JP2002234882A5 - - Google Patents

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JP2002234882A5
JP2002234882A5 JP2001366958A JP2001366958A JP2002234882A5 JP 2002234882 A5 JP2002234882 A5 JP 2002234882A5 JP 2001366958 A JP2001366958 A JP 2001366958A JP 2001366958 A JP2001366958 A JP 2001366958A JP 2002234882 A5 JP2002234882 A5 JP 2002234882A5
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formula
represented
producing
hydrogen atom
alcohol
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JP4116282B2 (en
JP2002234882A (en
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Priority claimed from JP2001366958A external-priority patent/JP4116282B2/en
Priority to JP2001366958A priority Critical patent/JP4116282B2/en
Priority to KR10-2003-7007625A priority patent/KR100531535B1/en
Priority to US10/433,570 priority patent/US7041838B2/en
Priority to DE60136100T priority patent/DE60136100D1/en
Priority to PCT/JP2001/010628 priority patent/WO2002046179A1/en
Priority to EP01999568A priority patent/EP1352904B1/en
Priority to TW090130267A priority patent/TW583182B/en
Publication of JP2002234882A publication Critical patent/JP2002234882A/en
Priority to US10/974,876 priority patent/US7339014B2/en
Publication of JP2002234882A5 publication Critical patent/JP2002234882A5/ja
Publication of JP4116282B2 publication Critical patent/JP4116282B2/en
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Claims (13)

下記式（１）で表される（メタ）アクリル酸エステル。
Figure 2002234882
（式（１）中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は水素原子、メチル基またはエチル基であり、Ｘ1、Ｘ2はいずれか一方が(メタ)アクリロイルオキシ基であり、もう一方が水素原子である。Ａ1、Ａ2はともに水素原子であるか、または、Ａ1とＡ2とで−Ｏ−、−ＣＨ2−または−ＣＨ2ＣＨ2−を形成している。）(Meth) acrylic acid ester represented by the following formula (1).
Figure 2002234882
 (In the formula (1), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, a methyl group or an ethyl group, and one of X 1 and X 2 is a (meth) acryloyloxy group, one of either the .A 1, a 2 is a hydrogen atom are both hydrogen atom, or, -O between a 1 and a 2 -, - CH 2 - or -CH 2 CH 2 - are formed. ) 下記式（１４）で表されるアルコール。
Figure 2002234882
（式（１４）中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は水素原子、メチル基またはエチル基であり、Ｙ1、Ｙ2はいずれか一方が水酸基であり、もう一方が水素原子である。Ａ1、Ａ2 は、Ａ 1 とＡ2とで−ＣＨ2 −を形成している。）An alcohol represented by the following formula (14) .
Figure 2002234882
 (In the formula (14) , R 1 , R 2 , R 3 and R 4 are a hydrogen atom, a methyl group or an ethyl group, and Y 1 and Y 2 are either a hydroxyl group and the other is a hydrogen atom. there .A 1, a 2 is between a 1 and a 2 - CH 2 - has a form). １，３−ジエンと無水マレイン酸とをディールス・アルダー反応させて得られる下記式（３）で表される付加生成物を還元して下記式（４）で表されるラクトンを製造し、
この式（４）で表されるラクトンを水和して下記式（２）で表されるアルコールを製造する方法。
Figure 2002234882
（式（３）中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は水素原子、メチル基またはエチル基である。Ａ1、Ａ2はともに水素原子であるか、または、Ａ1とＡ2とで−Ｏ−、−ＣＨ2−または−ＣＨ2ＣＨ2−を形成している。）
Figure 2002234882
（式（４）中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は水素原子またはメチル基である。Ａ1、Ａ2はともに水素原子であるか、または、Ａ1とＡ2とで−Ｏ−、−ＣＨ2−または−ＣＨ2ＣＨ2−を形成している。）
Figure 2002234882
 （式（２）中、Ｒ 1 、Ｒ 2 、Ｒ 3 、Ｒ 4 は水素原子、メチル基またはエチル基であり、Ｙ 1 、Ｙ 2 はいずれか一方が水酸基であり、もう一方が水素原子である。Ａ 1 、Ａ 2 はともに水素原子であるか、または、Ａ 1 とＡ 2 とで−Ｏ−、−ＣＨ 2 −または−ＣＨ 2 ＣＨ 2 −を形成している。） A lactone represented by the following formula (4) is produced by reducing an addition product represented by the following formula (3) obtained by subjecting 1,3-diene and maleic anhydride to Diels-Alder reaction;
Method for producing an alcohol represented by the following following formula (2) by hydrating a lactone of the formula (4).
Figure 2002234882
 (In the formula (3), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, a methyl group or an ethyl group. A 1 and A 2 are both hydrogen atoms, or A 1 and A 2 -O by a -, - CH 2 - or -CH 2 CH 2 - has a form).
Figure 2002234882
 (In the formula (4), R 1 , R 2 , R 3 and R 4 are hydrogen atoms or methyl groups. A 1 and A 2 are both hydrogen atoms, or A 1 and A 2 are- O—, —CH 2 — or —CH 2 CH 2 — is formed.)
Figure 2002234882
 (In the formula (2), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, a methyl group or an ethyl group, one of Y 1 and Y 2 is a hydroxyl group, and the other is a hydrogen atom. there .A 1, a 2 or are both hydrogen atom, or, -O between a 1 and a 2 -, - CH 2 - or -CH 2 CH 2 - has a form). 上記式（３）で表される付加生成物を還元する際に用いる還元剤が、金属水素化物および／または金属水素錯化合物である請求項３に記載のアルコールの製造方法。  The method for producing an alcohol according to claim 3, wherein the reducing agent used for reducing the addition product represented by the formula (3) is a metal hydride and / or a metal hydrogen complex compound. 上記式（３）で表される付加生成物を還元する際に用いる溶媒が、ジグライム、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチルピロリドンからなる群から選ばれる少なくとも１種である請求項３または４に記載のアルコールの製造方法。  The solvent used for reducing the addition product represented by the above formula (3) is at least one selected from the group consisting of diglyme, N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone. The method for producing alcohol according to claim 3 or 4. 上記式（３）で表される付加生成物を還元後、中和して上記式（４）で表されるラクトンを製造する請求項３〜５のいずれかに記載のアルコールの製造方法。After reduction the formula (3) addition product represented by the manufacturing method of alcohol according to any one of claims 3-5 for producing a lactone represented by the above following formula (4) is neutralized. 塩酸、酸性イオン交換樹脂または硫酸を用いて中和する請求項６に記載のアルコールの製造方法。  The method for producing an alcohol according to claim 6, wherein neutralization is performed using hydrochloric acid, an acidic ion exchange resin, or sulfuric acid. 上記式（４）で表されるラクトンに低級カルボン酸を付加して低級カルボン酸エステルを製造し、これを加水分解して水和する請求項３〜７のいずれかに記載のアルコールの製造方法。  The method for producing an alcohol according to any one of claims 3 to 7, wherein a lower carboxylic acid is added to the lactone represented by the formula (4) to produce a lower carboxylic acid ester, which is hydrolyzed and hydrated. . 低級カルボン酸を付加する前に、製造した上記式（４）で表されるラクトンを抽出溶媒により抽出し、得られる抽出液から上記式（４）で表されるラクトンを単離せずにそのまま低級カルボン酸を付加させる請求項８に記載のアルコールの製造方法。  Before adding the lower carboxylic acid, the lactone represented by the above formula (4) is extracted with an extraction solvent, and the lactone represented by the above formula (4) is isolated from the obtained extract without isolation. The method for producing an alcohol according to claim 8, wherein a carboxylic acid is added. 抽出溶媒が、ケトン系溶媒である請求項９に記載のアルコールの製造方法。  The method for producing an alcohol according to claim 9, wherein the extraction solvent is a ketone solvent. 低級カルボン酸付加反応に供する、抽出液中の上記式（４）で表されるラクトンの濃度が、１〜９５質量％である請求項９または１０に記載のアルコールの製造方法。  The method for producing an alcohol according to claim 9 or 10, wherein the concentration of the lactone represented by the formula (4) in the extract used for the lower carboxylic acid addition reaction is 1 to 95% by mass. 上記式（１４）で表されるアルコールを（メタ）アクリルエステル化して上記式（１）で表される（メタ）アクリル酸エステルを製造する方法。A method for producing a (meth) acrylic acid ester represented by the above formula (1) by converting the alcohol represented by the above formula (14) into a (meth) acrylic ester. 請求項３〜１１のいずれかに記載の方法により上記式（２）で表されるアルコールを製造し、
このアルコールを（メタ）アクリルエステル化して上記式（１）で表される（メタ）アクリル酸エステルを製造する方法。An alcohol represented by the above formula (2) is produced by the method according to claim 3,
A method for producing a (meth) acrylic acid ester represented by the above formula (1) by converting this alcohol into a (meth) acrylic ester.
JP2001366958A 2000-12-06 2001-11-30 Alcohol, method for producing the same, and method for producing (meth) acrylic acid ester using the alcohol Expired - Lifetime JP4116282B2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
JP2001366958A JP4116282B2 (en) 2000-12-06 2001-11-30 Alcohol, method for producing the same, and method for producing (meth) acrylic acid ester using the alcohol
KR10-2003-7007625A KR100531535B1 (en) 2000-12-06 2001-12-05 (meth)acrylate esters, starting alcohols for the preparation thereof, processes for preparing both, polymers of the esters, chemically amplifiable resist compositions, and method for forming patterns
US10/433,570 US7041838B2 (en) 2000-12-06 2001-12-05 (Meth)acrylate esters, starting alcohols for the preparation thereof, processes for preparing both, polymers of the esters, chemically amplifiable resist compositions, and method for forming patterns
DE60136100T DE60136100D1 (en) 2000-12-06 2001-12-05 (METH) ACRYLATE SITTER, ALCOHOL EXTRACT COMPOUNDS FOR THEIR PREPARATION, METHOD FOR PRODUCING THESE TWO COMPOUNDS, POLYMERS OF ESTERS, CHEMICALLY AMPLIFYABLE PROTECTION LACK COMPOSITIONS, AND METHOD FOR FORMING PATTERNS
PCT/JP2001/010628 WO2002046179A1 (en) 2000-12-06 2001-12-05 (meth)acrylate esters, starting alcohols for the preparation thereof, processes for preparing both, polymers of the esters, chemically amplifiable resist compositions, and method for forming patterns
EP01999568A EP1352904B1 (en) 2000-12-06 2001-12-05 (meth)acrylate esters, starting alcohols for the preparation thereof, processes for preparing both, polymers of the esters, chemically amplifiable resist compositions, and method for forming patterns
TW090130267A TW583182B (en) 2000-12-06 2001-12-06 (Meth)acrylic ester, its raw alcohol, its method of preparation, polymer made by polymerization of said (meth)acrylic ester, chemical amplified resist composition, and method for forming pattern
US10/974,876 US7339014B2 (en) 2000-12-06 2004-10-28 (Meth)acrylate, raw material alcohol for the (meth)acrylate, method of producing the (meth)acrylate and the alcohol, polymer produced by polymerizing the (meth)acrylate, chemically amplified resist composition, and method of the formation of a pattern

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000371712 2000-12-06
JP2000-371712 2000-12-06
JP2001366958A JP4116282B2 (en) 2000-12-06 2001-11-30 Alcohol, method for producing the same, and method for producing (meth) acrylic acid ester using the alcohol

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JP2002234882A JP2002234882A (en) 2002-08-23
JP2002234882A5 true JP2002234882A5 (en) 2005-07-21
JP4116282B2 JP4116282B2 (en) 2008-07-09

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Publication number Priority date Publication date Assignee Title
TW200502227A (en) 2003-06-12 2005-01-16 Takasago Perfumery Co Ltd Novel lactone compound
JP2006169147A (en) * 2004-12-14 2006-06-29 Daicel Chem Ind Ltd Polymerizable unsaturated carboxylic acid ester, polymer compound, resin composition for photoresist and method for producing semiconductor
EP2134725B1 (en) * 2007-04-19 2012-07-04 Merck Patent GmbH Process for preparing substituted pentacenes
US20110039210A1 (en) * 2009-05-20 2011-02-17 Rohm And Haas Electronic Materials Llc Novel resins and photoresist compositions comprising same
CN105061454B (en) * 2011-06-14 2019-09-27 三菱化学株式会社 The manufacturing method of the manufacturing method of alcoholic compound, (methyl) acrylate
JP6078526B2 (en) * 2012-02-27 2017-02-08 株式会社クラレ Acrylic acid ester derivative and method for producing the same, intermediate and method for producing the same, polymer compound, and photoresist composition
JP6090621B2 (en) * 2012-12-05 2017-03-08 三菱レイヨン株式会社 Method for producing polymerizable monomer
JP6428596B2 (en) 2015-12-25 2018-11-28 信越化学工業株式会社 Resist composition, pattern forming method, polymer compound, and monomer
JP6705286B2 (en) * 2016-05-24 2020-06-03 三菱ケミカル株式会社 Method for producing polymerizable monomer, method for producing polymer for lithography and method for producing resist composition
JP2021134152A (en) * 2020-02-25 2021-09-13 三菱ケミカル株式会社 (meth)acrylic acid ester composition
JP7439604B2 (en) 2020-03-23 2024-02-28 三菱ケミカル株式会社 Method for purifying lactone compounds

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