TWI739976B - 含烯基之樹脂、硬化性樹脂組成物及其硬化物 - Google Patents

含烯基之樹脂、硬化性樹脂組成物及其硬化物 Download PDF

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Publication number: TWI739976B
Authority: TW; Taiwan
Prior art keywords: group; allyl; mass; alkenyl; groups
Prior art date: 2016-12-26

Application number

TW106145533A

Other languages

English (en)

Chinese (zh)

Other versions

TW201833163A (zh

Inventor

窪木健一

松浦一貴

Original Assignee

日商日本化藥股份有限公司

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2016-12-26

Filing date

2017-12-25

Publication date

2021-09-21

2017-12-25 Application filed by 日商日本化藥股份有限公司 filed Critical 日商日本化藥股份有限公司

2018-09-16 Publication of TW201833163A publication Critical patent/TW201833163A/zh

2021-09-21 Application granted granted Critical

2021-09-21 Publication of TWI739976B publication Critical patent/TWI739976B/zh

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125000003342 alkenyl group Chemical group 0.000 title claims abstract description 57
229920005989 resin Polymers 0.000 title claims abstract description 48
239000011347 resin Substances 0.000 title claims abstract description 48
239000011342 resin composition Substances 0.000 title claims abstract description 43
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 44
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims abstract description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 20
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 12
239000007870 radical polymerization initiator Substances 0.000 claims description 4
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 35
238000010521 absorption reaction Methods 0.000 abstract description 10
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 8
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
238000006243 chemical reaction Methods 0.000 description 62
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
-1 allyl ether modified phenol Chemical class 0.000 description 36
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238000010438 heat treatment Methods 0.000 description 26
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CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
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ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
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238000005481 NMR spectroscopy Methods 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
229920005672 polyolefin resin Polymers 0.000 description 1
229920001955 polyphenylene ether Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000012945 sealing adhesive Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
229910052596 spinel Inorganic materials 0.000 description 1
239000011029 spinel Substances 0.000 description 1
239000012756 surface treatment agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000001721 transfer moulding Methods 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
229960001124 trientine Drugs 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1
238000004804 winding Methods 0.000 description 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
229910052845 zircon Inorganic materials 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/32—Monomers containing two or more unsaturated aliphatic radicals
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Epoxy Resins (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Compositions Of Macromolecular Compounds (AREA)

TW106145533A 2016-12-26 2017-12-25 含烯基之樹脂、硬化性樹脂組成物及其硬化物 TWI739976B (zh)

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JP7148859B2 (ja) *	2018-08-31	2022-10-06	三菱瓦斯化学株式会社	シアン酸エステル化合物の混合物及び硬化性組成物
JP2021059651A (ja) *	2019-10-04	2021-04-15	昭和電工株式会社	硬化性樹脂組成物、その硬化物及び該硬化物を含む構造体
WO2022192317A1 (fr)	2021-03-10	2022-09-15	3D Systems, Inc.	Additifs pour matériaux de construction et articles associés imprimés en 3d

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102372835A (zh) *	2010-07-08	2012-03-14	日东电工株式会社	用于制造热固性树脂组合物的固化产物的方法和由此获得的固化产物
TW201605937A (zh) *	2014-07-01	2016-02-16	明和化成股份有限公司	烯丙醚改質聯苯基芳烷基酚醛樹脂、烯丙基改質聯苯基芳烷基酚醛樹脂、其製造方法、及使用其之組合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62207354A (ja) *	1986-03-07	1987-09-11	Sumitomo Chem Co Ltd	熱硬化性樹脂組成物
JP2780559B2 (ja) *	1991-01-25	1998-07-30	信越化学工業株式会社	アリル基又はプロペニル基を持つナフタレン誘導体
JP2570923B2 (ja) *	1991-06-07	1997-01-16	信越化学工業株式会社	熱硬化性樹脂組成物
JPH11140007A (ja) *	1997-11-12	1999-05-25	Gun Ei Chem Ind Co Ltd	プロペニル基含有ビスフェノール誘導体
JP4177685B2 (ja) *	2003-03-10	2008-11-05	住友ベークライト株式会社	潜在性フェノール樹脂の製造方法及びそれを用いるフェノール樹脂の製造方法
JP6143332B2 (ja) *	2013-02-05	2017-06-07	日本化薬株式会社	アリルエーテル樹脂およびその製造方法
US9958781B2 (en) *	2015-04-24	2018-05-01	Jsr Corporation	Method for film formation, and pattern-forming method

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Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102372835A (zh) *	2010-07-08	2012-03-14	日东电工株式会社	用于制造热固性树脂组合物的固化产物的方法和由此获得的固化产物
TW201605937A (zh) *	2014-07-01	2016-02-16	明和化成股份有限公司	烯丙醚改質聯苯基芳烷基酚醛樹脂、烯丙基改質聯苯基芳烷基酚醛樹脂、其製造方法、及使用其之組合物

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WO2018123806A1 (fr)	2018-07-05
JPWO2018123806A1 (ja)	2019-10-31
JP6963565B2 (ja)	2021-11-10
TW201833163A (zh)	2018-09-16

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