JPS60500626A - テトラヒドロカルビルホスホニウム塩を用いた増加した分子量を有するエポキシ樹脂の製造方法 - Google Patents

テトラヒドロカルビルホスホニウム塩を用いた増加した分子量を有するエポキシ樹脂の製造方法

Info

Publication number: JPS60500626A
Authority: JP; Japan
Prior art keywords: molecular weight; reaction; phosphonium; catalyst; epoxy resin
Prior art date: 1983-02-28
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.): Granted

Application number

JP59501231A

Other languages

English (en)

Japanese (ja)

Other versions

JPS632971B2 (2

Inventor

ドーラキアン，ジヨージ・エイ

ポール，マーシヤ・エイ

Original Assignee

ザ・ダウ・ケミカル・カンパニ−

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.)

1983-02-28

Filing date

1984-02-21

Publication date

1985-05-02

1984-02-21 Application filed by ザ・ダウ・ケミカル・カンパニ− filed Critical ザ・ダウ・ケミカル・カンパニ−

1985-05-02 Publication of JPS60500626A publication Critical patent/JPS60500626A/ja

1988-01-21 Publication of JPS632971B2 publication Critical patent/JPS632971B2/ja

Status Granted legal-status Critical Current

Links

229920000647 polyepoxide Polymers 0.000 title claims description 49
239000003822 epoxy resin Substances 0.000 title claims description 34
238000004519 manufacturing process Methods 0.000 title claims description 13
150000003839 salts Chemical class 0.000 title claims description 12
239000003054 catalyst Substances 0.000 claims description 74
238000006243 chemical reaction Methods 0.000 claims description 69
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 33
238000000034 method Methods 0.000 claims description 25
239000000376 reactant Substances 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
239000004593 Epoxy Substances 0.000 claims description 18
239000012429 reaction media Substances 0.000 claims description 16
150000004714 phosphonium salts Chemical class 0.000 claims description 12
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 claims description 10
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
150000002989 phenols Chemical class 0.000 claims description 7
230000003197 catalytic effect Effects 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
239000000463 material Substances 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
239000002826 coolant Substances 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
238000005260 corrosion Methods 0.000 claims 1
230000007797 corrosion Effects 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
230000000415 inactivating effect Effects 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
229920005989 resin Polymers 0.000 description 27
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
150000001875 compounds Chemical class 0.000 description 19
-1 amine Phosphonium halides Chemical class 0.000 description 18
150000002118 epoxides Chemical class 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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125000003118 aryl group Chemical group 0.000 description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
150000001450 anions Chemical class 0.000 description 7
239000003085 diluting agent Substances 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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239000004215 Carbon black (E152) Substances 0.000 description 2
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RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
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238000005481 NMR spectroscopy Methods 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
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239000006227 byproduct Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
230000008859 change Effects 0.000 description 2
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239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001879 gelation Methods 0.000 description 2
238000007429 general method Methods 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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125000001183 hydrocarbyl group Chemical group 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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238000002844 melting Methods 0.000 description 2
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150000002763 monocarboxylic acids Chemical class 0.000 description 2
229920003986 novolac Polymers 0.000 description 2
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
238000010926 purge Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
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238000012360 testing method Methods 0.000 description 2
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QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
125000006039 1-hexenyl group Chemical group 0.000 description 1
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
VMYCFUDPBPWPDH-UHFFFAOYSA-N 2-(2-sulfanylphenoxy)benzenethiol Chemical compound SC1=CC=CC=C1OC1=CC=CC=C1S VMYCFUDPBPWPDH-UHFFFAOYSA-N 0.000 description 1
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150000004786 2-naphthols Chemical class 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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AKTGKEBIBGSCLD-UHFFFAOYSA-N [ethyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(CC)C1=CC=CC=C1 AKTGKEBIBGSCLD-UHFFFAOYSA-N 0.000 description 1
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239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
QXILUQNMENFHOJ-UHFFFAOYSA-N tris[(3-methyloxiran-2-yl)methyl] butane-1,2,4-tricarboxylate Chemical compound CC1OC1COC(=O)CCC(C(=O)OCC1C(O1)C)CC(=O)OCC1C(C)O1 QXILUQNMENFHOJ-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008170 walnut oil Substances 0.000 description 1

Classifications

- 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
- C08G59/40—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 curing agents used
- C08G59/62—Alcohols or phenols
- 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
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)

JP59501231A 1983-02-28 1984-02-21 テトラヒドロカルビルホスホニウム塩を用いた増加した分子量を有するエポキシ樹脂の製造方法 Granted JPS60500626A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/470,107 US4438254A (en)	1983-02-28	1983-02-28	Process for producing epoxy resins
US470107		1983-02-28

Publications (2)

Publication Number	Publication Date
JPS60500626A true JPS60500626A (ja)	1985-05-02
JPS632971B2 JPS632971B2 (2)	1988-01-21

Family

ID=23866303

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59501231A Granted JPS60500626A (ja)	1983-02-28	1984-02-21	テトラヒドロカルビルホスホニウム塩を用いた増加した分子量を有するエポキシ樹脂の製造方法

Country Status (15)

Country	Link
US (1)	US4438254A (2)
EP (1)	EP0117562B1 (2)
JP (1)	JPS60500626A (2)
KR (1)	KR860000809B1 (2)
AU (1)	AU562868B2 (2)
BR (1)	BR8406168A (2)
CA (1)	CA1215194A (2)
DE (1)	DE3475717D1 (2)
ES (1)	ES8600339A1 (2)
GB (1)	GB2135674B (2)
MY (1)	MY8800004A (2)
NO (1)	NO161070C (2)
NZ (1)	NZ207301A (2)
WO (1)	WO1984003289A1 (2)
ZA (1)	ZA841476B (2)

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1983
- 1983-02-28 US US06/470,107 patent/US4438254A/en not_active Expired - Fee Related
1984
- 1984-02-21 JP JP59501231A patent/JPS60500626A/ja active Granted
- 1984-02-21 WO PCT/US1984/000239 patent/WO1984003289A1/en not_active Ceased
- 1984-02-21 BR BR8406168A patent/BR8406168A/pt not_active IP Right Cessation
- 1984-02-21 AU AU26942/84A patent/AU562868B2/en not_active Ceased
- 1984-02-28 ES ES530107A patent/ES8600339A1/es not_active Expired
- 1984-02-28 ZA ZA841476A patent/ZA841476B/xx unknown
- 1984-02-28 NZ NZ207301A patent/NZ207301A/en unknown
- 1984-02-28 DE DE8484102067T patent/DE3475717D1/de not_active Expired
- 1984-02-28 CA CA000448454A patent/CA1215194A/en not_active Expired
- 1984-02-28 GB GB08405154A patent/GB2135674B/en not_active Expired
- 1984-02-28 NO NO840748A patent/NO161070C/no unknown
- 1984-02-28 EP EP84102067A patent/EP0117562B1/en not_active Expired
- 1984-02-28 KR KR1019840000988A patent/KR860000809B1/ko not_active Expired
1988
- 1988-12-30 MY MY4/88A patent/MY8800004A/xx unknown

Also Published As

Publication number	Publication date
US4438254A (en)	1984-03-20
CA1215194A (en)	1986-12-09
ZA841476B (en)	1985-10-30
ES530107A0 (es)	1985-05-01
NO161070B (no)	1989-03-20
KR840007736A (ko)	1984-12-10
ES8600339A1 (es)	1985-05-01
NO840748L (no)	1984-08-29
NO161070C (no)	1989-06-28
MY8800004A (en)	1988-12-31
WO1984003289A1 (en)	1984-08-30
GB2135674A (en)	1984-09-05
GB8405154D0 (en)	1984-04-04
DE3475717D1 (en)	1989-01-26
EP0117562A2 (en)	1984-09-05
GB2135674B (en)	1986-08-28
AU562868B2 (en)	1987-06-18
AU2694284A (en)	1984-09-10
BR8406168A (pt)	1985-03-12
KR860000809B1 (ko)	1986-06-28
EP0117562B1 (en)	1988-12-21
JPS632971B2 (2)	1988-01-21
NZ207301A (en)	1987-10-30
EP0117562A3 (en)	1985-09-04

Publication	Publication Date	Title
JPS60500626A (ja)	1985-05-02	テトラヒドロカルビルホスホニウム塩を用いた増加した分子量を有するエポキシ樹脂の製造方法
US4302574A (en)	1981-11-24	Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
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