Company, Limited

Inventor： Satoru MIYAZAWA ,  Yusuke KURAMOTO ,  Asuka SANO ,  Ryo NADANO ,  Shinya AKIBA ,  Makoto KOBAYASHI

IPC: C07C67/54 ,  C07C67/62 ,  C08F20/24

Abstract: The present invention is directed to a purification method for purifying a fluorine-containing polymerizable monomer of the formula (1), in which the fluorine-containing polymerizable monomer is purified by distillation in the coexistence of a phenolic compound A such as 6-tert-butyl-2,4-xylenol and a phenolic compound B such as 2,2′-methylene-bis(4-methyl-6-tert-butylphenol). By the combined use of the phenolic compound A and the phenolic compound B, it is possible to significantly suppress polymerization or oligomerization of the fluorine-containing polymerizable monomer even during industrial-production-scale distillation and efficiently purify the fluorine-containing polymerizable monomer by distillation.

公开(公告)号：US20150361026A1

公开(公告)日：2015-12-17

申请号：US14660401

申请日：2015-03-17

Applicant: Central Glass Company, Limited

Inventor： Hitoshi OOMURO ,  Ryo NADANO ,  Masafumi HIROTSU

IPC: C07C67/46 ,  C07C29/48 ,  C07C45/61

CPC classification number: C07C29/141 ,  C07C45/72 ,  C07C67/08 ,  C08F220/22 ,  C08F220/28 ,  C08L33/14 ,  G03F7/00 ,  G03F7/0046 ,  G03F7/0397 ,  C07C47/195 ,  C07C31/42 ,  C07C69/653 ,  C08F2220/185 ,  C08F2220/282 ,  C08F2220/1883 ,  C08K5/42

Abstract: As shown by the following reaction formula, disclosed is a fluorine-containing hydroxyaldehyde production method, including the step of obtaining a fluorine-containing hydroxyaldehyde represented by the general formula (1) by reacting a fluorine-containing ketone represented by the general formula (4) and an aldehyde represented by the general formula (5) in the presence of an organic base selected from a heterocyclic compound which contains a nitrogen atom in its ring or a tertiary amine. By this production method, it is possible to obtain the fluorine-containing hydroxyaldehyde in a high yield. Furthermore, it is possible to easily obtain in high yields a fluorine-containing propanediol, which is a derivative of this fluorine-containing hydroxyaldehyde, and a fluorine-containing alcohol monomer by using the same.

Abstract translation: 如以下反应式所示，公开了一种含氟羟醛生产方法，包括通过使由通式（4）表示的含氟酮与通式（1）表示的含氟羟基醛 ）和由通式（5）表示的醛在选自其环中含有氮原子的杂环化合物或叔胺的有机碱存在下进行。 通过该制造方法，可以高收率地得到含氟羟基醛。 此外，通过使用它们，可以高收率地容易地获得作为该含氟羟基醛的衍生物的含氟丙二醇和含氟醇单体。

公开(公告)号：US20140065541A1

公开(公告)日：2014-03-06

申请号：US14012188

申请日：2013-08-28

Applicant: Central Glass Company, Limited

Inventor： Shinya AKIBA ,  Ryo NADANO

IPC: G03F7/004

CPC classification number: G03F7/0045 ,  G03F7/0046

Abstract: A method of stabilizing a fluorine-containing acid amplifier. The method is provided to include the step of dissolving a fluorine-containing acid amplifier in an organic solvent thereby producing a solution of the fluorine-containing acid amplifier, the fluorine-containing acid amplifier being represented by general formula (1):

Abstract translation: 一种稳定含氟酸放大器的方法。 该方法包括将含氟酸放大器溶解在有机溶剂中的步骤，由此制备含氟酸放大器的溶液，所述含氟酸放大器由通式（1）表示：