JP2011236155A - ジカルボン酸トリアジン活性エステル及び、それを用いて得られるポリアミド樹脂 - Google Patents
ジカルボン酸トリアジン活性エステル及び、それを用いて得られるポリアミド樹脂 Download PDFInfo
- Publication number
- JP2011236155A JP2011236155A JP2010108779A JP2010108779A JP2011236155A JP 2011236155 A JP2011236155 A JP 2011236155A JP 2010108779 A JP2010108779 A JP 2010108779A JP 2010108779 A JP2010108779 A JP 2010108779A JP 2011236155 A JP2011236155 A JP 2011236155A
- Authority
- JP
- Japan
- Prior art keywords
- active ester
- dicarboxylic acid
- triazine
- group
- acid
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 42
- 229920006122 polyamide resin Polymers 0.000 title claims description 27
- GVVAQQJNYPOAIJ-UHFFFAOYSA-N triazine-4,5-dicarboxylic acid Chemical compound OC(=O)C1=CN=NN=C1C(O)=O GVVAQQJNYPOAIJ-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 239000012535 impurity Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 17
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 49
- -1 diamine compound Chemical class 0.000 claims description 44
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910005965 SO 2 Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 5
- 125000000962 organic group Chemical group 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000843 powder Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 7
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000013580 millipore water Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OTLMQCNHFVYECA-UHFFFAOYSA-N 2-(2-carboxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1C(O)=O OTLMQCNHFVYECA-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- ABWQLBWYPYHBHW-UHFFFAOYSA-N 4,6-dimethoxy-1h-1,3,5-triazin-2-one Chemical compound COC1=NC(O)=NC(OC)=N1 ABWQLBWYPYHBHW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LNTGGPJSADTYSG-UHFFFAOYSA-N 2-(2-carbonochloridoylphenoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(Cl)=O LNTGGPJSADTYSG-UHFFFAOYSA-N 0.000 description 2
- PIGCZLUEESSMFP-UHFFFAOYSA-N 2-(2-carbonochloridoylphenyl)sulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(Cl)=O PIGCZLUEESSMFP-UHFFFAOYSA-N 0.000 description 2
- UOFDVLCOMURSTA-UHFFFAOYSA-N 2-(2-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(O)=O UOFDVLCOMURSTA-UHFFFAOYSA-N 0.000 description 2
- BDUPKZTWQYDOGC-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CC=CC=C1C(O)=O BDUPKZTWQYDOGC-UHFFFAOYSA-N 0.000 description 2
- AOFRNZNXMCOXHP-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(O)=O AOFRNZNXMCOXHP-UHFFFAOYSA-N 0.000 description 2
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 2
- NWZSQZIPVJLICE-UHFFFAOYSA-N 2-chloro-4,6-diethoxy-1,3,5-triazine Chemical compound CCOC1=NC(Cl)=NC(OCC)=N1 NWZSQZIPVJLICE-UHFFFAOYSA-N 0.000 description 2
- WPAYYYDSSCOEHN-UHFFFAOYSA-N 2-chloro-4,6-diphenoxy-1,3,5-triazine Chemical compound N=1C(OC=2C=CC=CC=2)=NC(Cl)=NC=1OC1=CC=CC=C1 WPAYYYDSSCOEHN-UHFFFAOYSA-N 0.000 description 2
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 2
- GNIZQCLFRCBEGE-UHFFFAOYSA-N 3-phenylbenzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(Cl)=O GNIZQCLFRCBEGE-UHFFFAOYSA-N 0.000 description 2
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 2
- UYOPTJREJWOZDO-UHFFFAOYSA-N 4,6-diethoxy-1h-1,3,5-triazin-2-one Chemical compound CCOC=1N=C(OCC)NC(=O)N=1 UYOPTJREJWOZDO-UHFFFAOYSA-N 0.000 description 2
- QKVSMSABRNCNRS-UHFFFAOYSA-N 4-(2-methylpropyl)morpholine Chemical compound CC(C)CN1CCOCC1 QKVSMSABRNCNRS-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229920006038 crystalline resin Polymers 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 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
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- DNVDSIHMUVXBGB-UHFFFAOYSA-N (4,5-diamino-2,3-dimethylphenyl)-phenylmethanone Chemical compound NC1=C(N)C(C)=C(C)C(C(=O)C=2C=CC=CC=2)=C1 DNVDSIHMUVXBGB-UHFFFAOYSA-N 0.000 description 1
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MNAOHADFSKNJBS-UHFFFAOYSA-N 1-n,1-n'-diphenylpropane-1,1-diamine Chemical compound C=1C=CC=CC=1NC(CC)NC1=CC=CC=C1 MNAOHADFSKNJBS-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical group CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 description 1
- GABSXTUCLXHJDO-UHFFFAOYSA-N 2-(2-carbonochloridoylbenzoyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1C(Cl)=O GABSXTUCLXHJDO-UHFFFAOYSA-N 0.000 description 1
- IBDYHGDYXJATBB-UHFFFAOYSA-N 2-[(2-carbonochloridoylphenyl)methyl]benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1CC1=CC=CC=C1C(Cl)=O IBDYHGDYXJATBB-UHFFFAOYSA-N 0.000 description 1
- NKGDIYDBPVBXBW-UHFFFAOYSA-N 2-[(2-carboxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1=CC=CC=C1C(O)=O NKGDIYDBPVBXBW-UHFFFAOYSA-N 0.000 description 1
- MUHMDDDWPPOEPM-UHFFFAOYSA-N 2-[2-(2-carbonochloridoylphenyl)propan-2-yl]benzoyl chloride Chemical compound C=1C=CC=C(C(Cl)=O)C=1C(C)(C)C1=CC=CC=C1C(Cl)=O MUHMDDDWPPOEPM-UHFFFAOYSA-N 0.000 description 1
- UFHHHJLKTBTUCR-UHFFFAOYSA-N 2-[2-(2-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1C(C)(C)C1=CC=CC=C1C(O)=O UFHHHJLKTBTUCR-UHFFFAOYSA-N 0.000 description 1
- VCIWJCLDCYYMAU-UHFFFAOYSA-N 2-[2-(6-carboxy-2,3-difluorophenyl)propan-2-yl]-3,4,5,6-tetrafluorobenzoic acid Chemical compound FC1=C(C(=C(C(=O)O)C=C1)C(C)(C)C1=C(C(=O)O)C(=C(C(=C1F)F)F)F)F VCIWJCLDCYYMAU-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 1
- KMRRMZVZRRDKKH-UHFFFAOYSA-N 2-decylpropanedioyl dichloride Chemical compound CCCCCCCCCCC(C(Cl)=O)C(Cl)=O KMRRMZVZRRDKKH-UHFFFAOYSA-N 0.000 description 1
- HPFXKLDSEUWECX-UHFFFAOYSA-N 2-n'-fluoro-2-n'-(2,3,4,5,6-pentafluorophenyl)-2-n-phenylpropane-2,2-diamine Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1N(F)C(C)(C)NC1=CC=CC=C1 HPFXKLDSEUWECX-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical group CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- LXUNPFPFHZALKQ-UHFFFAOYSA-N 4,6-di(propan-2-yloxy)-1h-1,3,5-triazin-2-one Chemical compound CC(C)OC=1N=C(OC(C)C)NC(=O)N=1 LXUNPFPFHZALKQ-UHFFFAOYSA-N 0.000 description 1
- FAHQGPKCCUNXCJ-UHFFFAOYSA-N 4,6-diphenoxy-1H-1,3,5-triazin-2-one Chemical compound N1=C(OC=2C=CC=CC=2)NC(=O)N=C1OC1=CC=CC=C1 FAHQGPKCCUNXCJ-UHFFFAOYSA-N 0.000 description 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- CKDSFRWKHBYHHT-UHFFFAOYSA-N 4-bicyclo[2.2.1]heptanylmethanamine Chemical compound C1CC2CCC1(CN)C2 CKDSFRWKHBYHHT-UHFFFAOYSA-N 0.000 description 1
- IWRVPXDHSLTIOC-UHFFFAOYSA-N 4-phenyldiazenylbenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 IWRVPXDHSLTIOC-UHFFFAOYSA-N 0.000 description 1
- SKKKJNPBIGQNEJ-UHFFFAOYSA-N 9h-fluorene-1,9-diamine Chemical compound C1=CC(N)=C2C(N)C3=CC=CC=C3C2=C1 SKKKJNPBIGQNEJ-UHFFFAOYSA-N 0.000 description 1
- RLORBMWXLFVYEQ-UHFFFAOYSA-N C(CCCCCCC(=O)Cl)(=O)Cl.C(CCCCCC(=O)Cl)(=O)Cl Chemical compound C(CCCCCCC(=O)Cl)(=O)Cl.C(CCCCCC(=O)Cl)(=O)Cl RLORBMWXLFVYEQ-UHFFFAOYSA-N 0.000 description 1
- LPKITZIDHBWGFH-UHFFFAOYSA-N CC1=C[I]=CC=C1 Chemical compound CC1=C[I]=CC=C1 LPKITZIDHBWGFH-UHFFFAOYSA-N 0.000 description 1
- DSTNVVLCYFCZHQ-UHFFFAOYSA-N CC[IH]1=CC=CC(C)=C1 Chemical compound CC[IH]1=CC=CC(C)=C1 DSTNVVLCYFCZHQ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JRCHJMRWQMAVQA-UHFFFAOYSA-N ClC1=NC(=NC(=N1)OCOC(C)C)OCOC(C)C Chemical compound ClC1=NC(=NC(=N1)OCOC(C)C)OCOC(C)C JRCHJMRWQMAVQA-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- SOTIKQDICXJIJA-UHFFFAOYSA-N FC1=C(C(=C(C(=O)Cl)C=C1)C(C)(C)C1=C(C(=O)Cl)C(=C(C(=C1F)F)F)F)F Chemical compound FC1=C(C(=C(C(=O)Cl)C=C1)C(C)(C)C1=C(C(=O)Cl)C(=C(C(=C1F)F)F)F)F SOTIKQDICXJIJA-UHFFFAOYSA-N 0.000 description 1
- GQWNECFJGBQMBO-UHFFFAOYSA-N Molindone hydrochloride Chemical compound Cl.O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 GQWNECFJGBQMBO-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- MRPFKCZNMMVNBU-UHFFFAOYSA-N NC=1C(=C(C=CC=1OC)C1=CC=C(C=C1)OC)N Chemical group NC=1C(=C(C=CC=1OC)C1=CC=C(C=C1)OC)N MRPFKCZNMMVNBU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NBWVWEVIDWXVMD-UHFFFAOYSA-N OC1=NC(=NC(=N1)OC1=CC=CC=C1)OC1=CC=CC=C1.OC1=NC(=NC(=N1)OCCCC)OCCCC Chemical compound OC1=NC(=NC(=N1)OC1=CC=CC=C1)OC1=CC=CC=C1.OC1=NC(=NC(=N1)OCCCC)OCCCC NBWVWEVIDWXVMD-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
- YXEAFBGUFVJJEI-UHFFFAOYSA-N c(cc1)cc2c1[I]=CC=C2 Chemical compound c(cc1)cc2c1[I]=CC=C2 YXEAFBGUFVJJEI-UHFFFAOYSA-N 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- GHAUROKXNSHBAG-UHFFFAOYSA-N cyclopentane-1,1-diamine Chemical compound NC1(N)CCCC1 GHAUROKXNSHBAG-UHFFFAOYSA-N 0.000 description 1
- UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VOLFIDSFKZJSNJ-UHFFFAOYSA-N n,n'-diethyl-n,n'-bis(2-ethylphenyl)methanediamine Chemical compound C=1C=CC=C(CC)C=1N(CC)CN(CC)C1=CC=CC=C1CC VOLFIDSFKZJSNJ-UHFFFAOYSA-N 0.000 description 1
- AKUBZUGGSGGUEF-UHFFFAOYSA-N n,n-diethoxyaniline Chemical compound CCON(OCC)C1=CC=CC=C1 AKUBZUGGSGGUEF-UHFFFAOYSA-N 0.000 description 1
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Landscapes
- Polyamides (AREA)
Abstract
Description
このトリアジン系縮合剤は安価に合成できるうえに、副生成物が水溶性のヒドロキシトリアジン化合物であることから、反応後の後処理が容易であり、リサイクルが可能であることなどの利点により注目されており、例えば特許文献2及び非特許文献1では芳香族ポリアミド樹脂の合成への適用も検討されている。
ここで、2価の芳香族残基とは、芳香族環から2つの水素原子を除いた残基を意味し、例えば、ビフェニルエーテル等の複数の芳香族環を有する化合物において、異なる芳香族環から2つの水素原子を除いた残基も2価の芳香族残基の範疇に含むことができる。
具体的には、2価の芳香族残基は、ベンゼン、ビフェニル、ビフェニルエーテル、ビフェニルスルホン、ビフェニルケトン及びナフタレンの残基等が挙げられる。
具体的には、メチレン基、エチレン基、プロピレン基、ブチレン基、ペンチレン基、ヘキシレン基、ヘプチレン基、オクチレン基、ノニレン基、ドデシレン基およびキシリレン基等が挙げられる。
ここで、炭素数6〜8の芳香族残基とは、炭素数6〜8からなる芳香族の芳香族環から1つの水素原子を除いた残基を意味するものとする。
反応終了後、反応混合物を水やメタノールなどの貧溶媒中に投じて生成物を分離した後、再結晶等によって精製を行って副生成物などを除去することにより、ジカルボン酸トリアジン活性エステルを高純度で得ることができる。
H2N−R3−NH2 (B)
式(B)中、R3は、構造中にO、N、S、F及びSiからなる群から選ばれる1種以上の元素を含む2価の芳香族残基または、炭素数1〜12の2価の有機基を示す。
なお、2価の芳香族残基及び2価の有機基は、上記R1と同様のものを挙げることができる。
この不活性溶媒は、ジカルボン酸トリアジン活性エステルと実質的に反応せず、かつ上記ジアミン化合物とを良好に溶解させる性質を有する他、反応生成物であるポリアミドに対して良溶媒であることが望ましい。
反応終了後、反応混合物を水やメタノールなどの貧溶媒中に投じて重合体を分離した後、再沈殿法等によって精製を行って副生成物や無機塩類などを除去することにより、イオン性不純物の含有量が10ppm以下のポリアミド樹脂を得ることができる。
重量平均分子量が1万未満では、成膜性が悪くポリアミドとしての性質出現が不十分であり、一方100万を超えると、分子量が高すぎて溶剤溶解性が悪くなり、かつ成形加工性が悪くなるおそれがある。
ポリアミド樹脂の分子量を調節する簡便な方法としては、ジカルボン酸トリアジン活性エステル成分あるいはジアミン化合物成分のどちらか一方を過剰に使用する方法を挙げることができる。
温度計、窒素導入管、撹拌器を取り付けたフラスコに、イソフタル酸4.2部、2−クロロ−4,6−ジメトキシ−1,3,5−トリアジン9.7部及びN−メチル−2−ピロリドン100部を加え0℃に冷却した。その後、N−メチルモルホリン7.6部を攪拌下で滴下し、15分間反応させ、下記式(3)
温度計、窒素導入管、撹拌器を取り付けたフラスコに、ジフェニルエーテル−4,4’−ジカルボン酸6.5部、2−クロロ−4,6−ジメトキシ−1,3,5−トリアジン9.7部及びN−メチル−2−ピロリドン100部を加え0℃に冷却した。その後、N−メチルモルホリン7.6部を攪拌下で滴下し、15分間反応させ、下記式(4)
温度計、窒素導入管、撹拌器を取り付けたフラスコに、2−ヒドロキシ−4,6−ジメトキシ−1,3,5−トリアジン3.1部、N−メチル−2−ピロリドン50部及びトリエチルアミン2.0部を加え0℃に冷却した。その後、イソフタル酸ジクロリド2.0部を添加し、20分間反応させ、下記式(3)
温度計、窒素導入管、撹拌器を取り付けたフラスコに窒素ガスパージを施し、4,4’−ジアミノジフェニルエーテル20部、N−メチルピロリドン200部を攪拌溶解し、上記で得られたジジカルボン酸トリアジン活性エステルの樹脂粉末1を44部加え、20℃で6時間反応させ、ポリアミド樹脂の反応液を得た。メタノール2000部に投入し析出した樹脂を濾別し、更にメタノール200部で洗浄した後、メタノール還流して精製した。次いで室温まで冷却した後濾過し、濾過物を乾燥させてポリアミド樹脂粉末1を得た(収率96%)。ゲル浸透クロマトグラフィー(以下、GPC)を用いてポリスチレン換算より求めた分子量(Mw)及び分子量分布(Mw/Mn)は、それぞれ69,000および1.7であった。また、この樹脂粉末4gとミリポア水40gを121℃、20時間で処理し、抽出水をイオンクロマトグラムにてイオン性不純物(P系イオン、Clイオン)を分析した。その結果を表1に示す。
温度計、窒素導入管、撹拌器を取り付けたフラスコに窒素ガスパージを施し、4,4’−ジアミノジフェニルエーテル20部、N−メチルピロリドン200部を攪拌溶解し、上記で得られたジカルボン酸トリアジン活性エステルの樹脂粉末2を54部加え、20℃で6時間反応させ、ポリアミド樹脂の反応液を得た。メタノール2000部に投入し析出した樹脂を濾別し、更にメタノール200部で洗浄した後、メタノール還流して精製した。次いで室温まで冷却した後濾過し、濾過物を乾燥させてポリアミド樹脂粉末2を得た(収率98%)。GPCを用いてポリスチレン換算より求めた分子量(Mw)及び分子量分布(Mw/Mn)は、それぞれ59,000及び1.8であった。また、この樹脂粉末4gとミリポア水40gを121℃、20時間で処理し、抽出水をイオンクロマトグラムにてイオン性不純物(P系イオン、Clイオン)を分析した。その結果を表1に示す。
温度計、窒素導入管、撹拌器を取り付けたフラスコに窒素ガスパージを施し、イソフタル酸16.0部、4,4’−ジアミノジフェニルエーテル20.0部、塩化リチウム1.0部、N−メチルピロリドン108.0部、ピリジン23.0部を加え撹拌溶解させた後、亜りん酸トリフェニル50.0部を加えて90℃で8時間反応させ、ポリアミド樹脂の反応液を得た。メタノール1000部に投入し析出した樹脂を濾別し、更にメタノール200部で洗浄した後、メタノール還流して精製した。次いで室温まで冷却した後濾過し、濾過物を乾燥させて比較例樹脂粉末1を得た(収率96%)。GPCを用いてポリスチレン換算より求めた分子量(Mw)及び分子量分布(Mw/Mn)は、それぞれ71,000及び2.1であった。この樹脂粉末4gとミリポア水40gを121℃、20時間で処理し、抽出水をイオンクロマトグラムにてイオン性不純物(P系イオン、Clイオン)を分析した。その結果を表1に示す。
比較例樹脂粉末1の4,4’−ジアミノジフェニルエーテルを3,4’−ジアミノジフェニルエーテルに変更した以外は同様にして、ポリアミド樹脂の反応液と比較例樹脂粉末2を得た(収率98%)。GPCを用いてポリスチレン換算より求めた分子量(Mw)及び分子量分布(Mw/Mn)は、それぞれ63,000及び1.9であった。この樹脂粉末4gとミリポア水40gを121℃、20時間で処理し、抽出水をイオンクロマトグラムにてイオン性不純物(P系イオン、Clイオン)を分析した。結果を表1に示した。
Claims (5)
- R2が、炭素数1〜4のアルキル基である請求項1に記載のジカルボン酸トリアジン活性エステル。
- 式(1)の、R4が水素原子であり、Xが直接結合、O、SO2又はCOである請求項3に記載のジカルボン酸トリアジン活性エステル。
- 請求項1〜4のいずれかに記載のジカルボン酸トリアジン活性エステルとジアミン化合物とを重合反応により得られるポリアミド樹脂であって、
重量平均分子量が10,000〜1,000,000の範囲であり、かつ、イオン性不純物の含有量が10ppm以下であるポリアミド樹脂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010108779A JP5669174B2 (ja) | 2010-05-10 | 2010-05-10 | ジカルボン酸トリアジン活性エステルの結晶 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010108779A JP5669174B2 (ja) | 2010-05-10 | 2010-05-10 | ジカルボン酸トリアジン活性エステルの結晶 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014212853A Division JP5777126B2 (ja) | 2014-10-17 | 2014-10-17 | ポリアミド樹脂の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011236155A true JP2011236155A (ja) | 2011-11-24 |
JP5669174B2 JP5669174B2 (ja) | 2015-02-12 |
Family
ID=45324547
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010108779A Active JP5669174B2 (ja) | 2010-05-10 | 2010-05-10 | ジカルボン酸トリアジン活性エステルの結晶 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5669174B2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013245206A (ja) * | 2012-05-28 | 2013-12-09 | Iwate Univ | ヒドロキシ基含有芳香族ジアミン、ポリアミド樹脂、樹脂組成物、及び、それらの用途 |
CN111108145A (zh) * | 2017-09-15 | 2020-05-05 | 大金工业株式会社 | 聚苯并咪唑、其前体聚酰胺和它们的制造方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009074038A (ja) * | 2007-08-29 | 2009-04-09 | Sumitomo Bakelite Co Ltd | ポリベンゾオキサゾール前駆体の製造方法 |
-
2010
- 2010-05-10 JP JP2010108779A patent/JP5669174B2/ja active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009074038A (ja) * | 2007-08-29 | 2009-04-09 | Sumitomo Bakelite Co Ltd | ポリベンゾオキサゾール前駆体の製造方法 |
Non-Patent Citations (5)
Title |
---|
JPN6014020855; Bioscience, Biotechnology, and Biochemistry 73(8), 2009, 1764-1772 * |
JPN6014020856; 高分子論文集 64(4), 2007, 231-236 * |
JPN6014020857; 和光純薬時報 72(2), 2004, 8-11 * |
JPN6014020858; Journal of the American Chemical Society 127(48), 2005, 16912-16920 * |
JPN6014020859; Chemistry Letters 31(1), 2002, 66-67 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013245206A (ja) * | 2012-05-28 | 2013-12-09 | Iwate Univ | ヒドロキシ基含有芳香族ジアミン、ポリアミド樹脂、樹脂組成物、及び、それらの用途 |
CN111108145A (zh) * | 2017-09-15 | 2020-05-05 | 大金工业株式会社 | 聚苯并咪唑、其前体聚酰胺和它们的制造方法 |
US11548983B2 (en) | 2017-09-15 | 2023-01-10 | Daikin Industries, Ltd. | Polybenzimidazole, precursor polyamide thereof, and method for producing same |
US11655339B2 (en) | 2017-09-15 | 2023-05-23 | Daikin Industries, Ltd. | Polybenzimidazole, precursor polyamide thereof, and method for producing same |
CN111108145B (zh) * | 2017-09-15 | 2023-09-15 | 大金工业株式会社 | 聚苯并咪唑、其前体聚酰胺和它们的制造方法 |
US11932729B2 (en) | 2017-09-15 | 2024-03-19 | Daikin Industries, Ltd. | Polybenzimidazole, precursor polyamide thereof, and method for producing same |
Also Published As
Publication number | Publication date |
---|---|
JP5669174B2 (ja) | 2015-02-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10619009B2 (en) | Ortho-substituted triptycene-based diamines, monomers, and polymers, methods of making and uses thereof | |
JP3538689B2 (ja) | ポリアミン樹脂及びその製造方法 | |
KR20110134511A (ko) | 폴리아믹산알킬에스테르를 함유하는 폴리이미드 전구체 조성물 | |
KR101339321B1 (ko) | 박막 성형품 | |
Hsiao et al. | Synthesis and characterization of novel organosoluble and thermally stable polyamides bearing triptycene in their backbones | |
JP5564684B2 (ja) | 芳香族ジアミン及びその製造方法並びに樹脂 | |
JP5669174B2 (ja) | ジカルボン酸トリアジン活性エステルの結晶 | |
Zhao et al. | Preparation and properties of three novel poly (phosphazene‐aryl amide) s containing cyclotriphosphazene structures | |
JP2011256219A (ja) | ポリベンゾオキサゾール樹脂及びその前駆体樹脂 | |
KR102249696B1 (ko) | 실란 커플링제 및 그의 제조 방법, 프라이머 조성물 및 도료 조성물 | |
JP5777126B2 (ja) | ポリアミド樹脂の製造方法 | |
JP5546210B2 (ja) | 芳香族ジアミン化合物及びその製造方法並びに合成樹脂 | |
JP6108561B2 (ja) | 熱硬化性樹脂、及び熱硬化性樹脂組成物 | |
WO2019054471A1 (ja) | ポリベンゾイミダゾール、その前駆体ポリアミド及びそれらの製造方法 | |
JP2009074038A (ja) | ポリベンゾオキサゾール前駆体の製造方法 | |
JPH04182466A (ja) | ビストリメリティックイミド類の製造方法 | |
Tsay et al. | Synthesis and properties of fluorinated polyamideimides with high solubility | |
Liaw et al. | Synthesis and characterization of norbornane‐containing cardo polyamides | |
JP2004035638A (ja) | 新規ゴム変性ポリアミドおよびその製造法 | |
Shockravi et al. | Synthesis and properties of novel fluorinated polyamides based on noncoplanar sulfoxide containing aromatic bis (ether amine) | |
JP4514037B2 (ja) | 芳香族ポリアミド樹脂の製造方法 | |
Agrawal et al. | Facile synthesis of new thermally stable and organosoluble polyamide-imides based on non-coplaner phosphorus and silicon containing amines | |
Banihashemi et al. | Synthesis and characterization of new aromatic poly (amide-imide) s derived from bis (3-trimellitimidophenyl) phenyl phosphine oxide and various aromatic diamines | |
JP7184135B2 (ja) | 重合性s-トリアジン誘導体及びこれを用いた硬化性組成物、並びにこれらを用いた硬化物及び成形材料 | |
JP4518853B2 (ja) | ポリアミド樹脂の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130502 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130522 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20130522 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140508 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140527 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140725 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140819 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141017 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20141111 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141211 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5669174 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313117 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |