JP2011046947A - ポリエステルの製法 - Google Patents
ポリエステルの製法 Download PDFInfo
- Publication number
- JP2011046947A JP2011046947A JP2010184741A JP2010184741A JP2011046947A JP 2011046947 A JP2011046947 A JP 2011046947A JP 2010184741 A JP2010184741 A JP 2010184741A JP 2010184741 A JP2010184741 A JP 2010184741A JP 2011046947 A JP2011046947 A JP 2011046947A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyphenyl
- bis
- anhydride
- carbonate
- cyclohexane
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 229920000728 polyester Polymers 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 58
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 27
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 27
- 239000003513 alkali Substances 0.000 claims abstract description 25
- 150000002009 diols Chemical class 0.000 claims abstract description 24
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 12
- -1 undecenyl succinic anhydride Chemical compound 0.000 claims abstract description 12
- 229920006305 unsaturated polyester Polymers 0.000 claims abstract description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims abstract description 9
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims abstract description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 5
- UYCICMIUKYEYEU-ZHACJKMWSA-N 3-[(e)-dodec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCC\C=C\CC1CC(=O)OC1=O UYCICMIUKYEYEU-ZHACJKMWSA-N 0.000 claims abstract 4
- 229940014800 succinic anhydride Drugs 0.000 claims abstract 2
- 239000002245 particle Substances 0.000 claims description 68
- 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 claims description 36
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 239000003086 colorant Substances 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- DPBULAWJIMFAPI-UHFFFAOYSA-N 3-[2-(3-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC(O)=CC=1C(C)(C)C1=CC=CC(O)=C1 DPBULAWJIMFAPI-UHFFFAOYSA-N 0.000 claims 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims 4
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 claims 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 2
- RLMGYIOTPQVQJR-OLQVQODUSA-N (1s,3r)-cyclohexane-1,3-diol Chemical compound O[C@H]1CCC[C@@H](O)C1 RLMGYIOTPQVQJR-OLQVQODUSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- 229940043375 1,5-pentanediol Drugs 0.000 claims 2
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 claims 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims 2
- ZCWPSSZCHGOORK-UHFFFAOYSA-N 3-undec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCC=CC1CC(=O)OC1=O ZCWPSSZCHGOORK-UHFFFAOYSA-N 0.000 claims 2
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 claims 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 2
- 229940051250 hexylene glycol Drugs 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 2
- 235000013772 propylene glycol Nutrition 0.000 claims 2
- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 claims 2
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract description 13
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 239000001993 wax Substances 0.000 description 16
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
- 230000002776 aggregation Effects 0.000 description 12
- 230000009477 glass transition Effects 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229920001225 polyester resin Polymers 0.000 description 10
- 239000004645 polyester resin Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 238000005054 agglomeration Methods 0.000 description 7
- 239000001530 fumaric acid Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000007771 core particle Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OPLFRMXJYAHDBV-UHFFFAOYSA-N 4-ethyl-6-methyl-1,3-dioxepan-2-one Chemical compound C1(OCC(C)CC(CC)O1)=O OPLFRMXJYAHDBV-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229920006127 amorphous resin Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QDCPNGVVOWVKJG-UHFFFAOYSA-N 2-dodec-1-enylbutanedioic acid Chemical compound CCCCCCCCCCC=CC(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-UHFFFAOYSA-N 0.000 description 1
- WNCOESCMLBISHF-UHFFFAOYSA-N 2-undec-1-enylbutanedioic acid Chemical compound CCCCCCCCCC=CC(C(O)=O)CC(O)=O WNCOESCMLBISHF-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 229920006038 crystalline resin Polymers 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- QQUZYDCFSDMNPX-UHFFFAOYSA-N ethene;4-methyl-1,3-dioxolan-2-one Chemical compound C=C.CC1COC(=O)O1 QQUZYDCFSDMNPX-UHFFFAOYSA-N 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007499 fusion processing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08755—Polyesters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08757—Polycarbonates
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08793—Crosslinked polymers
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Polyesters Or Polycarbonates (AREA)
- Dry Development In Electrophotography (AREA)
- Polyethers (AREA)
Abstract
【解決手段】有機ジオールを、炭酸アルカリの第1の触媒の存在下で、環状炭酸アルキレンと反応させてポリアルコキシジオールを形成し、随意にポリアルコキシジオールを、アルカリアルコキシドの第2の触媒の存在下で、追加量の環状炭酸アルキレンと接触させて混合物を形成し、得られた混合物を、ジカルボン酸、並びに無水マレイン酸、無水トリメリト酸、無水ドデセニルコハク酸、無水2−ドデセニルコハク酸、無水ウンデセニルコハク酸、及びこれらの組合せから成る群から選択された無水物と重縮合させ、不飽和ポリエステルを回収するステップを含むプロセス。
【選択図】なし
Description
プロポキシ化ビスフェノールAとフマル酸から誘導される不飽和ポリエステル樹脂は、当業者の認識範囲内にある。
以下の式2に示す化学式を有する。
II
III
(2)
式中、Rは芳香族部分、R’は水素又はアルキル、そしてaはゼロ、1、又は2、或はゼロ、1、及び2の混合である。結果として得られるポリアルコキシジオールは次に、約0.95乃至約1.05モル当量の量のジカルボン酸と重縮合することができる。
II
III
(1)
式中、aはゼロ、1、又は2、或はゼロ、1、及び2の混合である。結果として得られるポリアルコキシジオールは次に、約0.95乃至約1.05モル当量の量のジカルボン酸と重縮合することができる。
選択することができるワックスには、例えば、重量平均分子量が約500乃至約20,000、実施形態においては約1,000乃至約10,000のワックスが含まれる。
Claims (4)
- 有機ジオールを、炭酸アルカリの第1の触媒の存在下で、環状炭酸アルキレンと反応させてポリアルコキシジオールを形成し、
随意に前記ポリアルコキシジオールを、アルカリアルコキシドの第2の触媒の存在下で、追加量の環状炭酸アルキレンと接触させて混合物を形成し、
得られた前記混合物を、ジカルボン酸、並びに、無水マレイン酸、無水トリメリト酸、無水ドデセニルコハク酸、無水2−ドデセニルコハク酸、無水ウンデセニルコハク酸、及びこれらの組合せから成る群から選択された無水物、と重縮合させ、
不飽和ポリエステルを回収する、
ステップを含むことを特徴とするプロセス。 - 前記反応は、約160℃乃至約215℃の温度で加熱することにより遂行され、前記重縮合は、約185℃乃至約225℃の温度で約1時間乃至約5時間の間加熱し、次いで前記混合物の圧力を約760トルから約1トルまで、約1時間乃至約6時間にわたって低下させることにより遂行され、前記重縮合に引き続いて前記反応混合物は約22℃乃至約40℃の温度まで冷却されることを特徴とする、請求項1に記載のプロセス。
- 1,2-プロパンジオール、1,3-プロパンジオール、1,3-ブタンジオール、ペンチレングリコール、ヘキシレングリコール、ジフェノール、ネオペンチルグリコール、ジエチレングリコール、ジプロピレングリコール、2,2−ビス-(4−ヒドロキシフェニル)プロパン、2,2−ビス-(3−ヒドロキシフェニル)プロパン、2,2−ビス-(2−ヒドロキシフェニル)プロパン、2,2−ビス-(3−ヒドロキシフェニル)プロパン、2,2−ビス-(5−ヒドロキシフェニル)プロパン、ビスフェノールA、エトキシ化ビスフェノールA、ビス-(4−ヒドロキシフェニル)メタン、1,1−ビス-(4−ヒドロキシフェニル)エタン、シス-1,4−ジヒドロキシ-シクロヘキサン、トランス-1,4−ジヒドロキシ-シクロヘキサン、シス-1,2−ジヒドロキシ-シクロヘキサン、トランス-1,2−ジヒドロキシ-シクロヘキサン、トランス-1,3−ジヒドロキシ-シクロヘキサン、シス-1,3−ジヒドロキシ-シクロヘキサン、及びそれらの組合せから成る群から選択された有機ジオールを、炭酸アルカリの第1の触媒の存在下で、炭酸エチレン、炭酸プロピレン、炭酸ブチレン、及びそれらの組合せから成る群から選択された環状炭酸アルキレンと反応させてポリアルコキシジオールを形成し、
前記ポリアルコキシジオールを、アルカリアルコキシドの第2の触媒の存在下で、追加量の環状炭酸アルキレンと接触させて混合物を形成し、
得られた前記混合物を、ジカルボン酸、並びに、無水マレイン酸、無水トリメリト酸、無水n−ドデセニルコハク酸、無水2−ドデセニルコハク酸、無水2−ウンデセニルコハク酸、及びそれらの組合せから成る群から選択された無水物、と重縮合させ、
不飽和ポリエステルを回収する、
ステップを含み、
前記ジカルボン酸及び前記無水物は、約0.90モル当量乃至約1.1モル当量の組み合せた量で用いられる、
ことを特徴とするプロセス。 - 1,2-プロパンジオール、1,3-プロパンジオール、1,3-ブタンジオール、ペンチレングリコール、ヘキシレングリコール、ジフェノール、ネオペンチルグリコール、ジエチレングリコール、ジプロピレングリコール、2,2−ビス-(4−ヒドロキシフェニル)プロパン、2,2−ビス-(3−ヒドロキシフェニル)プロパン、2,2−ビス-(2−ヒドロキシフェニル)プロパン、2,2−ビス-(3−ヒドロキシフェニル)プロパン、2,2−ビス-(5−ヒドロキシフェニル)プロパン、ビスフェノールA、エトキシ化ビスフェノールA、ビス-(4−ヒドロキシフェニル)メタン、1,1−ビス-(4−ヒドロキシフェニル)エタン、シス-1,4−ジヒドロキシ-シクロヘキサン、トランス-1,4−ジヒドロキシ-シクロヘキサン、シス-1,2−ジヒドロキシ-シクロヘキサン、トランス-1,2−ジヒドロキシ-シクロヘキサン、トランス-1,3−ジヒドロキシ-シクロヘキサン、シス-1,3−ジヒドロキシ-シクロヘキサン、及びそれらの組合せから成る群から選択された有機ジオールを、炭酸アルカリの第1の触媒の存在下で、炭酸エチレン、炭酸プロピレン、炭酸ブチレン、及びそれらの組合せから成る群から選択された環状炭酸アルキレンと反応させてポリアルコキシジオールを形成し、
随意に前記ポリアルコキシジオールを、アルカリアルコキシドの第2の触媒の存在下で、追加量の環状炭酸アルキレンと接触させて混合物を形成し、
得られた前記混合物を、ジカルボン酸、並びに、無水マレイン酸、無水トリメリト酸、無水n−ドデセニルコハク酸、無水2−ドデセニルコハク酸、無水2−ウンデセニルコハク酸、及びそれらの組合せから成る群から選択された無水物、と重縮合させ、
不飽和ポリエステルを回収し、
前記不飽和ポリエステルを、随意の着色剤、随意の界面活性剤、及び随意のワックスと接触させて小粒子を形成し、
前記小粒子を凝集させ、
前記小粒子を融合させてトナー粒子を形成し、
前記トナー粒子を回収する、
ステップを含むことを特徴とするプロセス。
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