JP7460259B2 - 樹脂およびその製造方法 - Google Patents
樹脂およびその製造方法 Download PDFInfo
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- JP7460259B2 JP7460259B2 JP2023507809A JP2023507809A JP7460259B2 JP 7460259 B2 JP7460259 B2 JP 7460259B2 JP 2023507809 A JP2023507809 A JP 2023507809A JP 2023507809 A JP2023507809 A JP 2023507809A JP 7460259 B2 JP7460259 B2 JP 7460259B2
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- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical compound CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical group N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical group N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
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-
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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Description
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、直接結合;または-CO-L’-であり、
L’は、置換もしくは非置換のアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なり、
*は、樹脂の主鎖に連結される部位を意味する。
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なる。
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、直接結合;または-CO-L’-であり、
L’は、置換もしくは非置換のアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なり、
*は、樹脂の主鎖に連結される部位を意味する。
アッベ数=(nD-1)/(nF-nC)
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なる。
Ra1、Ra2、Rb1、およびRb2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
L’は、置換もしくは非置換のアリーレン基であり、
a1、a2、b1、およびb2はそれぞれ0または1である。
1.モノマー(Monomer)1の合成
化合物1-A 47.4g(100mmol、1.0eq)および化合物1-B 34.5g(250mmol、2.5eq)を280gのテトラヒドロフラン(THF)に溶解し、80℃のオイルバス(oil bath)にて30分間撹拌した。K2CO3 55.2g(400mmol、4.0eq)を300mLの水に溶解した後、その溶液の内部温度を50℃以上に維持しつつ10分間滴加した。Pd(t-Bu3P)2触媒1.53g(3mmol、0.03eq)を内部温度60℃で投入した。1時間の撹拌後、エチルアセテート(EA)/H2Oで洗浄して有機層を分離し、溶媒を真空濃縮した。n-ヘキサン(n-Hex)とジクロロメタン(DCM)によりカラムクロマトグラフィーして精製した後、n-ヘキサン(n-Hex)で沈殿し、固体として化合物1-Cを得た。
化合物1-C 50.0g(100mmol、1.0eq)、化合物1-D 22.0g(250mmol、2.5eq)、K2CO3 2.77g(20mmol、0.20eq)をジメチルアセトアミド(DMAc)250gに溶解し、120℃のオイルバス(oil bath)にて2時間撹拌した。冷却後、水を投入し、固体の析出後に濾過した。得られた固体をエチルアセテート(EA)とジクロロメタン(DCM)によりカラムクロマトグラフィーして精製した後、n-ヘキサン(n-Hex)で沈殿し、白色固体としてモノマー1を46.3g得た。
MS:[M+H]+=588
MS:[M+H]+=588
MS:[M+H]+=688
MS:[M+H]+=768
MS:[M+H]+=768
MS:[M+H]+=438
モノマー1の代わりにモノマー2~5を用いたことを除いては、樹脂1の製造方法と同様の方法で樹脂2~5を製造した。
モノマー1の代わりに比較例C1のモノマーを用いたことを除いては、樹脂1の製造方法と同様の方法で比較例樹脂P1を製造した。
モノマー1の代わりにモノマー2~5を用いたことを除いては、樹脂6の製造方法と同様の方法で樹脂7~10を製造した。
モノマー1の代わりに比較例C1のモノマーを用いたことを除いては、樹脂6の製造方法と同様の方法で比較例樹脂P2を製造した。
重合した樹脂試料の分子量および分子量分布をゲル浸透クロマトグラフィー(GPC)を介して確認し、熱的特性を調査するために示差走査熱量計(DSC)を用いてサーモグラム(thermogram)を得た。屈折率およびアッベ数を測定するために、製膜後、エリプソメータ(ellipsometer)を用いて光の波長に応じた結果値を得た。
アッベ数=(nD-1)/(nF-nC)
Claims (15)
- 下記化学式1で表される単位を含む樹脂:
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Lは、直接結合;または-CO-L’-であり、
L’は、置換もしくは非置換のアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なり、
*は、樹脂の主鎖に連結される部位を意味する。 - 前記R1およびR2は水素である、請求項1に記載の樹脂。
- 前記L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換の炭素数6~20のアリーレン基;または置換もしくは非置換の炭素数4~20のヘテロアリーレン基である、請求項1に記載の樹脂。
- 前記Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のエチレン基である、請求項1に記載の樹脂。
- 前記X1~X4はOである、請求項1に記載の樹脂。
- 重量平均分子量は10,000g/mol~200,000g/molである、請求項1に記載の樹脂。
- ガラス転移温度(Tg)は200℃~250℃である、請求項1に記載の樹脂。
- 波長589nmで測定された屈折率が1.68~1.75である、請求項1に記載の樹脂。
- 下記化学式1aで表される化合物:
R1およびR2は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;または置換もしくは非置換のシクロアルキル基であり、
r1は、0~4の整数であり、r1が2以上である場合、2以上のR1は互いに同一または異なり、
r2は、0~4の整数であり、r2が2以上である場合、2以上のR2は互いに同一または異なり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
X1~X4は、互いに同一または異なり、それぞれ独立して、O;またはSであり、
Z1およびZ2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキレン基;または置換もしくは非置換のシクロアルキレン基であり、
aおよびbは、互いに同一または異なり、それぞれ独立して、1~10の整数であり、aおよびbがそれぞれ2以上である場合、各括弧内の構造は互いに同一または異なる。 - 前記化学式1aは、下記化合物の中から選択されるいずれか一つである、請求項9に記載の化合物:
- 下記化学式1aで表される化合物;およびポリエステル前駆体またはポリカーボネート前駆体を含む樹脂製造用組成物を重合するステップを含む、請求項1から8のいずれか一項に記載の樹脂の製造方法:
- 前記ポリエステル前駆体は、下記化学式Aで表され、前記ポリカーボネート前駆体は、下記化学式Bで表される、請求項11に記載の樹脂の製造方法:
Ra1、Ra2、Rb1、およびRb2は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
L’は、置換もしくは非置換のアリーレン基であり、
a1、a2、b1、およびb2はそれぞれ0または1である。 - 請求項1から8のいずれか一項に記載の樹脂を含む樹脂組成物。
- 請求項13に記載の樹脂組成物を含む成形品。
- 光学レンズである、請求項14に記載の成形品。
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