TW523525B - Process for preparing hydroxy-functionalized polyesters - Google Patents
Process for preparing hydroxy-functionalized polyesters Download PDFInfo
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- TW523525B TW523525B TW087114996A TW87114996A TW523525B TW 523525 B TW523525 B TW 523525B TW 087114996 A TW087114996 A TW 087114996A TW 87114996 A TW87114996 A TW 87114996A TW 523525 B TW523525 B TW 523525B
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- 229920000728 polyester Polymers 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 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 11
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 8
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 21
- -1 12-undecanoic acid Chemical compound 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 11
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 230000002079 cooperative effect Effects 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- 229910052742 iron Inorganic materials 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 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 2
- 150000001875 compounds Chemical class 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 235000021317 phosphate Nutrition 0.000 claims 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- QTAFORZADPHKBK-UHFFFAOYSA-N 1,2-bis(oxiran-2-ylmethyl)hydrazine Chemical compound C(C1CO1)NNCC1CO1 QTAFORZADPHKBK-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 1
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 claims 1
- QFIBYDXUIPAATK-UHFFFAOYSA-N 4-[7-(4-hydroxyphenyl)pyren-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC2=CC=C(C=C(C=C3C=C4)C=5C=CC(O)=CC=5)C3=C2C4=C1 QFIBYDXUIPAATK-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 claims 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 150000003891 oxalate salts Chemical class 0.000 claims 1
- OHFDBBFDFZXHJQ-UHFFFAOYSA-N phenylarsane Chemical compound [AsH2]C1=CC=CC=C1 OHFDBBFDFZXHJQ-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- GZQBGAMLHSVJRT-UHFFFAOYSA-N n-(9h-fluoren-1-yl)-9h-fluoren-1-amine Chemical compound C1C2=CC=CC=C2C2=C1C(NC=1C=CC=C3C4=CC=CC=C4CC=13)=CC=C2 GZQBGAMLHSVJRT-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001409 amidines Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 210000004513 dentition Anatomy 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
Classifications
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- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4292—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with monocarboxylic acids
-
- 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
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
523525 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（1 ) 本發明有關製備羥基-官能化聚酯之方法。 在美國專利第5，171，820號已知製備羥基-官能化聚酯 ，其藉由將二羧酸及二甘縮水甘油醚在有四級齒化銨為起 始劑的溶劑中反應。此專利教示可在回收產物前加入單官 忐羧酸以消耗殘餘的環氧官能基，因其在樹脂製成物件基 間將導致交聯。當此此方法產生高分子量熱塑性羥基官能 化聚醋，產品之回收需要羥基官能化聚酯之分離，不論是 由非溶劑中沉澱或由溶劑中揮發，其等皆需要拋棄或再生 大量之溶劑。 明顯的需要一熔融反應製程以消除在製備熱塑性羥基 官能化聚酯中溶劑的需求。然而，先前在熔融製程中製備 羥基官能化聚酯之努力涉及不實用之緩慢低溫方法，其需 要之反應時間超過4至8小時以製造具合宜分子量的聚合物 。例如參考Kleen 等人之p〇iymer Buiietin，1995, Vol· 35 第79-85頁。此外，由此方法產生之羥基官能化聚酯當再 加熱時交聯，如在此文獻之表丨中所述，因此其並非真的 熱塑性。 ~ 需要提供製備羥基-官能化聚酯之方法，其消除溶劑 的需求，且同時產生熔融安定、熱塑性羥基官能化聚酯。 本發明一目的為一種製備熱塑性羥基-官能化聚酯之 方法’其包含在-單官能基魏及催化劑存在但無溶劑存 在下，於足以形羥基官能化之聚酯的狀況下，將二羧酸或 二羧酸混合物與二環氧化物接觸。 經由本發明方法製備之聚（羥基酯醚）具有以下式表示
本纸浪尺度適财關家轉（CNS (請先閱讀背面之注意事項再填寫本頁)
-4 - 523525 A7 B7 五 _—_ 經濟部中央標準局員工消費合作社印製 發明説明（ 之重複單元： 0 0 ，〇C—rLC〇R3〇R4〇_j^ 其中R1分別代表一二價有機基，其主要為烴烯，或不同之 主要為烴烯的有機官能基之組合；R3為 0H I -ch2cch2- 或 ch2oh -c—ch2-o—— 和 R4為 Ο 〇 II 6 II -C—R—C- 或
0H 〇ch2cch2or- R5 η 其中R2為主要為烴烯之二價有機基、或 -H2CfHC-H2C-〇 R7
•Ο—ch2-ch]-ch2- Η V為氫或烧基；R6各自為有機基，其主要為烴烯；R7 各自為氫或甲基；且X及y各自為〇至100之整數。 「主要烴烯」為定義主要為烴之二價基團，但其可選 擇的含有少量雜原子基如氧、硫、亞胺、颯及亞颯。 可用為R1、R2及R6之代表性二價有機基團包括亞烷基 、環烯基、亞烷芳撐基、聚（亞烷氧基亞烷基）、亞烷基硫 亞烷基、亞烧基楓亞烧基、以至少一羥基取代之亞烧基、 本紙張尺度適用中國國家標隼（CNS ) Λ4燒格（210Χ29ϋ1 523525 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（3 ) 以至少一羥基取代之環烯基、以至少一羥基取代之亞烷芳 撐基、以至少一羥基取代之聚（亞烷氧基亞烷基）、以至少 一羥基取代之亞烷基硫亞烷基、以至少一羥基取代之亞烷 基颯亞烷基、芳撐基、二亞烷基芳撐基、二芳撐基酮、二 芳撐基颯、二芳撐氧化物及二芳撐硫化物。 在較佳之羥基官能化聚酯中，R1、R2及R6各自為亞甲 基、亞乙基、亞丙基、亞丁基、五亞甲基、六亞甲基、七 亞甲基、八亞甲基、九亞曱基、十亞甲基、十二亞甲基、 M-環己烯、1，3-環己烯或1,2-環己烯，其等可選擇的以至 少一羥基取代，p-亞苯基、m-亞苯基、2,6-萘、二亞苯基· 異亞丙烯基、颯二亞苯基、羰二亞苯基、氧二亞苯基或9,9-勿一亞苯基’且η為0至100。 在較佳之羥基官能化聚酯中，Rl、R2及R6各自為亞烷 基、環烯基、亞烷芳撐基、聚（亞烷氧基亞烷基）、亞烷基 醯胺基亞烷基、聚（亞烷醯胺基亞烷基）、亞烷基硫基亞烷 基、聚（亞烧硫基亞烧基）、亞烧基现基亞烧基、聚（亞烧 礙基亞烷基）、任何其等可選擇的以至少一羥基取代，芳 撐基、二亞烧基芳撐基、二芳撐基酮、二芳撐基氧化物、 一亞芳烯-二芳撐基、二芳撐硫化物或此些基團之組合。 在較佳聚合物中，R1為亞乙基、亞丙基、亞丁基、五 亞甲基、六亞曱基、七亞曱基、八亞曱基、九亞甲基、十 亞甲基、十二亞甲基、1，4-環己烯、ι，3_環己烯或i，2-環己 稀’其等可選擇的以至少一羥基取代；R2&R6各自為亞甲 基、亞乙基、亞丙基、亞丁基、五亞甲基、六亞甲基、七 (請先閱讀背面之注意事項再填寫本頁 4 、11 .曛 本紙張尺度適用巾@11家彳婢（CNS ) Λ4\ 2)ΟΧ297.λ> ^"7 5 2 5 3 2 5 Χ-- 經濟部^ψ!標準局員工消費合作社印51 A7 ^_：____ B7 發明説明（4) 亞甲基、八亞甲基、九亞甲基、十亞甲基、十二亞甲基、 1’4環己烯、ι，3-環己婦或ι，2_環己烯，其等可選擇的以至 少一羥基取代。 更佳地，R1及R6為由下式表示
^ R R 且R2以下式表示
4hc-h2c-o^_hc-h2c-o-ch2--ch-(o-ch2-chA-R8 ^ ^ 2.8T 其中R8各自為氫或甲基且\及^各自為〇至1〇〇。 在更佳聚合物中，R1及R6各自為亞乙基、亞丁基、六 亞甲基、m-亞苯基、p-亞苯基或2,6_萘；R2各自為…亞苯 基、P-亞苯基、萘、二亞苯基_異亞丙烯基、颯二亞苯基 、魏二亞苯基、氧二亞苯基或9,9_芴二亞苯基；R5為氫； 且R7各自為苯基、甲基或 CH3-(CH2)m- 其中m為1至30。 通常，本發明之聚合物之製備可經由在一單官能基魏 酸及催化劑存在但無溶劑存在下，於足以形羥基官能化之 聚酯的狀況下，將二羧酸或二羧酸混合物與二環氧化物反 應。 可用以實施本發明之二羧酸包括丁二酸、己二酸、辛 二酸、癸二酸、1，1〇-癸烷二羧酸、U2-十二烷二羧酸、M-環己烷二羧酸、二羥丁二酸、對苯二甲酸及異間笨二甲酸
本紙浪尺度適用中國國家標隼（CNS ) Λ4^格（’2i〇X2tmH
(梦先閱讀背面之注意事項再.填寫本1TC
-7 - 523525 A7 B7 五 、發明説明（6 ^有之任何特定反應物及催㈣。通常，反應在非氧化氣 ^下仃，如氮或其他惰性氣體外圍下進行。反應為純淨進 行（黑溶劑或其他稀釋劑）。 本發明之方法可在一開放容器中、或在一播壓機或在 一射出型機中進行。 下列實施例為用以說明之用而非用以限制本發明之範 圍。除非特別指明，所有之份或百分比為重量份或重量百 分比。 實施例1 雙盼A-二縮水甘油醚（環氧當量重=171.19 ; 20.0 g， 0.〇58莫耳）、己二酸（8 54 g，〇 〇58莫耳）、苯甲酸（〇 i4 g ，〇·〇1當量）及四丁基銨溴化物（0·76 g，〇 〇〇2莫耳）之混合 在4盎斯罐中機械攪拌並以一爐架加熱至外罩温度為15〇 至160 C。當反應物熔融及溶解，反應混合之溫度放熱上 升至164C，然後該攪拌熔融物維持在14〇它。在反應開始 溶於二曱基曱醯胺（DMF)、並因而未交聯後，於不同間隔 時間（參閱表1)取出試樣，其具有下列特徵： (請先閲讀背面之注意# 4 項再填」 裝— 寫本頁) 4 經濟部中央標準局員工消費合作社印製 表 1 反應時間，分鐘 Mwa Mna U/gi 5 43,770 11899 0.37 10 56011 13.577 90.41 120 146,387 13,622 0.54 相對於苯乙烯標準的凝膠層析測定 b為〇·5 g試樣於100 ml DMF中於25°C測定之特性黏度 本紙張尺度適用中國國家標隼（CNS ) A4ML格（:210X297公筇~)—~ 一一"
Claims (1)
- 523525 A8B8C8D8 一圍 一範 I利 I 專 請 中 六 I 第87114996號專利再審查案申請專利範圍修正本 修正曰期：9〇年8月 1 · 一種製造熱塑性羥基官能化聚酯的方法，其包含將一 二羧酸或二羧酸混合物與一二環氧化物在一單 酸及一催化劑存在但無溶劑存在下，於一足以形成声 基官能化聚酯之狀況下接觸，其中該二羧酸為丁二酸 、己二酸、辛二酸、癸二酸、1，10_癸烷二羧酸、丨12_ 十一烧二竣酸、1，4-環己烧二叛酸、二經丁二酸、對 苯二甲酸及異間苯二甲酸，該二環氧化物為二氫酚之 二縮水甘油醚或二羧酸之二縮水甘油醚，且該催化巧 為鐵催化劑。 2·如申請專利範圍第1項之方法，其中該二環氧化物為一 環氧樹脂為雙酚A之二縮水甘油醚；4,4，-颯二盼· 4 氧基二酚；4,4，-二羥基苯並酚酮；間苯二酚；9,9、雙（4 羥苯基）芴；4,4’-二羥基雙酚或4,4-‘_二經基_〜甲基均 二苯代乙烯及前述及之二羧酸的二縮水甘油酯。 3·如申請專利範圍第丨項之方法，其中該二羧酸為丁二酸 、己二酸、辛二酸、癸二酸、ijO·癸烷二羧酸、1 1孓 十二烧二羧酸、丨，‘環己烷二羧酸、二羥丁二酸、對 苯二曱酸及異間苯二甲酸。 4.如申請專利範圍第丨項之方法，其中該二縮水甘油崎或 二縮水甘油酯具有環氧當量重為100至4000。 5·如申請專利範圍第旧之方法，其中該鏘催化劑為鱗或 銨鹽催化劑。 本紙張尺錢巾自國家標準（CNS)A4規格721G X 297公爱） (請先閱讀背面之ί事項 裝— 寫本頁) 經濟部智慧財產局員工消費合作社印製 523525 六、申請專利範圍 6.如申+請專利範圍第5項之方法，其中該鐵催化劑為乙烤 二苯基鱗魏物、四苯基㈣化物及四肆（η-丁基）錄 溴化物、氯化物、蛾化物、漠化物、酸鹽、磷酸鹽、 曱酸鹽、磷酸鹽、爛酸鹽、三氣醋酸鹽、草酸鹽及碳 咖° '如申請專利範圍第6項之方法，其中該鐵催化劑為四肆 (η-丁基）銨溴化物。 δ·如申請專利範圍1項之方法，其中該催化劑之存在量為 在反應混合物中之二鲮酸的莫耳數之0.001至10莫耳百 分比。 9.如申請專利範圍第旧之方法，其中該官缺酸為錯酸 丙酸或苯曱酸。 10· —種聚（羥酯醚），其係以申請專利範圍第i項之方法所 製備。 11. 一種製造熱塑性羥基官能化聚酯的方法，其包含將一 二緩酸或二羧酸混合物與一二環氧化物在一單官能A 酸及一催化劑存在但無溶劑存在下，於l5(rc至16〇 下接觸直至反應混合物熔融。 經濟部智慧財產局員工消費合作社印1 適 度 尺一張 一紙 本 110一格一規 4 A IS) N (C 準標一國一國 ¾ 公 97
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/926,954 US5852163A (en) | 1997-09-10 | 1997-09-10 | Process for preparing hydroxy-functionalized polyesters |
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| Publication Number | Publication Date |
|---|---|
| TW523525B true TW523525B (en) | 2003-03-11 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| TW087114996A TW523525B (en) | 1997-09-10 | 1998-09-09 | Process for preparing hydroxy-functionalized polyesters |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5852163A (zh) |
| EP (1) | EP1015508A1 (zh) |
| JP (1) | JP2001515935A (zh) |
| KR (1) | KR20010023832A (zh) |
| CN (1) | CN1269812A (zh) |
| AR (1) | AR017081A1 (zh) |
| BR (1) | BR9812192A (zh) |
| CA (1) | CA2303369A1 (zh) |
| PL (1) | PL339253A1 (zh) |
| TW (1) | TW523525B (zh) |
| WO (1) | WO1999012991A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2172186T3 (es) * | 1997-09-05 | 2002-09-16 | Dow Chemical Co | Emulsiones de alta relacion de fase interna y dispersiones acuosas estables de polimeros con funcion hidroxilica. |
| US5962621A (en) * | 1998-04-28 | 1999-10-05 | The Dow Chemical Company | Process for preparing hydroxy-functionalized polyesters |
| AU1952401A (en) * | 1999-12-08 | 2001-06-18 | Dow Global Technologies Inc. | Architectural concrete having a reinforcing polymer and process to make same |
| US6346596B1 (en) | 2000-07-14 | 2002-02-12 | Valspar Corporation | Gas barrier polymer composition |
| KR100970837B1 (ko) | 2007-02-20 | 2010-07-16 | 주식회사 엘지화학 | 플로렌계 수지 중합체 및 이를 포함하는 네가티브형 감광성수지 조성물 |
| US9023972B2 (en) | 2010-01-25 | 2015-05-05 | University of Pittsburgh—of the Commonwealth System of Higher Education | Polyesters, methods of making polyesters and uses therefor |
| JP2014530919A (ja) * | 2011-09-02 | 2014-11-20 | サン ケミカル コーポレイション | 直鎖型ポリエステル樹脂および改良された平版インク |
| CN102585183A (zh) * | 2012-02-23 | 2012-07-18 | 北京理工大学 | 一种羟基官能化聚酯/蒙脱土纳米复合材料的制备方法 |
| WO2015051257A1 (en) | 2013-10-04 | 2015-04-09 | Zephyros, Inc. | Method and apparatus for forming and adhering panel and bracket structures |
| WO2015051242A1 (en) | 2013-10-04 | 2015-04-09 | Zephyros, Inc. | Method and apparatus for adhesion of inserts |
| US9796891B2 (en) | 2014-08-11 | 2017-10-24 | Zephyros, Inc. | Panel edge enclosures |
| EP3194162B1 (en) | 2014-08-14 | 2022-11-02 | Zephyros Inc. | Reformable epoxy resin for composites |
| EP3374412A1 (en) | 2015-11-12 | 2018-09-19 | Zephyros Inc. | Controlled glass transition polymeric material and method |
| CN106674509B (zh) * | 2016-12-23 | 2019-06-14 | 合肥乐凯科技产业有限公司 | 一种高表面张力及硬度的光学聚酯膜 |
| JP7408047B2 (ja) * | 2018-07-31 | 2024-01-05 | 日産化学株式会社 | レジスト下層膜形成組成物 |
| US11673995B2 (en) * | 2019-08-08 | 2023-06-13 | Ppg Industries Ohio, Inc. | Polyol polymers, methods of preparing such polymers, and coating compositions containing the same |
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| US4612156A (en) * | 1985-02-26 | 1986-09-16 | The Dow Chemical Company | Solventless process for producing resinous materials |
| US5171820A (en) * | 1991-05-13 | 1992-12-15 | The Dow Chemical Company | Hydroxy-functional polyesters as thermoplastic barrier resins |
| US5134201A (en) * | 1991-10-28 | 1992-07-28 | The Dow Chemical Company | Miscible polyester blends |
| US5496910A (en) * | 1994-07-21 | 1996-03-05 | The Dow Chemical Company | Hydroxyfunctional thermoplastic polyesters |
-
1997
- 1997-09-10 US US08/926,954 patent/US5852163A/en not_active Expired - Fee Related
-
1998
- 1998-08-14 WO PCT/US1998/016953 patent/WO1999012991A1/en not_active Ceased
- 1998-08-14 EP EP98940908A patent/EP1015508A1/en not_active Withdrawn
- 1998-08-14 JP JP2000510792A patent/JP2001515935A/ja active Pending
- 1998-08-14 CN CN98809018A patent/CN1269812A/zh active Pending
- 1998-08-14 CA CA002303369A patent/CA2303369A1/en not_active Abandoned
- 1998-08-14 BR BR9812192-8A patent/BR9812192A/pt not_active IP Right Cessation
- 1998-08-14 PL PL98339253A patent/PL339253A1/xx unknown
- 1998-08-14 KR KR1020007002507A patent/KR20010023832A/ko not_active Withdrawn
- 1998-09-09 AR ARP980104498A patent/AR017081A1/es not_active Application Discontinuation
- 1998-09-09 TW TW087114996A patent/TW523525B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1015508A1 (en) | 2000-07-05 |
| AR017081A1 (es) | 2001-08-22 |
| CA2303369A1 (en) | 1999-03-18 |
| KR20010023832A (ko) | 2001-03-26 |
| WO1999012991A1 (en) | 1999-03-18 |
| BR9812192A (pt) | 2000-07-18 |
| JP2001515935A (ja) | 2001-09-25 |
| CN1269812A (zh) | 2000-10-11 |
| US5852163A (en) | 1998-12-22 |
| PL339253A1 (en) | 2000-12-04 |
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