JPH02634A - Aromatic polyester and its production - Google Patents
Aromatic polyester and its productionInfo
- Publication number
- JPH02634A JPH02634A JP23271988A JP23271988A JPH02634A JP H02634 A JPH02634 A JP H02634A JP 23271988 A JP23271988 A JP 23271988A JP 23271988 A JP23271988 A JP 23271988A JP H02634 A JPH02634 A JP H02634A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phenyl
- hydroxyphenyl
- bis
- aromatic polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000728 polyester Polymers 0.000 title abstract description 24
- 125000003118 aryl group Chemical group 0.000 title abstract description 19
- 238000004519 manufacturing process Methods 0.000 title description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002531 isophthalic acids Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 7
- 150000003504 terephthalic acids Chemical class 0.000 claims 1
- 238000000465 moulding Methods 0.000 abstract description 8
- 229930185605 Bisphenol Natural products 0.000 abstract description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 4
- -1 3-phenyl-4-hydroxyphenyl Chemical group 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 14
- 229920001225 polyester resin Polymers 0.000 description 10
- 239000004645 polyester resin Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000035699 permeability Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002216 antistatic agent Substances 0.000 description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- GZEBECRWRATTQK-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-phenylphenyl)-1-phenylethyl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C=1C=C(C(O)=CC=1)C=1C=CC=CC=1)(C)C1=CC=CC=C1 GZEBECRWRATTQK-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000008301 phosphite esters Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FVBBMPBYVZWAAI-UHFFFAOYSA-N 2-butyl-4-[1-(5-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C1=C(O)C(CCCC)=CC(C(CCC)C=2C(=CC(O)=C(CCCC)C=2)C)=C1C FVBBMPBYVZWAAI-UHFFFAOYSA-N 0.000 description 1
- XKZGIJICHCVXFV-UHFFFAOYSA-N 2-ethylhexyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCC(CC)CCCC)OC1=CC=CC=C1 XKZGIJICHCVXFV-UHFFFAOYSA-N 0.000 description 1
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- BKMAEERFCKIKJR-UHFFFAOYSA-N 2-tridecoxycarbonylbenzoic acid Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O BKMAEERFCKIKJR-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- SDCYWERHEYVPHL-UHFFFAOYSA-N 3,9-diphenoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound O1CC2(COP(OC=3C=CC=CC=3)OC2)COP1OC1=CC=CC=C1 SDCYWERHEYVPHL-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 1
- NRUUIOGMQXFBGB-UHFFFAOYSA-N 4-(4-hydroxy-3-phenylphenoxy)-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1OC(C=1)=CC=C(O)C=1C1=CC=CC=C1 NRUUIOGMQXFBGB-UHFFFAOYSA-N 0.000 description 1
- DJSYZLHOGGCIPZ-UHFFFAOYSA-N 4-(4-hydroxy-3-phenylphenyl)sulfanyl-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1SC(C=1)=CC=C(O)C=1C1=CC=CC=C1 DJSYZLHOGGCIPZ-UHFFFAOYSA-N 0.000 description 1
- XHNBSKVPGDXZCU-UHFFFAOYSA-N 4-[(4-hydroxy-3-phenylphenyl)-diphenylmethyl]-2-phenylphenol Chemical compound OC1=CC=C(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=C(C(O)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 XHNBSKVPGDXZCU-UHFFFAOYSA-N 0.000 description 1
- DFAXBVOHLIMORA-UHFFFAOYSA-N 4-[(4-hydroxy-3-phenylphenyl)methyl]-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1CC(C=1)=CC=C(O)C=1C1=CC=CC=C1 DFAXBVOHLIMORA-UHFFFAOYSA-N 0.000 description 1
- VCJACCZVYXRZMP-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-phenylphenyl)propyl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(CC)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 VCJACCZVYXRZMP-UHFFFAOYSA-N 0.000 description 1
- IFVCWKXKWFXVLI-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)butan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(CC)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 IFVCWKXKWFXVLI-UHFFFAOYSA-N 0.000 description 1
- GDMUSQXSAXGHTD-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)ethyl]-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1CCC(C=1)=CC=C(O)C=1C1=CC=CC=C1 GDMUSQXSAXGHTD-UHFFFAOYSA-N 0.000 description 1
- WZBYSJDZABUYIG-UHFFFAOYSA-N 4-[8-(4-hydroxy-3-phenylphenyl)octyl]-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1CCCCCCCCC(C=1)=CC=C(O)C=1C1=CC=CC=C1 WZBYSJDZABUYIG-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- MBGYSHXGENGTBP-UHFFFAOYSA-N 6-(2-ethylhexoxy)-6-oxohexanoic acid Chemical compound CCCCC(CC)COC(=O)CCCCC(O)=O MBGYSHXGENGTBP-UHFFFAOYSA-N 0.000 description 1
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 1
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 1
- YWWHKOHZGJFMIE-UHFFFAOYSA-N monoethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(O)=O YWWHKOHZGJFMIE-UHFFFAOYSA-N 0.000 description 1
- ZICLWBMRDQUIDO-UHFFFAOYSA-N monoisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(O)=O ZICLWBMRDQUIDO-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- ILGYWHOGBUPIIQ-UHFFFAOYSA-N octan-3-yl dihydrogen phosphite Chemical compound CCCCCC(CC)OP(O)O ILGYWHOGBUPIIQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QTDSLDJPJJBBLE-PFONDFGASA-N octyl (z)-octadec-9-enoate Chemical compound CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC QTDSLDJPJJBBLE-PFONDFGASA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-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
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003056 polybromostyrene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 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
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、各種光学機器用素材として有用な新規な芳香
族ポリエステルとその製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel aromatic polyester useful as a material for various optical devices and a method for producing the same.
プラスチック光学素子は、ガラス製のものに較べて軽い
、耐衝撃性に優れる、研磨が不用である、大量生産が容
易である、非球面レンズが量産できるなどの利点を有す
ることから、近年その需要が増大している。ポリエステ
ル樹脂は、耐熱性、透明性に優れ、また、屈折率も高く
強靭な樹脂であるが、耐透湿性が低いうえ、流動性が低
（、成形時の歪みにより光学異方性が発生しやすく、光
学。Plastic optical elements have been in demand in recent years because they have advantages such as being lighter than glass ones, have excellent impact resistance, do not require polishing, are easy to mass produce, and can be mass-produced as aspherical lenses. is increasing. Polyester resin is a strong resin with excellent heat resistance and transparency, and a high refractive index, but it has low moisture permeability and low fluidity (optical anisotropy occurs due to distortion during molding). Easy and optical.
材料としては不適な樹脂であった。The resin was inappropriate as a material.
本発明は、従来のポリエステル樹脂のもつこのような難
点を解消し、耐透湿性にすぐれ、流動性もよく、光弾性
係数も低く、成形時の残留応力による歪みの小さく、光
学的に均質な成形品を提供しうる新規な芳香族ポリエス
テルを提供しようとするものである。The present invention overcomes these drawbacks of conventional polyester resins, and has excellent moisture permeability, good fluidity, low photoelastic coefficient, low distortion due to residual stress during molding, and optically homogeneous resin. The present invention aims to provide a novel aromatic polyester that can be used to form molded articles.
また、本発明は、このような新規な芳香族ポリエステル
を製造する方法をも提供しようとするものである。The present invention also provides a method for producing such a novel aromatic polyester.
本発明者らは前記目的を達成するために鋭意研究を重ね
た結果、芳香核の密度の高い特定構造を有する芳香族ポ
リエステルにおいて前記目的が達成されることを見出し
、この知見に基づいて本発明を完成するに到った。As a result of extensive research to achieve the above object, the present inventors found that the above object was achieved in an aromatic polyester having a specific structure with a high density of aromatic nuclei.Based on this knowledge, the present invention I have reached the point where I have completed the .
（式中、Ｘは一〇−１−ｓ−−（−ｃｎｚ）ａ−Ｒ′
還元粘度が０．２ｄ／ｇ未満では、成形品の機械的強度
が充分でない、また、本発明の芳香族ポリエステルの還
元粘度の好ましい範囲は、０．２〜４゜０ｄ１７ｇであ
る。還元粘度が４．Ｏｊ！／ｇを超えると、流動性が低
下することがある。(In the formula, The preferred range of the reduced viscosity of polyester is 0.2 to 4°0d17g.If the reduced viscosity exceeds 4.0j!/g, fluidity may decrease.
本発明の芳香族ポリエステルにおいて好ましいポリエス
テルは、−数式
ただしＲ１およびＲ２はそれぞれ水素原子、炭素数１〜
６のアルキル基、またはフェニル基でアリ、ｍは２〜１
０の整数であり、ｎは４〜８の整数である。）
で表される繰り返し単位を有し、かつ塩化メチレンを溶
媒とする０、５８／ｄ１濃度の溶液の２０℃における還
元粘度が０．２ ａ／ ｇ以上であることを特徴とする
新規な芳香族ポリエステルを提供するものである。The aromatic polyester of the present invention is preferably a polyester having the formula: where R1 and R2 are each a hydrogen atom and have 1 to 1 carbon atoms.
6 alkyl group or phenyl group, m is 2-1
It is an integer of 0, and n is an integer of 4 to 8. ) A novel aroma characterized by having a repeating unit represented by The present invention provides a group polyester.
で表される繰り返し単位と、−数式
一般式（Ｉ）と−数式（ｎ）で表される繰り返し単位の
割合は任意の割合とすることができ、ＣＩ）が１００モ
ル％であッテも（ＩＩ）が１００モル％であってもよい
。The ratio of the repeating unit represented by the general formula (I) to the repeating unit represented by the formula (n) can be any ratio, and if CI) is 100 mol% and Atte is ( II) may be 100 mol%.
本発明の新規な芳香族ポリエステルは、例えば、本発明
の製造法に従い、−数式
で表される二価フェノールと、テレフタル酸および／ま
たはイソフタル酸、あるいはテレフタル酸の反応性誘導
体および／またはイソフタル酸の反応性誘導体とを反応
させることにより製造することができる。The novel aromatic polyesters of the invention can be prepared, for example, by the production process of the invention: - a dihydric phenol of the formula and terephthalic acid and/or isophthalic acid, or a reactive derivative of terephthalic acid and/or isophthalic acid; It can be produced by reacting with a reactive derivative of.
本発明の製造法において用いられる一般式（■）の二価
フェノールとしては、例えば、ビス（３−フェニル−４
−ヒドロキシフェニル）エーテル、ビス（３−フェニル
−４−ヒドロキシフェニル）スルフィド、ビス（３−フ
ェニル−４−ヒドロキシフェニル）メタン、１．２−ビ
ス（３−フェニル−４−ヒドロキシフェニル）エタン、
１゜３−ビス（３−フェニル−４−ヒドロキシフェニル
）プロパン、１．４−ビス（３−フェニル−４−ヒドロ
キシフェニル）ブタン、１．６−ビス（３−フェニル−
４−ヒドロキシフェニル）ヘキサン、１．８−ビス（３
−フェニル−４−ヒドロキシフェニル）オクタン、１．
１０−ビス（３−フェニル−４−ヒドロキシフェニル）
デカン、１゜１−ビス（３−フェニル−４−ヒドロキシ
フェニル）エタン、１，１−ビス（３−フェニル−４−
ヒドロキシフェニル）プロパン、ｌ−フェニル−１，１
−ビス（３−フェニル−４−ヒドロキシフェニル）メタ
ン、２．２−ビス（３−フェニル−４−ヒドロキシフェ
ニル）プロパン、２，２−ビス（３−フェニル−４−ヒ
ドロキシフェニル）ブタン、３．３−ビス（３−フェニ
ル−４−ヒドロキシフェニル）ペンタン、１−フェニル
−１，１−ビス（３−フェニル−４−ヒドロキシフェニ
ル）エタン、１．１−ビス（３−フェニル−４−ヒドロ
キシフェニル）シクロヘキサン、１．１−ビス（３−フ
ェニル−４−ヒドロキシフェニル）シクロペンクン、２
．２−ビス（３−フェニル−４−ヒドロキシフェニル）
オクタン、ジフェニル−ビス（３−フェニル−４−ヒド
ロキシフェニル）メタンなどを挙げることができる。As the dihydric phenol of the general formula (■) used in the production method of the present invention, for example, bis(3-phenyl-4
-hydroxyphenyl) ether, bis(3-phenyl-4-hydroxyphenyl) sulfide, bis(3-phenyl-4-hydroxyphenyl)methane, 1,2-bis(3-phenyl-4-hydroxyphenyl)ethane,
1゜3-bis(3-phenyl-4-hydroxyphenyl)propane, 1.4-bis(3-phenyl-4-hydroxyphenyl)butane, 1.6-bis(3-phenyl-
4-hydroxyphenyl)hexane, 1,8-bis(3
-phenyl-4-hydroxyphenyl)octane, 1.
10-bis(3-phenyl-4-hydroxyphenyl)
Decane, 1゜1-bis(3-phenyl-4-hydroxyphenyl)ethane, 1,1-bis(3-phenyl-4-
hydroxyphenyl)propane, l-phenyl-1,1
-bis(3-phenyl-4-hydroxyphenyl)methane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 2,2-bis(3-phenyl-4-hydroxyphenyl)butane, 3. 3-bis(3-phenyl-4-hydroxyphenyl)pentane, 1-phenyl-1,1-bis(3-phenyl-4-hydroxyphenyl)ethane, 1,1-bis(3-phenyl-4-hydroxyphenyl) ) cyclohexane, 1.1-bis(3-phenyl-4-hydroxyphenyl)cyclopenkune, 2
．． 2-bis(3-phenyl-4-hydroxyphenyl)
Octane, diphenyl-bis(3-phenyl-4-hydroxyphenyl)methane, etc. can be mentioned.
これらの中でも、２．２−ビス（３−フェニル−４−ヒ
ドロキシフェニル）プロパン、１−フェニル−１，１−
ビス（３−フェニル−４−ヒドロキシフェニル）エタン
が好適である。Among these, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 1-phenyl-1,1-
Bis(3-phenyl-4-hydroxyphenyl)ethane is preferred.
本発明において、イソフタル酸の反応性誘導体とはイソ
フタル酸エステル、例えばイソフタル酸ジフェニルエス
テル、およびイソフタル酸ハライド、例えばイソフタル
酸ジクロリドを意味する。In the present invention, reactive derivatives of isophthalic acid mean isophthalic acid esters, such as isophthalic acid diphenyl ester, and isophthalic acid halides, such as isophthalic acid dichloride.
本発明において、テレフタル酸の反応性誘導体とはテレ
フタル酸エステル、例えばテレフタル酸ジフェニルエス
テル、およびテレフタル酸ハライド、例えばテレフタル
酸ジクロリドを意味する。In the present invention, reactive derivatives of terephthalic acid mean terephthalic acid esters, such as terephthalic acid diphenyl ester, and terephthalic acid halides, such as terephthalic acid dichloride.
本発明の製造法を実施するにあたっては、溶融重合法、
溶液重合法、および界面重合法のいずれをも採用するこ
とができる。In carrying out the production method of the present invention, melt polymerization method,
Either a solution polymerization method or an interfacial polymerization method can be employed.
溶融重合法の場合、−数式（ＩＩＩ）の二価フェノール
の酢酸エステルとイソフタル酸および／またはテレフタ
ル酸、あるいは二価フェノールとイソフタル酸ジフェニ
ルエステルおよび／またはテレフタル酸ジフェニルエス
テルとを、溶融させ、通常１２０〜３００°Ｃの温度で
、減圧下に１〜１０時間反応させ、本発明の新規芳香族
ポリエステルを得る。In the case of the melt polymerization method, - acetic acid ester of dihydric phenol of formula (III) and isophthalic acid and/or terephthalic acid, or dihydric phenol and diphenyl isophthalic acid ester and/or diphenyl terephthalic ester are melted and usually The reaction is carried out at a temperature of 120 to 300°C under reduced pressure for 1 to 10 hours to obtain the novel aromatic polyester of the present invention.
溶液重合法の場合、−数式（ＩＩＩ）の二価フェノール
とイソフタル酸ハライドおよび／またはテレフタル酸ハ
ライドとを、有機溶媒中、脱ハロゲン酸剤の存在下、５
〜１００ ’Ｃの温度で、１〜ｌＯ時間反応させ、本発
明の新規ポリエステル樹脂を得る。使用しうる有機溶媒
としては、ベンゼン、トルエン、クロロホルム、１．２
−ジクロロエタン、クロロベンゼン等が挙げられる。ま
た、使用しうる脱ハロゲン酸剤としては、トリエチルア
ミン等のアミン類が挙げられる。この方法においては、
触媒は必須ではないが、通常、第４級アンモニウム塩、
スルホニウム塩などが触媒として用いられる。In the case of the solution polymerization method, the dihydric phenol of formula (III) and isophthalic acid halide and/or terephthalic acid halide are mixed in an organic solvent in the presence of a dehalogenating acid agent,
React at a temperature of ~100'C for 1~10 hours to obtain the novel polyester resin of the present invention. Organic solvents that can be used include benzene, toluene, chloroform, 1.2
-Dichloroethane, chlorobenzene and the like. Further, examples of the dehalogenating acid agent that can be used include amines such as triethylamine. In this method,
Although the catalyst is not essential, it is usually a quaternary ammonium salt,
Sulfonium salts and the like are used as catalysts.
界面重合法の場合、−数式（ＩＩ［）の二価フェノール
をアルカリ水溶液に溶解し、イソフタル酸ハライドおよ
び／またはテレフタル酸ハライドを水と混ざらない溶媒
に溶解し、得られた両溶液を撹拌混合して反応させ、本
発明の新規芳香族ポリエステルを得る。反応温度は通常
、２°Ｃから使用する有機溶媒の沸点以下、好ましくは
５〜５０℃であり、反応時間は通常１分から２４時間、
好ましくは０．１〜２時間である。アルカリ水溶液とし
ては、例えば水酸化カリウム水溶液、水酸化ナトリウム
水溶液、水酸化リチウム水溶液を用いることができ、使
用するビスフェノール類を完全に溶解する濃度とする。In the case of the interfacial polymerization method, - the dihydric phenol of the formula (II[) is dissolved in an aqueous alkaline solution, the isophthalic acid halide and/or the terephthalic acid halide are dissolved in a water-immiscible solvent, and both the obtained solutions are mixed by stirring. The novel aromatic polyester of the present invention is obtained by reaction. The reaction temperature is usually 2°C to below the boiling point of the organic solvent used, preferably 5 to 50°C, and the reaction time is usually 1 minute to 24 hours.
Preferably it is 0.1 to 2 hours. As the alkaline aqueous solution, for example, a potassium hydroxide aqueous solution, a sodium hydroxide aqueous solution, or a lithium hydroxide aqueous solution can be used, and the concentration is such that the bisphenols used are completely dissolved.
上記の水と混ざらない溶媒としては、塩化メチレン、四
塩化炭素、クロロホルム等を用いることができる。さら
に、重縮合反応を促進するために、トリエチルアミンな
どの第３級アミン類、トリメチルベンジルアンモニウム
クロリドなどのアンモニウム塩等の触媒を添加して反応
を行うことが望ましい、触媒の添加量はポリマー１モル
に対し０．１〜１００ミリモルとすることが好ましい、
イソフタル酸ハライドおよび／またはテレフタル酸ハラ
イドは通常有機溶剤に１〜４０Ｗ／Ｖ％、好ましくは５
〜３０Ｗ／Ｖ％、ビスフェノール類はアルカリ水溶液に
通常１〜３０Ｗ／Ｖ％、好ましくは５〜２０Ｗ／Ｖ％の
濃度になるようにして反応させる。また、重合度を調整
するために、フェノール、Ｏ−フェニルフェノール等の
フェニルフェノール、ハロゲン化フェノール、ｐ−ｔ−
７’チルフエノール、ノニルフェノール、オクチルフェ
ノール、ヒドロキシ安息香酸エステル類、ヒドロキシフ
ェニルカルボン酸エステル類などの分子量調節剤を添加
することが望ましい。As the above water-immiscible solvent, methylene chloride, carbon tetrachloride, chloroform, etc. can be used. Furthermore, in order to promote the polycondensation reaction, it is desirable to carry out the reaction by adding a catalyst such as a tertiary amine such as triethylamine or an ammonium salt such as trimethylbenzylammonium chloride.The amount of catalyst added is 1 mol of polymer. It is preferable to set it as 0.1 to 100 mmol to
Isophthalic acid halide and/or terephthalic acid halide is usually added to an organic solvent in an amount of 1 to 40 W/V%, preferably 5%.
~30 W/V%, and bisphenols are reacted with an alkaline aqueous solution to a concentration of usually 1 to 30 W/V%, preferably 5 to 20 W/V%. In addition, in order to adjust the degree of polymerization, phenol, phenylphenol such as O-phenylphenol, halogenated phenol, p-t-
It is desirable to add a molecular weight regulator such as 7'tylphenol, nonylphenol, octylphenol, hydroxybenzoic acid esters, and hydroxyphenylcarboxylic acid esters.
このようにして得られた本発明の芳香族ポリエステルは
、耐透湿性にすぐれ、流動性もよく、光弾性係数も低く
、従って成形時に発生する歪みが小さく、光学的に均質
な成形品を提供しうるものである。The aromatic polyester of the present invention thus obtained has excellent moisture permeability, good fluidity, and a low photoelastic coefficient, so that distortion generated during molding is small and optically homogeneous molded products can be provided. It is possible.
本発明の新規な芳香族ポリエステルは、通常ポリエステ
ル樹脂の成形に用いられている方法、例えば射出成形、
押出成形、プロー成形等により成形することができ、通
常使用されている成形装置を適用することができる。The novel aromatic polyester of the present invention can be produced by methods normally used for molding polyester resins, such as injection molding.
It can be molded by extrusion molding, blow molding, etc., and commonly used molding equipment can be applied.
前記成形法においては、本発明の芳香族ポリエステルを
そのまま成形してもよいが、必要に応じ、酸化防止剤、
ｔ１燃剤、紫外線吸収剤、帯電防止剤、滑剤、着色剤等
、通常ポリエステル樹脂に添加される添加剤を配合する
ことができる。In the above molding method, the aromatic polyester of the present invention may be molded as it is, but if necessary, an antioxidant,
Additives that are usually added to polyester resins, such as T1 refueling agents, ultraviolet absorbers, antistatic agents, lubricants, and colorants, can be blended.
使用される酸化防止剤としては、例えば、２゜６−ジー
ｔ−ブチル−ｐ−クレゾール、ブチル化ヒドロキシアニ
ソール、２，６−ジーｔ−ブチル−４−エチルフェノー
ル、ステアリル−β−（３゜５−ジーも一ブチルー４−
ヒドロキシフェニル）プロピオネート、２，２′〜メチ
レンビス（４−メチル−６−ｔ−ブチルフェノール）、
２．２’メチレン−ビス（４−エチル−６−ｔ−ブチル
フェノール）、４．４’−チオビス（３−メチル−６−
ｔ−ブチルフェノール）、４．４’−ブチリデンビス（
３−メチル−６−１−ブチルフェノール）、テトラキス
〔メチレン−３−（３’ ５ジーＬ−ブチル−４−ヒ
ドロキシフェニル）プロピオネートコメタン、１，１．
３−）リス（２−メチル−４−ヒドロキシ−５−ｔ−ブ
チルフェニル）ブタン等のフェノール系化合物、フェニ
ル−β−ナフチルアミン、Ｎ、Ｎ’−ジフェニル−Ｐ−
フェニレンジアミン等のアミン系化合物、トリス（ノニ
ルフェニル）ホスファイト、トリフェニルフォスファイ
ト、トリオクタデシルフォスファイト、ジフェニルイソ
デシルフォスファイト等のリン系化合物、ジラウリルチ
オジプロピオネート、シミリスチルチオジプロピオネー
ト、ジステアリルチオジプロピオネート等の硫黄化合物
などが挙げられる。Examples of the antioxidants used include 2゜6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, stearyl-β-(3゜5-G is also one butyl 4-
hydroxyphenyl) propionate, 2,2'-methylenebis(4-methyl-6-t-butylphenol),
2.2'methylene-bis(4-ethyl-6-t-butylphenol), 4.4'-thiobis(3-methyl-6-
t-butylphenol), 4,4'-butylidene bis(
3-methyl-6-1-butylphenol), tetrakis[methylene-3-(3'5-di-L-butyl-4-hydroxyphenyl)propionate comethane, 1,1.
3-) Phenolic compounds such as lis(2-methyl-4-hydroxy-5-t-butylphenyl)butane, phenyl-β-naphthylamine, N,N'-diphenyl-P-
Amine compounds such as phenylene diamine, phosphorus compounds such as tris(nonylphenyl) phosphite, triphenyl phosphite, triotadecyl phosphite, diphenylisodecyl phosphite, dilauryl thiodipropionate, simiristyl thiodipropionate , sulfur compounds such as distearylthiodipropionate, and the like.
使用される難燃剤としては、例えば、ポリブロモスチレ
ン、デカブロモジフェニルエーテル、テトラブロモビス
フェノールＡ等のハロゲン系難燃剤、リン酸アンモニウ
ム、トリクレジルホスフェート、トリエチルホスフェー
ト、酸性リン酸エステル等のリン系難燃剤、酸化スズ、
二酸化アンチモン等の無機系難燃剤が挙げられる。Examples of flame retardants used include halogen-based flame retardants such as polybromostyrene, decabromodiphenyl ether, and tetrabromobisphenol A, and phosphorus-based flame retardants such as ammonium phosphate, tricresyl phosphate, triethyl phosphate, and acidic phosphate esters. refueling agent, tin oxide,
Examples include inorganic flame retardants such as antimony dioxide.
使用される紫外線吸収剤としては、例えば、フェニルフ
ェノ−ル、ｐ−ｔ−プチルフェニルサリシレート等のサ
リチル酸系紫外線吸収剤、２゜４−ジヒドロキシベンゾ
フェノン、２−ヒドロキシー４−メトキシベンゾフェノ
ン等のベンゾフェノン系紫外線吸収剤、２− （２’
−ヒドロキシ−５′−メチルフェニル）ベンゾトリアゾ
ール、２（２′−ヒドロキシ−５’ −ｔ−ブチルフェ
ニル）ベンゾトリアゾール等のベンゾトリアゾール系紫
外線吸収剤等が挙げられる。Examples of the UV absorbers used include salicylic acid UV absorbers such as phenylphenol and pt-butylphenyl salicylate, and benzophenone UV absorbers such as 2°4-dihydroxybenzophenone and 2-hydroxy-4-methoxybenzophenone. Absorbent, 2- (2'
-hydroxy-5'-methylphenyl)benzotriazole, 2(2'-hydroxy-5'-t-butylphenyl)benzotriazole, and other benzotriazole-based ultraviolet absorbers.
使用される帯電防止剤としては、例えば、ポリオキシエ
チレンアルキルアミン、ポリオキシエチレンアルキルア
ミド等の非イオン系帯電防止剤、アルキルスホネート、
アルキルベンゼンスルホネート等のアニオン系帯電防止
剤、第４級アンモニウムクロライド、第４級アンモニウ
ムサルフェート等のカチオン系帯電防止剤、アルキルベ
タイン型、アルキルイミダシリン型等の両性帯電防止剤
等が挙げられる。Examples of the antistatic agent used include nonionic antistatic agents such as polyoxyethylene alkylamine and polyoxyethylene alkylamide, alkyl sulfonates,
Examples include anionic antistatic agents such as alkylbenzene sulfonate, cationic antistatic agents such as quaternary ammonium chloride and quaternary ammonium sulfate, and amphoteric antistatic agents such as alkyl betaine type and alkylimidacilline type.
使用される滑剤としては、脂肪族系炭化水素、高級脂肪
族系アルコール、脂肪酸アマイド系、金属石鹸系、脂肪
酸エステル系などの滑剤が挙げられる。Examples of the lubricant used include aliphatic hydrocarbon, higher aliphatic alcohol, fatty acid amide, metal soap, and fatty acid ester lubricants.
使用される着色剤としては、プラスチックの着色に使用
される通常の着色剤を使用することができる。As the colorant used, common colorants used for coloring plastics can be used.
さらに、本発明の芳香族ポリエステルには、成形に際し
、さらに他の成分、例えば着色や透明性の劣化を防止す
るための亜リン酸エステル類、メルトインデックス値を
増大させるための可塑剤等を添加することができる。Furthermore, other components such as phosphite esters to prevent coloring and deterioration of transparency, and plasticizers to increase the melt index value are added to the aromatic polyester of the present invention during molding. can do.
この際使用される亜リン酸エステル類としては、例えば
トリブチルホスファイト、トリス（２−エチルヘキシル
）ホスファイト、トリデシルホスファイト、トリスステ
アリルホスファイト、トリフェニルホスファイト、トリ
クレジルホスファイト、トリス（ノニルフェニル）ホス
ファイト、２−エチルへキシルジフェニルホスファイト
、デシルジフェニルホスファイト、フェニル−ジー２−
エチルへキシルホスファイト、フエニルジデシルホスフ
ァイト、トリシクロヘキシルホスファイト、ジステアリ
ルペンタエリスリチルジホスファイト、ジフェニルペン
タエリスリチルジホスファイトなどが挙げられる。Examples of the phosphite esters used in this case include tributyl phosphite, tris(2-ethylhexyl) phosphite, tridecyl phosphite, trisstearyl phosphite, triphenyl phosphite, tricresyl phosphite, and tris(2-ethylhexyl) phosphite. nonylphenyl) phosphite, 2-ethylhexyldiphenylphosphite, decyldiphenylphosphite, phenyl-di-2-
Examples include ethylhexyl phosphite, phenyldidecyl phosphite, tricyclohexyl phosphite, distearyl pentaerythrityl diphosphite, diphenylpentaerythrityl diphosphite, and the like.
また、可塑剤としては、例えば２−エチルへキシルフタ
レート、ｎ７−ブチルフタレート、イソデシルフタレー
ト、トリデシルフタレート、ヘプチルフタレート、ノニ
ルフタレート等のアルキルフタレート類、２−エチルへ
キシルアジペート、２−エチルへキシルセバケート等の
二塩基酸のアルキルエステル類、リン酸トリブチル、リ
ン酸トリオクチル、リン酸トリクレジル、リン酸トリフ
ェニル等のリン酸アルキルエステル類、エポキシ化オレ
イン酸オクチル、エポキシ化オレイン酸ブチル等のエポ
キシ化脂肪酸エステル類、あるいはポリエステル形可塑
剤、塩素化脂肪酸エステル類などが挙げられる。Examples of plasticizers include alkyl phthalates such as 2-ethylhexyl phthalate, n7-butyl phthalate, isodecyl phthalate, tridecyl phthalate, heptyl phthalate, and nonyl phthalate, 2-ethylhexyl adipate, and 2-ethyl phthalate. Alkyl esters of dibasic acids such as xyl sebacate, phosphoric acid alkyl esters such as tributyl phosphate, trioctyl phosphate, tricresyl phosphate, triphenyl phosphate, etc., epoxidation of epoxidized octyl oleate, epoxidized butyl oleate, etc. Examples include fatty acid esters, polyester plasticizers, and chlorinated fatty acid esters.
また、本発明の芳香族ポリエステルの特性を損なわない
範囲で、他の樹脂を配合して成形してもよい。Further, other resins may be blended and molded within a range that does not impair the properties of the aromatic polyester of the present invention.
本発明の芳香族ポリエステルは新規なものであって、成
形性および光学的性質に優れており、スチールカメラ、
ビデオカメラ、望遠鏡、眼鏡、コンタクトレンズ、プリ
ズム類、オプティカルファイバー、ビデオディスク、オ
ーディオディスク、光メモリ−ディスクなどの光学機器
用素材や透明電極、導電性フィルムなど各種産業用資材
の素材として好適に使用できる。The aromatic polyester of the present invention is novel and has excellent moldability and optical properties.
Can be suitably used as a material for optical equipment such as video cameras, telescopes, eyeglasses, contact lenses, prisms, optical fibers, video disks, audio disks, optical memory disks, and various industrial materials such as transparent electrodes and conductive films. .
次に実施例により本発明をさらに詳細に説明するが、本
発明はこれらの例によってなんら限定されるものではな
い。EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples in any way.
実施例１
反応器中で３８．０ ｇの２．２−ビス（３−フェニル
−４−ヒドロキシフェニル）プロパンおよび５０ｍｇの
ｐ−ｔ−ブチルフェノールをＩ Ｍ−ＫＯ）１４００ｄ
に溶解させた。液温を２０°Ｃに調節し、触媒としてト
リエチルアミン０．７ ｄを加え、激しく攪拌した。Example 1 38.0 g of 2,2-bis(3-phenyl-4-hydroxyphenyl)propane and 50 mg of p-t-butylphenol were reacted in a reactor (IM-KO) 1400 d
It was dissolved in The liquid temperature was adjusted to 20°C, and 0.7 d of triethylamine was added as a catalyst, followed by vigorous stirring.
一方、イソフタル酸クロライド２０．３ ｇを塩化メチ
レン１５０ｄに溶解させ、先に調製したアルカリ水溶液
中に速やかに添加した。添加後も攪拌を続け、３０分間
反応させた。反応終了後、撹拌を停止し、塩化メチレン
４００ｍを加えて静置分離した。有機相を希塩酸にて中
和洗浄し、さらに水洗を４回繰り返した。得られた重合
体の塩化メチレン溶液を約５２のメタノールに注入して
ポリマーを沈澱、単離した。得られたポリマーの還元粘
度（ηＳｐ／ｃ ：塩化メチレンを溶媒として０．５ｇ
／ｄＪｌ濃度溶液の２０℃での還元粘度、以下同様）は
０．７５ｄｌ／ｇ、ガラス転移温度は１５５°Ｃであっ
た。On the other hand, 20.3 g of isophthalic acid chloride was dissolved in 150 d of methylene chloride and immediately added to the aqueous alkaline solution prepared previously. Stirring was continued after the addition, and the reaction was allowed to proceed for 30 minutes. After the reaction was completed, stirring was stopped, 400 m of methylene chloride was added, and the mixture was allowed to stand for separation. The organic phase was neutralized and washed with diluted hydrochloric acid, and further washed with water four times. A solution of the resulting polymer in methylene chloride was poured into about 50 methanol to precipitate and isolate the polymer. Reduced viscosity of the obtained polymer (ηSp/c: 0.5 g using methylene chloride as a solvent)
The reduced viscosity (the same applies hereinafter) of the /dJl concentration solution at 20°C was 0.75 dl/g, and the glass transition temperature was 155°C.
また、得られたポリマーの赤外線吸収スペクトル分析の
結果、１７８０ｃｍ−’の位置にカルボニル基による吸
収、１２５０Ｃ１１−’の位置にエーテル結合による吸
収が確認され、これらのことから、下記の繰り返し単位
を有するものと認められた。In addition, as a result of infrared absorption spectrum analysis of the obtained polymer, absorption due to carbonyl group at position 1780 cm-' and absorption due to ether bond at position 1250C11-' were confirmed, and from these, it was found that the polymer had the following repeating unit. It was recognized as a thing.
二のポリエステル樹脂の光弾性係数および透湿度は、第
１表に示すとおりであった。The photoelastic coefficient and moisture permeability of the second polyester resin were as shown in Table 1.
実施例２
イソフタル酸クロライド２０．３ ｇの代わりに、テレ
フタル酸クロライド２０．３ ｇを用いた以外は実施例
１と同様の操作を行った。Example 2 The same operation as in Example 1 was performed except that 20.3 g of terephthalic acid chloride was used instead of 20.3 g of isophthalic acid chloride.
７７ ｓｐ／ｃは０．６５ｄ／ｇ、ガラス転移温度は１
６２°Ｃであった。77 sp/c is 0.65 d/g, glass transition temperature is 1
The temperature was 62°C.
得られたポリマーの赤外線吸収スペクトル分析の結果は
、実施例１と同様であり、下記の繰り返し単位を有する
ものと認められた。The results of infrared absorption spectrum analysis of the obtained polymer were similar to those in Example 1, and it was confirmed that the polymer had the following repeating units.
二のポリエステル樹脂の光弾性係数および透湿度は、第
１表に′示すとおりであった。The photoelastic coefficient and moisture permeability of the second polyester resin were as shown in Table 1.
実施例３
反応器中で、５００ｒＩｔ１．の水に水酸化カリウム１
４．８ｇを溶解し、続いてこの水溶液中に２，２−ビス
（３−フェニル−４−ヒドロキシフェニル）プロパン３
８．０ｇ、トリメチルベンジルアンモニウムクロリド０
．１７ｇ、およびＯ−フェニルフェノール０．２ｇを溶
解し、液温を１０°Ｃに調整した。Example 3 In a reactor, 500 rIt1. of potassium hydroxide in water
4.8 g of 2,2-bis(3-phenyl-4-hydroxyphenyl)propane was dissolved in this aqueous solution.
8.0g, trimethylbenzylammonium chloride 0
．． 17 g and 0.2 g of O-phenylphenol were dissolved, and the liquid temperature was adjusted to 10°C.
一方、テレフタル酸クロリド、イソフタル酸りロリド各
１０．１ ｇを塩化メチレン３０８ｇに溶解し、得られ
た溶液を１０℃に調節した。この酸クロリドの塩化メチ
レン溶液を激しく攪拌しつつ、先に調整した２、２−ビ
ス（３−フェニル−４−ヒドロキシフェニル）プロパン
のアルカリ水溶液に速やかに添加した。添加後も攪拌を
続け、５０分間反応させた。反応終了後、攪拌を止め、
静置分離して有機相を希塩酸で中和洗浄した後、水洗を
５回繰り返した。得られた全芳香族ポリエステル共重合
体の塩化メチレン溶液を３１のメタノールに注入してポ
リマーを沈澱させ、単離した。得られたポリマーのフレ
ークを８０°Ｃで２４時間乾燥した。得られたポリマー
の還元粘度は０．５０ａ／ｇであり、ガラス転移温度は
１７８°Ｃであった。また、得られたポリマーの赤外線
吸収スペクトル分析の結果は、実施例１と同様であり、
下記の繰り返し単位からなるものと認められた。On the other hand, 10.1 g each of terephthalic acid chloride and isophthalic acid chloride were dissolved in 308 g of methylene chloride, and the resulting solution was adjusted to 10°C. The methylene chloride solution of this acid chloride was rapidly added to the previously prepared alkaline aqueous solution of 2,2-bis(3-phenyl-4-hydroxyphenyl)propane while stirring vigorously. Stirring was continued even after the addition, and the reaction was allowed to proceed for 50 minutes. After the reaction is complete, stop stirring and
After standing to separate and neutralizing the organic phase with diluted hydrochloric acid, washing with water was repeated five times. A methylene chloride solution of the obtained wholly aromatic polyester copolymer was poured into 31 methanol to precipitate the polymer, and the polymer was isolated. The resulting polymer flakes were dried at 80°C for 24 hours. The resulting polymer had a reduced viscosity of 0.50 a/g and a glass transition temperature of 178°C. In addition, the results of infrared absorption spectrum analysis of the obtained polymer were the same as in Example 1,
It was recognized that it consists of the following repeating units.
また、このポリエステル樹脂の光弾性係数および透湿度
は、第１表に示すとおりであった。Further, the photoelastic coefficient and moisture permeability of this polyester resin were as shown in Table 1.
実施例４
２．２−ビス（３−フェニル−４−ヒドロキシフェニル
）プロパンの代わりに、１−フエニル−１．１−ビス（
３−フェニル−４−ヒドロキシフェニル）エタンを用い
た以外は実施例３と同様の操作を行った。Example 4 1-phenyl-1,1-bis(
The same operation as in Example 3 was performed except that 3-phenyl-4-hydroxyphenyl)ethane was used.
得られ、たポリマーの還元粘度は、０．５５ｄｌ／ｇで
あり、ガラス転移温度は１８５°Ｃであった。また、赤
外線吸収スペクトル分析の結果は、実施例１と同様であ
り、下記の繰り返し単位からなるも２．２−ビス（３−
フェニル−４−ヒドロキシフェニル）プロパンの代わり
に、２，２−ビス（４−ヒドロキシフェニル）プロパン
を用いた以外は実施例３と同様の操作を行った。The resulting polymer had a reduced viscosity of 0.55 dl/g and a glass transition temperature of 185°C. In addition, the results of infrared absorption spectrum analysis are the same as in Example 1, and 2,2-bis(3-
The same operation as in Example 3 was performed except that 2,2-bis(4-hydroxyphenyl)propane was used instead of phenyl-4-hydroxyphenyl)propane.
また、得られたポリエステル樹脂の還元粘度〔ηｓｐ／
ｃ ］は０．５７准／ｇであり、ガラス転移温度は１８
８℃であった。Further, the reduced viscosity of the obtained polyester resin [ηsp/
c ] is 0.57 S/g, and the glass transition temperature is 18
The temperature was 8°C.
このポリエステルは、下記の繰り返し単位からなるもの
であることが認められた。This polyester was found to be composed of the following repeating units.
このポリエステル樹脂の光弾性係数および透湿度は、第
１表に示すとおりであった。The photoelastic coefficient and moisture permeability of this polyester resin were as shown in Table 1.
比較例１
また、このポリエステルの光弾性係数および透湿度は、
第１表に示すとおりであった。Comparative Example 1 In addition, the photoelastic coefficient and moisture permeability of this polyester are as follows:
It was as shown in Table 1.
第１表 は大である。Table 1 is large.
Claims (1)
、▲数式、化学式、表等があります▼または▲数式、化
学式、表等があります▼であり、 ただしＲ＾１およびＲ＾２はそれぞれ水素原子、炭素数
１〜６のアルキル基、またはフェニル基であり、ｍは２
〜１０の整数であり、ｎは４〜８の整数である。） で表される繰り返し単位を有し、かつ塩化メチレンを溶
媒とする０．５ｇ／ｄｌ濃度の溶液の２０℃における還
元粘度が０．２ｄｌ／ｇ以上であることを特徴とする芳
香族ポリエステル。 ２、一般式 ▲数式、化学式、表等があります▼ （式中、Ｘは−Ｏ−、−Ｓ−、−（−ＣＨ＿２）＿ｍ−
、▲数式、化学式、表等があります▼または▲数式、化
学式、表等があります▼であり、 ただしＲ＾１およびＲ＾２はそれぞれ水素原子、炭素数
１〜６のアルキル基、またはフェニル基であり、ｍは２
〜１０の整数であり、ｎは４〜８の整数である。） で表される二価フェノールと、テレフタル酸および／ま
たはイソフタル酸、あるいはテレフタル酸の反応性誘導
体および／またはイソフタル酸の反応性誘導体とを反応
させることを特徴とする一般式 ▲数式、化学式、表等があります▼ （式中、Ｘは上記と同じ意味を有する。） で表される繰り返し単位を有し、かつ塩化メチレンを溶
媒とする０．５ｇ／ｄｌ濃度の溶液の２０℃における還
元粘度が０．２ｄｌ／ｇ以上である芳香族ポリエステル
の製造法。[Claims] 1. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X is -O-, -S-, -(-CH_2)_m-
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^1 and R^2 are each a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. and m is 2
-10, and n is an integer of 4-8. ), and has a reduced viscosity of 0.2 dl/g or more at 20° C. in a solution with a concentration of 0.5 g/dl using methylene chloride as a solvent. 2. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is -O-, -S-, -(-CH_2)_m-
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^1 and R^2 are each a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. and m is 2
-10, and n is an integer of 4-8. ) A general formula characterized by reacting a dihydric phenol represented by terephthalic acid and/or isophthalic acid, or a reactive derivative of terephthalic acid and/or a reactive derivative of isophthalic acid ▲ Numerical formula, chemical formula, There are tables, etc. ▼ (In the formula, X has the same meaning as above.) Reduced viscosity at 20°C of a solution with a concentration of 0.5 g/dl and using methylene chloride as a solvent. 0.2 dl/g or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63232719A JP2551982B2 (en) | 1987-10-16 | 1988-09-19 | Aromatic polyester and its manufacturing method |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25966287 | 1987-10-16 | ||
| JP62-259662 | 1987-10-16 | ||
| JP63232719A JP2551982B2 (en) | 1987-10-16 | 1988-09-19 | Aromatic polyester and its manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02634A true JPH02634A (en) | 1990-01-05 |
| JP2551982B2 JP2551982B2 (en) | 1996-11-06 |
Family
ID=26530622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63232719A Expired - Lifetime JP2551982B2 (en) | 1987-10-16 | 1988-09-19 | Aromatic polyester and its manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2551982B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9487324B2 (en) | 2009-08-17 | 2016-11-08 | Tetra Laval Holdings & Finance S.A. | Sheet packaging material for producing sealed packages of pourable food products |
-
1988
- 1988-09-19 JP JP63232719A patent/JP2551982B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9487324B2 (en) | 2009-08-17 | 2016-11-08 | Tetra Laval Holdings & Finance S.A. | Sheet packaging material for producing sealed packages of pourable food products |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2551982B2 (en) | 1996-11-06 |
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