JP6440612B2 - フェノキシ樹脂組成物及びその硬化物 - Google Patents
フェノキシ樹脂組成物及びその硬化物 Download PDFInfo
- Publication number
- JP6440612B2 JP6440612B2 JP2015508508A JP2015508508A JP6440612B2 JP 6440612 B2 JP6440612 B2 JP 6440612B2 JP 2015508508 A JP2015508508 A JP 2015508508A JP 2015508508 A JP2015508508 A JP 2015508508A JP 6440612 B2 JP6440612 B2 JP 6440612B2
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- Prior art keywords
- phenoxy resin
- resin composition
- acid anhydride
- phenoxy
- epoxy resin
- Prior art date
- 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.)
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- 229920006287 phenoxy resin Polymers 0.000 title claims description 90
- 239000013034 phenoxy resin Substances 0.000 title claims description 90
- 239000000203 mixture Substances 0.000 title claims description 47
- 150000008065 acid anhydrides Chemical class 0.000 claims description 23
- 239000003431 cross linking reagent Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 13
- 125000004018 acid anhydride group Chemical group 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 description 41
- 229920000647 polyepoxide Polymers 0.000 description 41
- 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 19
- 229910000831 Steel Inorganic materials 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000010959 steel Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- -1 phenol compound Chemical class 0.000 description 12
- 238000002156 mixing Methods 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000002845 discoloration Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical group O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 2
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 2
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZYZWCJWINLGQRL-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-diol Chemical group C1=CC(O)(O)CC=C1C1=CC=CC=C1 ZYZWCJWINLGQRL-UHFFFAOYSA-N 0.000 description 2
- JYCTWJFSRDBYJX-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1C2=CC=CC=C2C(C(=O)OC2=O)C2C1 JYCTWJFSRDBYJX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- DIQCVUZVAPYLCM-UHFFFAOYSA-N 2-[[2-chloro-4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(Cl)=CC=1OCC1CO1 DIQCVUZVAPYLCM-UHFFFAOYSA-N 0.000 description 1
- LRVJEADXJYKWPQ-UHFFFAOYSA-N 2-[[2-methyl-4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(C)=CC=1OCC1CO1 LRVJEADXJYKWPQ-UHFFFAOYSA-N 0.000 description 1
- AGXAFZNONAXBOS-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethyl)phenyl]methyl]oxirane Chemical compound C=1C=CC(CC2OC2)=CC=1CC1CO1 AGXAFZNONAXBOS-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 1
- KOWHWSRFLBFYRR-UHFFFAOYSA-N 4-[1-[3-[2-(4-hydroxyphenyl)propyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C=1)=CC=CC=1CC(C)C1=CC=C(O)C=C1 KOWHWSRFLBFYRR-UHFFFAOYSA-N 0.000 description 1
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- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/56—Polyhydroxyethers, e.g. phenoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
- C08K5/1539—Cyclic anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
1) 架橋剤(b)が、酸無水物類であること。
2) 架橋剤(b)が酸無水物基を2つ以上有する酸無水物類であること。
3) 更に、エポキシ樹脂(d)及び/又は硬化促進剤(e)を含むこと。
4) エポキシ樹脂(d)が結晶性エポキシ樹脂であること。
厚さ4mm、直径3mmの試験片を、示差走査熱量測定装置(エスアイアイ・ナノテクノロジー株式会社製EXSTAR6000 DSC6200)を用いて、10℃/分の昇温条件で、20〜280℃の範囲で測定し、セカンドスキャンのピーク値よりガラス転移温度を計算した。
(2)透明性及び黄色変色性
厚さ4mm、幅40mm、長さ40mmの試験片5枚を、目視により判定した。透明性の評価は次のとおり。○:濁りなし、△:一部に非相溶部を確認、×:相溶せず。黄色変色性評価は次のとおり。○:変色なし、△:やや変色を認める、×:黄色変色。
(3)熱膨張係数(CTE)
厚さ4mm、幅7mm、長さ7mmの試験片を、熱機械測定装置(セイコーインスツル製TMA120C)を用いて、10℃/分の昇温条件で、20〜280℃の範囲で測定し、50℃〜100℃の線膨張率を測定した。
(4)ゲル分率(Gel)
未架橋成形体1gをテトラヒドロフラン100gに室温にて溶解したときに、溶解されずに残存している部分をゲルとし、このゲル部分の重量と溶剤で溶かす前の重量との比(百分率)を求めた。ゲル分率が100%に近いほど架橋(硬化)が進んでいることを示し、完全に溶解した場合はゲル分率が0%となる。
(a-1):フェノトートYP-50S(新日鉄住金化学株式会社製ビスフェノールAタイプ、Mw=40,000、水酸基当量=284)
(a-2):フェノトートYP-70(新日鉄住金化学社製ビスフェノールA・ビスフェノールF共重合タイプ、Mw=41,000、水酸基当量=270)
(b-1):4,4'-オキシジフタル酸無水物(酸無水物当量=155、融点=225℃)
(b-2):4,4'-ビフタル酸無水物(酸無水物当量=147、融点=299℃)
(b-3):1,3,3a,4,5,9b-ヘキサヒドロ-5-(テトラヒドロ-2,5-ジオキソ-3-フラニル)ナフト[1,2-c]フラン-1,3-ジオン(酸無水物当量=150、融点=198℃)
(b-4):1,2,3,4-ブタンテトラカルボン酸二無水物(酸無水物当量=99、融点=260℃)
(b-5):水添トリメリット酸無水物(酸無水物当量=99、融点=155℃)
(b-6):水添ピロメリット酸無水物(酸無水物当量=112、融点=299℃)
(b-7):無水ヘキサヒドロフタル酸(酸無水物当量=154、融点=33℃)
(d-1):YSLV-80DE(新日鉄住金化学株式会社製ジフェニルエーテルタイプ、エポキシ当量=163、融点=83℃)
(d-2):YSLV-80XY(新日鉄住金化学株式会社製テトラメチルビスフェノールFタイプ、エポキシ当量=192、融点=72℃)
(d-3):YSLV-120TE(新日鉄住金化学株式会社製ビスフェノールスルフィドタイプ、エポキシ当量=245、融点=118℃)
(d-4):エポトートYDC-1312(新日鉄住金化学株式会社製ハイドロキノンタイプ、エポキシ当量=176、融点=138℃)
(d-5):エポトートYD-011(新日鉄住金化学株式会社製ビスフェノールAタイプ、エポキシ当量=475、軟化点=65℃)
(e-1):2−フェニルイミダゾール
フェノキシ樹脂、架橋剤、エポキシ樹脂、硬化促進剤を、それぞれ粉砕、篩分けし、100メッシュパスの粉砕品を、表1に示す割合(質量部)でドライブレンドした後、東洋精機製ラボプラストミル30mm径の二軸混練機で150〜250℃で10〜30分の温度条件で加熱混練押出して、ペレット状のフェノキシ樹脂組成物を得た。得られたペレット状のフェノキシ樹脂組成物を4mmのスペーサーを挟んだ鉄板を用いて、プレス成形機により180〜280℃、0.1〜4.9MPaの条件で15分間プレス成形し、4mm厚平板状の未架橋成形体を得た。得られた未架橋成形体の一部を使用してゲル分率を測定した。得られた未架橋成形体を更に180〜280℃、30〜60分間加熱して架橋・硬化させて、架橋フェノキシ樹脂成形体を得た。得られた架橋フェノキシ樹脂成形体を決められた寸法にそれぞれ加工して各評価用の試験片を得た。得られた試験片を用いて、ガラス転移温度、透明性、黄色変色性を評価した。結果を表1に示す。
フェノキシ樹脂としてフェノトートYP−50Sを用いた。これを4mmのスペーサーを挟んだ鉄板を用いて、プレス成形機により180℃、0.1〜4.9MPaの条件で15分間プレス成形し、4mm厚平板状の未架橋成形体を得た。得られた未架橋成形体を決められた寸法にそれぞれ加工して各評価用の試験片を得た。
フェノキシ樹脂と架橋剤とメチルエチルケトン(MEK)をサンプル管の中に所定量計量し、自転・公転ミキサーを用いて30分間室温で混合し、均一なフェノキシ樹脂組成物ワニスを得た。このワニスをプレス成形したところ、溶剤の離散に伴う発泡が起こり、均一な成形体を得ることは出来なかった。
フェノキシ樹脂、架橋剤、エポキシ樹脂、硬化促進剤を、それぞれ粉砕、篩分けし、100メッシュパスの粉末とした。この粉末を、表2に示す割合(質量部)でドライブレンドしてフェノキシ樹脂組成物とした後、実施例1〜11と同様の操作を行い、各評価用の試験片を得た。得られた試験片を用いて、ガラス転移温度、熱膨張係数、透明性、黄色変色性を評価した。結果を表2に示す。
比較例2で得られたフェノキシ樹脂組成物ワニスを180℃、0.2kPaに設定した真空オーブン中に120分間保持し、溶剤を完全に除去し、フェノキシ樹脂組成物の塊を得た。得られたフェノキシ樹脂組成物の塊を粉砕、篩分けし、100メッシュパスの粉末とした。この粉末を使用して実施例1〜11と同様の操作を行い、各評価用の試験片を得た。
比較例1と同様の操作を行い、各評価用の試験片を得た。得られた試験片を用いて、ガラス転移温度、熱膨張係数、透明性、黄色変色性を評価した。結果を表2に示す。
実施例12で得られたフェノキシ樹脂組成物と比較例2で得られたフェノキシ樹脂組成物ワニスをそれぞれ25℃の恒温室に7日間、14日間保管した後の状態を目視で観察した。実施例12で得られたフェノキシ樹脂組成物は14日間後でも目視で変化が認められなかったが、比較例2で得られたフェノキシ樹脂組成物ワニスは7日間後で濁りが確認でき、14日後では不溶解物の沈殿が認められた。目視で変化が認められなかった実施例12で得られたフェノキシ樹脂組成物の保管品をそれぞれ、実施例1〜11と同様の操作を行い、各評価用の試験片を得た。得られた試験片を用いて、ガラス転移温度、熱膨張係数、透明性、黄色変色性を評価した。結果を表3に示す。
Claims (5)
- フェノキシ樹脂(a)と架橋剤(b)とを必須成分とするフェノキシ樹脂組成物において、樹脂成分がフェノキシ樹脂(a)のみからなる無溶剤系のフェノキシ樹脂組成物であり、かつ、予め成形した後、熱によりフェノキシ樹脂(a)の水酸基を架橋剤(b)により架橋又は硬化させるためのものであることを特徴とするフェノキシ樹脂組成物。
- 架橋剤(b)が酸無水物類であり、フェノキシ樹脂(a)の2級水酸基1モルに対して酸無水物基の量が0.05〜1.0モルの範囲であることを特徴とする請求項1に記載のフェノキシ樹脂組成物。
- 前記酸無水物類が、その酸無水物基とフェノキシ樹脂(a)の水酸基が反応した後に2つ以上のカルボキシル基を生成する酸無水物類であることを特徴とする請求項2に記載のフェノキシ樹脂組成物。
- 硬化促進剤(e)を更に含むことを特徴とする請求項1に記載のフェノキシ樹脂組成物。
- 請求項1〜4のいずれかに記載のフェノキシ樹脂組成物を架橋、硬化して得られることを特徴とするフェノキシ樹脂成形体。
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