WO2017214055A1 - Full scale process for preparing polymer powders - Google Patents
Full scale process for preparing polymer powders Download PDFInfo
- Publication number
- WO2017214055A1 WO2017214055A1 PCT/US2017/035997 US2017035997W WO2017214055A1 WO 2017214055 A1 WO2017214055 A1 WO 2017214055A1 US 2017035997 W US2017035997 W US 2017035997W WO 2017214055 A1 WO2017214055 A1 WO 2017214055A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- resin solution
- methyl
- mixture
- polymer
- Prior art date
Links
- 239000000843 powder Substances 0.000 title claims abstract description 119
- 229920000642 polymer Polymers 0.000 title claims abstract description 71
- 238000004519 manufacturing process Methods 0.000 title abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 108
- 229920005989 resin Polymers 0.000 claims abstract description 108
- 239000002904 solvent Substances 0.000 claims abstract description 96
- 238000001556 precipitation Methods 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 239000002244 precipitate Substances 0.000 claims abstract description 29
- 238000001035 drying Methods 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 19
- 239000002952 polymeric resin Substances 0.000 claims abstract description 12
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 150
- 239000000243 solution Substances 0.000 claims description 93
- 229920002312 polyamide-imide Polymers 0.000 claims description 38
- 239000004962 Polyamide-imide Substances 0.000 claims description 36
- 230000008569 process Effects 0.000 claims description 34
- 239000002245 particle Substances 0.000 claims description 33
- 238000013019 agitation Methods 0.000 claims description 30
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 30
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 24
- 238000005406 washing Methods 0.000 claims description 24
- 239000012296 anti-solvent Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- -1 polyarylsulfones Polymers 0.000 claims description 21
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 20
- 238000005507 spraying Methods 0.000 claims description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 14
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 14
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 10
- 229940116333 ethyl lactate Drugs 0.000 claims description 10
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002861 polymer material Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 7
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 7
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 7
- 229940011051 isopropyl acetate Drugs 0.000 claims description 7
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 7
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 7
- 229940017144 n-butyl lactate Drugs 0.000 claims description 7
- 229920002530 polyetherether ketone Polymers 0.000 claims description 7
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 7
- OIKFIOGYFGWPAB-UHFFFAOYSA-N 1-(3-methoxypropyl)pyrrolidin-2-one Chemical class COCCCN1CCCC1=O OIKFIOGYFGWPAB-UHFFFAOYSA-N 0.000 claims description 6
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 claims description 6
- DLEWDCPFCNLJEY-UHFFFAOYSA-N 1-morpholin-4-ylpropan-1-one Chemical compound CCC(=O)N1CCOCC1 DLEWDCPFCNLJEY-UHFFFAOYSA-N 0.000 claims description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002780 morpholines Chemical class 0.000 claims description 6
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 claims description 6
- WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 claims description 5
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000004693 Polybenzimidazole Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 5
- 229940093499 ethyl acetate Drugs 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 5
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 5
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 5
- 229940057867 methyl lactate Drugs 0.000 claims description 5
- 229920005575 poly(amic acid) Polymers 0.000 claims description 5
- 229920002492 poly(sulfone) Polymers 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920002480 polybenzimidazole Polymers 0.000 claims description 5
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 claims description 5
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 229920002873 Polyethylenimine Polymers 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- WHIRALQRTSITMI-UJURSFKZSA-N (1s,5r)-6,8-dioxabicyclo[3.2.1]octan-4-one Chemical compound O1[C@@]2([H])OC[C@]1([H])CCC2=O WHIRALQRTSITMI-UJURSFKZSA-N 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical class CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 claims description 3
- IVUYGANTXQVDDG-UHFFFAOYSA-N 1-(2-methylpropyl)pyrrolidin-2-one Chemical compound CC(C)CN1CCCC1=O IVUYGANTXQVDDG-UHFFFAOYSA-N 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 3
- NNFAFRAQHBRBCQ-UHFFFAOYSA-N 1-pentylpyrrolidin-2-one Chemical compound CCCCCN1CCCC1=O NNFAFRAQHBRBCQ-UHFFFAOYSA-N 0.000 claims description 3
- DCALJVULAGICIX-UHFFFAOYSA-N 1-propylpyrrolidin-2-one Chemical class CCCN1CCCC1=O DCALJVULAGICIX-UHFFFAOYSA-N 0.000 claims description 3
- LUVQSCCABURXJL-UHFFFAOYSA-N 1-tert-butylpyrrolidin-2-one Chemical compound CC(C)(C)N1CCCC1=O LUVQSCCABURXJL-UHFFFAOYSA-N 0.000 claims description 3
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 claims description 3
- XPEOTZMXIWGSAB-UHFFFAOYSA-N 2-butylhexanamide Chemical compound CCCCC(C(N)=O)CCCC XPEOTZMXIWGSAB-UHFFFAOYSA-N 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 claims description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 206010065042 Immune reconstitution inflammatory syndrome Diseases 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- SAQPWCPHSKYPCK-UHFFFAOYSA-N carbonic acid;propane-1,2,3-triol Chemical compound OC(O)=O.OCC(O)CO SAQPWCPHSKYPCK-UHFFFAOYSA-N 0.000 claims description 3
- 229940075419 choline hydroxide Drugs 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 3
- 230000007123 defense Effects 0.000 claims description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
- 239000012972 dimethylethanolamine Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 3
- WEFZXWJJPHGTTN-UHFFFAOYSA-N methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate Chemical compound COC(=O)C(C)CCC(=O)N(C)C WEFZXWJJPHGTTN-UHFFFAOYSA-N 0.000 claims description 3
- ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 claims description 3
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 3
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920006393 polyether sulfone Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 3
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 229920000491 Polyphenylsulfone Polymers 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims 1
- 238000007605 air drying Methods 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims 1
- 238000000643 oven drying Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 36
- 206010001497 Agitation Diseases 0.000 description 30
- 239000007787 solid Substances 0.000 description 25
- 239000007921 spray Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000002955 isolation Methods 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 229960004592 isopropanol Drugs 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010008 shearing Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- 238000000889 atomisation Methods 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
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- B01J2/02—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by dividing the liquid material into drops, e.g. by spraying, and solidifying the drops
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
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- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
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- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- 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
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- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Definitions
- Embodiments described herein generally relate to the field of chemical processing, and, more particularly, to a process for preparing polymer powders.
- PAI polyamide amic acid resin polymers
- the primary route to synthesizing polyamideimide polymers in a form that is convenient for the manufacture of coatings is by reacting diisocyanate, often 4,4'- methylene diphenyldiisocyanate (MDI) with trimellitic anhydride (TMA).
- MDI 4,4'- methylene diphenyldiisocyanate
- TMA trimellitic anhydride
- PAI polymers are typically manufactured in polar aprotic solvents such as N-methyl amide compounds including dimethylformamide, dimethylacetamide, N-methylpyrrolidone (NMP), N- ethylpyrrolidone.
- Figure 1 illustrates manufacturing elements utilized in a process for generation of a polymer powder according to an embodiment
- Figures 2A and 2B are schematic representations of a horizontal reactor in an embodiment
- Figure 3 is a flowchart to illustrate a process for generating polymer powder according to an embodiment
- Figure 4A is a table to summarize a first part of the information regarding the examples.
- Figure 4B is a table to summarize a second part of the information regarding the examples.
- Embodiments described herein are generally directed to generation of polymer powders.
- a process for preparing polymer powders with adjustable properties includes dissolving one or more polymers in a suitable solvent or combination of solvents, with the polymer solution being deployed and precipitated into a vigorously disturbed solution of one or more anti-solvents in a reaction vessel.
- the deployment of the polymer solution includes breaking the polymer solution into droplets using a deployment element to deploy the droplets into the disturbed anti-solvents.
- a process for preparing polymer powder takes place in a horizontal reactor equipped with, for example, a large rotating agitator and vortexing choppers that provide the driving force necessary for the preparation of a fine powder.
- Benefits of an embodiment include that the powder may be isolated, washed, and dried in a single reactor.
- the properties of the resulting powder may be tailored to fit a variety of applications by simultaneously optimizing the polymerization conditions, the resulting resin formulation, the choice of precipitation solvent, the deployment parameters, and additional horizontal reactor settings.
- a process of making a polymer powder includes deployment, such as spray precipitation, in a one-pot process using a horizontal reactor providing disturbance of a solution, such as high agitation of the solution, wherein the properties of the resulting powder are controlled using multiple aspects of the process such as the selection of spray nozzle or other deployment element, feed ratio, precipitation solvent choice and agitation rate.
- an embodiment of a process provides for generation of high performance polymers, such as PPS (Polyphenylene sulfide), PEEK (Polyether ether ketone), PI PI PI
- a process combining the benefits of forming droplets along with the control and one-pot nature of a horizontal reactor results in a controlled characterization and an easily dissolved polymer powder.
- a polymer solution that contains one or more polymers dissolved in a solvent or solvent/co-solvent mixture may form droplets using a variety of different deployment techniques, including, but not limited to, spraying, misting, jetting, atomizing, or impregnation of droplets the polymer mixture.
- a resulting isolated polymer may then be precipitated, washed, and dried, all in the same vessel.
- FIG. 1 illustrates manufacturing elements utilized in a process for generation of a polymer powder according to an embodiment.
- manufacturing elements 100 include a single reaction vessel 110 for generation of the polymer powder.
- the vessel 110 is a horizontal vessel that includes an agitator or other disruption element 115 for providing disruption (such as agitation) in mixing of solutions and chopper or other shearing element 120 for the shearing (such as chopping or slicing) of generated polymer material to generate a powder substance.
- the reaction vessel initially contains a precipitation solvent 125.
- manufacturing elements for generation of a polymer powder further include an application unit or mechanism 150, including one or more nozzles or other deployment element 155 for the deployment, such as spraying, misting, misting, jetting, atomizing, or impregnation of droplets, of a resin solution 160 into the precipitation solvent 125 to generate a mixture that results in precipitation of polymer material.
- the resin solution 160 is a solution in which a polymer resin has been dissolved in a dissolution solvent.
- the agitator 115 agitates the solution in the spraying and precipitation process, and the chopper 120 chops the resulting precipitate as needed in the formation of a polymer powder.
- FIGS 2A and 2B are schematic representations of a horizontal reactor in an embodiment.
- a process provides for an efficient production of a PAI (or other polymer) powder based on certain parameters, the parameters including some or all of: the number and/or configuration of deployment elements, such as spray nozzles, for deploying of a polymer solution 210; the number and/or configuration of shearing elements, such choppers, for the reaction vessel 220; the angle 230 and distance between the deployment and shearing elements, such nozzles and choppers 240; the selection of, for example, nozzle: chopper pairings in the reactor 250; and/or other factors.
- the process forgoes atomizing an anti-solvent and instead utilizes high agitation through the choppers, thereby taking advantage of a vortex of anti-solvent.
- a process combines the use of deployment elements, such as nozzles, to form droplets, including, but not limited to, spraying, misting, jetting, atomizing, impregnations, and more as examples, with the vigorous disruption of the solution such as, but not limited to, choppers, impellers, sonication, and other known methods that may break down resin, and the efficiency of a horizontal reactor may be used to isolate a variety of polymers in a controlled manner.
- deployment elements such as nozzles
- polymers/resins including, but not limited to, polyamides, polyamide imides, polyethers, polyether ether ketones, epoxide, polyether sulfones, polyesters, polyacrylates, polybenzimidazole, polyphenylene sulfides, polysulfones, and mixtures, derivatives, and/or copolymerizations thereof.
- An illustrative example of a suitable polymer is the polyamideimide (PAI) contained herein. PAI and solutions thereof have been used in various applications due to its excellent adhesion, temperature resistance, and high strength.
- aqueous-based coating compositions comprised of the polyamic acid salt form of the polymer have been used for coating and sizing fibers, metal surfaces, glass substrates, and other materials.
- aqueous-based PAI coating solutions are vital as binders for use in the cookware industry.
- polyamideimide also includes polyamic acid and salts of polyamic acid from which polyamideimide may be derived.
- the polymer solution includes a resin that is soluble in an organic or aqueous solution used to dissolve the material.
- the resulting resin solution may range from 10-90% solids. A higher percentage of solids is generally preferred for higher throughput - e.g., as limited by requirements of viscosity to allow for effective handling and spraying.
- the function of the reaction solvent (also referred to as a "dissolution" solvent) is to solubilize the resin.
- Additional co-solvents, thinning, thickening, or thixotropic agents may be added to further decrease or modify the viscosity for ease of transfer or spraying or to bring the resin solution closer to precipitation while still maintaining the solubility of the resin.
- Various embodiments utilize any of a variety of polymers/resins utilizing the appropriate dissolution solvent or solvent mixture by one who is skilled in the art including but not limited to alcohols, acetates, aldehydes, ethers, ketones, lactams, pyrrolidones, morpholines, morpholine derivatives, sulfoxides and mixtures thereof.
- solvents such as N-methyl-2-pyrrolidone (NMP), N-formyl morpholine (NFM) and N-acetyl morpholine (NAM), diethyl acetamide (DEAc), di-n-propyl acetamide, diacetylpiperazine, N,N- diisopropylacetamide (DIP Ac), di-n-butylacetamide (DIBAc), di-n-propylacetamide (DIP A), and N-propionyl morpholine (NPM), methyl actetate, n-propyl acetate, t-butyl acetate, iso-butyl acetate, ethyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, t-butyl lactate, cyclo
- Rhodiasolv® PolarClean from Rhodia Chemical Co.
- Rhodiasolv® Infinity from Rhodia Chemical Co.
- Rhodiasolv® IRIS from Rhodia Chemical Co.
- solvents such as methyl actetate, ethyl acetate, n-propyl acetate, iso-propyl acetate, n-butyl acetate, iso-butyl acetate, t-butyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, iso-propyl lactate, n-butyl lactate, iso-butyl lactate, t-butyl lactate, cyclopentanone, cyclohexanone, methylcyclohexane, methyl alcohol, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol, 3-methoxy ⁇ , ⁇ -dimethylpropanamide (also known as "Equamide" or "Equamide
- the preferred concentrations are 10-80% solids, with a more preferred range of 20-90% solids.
- mixing ratios of resin solution to anti- solvent to reduce viscosity may vary between 90:10 to 10:90. A more preferred range is 80:20 to 20:80 solvent: anti-solvent. However, the ratio needs to be such that the resin is stable and does not precipitate or phase separate upon setting.
- PAI polyamide- imide
- PAI resin polymers are well-known thermally stable polymers that are used for many high performance coating applications due to their excellent adhesion, temperature resistance, and high strength. PAI resins are used in solvent- based formulations for various coating uses.
- NMP N-methyl-pyrrolidone
- NMP was used to produce "environmentally friendly" coatings, replacing cresol as the predominant solvent at that time.
- NMP and n-ethyl-pyrrolidone (NEP) have been classified as reprotoxic chemicals, based on the EU REACH regulations.
- Fujifilm Hunt has successfully developed a proprietary alternative solvent solution to the REACH- classified CMR (carcinogenic, mutagenic, reprotoxic) chemicals currently available for PAI coating applications.
- MDA 4,4'-Methylene dianiline
- a vessel referred to herein as a pre-mixing vessel, holds a reaction solvent (also referred to as "dissolution" solvent) at a pressure that, for example, is in a range of 14.7 psi to 100 psi (in some embodiments, in a range of 14.7 psi to 80 psi) for transferring of the feed solution through the spray nozzles.
- a reaction solvent also referred to as "dissolution” solvent
- concentration a reaction solvent
- a pressure that, for example, is in a range of 14.7 psi to 100 psi (in some embodiments, in a range of 14.7 psi to 80 psi) for transferring of the feed solution through the spray nozzles.
- Agitation while heating the solution may reduce the viscosity of the feed solution for adequate spraying and transfer to the spray nozzles.
- the solution may be diluted and mixed until the viscosity is homogeneous throughout. Equivalent viscosity and concentration
- a jacket for temperature control may be utilized as this allows control of the temperature of the feed solution which will in turn affect the viscosity and flow rate.
- the temperature of the polymer solution may range between 0°C to 100°C more preferred 20 °C to 55 °C.
- the viscosity of the sprayed solution may be in the range of 5 centipoise (cP) to 50,000 cP (in some embodiments, in a range of 50 cP to 6000 cP) - e.g., depending on the type(s) and/or configuration of nozzles.
- the function of the precipitation solvent is to precipitate out the polymer into a powder form.
- a mean particle size of the powder is in a range of 10-800 microns (in some embodiments, in a range of 10 microns to 500 microns).
- the precipitation solvent may be miscible with the reaction solvent as phase separation of the two solvents may complicate the precipitation.
- both the resin dissolution solvent and the precipitation solvent have low boiling points - e.g., to facilitate easy removal during a drying step.
- the boiling point may be in a range of 0 °C to 240 °C (in some embodiments, in a range of 50 °C to 240 °C).
- the respective boiling points of the reaction solvent and precipitation solvent differ from one another - e.g., by an amount in a range of 10 °C to 50 °C.
- a reaction solvent having a higher boiling point may tend to need to be washed out during processing by the anti-solvent - e.g., as opposed to being removed during a drying step. Having a significant difference in the boiling points aids in solvent recovery.
- the polarity of the precipitation solvent may depend on the resin system that is to be precipitated.
- polar aprotic solvents such as MEK may be more appropriate.
- non-polar anti-solvents such as hexanes.
- the polymerization (reaction) solvent and anti-solvent (precipitation solvent) may both be from the same class of solvents (such as alcohols).
- a polymer may be soluble in octanol but precipitate readily in methanol, both of which are alcohols.
- Spray precipitation processing according to some embodiments may be implemented with a variety of polymer/solvent:anti-solvent combinations or mixtures thereof.
- Some embodiments use any of a variety of anti-solvents (precipitation solvents) or anti-solvent mixtures including but not limited to alcohols, acetates, aldehydes, ethers, ketones, lactams, pyrrolidones, morpholines, morpholine derivatives, sulfoxides, and mixtures thereof.
- anti-solvents precipitation solvents
- anti-solvent mixtures including but not limited to alcohols, acetates, aldehydes, ethers, ketones, lactams, pyrrolidones, morpholines, morpholine derivatives, sulfoxides, and mixtures thereof.
- solvents such as N-methyl-2-pyrrolidone (NMP), N-formyl morpholine (NFM) and N-acetyl morpholine (NAM), diethyl acetamide (DEAc), di-n-propyl acetamide, diacetylpiperazine, N,N-diisopropylacetamide (DIPAc), di-n-butylacetamide (DIB Ac), di-n-propylacetamide (DIP A), and N-propionyl morpholine (NPM), methyl acetate, n- propyl acetate, t-butyl acetate, iso-butyl acetate, ethyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, t-butyl lactate, cycl
- Rhodiasolv® PolarClean from Rhodia Chemical Co.
- Rhodiasolv® Infinity from Rhodia Chemical Co.
- Rhodiasolv® IRIS from Rhodia Chemical Co.
- dimethylsuccinate, N-methylcaprolactame and N-cyclohexylpyrrolidone may all be used as precipitation solvents or solvent mixture depending on the nature of the polymer material. More preferable solvents such as methyl acetate, ethyl acetate, n-propyl acetate, iso-propyl acetate, n- butyl acetate, iso-butyl acetate, t-butyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, iso-butyl lactate, t-butyl lactate, cyclopentanone, cyclohexanone, methylcyclohexane, methyl alcohol, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol, n-acetyl
- the reaction vessel (which may also be referred to as the reactor or precipitation vessel) that holds the precipitation solvent (also referred to as an "anti- solvent”) may be able to hold a volume of 50 to 5000 gallons and/or withstand pressures in a range of 14.7 to 100 psi.
- the pressure of the precipitation reactor is at ambient pressure (14.7 psi), wherein a nitrogen sweep goes through a condenser to trap vapors which may be easily evaporated while spraying.
- the temperature of the precipitation vessel may be at ambient temperature (e.g., 71 °C), however, it may be in a range of 0 °C to 100 °C (for example) - e.g., based on conditions favoring rapid separation between the precipitated powder and the solvent mixture.
- the temperature of the chamber of the reaction vessel and precipitation solution may play a role in how effectively the reaction solvent is washed out of the resin powder and therefore affect the drying process.
- the reaction vessel may be a horizontal reactor where "horizontal” refers to the orientation of cylindrical portion of the reactor along with the agitator shaft.
- the spray precipitation and isolation techniques described herein are not limited to horizontal reactors and may be applied to additional reactor configurations such as continuous stirred tank reactors (CSTR), plug flow reactors, laminar-flow reactors and semi-batch reactors depending on the conditions implemented.
- a CSTR may be used as the reaction vessel in conjunction with spray nozzles and choppers to create finely precipitated material which is washed by a stream of incoming fresh solvent and then pumped out through a high shear mixer to a centrifuge.
- a process includes disruption such as agitation to facilitate precipitation of resin.
- the vigorous mixing of the solution while the precipitation is occurring may be obtained by rotating agitators including but not limited to anchor, turbine or, corkscrew type which may operate in the range of 10-10,000 rpm. A more preferred is 50-500 rpm for commercial agitators. Additional smaller mixing components such as choppers may be utilized to improve the precipitation process which may operate in the range of 500-10,000 rpm, more preferred is 1000-5000 rpm.
- Other methods such as the use of baffles, recirculation lines, and in-line high shear mixers or a combination thereof may also be used for improved agitation and finer powder.
- a process or apparatus includes spraying of the polymer solution into the precipitation solvent may yield a powder material with improved particle size compared to the powder produced in a process where the resin solution is merely transferred through a line. This is due to the unique ability of the nozzle to "atomize" the polymer solution into tiny droplets allowing for a more effective precipitation.
- nozzle types include high efficiency spray nozzles with plain or shaped orifice, surface impingement nozzle, air atomizing nozzles (both internal and external mix), as well as compound nozzles and internal and external two fluid mix nozzles.
- the spray nozzle or nozzles may provide particles with a mean size in a range of 1 micron to 1000 microns (e.g., in a range of 10 microns to 500 microns).
- the control of the particle size of the final powder may be based on any of the various parameters described herein.
- a specific nozzle type selected may be one that allows the resin to atomize or "spray" without clogging or bearding. Note that a manifold containing one of more nozzle types with different atomization technologies may be
- a number of deployment elements determines at least in part the feed rate of the polymer solution, with more nozzles and a larger diameter or cap opening allowing for a faster addition of the resin.
- the feed rate may vary from, for example, 1 pound per hour (pph) to 50,000 pph per nozzle (e.g., in a range of 50 pph to 500 pph per nozzle).
- other parameters that affect the feed rate include one or more of the viscosity, concentration, and temperature of the resin solution as well as the capacity or flow rate of the air or nitrogen source (in cubic feet/ min or hour).
- Air atomizing nozzles use a combination of air pressure and liquid pressure to atomize the resin material.
- the air pressure supplied by either air or nitrogen, may be in a range of 2 psi to 1000 psi (e.g., in a range of 8 psi to 80 psi).
- the pressure placed on the liquid, which is usually nitrogen may be in a range of 1 psi to 100 psi (in some embodiments, in a range of 5 psi to 70 psi).
- nozzles may be positioned that the spray angles do not overlap causing aggregation of the droplets before hitting the antisolvent and precipitation. This may be accomplished by proper placement or using a combination of different nozzle/cap types.
- Solvent may be primarily sprayed in a direction towards a majority volume of anti-solvent (e.g., toward a vortex of antisolvent caused by a chopper or other source of disruption). As illustrated in Figure 2B, angle 230 and distance 240 from the chopper may result in spraying to hit the vortex created by the chopper or the surface of the agitating precipitation solvent and the distance being such that the round spray pattern produced by the nozzle is still maintained.
- the spray angles may not overlap, and may be oriented in such a way as to avoid interference from other objects such as reactor walls, baffles, and agitator blades.
- a feed rate of the sprayed polymer solution is based on any of a variety of parameters including, but not limited to, a number of nozzles and a pressure (of air or nitrogen) placed on the resin solution or in conjunction with the nozzle for atomization.
- Other parameters which may affect the feed rate include the viscosity, concentration, and temperature of the resin solution.
- washing (wherein the term “washing” refers to the removal of the reaction solvent by the precipitation solvent or other solvent in order to increase the final percentage of solids of the isolated powder) may be performed to remove the reaction solvent from the powder prior to drying. If not enough reaction solvent is removed from the powder prior to drying, the material may cake up or turn into a sludge during the drying step.
- the washing may be performed using a variety of methods or combination thereof, some of which have been demonstrated in the embodiments herein.
- the agitation may be stopped and the powder allowed to settle to the bottom of the reactor and the top liquid phase may be removed by decantation or a J-tube.
- the powder material may then be washed by adding fresh solvent and restarting the agitation and repeating the washing process as needed until the wetcake may be transferred directly to the dryer.
- the powder may also be isolated and washed using a Buchner funnel, a nutsche filter, or a centrifuge with the washings happening before or on the filtering medium.
- the polymer powder may be collected externally on an FSI, sparkle or bag-type filter and re-loaded into the reactor for additional washes.
- a metal mesh screen may also be used to contain the powder within a reactor for additional washes. This process may potentially be repeated with numerous washes of various solvents until a powder with the desired properties is obtained.
- a maximum percentage solids limit that may be obtained may range from 80 to 100 % solids even after excessive washing. This may be due to a solvent that is strongly associated and trapped within the polymer particle structure and unable to diffuse out.
- a maximum obtainable percentage of solids is directly correlated to the initial particle size produced upon precipitation, the polymer molecular weight, the choice of reaction solvent and anti-solvent, the temperature, the method and rpm of agitation, the time of contact between the resin solution and precipitation solvent or precipitated powder and wash solvent, and numerous other parameters.
- the wetcake from a process or apparatus may be loaded into a drying unit and dried until a powder with the desired properties is obtained.
- the powder polymer material may be air dried depending on the boiling point of the solvent. It may also be dried in an oven or vacuum oven with temperatures ranging from 20 °C to 100 °C though more preferred is 25 °C to 55 °C.
- Other methods for drying the polymer powder are also possible by those who are skilled in the art using equipment similar to that which is used in thin film evaporators and heated belt systems. In order to dry the material to the final desired percentage of solids, any method which provides a gradient in temperature or pressure capable of removing the solvent is appropriate.
- a combination of vacuum and drying methods may be utilized to drive the material to the highest percentage solids level possible, with the final residual solvent concentrations of the powder being well below the level required for reporting or toxicological concerns.
- the precipitation, washing and drying operations are done in a single unit for efficacy in a horizontal reactor as described, but can also be done in a similar equivalent unit such as a conical screw mixing unit, double planetary mixing unit, a double ribbon, paddle, and continuous blender/dryer unit, a vee double cone blender/dryer unit, or a combination thereof.
- resin powder may be passed through a sieve or mesh screen to eliminate oversize or aggregated chunks of powder to help isolate the desired particle size distribution once it has been produced.
- Screen pore sizes typically range from 10 to 1000 ⁇ , wherein a more preferred range is 300 to 600 ⁇ .
- Figure 3 is a flowchart to illustrate a process for generating polymer powder according to an embodiment.
- a process for generating a polymer powder includes:
- [0046] 304 Generating a resin solution including dissolving a polymer resin in a first reaction solvent.
- [0047] 308 Disturbing a second precipitation solvent in a chamber of reaction vessel, such as, for example, by agitating the precipitation solvent using an agitator.
- the precipitation solvent is chosen based on the characteristics of the reaction solvent and the polymer resin.
- [0048] 312 Deploying the resin solution into the precipitation solvent, such as, for example, by spraying, spraying, jetting, misting, atomizing, or impregnating the resin solution into the precipitation solvent contained in the chamber of the reaction vessel, wherein deploying the resin solution may include utilizing a spray nozzle or other deployment element to generate droplets of the resin solution.
- the deployment of the resin solution into the precipitation solvent results in precipitation of the polymer from the mixture of the resin solution and precipitation solvent, or, stated in another way, generation of a precipitate.
- the disturbing of the precipitation solvent continues during the application of the resin solution, and further the disturbing of the resulting mixture or resin solution and precipitation solvent continues for a period of time after the deployment of the resin solution.
- the process continues with generating a polymer powder from the mixture of the resin solution and precipitation solvent, including: [0051] 320: Isolating (or separating) the precipitate from the mixture of the resin solution and precipitation solvent, wherein isolating of the precipitate may include, but it not limited to, decantation of the solvent from the mixture, filtration of the mixture, or a combination thereof.
- the process further includes washing of the isolated precipitate, 328.
- drying may include, but is not limited to, placing the precipitate into a dryer or oven at a certain temperature for a certain period of time.
- the isolation of the precipitate and the drying of the isolated precipitate occur at least in part in the same reaction vessel.
- Figures 4A and 4B illustrate features of examples of implementations according to a corresponding embodiment.
- Figure 4A provides the following with regard to each example:
- Figure 4B further provides the following with regard to each example:
- a process or apparatus may include one or more of the following examples. However, embodiments are not limited to these examples or the specific manner in which the examples are implemented.
- a room temperature 26% solids PAI solution composed of 70:30 NFM:MEK was slowly poured into a vessel containing 100% MEK at ambient temperature with agitation supplied by a laboratory mixer set at 200 RPM equipped with a turbine agitator blade.
- the resin solution was fed over 1 hour with a 3: 1 ratio of precipitation MEK : resin solution by mass.
- the solution was allowed to mix for 10 minutes after the addition, and the resulting material was allowed to settle.
- the MEK top layer was decanted and fresh MEK (in a ratio of 1.2: 1 wash MEK : resin by mass) was added.
- the agitation was resumed for 10 minutes, then the material was allowed to settle for 1 hour.
- the precipitated powder material was washed again with the same ratio of fresh MEK, allowed to settle, and the top layer of MEK decanted.
- the resin was isolated using vacuum filtration and dried in a vacuum oven at 50°C for 12 hours.
- the PAI resin material produced using a laboratory agitator had a prill-like structure which resembled a noodle and was not a fine powder.
- the material may be further ground up by re-suspending in MEK and shearing with increased agitation speed (1000 rpm) for additional time, however, visually the material still had a grainy appearance closer to sand than fine powder. Furthermore, the material did not show an increase in percentage of solids when additional washes were performed.
- the particle size is expected to be directly related with the ability to wash and dry the material. Larger particles will allow for slower diffusion of the NFM into the MEK during washing. This typically resulted in a lower final solid content. Furthermore larger particle size results in slower drying. This typically results in longer drying times and also lower final solid content. This first example demonstrates the importance of agitation on the final product appearance and particle size.
- Example II The procedure of Example I was followed except the agitator used was a Silverson high shear mixer set at 4000 rpm instead of a laboratory mixer at 200 rpm. Since a laboratory benchtop horizontal reactor with choppers and a horizontal agitator was not available, the high shear mixer was used to as a replacement to emulate vigorous agitation. The resulting material after washing, isolation and vacuum drying was a fine powder. Though it is important to note that resin solution was only transferred in as a thin stream like Example I and not sprayed, like the examples further below. This example demonstrates the ability to produce a CMR-free PAI powder material due to the nature of the CMR-free reagents utilized. The novel powder had excellent solubility in organic solvents and was also formulated for use in water-based solutions. Example III.
- the noodle-like material was washed twice using a 1.2: 1 wash MEK:resin by mass, with the MEK phase being removed using a J-tube.
- the resin was isolated using a nutsche filter and dried in a dryer for 12 hours at 50°C.
- the resulting noodle-like material was reduced to powder using grinders, leading to additional cycle time.
- re-washing the ground powder did not result in a significant increase in solids, demonstrating the advantages of using nozzles to obtain a fine powder during the initial addition of the resin solution to the anti- solvent.
- Example IV Example IV.
- Examples IV- VIII The purpose of Examples IV- VIII was to attempt to obtain a fine powder through atomization by varying the viscosity of the resin solution, the fluid cap, the air cap, and the feed rate.
- a 1.5 L Parr reactor was filled with the same PAI solution composed of 70:30 NFM:MEK diluted with additional MEK to 1280 cP at 71°F.
- the resin solution was transferred to a pan of MEK through a 1/4J nozzle paired with a 100150 fluid cap and 1891125-SS air cap with a liquid pressure of 80 psi and an air pressure of 30 psi. This resulted in a feed rate of 3.6 g/min of the resin solution which was efficiently atomized from the nozzle resulting in the formation of a fine powder.
- the powder was isolated using vacuum filtration and dried in a 50°C oven for 12 hours.
- the final powder material has a mean particle size of 167 ⁇ and a d95 of 323 ⁇ .
- Example IV The procedure of Example IV was substantially repeated except using the undiluted 26% solids PAI solution composed of 70:30 NFM:MEK with a viscosity of 5539 cP and a liquid pressure of 80 psi and an air pressure of 75 psi. This resulted in a feed rate of 9.5 g/min of the resin solution which was efficiently atomized from the nozzle resulting in the formation of a fine powder.
- the final powder material has a mean particle size of 199 ⁇ and a d95 of 329 ⁇ .
- Example VI Example VI.
- Example V The procedure of Example V was substantially repeated except using a 180- SS air cap. This resulted in a feed rate of 27.5 g/min of the resin solution which was efficiently atomized from the nozzle resulting in the formation of a fine powder.
- the final powder material has a mean particle size of 146 ⁇ and a d95 of 248 ⁇ .
- Example VI The procedure of Example VI was substantially repeated except using a 60100 fluid cap and 120-SS air cap. This resulted in a feed rate of 10.0 g/min of the resin solution which was efficiently atomized from the nozzle resulting in the formation of a fine powder.
- the final powder material has a mean particle size of 152 ⁇ and a d95 of 301 ⁇ .
- Example VII The procedure of Example VII was substantially repeated except using a 1401110-SS air cap. This resulted in a feed rate of 7.0 g/min of the resin solution which was efficiently atomized from the nozzle resulting in the formation of a fine powder. However flow rates as high as 62.1 g/min may be obtained by opening the ball valve and allowing more pressurized material to flow from the parr reactor to the nozzle.
- the final powder material has a mean particle size of 197 ⁇ and a d95 of 328 ⁇ .
- the spray angle may be altered by changing the orifice size of the air cap. Larger diameter outlets resulted in wider spray angles. Depending upon final reactor dimensions, this information may be used to appropriately space nozzles. A wider spray angle may result in more effective washing, as the same flow rate may be spread over a greater area, leading to better diffusion of the reaction solvent out of the polymer particles. If reactor dimensions, such as the use of a vertical reactor, dictate tight spacing of nozzles though, a narrower spray angle may be employed in order to prevent collision of separate spray streams before precipitation.
- Example IX the 26% solids PAI resin solution was transferred to a horizontal reactor equipped with a chopper agitating at 100% and a horizontal agitator at a speed of 150 RPM.
- the resin was transferred through a 1/4 LNN 316SS Atomizing nozzle at a rate of 500 g/min into MEK with a ratio of MEK:resin of 2.2: 1 by mass over 1 hour with the resin at ambient temperature and the reactor temperature set to 50 °F to keep the batch temperature below 120°F due to heat generated from the choppers.
- the resin was transferred by pressurizing a feed tank to 80 psi, however at this pressure, the resin came out of the nozzle as a thin stream and not a spray. Once the transfer was complete the precipitation was allowed to agitate for an additional hour.
- the ratio of precipitation MEK:resin used in this example is smaller than previous examples where either a higher ratio or excess precipitation MEK was used. This may suggest that the increased level of agitation afforded by the chopper may allow for a lower ratio of precipitation MEK:resin which may results in significant cost reduction for the process.
- the powder was isolated using an FSI bag filter and transferred back into the reactor for additional washings with fresh MEK.
- the powder was washed with a ratio fresh MEK:initial resin of 1.1 :1 by mass for 20 minutes with the agitators at 100% and the agitator at 150 RPM.
- the powder was isolated and washed an additional time as described above, then the powder was collected and put back into the reactor for drying.
- the powder was dried for 4 hours at 120°F and the powder was checked for dryness by running the percentage solids by moisture balance (MB) to constant weight (MB) oven solids (250°C, 1 hour).
- the material was passed through a 425 ⁇ sieve and packed out to give a fine polymer powder.
- the final powder material contained some oversize particles that had to be screened prior to packout. This is most likely due to the fact that the resin was not transferred into the reactor as a spray but as a stream which hit the chopper. Though the final material was in powder form, the particle size distribution may be further improved by optimizing the atomization of the transferred material using the nozzles. This example accurately demonstrates the tunable nature of this novel process where numerous parameters may potentially be altered to obtain the desired results on the powder polymer material.
- the 26% solids PAI resin solution was transferred to a 4000 gal horizontal reactor equipped with three choppers agitating at 100% and a horizontal agitator at a speed of 95 RPM.
- the resin was transferred through a 1/4 LNN 316SS Atomizing nozzle at a rate of 2668 g/min into MEK with a ratio of MEK:resin of 2.2: 1 by mass over 1 hour with the resin at ambient temperature and the reactor temperature set to 50°F to keep the batch temperature below 120°F due to heat generated from the choppers.
- the resin was transferred by pressurizing the feed tank to 30 psi. Once the transfer was complete the precipitation was allowed to agitate for an additional hour.
- the powder was isolated using an FSI bag filter and transferred back into the reactor for additional washings with fresh MEK.
- the powder was washed with a ratio fresh MEK:initial resin of 1.1 : 1 by mass with the agitators at 100% and the agitator at 95 RPM.
- the powder was isolated and washed an additional time as described above and dried to give a fine powder with a mean particle size of 141 ⁇ and a d95 of 210 ⁇ .
- Examples IX and X allow both the spraying and agitation as well as numerous other parameters to be fine-tuned which clearly demonstrates the potential and captures the novelty of this embodiment.
- Example XI For Example XI, a room temperature 28% solids water-based PAI solution composed of NFM, TEA, and water was slowly poured into a vessel containing 50:50
- MEK acetone at ambient temperature with agitation supplied by a Silverson High shear mixer set at 4000 RPM .
- the 3615-APH water-based polyamide-imide resin solution is slowly added over 1 hour resulting in the precipitation of polymer powder.
- the agitator is stopped and the powder is allowed to settle.
- the solvent top phase is decanted from the beaker. Additional fresh solvent is added to the beaker (acetone) and the powder is washed for 10 minutes at 4000 rpm, followed by decantation.
- the wash/decant step is repeated.
- the powder is isolated by filtration and washed with additional acetone and dried at 50°C overnight for 12 hours to give the off-white powder with a mean particle size of 54 ⁇ and a d95 of 120 ⁇ .
- Example XI demonstrates the versatility of this process as a completely different resin solution (notably a polyamide imide that has been converted to the corresponding polyamide amic acid salt (also referred to as a polyamic acid or salt of any of the aforementioned terms) is used along with a different precipitation co-solvent (acetone).
- aqueous-based polyamide- amic acid formulation composed of PAI, water, solvent, and any tertiary amine such as trimethylamine, dimethylethanolamine, dimethylethylamine, or a combination thereof or an alternate base could be taken through the process described in this embodiment and converted to the corresponding powder.
- This example also demonstrates how the methodology contained in this embodiment could be used for numerous types of polymers such as PEEK (Polyether ether ketone), PI (Polyimide), PBI (Polybenzimidazole),
- this particular example utilizes CMR-free reagents and is an example of how a water-soluble CMR-free PAI powder may be produced. This particular powder process may also be scaled up to the inventive manufacturing examples above.
- Examples XII-XVI The purpose of Examples XII-XVI is to once again demonstrate the versatility of the process and show how different methods of agitation (static, lab reactor, or Silverson high shear mixer) and even isolation methods (laboratory vacuum filtration vs. centrifuge) can be implemented in this process and alter the particle size and other potential properties of the final dried powder. Furthermore, unlike examples IV- VIII, the ratios of MEK:resin solution were not in excess and held constant. This allowed the effect of agitator type to be explored exclusively.
- Example XII the resin 26% solids PAI polymer solution was precipitated into MEK with no agitation to explore the importance of agitation on the powder precipitation when using these limited solvent ratios.
- the lack of MEK precipitation solvent resulted in the aggregation of the powder material into a sludge.
- the small amount of powder which remained free was then more effectively washed by the MEK, resulting in a powder with a mean particle size of 229 ⁇ . This shows the ability of the agitation to affect both the precipitation and the washing steps.
- Example XIII the conditions used were identical to Example XII except a laboratory agitator set to 200 rpm was used to stir the MEK.
- the resin solution precipitated after spraying into the MEK, however upon drying, the powder aggregated into a sludge. This indicated inefficient washing most likely induced by the low agitation rate.
- Example XIV the same conditions as example XII were used except a Silverson high shear mixture set at 4000 rpm was used to stir the MEK during the precipitation and washing steps. This resulted in the formation of a fine powder with a mean particle size of 314 ⁇ with only some aggregation.
- Example XV the same conditions as example XII were used except a Silverson high shear mixture set at 4000 rpm was used to stir the MEK during the precipitation.
- the washing and isolation steps were performed on a centrifuge.
- Numerous manufacturing methods exist to isolate the powder such as a nutsche filter, a centrifuge, a FSI bag filter, a sparkle filter, or a metal wire mesh screen.
- This example implemented a centrifuge with a 30 ⁇ centrifuge cloth.
- the final powder after washing had a mean particle size of 135 ⁇ .
- One embodiment of the present invention explores the effect of centrifuge speed on the final percentage solids of the powder.
- the preferred rpm of the centrifuge for powder washing may be in the range of 100-10,000 rpm with a more preferred range of 1000-6000 rpm.
- Example XV the same conditions as example XII were used except a laboratory agitator at 200 rpm was used to stir the MEK during the precipitation. The washing and isolation steps were performed on a centrifuge. Unlike example XIII, the final PAI powder after drying was fine and had a mean particle size of 314 ⁇ . This suggests that the centrifuge in conjunction with the described embodiment not only has benefits for isolation of the powder but perhaps offers the opportunity for improved washes relative to methods which resemble ordinary vacuum filtration. This example also supports that the proper nozzle chosen in combination with a sufficient isolation/wash method, such as a centrifuge, might be able to compensate for lack of excessive agitation (such as choppers).
- a centrifuge might be able to compensate for lack of excessive agitation (such as choppers).
- this example demonstrates that the methodology described in this embodiment may be expandable to other reactor and dryer systems such as a centrifuge, a vertical cylindrical kettle-type reactor, a continuous stirred tank reactors (CSTR), a plug flow reactor, a laminar-flow reactor, a semi-batch reactor, a conical screw mixing unit, a double planetary mixing unit, a double ribbon, paddle, and continuous blender/dryer unit, a vee double cone blender/dryer unit, a mixture thereof, or additional types of reactor configurations by those who are skilled in the art.
- CSTR continuous stirred tank reactors
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PCT/US2017/035998 WO2017214056A1 (en) | 2016-06-06 | 2017-06-05 | Preparation of polyamide-imide resins using n-formyl morpholine:3-methoxy n,n-dimethylpropanamide |
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US (4) | US10301506B2 (en) |
EP (3) | EP3464423A4 (en) |
JP (3) | JP2019518836A (en) |
KR (3) | KR20190016503A (en) |
CN (3) | CN109415508A (en) |
BR (3) | BR112018074885A2 (en) |
CA (3) | CA3023729A1 (en) |
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CN110300779B (en) * | 2017-02-20 | 2022-03-29 | 昭和电工材料株式会社 | Polyamide-imide resin composition and fluorine-containing coating material |
WO2019026838A1 (en) * | 2017-08-01 | 2019-02-07 | 日立化成株式会社 | Polyamide-imide resin composition and fluorine-containing coating material |
EP3807292A4 (en) | 2018-06-14 | 2022-03-16 | CEM Corporation | Solvent system for solid phase peptide synthesis |
US20210395458A1 (en) * | 2018-09-28 | 2021-12-23 | Kaneka Americas Holding, Inc. | Polyamic acid resin in reach-approved solvent system for wire coating applications |
US20210189066A1 (en) * | 2019-12-18 | 2021-06-24 | Fuji Xerox Co., Ltd. | Polyimide precursor solution and method for producing polyimide film |
CN116194513A (en) * | 2020-09-22 | 2023-05-30 | 艾伦塔斯欧洲有限公司 | Wire enamel composition comprising polyamideimide |
CN112679631B (en) * | 2020-12-22 | 2022-07-08 | 宁波南大光电材料有限公司 | Method for removing small molecular substances in synthetic resin |
WO2022200416A1 (en) | 2021-03-25 | 2022-09-29 | Elantas Europe Srl. | Environmentally friendly waterbased engineering polymer compositions |
CN114085380B (en) * | 2021-12-06 | 2023-09-19 | 万华化学集团股份有限公司 | Thermoplastic polyimide resin and preparation method thereof |
CN115851773A (en) * | 2022-11-14 | 2023-03-28 | 无锡新晨宇生物工程有限公司 | Creation and application of aromatic amide biosensor |
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2016
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