CN109438658B - A kind of polyaryletherketone modified waterborne polyurethane resin - Google Patents
A kind of polyaryletherketone modified waterborne polyurethane resin Download PDFInfo
- Publication number
- CN109438658B CN109438658B CN201811193476.6A CN201811193476A CN109438658B CN 109438658 B CN109438658 B CN 109438658B CN 201811193476 A CN201811193476 A CN 201811193476A CN 109438658 B CN109438658 B CN 109438658B
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- CN
- China
- Prior art keywords
- polyaryletherketone
- polyurethane resin
- preparation
- water
- modified
- 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.)
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- 229920006260 polyaryletherketone Polymers 0.000 title claims abstract description 71
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 150000002989 phenols Chemical class 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000004970 Chain extender Substances 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 20
- 150000001412 amines Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 12
- 238000004945 emulsification Methods 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000005070 sampling Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- -1 difluoro aromatic hydrocarbon Chemical class 0.000 claims description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229960003742 phenol Drugs 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 6
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 6
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 125000003158 alcohol group Chemical group 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003607 modifier Substances 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 claims description 4
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 4
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 4
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 claims description 3
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims description 3
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- PISLKPDKKIDMQT-UHFFFAOYSA-N [3-(4-fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1 PISLKPDKKIDMQT-UHFFFAOYSA-N 0.000 claims description 3
- LLJNTLUXOZPFQB-UHFFFAOYSA-N [4-(4-fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=CC(F)=CC=2)C=C1 LLJNTLUXOZPFQB-UHFFFAOYSA-N 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 3
- 239000012972 dimethylethanolamine Substances 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 claims description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 229960004275 glycolic acid Drugs 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 abstract description 8
- 239000004814 polyurethane Substances 0.000 abstract description 8
- 239000000839 emulsion Substances 0.000 abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003973 paint Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CUOUCRFCPUTPGY-UHFFFAOYSA-N 4-(4-hydroxy-3-phenylphenyl)-2H-phthalazin-1-one Chemical compound OC1=C(C=C(C=C1)C1=NNC(=O)C2=CC=CC=C12)C1=CC=CC=C1 CUOUCRFCPUTPGY-UHFFFAOYSA-N 0.000 description 1
- LYLHOKOTRWUGIF-UHFFFAOYSA-N 4-(4-hydroxyphenyl)-2H-phthalazin-1-one Chemical compound C1=CC(O)=CC=C1C1=NNC(=O)C2=CC=CC=C12 LYLHOKOTRWUGIF-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RHKLYAUSQLLELZ-UHFFFAOYSA-N CC1=C(C=CC(=C1)O)C1=CC=NC2=NC=CC=C12 Chemical compound CC1=C(C=CC(=C1)O)C1=CC=NC2=NC=CC=C12 RHKLYAUSQLLELZ-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-RNFDNDRNSA-N Potassium-43 Chemical group [43K] ZLMJMSJWJFRBEC-RNFDNDRNSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical group [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-O tributylphosphanium Chemical compound CCCC[PH+](CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-O 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009736 wetting 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5054—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/506—Polyethers having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4031—(I) or (II) containing nitrogen
- C08G65/4037—(I) or (II) containing nitrogen in ring structure, e.g. pyridine group
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- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
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Abstract
本发明涉及一种聚芳醚酮改性水性聚氨酯树脂及其制备方法，首先通过控制二元取代酚、二氟代芳烃的比例，采用逐步聚合制备线性低分子量的羟基封端的聚芳醚酮，然后用该羟基封端的聚芳醚酮化学改性聚氨酯乳液。本发明聚氨酯分子中还有较多聚芳醚酮单元，具有化学稳定性好、力学性能优、耐溶剂性好的特点，应用前景广泛。The invention relates to a polyaryletherketone-modified water-based polyurethane resin and a preparation method thereof. Firstly, by controlling the ratio of divalent substituted phenol and difluoroaromatic hydrocarbon, a linear low molecular weight hydroxyl-terminated polyaryletherketone is prepared by stepwise polymerization, The polyurethane emulsion is then chemically modified with the hydroxyl terminated polyaryletherketone. There are more polyaryletherketone units in the polyurethane molecule of the present invention, which has the characteristics of good chemical stability, excellent mechanical properties and good solvent resistance, and has wide application prospects.
Description
Technical Field
The invention relates to a water-based resin, in particular to a polyaryletherketone modified water-based polyurethane resin, and belongs to the technical field of environmental protection.
Background
The water-based paint is the main direction of the development of the paint in the world. The water-based paint takes water as a solvent or a dispersion medium, has the characteristics of common paint, no toxicity, no smell, difficult combustion and the like, meets the environmental protection requirement and is more and more popular with users. The VOC content, benzene series and heavy metal content in the water-based paint are greatly lower than those of oil-based paint, the brushing area is generally more than twice of that of the oil-based paint, the water-based paint is convenient to use, can be diluted by tap water, and construction tools and equipment are extremely easy to clean, so that the water-based paint belongs to a green and environment-friendly product.
At present, the water-based wood coating and the water-based industrial wood coating are applied more and more. However, at present, the hardness and fullness of the water-based wood coating products sold in the market are low and the wear resistance is poor after the coating is finished; at present, the domestic woodware varnish generally adopts solvent type polyurethane coating, has good fullness of coating appearance, high hardness, greatly improves product grade, and has extremely strong decoration, and the performance of the water-based woodware coating is lower than that of solvent type coating.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention aims to provide a polyaryletherketone modified waterborne polyurethane resin.
The invention adopts the following technical scheme that polyaryletherketone modified waterborne polyurethane resin is prepared by firstly adopting step-by-step polymerization to prepare linear low-molecular-weight hydroxyl-terminated polyaryletherketone and then using the polyaryletherketone to chemically modify polyurethane emulsion, wherein the preparation of the polyaryletherketone modified waterborne polyurethane resin comprises the following steps:
a) heating binary substituted phenol, difluoro aromatic hydrocarbon, weak base and inert solvent for reaction, and removing the inert solvent by reduced pressure distillation to prepare linear polyaryletherketone;
b) heating hexamethylene diisocyanate, linear polyaryletherketone, a hydrophilic modifier, a catalyst and a diluent for reaction, and adding an alcohol chain extender for chain extension reaction to prepare a polyaryletherketone modified polyurethane prepolymer;
c) adding tertiary amine and deionized water into the polyaryletherketone modified polyurethane prepolymer for emulsification reaction, then dropwise adding organic amine chain extender dropwise, and distilling the solvent under reduced pressure to obtain the polyaryletherketone modified waterborne polyurethane resin.
Furthermore, the preparation method of the polyaryletherketone modified waterborne polyurethane resin comprises the following steps:
a) preparation of linear polyaryletherketone: under the condition of introducing nitrogen, adding 18-25 parts of binary substituted phenol, 9-13 parts of difluoroaromatic hydrocarbon, 6-8 parts of weak base and 40-50 parts of inert solvent into a reactor provided with a water distribution device, a heating device and a stirring device, heating to 130-150 ℃ under stirring, continuously removing water generated in the reaction through the water distribution device, carrying out heat preservation reaction at the temperature of 130-150 ℃ for 3-4h, then heating to 180 ℃ at the heating speed of 5 ℃/h, carrying out heat preservation polymerization at the temperature of 180 ℃ for 5-7h, and finally removing the inert solvent through reduced pressure distillation to obtain the linear polyaryletherketone.
b) Polyaryletherketone modified polyurethane prepolymer: under the conditions of nitrogen protection and stirring, sequentially adding 10-14 parts of hexamethylene diisocyanate, 27-45 parts of a) medium linear polyaryletherketone, 2-4 parts of hydrophilic modifier, 0.01-0.1 part of catalyst and 12-18 parts of diluent into a reactor, heating to 80-100 ℃, reacting for 2-5h, sampling and detecting, and cooling to 55-70 ℃ when the measured-NCO value reaches 13-16 ℃; adding 3-6 parts of alcohol chain extender and 0.01-0.1 part of catalyst to carry out chain extension reaction under the stirring of the rotation speed of 600-800rpm, starting sampling after 2-3 hours until the measured-NCO value reaches 4-8%, cooling to room temperature and stopping reaction to obtain the modified polyurethane prepolymer;
c) emulsification: dissolving 1-2 parts of organic amine chain extender into 10-30 parts of deionized water in advance to obtain organic amine chain extender dropping liquid for later use; adding 2-4 parts of tertiary amine into b) under the condition of keeping stirring speed and normal temperature, and reacting for 15-30 min; then 90-120 parts of deionized water is added, the rotation speed is increased to 1200-; dripping organic amine chain extender liquid within 10-20min, and carrying out chain extension reaction in a water phase for 1-2 h; then distilling the solvent under reduced pressure to obtain the polyaryletherketone modified waterborne polyurethane resin.
In the step a), the weight part ratio of the binary substituted phenol, the difluoro aromatic hydrocarbon, the weak base and the inert solvent is (18-25): (9-13): (6-8): (40-50); in the step b), the weight part ratio of hexamethylene diisocyanate, linear polyaryletherketone, hydrophilic modifier, catalyst, diluent and alcohol chain extender is (10-14): (27-45): (2-4): (0.01-0.1): (12-18): (3-6); the weight part ratio of the tertiary amine to the deionized water in the step c) is (2-4): (90-120).
The binary substituted phenol is at least one of 1-hydroxy-4- (4-hydroxybenzene) -naphthyridine, 4' -dihydroxybiphenyl, 4- (2-methyl-4-hydroxyphenyl) naphthyridine, 1, 5-dihydroxyanthraquinone, 4- (3-phenyl-4-hydroxyphenyl) -2, 3-naphthyridine-1-ketone and 4- (4-hydroxyphenyl) -2, 3-naphthyridine-1-ketone.
The difluoro aromatic hydrocarbon is at least one of 4,4 '-difluorobenzophenone, 1, 4-di- (4' -fluorobenzoyl) benzene and 1, 3-di (4-fluorobenzoyl) benzene.
The weak base is at least one of sodium carbonate and potassium carbonate.
The inert solvent is at least one of dimethylbenzene, trimethylbenzene, ethylbenzene, methyl ethylbenzene and diethylbenzene.
The hydrophilic modifier is at least one of 2-hydroxypropionic acid, 3-hydroxypropionic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid and glycolic acid; the catalyst is at least one of dibutyltin dilaurate, lithium acetate, tri-n-butylphosphonium, stannous octoate, tin naphthenate, lead naphthenate, cobalt naphthenate, dibutyltin maleate and dibutyltin diacetate; the diluent is at least one of acetone, butanone, cyclohexanone, ethylene glycol dimethyl ether, ethylene glycol dibutyl ether and N-methyl pyrrolidone.
The alcohol chain extender is at least one of ethylene glycol, 1, 2-propylene glycol, 1, 4-butanediol, 1, 6-hexanediol, 1, 5-pentanediol, trimethylolpropane, neopentyl glycol and diethylene glycol; the organic amine chain extender is at least one of ethylenediamine, diethylenetriamine, hexamethylenediamine and piperazine; the tertiary amine is at least one of triethylamine, dimethylethanolamine, trimethylamine and tripropylamine.
The polyaryletherketone modified waterborne polyurethane resin prepared by the preparation method of the polyaryletherketone modified waterborne polyurethane resin has a good application prospect, and the environment-friendly coating prepared by the preparation method has better hardness, wear resistance, water resistance and ethanol resistance.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the hydroxyl-terminated linear polyaryletherketone with low molecular weight is synthesized by stepwise polymerization by controlling the proportion of the binary substituted phenol and the difluoro aromatic hydrocarbon, and the characteristics of good chemical stability and excellent mechanical property of the polyaryletherketone are reserved;
(2) the invention uses linear polyaryletherketone to replace polyether dihydric alcohol, polyester dihydric alcohol, polytetrahydrofuran dihydric alcohol and the like which are commonly used in waterborne polyurethane, and an arylether bond in the polyaryletherketone has better water resistance and solvent resistance compared with an ester bond and an ether bond.
Detailed Description
The polyaryletherketone modified waterborne polyurethane resin of the present invention will be further described with reference to the following examples. It is to be understood that the specific embodiments described herein are merely illustrative of the relevant invention and not restrictive of the invention.
Example 1
A polyaryletherketone modified waterborne polyurethane resin is prepared by first adopting stepwise polymerization to prepare linear low molecular weight hydroxyl-terminated polyaryletherketone, and then using the polyaryletherketone to chemically modify a polyurethane emulsion, wherein the preparation method of the polyaryletherketone modified waterborne polyurethane resin comprises the following steps in parts by weight:
a) preparation of linear polyaryletherketone: under the condition of introducing nitrogen, 18 parts of 4- (4-hydroxyphenyl) -2, 3-naphthyridin-1-one, 9 parts of 1, 3-di (4-fluorobenzoyl) benzene, 6 parts of potassium carbonate and 40 parts of methyl ethylbenzene are added into a reactor provided with a water distribution device, a heating device and a stirring device, the mixture is heated to 150 ℃ under stirring, water generated in the reaction is continuously removed through the water distribution device, the reaction is carried out at the temperature of 150 ℃ for 3 hours, then the temperature is increased to 180 ℃ at the temperature increasing speed of 5 ℃/h, the polymerization is carried out at the temperature of 180 ℃ for 5 hours, and finally an inert solvent is removed through reduced pressure distillation to obtain the linear polyaryletherketone.
b) Polyaryletherketone modified polyurethane prepolymer: in N2Under the protection and stirring conditions, sequentially adding 14 parts of hexamethylene diisocyanate, 45 parts of a) medium linear polyaryletherketone, 4 parts of 3-hydroxypropionic acid, 0.1 part of stannous octoate and 18 parts of butanone into a reactor, heating to 80 ℃, reacting for 5 hours, sampling, detecting, and cooling to 55 ℃ when the measured-NCO value reaches 13%; adding 6 parts of 1, 4-butanediol and 0.1 part of stannous octoate under stirring at the rotating speed of 800rpm for chain extension reaction, starting sampling after 3 hours, cooling to room temperature when the measured-NCO value reaches 4%, and stopping reaction to obtain a modified polyurethane prepolymer;
c) emulsification: dissolving 1.6 parts of ethylenediamine into 23 parts of deionized water in advance to obtain organic amine chain extender dripping liquid for later use; adding 2.4 parts of dimethylethanolamine into the mixture b) under the condition of keeping the stirring speed and the normal temperature, and reacting for 19 min; then 100 parts of deionized water is added, the rotating speed is increased to 1300rpm for emulsification for 30min, and the stirring rotating speed is reduced to 5500 rpm; dripping organic amine chain extender liquid within 15min, and carrying out chain extension reaction in a water phase for 1.5 h; then distilling the solvent under reduced pressure to obtain the polyaryletherketone modified waterborne polyurethane resin.
Example 2
A polyaryletherketone modified waterborne polyurethane resin is prepared by first adopting stepwise polymerization to prepare linear low molecular weight hydroxyl-terminated polyaryletherketone, and then using the polyaryletherketone to chemically modify a polyurethane emulsion, wherein the preparation method of the polyaryletherketone modified waterborne polyurethane resin comprises the following steps in parts by weight:
a) preparation of linear polyaryletherketone: under the condition of introducing nitrogen, 21 parts of 4- (3-phenyl-4-hydroxyphenyl) -2, 3-naphthyridine-1-one, 10 parts of 1, 4-di- (4' -fluorobenzoyl) benzene, 6.5 parts of potassium carbonate and 43 parts of trimethylbenzene are added into a reactor provided with a water distribution device, a heating device and a stirring device, the mixture is heated to 138 ℃ under stirring, water generated in the reaction is continuously removed through the water distribution device, the reaction is carried out at 138 ℃ for 3.4h, then the temperature is increased to 180 ℃ at the temperature increasing speed of 5 ℃/h, the polymerization is carried out at 180 ℃ for 6h under heat preservation, and finally an inert solvent is removed through reduced pressure distillation to obtain the linear polyaryletherketone.
b) Polyaryletherketone modified polyurethane prepolymer: in N2Under the protection and stirring conditions, sequentially adding 10 parts of hexamethylene diisocyanate, 27 parts of a) medium linear polyaryletherketone, 2 parts of 2-hydroxybutyric acid, 0.01 part of dibutyltin maleate and 12 parts of cyclohexanone into a reactor, heating to 100 ℃, reacting for 2 hours, sampling and detecting, and cooling to 70 ℃ when the measured-NCO value reaches 16%; adding 3 parts of 1, 6-hexanediol and 0.01 part of dibutyltin maleate into the mixture under stirring at the rotating speed of 600rpm for chain extension reaction, starting sampling after 2 hours, and cooling to room temperature to stop the reaction when the measured-NCO value reaches 8% to obtain a modified polyurethane prepolymer;
c) emulsification: dissolving 2 parts of hexamethylenediamine into 10 parts of deionized water in advance to obtain an organic amine chain extender dripping liquid for later use; adding 4 parts of trimethylamine into the b) under the conditions of keeping the stirring speed and normal temperature, and reacting for 15 min; then adding 120 parts of deionized water, then increasing the rotating speed to 1200rpm for emulsification for 40min, and reducing the stirring rotating speed to 500 rpm; dripping organic amine chain extender liquid within 20min, and carrying out chain extension reaction for 1h in a water phase; then distilling the solvent under reduced pressure to obtain the polyaryletherketone modified waterborne polyurethane resin.
Example 3
A polyaryletherketone modified waterborne polyurethane resin is prepared by first adopting stepwise polymerization to prepare linear low molecular weight hydroxyl-terminated polyaryletherketone, and then using the polyaryletherketone to chemically modify a polyurethane emulsion, wherein the preparation method of the polyaryletherketone modified waterborne polyurethane resin comprises the following steps in parts by weight:
a) preparation of linear polyaryletherketone: adding 25 parts of 1-hydroxy-4- (4-hydroxybenzene) -naphthyridine, 13 parts of 4,4' -difluorobenzophenone, 8 parts of sodium carbonate and 50 parts of diethylbenzene into a reactor provided with a water distribution device, a heating device and a stirring device under the condition of introducing nitrogen, heating to 130 ℃ under stirring, continuously removing water generated in the reaction by the water distribution device, carrying out heat preservation reaction at 130 ℃ for 4h, then heating to 180 ℃ at the heating rate of 5 ℃/h, carrying out heat preservation polymerization at 180 ℃ for 7h, and finally removing an inert solvent by reduced pressure distillation to obtain the linear polyaryletherketone.
b) Polyaryletherketone modified polyurethane prepolymer: in N2Under the protection and stirring conditions, sequentially adding 12 parts of hexamethylene diisocyanate, 36 parts of a) medium linear polyaryletherketone, 3.1 parts of 4-hydroxybutyric acid, 0.04 part of cobalt naphthenate and 14 parts of ethylene glycol dibutyl ether into a reactor, heating to 90 ℃ for reacting for 3 hours, sampling and detecting, and cooling to 62 ℃ when the measured-NCO value reaches 14.5%; adding 4 parts of 1, 5-pentanediol and 0.03 part of cobalt naphthenate under the stirring of 700rpm for chain extension reaction, starting sampling after 2.4 hours, and cooling to room temperature to stop the reaction when the measured-NCO value reaches 6.3 percent to obtain a modified polyurethane prepolymer;
c) emulsification: dissolving 1 part of piperazine into 30 parts of deionized water in advance to obtain organic amine chain extender dripping liquid for later use; adding 2 parts of triethylamine into the b) under the condition of keeping the stirring speed and normal temperature, and reacting for 30 min; then 90 parts of deionized water is added, then the rotating speed is increased to 1500rpm for emulsification for 20min, and the stirring rotating speed is reduced to 600 rpm; dripping organic amine chain extender liquid within 10min, and carrying out chain extension reaction for 2h in a water phase; then distilling the solvent under reduced pressure to obtain the polyaryletherketone modified waterborne polyurethane resin.
And (4) testing the storage stability: 0.5L of the polyaryletherketone modified waterborne polyurethane resin sample of the embodiment 1-3 is put into a proper plastic container, sealed and put into a constant temperature drying oven at 50 +/-2 ℃, taken out after seven days and put for 3 hours at 23 +/-2 ℃, and no agglomeration, precipitation or gelation phenomenon is generated after stirring.
The modified polyurethane emulsion for the commercial wood lacquer is taken as a comparative example, the wetting dispersant, the leveling agent and the defoaming agent with the same mass fraction are added into the examples 1-3 and the comparative examples under the same condition (the formula is completely the same) to prepare the transparent lacquer, then the transparent lacquer is sprayed on the surface of the oak board for three times (the thickness is about 30 micrometers) under the same condition, and after the lacquer film is completely dried, the performance test results are as the following table 1:
table 1 table for testing performance of examples
As can be seen from Table 1, the clear paint of the embodiment of the invention has better hardness and wear resistance, and has better water resistance and ethanol resistance.
While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes, modifications and variations can be made therein without departing from the spirit and scope of the invention as defined in the following claims.
Claims (7)
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| CN202110091999.5A CN112898531B (en) | 2018-10-15 | 2018-10-15 | Polyaryletherketone modified waterborne polyurethane resin |
| CN201811193476.6A CN109438658B (en) | 2018-10-15 | 2018-10-15 | A kind of polyaryletherketone modified waterborne polyurethane resin |
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| CN114958168B (en) * | 2022-04-20 | 2023-06-20 | 上海库曜新材料有限公司 | Coating composition for high-temperature-resistant superhard wear-resistant coating |
| CN117926597B (en) * | 2024-01-24 | 2024-12-24 | 江西铭邦科技有限公司 | Polished leather prepared from PU slurry and production process and application thereof |
| CN119242245A (en) * | 2024-07-23 | 2025-01-03 | 东莞市新懿电子材料技术有限公司 | A high-toughness UV curing adhesive and its application in polyvinyl chloride and silicone rubber |
| CN118955865B (en) * | 2024-10-14 | 2025-01-24 | 兴邦新材料(山东)有限公司 | Preparation method of high temperature resistant modified polyurethane elastomer |
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| DE1196862B (en) * | 1963-12-06 | 1965-07-15 | Basf Ag | Process for the production of highly elastic moldings from isocyanate-modified polyhydroxyl compounds |
| US4695612A (en) * | 1986-06-23 | 1987-09-22 | General Electric Company | Secondary amine-terminated oligomers and copolyurethanecarbonates prepared therefrom |
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| CN112898531A (en) | 2021-06-04 |
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