JP2014080464A - 熱硬化性樹脂組成物 - Google Patents
熱硬化性樹脂組成物 Download PDFInfo
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 39
- 239000011342 resin composition Substances 0.000 title claims abstract description 29
- 239000007849 furan resin Substances 0.000 claims abstract description 40
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000002978 peroxides Chemical class 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims abstract description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims abstract description 5
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940077239 chlorous acid Drugs 0.000 claims abstract description 5
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims abstract description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940045872 sodium percarbonate Drugs 0.000 claims abstract description 5
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims abstract description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims abstract description 4
- -1 acetic acid peroxide Chemical class 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 33
- 239000011347 resin Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 25
- 238000005452 bending Methods 0.000 description 19
- 238000001723 curing Methods 0.000 description 15
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 12
- 239000000047 product Substances 0.000 description 10
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 229920000747 poly(lactic acid) Polymers 0.000 description 4
- 239000004626 polylactic acid Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 240000007582 Corylus avellana Species 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000010905 bagasse Substances 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
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- 239000005014 poly(hydroxyalkanoate) Substances 0.000 description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 2
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- 238000003825 pressing Methods 0.000 description 2
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-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
- 239000002028 Biomass Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920000704 biodegradable plastic Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 235000013312 flour Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
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- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Mold Materials And Core Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】フラン樹脂に硬化剤とともに過酸化物を添加することで、成形体の表面及び内部が均一に硬化可能となる熱硬化性樹脂組成物および硬化方法であり、過酸化物が過酸化水素水、過炭酸ナトリウム、過酸化酢酸、過硫酸アンモニウム、過硫酸カリウム、過硫酸ナトリウム、次亜塩素酸、及び亜塩素酸から選ばれ、フラン樹脂100質量部に対して0.01質量部以上5質量部未満である。
【選択図】なし
Description
また、PBS(Poly Butylene Succinate)は、現在は石油由来の原料が用いられているが、今後においては、植物由来樹脂として作製する研究が開発されており、主原料の一つであるコハク酸を植物由来で作製する技術についての開発がなされている。
そのため、一度に厚膜を形成しようとする場合は内部の樹脂成分は硬化不足となる。また、金型内で板状の成形体を成形すると内部だけでなく表面の酸素の供給も制限され、樹脂が硬化不足となり高強度の成形物を得ることは困難であるという問題があった。
(1) フラン樹脂、硬化剤、及び過酸化物を含有する熱硬化性樹脂組成物。
(2) 過酸化物が過酸化水素水、過炭酸ナトリウム、過酸化酢酸、過硫酸アンモニウム、過硫酸カリウム、過硫酸ナトリウム、次亜塩素酸、及び亜塩素酸から選ばれる1種以上のものである(1)に記載の熱硬化性樹脂組成物。
(3) 過酸化物の含有量がフラン樹脂100質量部に対して0.01質量部以上5質量部未満である(1)または(2)に記載の熱硬化性樹脂組成物。
(4) フラン樹脂に過酸化物を添加することを特徴とするフラン樹脂の硬化方法。
(5) (1)〜(3)のいずれかに記載の熱硬化性樹脂組成物を加熱加圧下で硬化するフラン樹脂の硬化方法。
本発明で用いるフラン樹脂はフラン環を有する樹脂であればよいが、フラン樹脂として現在産業化されているものはフルフリルアルコールを主原料としたものである。フルフリルアルコールの原料は、ヘミセルロースを含む植物原料であるコーンコブ、バガス、籾殻が代表的なものである。これらを無機酸の存在下で加熱すると、五炭糖が生成し、さらに脱水反応を経てフルフラールとなる。フルフラールは蒸留にて分離され、さらに水素添加することでフルフリルアルコールを得ることができる。このフルフリルアルコールを初期縮合したものがフラン樹脂であり、常温で褐色かつ液状の樹脂である。
(熱硬化性樹脂組成物の調製)
フラン樹脂(日立化成工業株式会社製、VF−303)180gに対し、硬化剤としてp−トルエンスルホン酸0.945gと34.5質量%の過酸化水素水1.26g(フラン樹脂100質量部に対して過酸化水素0.24質量部)を添加し、混合後に真空脱泡して熱硬化性樹脂組成物を得た。
ステンレス製の金型(縦横200mm、深さ2mm)に離型剤(ナガセケムテックス株式会社製、Mould Release Agents QZ 13)を塗布した後、前記熱硬化性樹脂組成物を金型に充填した。その後加熱プレス装置に金型を設置し、20MPaの圧力にて、30℃で2時間、65℃で3時間、115℃で4時間、最後に145℃で4時間加熱加圧し、フラン樹脂を含む成形体を得た。
(曲げ試験)
前記成形体を幅25mm、厚み2.0mm、長さ60mmに切り出し、試験片とした。試験片を少なくとも5本作製し、曲げ試験を実施した。インストロン型万能試験機(株式会社島津製作所製 オートグラフ、AGS-J)を用い、ヘッド速度を1.0mm/min、支点間距離を40mmとして前記試験片の3点曲げ試験を行った。5本の試験片の曲げ強度と曲げ弾性率の平均値を表1に示す。
配合する過酸化水素水の量を2.07g(フラン樹脂100質量部に対して過酸化水素0.40質量部)とした以外は実施例1と同様の方法で熱硬化性樹脂組成物の調製、熱硬化物の成形、曲げ試験を実施した。得られた曲げ強度及び曲げ弾性率の平均値を表1に示す。
配合する過酸化水素水の量を4.50g(フラン樹脂100質量部に対して過酸化水素0.86質量部)とした以外は実施例1と同様の方法で熱硬化性樹脂組成物の調製、熱硬化物の成形、曲げ試験を実施した。得られた曲げ強度及び曲げ弾性率の平均値を表1に示す。
配合する過酸化水素水の量を6.10g(フラン樹脂100質量部に対して過酸化水素1.17質量部)とした以外は実施例1と同様の方法で熱硬化性樹脂組成物の調製、熱硬化物の成形、曲げ試験を実施した。得られた曲げ強度及び曲げ弾性率の平均値を表1に示す。
過酸化水素水を配合しない以外は実施例1と同様の方法で熱硬化性樹脂組成物の調製、熱硬化物の成形、曲げ試験を実施した。得られた曲げ強度及び曲げ弾性率の平均値を表1に示す。
Claims (5)
- フラン樹脂、硬化剤、及び過酸化物を含有する熱硬化性樹脂組成物。
- 過酸化物が過酸化水素水、過炭酸ナトリウム、過酸化酢酸、過硫酸アンモニウム、過硫酸カリウム、過硫酸ナトリウム、次亜塩素酸、及び亜塩素酸から選ばれる1種以上のものである請求項1に記載の熱硬化性樹脂組成物。
- 過酸化物の含有量がフラン樹脂100質量部に対して0.01質量部以上5質量部未満である請求項1または2に記載の熱硬化性樹脂組成物。
- フラン樹脂に過酸化物を添加することを特徴とするフラン樹脂の硬化方法。
- 請求項1〜3のいずれかに記載の熱硬化性樹脂組成物を加熱加圧下で硬化するフラン樹脂の硬化方法。
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WO2016175247A1 (ja) * | 2015-04-30 | 2016-11-03 | 日立化成株式会社 | 熱硬化性樹脂材料、硬化物及びその製造方法 |
CN110272610A (zh) * | 2019-07-16 | 2019-09-24 | 安徽升隆电气有限公司 | 一种阻燃防爆电气监测设备材料及其制备方法 |
CN113234327A (zh) * | 2021-05-22 | 2021-08-10 | 云南柒捌玖农业发展有限公司 | 一种甘蔗渣生产可降解塑料的方法 |
CN113385634A (zh) * | 2020-03-14 | 2021-09-14 | 江苏华岗材料科技发展有限公司 | 一种节能环保型呋喃树脂铸造醇基固化剂的制备方法 |
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JPS54145323A (en) * | 1978-05-04 | 1979-11-13 | Mitsubishi Heavy Ind Ltd | Production of cast mold of furan resin or phenol resin |
JPH07165469A (ja) * | 1993-12-13 | 1995-06-27 | Hitachi Chem Co Ltd | ガラス状炭素の製造法 |
JP2004521975A (ja) * | 2001-02-14 | 2004-07-22 | スチロフェン インターナショナル ピーティーワイ リミテッド | ポリマー複合発泡体 |
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WO2016175247A1 (ja) * | 2015-04-30 | 2016-11-03 | 日立化成株式会社 | 熱硬化性樹脂材料、硬化物及びその製造方法 |
CN110272610A (zh) * | 2019-07-16 | 2019-09-24 | 安徽升隆电气有限公司 | 一种阻燃防爆电气监测设备材料及其制备方法 |
CN113385634A (zh) * | 2020-03-14 | 2021-09-14 | 江苏华岗材料科技发展有限公司 | 一种节能环保型呋喃树脂铸造醇基固化剂的制备方法 |
CN113234327A (zh) * | 2021-05-22 | 2021-08-10 | 云南柒捌玖农业发展有限公司 | 一种甘蔗渣生产可降解塑料的方法 |
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