JPWO2015115611A1 - 含臭素ポリエーテル重合体及びその製造方法 - Google Patents
含臭素ポリエーテル重合体及びその製造方法 Download PDFInfo
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- JPWO2015115611A1 JPWO2015115611A1 JP2015536332A JP2015536332A JPWO2015115611A1 JP WO2015115611 A1 JPWO2015115611 A1 JP WO2015115611A1 JP 2015536332 A JP2015536332 A JP 2015536332A JP 2015536332 A JP2015536332 A JP 2015536332A JP WO2015115611 A1 JPWO2015115611 A1 JP WO2015115611A1
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- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title description 17
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(式中、
mは2〜5の整数であり、
kは5−mであり、
R1は酸素原子、NH基又は硫黄原子であり、
R2は水素原子、フッ素原子、塩素原子、ヨウ素原子、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキルチオ基、炭素数1〜4のハロアルキル基、炭素数1〜4のハロアルコキシ基、ビニル基、ニトロ基、シアノ基、アルデヒド基、アミノ基、ヒドロキシ基、チオール基、スルホ基、スルホンアミド基、又はカルボキシ基もしくはエステル基であり、kが2以上の場合、R2は同一であっても異なっていてもよく、
星印は、重合体末端又は他の構造単位との結合点を表す)
で示される繰り返し単位を含み、臭素含量が45〜80重量%である重合体、該重合体を含む難燃剤及びこれらの製造方法に関する。
(式中、
mは2〜5の整数であり、
kは5−mであり、
R1は酸素原子、NH基又は硫黄原子であり、
R2は水素原子、フッ素原子、塩素原子、ヨウ素原子、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキルチオ基、炭素数1〜4のハロアルキル基、炭素数1〜4のハロアルコキシ基、ビニル基、ニトロ基、シアノ基、アルデヒド基、アミノ基、ヒドロキシ基、チオール基、スルホ基、スルホンアミド基、又はカルボキシ基もしくはエステル基であり、kが2以上の場合、R2は同一であっても異なっていてもよく、
星印は、重合体末端又は他の構造単位との結合点を表す)
で示される繰り返し単位を含み、臭素含量が45〜80重量%である重合体である。
(式中、
mは2〜5の整数であり、
kは5−mであり、
R1は酸素原子、NH基又は硫黄原子であり、
R2は水素原子、フッ素原子、塩素原子、ヨウ素原子、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキルチオ基、炭素数1〜4のハロアルキル基、炭素数1〜4のハロアルコキシ基、ビニル基、ニトロ基、シアノ基、アルデヒド基、アミノ基、ヒドロキシ基、チオール基、スルホ基、スルホンアミド基、又はカルボキシ基もしくはエステル基であり、kが2以上の場合、R2は同一であっても異なっていてもよく、
星印は、重合体末端又は他の構造単位との結合点を表す)
で示される単量体を重合開始剤の存在下で重合することにより、下記一般式(1):
(式中、R1、R2、m、k及び星印は、前記と同義である)
で示される繰り返し単位を含み、臭素含量が45〜80重量%である重合体を得ることができる。
本試験と並行して空試験を行い、次式によってエポキシ当量を算出した。
エポキシ当量=(10000×S)/{f×(A−B)}
A:空試験に要した水酸化ナトリウム標準液の量(mL)
B:本試験に要した水酸化ナトリウム標準液の量(mL)
S:試料採取料(g)
f:水酸化ナトリウム標準液のファクター
2,4,6−トリブロモフェニルグリシジルエーテルの合成
コンデンサー及び温度計を備えた1L4つ口フラスコに、2,4,6−トリブロモフェノール(マナック(株)製)256g(0.774モル)、エピクロロヒドリン(東京化成工業(株)製)322g(3.48モル)及びイソプロピルアルコール125gを加え35℃にて撹拌溶解後、48%水酸化ナトリウム水溶液74gを1.5時間で滴下、内温65℃にて0.5時間反応した。反応後、水168gを添加し副生塩を溶解させ水層を除き、減圧下で過剰のエピクロロヒドリン及びイソプロピルアルコールを留去した。その後メチルイソブチルケトン299gと48%水酸化ナトリウム水溶液17gを加えて75℃にて1時間反応させ、さらにメチルイソブチルケトン399gを加えた後、水を加えて水洗を行った。この水洗を5回繰り返した後に有機層を減圧下において濃縮すると白色結晶が析出した。白色結晶を濾取し、200mLのメタノールで洗浄した。得られた白色結晶を送風乾燥に付すことによって、目的の2,4,6−トリブロモフェニルグリシジルエーテルを241g(0.62モル)、収率81%、エポキシ当量377g/eq、臭素含量62重量%、融点116℃で得た。目的物の1H−NMRを図1に、FT−IRチャートを図2に示す。
2,3,4,5,6−ペンタブロモフェニルグリシジルエーテルの合成
2,4,6−トリブロモフェノール(マナック(株)製)の代わりに2,3,4,5,6−ペンタブロモフェノール(マナック(株)製)を用いた以外は合成例1に準じて合成し、目的の2,3,4,5,6−ペンタブロモフェニルグリシジルエーテルを38g(70ミリモル)、収率68%、エポキシ当量570g/eq、臭素含量73重量%、融点169℃で得た。目的物の1H−NMRを図3に、FT−IRチャートを図4に示す。
2,6−ジブロモ−4−ニトロフェニルグリシジルエーテルの合成
2,4,6−トリブロモフェノール(マナック(株)製)の代わりに2,6−ジブロモ−4−ニトロフェノール(東京化成工業(株)製)を用いた以外は合成例1に準じて合成し、目的の2,6−ジブロモ−4−ニトロフェニルグリシジルエーテルを3.25g(9.2ミリモル)、収率63%、エポキシ当量355g/eq、臭素含量45重量%、融点109℃で得た。目的物の1H−NMRを図5に、FT−IRチャートを図6に示す。
2,6−ジブロモ−4−シアノフェニルグリシジルエーテルの合成
2,4,6−トリブロモフェノール(マナック(株)製)の代わりに2,6−ジブロモ−4−シアノフェノール(東京化成工業(株)製)を用いた以外は合成例1に準じて合成し、目的の2,6−ジブロモ−4−シアノフェニルグリシジルエーテルを3.19g(9.6ミリモル)、収率52%、エポキシ当量345g/eq、臭素含量47重量%、融点100℃で得た。目的物の1H−NMRを図7に、FT−IRチャートを図8に示す。
N−(2,3−エポキシプロピル)−2,4,6−トリブロモアニリンの合成
コンデンサー及び温度計を備えた四つ口フラスコに、2,4,6−トリブロモアニリン(マナック(株)製)100g(304ミリモル)、酢酸14.6g(243ミリモル)、モノクロロベンゼン23mLを加え、110℃に加熱した後、エピクロロヒドリン(東京化成工業(株)製)11.2g(121ミリモル)を4分割して滴下しながら8時間撹拌した。反応終了後、モノクロロベンゼンを留去し、室温まで冷却した。その際、析出した過剰の2,4,6−トリブロモアニリンをろ過により除去した後、メチルエチルケトン100mL、2.5mol/L水酸化ナトリウム水溶液205gを加え、還流温度で1時間撹拌した。モノクロロベンゼンで抽出した後、有機層を濃縮して粗生成物を得た。その粗生成物をイソプロピルアルコール/ヘプタン(50/50(重量比))の混合溶媒から再結晶を行うことで目的のN−(2,3−エポキシプロピル)−2,4,6−トリブロモアニリンを16.5g(42.8ミリモル)、収率35%、エポキシ当量379g/eq、臭素含量61重量%、融点40℃で得た。目的物の1H−NMRを図9に、FT−IRチャートを図10に示す。
2,4,6−トリブロモフェニルグリシジルエーテルのカチオン開環重合
コンデンサー及び温度計を備えた100mL4つ口フラスコに、窒素雰囲気下、合成例1で合成した2,4,6−トリブロモフェニルグリシジルエーテル10g(26ミリモル)及びジクロロメタン50mLを加えた。その後、五塩化アンチモン(シグマ・アルドリッチ社製)0.40g(1.3ミリモル)を加え、17〜28℃で18時間撹拌した。反応終了後、水40gで水洗し、水層を除去した後、さらに水40gを加え、水層が中性になるまで25%水酸化ナトリウム水溶液で中和した。静置分液後、有機層を減圧下で濃縮し、酢酸エチルで再沈殿させた。液相をデカンテーションにより除去することで沈殿した粘稠物を得た。得られた粘稠物を140℃減圧下で恒量となるまで乾燥に付すことによって目的物をガラス状固体として得た(収量6.6g、収率66%、臭素含量62重量%、ガラス転移温度52℃、5%重量減少温度345℃、重量平均分子量1,400(Mw/Mn=1.2))。目的物の1H−NMRを図11に、FT−IRチャートを図12に示す。
2,4,6−トリブロモフェニルグリシジルエーテルのカチオン開環重合
コンデンサー及び温度計を備えた100mL4つ口フラスコに、窒素雰囲気下、ジクロロメタン10mL、三フッ化ホウ素テトラヒドロフラン錯体(ステラケミファ(株)製)0.10g(0.71ミリモル)及びフェネチルアルコール(和光純薬工業(株)製)0.08g(0.65ミリモル)を加えた。撹拌を始めて合成例1で合成した2,4,6−トリブロモフェニルグリシジルエーテル10g(26ミリモル)を40mLのジクロロメタンで溶解したジクロロメタン溶液を内温20〜22℃に保ちながら4時間かけて滴下した。滴下終了後、さらに内温22〜25℃で12時間撹拌した。反応終了後、実施例1と同様な操作により目的物をガラス状固体として得た(収量9.0g、収率90%、臭素含量62重量%、ガラス転移温度51℃、5%重量減少温度353℃、重量平均分子量1,900(Mw/Mn=1.3))。目的物の1H−NMRを図13に、FT−IRチャートを図14に示す。
2,4,6−トリブロモフェニルグリシジルエーテルのカチオン開環重合
コンデンサー及び温度計を備えた500mL4つ口フラスコに、ジクロロメタン40mL、三フッ化ホウ素テトラヒドロフラン錯体(ステラケミファ(株)製)0.22g(1.6ミリモル)及び1,4−ブタンジオール(和光純薬工業(株)製)0.15g(1.7ミリモル)を加えた。撹拌を始めて合成例1で合成した2,4,6−トリブロモフェニルグリシジルエーテル50g(129ミリモル)を200mLのジクロロメタンで溶解したジクロロメタン溶液を内温40〜42℃で8時間かけて滴下した。滴下終了後さらに内温40〜42℃で3時間撹拌した。反応終了後、実施例1と同様な操作により目的物をガラス状固体として得た(収量47g、収率94%、臭素含量62重量%、ガラス転移温度56℃、5%重量減少温度355℃、重量平均分子量5,200(Mw/Mn=1.6))。目的物の1H−NMRを図15に、FT−IRチャートを図16に示す。
2,3,4,5,6−ペンタブロモフェニルグリシジルエーテルのカチオン開環重合
コンデンサー及び温度計を備えた200mL4つ口フラスコに、ジクロロメタン30mL、三フッ化ホウ素テトラヒドロフラン錯体(ステラケミファ(株)製)0.12g(0.86ミリモル)及び1,4−ブタンジオール(和光純薬工業(株)製)0.08g(0.9ミリモル)を加えた。撹拌を始めて合成例2で合成した2,3,4,5,6−ペンタブロモフェニルグリシジルエーテル10g(18.3ミリモル)を200mLのジクロロメタンで溶解したジクロロメタン溶液を内温40〜42℃で8時間かけて滴下した。滴下終了後さらに内温38℃〜40℃で12時間撹拌した。反応終了後、実施例1と同様な操作により目的物をガラス状固体として得た(収量8.2g、収率82%、臭素含量73重量%、ガラス転移温度100℃、5%重量減少温度330℃、重量平均分子量1,500(Mw/Mn=1.1))。目的物の1H−NMRを図17に、FT−IRチャートを図18に示す。
ジブロモフェニルグリシジルエーテルのアニオン開環重合
30mLナスフラスコに、アルゴン雰囲気下、ジブロモフェニルグリシジルエーテル(デナコールEX−147;ナガセケムテックス(株)製)2.5g(8.1ミリモル)を加え、テトラブチルアンモニウムフルオリド(1mol/Lテトラヒドロフラン溶液、d=0.92)(東京化成工業(株)製)を0.8mL(0.8ミリモル)注入し60℃に昇温して4時間撹拌した。反応終了後2mLのテトラヒドロフランで溶解し、大量のメタノールで再沈殿させた。液相をデカンテーションにより除去し、沈殿した粘稠物を得た。得られた粘稠物を140℃減圧下で恒量となるまで乾燥することで目的物をガラス状固体として得た(収量1.8g、収率72%、臭素含量52重量%、ガラス転移温度35℃、5%重量減少温度351℃、重量平均分子量1,600(Mw/Mn=1.3))。目的物の1H−NMRを図19に、FT−IRチャートを図20に示す。
ジブロモフェニルグリシジルエーテルとジブロモクレジルグリシジルエーテルの7:3混合物のアニオン開環重合
コンデンサー及び温度計を備えた100mL4つ口フラスコに、アルゴン雰囲気下、ジブロモフェニルグリシジルエーテルとジブロモクレジルグリシジルエーテルの7:3混合物(EB−200B;マナック(株)製)40g(総モル数128ミリモル)を加え、テトラブチルアンモニウムフルオリド(1mol/Lテトラヒドロフラン溶液、d=0.92)(東京化成工業(株)製)を6.7mL(6.7ミリモル)注入し50℃に昇温して48時間撹拌した。反応終了後20mLのテトラヒドロフランで溶解し、実施例5と同様の操作により目的物をガラス状固体として得た(収量35.8g、収率89.5%、臭素含量51重量%、ガラス転移温度42℃、5%重量減少温度358℃、重量平均分子量1,700(Mw/Mn=1.2))。目的物の1H−NMRを図21に、FT−IRチャートを図22に示す。
2,6−ジブロモ−4−ニトロフェニルグリシジルエーテルと2,6−ジブロモ−4−シアノフェニルグリシジルエーテルの1:1混合物のカチオン開環重合
50mLナスフラスコに、アルゴン雰囲気下、合成例3で合成した2,6−ジブロモ−4−ニトロフェニルグリシジルエーテル0.88g(2.5ミリモル)、合成例4で合成した2,6−ジブロモ−4−シアノフェニルグリシジルエーテル0.83g(2.5ミリモル)及びジクロロメタン5mLを加えた。その後、三フッ化ホウ素テトラヒドロフラン錯体(ステラケミファ(株)製)0.04g(0.29ミリモル)を加え、10〜22℃で4時間撹拌した。反応終了後、有機層が中性になるまで水洗し、静置分液後、有機層を塩酸酸性メタノールで再沈殿させた。液相をデカンテーションにより除去することで沈殿した粘稠物を得た。得られた粘稠物を140℃減圧下で恒量となるまで乾燥に付すことによって目的物をガラス状固体として得た(収量0.90g、収率53%、臭素含量47重量%、ガラス転移温度62℃、5%重量減少温度268℃、重量平均分子量2,200(Mw/Mn=1.7))。目的物の1H−NMRを図23に、FT−IRチャートを図24に示す。
N−(2,3−エポキシプロピル)−2,4,6−トリブロモアニリンのカチオン開環重合
50mLナスフラスコに、アルゴン雰囲気下、合成例5で合成したN−(2,3−エポキシプロピル)−2,4,6−トリブロモアニリン3.86g(10ミリモル)及びジクロロメタン5mLを加えた。その後、三フッ化ホウ素テトラヒドロフラン錯体(ステラケミファ(株)製)0.08g(0.6ミリモル)を加え、10〜26℃で4時間撹拌した。反応終了後、実施例7と同様な操作によって目的物をガラス状固体として得た(収量2.91g、収率75%、臭素含量62重量%、ガラス転移温度78℃、5%重量減少温度326℃、重量平均分子量1,100(Mw/Mn=1.6))。目的物の1H−NMRを図25に、FT−IRチャートを図26に示す。
本明細書に記載された全ての文献、特許出願、及び技術規格は、個々の文献、特許出願、及び技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書に参照により取り込まれる。
Claims (14)
- 下記一般式(1):
(式中、
mは2〜5の整数であり、
kは5−mであり、
R1は酸素原子、NH基又は硫黄原子であり、
R2は水素原子、フッ素原子、塩素原子、ヨウ素原子、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキルチオ基、炭素数1〜4のハロアルキル基、炭素数1〜4のハロアルコキシ基、ビニル基、ニトロ基、シアノ基、アルデヒド基、アミノ基、ヒドロキシ基、チオール基、スルホ基、スルホンアミド基、又はカルボキシ基もしくはエステル基であり、kが2以上の場合、R2は同一であっても異なっていてもよく、
星印は、重合体末端又は他の構造単位との結合点を表す)
で示される繰り返し単位を含み、臭素含量が45〜80重量%である重合体。 - 臭素含量が50重量%〜80重量%である、請求項1記載の重合体。
- R1が酸素原子である、請求項1又は2記載の重合体。
- R2が全て水素原子である、請求項1〜3のいずれか1項記載の重合体。
- 熱重量分析(TGA)における5%重量減少温度が200℃〜450℃である、請求項1〜4のいずれか1項記載の重合体。
- 請求項1〜5のいずれか1項記載の重合体を含む難燃剤。
- 下記一般式(2):
(式中、
mは2〜5の整数であり、
kは5−mであり、
R1は酸素原子、NH基又は硫黄原子であり、
R2は水素原子、フッ素原子、塩素原子、ヨウ素原子、炭素数1〜4のアルキル基、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキルチオ基、炭素数1〜4のハロアルキル基、炭素数1〜4のハロアルコキシ基、ビニル基、ニトロ基、シアノ基、アルデヒド基、アミノ基、ヒドロキシ基、チオール基、スルホ基、スルホンアミド基、又はカルボキシ基もしくはエステル基であり、kが2以上の場合、R2は同一であっても異なっていてもよく、
星印は、重合体末端又は他の構造単位との結合点を表す)
で示される単量体を重合開始剤の存在下で重合することを含む、請求項1〜5のいずれか1項記載の重合体の製造方法。 - カチオン開環重合機構により重合する、請求項7記載の製造方法。
- 重合開始剤がルイス酸である、請求項8記載の製造方法。
- さらに含活性水素化合物を併用して重合する、請求項9記載の製造方法。
- 前記含活性水素化合物がヒドロキシ化合物である、請求項10記載の製造方法。
- アニオン開環重合機構により重合する、請求項7記載の製造方法。
- 重合開始剤が四級アンモニウム塩である、請求項12記載の製造方法。
- アンモニウム塩がテトラブチルアンモニウムフルオリドである、請求項13記載の製造方法。
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