JP2013530294A - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JP2013530294A JP2013530294A JP2013518491A JP2013518491A JP2013530294A JP 2013530294 A JP2013530294 A JP 2013530294A JP 2013518491 A JP2013518491 A JP 2013518491A JP 2013518491 A JP2013518491 A JP 2013518491A JP 2013530294 A JP2013530294 A JP 2013530294A
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- divinylarene dioxide
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
Abstract
【選択図】なし
Description
DIPDO及びDVBDOを、それぞれ、ジイソプロペニルベンゼン(DIPB)及びジビニルベンゼン(DVB)から、Marks等によって2008年12月30日付けで出願された米国特許出願第61/141,457号、発明の名称「ジビニルアレーンジオキサイドの製造プロセス(Process for Preparing Divinylarene Dioxides)」明細書中に記載された手順を使用して製造した。
DIPB(20g、126ミリモル、Sigma-Aldrich Co.から)、3−MP(2.08g、25.3ミリモル)及びMTO(0.32g、1.26ミリモル)を、反応ケトル内で、200mLのジクロロメタン中に溶解させ、600回転/分(rpm)で攪拌した。過酸化水素(31%、54.45g、253ミリモル)を、30分間かけて滴下方式で添加し、ジャケット付きケトルを冷却することによって、温度を約25℃で保持した。得られた反応混合物を、25℃で4時間更にインキュベーションし、その後、GC分析によって、DIPBのDIPDOへの完全な転化が観察された。攪拌を停止し、得られた水相と有機相とを分離した。この有機相を、チオ硫酸ナトリウム溶液(0.25M、3倍)を使用して洗浄し、続いて水で洗浄した。次いで、この湿ったジクロロメタン溶液に硫酸ナトリウムを添加し、この混合物を約20℃〜約24℃で一晩保持した。
粘度は、約23℃で操作するStabinger SVM3000−G2粘度計を使用して測定した。
DVBDO又はDIBDO(0.20g)を、テトラヒドロフラン(5mL)中に溶解させた。蒸留水(2.00g)を添加し、この溶液を20℃の温度で4時間攪拌した。4時間のインキュベーションの後に、サンプルを滴定して、エポキシド当量重量(EEW)を決定した。EEWは、エポキシドを過剰の塩化ピリジニウムで誘導し、未使用の塩化ピリジニウムを、電位差終点決定を使用してメタノール性水酸化カリウムによって測定することによって決定した。サンプルを2回分析した。EEW値を使用して、DVBDO及びDIBDO濃度を重量%で計算した。次いで、DVBDO及びDIBDO濃度を、テトラヒドロフラン−水処理に付さなかったDVBDO及びDIBDOのものと比較した。その結果、DVBDO濃度は8%低下し、一方、DIBDO濃度は33%低下した。
Claims (14)
- (a)少なくとも1種のジビニルアレーンジオキサイド、(b)少なくとも1種のカチオン光開始剤及び(c)少なくとも1種の環状エステル化合物を含んでなる光カチオン硬化性組成物。
- 前記ジビニルアレーンジオキサイドが60%よりも大きい加水分解安定性を有する請求項1に記載の組成物。
- 前記ジビニルアレーンジオキサイドが1種又はそれ以上の、ジビニルベンゼンジオキサイド、置換されたジビニルベンゼンジオキサイド、ジビニルナフタレンジオキサイド、ジビニルビフェニルジオキサイド、ジビニルジフェニルエーテルジオキサイド及びこれらの混合物からなる群から選択される請求項1に記載の組成物。
- 前記ジビニルアレーンジオキサイドがジビニルベンゼンジオキサイドである請求項1に記載の組成物。
- 前記ジビニルアレーンジオキサイドの濃度が約1重量%〜約99重量%の範囲内であり、該少なくとも1種のカチオン光開始剤の濃度が約0.05重量%〜約20重量%の範囲内であり、そして前記環状エステル化合物の濃度が約0.95重量%〜約98.95重量%の範囲内である請求項1に記載の組成物。
- 少なくとも1種のカチオン光開始剤が、ジフェニル(フェニルチオフェニル)スルホニウムカチオン;ビス[4−(ジフェニルスルホニオ)フェニル]スルフィドビスカチオン;トリフェニルスルホニウムカチオン;ヘキサフルオロアンチモネート(SbF6 −)アニオン;SbFx(OH)y-(式中、x+y=6)アニオン;ヘキサフルオロホスフェート(PF6 −)アニオン及びこれらの混合物を含む請求項1に記載の組成物。
- 前記環状エステル化合物がラクトン又はラクチドである請求項1に記載の組成物。
- 前記環状エステル化合物がε−カプロラクトン、γ−カプロラクトン又はラクチドである請求項1に記載の組成物。
- (d)少なくとも1種の顔料物質、少なくとも1種のアルコール、少なくとも1種のポリオール、少なくとも1種の反応性希釈剤、少なくとも1種の粘度調節剤、少なくとも1種のオキセタン又はこれらの混合物を含む請求項1に記載の組成物。
- 前記少なくとも1種の顔料物質のpHが約4〜約9である請求項9に記載の組成物。
- 前記少なくとも1種の顔料物質が銅フタロシアニン青色顔料、二酸化チタン及びこれらの混合物を含む請求項9に記載の組成物。
- 前記少なくとも1種の顔料物質の濃度が約1重量%〜約80重量%の範囲内である請求項9に記載の組成物。
- (a)少なくとも1種のジビニルアレーンジオキサイド、(b)少なくとも1種のカチオン光開始剤及び(c)少なくとも1種の環状エステル化合物を混合することを含んでなる硬化性組成物の製造プロセス。
- 請求項1に記載の組成物を硬化させた硬化製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35910110P | 2010-06-28 | 2010-06-28 | |
US61/359,101 | 2010-06-28 | ||
PCT/US2011/041566 WO2012009120A2 (en) | 2010-06-28 | 2011-06-23 | Curable resin compositions |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013530294A true JP2013530294A (ja) | 2013-07-25 |
JP2013530294A5 JP2013530294A5 (ja) | 2014-08-07 |
JP5778768B2 JP5778768B2 (ja) | 2015-09-16 |
Family
ID=44628207
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013518491A Active JP5778768B2 (ja) | 2010-06-28 | 2011-06-23 | 硬化性樹脂組成物 |
Country Status (6)
Country | Link |
---|---|
US (2) | US20130090407A1 (ja) |
EP (1) | EP2585536B1 (ja) |
JP (1) | JP5778768B2 (ja) |
CN (1) | CN102985459A (ja) |
TW (1) | TWI540147B (ja) |
WO (1) | WO2012009120A2 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018513228A (ja) * | 2015-03-20 | 2018-05-24 | ブルー キューブ アイピー エルエルシー | 硬化性組成物 |
JP2018515630A (ja) * | 2015-03-20 | 2018-06-14 | ブルー キューブ アイピー エルエルシー | 硬化性組成物 |
JP2020147726A (ja) * | 2019-03-15 | 2020-09-17 | 日立化成株式会社 | エポキシ樹脂組成物、エポキシ樹脂硬化物及びエポキシ樹脂改質剤 |
JPWO2020032032A1 (ja) * | 2018-08-08 | 2021-05-20 | 旭化成株式会社 | エアバッグ用多層フィルム及びエアバッグ |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2012009120A2 (en) * | 2010-06-28 | 2012-01-19 | Dow Global Technologies Llc | Curable resin compositions |
EP2786878A1 (en) * | 2013-04-04 | 2014-10-08 | Hewlett-Packard Industrial Printing Ltd. | Methods for printing articles |
JP6568218B2 (ja) | 2014-12-23 | 2019-08-28 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | 化学線硬化型高分子混合物、硬化高分子混合物、及び関連するプロセス |
WO2017105960A1 (en) | 2015-12-17 | 2017-06-22 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
EP3532267B1 (en) | 2016-10-27 | 2023-03-01 | Bridgestone Americas Tire Operations, LLC | Processes for producing cured polymeric products by additive manufacturing |
TWI687448B (zh) * | 2016-12-09 | 2020-03-11 | 南韓商Lg化學股份有限公司 | 封裝組成物 |
SE541288C2 (en) * | 2017-12-19 | 2019-06-11 | Perstorp Ab | A hybrid photopolymer composition for additive manufacturing |
CN112074395A (zh) * | 2018-03-02 | 2020-12-11 | 福姆实验室公司 | 潜伏性固化树脂及相关方法 |
WO2021247419A1 (en) * | 2020-06-02 | 2021-12-09 | Blue Cube Ip Llc | Photo-curable resin composition for use in stereolithography |
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2011
- 2011-06-23 WO PCT/US2011/041566 patent/WO2012009120A2/en active Application Filing
- 2011-06-23 US US13/701,837 patent/US20130090407A1/en not_active Abandoned
- 2011-06-23 CN CN2011800321295A patent/CN102985459A/zh active Pending
- 2011-06-23 EP EP20110730806 patent/EP2585536B1/en not_active Not-in-force
- 2011-06-23 JP JP2013518491A patent/JP5778768B2/ja active Active
- 2011-06-27 TW TW100122395A patent/TWI540147B/zh not_active IP Right Cessation
-
2016
- 2016-02-05 US US15/017,162 patent/US20160152846A1/en not_active Abandoned
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Cited By (7)
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---|---|---|---|---|
JP2018513228A (ja) * | 2015-03-20 | 2018-05-24 | ブルー キューブ アイピー エルエルシー | 硬化性組成物 |
JP2018515630A (ja) * | 2015-03-20 | 2018-06-14 | ブルー キューブ アイピー エルエルシー | 硬化性組成物 |
JPWO2020032032A1 (ja) * | 2018-08-08 | 2021-05-20 | 旭化成株式会社 | エアバッグ用多層フィルム及びエアバッグ |
US11390242B2 (en) | 2018-08-08 | 2022-07-19 | Asahi Kasei Kabushiki Kaisha | Multilayer film for use in air bag and air bag |
JP7177839B2 (ja) | 2018-08-08 | 2022-11-24 | 旭化成株式会社 | エアバッグ用多層フィルム及びエアバッグ |
JP2020147726A (ja) * | 2019-03-15 | 2020-09-17 | 日立化成株式会社 | エポキシ樹脂組成物、エポキシ樹脂硬化物及びエポキシ樹脂改質剤 |
JP7345750B2 (ja) | 2019-03-15 | 2023-09-19 | 株式会社レゾナック | エポキシ樹脂組成物、エポキシ樹脂硬化物及びエポキシ樹脂改質剤 |
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EP2585536B1 (en) | 2015-04-29 |
WO2012009120A2 (en) | 2012-01-19 |
TW201204757A (en) | 2012-02-01 |
TWI540147B (zh) | 2016-07-01 |
WO2012009120A3 (en) | 2012-04-12 |
US20160152846A1 (en) | 2016-06-02 |
JP5778768B2 (ja) | 2015-09-16 |
US20130090407A1 (en) | 2013-04-11 |
CN102985459A (zh) | 2013-03-20 |
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