CN1330673A - 低聚碘化的聚碳酸酯的应用 - Google Patents
低聚碘化的聚碳酸酯的应用 Download PDFInfo
- Publication number
- CN1330673A CN1330673A CN99814477A CN99814477A CN1330673A CN 1330673 A CN1330673 A CN 1330673A CN 99814477 A CN99814477 A CN 99814477A CN 99814477 A CN99814477 A CN 99814477A CN 1330673 A CN1330673 A CN 1330673A
- Authority
- CN
- China
- Prior art keywords
- hydroxyphenyl
- oligo
- ester carbonate
- iodine
- polycarbonate
- 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.)
- Pending
Links
- 229920000515 polycarbonate Polymers 0.000 title claims description 25
- 239000004417 polycarbonate Substances 0.000 title claims description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 11
- 239000011630 iodine Substances 0.000 claims abstract description 11
- 150000002009 diols Chemical group 0.000 claims description 5
- 229920006352 transparent thermoplastic Polymers 0.000 claims description 2
- 239000000523 sample Substances 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 12
- 229920003023 plastic Polymers 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- -1 iodate phenol Chemical compound 0.000 description 10
- 239000004033 plastic Substances 0.000 description 9
- 239000001294 propane Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000006085 branching agent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000206 moulding compound Substances 0.000 description 4
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 4
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 150000002497 iodine compounds Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical class [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 1
- HJZJMARGPNJHHG-UHFFFAOYSA-N 2,6-dimethyl-4-propylphenol Chemical compound CCCC1=CC(C)=C(O)C(C)=C1 HJZJMARGPNJHHG-UHFFFAOYSA-N 0.000 description 1
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 1
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
- XSVZEASGNTZBRQ-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfinylphenol Chemical compound OC1=CC=CC=C1S(=O)C1=CC=CC=C1O XSVZEASGNTZBRQ-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- RTNVDKBRTXEWQE-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-butan-2-yl-4-tert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O RTNVDKBRTXEWQE-UHFFFAOYSA-N 0.000 description 1
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical class CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 1
- LDQYTDPXIMNESL-UHFFFAOYSA-N 2-methyl-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C)=C1 LDQYTDPXIMNESL-UHFFFAOYSA-N 0.000 description 1
- FXTKWBZFNQHAAO-UHFFFAOYSA-N 3-iodophenol Chemical compound OC1=CC=CC(I)=C1 FXTKWBZFNQHAAO-UHFFFAOYSA-N 0.000 description 1
- SUCTVKDVODFXFX-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfonyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(S(=O)(=O)C=2C=C(C)C(O)=C(C)C=2)=C1 SUCTVKDVODFXFX-UHFFFAOYSA-N 0.000 description 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical class OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- PBTXWTNXVCYRJA-UHFFFAOYSA-N 4-hept-2-enylphenol Chemical compound CCCCC=CCC1=CC=C(O)C=C1 PBTXWTNXVCYRJA-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004079 fireproofing Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/109—Esters; Ether-esters of carbonic acid, e.g. R-O-C(=O)-O-R
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/10—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B90/00—Instruments, implements or accessories specially adapted for surgery or diagnosis and not covered by any of the groups A61B1/00 - A61B50/00, e.g. for luxation treatment or for protecting wound edges
- A61B90/39—Markers, e.g. radio-opaque or breast lesions markers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
- Toys (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
本发明涉及具有含碘端基的低聚碳酸酯用于具有高X-射线反差、高透明度、高热稳定性和优良机械性能的模塑制品,特别是用于玩具和医疗零件的应用。
Description
本发明涉及具有含碘端基的低聚碳酸酯用于具有高X-射线反差的模塑制品,特别是用于玩具和医疗附件的应用。
具有尽可能高的透明度和优良机械性能并且能在X-射线检查中从体内检出的材料,是医疗和儿童玩具领域迫切需要的。不同于金属制品,用塑料制成的制品通常不能,或者很难在X-射线图象中检出,特别是在骨骼后面时。可利用适当添加剂将X-射线反差赋予此种模塑组合物。
具有含碘端基的聚碳酸酯构成的透明塑料模塑组合物描述在US3,469,704和DE-A1720812中。
然而,其合成的成本,特别是在聚合物具有高分子量的情况下,可能极高,而且模塑件中获得的碘含量在某些情况下又很低。
在市售供应的含碘化合物中,可能发生由相容性、色牢度和分子迁移所引起的问题。
因而在先有技术中,迄今依然没有具有足以供透明塑料制品,特别是玩具和医疗附件使用的具有适当X-射线反差的塑料组合物。
由于具有优异机械性能,聚碳酸酯长期以来被用作,特别是透明并承受高机械应力的玩具零件。本发明旨在研发一种塑料,它能够在传统X-射线图象中检出,同时不改变(原有)高透明度,对机械性能的损害也尽可能仅仅微乎其微。在塑料仍然可被探测到的层厚度应尽可能小,但最多1.2mm。
本发明目标是研发一种模塑组合物,它具有在X-射线检查中足够的反差,同时具有优良机械性能和透明度。从毒理学来说,不得加入重金属,因为正在寻找儿童玩具用材。
据此,本申请提供具有含碘端基的低聚碳酸酯用于具有高X-射线反差的模塑制品的应用,其中低聚碳酸酯包含多于一个二醇单元并且重均分子量Mw小于3,000。
上述含碘化合物彼此之间以及与其他含碘物质的混合物也可以。
特别合适的低聚碳酸酯是包含碘化酚的那些,例如2-碘苯酚、3-碘苯酚、4-碘苯酚、2,3-二碘苯酚、2,4-二碘苯酚、2,5-二碘苯酚、2,6-二碘苯酚、,3,4-二碘苯酚、3,5-二碘苯酚、2,3,4-三碘苯酚、2,3,5-三碘苯酚、2,3,6-三碘苯酚、2,4,5-三碘苯酚、2,4,6-三碘苯酚、3,4,5-三碘苯酚,乃至它们的烷基取代的化合物,作为链端基团。2,4,6-三碘苯酚是尤其优选的端基。本专利中提到的所有用于聚碳酸酯的二醇都适合作为该碘化低聚碳酸酯的二醇单元;2,2-双(4-羟基苯基)丙烷是优选的。
模塑制品,特别是玩具和医疗设备,包含该低聚碘化合物的数量相当于碘含量介于0.2~19.9wt%,优选0.3~15wt%,尤其优选0.4~10wt%。
该具有含碘端基的低聚碳酸酯通常应用在透明塑料中。
所用的透明塑料优选是透明热塑性塑料,尤其优选烯键不饱和单体的聚合物和/或双官能活性化合物的缩聚物。
特别合适的塑料是基于二酚的聚碳酸酯或共聚碳酸酯。但是,本发明的低聚物也可与聚-或共聚丙烯酸酯以及聚-或共聚甲基丙烯酸酯,例如聚-或共聚甲基丙烯酸甲酯配合使用,也可作为与苯乙烯的共聚物使用,例如透明聚苯乙烯-丙烯腈(SAN)。
它们还可加入到透明环状烯烃、对苯二甲酸的聚-或共缩聚物,例如聚-或共聚对苯二甲酸乙二醇酯(PET或共聚PET)或者二醇改性的PET(PETG)中。
本领域技术人员利用该聚碳酸酯或共聚碳酸酯将取得优异的效果。
用于本发明目的的热塑性芳族聚碳酸酯是均聚碳酸酯或者共聚碳酸酯;聚碳酸酯按照已知的方式可以是线型的或者是支链的。
该低聚碳酸酯和聚碳酸酯或共聚碳酸酯是按照已知方式由二酚、碳酸衍生物,任选地链终止剂以及任选地支化剂来制备的。
有关聚碳酸酯的制备细节已经由许多专利说明发表大约40年了。这里,作为参考仅举出Schnell,“聚碳酸酯化学与物理”,《聚合物评论》,卷9,国际科学出版社,纽约、伦敦、悉尼,1964;D.Freitag,U.Grigo,P.R.Müller,H.Nouvertne’,拜耳公司,“聚碳酸酯”,《聚合物科学与工程大全》,卷11,第2版,1988,pp.648~718;以及最后,Dres.U.Grigo,K.Kirchner和P.R.Müller,“聚碳酸酯”,Becker/Braun,《塑料手册》,卷3/1,聚碳酸酯、聚缩醛、聚酯、纤维素酯,Carl Hanser出版社,慕尼黑、维也纳,1992,pp.117~299。
适合制备聚碳酸酯的二酚例如是:氢醌、间苯二酚、二羟基联苯、双(羟苯基)链烷、双(羟苯基)环烷、双(羟苯基)硫醚、双(羟苯基)醚、双(羟苯基)酮、双(羟苯基)砜、双(羟苯基)亚砜、α,α’-双(羟苯基)二异丙基苯类,乃至它们的环上烷基化的以及环上卤化的化合物。
优选的二酚是:4,4’-二羟基联苯、2,2-双(4-羟苯基)丙烷、2,4-双(4-羟苯基)-2-甲基丁烷、1,1-双(4-羟苯基)-对-二异丙基苯、2,2-双(3-甲基-4-羟苯基)丙烷、2,2-双(3-氯-4-羟苯基)丙烷、双(3,5-二甲基-4-羟苯基)甲烷、2,2-双(3,5-二甲基-4-羟苯基)丙烷、双(3,5-二甲基-4-羟苯基)砜、2,4-双(3,5-二甲基-4-羟苯基)-2-甲基丁烷、1,1-双(3,5-二甲基-4-羟苯基)-对-二异丙基苯、2,2-双(3,5-二氯-4-羟苯基)-丙烷、2,2-双(3,5-二溴-4-羟苯基)丙烷以及1,1-双(4-羟苯基)-3,3,5-三甲基环己烷。
尤其优选的二酚是2,2-双(4-羟苯基)丙烷、2,2-双(3,5-二甲基-4-羟苯基)丙烷,2,2-双(3,5-二氯-4-羟苯基)丙烷、2,2-双(3,5-二溴-4-羟苯基)丙烷、1,1-双(4-羟苯基)环己烷以及1,1-双(4-羟苯基)-3,3,5-三甲基环己烷。
上述以及其他合适的二酚例如描述在:US-PS 3 028 635、2 999835、3 148 172、2 991 273、3 271 367、4 982 014以及2 999 846,德国公开文件1 570 703、2 063 050、2 036 052、2 211 956和3832 396,法国专利1 561 518;专著,H.Schnell,《聚碳酸酯化学与物理》,国际科学出版社,纽约,1964,以及日本公开的专利申请62039/1986、62040/1986和105550/1986中。
在均聚碳酸酯的情况下,仅使用一种二酚。在共聚碳酸酯的情况下,使用几种二酚。
合适的碳酸衍生物的例子是光气或碳酸二苯基酯。
单酚和单羧酸都适合作为链终止剂。合适的单酚是苯酚本身、烷基苯酚,例如甲酚、对叔丁基苯酚、对辛基苯酚、对异辛基苯酚、对正壬基苯酚、和对异壬基苯酚、卤代酚,例如对氯苯酚、2,4-二氯苯酚、对溴苯酚和2,4,6-三溴苯酚、2,4,6-三碘苯酚、对碘苯酚及其混合物。
优选的链终止剂是对叔丁基苯酚。
合适的多羧酸是苯甲酸、烷基苯甲酸和卤代苯甲酸。
优选的链终止剂是对应于通式(I)的酚
其中R是氢、叔丁基或者支链或非支链C8-和/或C9-烷基基团。
链终止剂的用量,以相应二酚的使用摩尔数为基准介于0.1mo1%~5mol%。链终止剂可在光气化之前、期间或之后加入。
合适的支化剂是聚碳酸酯化学已知的三官能或三官能以上的化合物,特别是具有3或3个以上酚羟基基团的那些。
合适的支化剂例如是:间苯三酚、4,6-二甲基-2,4,6-三(4-羟苯基)-2-庚烯、4,6-二甲基-2,4,6-三(4-羟苯基)庚烷、1,3,5-三(4-羟苯基)苯、1,1,1-三(4-羟苯基)乙烷、三(4-羟苯基)苯甲烷、2,2-双[4,4-双(4-羟苯基)环己基]丙烷、2,4-双(4-羟苯基异丙基)苯酚、2,6-双(2-羟基-5’-甲基苄基)-4-甲基苯酚、2-(4-羟苯基)-2-(2,4-二羟基苯基)丙烷、六(4-(4-羟苯基异丙基)-苯基)邻苯二甲酸酯(orthoterephthalate)、四(4-羟苯基)-甲烷、四(4-(4-羟苯基异丙基)苯氧基)甲烷以及1,4-双(4’,4″-二羟基三苯基)甲基)苯,乃至2,4-二羟基苯甲酸、1,3,5-苯三酸、氰脲酰氯以及3,3-双(3-甲基-4-羟苯基)-2-氧代-2,3-二氢吲哚。
任选使用的支化剂的用量介于0.05mol%~2mol%,还是以使用的相应二酚摩尔数为基准。
支化剂可随同二酚和链终止剂一起放在碱相中引入,或者放在有机溶剂中以溶液形式在光气化之前加入。在酯交换法的情况下,支化剂随同二酚一起引入。
所有这些生产热塑性聚碳酸酯的步骤乃是本领域技术人员熟悉的。
该塑料自然应构成组合物的主体,因此它通常以模塑制品的85.0~99.9wt%,优选90~99wt%,尤其优选93~98wt%的量存在。
在优选的实施方案中,模塑件的碘含量介于0.2~19.9wt%,优选0.3~15wt%,尤其优选0.4~10wt%。
然而,模塑件的碘含量介于20.1~30wt%,也可能是合意的。
为改善组合物,另外还可加入至少1种在热塑性材料优选聚碳酸酯和共聚碳酸酯中习惯存在的其他添加剂——例如,稳定剂(如描述在,譬如EP 0 839 623 Al和EP 0 500 496 A1中),特别是热稳定剂,特别是有机亚磷酸酯或膦类,例如三苯基膦;脱模剂,例如脂肪酸的甘油酯或者四羟甲基甲烷酯,其中不饱和脂肪酸也可以是完全或部分地可环氧化的,特别是甘油的单硬脂酸酯或季戊四醇的硬脂酸酯(PETS);防燃剂、抗静电剂、紫外吸收剂,例如三唑类;填料、发泡剂、染料、颜料、荧光增白剂、酯交换催化剂和成核剂或类似物——优选每种的用量最高5wt%,优选0.01~5wt%,以整个混合物为基准,尤其优选0.01~1wt%,以塑料的数量为基准。
上述添加剂的混合物也可以。
特别好的性能是在采用三唑系列紫外稳定剂时达到的。这里,尤其可举出以下这些:2-(3’,5’-双(1,1-二甲基苄基)-2’-羟苯基)苯并三唑、2-(2’-羟基-5’-(叔辛基)-苯基)苯并三唑、2-(2’-羟基-3’-(2-丁基)-5’-(叔丁基)苯基)苯并三唑、双(3-(2H-苯并三唑基)-2-羟基-5-叔辛基)甲烷、2-(4-己氧基-2-羟苯基)-4,6-二苯基-1,3,5-三嗪以及二苯酮类,例如2,4-二羟基二苯酮。
如此获得的X-射线不透聚合物组合物可转化为模塑制品,例如玩具零件,乃至纤维、薄膜、带、片材、多壁片材、容器、管材以及其他型材,为此可采用传统方法,例如热压、纺丝、挤出或注塑。该聚合物组合物也可加工成流延片材。因此,本发明还涉及本发明聚合物组合物用于生产模塑制品的应用。多层体系的应用也是令人感兴趣的。在这方面,本发明聚合物组合物,其中含碘添加剂含量比较高者,以薄层形式施加到由X-射线透明的聚合物构成的模塑制品上。该施加可在母体物质成形的同时或者成形后立即实施,例如通过复合挤出或者多组分注塑来实现。但是,该施加也可能是对最终成形的母体物质,例如通过层合以薄膜或者通过溶液涂布。该模塑组合物尤其适合用于儿童玩具透明零件,或者用于医疗用途。在这方面,此种模塑制品最特别适合用于儿童玩具的小零件。
实施例
本发明碘化低聚碳酸酯的制备
161.1g(0.11mol)低聚[2,2-双(4-羟苯基)丙烷碳酸酯]氯甲酸酯(聚合度约等于5),被溶解在1000g二氯甲烷中。在20℃~25℃、搅拌下加入由89.1g(0.189mol)2,4,6-三碘苯酚、35.6g(0.40mol)45%氢氧化钠溶液和800g水组成的澄清溶液。5min后,向其中加入0.71g N-乙基哌啶,然后混合物剧烈搅拌30min。二氯甲烷相被从水相中分离出来,然后洗涤至不合电解质。蒸发出溶剂,浓缩溶液在120℃、水喷射真空下进行干燥。
收率:202g无色固体
分析:酚羟基:160mg/kg,可皂化氯:<0.2mg/kg
碘含量:约27%
实例1
94.7份聚碳酸酯(Makrolon 2808,拜耳公司)与5.9wt%本发明低聚碳酸酯(三碘苯酚端基)和0.5wt%脱模剂PETS在280℃由双螺杆挤塑机一起进行混炼,然后注塑成形为各种不同厚度的试验棒。这些模塑件的性能载于表1中。
表1
弹性模量:2500N/mm2
断裂伸长(elongation at tear):119%
Tg=143℃
模塑件碘含量:1.6%
1.2mm厚试验棒:可被X-射线探测
1.6mm厚试验棒:可被X-射线探测
2.4mm厚试验棒:可被X-射线探测
3.2mm厚试验棒:可被X-射线探测
上述X-射线可探测性位于医疗领域传统极限范围内。
这些模塑件的透明度每种情况均大于85%。
即使当包含85wt%聚碳酸酯、14.5wt%本发明低聚物(三碘苯酚端基)和0.5wt%脱模剂PETS时,试验棒仍然完全透明。
因此,这些模塑件可在传统医疗X-射线检查中从人体内检出,即使在有骨骼遮挡的情况下。
低分子量碘化合物的加入将导致材料的塑化。这可从玻璃化转变温度的降低以及溶液粘度的降低看出。然而,实例1中高玻璃化转变温度Tg却实际上保持不变,因此高热挠曲温度维持不变。
Claims (6)
1.具有含碘端基的低聚碳酸酯用于具有高X-射线反差的模塑制品的应用,其特征在于,低聚碳酸酯包含多于一个二醇单元并且重均分子量Mw小于3,000。
2.权利要求1的应用,其特征在于,模塑制品另外还包含至少一种透明热塑性塑料,优选非卤化聚碳酸酯或共聚碳酸酯,其含量以模塑制品为基准介于80~99.9wt%,优选85~98wt%,尤其优选90~97wt%。
3.以上权利要求中至少一项的应用,其特征在于,模塑件的碘含量介于0.2~19.9wt%,优选0.3~15wt%,尤其优选0.4~10wt%。
4.以上权利要求中至少一项的应用,其特征在于,模塑件的碘含量介于20.1~30wt%。
5.包含有含碘端基的低聚碳酸酯的玩具,其特征在于,该低聚碳酸酯包含多于一个二醇单元并且重均分子量Mw小于3,000,以便改善X-射线反差。
6.医疗设备,例如探头或连接段,其包含具有含碘端基的低聚碳酸酯,其特征在于,该低聚碳酸酯包含多于一个二醇单元并且重均分子量Mw小于3,000,以便改善X-射线反差。
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JPH0857034A (ja) * | 1994-08-25 | 1996-03-05 | Terumo Corp | X線造影性医療用成型品 |
DE19545289A1 (de) * | 1995-12-05 | 1997-06-12 | Bayer Ag | Thermoplastische Massen mit verbessertem Röntgenkontrast |
DE19726191A1 (de) * | 1997-06-20 | 1998-12-24 | Bayer Ag | Verwendung von Jod-phenyl-carbonat-haltigen Polycarbonaten zur Herstellung von speziellen Formteilen |
-
1999
- 1999-12-07 CN CN99814477A patent/CN1330673A/zh active Pending
- 1999-12-07 DE DE59907397T patent/DE59907397D1/de not_active Expired - Fee Related
- 1999-12-07 US US09/868,205 patent/US6348560B1/en not_active Expired - Fee Related
- 1999-12-07 JP JP2000589596A patent/JP2002533493A/ja active Pending
- 1999-12-07 ES ES99961062T patent/ES2209534T3/es not_active Expired - Lifetime
- 1999-12-07 CA CA002355647A patent/CA2355647A1/en not_active Abandoned
- 1999-12-07 WO PCT/EP1999/009557 patent/WO2000037530A1/de active IP Right Grant
- 1999-12-07 AU AU17802/00A patent/AU1780200A/en not_active Abandoned
- 1999-12-07 EP EP99961062A patent/EP1141080B1/de not_active Expired - Lifetime
-
2002
- 2002-06-20 HK HK02104612.8A patent/HK1042908A1/zh unknown
Also Published As
Publication number | Publication date |
---|---|
WO2000037530A1 (de) | 2000-06-29 |
ES2209534T3 (es) | 2004-06-16 |
AU1780200A (en) | 2000-07-12 |
JP2002533493A (ja) | 2002-10-08 |
EP1141080B1 (de) | 2003-10-15 |
CA2355647A1 (en) | 2000-06-29 |
EP1141080A1 (de) | 2001-10-10 |
DE59907397D1 (de) | 2003-11-20 |
US6348560B1 (en) | 2002-02-19 |
HK1042908A1 (zh) | 2002-08-30 |
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