CN114907564A - High-binding-force bio-based high-temperature-resistant polyamide and preparation method and application thereof - Google Patents
High-binding-force bio-based high-temperature-resistant polyamide and preparation method and application thereof Download PDFInfo
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- CN114907564A CN114907564A CN202210313570.0A CN202210313570A CN114907564A CN 114907564 A CN114907564 A CN 114907564A CN 202210313570 A CN202210313570 A CN 202210313570A CN 114907564 A CN114907564 A CN 114907564A
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- temperature
- binding
- resistant polyamide
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 72
- 229920002647 polyamide Polymers 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 19
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002844 melting Methods 0.000 claims abstract description 17
- 230000008018 melting Effects 0.000 claims abstract description 17
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical compound CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- -1 phosphorus compound Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000002981 blocking agent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 abstract description 35
- 229910002027 silica gel Inorganic materials 0.000 abstract description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 33
- 239000000463 material Substances 0.000 abstract description 20
- 238000010521 absorption reaction Methods 0.000 abstract description 17
- 150000004985 diamines Chemical class 0.000 abstract description 10
- 230000000052 comparative effect Effects 0.000 description 25
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 6
- 229920006122 polyamide resin Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000010998 test method Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 229920006021 bio-based polyamide Polymers 0.000 description 3
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920006119 nylon 10T Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920006128 poly(nonamethylene terephthalamide) Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 229910001374 Invar Inorganic materials 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006375 polyphtalamide Polymers 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/483—Containers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/58—Optical field-shaping elements
- H01L33/60—Reflective elements
Landscapes
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Abstract
The invention relates to high-binding-force bio-based high-temperature-resistant polyamide and a preparation method and application thereof. The high-bonding-force bio-based high-temperature-resistant polyamide comprises pentanediamine and dibasic acid. According to the polyamide provided by the invention, furan dicarboxylic acid and terephthalic acid in a specific ratio are used as dibasic acid, and pentamethylene diamine in a bio-based source is used as diamine, so that the bonding force with silica gel is effectively improved, the melting point is high, the polyamide has better high temperature resistance, and the polyamide also has lower water absorption rate and lower shrinkage rate, and is suitable for being used as an LED reflection support material, especially an outdoor LED reflection support material.
Description
Technical Field
The invention belongs to the field of engineering plastic application, and particularly relates to high-binding-force bio-based high-temperature-resistant polyamide and a preparation method and application thereof.
Background
The LED reflection support is used as a chip carrier, has both the electric conduction function and the heat conduction function, and is an indispensable key auxiliary material for LED devices. The materials used as LED support are mainly high temperature resistant polyamide (PPA) and high temperature resistant polyester (cyclohexyldimethyl terephthalamide, PCT). The high-temperature resistant polyamide (mainly comprising PA46, PA6T and PA9T) has high initial whiteness, good heat resistance, high fluidity, low cost and suitability for injection molding process, and is the mainstream material of the LED bracket at present.
The LED packaging adhesive mainly comprises epoxy resin and silica gel, the silica gel has the remarkable characteristics of excellent mechanical property, ageing resistance, good thermal stability, weather resistance, flexibility, high light transmittance, small internal stress, low hygroscopicity and the like, and compared with the epoxy resin, the performance of the silica gel can better meet the packaging requirement of high-power and high-brightness LED products. Therefore, silica gel is rapidly replacing epoxy resin, and becomes a new generation of more ideal LED packaging material.
The main material of the LED reflecting bracket for the display screen is PA6T/66 (copolymer of hexamethylene diamine, terephthalic acid and adipic acid), because compared with PA9T and PA10T, PA6T/66 has higher amido bond density, and can form hydrogen bond with hydrosilation groups and silanol groups in a silica gel matrix, and the bonding force between the LED reflecting bracket and the silica gel is improved to a certain extent.
However, with the rapid development of LEDs, LED lamp beads have begun to be applied to the field of outdoor display screens. For the application field of outdoor display screens, LED lamp beads need to be in high-temperature and high-humidity environments such as high-temperature insolation or rainwater erosion for a long time, under the condition, the binding force of PA6T/66 and silica gel is still not enough to meet the requirement, and the problem of separation of plastic and silica gel exists. And the PA6T/66 has high water absorption rate, and is easy to generate dimensional deformation in an outdoor high-humidity environment, so that the problem of cracking of lamp beads is caused. At present, no suitable high-temperature resistant polyamide resin matrix applied to LED outdoor display screens exists.
In addition, the hexamethylene diamine monomer in PA6T/66 is generally derived from petroleum, and does not meet the requirement of green sustainable development under the current situations of excessive petroleum resource consumption, sharp increase of carbon dioxide emission and aggravation of greenhouse effect.
The prior patent discloses a full-bio-based polyamide and a preparation method thereof, and the full-bio-based polyamide and the preparation method thereof are used for obtaining high-performance environment-friendly polyamide by taking bio-based furan dicarboxylic acid and aliphatic diamine as raw materials. However, the polyamide has poor adhesion to silica gel.
Therefore, the development of the bio-based polyamide with strong binding force with silica gel to meet the performance of the outdoor display screen and meet the requirement of green sustainable development has important research significance and application value.
Disclosure of Invention
The invention aims to overcome the defects or shortcomings that the binding force of polyamide and silica gel in the prior art is not strong and the requirement of green sustainable development is not met, and provides the high-binding-force bio-based high-temperature-resistant polyamide. According to the polyamide provided by the invention, furan dicarboxylic acid and terephthalic acid in a specific ratio are used as dibasic acid, and pentamethylene diamine in a bio-based source is used as diamine, so that the binding force with silica gel is effectively improved, the melting point is high, the polyamide has better high temperature resistance, lower water absorption and lower shrinkage, and the polyamide is suitable for being used as an LED reflection support material, especially an outdoor LED reflection support material; moreover, the selection of the biological-based pentanediamine also solves the problems of environmental pollution and resource shortage to a certain extent, is beneficial to constructing a sustainable development society, and meets the requirement of green sustainable development.
The invention also aims to provide a preparation method of the high-binding-force bio-based high-temperature-resistant polyamide.
Another object of the present invention is to provide the use of bio-based high temperature resistant polyamides with high binding capacity in the preparation of LED reflective supports.
In order to achieve the purpose, the invention adopts the following technical scheme:
the high-binding-force bio-based high-temperature-resistant polyamide comprises the following components in parts by mole:
100 parts of dibasic acid, 100 parts of sodium bicarbonate,
95-105 parts of pentamethylene diamine,
the dibasic acid is composed of furan dicarboxylic acid and terephthalic acid, and the mole fraction of furan dicarboxylic acid in the dibasic acid monomer is 10-50%.
The inventor of the invention researches and discovers that the types of the dibasic acid monomer and the diamine monomer have great influence on the binding force of the obtained polyamide and silica gel. When furan dicarboxylic acid and terephthalic acid in a specific molar ratio are selected as dibasic acid monomers and pentamethylene diamine is selected as a diamine monomer, the obtained polyamide and silica gel have good binding force, high melting point and good high temperature resistance; in addition, the material has low water absorption rate and low shrinkage rate, and is suitable for being used as an LED reflection bracket material, particularly an outdoor LED reflection bracket material. The polyamide obtained from the specific monomer has proper amide bond density, so that the polyamide has stronger molecular polarity, can form stronger intermolecular force with silica gel molecules and has better binding force; on the other hand, the water absorption rate and the shrinkage rate can be effectively reduced. If the molar consumption of the furandicarboxylic acid is too low, the obtained polyamide has too high melting point and poor processability, and is not suitable for preparing an LED reflecting bracket; if the molar amount of the furan dicarboxylic acid is too high, the obtained polyamide has too low melting point, poor temperature resistance, too high water absorption and large shrinkage. If other diamine monomers are selected, the density of amido bond is reduced, and the binding force with silica gel is weaker.
Preferably, the mole fraction of the furan dicarboxylic acid in the dibasic acid monomer is 20-40%.
Preferably, the melting point of the high-bonding-force bio-based high-temperature-resistant polyamide is 280-330 ℃.
Polyamide melting point test method: reference is made to ASTM D3418-2003; the specific test method comprises the following steps: testing the melting point of the sample by adopting a Perkin Elmer Dimond DSC analyzer; nitrogen atmosphere, the flow rate is 50 mL/min; during testing, the temperature is raised to 350 ℃ at the speed of 20 ℃/min, the temperature is kept for 2min at the speed of 350 ℃, the thermal history of the resin is removed, then the resin is cooled to 50 ℃ at the speed of 20 ℃/min, the temperature is kept for 2min at the temperature of 50 ℃, the temperature is raised to 350 ℃ at the speed of 20 ℃/min, and the endothermic peak temperature at the moment is set as the melting point Tm.
Preferably, the content of the terminal amino group of the high-bonding-force bio-based high-temperature resistant polyamide is 40-56 mol/t.
Method for testing content of amino-terminated groups of polyamide: titrating the content of terminal amino groups of the sample by using a full-automatic potentiometric titrator; 0.5g of polyamide is taken, 45mL of phenol and 3mL of anhydrous methanol are added, heating and refluxing are carried out, after a sample is observed to be completely dissolved, the temperature is cooled to room temperature, and the content of terminal amino groups is determined by using a calibrated hydrochloric acid standard solution.
Preferably, the content of the terminal carboxyl group of the high-bonding-force bio-based high-temperature resistant polyamide is 72-90 mol/t.
Method for testing carboxyl end group content of polyamide: titrating the content of terminal carboxyl of the sample by using a full-automatic potentiometric titrator; 0.5g of polymer is taken and added with 50mL of o-cresol for refluxing and dissolution, 400 mu L of formaldehyde solution is rapidly added after cooling, and the content of terminal carboxyl is titrated by using a calibrated KOH-ethanol solution.
Preferably, the relative viscosity of the high-bonding-force bio-based high-temperature-resistant polyamide is 2.00-2.30.
Polyamide relative viscosity test method: reference GB12006.1-2009, polyamide viscosity number determination method; the specific test method comprises the following steps: the relative viscosity η r of a polyamide with a concentration of 0.25g/dl is measured in 98% concentrated sulfuric acid at 25 ± 0.01 ℃;
methods of preparing polyamides conventional in the art can be used in the present invention. The invention also provides a better preparation method.
The preparation method of the high-binding-force bio-based high-temperature-resistant polyamide comprises the following steps: s1: mixing pentanediamine and dibasic acid, adding a blocking agent, a catalyst and water, and stirring for reaction under an inert atmosphere to obtain a prepolymerization product;
s2: and (3) tackifying the prepolymerization product to obtain the high-binding-force bio-based high-temperature-resistant polyamide.
Catalysts and endcapping agents commonly used in the art for preparing polyamides may be used in the present invention.
Preferably, the catalyst in S1 is a phosphorus compound.
More preferably, the catalyst in S1 is one or more of the following substances and salts or esters thereof: phosphoric acid, phosphorous acid, hypophosphorous acid, phenylphosphonic acid or phenylphosphinic acid.
Specifically, the salt is a cation having a valence of 1+ to 3+ (e.g., Na) + 、K + 、Mg 2+ 、Ga 2+ 、Zn 2+ Or Al 3+ ) The salt formed.
The ester is triphenyl phosphate, triphenyl phosphite, etc.
Preferably, the end-capping agent is one or more of aliphatic, cycloaliphatic or aromatic monocarboxylic acids or monoamines, or monofunctional compounds that can react with amino or carboxyl groups.
More preferably, the monocarboxylic acid is one or more of acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, lauric acid, stearic acid, 2-ethylhexanoic acid, cyclohexanoic acid or benzoic acid
More preferably, the monoamine is one or more of butylamine, pentylamine, hexylamine, 2-ethylhexylamine, n-octylamine, n-dodecylamine, n-tetradecylamine, n-hexadecylamine, stearylamine, cyclohexylamine, 3- (cyclohexylamino) propylamine, methylcyclohexylamine, dimethylcyclohexylamine, benzylamine or 2-phenylethylamine.
More preferably, the monofunctional compound is one or more of anhydride, isocyanate, acyl halide or ester.
Preferably, the stirring reaction in S1 is carried out by: heating to 210-270 ℃ under the stirring condition, keeping the pressure at 2.0-3.1 MPa, continuously stirring for 0.5-3 h under constant pressure, and drying the reaction product to obtain the prepolymer.
Preferably, the weight amount of the catalyst is 0.01-0.5%, preferably 0.1% of the total weight amount of the pentanediamine, the dibasic acid and the benzoic acid.
Preferably, the molar amount of the end-capping agent is 0 to 5 percent, preferably 2.5 percent of the total molar amount of the pentanediamine and the dibasic acid.
Preferably, the weight amount of the water is 10-50% of the total weight of the whole stirring reaction system, and is preferably 30%; the water is preferably deionized water.
Preferably, the tackifying reaction is carried out by the following process: performing solid-phase tackifying on the prepolymer for 5-20 hours at 200-270 ℃ under the vacuum condition of 10-1000 Pa; preferably, the solid phase thickening is carried out at 250 ℃ under a vacuum condition of 50Pa for 10 hours.
The application of the high-bonding-force bio-based high-temperature-resistant polyamide in the preparation of the LED reflecting bracket is also in the protection scope of the invention.
The high-binding-force bio-based high-temperature-resistant polyamide has the advantages of strong binding force, high temperature resistance, low water absorption and low shrinkage, can be widely used for preparing LED reflecting supports, particularly outdoor LED reflecting supports, and can be applied to LED outdoor display screens.
Compared with the prior art, the invention has the following beneficial effects:
according to the polyamide provided by the invention, the furan dicarboxylic acid and the terephthalic acid in a specific ratio are used as the dibasic acid, so that the binding force with silica gel is effectively improved, the melting point is high, the polyamide has better high temperature resistance, lower water absorption and lower shrinkage rate, and the polyamide is suitable for being used as an LED reflection support material, especially an outdoor LED reflection support material.
Detailed Description
The invention is further illustrated by the following examples. These examples are intended to illustrate the invention and are not intended to limit the scope of the invention. Experimental procedures without specific conditions noted in the examples below, generally according to conditions conventional in the art or as suggested by the manufacturer; the raw materials, reagents and the like used are, unless otherwise specified, those commercially available from the conventional markets and the like. Any insubstantial changes and substitutions made by those skilled in the art based on the present invention are intended to be covered by the claims.
Some of the reagents selected in the examples and comparative examples of the present invention are described below:
dibasic acid:
furan dicarboxylic acid: the purity of the product is 98 percent and the product is purchased from Ningbo materials of Chinese academy of sciences;
terephthalic acid: purity 98%, purchased from Sigma-Aldrich;
adipic acid: purity 98%, purchased from Sigma-Aldrich;
diamine (b):
pentanediamine: the purity is 98 percent, and the product is purchased from Shanghai Kaiser chemical Co., Ltd;
hexamethylene diamine: purity 98%, purchased from Sigma-Aldrich;
decamethylenediamine: 98% purity, available from invar nylon ltd;
benzoic acid: analytically pure, commercially available;
sodium hypophosphite: analytically pure, commercially available;
benzoic acid: analytically pure, commercially available;
silica gel: LED packaging silica gel, UH-6950-1(AB gel), commercially available from Shenzhen Yongxinren science and technology Limited.
It is to be understood that, unless otherwise specified, the examples or comparative examples include all of the same commercially available products.
The preparation method of the polyamide of each example and comparative example of the invention is as follows: weighing the raw materials according to the proportion, and adding the reaction raw materials (diamine and dibasic acid) into a pressure kettle which is provided with a magnetic coupling stirring device, a condenser pipe, a gas phase port, a feeding port and a pressure explosion-proof port according to the proportion in the table; adding benzoic acid, sodium hypophosphite (catalyst) and deionized water; the amount of benzoic acid material is 2.5 percent of the total amount of diamine and diacid, the weight of sodium hypophosphite is 0.1 percent of the weight of the other materials except deionized water, and the weight of the deionized water is 30 percent of the total material weight; vacuumizing, filling high-purity nitrogen as a protective gas, and raising the temperature to 230 ℃ under the stirring condition, wherein the pressure is 2.2 MPa; the reaction was continued for 2 hours at a constant temperature of 230 ℃ and constant pressure of 2.2MPa, the pressure was kept constant by removing the water formed, after the reaction was completed, the discharge was carried out, the prepolymer was vacuum-dried at 80 ℃ for 24 hours to obtain a prepolymerization product, which was solid-phase tackified at 250 ℃ under a vacuum of 50Pa for 10 hours to obtain polyamide.
The polyamides of the examples and comparative examples of the invention were tested as follows:
(1) polyamide water absorption: the samples were injection molded into 20mm by 2mm parts, the weight of which was recorded as a 0. Then, after placing it in 95 ℃ water for 240 hours, the weight was weighed as a 1. The water absorption is (a1-a0)/a0 × 100%.
(2) Shrinkage of polyamide: the samples were injection moulded into 20mm x 10mm x 2mm parts and then placed in water at 95 ℃ for 240h, according to ISO 294-4: 2001 standard measures shrinkage after water absorption.
(3) Silica gel binding force: a sample of the polyamide resin composition was injection-molded into a size of 80X 20X 2.0 mm. The test method comprises the following steps: uniformly mixing the silica gel A glue and the silica gel B glue in a mass ratio of 1:4, dripping 0.02g of the mixture to one end of the surface of one sample, pressing the silica gel by one end of the other sample, and fixing the silica gel by a clamp. And then putting the sample piece into an oven, pre-curing for 1h at the temperature of 80 ℃, then heating to 150 ℃, and continuing to cure for 4 h. The cured sample specimens were subjected to tensile testing at a tensile rate of 10mm/min and the tensile force was recorded. The bonding force of the polyamide and the silica gel is represented by the tensile strength, and the tensile strength is not lower than 600, so that the use requirement is met.
Examples 1 to 7
This example provides a series of high binding bio-based high temperature resistant polyamides as shown in table 1.
TABLE 1 EXAMPLES 1 TO 7 (parts)
Comparative examples 1 to 9
This comparative example provides a series of polyamides with the amounts of the components in the formulation shown in Table 2.
TABLE 2 COMPARATIVE EXAMPLES 1 to 9 (parts)
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | Comparative example 9 | |
| Furan dicarboxylic acid/mol | 5 | 55 | / | / | / | 30 | 30 | / | 100 |
| Terephthalic acid/mol | 95 | 45 | 70 | 70 | 100 | 70 | 70 | 100 | / |
| Adipic acid/mol | / | / | 30 | 30 | / | / | / | / | / |
| Pentanediamine/mol | 100 | 100 | 100 | / | / | / | / | 100 | 100 |
| Hexamethylenediamine per mole | / | / | / | 100 | / | 100 | / | / | / |
| Decamethylenediamine per mole | / | / | / | / | 100 | / | 100 | / | / |
| Relative viscosity eta r | 2.25 | 2.21 | 2.19 | 2.21 | 2.20 | 2.18 | 2.19 | 2.20 | 2.17 |
| Terminal amino group/mol/t | 44 | 47 | 49 | 45 | 44 | 49 | 43 | 43 | 42 |
| Terminal carboxyl group/mol/t | 75 | 72 | 74 | 73 | 75 | 78 | 77 | 73 | 74 |
| Melting Point Tm/. degree.C | 345 | 274 | 327 | 322 | 317 | 298 | 284 | 351 | 189 |
| Water absorption/%) | 2.6 | 4.4 | 5.3 | 5.2 | 1.6 | 3.2 | 1.6 | 2.5 | 5.7 |
| Shrinkage ratio% | 0.3/0.7 | 1.0/1.5 | 1.5/2.0 | 1.5/1.9 | 0.2/0.6 | 0.5/1.0 | 0.2/0.6 | 0.2/0.7 | 1.7/2.2 |
| Breaking force/N | 576 | 648 | 556 | 428 | 275 | 443 | 294 | 534 | 672 |
The test results of the polyamides provided in the respective examples and comparative examples are shown in tables 1 and 2.
According to the test results, the high-bonding-force bio-based high-temperature-resistant polyamide and the silica gel have good bonding force, the breaking force is over 633N, the melting point is 280-330 ℃, and the high-temperature-resistant polyamide and the silica gel have good high-temperature resistance and processing performance; in addition, the water absorption rate is lower than 4.0%, the shrinkage rate is lower than 0.8%/1.3%, and the comprehensive performance of the embodiment 3 is the best, so that the material is suitable for being used as an outdoor LED reflection support material. In comparative example 1, in which furan dicarboxylic acid was used in an excessively small molar amount and terephthalic acid was used in an excessively large molar amount, the melting point of the polyamide resin was 345 ℃ and was close to the decomposition temperature of the polyamide resin, and the processability was poor. In comparative example 2, the furandicarboxylic acid with excessive molar dosage and the terephthalic acid with excessive molar dosage are selected, the melting point is 274 ℃, the temperature resistance is poor, although certain silica gel binding force is provided, the water absorption rate is 4.4%, the shrinkage rate is 1.0%/1.5%, both are high, and the preparation method is difficult to be used in the field of outdoor LED reflection bracket materials. Comparative examples 3 and 4 are conventional formulations of PA5T/56 and PA6T/66, respectively, with water absorption greater than 5.2%, shrinkage greater than 1.5%/1.9%, and silica gel bond breaking force less than 556, with weaker silica gel bonding force, not suitable for the harsh environment of high temperature, high humidity of outdoor LEDs. Comparative example 5 is PA10T, which has excellent low water absorption and low shrinkage, and high dimensional stability, but the silica gel has a tensile strength of only 275N, and has a poor bonding strength with silica gel, and thus cannot be applied to the field of outdoor LED reflective supports. Comparative example 6 has hexamethylenediamine as diamine and has poor binding force with silica gel; comparative example 7, which uses decamethylene diamine as the diamine, has poor binding force with silica gel. Comparative example 8 only selects terephthalic acid, the polyamide resin has too high melting point and poor processability; comparative example 9 only selects furandicarboxylic acid, the polyamide resin has too low melting point, poor temperature resistance, high water absorption and large shrinkage.
It will be appreciated by those of ordinary skill in the art that the examples provided herein are intended to assist the reader in understanding the principles of the invention and are to be construed as being without limitation to such specifically recited examples and embodiments. Those skilled in the art can make various other specific changes and combinations based on the teachings of the present invention without departing from the spirit of the invention, and these changes and combinations are within the scope of the invention.
Claims (10)
1. The high-binding-force bio-based high-temperature-resistant polyamide is characterized by comprising the following components in parts by mole:
100 parts of dibasic acid,
95-105 parts of pentamethylene diamine,
the dibasic acid is composed of furan dicarboxylic acid and terephthalic acid, and the mole fraction of furan dicarboxylic acid in the dibasic acid monomer is 10-50%.
2. The high-binding-force bio-based high-temperature resistant polyamide as claimed in claim 1, wherein the molar fraction of furandicarboxylic acid in the diacid monomer is 20-40%.
3. The high-binding-force bio-based high-temperature-resistant polyamide as claimed in claim 1, wherein the melting point of the high-binding-force bio-based high-temperature-resistant polyamide is 280-330 ℃.
4. The high-binding-force bio-based high-temperature-resistant polyamide as claimed in claim 1, wherein the content of the terminal amino group of the high-binding-force bio-based high-temperature-resistant polyamide is 40-56 mol/t.
5. The high-binding-force bio-based high-temperature-resistant polyamide as claimed in claim 1, wherein the content of terminal carboxyl groups of the high-binding-force bio-based high-temperature-resistant polyamide is 72-90 mol/t.
6. The high-binding-force bio-based high-temperature-resistant polyamide as claimed in claim 1, wherein the high-binding-force bio-based high-temperature-resistant polyamide has a relative viscosity of 2.00-2.30.
7. The preparation method of the high-binding-force bio-based high-temperature-resistant polyamide as claimed in any one of claims 1 to 6, characterized by comprising the following steps:
s1: mixing pentanediamine and dibasic acid, adding a blocking agent, a catalyst and water, and stirring for reaction under an inert atmosphere to obtain a prepolymerization product;
s2: and (3) tackifying the prepolymerization product to obtain the high-binding-force bio-based high-temperature-resistant polyamide.
8. The method for preparing high-binding force bio-based high temperature resistant polyamide according to claim 7, wherein the catalyst in S1 comprises phosphorus compound;
the end capping agent in S1 is one or more of aliphatic, cycloaliphatic or aromatic monocarboxylic acid or monoamine, or monofunctional compound capable of reacting with amino or carboxyl.
9. The method for preparing high-binding-force bio-based high-temperature resistant polyamide according to claim 7, wherein the stirring reaction in the step S1 comprises: heating to 210-270 ℃ under the stirring condition, keeping the pressure at 2.0-3.1 MPa, continuously stirring for 0.5-3 h under constant pressure, and drying the reaction product to obtain the prepolymer.
10. The application of the high-binding-force bio-based high-temperature-resistant polyamide disclosed by any one of claims 1-6 in preparation of an LED reflection bracket.
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