CN112694599A - 苯氧基树脂及其制造方法、其树脂组合物及固化物 - Google Patents
苯氧基树脂及其制造方法、其树脂组合物及固化物 Download PDFInfo
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- CN112694599A CN112694599A CN202011142982.XA CN202011142982A CN112694599A CN 112694599 A CN112694599 A CN 112694599A CN 202011142982 A CN202011142982 A CN 202011142982A CN 112694599 A CN112694599 A CN 112694599A
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- Prior art keywords
- resin
- phenoxy resin
- compound
- functional
- phenoxy
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- 239000013034 phenoxy resin Substances 0.000 title claims abstract description 100
- 229920006287 phenoxy resin Polymers 0.000 title claims abstract description 100
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 43
- 239000011342 resin composition Substances 0.000 title claims description 47
- 239000003822 epoxy resin Substances 0.000 claims abstract description 112
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 112
- -1 phenol compound Chemical class 0.000 claims abstract description 111
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052698 phosphorus Inorganic materials 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 28
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 27
- 239000011574 phosphorus Substances 0.000 claims description 27
- 150000003003 phosphines Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 19
- 150000002989 phenols Chemical class 0.000 claims description 16
- 239000000945 filler Substances 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- 229920000877 Melamine resin Polymers 0.000 claims description 5
- 239000005011 phenolic resin Substances 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000004640 Melamine resin Substances 0.000 claims description 2
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 37
- 238000003860 storage Methods 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 78
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 54
- 239000003795 chemical substances by application Substances 0.000 description 50
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 45
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- 239000011347 resin Substances 0.000 description 43
- 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 38
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- 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 23
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229930185605 Bisphenol Natural products 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000003063 flame retardant Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
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- 239000003960 organic solvent Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
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- 238000010438 heat treatment Methods 0.000 description 12
- 238000005259 measurement Methods 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000002460 imidazoles Chemical class 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 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 8
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000005350 fused silica glass Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-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
- 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 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 229910002026 crystalline silica Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
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- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical class OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 2
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- STQYDSASXIHUJU-UHFFFAOYSA-N n-ethylethanamine;trifluoroborane Chemical compound FB(F)F.CCNCC STQYDSASXIHUJU-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
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- 239000001103 potassium chloride Substances 0.000 description 1
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- 238000004382 potting Methods 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- CIQUNISKQPOPCF-UHFFFAOYSA-N propan-2-amine;trifluoroborane Chemical compound CC(C)N.FB(F)F CIQUNISKQPOPCF-UHFFFAOYSA-N 0.000 description 1
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- 238000007788 roughening Methods 0.000 description 1
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- 239000004065 semiconductor Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 description 1
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- NGIDKLWJOPRZAI-UHFFFAOYSA-N tris(2,4-dimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC=C1P(C=1C(=CC(OC)=CC=1)OC)C1=CC=C(OC)C=C1OC NGIDKLWJOPRZAI-UHFFFAOYSA-N 0.000 description 1
- VMFMHGFERNHYIV-UHFFFAOYSA-N tris(2,5-dimethoxyphenyl)phosphane Chemical compound COC1=CC=C(OC)C(P(C=2C(=CC=C(OC)C=2)OC)C=2C(=CC=C(OC)C=2)OC)=C1 VMFMHGFERNHYIV-UHFFFAOYSA-N 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- WTQJJWGYHZEQQW-UHFFFAOYSA-N tris(2-butoxyphenyl)phosphane Chemical compound CCCCOC1=CC=CC=C1P(C=1C(=CC=CC=1)OCCCC)C1=CC=CC=C1OCCCC WTQJJWGYHZEQQW-UHFFFAOYSA-N 0.000 description 1
- HRXQUQAOBBGDQF-UHFFFAOYSA-N tris(2-butylphenyl)phosphane Chemical compound CCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCC)C1=CC=CC=C1CCCC HRXQUQAOBBGDQF-UHFFFAOYSA-N 0.000 description 1
- SOLZICGYPCFEPY-UHFFFAOYSA-N tris(2-ethoxyphenyl)phosphane Chemical compound CCOC1=CC=CC=C1P(C=1C(=CC=CC=1)OCC)C1=CC=CC=C1OCC SOLZICGYPCFEPY-UHFFFAOYSA-N 0.000 description 1
- RLRSSUBSVSBAJD-UHFFFAOYSA-N tris(2-ethylphenyl)phosphane Chemical compound CCC1=CC=CC=C1P(C=1C(=CC=CC=1)CC)C1=CC=CC=C1CC RLRSSUBSVSBAJD-UHFFFAOYSA-N 0.000 description 1
- UGFDTRRUPNEROK-UHFFFAOYSA-N tris(2-propoxyphenyl)phosphane Chemical compound CCCOC1=CC=CC=C1P(C=1C(=CC=CC=1)OCCC)C1=CC=CC=C1OCCC UGFDTRRUPNEROK-UHFFFAOYSA-N 0.000 description 1
- BWRYYJRIGUZFAT-UHFFFAOYSA-N tris(2-propylphenyl)phosphane Chemical compound CCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCC)C1=CC=CC=C1CCC BWRYYJRIGUZFAT-UHFFFAOYSA-N 0.000 description 1
- GDKAFTKCUOBEDW-UHFFFAOYSA-N tris(2-tert-butylphenyl)phosphane Chemical compound CC(C)(C)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C GDKAFTKCUOBEDW-UHFFFAOYSA-N 0.000 description 1
- XRALRSQLQXKXKP-UHFFFAOYSA-N tris(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 XRALRSQLQXKXKP-UHFFFAOYSA-N 0.000 description 1
- BCULEPSBDKFQBD-UHFFFAOYSA-N tris[2-[(2-methylpropan-2-yl)oxy]phenyl]phosphane Chemical compound CC(C)(C)OC1=CC=CC=C1P(C=1C(=CC=CC=1)OC(C)(C)C)C1=CC=CC=C1OC(C)(C)C BCULEPSBDKFQBD-UHFFFAOYSA-N 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 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
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
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Abstract
本发明提供一种反应可以充分进行、且得到的苯氧基树脂与其它材料的贮藏稳定性优良的苯氧基树脂的制造方法、以及通过该制造方法得到的苯氧基树脂、苯氧基树脂组合物以及固化物。在本发明的苯氧基树脂的制造方法中,使2官能环氧树脂与2官能酚类化合物在下述式(1)表示的膦类的存在下反应,(R1为碳数为1~4的烷基或碳数为1~4的烷氧基,R2为氢原子、碳数为1~4的烷基或碳数为1~4的烷氧基。)
Description
技术领域
本发明涉及反应活性优良、得到的苯氧基树脂与其它成分、特别是固化剂混合时的贮藏稳定性优良的苯氧基树脂的制造方法,和通过该制造方法得到的苯氧基树脂。另外,本发明涉及使用该苯氧基树脂得到的树脂组合物及固化物。
背景技术
环氧树脂由于耐热性、粘接性、耐化学药品性、耐水性、机械强度及电特性等优良,因此被广泛应用于涂料、土木、粘接、电气材料用途等领域。而且,通过用各种方法进行高分子量化,赋予了制膜性。该高分子量化了的环氧树脂被称为苯氧基树脂。特别是双酚A型的苯氧基树脂,主要是在作为涂料用清漆的基础树脂、膜成型用的基础树脂、或添加到环氧树脂清漆中调整流动性或制成固化物时用于韧性改良、粘接性改良的目的。另外,骨架中具有磷原子或溴原子的被用作环氧树脂组合物或热塑性树脂中配合的阻燃剂。
作为苯氧基树脂的制造方法,一般已知有在碱的存在下,使二官能酚类化合物与表卤醇反应的“一段法”;和使二官能环氧树脂与二官能酚类化合物在催化剂的存在下反应的“二段法”等。与一段法相比,二段法几乎不产生食盐等副产物,因此,已知二段法是适合制造合成后难以精制的苯氧基树脂的方法。非专利文献1中记载了通常使用鎓盐系化合物、碱性化合物类等作为利用二段法制造苯氧基树脂时的催化剂。
将苯氧基树脂用于上述那样的涂料、土木、粘接、电气材料等领域时,主要作为基础树脂使用,因此通常作为与以环氧树脂和固化剂为代表的多种材料的混合物使用。根据本发明人等的详细研究,在用二段法制造时,使用上述非专利文献1中记载那样的鎓盐系化合物、碱性化合物类作为催化剂的苯氧基树脂有时在与其它材料混合时的贮藏稳定性变得不充分。另外,非专利文献1中也记载了作为磷系化合物使用三苯基膦作为催化剂的情况,但三苯基膦作为二段法的催化剂活性不充分。
现有技术文献
非专利文献
非专利文献1:总说环氧树脂第1卷基础篇I环氧树脂技术协会(2003)
发明内容
发明所要解决的课题
本发明的课题在于提供一种苯氧基树脂的制造方法,在该制造方法中,在使2官能环氧树脂与2官能酚类化合物用二段法反应时,反应可以充分地进行,且得到的苯氧基树脂与其它材料配合时的贮藏稳定性优良。另外,本发明的目的还在于提供使用该制造方法得到的苯氧基树脂、含有该苯氧基树脂的苯氧基树脂组合物及固化物。
用于解决课题的手段
本发明人等为了解决上述课题而进行了深入研究,结果发现,使用2官能环氧树脂和2官能酚类化合物作为原料来获得苯氧基树脂时,通过使用特定的膦类作为催化剂,能够解决上述课题,从而完成了发明。
即,本发明是一种苯氧基树脂的制造方法,其特征在于,其是使2官能环氧树脂与2官能酚类化合物在催化剂的存在下反应的重均分子量(Mw)为10000~150000的苯氧基树脂的制造方法,其中,所述催化剂是下述式(1)表示的膦类,
式(1)中,R1分别独立地为碳数为1~4的烷基或碳数为1~4的烷氧基,R2分别独立地为氢原子、碳数为1~4的烷基或碳数为1~4的烷氧基。
相对于上述2官能环氧树脂1.0摩尔,优选使用上述2官能酚类化合物0.95~1.05摩尔,上述膦类的使用量优选为2官能环氧树脂和2官能酚类化合物的合计使用量的0.001~5质量%。
上述2官能环氧树脂的一部分或全部、上述2官能酚类化合物的一部分或全部、或者两者优选为分子内含有芴环的含芴环化合物。
上述2官能环氧树脂的一部分或全部、上述2官能酚类化合物的一部分或全部、或者两者优选为分子内含有磷的含磷化合物,得到的苯氧基树脂的磷含有率优选为1~6质量%。
得到的苯氧基树脂的环氧当量优选为4000~200000g/eq.。
另外,本发明是一种苯氧基树脂,其特征在于,其是通过上述制造方法而得到的。
另外,本发明是一种苯氧基树脂,其特征在于,其是Mw为10000~150000的苯氧基树脂,并且含有0.001~5质量%的上述式(1)表示的膦类。
另外,本发明是一种树脂组合物,其是通过在上述苯氧基树脂中配合固化成分而形成的。
上述固化成分优选为选自环氧树脂、丙烯酸酯树脂、三聚氰胺树脂、尿素树脂、酚醛树脂、酸酐化合物、胺系化合物、咪唑系化合物、酰胺系化合物、阳离子聚合引发剂、有机膦类、聚异氰酸酯化合物及封端异氰酸酯化合物中的至少一种。
优选进一步配合有填充材料。
另外,本发明是一种固化物,其是通过将上述树脂组合物固化而形成的。
发明效果
本发明的制造方法具有充分的反应速度。另外,本发明的苯氧基树脂在配合了其它成分、特别是固化剂时的贮藏稳定性优良。由此,通过本发明的苯氧基树脂的制造方法得到的苯氧基树脂及配合了它的树脂组合物能够适合地用于涂料、电气电子材料、粘接剂、碳纤维强化树脂(CFRP)等领域。另外,根据用途,有时也必须使苯氧基树脂固化。此时,由于反应溶剂回收时所花费的热过程,有时会引起不必要的聚合等,因此一般要进行残留催化剂的除去或不活泼化。但是,在本发明的制造方法中,几乎不发生残留催化剂引起的这种聚合等反应,因此不需要除去残留催化剂,在成本上也有利。
具体实施方式
本发明的苯氧基树脂的制造方法中,使2官能环氧树脂和2官能酚类化合物在上述式(1)表示的膦类的存在下反应。另外,在本说明书中,有时将本发明的苯氧基树脂的制造方法称为“本发明的制造方法”。另外,有时将通过本发明的制造方法得到的苯氧基树脂称为本发明的苯氧基树脂。
本发明的苯氧基树脂在与其它成分、特别是固化剂配合时,发挥贮藏稳定性显著优良的效果。另外,本发明中使用的膦类与三苯基膦相比,二段法中的活性更高,因此反应时间变短。这被认为是因为在上述膦类的苯基的邻位有一个取代基的缘故。如果2个邻位双方都有取代基,则二段法中的活性变得过高,因此反应会变得更短,但同时贮藏稳定性也会恶化。
本发明的制造方法中使用的2官能环氧树脂只要是分子内具有2个环氧基的环氧树脂即可。上述的2官能环氧树脂可以仅使用一种,也可以组合多种使用。
作为2官能环氧树脂,可以列举出例如双酚A二缩水甘油醚、双酚F二缩水甘油醚、双酚E二缩水甘油醚、双酚Z二缩水甘油醚、双酚S二缩水甘油醚、双酚AD二缩水甘油醚、双酚苯乙酮二缩水甘油醚、双酚三甲基环己烷二缩水甘油醚、双酚芴二缩水甘油醚(例如ZX-1201(日铁化学和材料株式会社制)等)、双甲酚芴二缩水甘油醚、四甲基双酚A二缩水甘油醚、四甲基双酚F二缩水甘油醚、四叔丁基双酚A二缩水甘油醚、四甲基双酚S二缩水甘油醚、二羟基二苯基醚二缩水甘油醚、硫代二酚二缩水甘油醚、四溴双酚A二缩水甘油醚等双酚型环氧树脂;联苯酚二缩水甘油醚、四甲基联苯酚二缩水甘油醚、二甲基联苯酚二缩水甘油醚、四叔丁基联苯酚二缩水甘油醚等联苯酚型环氧树脂;对苯二酚二缩水甘油醚、甲基对苯二酚二缩水甘油醚、二丁基对苯二酚二缩水甘油醚、间苯二酚二缩水甘油醚、甲基间苯二酚二缩水甘油醚等苯二酚型环氧树脂;以及二羟基蒽二缩水甘油醚、氢蒽对苯二酚二缩水甘油醚、二羟基萘二缩水甘油醚、双萘酚芴二缩水甘油醚、二苯基二环戊二烯型环氧树脂等。
作为2官能环氧树脂,还可以列举出在上述2官能环氧树脂的芳香环上加成了氢的2官能环氧树脂;由己二酸、琥珀酸、邻苯二甲酸、四氢邻苯二甲酸、甲基六氢邻苯二甲酸、对苯二甲酸、间苯二甲酸、邻苯二甲酸、联苯二羧酸、二聚酸等各种二羧酸类与表卤醇制造的缩水甘油酯型环氧树脂;由苯胺等胺化合物与表卤醇制造的缩水甘油胺型环氧树脂;乙二醇二缩水甘油醚、聚乙二醇二缩水甘油醚、丙二醇二缩水甘油醚、聚丙二醇二缩水甘油醚、1,4-丁烷二醇二缩水甘油醚、聚四亚甲基二醇二缩水甘油醚、1,5-戊二醇二缩水甘油醚、聚五亚甲基二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、聚六亚甲基二醇二缩水甘油醚、1,7-庚二醇二缩水甘油醚、聚七亚甲基二醇二缩水甘油醚、1,8-辛二醇二缩水甘油醚、1,10-癸二醇二缩水甘油醚、2,2-二甲基-1,3-丙二醇二缩水甘油醚等仅由链状结构构成的(聚)烷二醇型环氧树脂;1,4-环己烷二甲醇二缩水甘油醚等具有环状结构的亚烷基二醇型环氧树脂;脂肪族环状环氧树脂;以及含磷2官能环氧树脂(例如FX-305(日铁化学和材料株式会社制)、二苯基膦酰氢醌二缩水甘油醚等)等。
为了提高苯氧基树脂的耐热性,优选二羟基萘二缩水甘油醚、双酚芴二缩水甘油醚、双甲酚芴二缩水甘油醚、双萘酚芴二缩水甘油醚,更优选双酚芴二缩水甘油醚、双甲酚芴二缩水甘油醚、双萘酚芴二缩水甘油醚等具有芴环结构的2官能环氧树脂。为了赋予阻燃性,优选四溴双酚A二缩水甘油醚、含磷2官能环氧树脂,更优选含磷2官能环氧树脂。
作为本发明的制造方法中使用的2官能酚类化合物,只要是具有2个以上与芳香环键合的羟基的化合物即可。上述2官能酚类化合物可以仅使用1种,也可以组合多种使用。
作为2官能酚类化合物,可以列举出例如双酚A、双酚F、双酚E、双酚Z、双酚S、双酚AD、双酚苯乙酮、双酚三甲基环己烷、双酚芴、双甲酚芴、四甲基双酚A、四甲基双酚F、四叔丁基双酚A、四甲基双酚S、二羟基二苯基醚、二羟基二苯基甲烷、双(羟基苯氧基)苯、硫代二酚、二羟基芪等双酚类;联苯酚、四甲基联苯酚、二甲基联苯酚、四叔丁基联苯酚等联苯酚类;对苯二酚、甲基对苯二酚、二丁基对苯二酚、间苯二酚、甲基间苯二酚等苯二酚类;以及二羟基蒽、二羟基萘、二氢蒽对苯二酚类等。
为了提高苯氧基树脂的耐热性,优选二羟基萘、双酚芴、双甲酚芴,更优选双酚芴、双甲酚芴。
相对于2官能环氧树脂1.00摩尔,2官能酚类化合物的使用量优选为0.9~1.1摩尔,更优选为0.95~1.05摩尔,进一步优选为0.96~1.00摩尔,特别优选为0.97~0.99摩尔。如果2官能酚类化合物的配合量在该范围内,则得到的苯氧基树脂的分子量充分伸长,因此优选。另外,从反应性方面考虑,优选末端基团中存在较多环氧基,因此2官能酚类化合物的配合量优选小于1.00摩尔。
另外,为了赋予耐热性,优选使用具有芴环结构的2官能环氧树脂作为上述2官能环氧树脂的一部分或全部,使用具有芴环结构的2官能酚类化合物作为上述2官能酚类化合物的一部分或全部。
作为具有芴环结构的2官能酚类化合物,具体而言可以列举出9,9-双(4-羟基苯基)芴、9,9-双(4-羟基-2-甲基苯基)芴、9,9-双(4-羟基-3-甲基苯基)芴、9,9-双(4-羟基-3-乙基苯基)芴、9,9-双(3-羟基-6-甲基苯基)芴、9,9-双(2-羟基-4-甲基苯基)芴、9,9-双(4-羟基-3-叔丁基苯基)芴、9,9-双(4-羟基-3,5-二甲基苯基)芴、9,9-双(4-羟基-2,6-二甲基苯基)芴、9,9-双(4-羟基-3,5-二叔丁基苯基)芴、9,9-双(4-羟基-3-环己基苯基)芴、9,9-双(4-羟基-3-苯基苯基)芴等9,9-双(羟基苯基)芴类;以及9,9-双(2-羟基-6-萘基)芴、9,9-双(1-羟基-5-萘基)芴等9,9-双(羟基萘基)芴类等。上述的含芴环结构的酚类化合物可以使用一种,也可以并用两种以上。
作为具有芴环结构的2官能环氧树脂,可以列举出通过使具有上述芴环结构的2官能酚类化合物和5~20倍摩尔的表氯醇等表卤代醇在使用氢氧化钠或氢氧化钾等碱催化剂的条件下反应而得到的二缩水甘油基化合物。具体而言,可以列举出上述环氧树脂、双酚芴二缩水甘油醚、双甲酚芴二缩水甘油醚、双萘酚芴二缩水甘油醚等。
另外,为了赋予阻燃性,作为上述2官能酚类化合物的一部分或全部,还可以使用加成了卤素的2官能的卤代酚化合物(例如四溴双酚A等)、或2官能的含磷酚化合物,从环境方面考虑,优选2官能的含磷酚化合物。
另外,为了赋予阻燃性,作为上述2官能酚类化合物或2官能环氧树脂的一部分或全部,优选使用含磷化合物。
作为2官能的含磷酚化合物,可以列举出例如10-(2,5-二羟基苯基)-10H-9-氧杂-10-磷杂菲-10-氧化物、10-(2,7-二羟基-1-萘基)-10H-9-氧杂-10-磷杂菲-10-氧化物、10-(1,4-二羟基-2-萘基)-10H-9-氧杂-10-磷杂菲-10-氧化物、10-(2,5-二羟基苯基)-8-苄基-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物、10-(2,7-二羟基-1-萘基)-8-苄基-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物、二苯基膦酰基对苯二酚、二苯基膦酰基-1,4-二羟基萘,1,4-环辛烯膦酰基-1,4-苯二酚、1,5-环辛烯膦酰基-1,4-苯二酚等。上述的含磷酚化合物可以使用一种,也可以并用两种以上。
作为2官能环氧树脂的含磷化合物,可以列举出使用碱催化剂使上述含磷酚化合物和5~20倍摩尔的表卤醇反应而得到的二缩水甘油基化合物。具体而言,可以列举出上述环氧树脂、FX-305、二苯基膦酰基对苯二酚二缩水甘油醚等。
使用2官能的含磷酚化合物得到的苯氧基树脂的磷含有率根据使用目的适当调整即可,优选为1~6质量%,更优选为2~5质量%,进一步优选为3~4.5质量%。
本发明的制造方法中使用的上述膦类是作为2官能环氧树脂与2官能酚类化合物反应的催化剂而起作用的。
在本发明的制造方法中用作催化剂的膦类由上述式(1)表示。在式(1)中,处于邻位的取代基R1是必须的。另外,在与其位置不同的邻位上没有取代基也是必须的。
R1是碳数为1~4的烷基或碳数为1~4的烷氧基。作为碳数为1~4的烷基,可以是直链状、支链状的任一种,例如可以列举出甲基、乙基、丙基、异丙基、正丁基、叔丁基等。作为碳数为1~4的烷氧基,可以是直链状、支链状的任一种,例如可以列举出甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基等。作为R1,优选甲基、乙基、叔丁基或甲氧基,更优选甲基或甲氧基,进一步优选甲氧基。
R2是位于间位和/或对位的取代基或氢原子,作为取代基,是碳数为1~4的烷基或碳数为1~4的烷氧基。作为取代基的R2,例示出与R1同样的基团,优选的取代基也同样。取代基的数量为0、1、2或3,优选为0或1。
作为上述式(1)表示的膦类,只要是邻位有1个取代基的苯基在磷原子上键合了3个的结构即可,该苯基可以三个都相同,也可以不同。
作为式(1)所示的膦类,可以列举出例如三(邻甲苯基)膦、三(邻乙苯基)膦、三(邻丙苯基)膦、三(邻正丁基苯基)膦、三(邻叔丁基苯基)膦、三(2,4-二甲基苯基)膦、三(2,5-二甲基苯基)膦、三(邻甲氧基苯基)膦、三(邻乙氧基苯基)膦、三(邻丙氧基苯基)膦、三(邻正丁氧基苯基)膦、三(邻叔丁氧基苯基)膦、三(2,4-二甲氧基苯基)膦、三(2,5-二甲氧基苯基)膦等。上述的膦类中,优选三(邻甲苯基)膦、三(2,4-二甲基苯基)膦、三(2,5-二甲基苯基)膦或三(邻甲氧基苯基)膦。上述的膦类可以仅使用一种,也可以组合多种使用。
上述膦类的使用量相对于2官能环氧树脂和2官能酚类化合物的总量100质量份优选为0.001~5质量份,更优选为0.005~2质量份,进一步优选为0.01~1质量份,特别优选为0.01~0.5质量份。如果使用的上述膦类的配合量少,则苯氧基树脂的分子量有可能不能充分变大。另外,如果配合量多,则贮藏稳定性容易恶化,需要在反应后除去,因此不优选。如果膦类的使用量在范围内,则反应时苯氧基树脂的分子量容易足够大,贮藏稳定性也容易变好,所以优选。另外,上述催化剂可以在反应开始时一并加入,也可以根据反应经时适时分开加入。
上述膦类可以用有机溶剂或水稀释后使用。作为有机溶剂,只要是溶解原料的溶剂,任何溶剂都可以。具体而言,可以列举出与后述的本发明的苯氧基树脂反应时可以使用的有机溶剂相同的溶剂。
上述2官能环氧树脂与上述2官能酚类化合物的反应也可以在常压、加压、减压中的任一条件下进行。在所用催化剂不分解的程度的温度范围内进行。反应温度过高时,生成的苯氧基树脂可能会劣化,反应温度过低时,反应可能无法进行,无法达到目标分子量。因此,反应温度优选为50~240℃,更优选为80~230℃,进一步优选为100~220℃,特别优选为120~200℃。反应时间没有特别限定,优选为0.5~24小时,更优选为1~20小时,进一步优选为2~12小时,特别优选为3~10小时。如果反应时间在优选范围内,则在提高生产效率方面、可以削减未反应成分方面都是优选的。另外,使用丙酮或甲基乙基酮这样的低沸点溶剂时,通过使用高压釜在高压下进行反应,可以确保反应温度。另外,需要除去反应热时,通常是通过利用反应热的使用溶剂的蒸发-冷凝-回流法、间接冷却法或它们的并用来进行。
在本发明的制造方法中,反应时可以使用溶剂。作为溶剂,只要是溶解原料和反应产物(苯氧基树脂),对反应没有不良影响的溶剂,则任何溶剂都可以,但通常是有机溶剂。作为有机溶剂,例如可以列举出芳香族系溶剂、酮系溶剂、酯系溶剂、醚系溶剂、酰胺系溶剂、二醇醚系溶剂等。这些溶剂可以单独使用,也可以两种以上混合使用。使用溶剂的量可以根据反应条件适当选择,但作为固体成分浓度优选为35~95质量%。另外,在反应中产生高粘性产物的情况下,也可以在反应中途再加入溶剂后继续反应。
作为芳香族系溶剂,例如可以列举出苯、甲苯、二甲苯等。
作为酮系溶剂,例如可以列举出丙酮、甲基乙基酮、甲基异丁基酮、2-庚酮、4-庚酮、2-辛酮、环戊酮、环己酮、乙酰丙酮等。作为酯系溶剂,例如可以列举出乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙酸苄酯、丙酸乙酯、丁酸乙酯、丁酸丁酯、戊内酯、丁内酯等。作为醚系溶剂,例如可列举出二乙基醚、二丁基醚、叔丁基甲基醚、四氢呋喃(THF)、二恶烷等。作为酰胺系溶剂,例如可以列举出甲酰胺、N-甲基甲酰胺、N,N-二甲基甲酰胺(DMF)、乙酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、2-吡咯烷酮、N-甲基吡咯烷酮等。
作为二醇醚系溶剂,例如可以列举出乙二醇单甲醚、乙二醇单乙醚、乙二醇单正丁基醚、乙二醇二甲醚、乙二醇单乙醚乙酸酯、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单正丁基醚、二乙二醇二甲醚、二乙二醇单乙醚乙酸酯、丙二醇单甲醚、丙二醇单正丁基醚、丙二醇二甲醚、丙二醇单甲醚乙酸酯、二丙二醇二甲醚等。
反应结束后,溶剂可以根据需要通过蒸馏等除去,也可以进一步追加以调整固体成分浓度。作为其溶剂,只要是溶解苯氧基树脂的溶剂,任何溶剂都可以,但通常是有机溶剂。作为有机溶剂,可以列举出与上述有机溶剂相同的有机溶剂。
在本发明的制造方法中,在反应时不会使贮藏稳定性恶化的范围内,也可以与上述膦类一起并用其它催化剂。作为其它催化剂,只要是通常用作二段法的催化剂的物质,就没有特别限制。例如可以列举出碱金属化合物、上述膦类以外的有机磷化合物、叔胺类、季铵盐、环状胺类、咪唑类等。上述的其它催化剂可以仅使用一种,也可以组合使用两种以上。另外,从贮藏稳定性的观点出发,优选在保管树脂组合物时等不含有其它催化剂,或者设定为比上述膦类更少量的配合量。
作为碱金属化合物,可以列举出例如氢氧化钠、氢氧化锂、氢氧化钾等碱金属氢氧化物;碳酸钠、碳酸氢钠、氯化钠、氯化锂、氯化钾等碱金属盐;甲醇钠、乙醇钠等碱金属醇盐;碱金属酚盐、氢化钠、氢化锂等碱金属的氢化物;乙酸钠、硬脂酸钠等有机酸的碱金属盐等。
作为上述膦类以外有机磷化合物,可以列举出例如四甲基溴化鏻、四甲基碘化鏻、四甲基氢氧化鏻、三甲基环己基氯化鏻、三甲基环己基溴化鏻、三甲基苄基氯化鏻、三甲基苄基溴化鏻、四苯基溴化鏻、三苯基甲基溴化鏻、三苯基甲基碘化鏻、三苯基乙基氯化鏻、三苯基乙基溴化鏻、三苯基乙基碘化鏻、三苯基苄基氯化鏻、三苯基苄基溴化鏻等。另外,上述式(1)表示的膦类以外的膦类也有可能残留在作为反应产物的苯氧基树脂中,因此当以不含有它的苯氧基树脂为目标时,不优选其并用。
作为叔胺类,例如可以列举出三乙基胺、三正丙基胺、三正丁基胺、三乙醇胺、苄基二甲基胺等。
作为季铵盐,例如可以列举出四甲基氯化铵、四甲基溴化铵、四甲基氢氧化铵、三乙基甲基氯化铵、四乙基氯化铵、四乙基溴化铵、四乙基碘化铵、四丙基溴化铵、四丙基氢氧化铵、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵、苄基三甲基氯化铵、苄基三甲基溴化铵、苄基三甲基氢氧化铵、苄基三丁基氯化铵、苯基三甲基氯化铵等。
作为环状胺类,例如可以列举出1,8-二氮杂双环(5,4,0)-7-十一烯、1,5-二氮杂双环(4,3,0)-5-壬烯等。
作为咪唑类,例如可以列举出2-甲基咪唑、2-乙基咪唑、2-苯基咪唑、2-十一烷基咪唑、2-乙基-4-甲基咪唑、1-氰基乙基-2-甲基咪唑等。
通过本发明的制造方法得到的苯氧基树脂的Mw优选为10000~150000,更优选为20000~100000,进一步优选为25000~80000,特别优选为30000~60000。Mw低者薄膜制膜性和伸长性差,Mw过高时,树脂的处理性显著恶化。这里,Mw是通过GPC的测定来决定的,GPC的测定方法按照实施例中记载的条件。
该苯氧基树脂的环氧当量(g/eq.)优选为4000~200000,更优选为6000~150000,进一步优选为8000~100000,特别优选为10000~50000。环氧当量在优选的范围内时,苯氧基树脂的分子量足够大,从挠性的观点出发是优选的。
本发明的苯氧基树脂是用本发明的制造方法得到的苯氧基树脂,这是有利的。有利的是含有0.001~5质量%的上述式(1)表示的膦类。本发明的苯氧基树脂的优选Mw和环氧当量与用本发明的制造方法得到的苯氧基树脂相同。
本发明的苯氧基树脂中存在的上述式(1)表示的膦类优选为0.01~2质量%,更优选为0.05~1质量%。膦类过多时,与固化剂配合时的贮藏稳定性可能会恶化。如果设定为低于0.001质量%,则对苯氧基树脂的制造中的反应或未反应物等杂质的除去会产生负担。该膦类的量可以用高效液相色谱法(HPLC)来定量。另外,测定方法按照实施例中记载的条件。
本发明的苯氧基树脂本身是具有挠性的热塑性树脂,也可以单独使用,但也可以配合固化成分制成热固性的树脂组合物。
固化成分可以列举出能够单独固化的热固化树脂、能够与苯氧基树脂的羟基或环氧基等反应而固化的树脂或固化剂、与固化剂一起使用而固化的树脂等。
作为固化成分,例如可以列举出环氧树脂、丙烯酸酯树脂、酚醛树脂、三聚氰胺树脂、尿素树脂、不饱和聚酯树脂、醇酸树脂、热固性聚酰亚胺树脂、酸酐化合物、聚异氰酸酯化合物、及封端异氰酸酯化合物等。其中优选环氧树脂、酚醛树脂、三聚氰胺树脂、酸酐化合物、聚异氰酸酯化合物或封端异氰酸酯化合物,更优选2官能以上的环氧树脂、环氧树脂用固化剂及固化促进剂。上述的固化成分可以单独使用,也可以并用两种以上。
固化成分例如可以列举出用固化剂使环氧树脂固化的树脂组合物、用自由基聚合引发剂使丙烯酸酯树脂固化的树脂组合物、酚醛树脂、使三聚氰胺树脂等在热作用下自聚合的树脂成分等、以及酸酐化合物、聚异氰酸酯化合物、封端异氰酸酯化合物等与苯氧基树脂的2级醇性羟基进行加成聚合的化合物。
固化成分的配合量以苯氧基树脂/固化成分(质量比)计优选为1/99~99/1,更优选为10/90~90/10,进一步优选为25/75~75/25。通过配合固化成分,可以得到耐热性更优异的材料。
当固化成分为环氧树脂时,可以使用以往公知的环氧树脂。另外,环氧树脂是指具有至少1个环氧基的环氧树脂,但优选具有2个以上环氧基的环氧树脂,更优选具有3个以上环氧基的环氧树脂。具体而言,可以列举出聚缩水甘油醚化合物、聚缩水甘油胺化合物、聚缩水甘油酯化合物、脂环式环氧化合物、其它改性环氧树脂等。上述的环氧树脂可以单独使用,也可以并用2种以上同一类的环氧树脂,另外,也可以组合使用不同类的环氧树脂。
作为聚缩水甘油醚化合物,例如可以列举出能够作为苯氧基树脂的原料使用的上述2官能环氧树脂、苯酚酚醛清漆型环氧树脂、甲酚酚醛清漆型环氧树脂、烷基酚醛清漆型环氧树脂、苯乙烯化苯酚酚醛清漆型环氧树脂、双酚酚醛清漆型环氧树脂、萘酚酚醛清漆型环氧树脂、β-萘酚芳烷基型环氧树脂、萘二酚芳烷基型环氧树脂、α-萘酚芳烷基型环氧树脂、联苯基芳烷基酚型环氧树脂、三羟基苯基甲烷型环氧树脂、四羟基苯基乙烷型环氧树脂、二环戊二烯型环氧树脂等多官能酚醛清漆型环氧树脂、以及亚烷基二醇型环氧树脂、脂肪族环状环氧树脂等。
作为聚缩水甘油胺化合物,例如可以列举出二氨基二苯基甲烷型环氧树脂、间苯二胺型环氧树脂、1,3-双氨基甲基环己烷型环氧树脂、异氰脲酸酯型环氧树脂、苯胺型环氧树脂、乙内酰脲型环氧树脂、氨基苯酚型环氧树脂等。
作为聚缩水甘油酯化合物,例如可以列举出二聚酸型环氧树脂、六氢邻苯二甲酸型环氧树脂、偏苯三酸型环氧树脂等。
作为脂环式环氧化合物,可以列举出セロキサイド2021(ダイセル化学工业株式会社制)等脂肪族环状环氧树脂等。
作为其它改性环氧树脂,例如可以列举出氨基甲酸酯改性环氧树脂、含恶唑啉酮环的环氧树脂、环氧改性聚丁二烯橡胶衍生物、羧基末端丁二烯腈橡胶(CTBN)改性环氧树脂、聚乙烯基芳烃聚氧化物(例如二乙烯基苯二氧化物、三乙烯基萘三氧化物等)等。
配合环氧树脂时,也可以含有固化剂。固化剂是有助于环氧树脂的环氧基间的交联反应和/或链增长反应的物质。固化剂的配合量相对于环氧树脂100质量份,根据需要使用0.1~100质量份,优选1~80质量份,更优选5~60质量份,进一步优选10~60质量份。
作为固化剂,没有特别限制,一般作为环氧树脂用固化剂而已知的固化剂全部均可使用。从提高耐热性的观点出发,作为优选的固化剂,可以列举出酚系固化剂、酰胺系固化剂和咪唑类。另外,从降低吸水性的观点出发,作为优选的固化剂,可以列举出活性酯系固化剂。此外还可以列举出胺系固化剂、酸酐系固化剂、有机膦类、鏻盐、苯并化合物、四苯基硼盐、有机酸二酰肼、卤化硼胺络合物、聚硫醇系固化剂、异氰酸酯系固化剂、封端异氰酸酯系固化剂等。上述的固化剂可以单独使用,也可以并用两种以上的同种类,还可以组合使用其它种类。
作为酚系固化剂,例如可以列举出能够作为苯氧基树脂的原料使用的上述2官能酚类化合物、苯酚酚醛清漆、双酚A酚醛清漆、甲酚酚醛清漆、二甲苯酚醛清漆、三羟基苯基甲烷酚醛清漆、二环戊二烯苯酚、萘酚酚醛清漆、苯乙烯化苯酚酚醛清漆、萜烯酚、重油改性苯酚、苯酚芳烷基、萘酚芳烷基、聚羟基苯乙烯、氟代甘氨醇、邻苯三酚、叔丁基邻苯三酚、苯三醇、三羟基萘、三羟基二苯甲酮、三羟基苯乙酮等3价以上的酚化合物、和上述含磷酚化合物。也可以将使茚或苯乙烯与上述酚类化合物反应而得到的物质用作固化剂。酚系固化剂以固化剂中的活性羟基相对于环氧树脂中的环氧基的摩尔比计优选在0.8~1.5的范围内使用。
作为酰胺系固化剂,例如可以列举出二氰二酰胺及其衍生物、聚酰胺树脂等。酰胺系固化剂相对于全部环氧树脂成分100质量份优选在0.1~25质量份的范围内使用。
作为咪唑类,只要是具有咪唑骨架的化合物即可,没有特别限定。例如可以列举出2-苯基咪唑、2-乙基-4-甲基咪唑、2-苯基-4-甲基咪唑、1-苄基-2-甲基咪唑、1-苄基-2-苯基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基-2-苯基咪唑、1-氰基乙基-2-十一烷基咪唑偏苯三酸酯、1-氰基乙基-2-苯基咪唑鎓偏苯三酸酯、2,4-二氨基-6-[2’-甲基咪唑鎓基-(1’)]-乙基-均三嗪、2,4-二氨基-6-[2’-乙基-4’-甲基咪唑鎓基-(1’)]-乙基-均三嗪、2,4-二氨基-6-[2’-甲基咪唑鎓基-(1’)]-乙基-均三嗪异氰脲酸加成物、2-苯基咪唑异氰脲酸加成物、2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟甲基咪唑、以及环氧树脂与上述咪唑类的加成物等。咪唑类优选相对于全部环氧树脂成分100质量份在0.1~25质量份的范围内使用。另外,咪唑类由于具有催化能力,因此一般也被分类为后述的固化促进剂。
作为活性酯系固化剂,优选酚酯类、苯硫吩酯类、N-羟基胺酯类、杂环羟基化合物的酯类等在1分子中具有2个以上的反应活性高的酯基的化合物,其中,更优选使日本特许5152445号公报中记载的那样的多官能酚类化合物与芳香族羧酸类反应而得到的酚酯类。作为羧酸化合物,例如可以列举出苯甲酸、乙酸、琥珀酸、马来酸、衣康酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、均苯四酸等。作为具有酚性羟基的芳香族化合物,例如可以列举出邻苯二酚、二羟基萘、二羟基二苯甲酮、三羟基二苯甲酮、四羟基二苯甲酮、间苯三酚、苯三醇、二环戊二烯基二苯酚、苯酚酚醛清漆等。市售品有EPICLON HPC-8000-65T(DIC株式会社制)等,但不限于这些。活性酯系固化剂优选以固化剂中的活性酯基相对于树脂组合物中的环氧基的摩尔比计在0.2~2.0的范围内使用。
作为胺系固化剂,例如可以列举出二亚乙基三胺、三亚乙基四胺、间苯二胺、异佛尔酮二胺、二氨基二苯基甲烷、二氨基二苯基砜、二氨基二苯基醚、苄基二甲基胺、2,4,6-三(二甲基氨基甲基)苯酚、双氰胺、作为二聚酸等酸类与多胺类的缩合物的聚酰胺胺等胺系化合物等。胺系固化剂以固化剂中的活性氢基相对于树脂组合物中的环氧基的摩尔比计优选在0.5~1.5的范围内使用。
作为酸酐系固化剂,例如可以列举出甲基四氢邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、均苯四酸酐、邻苯二甲酸酐、偏苯三酸酐、甲基纳迪克酸酐、马来酸酐等。酸酐系固化剂以固化剂中的酸酐基相对于树脂组合物中的环氧基的摩尔比计优选在0.5~1.5的范围内使用。
另外,活性氢基是指具有与环氧基有反应性的活性氢的官能团(包括具有通过水解等产生活性氢的潜在性活性氢的官能团、和显示同等的固化作用的官能团),具体而言,可以列举出酸酐基、羧基、氨基、酚性羟基等。另外,关于活性氢基,羧基(-COOH)和酚性羟基(-OH)计算为1摩尔,氨基(-NH2)计算为2摩尔。另外,当活性氢基不明确时,可以通过测定而求出活性氢当量。例如,通过使苯基缩水甘油醚等环氧当量已知的单环氧树脂与活性氢当量未知的固化剂反应,并测定消耗的单环氧树脂的量,可以求出使用的固化剂的活性氢当量。
另外,配合环氧树脂时,根据需要,可以使用固化促进剂。作为固化促进剂,例如可以列举出咪唑类、叔胺类、膦类、金属化合物、胺络合盐等。上述固化促进剂可以单独使用,也可以并用两种以上。
作为咪唑类、叔胺类和膦类,例如可以列举出与本发明的制造方法中可以使用的上述催化剂相同的物质。
作为金属化合物,例如可以列举出辛酸锡等。
作为胺络合盐,例如可以列举出三氟化硼单乙基胺络合物、三氟化硼二乙基胺络合物、三氟化硼异丙基胺络合物、三氟化硼氯苯基胺络合物、三氟化硼苄基胺络合物、三氟化硼苯胺络合物、或它们的混合物等三氟化硼络合物类等。
固化促进剂的配合量根据使用目的适当选择即可,相对于树脂组合物中的环氧树脂成分100质量份,根据需要使用0.01~15质量份,优选0.01~10质量份,更优选0.05~8质量份,进一步优选0.1~5质量份。通过使用固化促进剂,可以降低固化温度和缩短固化时间。
在用自由基聚合引发剂使作为固化成分的丙烯酸酯树脂固化的树脂组合物中,可以列举出(甲基)丙烯酸酯系化合物的热固性树脂组合物或光固化性树脂组合物。(甲基)丙烯酸酯系化合物是作为粘度调整或固化成分而使用的分子中具有至少一个以上的(甲基)丙烯酰基的丙烯酸酯。(甲基)丙烯酸酯系化合物的一部分优选具有2个以上的(甲基)丙烯酰基。此时的树脂组合物以(甲基)丙烯酸酯系化合物和热聚合引发剂、光聚合引发剂、或这两者为必须成分。
作为上述的(甲基)丙烯酸酯系化合物,可以列举出单官能(甲基)丙烯酸酯、多官能(甲基)丙烯酸酯、氨基甲基酯(甲基)丙烯酸酯、环氧丙烯酸酯等。上述的(甲基)丙烯酸酯系化合物可以单独使用,也可以并用两种以上。
作为单官能(甲基)丙烯酸酯,例如可以列举出(甲基)丙烯酸异冰片酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸二环戊烯氧基乙酯、(甲基)丙烯酸二环戊基酯、丙烯酰吗啉、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸4-羟基丁酯、聚乙二醇单(甲基)丙烯酸酯、聚丙二醇单(甲基)丙烯酸酯、环己烷-1,4-二甲醇单(甲基)丙烯酸酯、(甲基)丙烯酸四氢呋喃酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸苯基聚乙氧基酯、(甲基)丙烯酸2-羟基-3-苯氧基丙基酯、邻苯基苯酚单乙氧基(甲基)丙烯酸酯、邻苯基苯酚聚乙氧基(甲基)丙烯酸酯、对枯基苯氧基乙基(甲基)丙烯酸酯、(甲基)丙烯酸异冰片酯、三溴苯氧基乙基(甲基)丙烯酸酯、(甲基)丙烯酸二环戊基酯、(甲基)丙烯酸二环戊烯基酯、(甲基)丙烯酸二环戊烯氧基乙酯等。
作为多官能(甲基)丙烯酸酯,例如可以列举出1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、双酚A聚乙氧基二(甲基)丙烯酸酯、双酚A聚丙氧基二(甲基)丙烯酸酯、双酚F聚乙氧基二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、三羟甲基丙烷三氧乙基(甲基)丙烯酸酯、三(2-羟基乙基)异氰脲酸酯三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、三(丙烯酰氧基乙基)异氰脲酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、三季戊四醇六(甲基)丙烯酸酯、三季戊四醇五(甲基)丙烯酸酯、羟基新戊酸新戊二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基丙烷聚乙氧基三(甲基)丙烯酸酯、二(三羟甲基)丙烷四(甲基)丙烯酸酯、环己烷二甲醇(甲基)丙烯酸酯及二羟甲基三环癸烷二(甲基)丙烯酸酯等。
另外,氨基甲酸酯(甲基)丙烯酸酯可以通过使聚异氰酸酯化合物与多元醇化合物反应,再与(甲基)丙烯酸酯反应而得到。环氧丙烯酸酯可以通过环氧化合物与(甲基)丙烯酸酯的反应而得到。
作为可以作为(甲基)丙烯酸酯系化合物的聚合引发剂使用的化合物,只要是通过加热或活性能量射线光的照射等手段产生自由基的化合物,就可以没有特别限定地使用。
作为聚合引发剂,例如通过加热使其固化时,偶氮二异丁腈、过氧化苯甲酰等偶氮系、过氧化物系引发剂等通常的自由基热聚合中能够使用的聚合引发剂均可使用。
另外,在通过光自由基聚合进行自由基聚合的情况下,苯偶姻类、苯乙酮类、蒽醌类、噻吨酮类、缩酮类、二苯甲酮类、氧化膦类等通常的光自由基聚合中能够使用的聚合引发剂均可使用。
上述的聚合光引发剂可以单独使用,也可以作为2种以上的混合物使用。进而,对于光自由基聚合引发剂,也可以与叔胺类化合物、N,N-二甲基氨基苯甲酸乙基酯等促进剂等组合使用。
作为聚异氰酸酯化合物,例如可以列举出甲苯二异氰酸酯、甲基环己烷二异氰酸酯、二苯基甲烷二异氰酸酯、二环己基甲烷二异氰酸酯、异佛尔酮二异氰酸酯、六亚甲基二异氰酸酯、苯二甲基二异氰酸酯、氢化苯二甲基二异氰酸酯、二聚酸二异氰酸酯、三甲基六亚甲基二异氰酸酯、赖氨酸三异氰酸酯等。进而,还可以列举出上述聚异氰酸酯化合物的3~5聚体等、以及上述聚异氰酸酯化合物与至少具有2个氨基、羟基、羧基等活性氢原子的化合物的反应物等。
作为酸酐化合物,例如可以列举出邻苯二甲酸酐、六氢邻苯二甲酸酐、偏苯三酸酐、马来酸酐、甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、均苯四酸酐、甲基纳迪克酸酐、十二烯基琥珀酸酐、氯菌酸酐、苯四羧酸酐、二苯甲酮四羧酸二酐、亚乙基双(偏苯三酸酐)、甲基环己烯基四羧酸二酐等。进而,还可以列举出上述酸酐化合物和不饱和化合物的缩合物等。
另外,在本发明的树脂组合物中,作为粘度调整用,可以使用有机溶剂或反应性稀释剂。这些有机溶剂或反应性稀释剂可以单独使用,也可以混合两种以上。
作为有机溶剂,例如可以列举出与在本发明的制造方法中能够使用的上述有机溶剂相同的有机溶剂。另外,除此之外,还可以列举出甲醇、乙醇、1-甲氧基-2-丙醇、2-乙基-1-己醇、苄基醇、乙二醇、丙二醇、丁二醇、松油等醇类;二甲基亚砜等亚砜类;和己烷、环己烷等链烷烃类等。
作为反应性稀释剂,例如可以列举出烯丙基缩水甘油醚、丁基缩水甘油醚、2-乙基己基缩水甘油醚、苯基缩水甘油醚、甲苯基缩水甘油醚等单官能缩水甘油醚类;间苯二酚二缩水甘油醚、新戊二醇二缩水甘油醚、1,4-丁二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、环己烷二甲醇二缩水甘油醚、丙二醇二缩水甘油醚等二官能缩水甘油醚类;甘油聚缩水甘油醚、三羟甲基丙烷聚缩水甘油醚、三羟甲基乙烷聚缩水甘油醚、季戊四醇聚缩水甘油醚等多官能缩水甘油醚类;新癸酸缩水甘油酯等缩水甘油酯类;和苯基二缩水甘油胺、甲苯基二缩水甘油胺等缩水甘油胺类。
上述的有机溶剂或反应性稀释剂优选作为不挥发成分以90质量%以下使用,其适当的种类和使用量根据用途适当选择。例如,在印制电路布线板用途中,优选甲基乙基酮、丙酮、1-甲氧基-2-丙醇等沸点为160℃以下的极性溶剂,其使用量以不挥发成分计优选为40~80质量%。另外,在粘接膜用途中,优选使用例如酮类、乙酸酯类、卡必醇类、芳香族烃类、二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮等,其使用量以不挥发成分计优选为30~60质量%。
为了提高所得固化物的耐冲击性等物性,在不降低可靠性的范围内,本发明的树脂组合物中还可以使用公知的填充材料。
作为填充材料,例如可以列举出熔融二氧化硅、结晶二氧化硅、氧化铝、氮化硅、氮化硼、氮化铝、氢氧化铝、氢氧化钙、氢氧化镁、勃姆石、滑石、云母、粘土、碳酸钙、碳酸镁、碳酸钡、氧化锌、氧化钛、氧化镁、硅酸镁、硅酸钙、硅酸锆、硫酸钡、碳等填充材料;碳纤维、玻璃纤维、氧化铝纤维、二氧化硅氧化铝纤维、碳化硅纤维、聚酯纤维、纤维素纤维、芳族聚酰胺纤维、陶瓷纤维等纤维状填充材料、以及微粒橡胶等。
其中,优选不会因固化物的表面粗化处理中使用的高锰酸盐的水溶液等氧化性化合物而分解或溶解的物质,特别是熔融二氧化硅和结晶二氧化硅容易得到微细的粒子,因此优选。另外,在特别增大填充材料的配合量的情况下,优选使用熔融二氧化硅。熔融二氧化硅可以使用破碎状、球状中的任一种,但为了提高熔融二氧化硅的配合量并抑制成型材料的熔融粘度的上升,更优选主要使用球状的物质。进而为了提高球状二氧化硅的配合量,优选适当调整球状二氧化硅的粒度分布。
另外,填充材料也可以进行硅烷偶联剂处理和硬脂酸等有机酸处理。通常作为使用填充材料的理由,可以列举出固化物的耐冲击性的提高效果和固化物的低线膨胀性化。
在作为阻燃助剂发挥作用以提高阻燃性的情况下,优选氢氧化铝、勃姆石、氢氧化镁等金属氢氧化物。在提高热传导性的情况下,优选氧化铝、氮化硅、氮化硼、氮化铝、熔融二氧化硅、晶体二氧化硅,更优选氧化铝、氮化硼、熔融二氧化硅、晶体二氧化硅。用于导电糊剂等用途时,可以使用银粉或铜粉等导电性填充材料。
考虑到固化物的低线膨胀性化和阻燃性,填充材料的配合量优选较高。相对于树脂组合物中的总固体成分,优选为1~98质量%,更优选为3~90质量%,进一步优选为5~80质量%,特别优选为10~60质量%。如果配合量多,则作为层叠板用途所需的粘接性有可能下降,进而固化物变脆,有可能得不到充分的机械物性。另外,配合量少时,有可能无法得到固化物的耐冲击性提高等填充材料的配合效果。
另外,填充材料的粒径过大时,固化物中容易残留空隙,过小时,容易凝聚,分散性变差。平均粒径(D50)优选为0.01~5μm,更优选为0.05~1.5μm,进一步优选为0.1~1μm。填充材料的平均粒径在该范围内时,可以良好地保持树脂组合物的流动性。另外,平均粒径可以通过粒度分布测定装置测定。
另外,为了提高所得固化物的阻燃性,在不降低可靠性的范围内,本发明的树脂组合物中还可以使用公知的各种阻燃剂。作为可以使用的阻燃剂,例如可以列举出卤素系阻燃剂、磷系阻燃剂、氮系阻燃剂、硅酮系阻燃剂、无机系阻燃剂、有机金属盐系阻燃剂等。从对环境的观点出发,优选不含卤素的阻燃剂,特别优选磷系阻燃剂。这些阻燃剂可以单独使用,也可以并用2种以上的同一类的阻燃剂,另外,也可以组合使用不同类的阻燃剂。
另外,在本发明的树脂组合物中,根据需要,在不损害特性的范围内,可以配合其它添加剂。作为其它添加剂,例如可以列举出热塑性树脂、偶联剂、紫外线吸收剂、抗氧化剂、脱模剂、消泡剂、乳化剂、触变性赋予剂、平滑剂、涂布不匀防止剂、增塑剂、颜料、颜料分散剂等。
作为热塑性树脂,例如可以列举出本发明以外的苯氧基树脂、聚氨酯树脂、聚酯树脂、聚乙烯树脂、聚丙烯树脂、聚苯乙烯树脂、ABS树脂、AS树脂、氯乙烯树脂、聚醋酸乙烯酯树脂、聚甲基丙烯酸甲酯树脂、聚碳酸酯树脂、聚缩醛树脂、环状聚烯烃树脂、聚酰胺树脂、热塑性聚酰亚胺树脂、聚酰胺酰亚胺树脂、聚四氟乙烯树脂、聚醚酰亚胺树脂、聚苯醚树脂、改性聚苯醚树脂、聚醚砜树脂、聚砜树脂、聚醚醚酮树脂、聚苯硫醚树脂、聚乙烯醇缩甲醛树脂等。从相容性方面考虑,优选本发明以外的苯氧基树脂,从低介电特性方面考虑,优选聚苯醚树脂或改性聚苯醚树脂。
本发明的树脂组合物中也可以配合偶联剂。通过配合偶联剂,可以提高与基材的粘接性和基体树脂与无机填料的粘接性。作为偶联剂,可以列举出硅烷偶联剂、钛酸酯偶联剂等。这些偶联剂可以单独使用,也可以并用2种以上。
另外,偶联剂的配合量相对于树脂组合物中的总固体成分优选设定为0.1~2.0质量%左右。如果偶联剂的配合量过少,则不能充分得到配合偶联剂带来的提高基体树脂与无机填料的密合性的效果。另一方面,偶联剂的配合量过多时,偶联剂有可能从得到的固化物中渗出。
作为硅烷偶联剂,例如可以列举出γ-环氧丙氧基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷等环氧硅烷偶联剂;γ-氨基丙基三乙氧基硅烷、N-β(氨基乙基)γ-氨基丙基三甲氧基硅烷、N-β(氨基乙基)γ-氨基丙基甲基二甲氧基硅烷、γ-氨基丙基三甲氧基硅烷、γ-脲基丙基三乙氧基硅烷等氨基硅烷偶联剂;3-巯基丙基三甲氧基硅烷等巯基硅烷偶联剂;对苯乙烯基三甲氧基硅烷、乙烯基三氯硅烷、乙烯基三(β-甲氧基乙氧基)硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷等乙烯基硅烷偶联剂;以及环氧系、氨基系、乙烯基系的高分子类型的硅烷等。
作为钛酸酯偶联剂,例如可以列举出异丙基三异硬脂酰钛酸酯、异丙基三(N-氨基乙基-氨基乙基)钛酸酯、二异丙基双(磷酸二辛酯)钛酸酯、四异丙基双(亚磷酸二辛酯)钛酸酯、四辛基双(二(十三烷基)亚磷酸酯)钛酸酯、四(2,2-二烯丙氧基甲基-1-丁基)双(二(十三烷基))亚磷酸酯钛酸酯、双(焦磷酸二辛酯)氧乙酸酯钛酸酯、双(焦磷酸二辛酯)亚乙基钛酸酯等。
另外,作为颜料,可以列举出喹吖啶酮系、偶氮系、酞菁系等有机颜料;以及氧化钛、金属箔状颜料、防锈颜料等无机颜料。作为紫外线吸收剂,可以列举出受阻胺系、苯并三唑系、二苯甲酮系等。作为抗氧化剂,可以列举出受阻酚系、磷系、硫系、酰肼系等。作为脱模剂,可以列举出硬脂酸、棕榈酸、硬脂酸锌、硬脂酸钙等。相对于树脂组合物中的总固体成分,上述的其它添加剂的配合量优选为0.01~20质量%的范围。
本发明的树脂组合物是通过均匀混合上述各成分而得到的。苯氧基树脂、固化成分、进而根据需要配合了各种添加剂的树脂组合物可以用与以往已知的方法同样的方法容易地制成固化物。作为固化物,可以列举出层叠物、浇铸物、成型物、粘接层、绝缘层、薄膜等成型固化物。作为用于得到固化物的方法,可以采用与公知的树脂组合物同样的方法,优选使用浇铸、注入、灌封、浸渍、滴涂、传递成型、压缩成型等或制成树脂片材、带有树脂的铜箔、预浸料等的形态并层叠然后通过加热加压固化而制成层叠板等方法。树脂组合物的固化方法根据树脂组合物中的配合成分和配合量而不同,但通常固化温度为80~300℃,固化时间为10~360分钟。该加热优选在80~180℃下进行10~90分钟的一次加热和在120~200℃下进行60~150分钟的二次加热这种二段处理。另外,在玻璃化转变温度(Tg)超过二次加热的温度的配合体系中,优选进而在150~280℃下进行60~120分钟的三次加热。通过进行上述的二次加热、三次加热,可以减少固化不良。制作树脂片材、带有树脂的铜箔、预浸料等树脂半固化物时,通常通过加热等使树脂组合物的固化反应进行到能够保持形状的程度。当树脂组合物含有溶剂时,通常通过加热、减压、风干等方法除去大部分溶剂,但也可以在树脂半固化物中残留5质量%以下的溶剂。
本发明的苯氧基树脂或配合了其它成分、特别是固化成分的本发明的树脂组合物具有优良的贮藏稳定性。因此,可以适用于本发明的树脂组合物、涂料、电气电子材料、密封材料、浇铸材料、碳纤维强化树脂、导电糊剂、粘接剂、绝缘材料等各种领域,特别是作为电气电子领域中的绝缘浇铸模、层叠材料、密封材料等是有用的。作为用途的一个例子,可以列举出印制电路布线基板、柔性布线基板、电容器等电气电子电路用层叠板、带有树脂的金属箔、膜状粘接剂、液状粘接剂等粘接剂、半导体密封材料、底部填充材料、3D-LSI用芯片间填料(inter chip fill)、电路基板用绝缘材料、绝缘片材、预浸料、放热基板、抗蚀油墨,但并不限定于它们。
实施例
以下,根据实施例和比较例更具体地说明本发明,但本发明只要不超过其主旨,就不限定于这些。只要没有特别说明,“份”就表示质量份,“%”表示质量%。分析方法、测定方法如下所示。
(1)环氧当量:根据JIS K 7236标准进行测定,单位用“g/eq.”表示。具体而言,使用电位差滴定装置,作为溶剂使用环己酮,加入溴化四乙基铵乙酸溶液,使用0.1mol/L高氯酸-乙酸溶液。另外,溶剂稀释品(树脂清漆)由不挥发成分计算出作为固体成分换算值的数值。
(2)不挥发成分:根据JIS K 7235标准进行测定。干燥温度为200℃,干燥时间设为60分钟。
(3)磷含有率:向试样中加入硫酸、盐酸、高氯酸,加热进行湿式灰化,将所有磷原子作为正磷酸。在硫酸酸性溶液中使偏钒酸盐和钼酸盐反应,测定产生的磷钒钼酸络合物在420nm处的吸光度,用%表示根据预先制作的标准曲线求出的磷含有率。
(4.1)重均分子量(Mw):通过GPC测定求出。具体而言,使用在主体(东曹株式会社制造、HLC-8220GPC)上串联具备色谱柱(东曹株式会社制造、TSKgel G4000HXL、TSKgelG3000HXL、TSKgel G2000HXL)的测定仪,柱温设定为40℃。另外,洗脱液使用THF,流速设定为1mL/分钟,检测器使用差示折射率检测器。测定试样使用将固体成分0.05g溶解于10mL的THF中,并用0.45μm的微型过滤器过滤后的物质50μL。根据由标准单分散聚苯乙烯(东曹株式会社制造、A-500、A-1000、A-2500、A-5000、F-1、F-2、F-4、F-10、F-20、F-40、F-80、F-128)求出的标准曲线来换算,求出MW。另外,数据处理使用了东曹株式会社制造的GPC-8020型号II版本6.00。另外,含磷苯氧基树脂的情况下,使用了下述(4.2)的测定方法。
(4.2)重均分子量(Mw):通过GPC测定求出。具体而言,使用在主体(东曹株式会社制造,HLC-8320GPC)上串联具备柱(东曹株式会社制造,TSKgel SuperH-H、SuperH2000、SuperHM-H、SuperHM-H)的结构,柱温设定为40℃。另外,洗脱液使用DMF(含20mm溴化锂产品),流速为0.3mL/分钟,检测器使用差示折射率检测器。测定试样使用将固体成分0.1g溶解于10mL的DMF中,并用0.45μm的微型过滤器过滤后的物质20μL。根据由标准聚环氧乙烷(东曹株式会社制造、SE-2、SE-5、SE-8、SE-15、SE-30、SE-70、SE-150)求出的标准曲线来换算,求出Mw。另外,数据处理使用了东曹株式会社制造的GPC-8020型号II版本6.00。
(5)膦类(1)含有率、其它含有率:通过HPLC的测定求出。具体而言,主体(Agilenttechnology株式会社制、HP1200系列)使用了色谱柱(Imtakt株式会社制、Cadernza CD-C18、),柱温设定为40℃。另外,洗脱液使用水/THF/乙腈=60/20/20(容量比),检测器使用UV检测器(检测波长:280nm)。精确称量0.1g苯氧基树脂清漆,溶解于THF中,总量设为10mL,注入5μL。每次测量都用THF/乙腈=50/50(容量比)进行色谱柱的清洗。使用预先用膦类制作的标准曲线进行了定量。没有峰(没有检测出)的情况下,表示为“ND”。另外,式(1)表示的膦类的含有率用“膦类(1)含有率”表示,除此之外的膦类的含有率用“其它含有率”表示。
(6)玻璃化转变温度(Tg):根据IPC-TM-650 2.4.25.c标准进行测定。具体而言,用在差示扫描热量测定的第二个循环得到的DSC图表的外推玻璃化转变开始温度(Tig)表示。差示扫描热量测定装置使用了SII Nanotechnology株式会社制造的EXSTAR6000 DSC6200。测量试样是将树脂薄膜穿孔,层叠,封装在铝制胶囊中来使用的。测定中,以10℃/分钟的升温速度从室温到280℃进行了2个循环。
(7)反应性:根据苯氧基树脂的Mw按照以下基准进行评价。
○:Mw在30000~150000的范围
×:Mw小于30000或超过150000
(8)贮藏稳定性:对于树脂组合物,用目视观察在25℃下放置24小时后的状态,按照以下基准评价贮藏稳定性。
○:不会凝胶化而具有流动性
×:凝胶化而变得不具有流动性
以下的实施例中使用的环氧树脂、固化剂、催化剂及溶剂如下所述。
[2官能环氧树脂]
A1:双酚A型液状环氧树脂(日铁化学和材料株式会社制、エポトートYD-128、环氧当量186)
A2:3,3’,5,5’-四甲基-4,4’-双酚的环氧树脂(三菱化学株式会社制、YX-4000、环氧当量186)
[2官能酚类化合物]
B1:双酚A(日铁化学和材料株式会社制、羟基当量:114)
B2:9 9’-双(4-羟基苯基)芴(大坂气体化学株式会社制、BPF、酚性羟基当量175)
B3:10-(2,5-二羟基苯基)-10H-9-氧代-10-磷杂菲-10-氧化物(三光化学株式会社制、HCA-HQ、酚性羟基当量162、磷含有率9.5%)
[催化剂]
C1:三(邻甲苯基)膦(北兴化学工业株式会社制)
C2:三(2,4-二甲基苯基)膦(北兴化学工业株式会社制)
C3:三(2,5-二甲基苯基)膦(北兴化学工业株式会社制)
C4:三(邻甲氧基苯基)膦(北兴化学工业株式会社制)
C5:2-乙基-4-甲基咪唑(四国化成工业株式会社制、产品名:キュアゾール2E4MZ)
C6:三(2,6-二甲氧基苯基)膦(试剂)
C7:三苯基膦(试剂)(试剂)
C8:三(3,5-二甲基苯基)膦(北兴化学工业株式会社制)
[溶剂]
S1:环己酮
S2:环戊酮
S3:甲基乙基酮
S4:二乙二醇二甲醚
[固化剂]
D1:ポリメリックMDI(BASF INOAC polyurethane株式会社制、Lupranate M5S、异氰酸酯当量132)
实施例1
在具备搅拌装置、温度计、氮气导入装置、冷却管、油水分离器及滴加装置的玻璃制反应容器中,在室温下加入624份作为2官能环氧树脂的A1、376份作为2官能酚类化合物的B1、375份作为溶剂的S1,通入氮气并搅拌,同时升温到145℃,添加1.0份C1作为催化剂后,升温到165℃,在相同温度下反应10小时。使用375份作为稀释溶剂的S2、750份S3进行稀释混合,得到不挥发成分为40%的苯氧基树脂清漆。
用辊涂机将得到的苯氧基树脂清漆涂布在脱模膜(聚酰亚胺膜制)上,使溶剂干燥后的厚度为60μm,在180℃下干燥20分钟后,剥离从脱模膜得到的干燥膜。重叠2张该干燥薄膜,使用真空压力机,在真空度为0.5kPa、干燥温度为200℃、加压压力为2MP a的条件下加压60分钟,得到厚度为100μm的苯氧基树脂薄膜。另外,为了调整厚度,使用了厚度为100μm的间隔物。
另外,对于得到的苯氧基树脂清漆100份,配合15份D1作为固化剂,得到树脂组合物。
实施例2~10、比较例1~5
除了将2官能环氧树脂、2官能酚类化合物、溶剂、及催化剂的种类和使用量、以及反应时间如表1所示那样设定以外,与实施例1同样地得到了苯氧基树脂清漆、苯氧基树脂膜及树脂组合物。
使用苯氧基树脂清漆测定环氧当量、磷含有率、膦类含有率、其它含有率及Mw,使用苯氧基树脂膜测定Tg,使用树脂组合物确认贮藏稳定性。
其结果如表1所示。另外,表中的“-”表示未测定。
由表1可知,使用了上述式(1)表示的膦类的实施例1~10中,反应活性高,苯氧基树脂的分子量范围适当,且苯氧基树脂或其树脂组合物的贮藏稳定性优良。另一方面,在比较例1~5中,没有同时满足反应活性和苯氧基树脂或其组合物的贮藏稳定性这两者的例子。
Claims (13)
2.根据权利要求1所述的苯氧基树脂的制造方法,其中,相对于2官能环氧树脂1.0摩尔,使用2官能酚类化合物0.95~1.05摩尔。
3.根据权利要求1或2所述的苯氧基树脂的制造方法,其中,上述膦类的使用量相对于2官能环氧树脂和2官能酚类化合物的总量100质量份为0.001~5质量份。
4.根据权利要求1~3中任一项所述的苯氧基树脂的制造方法,其中,2官能环氧树脂和/或2官能酚类化合物的一部分或全部是含芴环的化合物。
5.根据权利要求1~4中任一项所述的苯氧基树脂的制造方法,其中,2官能环氧树脂和/或2官能酚类化合物的一部分或全部是含磷化合物。
6.根据权利要求5所述的苯氧基树脂的制造方法,其中,得到的苯氧基树脂的磷含有率为1~6质量%。
7.根据权利要求1~6中任一项所述的苯氧基树脂的制造方法,其中,得到的苯氧基树脂的环氧当量为4000~200000g/eq.。
8.一种苯氧基树脂,其特征在于,其是通过权利要求1~7中任一项所述的制造方法得到的。
10.一种树脂组合物,其是通过在权利要求8或9所述的苯氧基树脂中配合固化成分而形成的。
11.根据权利要求10所述的树脂组合物,其中,固化成分是选自环氧树脂、丙烯酸酯树脂、三聚氰胺树脂、尿素树脂、酚醛树脂、酸酐化合物、胺系化合物、咪唑系化合物、酰胺系化合物、阳离子聚合引发剂、有机膦类、聚异氰酸酯化合物和封端异氰酸酯化合物中的至少一种。
12.根据权利要求10或11所述的树脂组合物,其进一步配合有填充材料。
13.一种固化物,其是通过将权利要求10~12中任一项所述的树脂组合物固化而形成的。
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JP2000154237A (ja) * | 1998-09-18 | 2000-06-06 | Nagase Chiba Kk | リペアラブル組成物およびそれを用いたアウタ―バンプ補強剤 |
US20090215929A1 (en) * | 2005-05-18 | 2009-08-27 | Nagase Chemtex Corporation | Method for Producing Fiber-Reinforced Thermally Meltable Epoxy Resin |
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US5202407A (en) * | 1992-01-24 | 1993-04-13 | The Dow Chemical Company | Precatalyzed catalyst compositions, process for preparing epoxy resins curable compositions, articles resulting from curing the resultant compositions |
JP2000154237A (ja) * | 1998-09-18 | 2000-06-06 | Nagase Chiba Kk | リペアラブル組成物およびそれを用いたアウタ―バンプ補強剤 |
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CN115637088A (zh) * | 2022-11-12 | 2023-01-24 | 佛山市金镭科技有限公司 | 一种实现高速涂布的电化铝油性色层涂料及其制备方法 |
CN115637088B (zh) * | 2022-11-12 | 2023-06-27 | 佛山市金镭科技有限公司 | 一种实现高速涂布的电化铝油性色层涂料及其制备方法 |
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