JP2021008546A - シアノ基含有炭化水素樹脂およびその製造方法 - Google Patents
シアノ基含有炭化水素樹脂およびその製造方法 Download PDFInfo
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- JP2021008546A JP2021008546A JP2019122130A JP2019122130A JP2021008546A JP 2021008546 A JP2021008546 A JP 2021008546A JP 2019122130 A JP2019122130 A JP 2019122130A JP 2019122130 A JP2019122130 A JP 2019122130A JP 2021008546 A JP2021008546 A JP 2021008546A
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- hydrocarbon resin
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- carbon atoms
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- 239000013032 Hydrocarbon resin Substances 0.000 title claims abstract description 197
- 229920006270 hydrocarbon resin Polymers 0.000 title claims abstract description 197
- 125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 112
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 239000000178 monomer Substances 0.000 claims abstract description 118
- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 115
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- 238000006243 chemical reaction Methods 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 50
- 239000003054 catalyst Substances 0.000 claims description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
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- 239000011347 resin Substances 0.000 claims description 16
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 15
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- 238000012986 modification Methods 0.000 claims description 13
- 230000004048 modification Effects 0.000 claims description 13
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- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 239000000203 mixture Substances 0.000 description 41
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- 229910052799 carbon Inorganic materials 0.000 description 9
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- 239000011572 manganese Substances 0.000 description 9
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- 125000005843 halogen group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
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- 230000003197 catalytic effect Effects 0.000 description 5
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- 239000003446 ligand Substances 0.000 description 5
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
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- 125000001624 naphthyl group Chemical group 0.000 description 4
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- 230000035484 reaction time Effects 0.000 description 4
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- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本発明のシアノ基含有炭化水素樹脂は、アニリン点が、45℃以上90℃以下であることが好ましい。
本発明のシアノ基含有炭化水素樹脂において、前記炭化水素樹脂が、1,3−ペンタジエン単量体単位20〜70質量%、炭素数4〜6の脂環式モノオレフィン単量体単位10〜50質量%、炭素数4〜8の非環式モノオレフィン単量体単位5〜40質量%、脂環式ジオレフィン単量体単位0〜1質量%、および芳香族モノオレフィン単量体単位0〜40質量%を含む樹脂であることが好ましい。
R−C2H4−CN・・・(1)
(上記一般式(1)中、Rは、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよい芳香環基、シアノ基、ヒドロキシ基、またはシクロアルキル基を示す。)
本発明のシアノ基含有炭化水素樹脂の製造方法において、前記ヒドロシアノ化反応を、下記一般式(2)で表されるビニル基含有化合物の沸点以上の温度で行うことが好ましい。
R−CH=CH2・・・(2)
(上記一般式(2)中、Rは、前記一般式(1)中のRと同じである。)
本発明における炭化水素樹脂は、シアノ基含有炭化水素の原料となる樹脂であり、炭素数4〜8の不飽和脂肪族単量体単位および/または炭素数8〜10の芳香族単量体単位を含む炭化水素樹脂である。
炭素数4〜8の不飽和脂肪族単量体単位を形成するための、炭素数4〜8の不飽和脂肪族単量体としては、芳香環を含まず、不飽和炭化水素を少なくとも含む、炭素数4〜8のものであればよく、このような単量体としては、例えば、1,3−ペンタジエン、炭素数4〜6の脂環式モノオレフィン単量体、炭素数4〜8の非環式モノオレフィン単量体、炭素数4〜8の脂環式ジオレフィン単量体等を挙げることができる。
炭素数8〜10の芳香族単量体単位を形成するための、炭素数8〜10の芳香族単量体としては、芳香環を有し、不飽和脂肪族単量体と共重合することができる、炭素数8〜10のものであればよく、例えば、炭素数8〜10の芳香族モノオレフィン単量体等を挙げることができる。
炭化水素樹脂を製造する方法としては、上記した各単量体単位を構成可能な各単量体を有する重合性成分(単量体混合物A)を、好適には付加重合する限りにおいて、特に限定されない。たとえば、フリーデルクラフツ型のカチオン重合触媒を用いた付加重合によって、炭化水素樹脂を得ることができる。
本発明のシアノ基含有炭化水素樹脂は、上述した炭化水素樹脂を、ヒドロシアノ化してなるシアノ基が導入された炭化水素樹脂である。
R−C2H4−CN・・・(1)
(上記一般式(1)中、Rは、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよい芳香環基、シアノ基、ヒドロキシ基、またはシクロアルキル基を示す。)
ヒドロシアノ化反応工程において用いる、シアノ基含有化合物は、ヒドロシアノ化触媒の存在下、上述した炭化水素樹脂とヒドロシアノ化反応する化合物であればよいが、下記一般式(1)で表される化合物を好適に用いることができる。
R−C2H4−CN・・・(1)
ヒドロシアノ化反応工程で用いるヒドロシアノ化触媒は、炭化水素樹脂と、シアノ基含有化合物とのヒドロシアノ化反応において、触媒として機能するものであれば限定されない。ヒドロシアノ化触媒としては、例えば、ニッケル錯体と、助触媒と、配位子とを用いることができる。
R−CH=CH2・・・(2)
変性率(%)=100−[100×(シアノ基含有炭化水素樹脂のオレフィン性二重結合率/炭化水素樹脂のオレフィン性二重結合率)]
反応前の炭化水素樹脂と、反応後のシアノ基含有炭化水素樹脂について、1H−NMRスペクトル測定により各々の炭素−炭素単結合、オレフィン性二重結合、および芳香族基の割合を求めた。また、反応前の炭化水素樹脂と、反応後のシアノ基含有炭化水素樹脂について、炭素−炭素単結合およびオレフィン性二重結合の合計量中の、オレフィン性二重結合量の割合を算出し、オレフィン性二重結合率とした。そして、反応前後のオレフィン性二重結合率に基づいて、下記式によって変性率を算出した。
変性率(%)=100−[100×(シアノ基含有炭化水素樹脂のオレフィン性二重結合率/炭化水素樹脂のオレフィン性二重結合率)]
ゲル浸透クロマトグラフィを用いて重合体の重量平均分子量(Mw)および数平均分子量(Mn)を測定し、分子量分布(Mw/Mn)を算出した。
その際、測定器としてはHLC−8320(東ソー社製)を用い、カラムはTSKgelα−M(東ソー社製)二本を直列に連結して用い、検出器は示差屈折計RI−8320(東ソー社製)を用いた。そして、展開溶媒としてテトラヒドロフランを用いて、重合体の重量平均分子量(Mw)および数平均分子量(Mn)を標準ポリスチレン換算値として求めた。そして、分子量分布(Mw/Mn)を算出した。
試料である炭化水素樹脂およびシアノ基含有炭化水素樹脂について、JIS K 2256に従い測定した。
試料である炭化水素樹脂およびシアノ基含有炭化水素樹脂についての官能試験は、公益社団法人におい・かおり環境協会発行の臭気の嗅覚測定法(第5版)における臭気強度表示法に従って行った。具体的には、まず、1粒の大きさを約10mm×5mm×5mmとした炭化水素樹またはシアノ基含有炭化水素樹脂10gを120mLの耐熱性容器に入れて、アルミ箔でフタをした。そして、この炭化水素樹脂またはシアノ基含有炭化水素樹脂の入った耐熱性容器を、オーブンに入れて、温度160℃、30分間の条件で加熱し、加熱後の臭気の確認を行った。臭気の確認は、石油樹脂の臭気に慣れていない(すなわち、普段の生活において、石油樹脂の臭気に触れることのない)4人のパネルにより行った。本試験においては、嗅覚疲労を防ぐため、4人のパネルを2人ずつの2班に分けて、1班ずつ臭気を嗅ぐという方法を採用した。また、臭気を嗅ぐサンプルの順番は、無作為とした。
0:無臭
1:やっと認知できる臭い(検知閾値濃度)
2:何の臭いであるか判る弱い臭い(認知閾値濃度)
3:楽に感知できる臭い
4:強い臭い
5:強烈な臭い
重合反応器にシクロペンタン34.5部およびシクロペンテン26.2部の混合物を重合反応器に仕込み、60℃に昇温した後、塩化アルミニウム0.7部を添加した(混合物M1)。引き続き、1,3−ペンタジエン43.4部、イソブチレン8.4部、スチレン21.3部、C4−C6不飽和炭化水素0.6部、ジシクロペンタジエン0.1部、およびC4−C6飽和炭化水素8.2部からなる混合物a1と、t−ブチルクロライド0.5部とを、それぞれ、別のラインを通して、60分間に亘り温度(60℃)を維持して、上記混合物M1を含む重合反応器に連続的に添加しながら重合を行った。その後、水酸化ナトリウム水溶液を重合反応器に添加して、重合反応を停止した。なお、重合反応時の重合反応器中の成分の種類および量を表1にまとめて示した。重合停止により生成した沈殿物をろ過により除去し、変性前樹脂および未反応単量体等を含む重合体溶液を得た。
また、重合体溶液の一部を取り出し、これを蒸留釜に仕込み、窒素雰囲気下で加熱し、重合溶媒と未反応単量体とを除去し、炭化水素樹脂(A−1)とした。
重合反応器に添加する成分の種類および量、ならびに重合温度を表1に示すとおりにそれぞれ変更したこと以外は、製造例1と同様にして、製造例2〜4として、炭化水素樹脂(A−2)〜(A−4)をそれぞれ得た。なお、製造例1に記載のないジイソブチレン、シクロペンタジエン、および無水マレイン酸は、1,3−ペンタジエン等と共に混合し、重合に供した。
窒素雰囲気下、耐圧性のガラス反応容器に、炭化水素樹脂(A−1)50部と、脱気・脱水したトルエン160部およびブチロニトリル32部とを加えた後、ニッケル錯体として、ビス(1,5−シクロオクタジエン)ニッケルを炭化水素樹脂(A−1)50部に対して0.2部(0.1モル%)と、助触媒として、ジメチルクロロアルミニウムを炭化水素樹脂(A−1)50部に対して0.6部(0.1モル%)と、配位子として、ビス[2−(ジフェニルホスフィノ)フェニル]エーテルを炭化水素樹脂(A−1)50部に対して0.4部(0.1モル%)と、をそれぞれ加えた。この混合物を、窒素雰囲気下、90℃で5時間反応させて、シアノ基含有炭化水素樹脂を得た。得られたシアノ基含有炭化水素樹脂について、数平均分子量、重量平均分子量、分子量分布、芳香族の含有割合、オレフィン性二重結合の含有割合、炭素−炭素単結合の含有割合、オレフィン性二重結合率、変性率、アニリン点をそれぞれ測定および算出した。さらに、臭気強度試験(6段階)を行った。結果を表1に示す。
炭化水素樹脂(A−1)の代わりに、製造例2〜4で得た炭化水素樹脂(A−2)〜(A−4)100部を使用した以外は、実施例1と同様に反応を行い、シアノ基含有炭化水素樹脂をそれぞれ得た。得られた実施例2〜4のシアノ基含有炭化水素樹脂について、実施例1と同様にして、数平均分子量、重量平均分子量、分子量分布、芳香族の含有割合、オレフィン性二重結合の含有割合、炭素−炭素単結合の含有割合、オレフィン性二重結合率、変性率、アニリン点をそれぞれ測定および算出した。さらに、臭気強度試験(6段階)を行った。結果を表1に示す。
製造例1で得られた炭化水素樹脂(A−1)を溶融状態とし、溶融状態の炭化水素樹脂(A−1)100部に対して、無水マレイン酸3.1部を添加し、230℃で1時間付加反応させた後、酸化防止剤としてペンタエリスリトールテトラキス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート](商品名「イルガノックス1010」、BASF社製)0.2部を添加し、混合した。その後、反応後の溶融樹脂を取り出し、室温まで放冷することにより、変性炭化水素樹脂(B−1)を得た。得られた変性炭化水素樹脂(B−1)について、実施例1と同様にして、数平均分子量、重量平均分子量、分子量分布、芳香族の含有割合、オレフィン性二重結合の含有割合、炭素−炭素単結合の含有割合、オレフィン性二重結合率、変性率、アニリン点をそれぞれ測定および算出した。さらに、臭気強度試験(6段階)を行った。結果を表1に示す。
一方、一般式(1)で表されるシアノ基含有化合物以外の変性剤を用いて得られた炭化水素樹脂は、アニリン点は比較的低いものの、変性率は低く、臭気の強いものであった(比較例1)。
Claims (7)
- 炭素数4〜8の不飽和脂肪族単量体単位および/または炭素数8〜10の芳香族単量体単位を含む炭化水素樹脂を、ヒドロシアノ化してなる、シアノ基含有炭化水素樹脂。
- 重量平均分子量が、1,000以上10,000以下である請求項1に記載のシアノ基含有炭化水素樹脂。
- アニリン点が、45℃以上90℃以下である請求項1または2に記載のシアノ基含有炭化水素樹脂。
- 前記炭化水素樹脂が、
1,3−ペンタジエン単量体単位20〜70質量%、
炭素数4〜6の脂環式モノオレフィン単量体単位10〜50質量%、
炭素数4〜8の非環式モノオレフィン単量体単位5〜40質量%、
脂環式ジオレフィン単量体単位0〜1質量%、および
芳香族モノオレフィン単量体単位0〜40質量%を含む樹脂である請求項1〜3のいずれかに記載のシアノ基含有炭化水素樹脂。 - 炭素数4〜8の不飽和脂肪族単量体および/または炭素数8〜10の芳香族単量体を重合して得られた炭化水素樹脂を、ヒドロシアノ化触媒の存在下に下記一般式(1)で表されるシアノ基含有化合物と接触させることで、ヒドロシアノ化反応させるヒドロシアノ化反応工程を備えるシアノ基含有炭化水素樹脂の製造方法。
R−C2H4−CN・・・(1)
(上記一般式(1)中、Rは、水素原子、置換基を有していてもよいアルキル基、置換基を有していてもよい芳香環基、シアノ基、ヒドロキシ基、またはシクロアルキル基を示す。) - 前記ヒドロシアノ化反応による、前記シアノ基含有炭化水素樹脂の変性率が、0.1モル%以上100モル%以下である請求項5に記載のシアノ基含有炭化水素樹脂の製造方法。
- 前記ヒドロシアノ化反応を、下記一般式(2)で表されるビニル基含有化合物の沸点以上の温度で行う請求項5または6に記載のシアノ基含有炭化水素樹脂の製造方法。
R−CH=CH2・・・(2)
(上記一般式(2)中、Rは、前記一般式(1)中のRと同じである。)
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"Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation", SCIENCE, vol. VOL 351 ISSUE 6275, JPN6023024689, pages 832 - 836, ISSN: 0005091334 * |
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