JP5252799B2 - ヒドロキシベンゼン誘導体およびその製造方法 - Google Patents
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- JP5252799B2 JP5252799B2 JP2006327145A JP2006327145A JP5252799B2 JP 5252799 B2 JP5252799 B2 JP 5252799B2 JP 2006327145 A JP2006327145 A JP 2006327145A JP 2006327145 A JP2006327145 A JP 2006327145A JP 5252799 B2 JP5252799 B2 JP 5252799B2
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- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000005204 hydroxybenzenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- 229960001755 resorcinol Drugs 0.000 description 30
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- 229910000831 Steel Inorganic materials 0.000 description 8
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- 239000000539 dimer Substances 0.000 description 7
- -1 benzenetricarboxylic acid compound Chemical class 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000012779 reinforcing material Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229910001369 Brass Inorganic materials 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 244000171726 Scotch broom Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 1
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzenetricarboxylic Acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010073 coating (rubber) Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- ZZPKZRHERLGEKA-UHFFFAOYSA-N resorcinol monoacetate Chemical compound CC(=O)OC1=CC=CC(O)=C1 ZZPKZRHERLGEKA-UHFFFAOYSA-N 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1,3,5−ベンゼントリカルボン酸−トリレゾルシンエステルの製造
レゾルシン176.2g(1.60mol)をピリジン176.2gに溶解した液を10〜15℃に冷却し、同温度を保ちながら、融点以上に加熱して溶融させた1,3,5−ベンゼントリカルボン酸トリクロライド24.8g(0.0934mol)を1hrかけて滴下装入した。その後室温で2hr熟成した後に115℃〜120℃まで昇温して同温度で6hr熟成を行なった。得られたマスから減圧下、120℃でピリジン留去を行なった。最終的な減圧度は20torrまで達した。
MSスペクトルデータ
FAB(pos.) m/z=487 (M+H)+
IRスペクトルデータ
1745cm−1、1227cm−1および1136cm−1
NMRスペクトルデータを表1−1および表1−2に示した。
NMRスペクトルデータを表2−1および表2−2に示した
1,3,5−ベンゼントリカルボン酸−トリレゾルシンエステル、二量体およびレゾルシンの分析
カラム : YMC社 A−312 ODS
カラム温度: 40℃
溶離液 : メタノール/水=7/3(リン酸でpH=3に調整)
検出 : UV(254nm)
実施例1で製造した組成物を供試化合物として2200mLのバンバリーミキサーを使用して、表3に示すゴム配合処方で混練り混合して、未加硫のゴム組成物を調製し、以下の方法で耐ブルーム性、ムーニー粘度、配合直後の接着性及び、配合ゴム放置後の接着性を測定、評価した。結果を表3に示す。
未加硫のゴム組成物を40℃で7日間貯蔵した後、配合剤がゴム表面に析出したか否かを目視で確認し、○、△、×で判定した。
○:表面に配合剤が析出していない。
△:一部に析出
×:全面に配合剤が析出
未加硫のゴム組成物をJIS K6300-2001に準拠して、ML(1+4)130℃を測定した。結果は数値が低い程良好であることを示す。
黄銅(Cu;63質量%、Zn;37質量%)メッキしたスチールコード(1×5構造、素線径0.25mm)を12.5mm間隔で平行に並べ、このスチールコードを上下両側から各ゴム組成物でコーティングして、これを直ちに160℃×15分の条件で加硫し、幅12.5mmのサンプルを作製した。下記の各接着性に対してASTM−D−2229に準拠して、各サンプルに対してスチールコードを引き抜き、ゴムの被覆状態を目視で観察し、0〜100%で表示、各接着性の指標とした。数値が大きい程良好であることを示す。初期接着性は前記加硫の直後に測定した。湿熱接着性は前記加硫後、70℃、湿度100%、4日の湿熱条件下で老化させた後に測定した。
前記未加硫状態のスチールコードを上下両側から各ゴム組成物でコーティングしたスチールコード−ゴム複合体を、40℃×80RH%の恒温恒湿槽に7日間放置後、160℃×15分間加硫して、初期接着性を測定し、接着安定性の指標とした。
供試化合物として本発明の組成物を使用しない以外は参考例1と同様に配合してゴム組成物を調製し、評価した。結果を表3に示した。
供試化合物としてレゾルシンをゴム基本配合に2質量部配合する以外は参考例1と同様に配合してゴム組成物を調製し、評価した。結果を表3に示した。
供試化合物としてRF樹脂をゴム基本配合に2質量部配合する以外は参考例1と同様に配合してゴム組成物を調製し、評価した。結果を表3に示した。なお、RF樹脂は下記の方法で製造した。
供試化合物として特開平7−118621号広報(特許文献2)記載の混合ポリエステルをゴム基本配合に2質量部配合する以外は参考例1と同様に配合してゴム組成物を調製し、評価した。結果を表3に示した。尚、混合ポリエステルは上記特許記載の実施例1に準じて合成した。
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JP5252799B2 true JP5252799B2 (ja) | 2013-07-31 |
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JP5265108B2 (ja) * | 2006-12-04 | 2013-08-14 | 株式会社ブリヂストン | ゴム組成物 |
JP2008138117A (ja) * | 2006-12-04 | 2008-06-19 | Bridgestone Corp | 空気入りタイヤ |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4123455A (en) * | 1977-06-13 | 1978-10-31 | American Cyanamid Company | Phenenyltris(carbonylimino) multi-anionic substituted triphenyl acids and salts |
JPS57200340A (en) * | 1981-06-03 | 1982-12-08 | Mitsui Toatsu Chem Inc | Process for selective n-substitution of aromatic aminohydroxy compound |
JP3154593B2 (ja) * | 1993-08-04 | 2001-04-09 | 三井化学株式会社 | トリメリット酸誘導体を含有する電子写真用トナー |
JP3154603B2 (ja) * | 1993-11-16 | 2001-04-09 | 三井化学株式会社 | ピロメリット酸誘導体を含有する電子写真用トナー |
JPH07168354A (ja) * | 1993-12-13 | 1995-07-04 | Sumitomo Chem Co Ltd | ポジ型レジスト組成物 |
JPH07325431A (ja) * | 1994-06-01 | 1995-12-12 | Mitsui Toatsu Chem Inc | ピロメリット酸誘導体を含有する電子写真用トナー |
DE19525941C2 (de) * | 1995-07-18 | 1999-11-25 | Ivoclar Ag Schaan | Polymerisierbares flüssigkristallines Monomer, Dentalmaterialien auf der Basis von flüssig-kristallinen Monomeren und Verwendung eines polymerisierbaren Monomers mit flüssigkristallinen Eigenschaften zur Herstellung eines Dentalmaterials |
US6232430B1 (en) * | 1996-10-23 | 2001-05-15 | Jds Uniphase Photonics C.V. | Cross-linkers for cross-linkable optical polycarbonates |
JP2006047627A (ja) * | 2004-08-04 | 2006-02-16 | Toray Ind Inc | 感光性樹脂前駆体組成物 |
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