AU2008256956B2 - Reversible derivatization of poly (aryl ether ketones) - Google Patents
Reversible derivatization of poly (aryl ether ketones) Download PDFInfo
- Publication number
- AU2008256956B2 AU2008256956B2 AU2008256956A AU2008256956A AU2008256956B2 AU 2008256956 B2 AU2008256956 B2 AU 2008256956B2 AU 2008256956 A AU2008256956 A AU 2008256956A AU 2008256956 A AU2008256956 A AU 2008256956A AU 2008256956 B2 AU2008256956 B2 AU 2008256956B2
- Authority
- AU
- Australia
- Prior art keywords
- ether
- poly
- paek
- dithioacetal
- thioacetal
- 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.)
- Ceased
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- -1 poly (aryl ether ketones Chemical class 0.000 title claims abstract description 190
- 230000002441 reversible effect Effects 0.000 title claims abstract description 11
- 238000001212 derivatisation Methods 0.000 title description 4
- 229920006260 polyaryletherketone Polymers 0.000 claims abstract description 119
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 82
- 239000002904 solvent Substances 0.000 claims abstract description 62
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 17
- 230000007928 solubilization Effects 0.000 claims abstract description 11
- 238000005063 solubilization Methods 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 279
- 229920002530 polyetherether ketone Polymers 0.000 claims description 117
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 85
- 229920000642 polymer Polymers 0.000 claims description 85
- 150000003555 thioacetals Chemical class 0.000 claims description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
- 229920001652 poly(etherketoneketone) Polymers 0.000 claims description 33
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 32
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 30
- 239000000835 fiber Substances 0.000 claims description 30
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 claims description 29
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 229920001660 poly(etherketone-etherketoneketone) Polymers 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 125000001382 thioacetal group Chemical group 0.000 claims description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 15
- 229960001701 chloroform Drugs 0.000 claims description 13
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 11
- 229960004132 diethyl ether Drugs 0.000 claims description 11
- 239000002841 Lewis acid Substances 0.000 claims description 10
- 238000009826 distribution Methods 0.000 claims description 10
- 150000007517 lewis acids Chemical class 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- ANGGPYSFTXVERY-UHFFFAOYSA-N 2-iodo-2-methylpropane Chemical compound CC(C)(C)I ANGGPYSFTXVERY-UHFFFAOYSA-N 0.000 claims description 7
- 150000008378 aryl ethers Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 229920013657 polymer matrix composite Polymers 0.000 claims description 7
- 239000011160 polymer matrix composite Substances 0.000 claims description 7
- 150000004252 dithioacetals Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229940117389 dichlorobenzene Drugs 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims description 3
- 150000004662 dithiols Chemical class 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 claims 14
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims 14
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 claims 14
- 239000004696 Poly ether ether ketone Substances 0.000 claims 6
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 claims 6
- 229920006324 polyoxymethylene Polymers 0.000 claims 4
- 235000010290 biphenyl Nutrition 0.000 claims 3
- 239000004305 biphenyl Substances 0.000 claims 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 238000012512 characterization method Methods 0.000 abstract description 48
- 238000010511 deprotection reaction Methods 0.000 abstract description 31
- 238000006719 thioacetalization reaction Methods 0.000 abstract description 28
- 238000004458 analytical method Methods 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 10
- 230000015556 catabolic process Effects 0.000 abstract description 7
- 238000006731 degradation reaction Methods 0.000 abstract description 7
- 238000012545 processing Methods 0.000 abstract description 6
- 238000007385 chemical modification Methods 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 3
- 230000004048 modification Effects 0.000 abstract description 3
- 230000001066 destructive effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 36
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 34
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 22
- 238000005259 measurement Methods 0.000 description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 15
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 14
- 238000000149 argon plasma sintering Methods 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 11
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000006359 acetalization reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 2
- 229920004695 VICTREX™ PEEK Polymers 0.000 description 2
- 125000004036 acetal group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000000120 microwave digestion Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229920001657 poly(etheretherketoneketone) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000012667 polymer degradation Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 101100379068 Caenorhabditis elegans apc-2 gene Proteins 0.000 description 1
- 101100395863 Caenorhabditis elegans hst-2 gene Proteins 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001104043 Syringa Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000004192 high performance gel permeation chromatography Methods 0.000 description 1
- 238000012781 high pressure - size exclusion chromatography Methods 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229940035658 visco-gel Drugs 0.000 description 1
- 238000005303 weighing 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3342—Polymers modified by chemical after-treatment with organic compounds containing sulfur having sulfur bound to carbon and hydrogen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2381/02—Polythioethers; Polythioether-ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0709815.5A GB0709815D0 (en) | 2007-05-22 | 2007-05-22 | Reversible derivation of poly (aryl ether ketones) |
| GB0709815.5 | 2007-05-22 | ||
| PCT/US2008/063822 WO2008147722A1 (en) | 2007-05-22 | 2008-05-16 | Reversible derivatization of poly (aryl ether ketones) |
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| WO (1) | WO2008147722A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0709815D0 (en) * | 2007-05-22 | 2007-07-04 | Cytec Tech Corp | Reversible derivation of poly (aryl ether ketones) |
| EP2393856B1 (en) | 2009-02-05 | 2016-04-06 | Arkema Inc. | Fibers sized with polyetherketoneketones |
| DE102013200201A1 (de) * | 2013-01-09 | 2014-07-10 | Perpetuum-Ebner Gmbh & Co. Kg | Silyliertes Polyaryletherketon und Verfahren zu dessen Herstellung |
| GB2526243B (en) * | 2014-02-24 | 2021-07-14 | Victrex Mfg Ltd | Polymeric materials |
| US10688770B2 (en) | 2015-03-03 | 2020-06-23 | Ricoh Co., Ltd. | Methods for solid freeform fabrication |
| US9695280B2 (en) | 2015-03-03 | 2017-07-04 | Ricoh Co., Ltd. | Methods for solid freeform fabrication |
| US10066119B2 (en) | 2015-03-03 | 2018-09-04 | Ricoh Co., Ltd. | Method for solid freeform fabrication |
| US9808993B2 (en) | 2015-03-03 | 2017-11-07 | Ricoh Co., Ltd. | Method for solid freeform fabrication |
| CN105954078B (zh) * | 2016-05-11 | 2018-10-12 | 上海瀚海检测技术股份有限公司 | 一种聚醚醚酮复合材料中聚醚醚酮的定量分析方法 |
| CN111875791A (zh) * | 2020-08-31 | 2020-11-03 | 中国科学院长春应用化学研究所 | 一种聚芳醚酮树脂的制备方法 |
| EP4039730A1 (en) * | 2021-02-08 | 2022-08-10 | Technische Universität Berlin | Process for modifying an aromatic polyether backbone and a modified polyether obtained by this process |
| JP7521110B2 (ja) * | 2021-03-25 | 2024-07-23 | 旭化成株式会社 | ポリアリーレンエーテルケトン樹脂、その製造方法、及び成形品 |
| CN113583426B (zh) * | 2021-09-09 | 2022-10-14 | 东华大学 | 一种碳纤维/聚醚酮酮复合材料的制备方法 |
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| US4882397A (en) * | 1986-12-05 | 1989-11-21 | Amoco Corporation | Method for converting polyketals to polyaryletherketones in the presence of a metal salt |
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| US5093460A (en) * | 1982-09-30 | 1992-03-03 | Amoco Corporation | Monomers and polyketal polymers from such monomers |
| JPS6163673A (ja) * | 1984-09-05 | 1986-04-01 | Rikagaku Kenkyusho | アンチ−１，３−ポリオ−ル化合物及びその合成法 |
| US4616056A (en) * | 1985-05-16 | 1986-10-07 | Raychem Corporation | Poly(aryl ether ketones) containing sulfur |
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| GB0709815D0 (en) * | 2007-05-22 | 2007-07-04 | Cytec Tech Corp | Reversible derivation of poly (aryl ether ketones) |
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2007
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2008
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- 2008-05-16 EP EP08755634.6A patent/EP2152780B1/en not_active Not-in-force
- 2008-05-16 CN CN200880016972.2A patent/CN101730715B/zh not_active Expired - Fee Related
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- 2008-05-16 CA CA2687828A patent/CA2687828C/en not_active Expired - Fee Related
- 2008-05-16 KR KR1020097026540A patent/KR101571173B1/ko not_active Expired - Fee Related
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4882397A (en) * | 1986-12-05 | 1989-11-21 | Amoco Corporation | Method for converting polyketals to polyaryletherketones in the presence of a metal salt |
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| KR20100031576A (ko) | 2010-03-23 |
| US20180030227A1 (en) | 2018-02-01 |
| CA2687828A1 (en) | 2008-12-04 |
| JP5506666B2 (ja) | 2014-05-28 |
| US9828478B2 (en) | 2017-11-28 |
| JP2010528157A (ja) | 2010-08-19 |
| GB0809349D0 (en) | 2008-07-02 |
| GB2449750A (en) | 2008-12-03 |
| GB0709815D0 (en) | 2007-07-04 |
| GB2449750B (en) | 2012-02-01 |
| MX2009012344A (es) | 2009-12-04 |
| AU2008256956A1 (en) | 2008-12-04 |
| CN101730715A (zh) | 2010-06-09 |
| KR101571173B1 (ko) | 2015-12-04 |
| WO2008147722A1 (en) | 2008-12-04 |
| US20160075840A1 (en) | 2016-03-17 |
| EP2152780B1 (en) | 2017-09-06 |
| US9963563B2 (en) | 2018-05-08 |
| US20110040045A1 (en) | 2011-02-17 |
| CA2687828C (en) | 2012-10-30 |
| CN101730715B (zh) | 2014-06-11 |
| EP2152780A1 (en) | 2010-02-17 |
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