KR101987946B1 - 다가 하이드록시 수지, 에폭시 수지, 그들의 제조방법, 에폭시 수지 조성물 및 그 경화물 - Google Patents

다가 하이드록시 수지, 에폭시 수지, 그들의 제조방법, 에폭시 수지 조성물 및 그 경화물 Download PDF

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Publication number: KR101987946B1
Authority: KR; South Korea
Prior art keywords: epoxy resin; polyhydric hydroxy; aralkyl; resin; hydroxy compound
Prior art date: 2012-02-23
Legal status (The legal status 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 status listed.): Active

Application number

KR1020147026281A

Other languages

English (en)

Korean (ko)

Other versions

KR20140129227A (ko

Inventor

히사시 야마다

에이지로 아오야기

케이스케 와타나베

유타카 오카자키

히데야스 아사카게

Original Assignee

닛테츠 케미컬 앤드 머티리얼 가부시키가이샤

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.)

2012-02-23

Filing date

2013-02-21

Publication date

2019-06-11

2013-02-21 Application filed by 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 filed Critical 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤

2014-11-06 Publication of KR20140129227A publication Critical patent/KR20140129227A/ko

2019-06-11 Application granted granted Critical

2019-06-11 Publication of KR101987946B1 publication Critical patent/KR101987946B1/ko

Status Active legal-status Critical Current

2033-02-21 Anticipated expiration legal-status Critical

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239000003822 epoxy resin Substances 0.000 title claims abstract description 112
229920000647 polyepoxide Polymers 0.000 title claims abstract description 112
229920005989 resin Polymers 0.000 title claims abstract description 77
239000011347 resin Substances 0.000 title claims abstract description 77
125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 64
239000000203 mixture Substances 0.000 title claims abstract description 53
238000004519 manufacturing process Methods 0.000 title claims description 10
150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 63
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 25
238000005227 gel permeation chromatography Methods 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 33
239000003795 chemical substances by application Substances 0.000 claims description 33
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
239000012435 aralkylating agent Substances 0.000 claims description 27
238000000034 method Methods 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 11
230000008569 process Effects 0.000 claims description 9
239000003377 acid catalyst Substances 0.000 claims description 8
229940126062 Compound A Drugs 0.000 claims description 7
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
150000005846 sugar alcohols Polymers 0.000 claims 1
239000000463 material Substances 0.000 abstract description 12
238000005538 encapsulation Methods 0.000 abstract description 3
239000002738 chelating agent Substances 0.000 abstract description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 42
239000000047 product Substances 0.000 description 25
150000002989 phenols Chemical class 0.000 description 20
229920003986 novolac Polymers 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 14
125000003710 aryl alkyl group Chemical group 0.000 description 13
150000001875 compounds Chemical class 0.000 description 13
239000000155 melt Substances 0.000 description 13
-1 phosphate ester Chemical class 0.000 description 13
238000002156 mixing Methods 0.000 description 10
239000004593 Epoxy Substances 0.000 description 9
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
238000005259 measurement Methods 0.000 description 8
239000004065 semiconductor Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
239000003063 flame retardant Substances 0.000 description 7
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
235000010290 biphenyl Nutrition 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000009826 distribution Methods 0.000 description 5
150000002118 epoxides Chemical class 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
238000000465 moulding Methods 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
229960001755 resorcinol Drugs 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
IXCOKTMGCRJMDR-UHFFFAOYSA-N 9h-fluorene;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 IXCOKTMGCRJMDR-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000008393 encapsulating agent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
235000013824 polyphenols Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
150000004780 naphthols Chemical class 0.000 description 3
238000003918 potentiometric titration Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
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NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 2
WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
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229940073608 benzyl chloride Drugs 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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JP6124865B2 (ja)	2017-05-10
CN104334597A (zh)	2015-02-04
KR20140129227A (ko)	2014-11-06
JPWO2013125620A1 (ja)	2015-07-30
WO2013125620A1 (ja)	2013-08-29
TWI548681B (zh)	2016-09-11
MY169844A (en)	2019-05-17
TW201345958A (zh)	2013-11-16
SG11201405075SA (en)	2014-10-30
CN104334597B (zh)	2016-06-22

Publication	Publication Date	Title
JP5320130B2 (ja)	2013-10-23	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物
JP5931234B2 (ja)	2016-06-08	エポキシ樹脂組成物の製造方法
KR102387998B1 (ko)	2022-04-18	변성 다가 하이드록시 수지, 에폭시 수지, 에폭시 수지 조성물 및 그 경화물
JP5548562B2 (ja)	2014-07-16	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物
KR101987946B1 (ko)	2019-06-11	다가 하이드록시 수지, 에폭시 수지, 그들의 제조방법, 에폭시 수지 조성물 및 그 경화물
JP6799370B2 (ja)	2020-12-16	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物
JP2017119768A (ja)	2017-07-06	多価ヒドロキシ樹脂及びエポキシ樹脂の製造方法
CN102617987A (zh)	2012-08-01	环氧树脂组合物及固化物
JP4465257B2 (ja)	2010-05-19	ナフトール樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及びその硬化物
JP5548792B2 (ja)	2014-07-16	多価ヒドロキシ樹脂、その製造方法、エポキシ樹脂組成物及びその硬化物
JP2009242658A (ja)	2009-10-22	多価ヒドロキシ化合物、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物
JP2004123859A (ja)	2004-04-22	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物
JP2004059792A (ja)	2004-02-26	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物
WO2012043414A1 (ja)	2012-04-05	エポキシ樹脂組成物及び硬化物
JP7193337B2 (ja)	2022-12-20	多価ヒドロキシ樹脂、エポキシ樹脂、エポキシ樹脂組成物及びその硬化物
JP7158228B2 (ja)	2022-10-21	多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物
JP2008231071A (ja)	2008-10-02	新規多価ヒドロキシ化合物並びにエポキシ樹脂組成物及びその硬化物
JPWO2003104295A1 (ja)	2005-10-06	アセナフチレン変性フェノール性樹脂及びエポキシ樹脂組成物

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