DE1770569A1 - Alkoxy- und Hydroxypolyamide - Google Patents
Alkoxy- und HydroxypolyamideInfo
- Publication number
- DE1770569A1 DE1770569A1 DE19681770569 DE1770569A DE1770569A1 DE 1770569 A1 DE1770569 A1 DE 1770569A1 DE 19681770569 DE19681770569 DE 19681770569 DE 1770569 A DE1770569 A DE 1770569A DE 1770569 A1 DE1770569 A1 DE 1770569A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- bis
- radicals
- range
- carboxyphenyl
- 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.)
- Pending
Links
- 239000004952 Polyamide Substances 0.000 title claims description 48
- 229920002647 polyamide Polymers 0.000 title claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims description 12
- 125000003545 alkoxy group Chemical group 0.000 title description 5
- -1 aromatic radicals Chemical class 0.000 claims description 71
- 239000002253 acid Substances 0.000 claims description 44
- 150000003254 radicals Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 24
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 24
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 16
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- FHLAEIKEWHOIOJ-UHFFFAOYSA-N 2,6-diaminonaphthalene-1,5-diol Chemical compound OC1=C(N)C=CC2=C(O)C(N)=CC=C21 FHLAEIKEWHOIOJ-UHFFFAOYSA-N 0.000 claims description 2
- BBECNDJSLQBLJL-UHFFFAOYSA-N 3-(3-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)C=2C=C(C=CC=2)C(O)=O)=C1 BBECNDJSLQBLJL-UHFFFAOYSA-N 0.000 claims description 2
- FJXIPWRKSXGKSY-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=CC=C(C(O)=O)C=C1 FJXIPWRKSXGKSY-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000012696 Interfacial polycondensation Methods 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
- LUKYIMOTPSTGQB-UHFFFAOYSA-N 2-amino-4-ethylphenol Chemical compound CCC1=CC=C(O)C(N)=C1 LUKYIMOTPSTGQB-UHFFFAOYSA-N 0.000 claims 1
- RBQRPOWGQURLEU-UHFFFAOYSA-N 3-[(3-carboxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2C=C(C=CC=2)C(O)=O)=C1 RBQRPOWGQURLEU-UHFFFAOYSA-N 0.000 claims 1
- DPYROBMRMXHROQ-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-diol Chemical compound NC1=CC(N)=C(O)C=C1O DPYROBMRMXHROQ-UHFFFAOYSA-N 0.000 claims 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 claims 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 claims 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 claims 1
- XKACUVXWRVMXOE-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)(C)C1=CC=C(C(O)=O)C=C1 XKACUVXWRVMXOE-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- JBBHFHMVEOHFRE-UHFFFAOYSA-N anthracene-2,6-diol Chemical compound C1=C(O)C=CC2=CC3=CC(O)=CC=C3C=C21 JBBHFHMVEOHFRE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 38
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 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 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- CMDHNEAPXOZXBI-UHFFFAOYSA-N n-[4-[4-(hydroxyamino)phenyl]phenyl]hydroxylamine Chemical compound C1=CC(NO)=CC=C1C1=CC=C(NO)C=C1 CMDHNEAPXOZXBI-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- 229920002577 polybenzoxazole Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- RUDCBGCNXOSCTI-UHFFFAOYSA-N n-methoxy-4-[4-(methoxyamino)phenyl]aniline Chemical compound C1=CC(NOC)=CC=C1C1=CC=C(NOC)C=C1 RUDCBGCNXOSCTI-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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-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
- 230000000704 physical effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SOHGRTUCDJZJLB-UHFFFAOYSA-N 1,5-diaminonaphthalene-2,6-diol Chemical compound OC1=CC=C2C(N)=C(O)C=CC2=C1N SOHGRTUCDJZJLB-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- WUQVDPFDUYAKSI-UHFFFAOYSA-N 2,5-diaminonaphthalene-1,6-diol Chemical compound NC1=C(O)C=CC2=C(O)C(N)=CC=C21 WUQVDPFDUYAKSI-UHFFFAOYSA-N 0.000 description 1
- AOTLXSIYOKZSAI-UHFFFAOYSA-N 2-[carboxy-(2-carboxyphenyl)methyl]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1C(C(=O)O)C1=CC=CC=C1C(O)=O AOTLXSIYOKZSAI-UHFFFAOYSA-N 0.000 description 1
- UTYHQSKRFPHMQQ-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenoxy)phenol Chemical compound C1=C(O)C(N)=CC(OC=2C=C(N)C(O)=CC=2)=C1 UTYHQSKRFPHMQQ-UHFFFAOYSA-N 0.000 description 1
- PZSYWQSQWUHYRT-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(O)C(N)=CC(SC=2C=C(N)C(O)=CC=2)=C1 PZSYWQSQWUHYRT-UHFFFAOYSA-N 0.000 description 1
- KCFVSHSJPIVGCG-UHFFFAOYSA-N 2-amino-4-[(3-amino-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(N)=CC(CC=2C=C(N)C(O)=CC=2)=C1 KCFVSHSJPIVGCG-UHFFFAOYSA-N 0.000 description 1
- QFQNRDDXHNGFNW-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)ethyl]phenol Chemical compound C1=C(O)C(N)=CC(CCC=2C=C(N)C(O)=CC=2)=C1 QFQNRDDXHNGFNW-UHFFFAOYSA-N 0.000 description 1
- KHAFBBNQUOEYHB-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(O)=C1 KHAFBBNQUOEYHB-UHFFFAOYSA-N 0.000 description 1
- JDFAWEKPFLGRAK-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(N)C(O)=CC=1C(C)(C)C1=CC=C(N)C(O)=C1 JDFAWEKPFLGRAK-UHFFFAOYSA-N 0.000 description 1
- JZGCFTMOWCCCNO-UHFFFAOYSA-N 3,4-diaminobenzene-1,2-diol Chemical compound NC1=CC=C(O)C(O)=C1N JZGCFTMOWCCCNO-UHFFFAOYSA-N 0.000 description 1
- ZFCNECLRCWFTLI-UHFFFAOYSA-N 3-(3-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(O)=O)=C1 ZFCNECLRCWFTLI-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- RDYSDCWZHHUGIB-UHFFFAOYSA-N 6,8-dihydroxy-3-methyl-2h-isoquinolin-1-one Chemical class OC1=CC(O)=C2C(=O)NC(C)=CC2=C1 RDYSDCWZHHUGIB-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-DRSKVUCWSA-N C1=C(C=CC2=CC(=CC=C12)[2H])[2H] Chemical compound C1=C(C=CC2=CC(=CC=C12)[2H])[2H] UFWIBTONFRDIAS-DRSKVUCWSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- AEWGGPYHSLODJJ-UHFFFAOYSA-N bis(3-amino-4-hydroxyphenyl)methanone Chemical compound C1=C(O)C(N)=CC(C(=O)C=2C=C(N)C(O)=CC=2)=C1 AEWGGPYHSLODJJ-UHFFFAOYSA-N 0.000 description 1
- QLRMWXKBIDRYEQ-UHFFFAOYSA-N bis(4-amino-3-hydroxyphenyl)methanone Chemical compound C1=C(O)C(N)=CC=C1C(=O)C1=CC=C(N)C(O)=C1 QLRMWXKBIDRYEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR109040 | 1967-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770569A1 true DE1770569A1 (de) | 1971-10-28 |
Family
ID=8632275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770569 Pending DE1770569A1 (de) | 1967-06-05 | 1968-06-05 | Alkoxy- und Hydroxypolyamide |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3644286A (enExample) |
| CH (1) | CH499566A (enExample) |
| DE (1) | DE1770569A1 (enExample) |
| FR (1) | FR1548307A (enExample) |
| GB (1) | GB1235357A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061856A (en) * | 1974-10-10 | 1977-12-06 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Trimerization of aromatic nitriles |
| US5124432A (en) * | 1989-08-31 | 1992-06-23 | The Dow Chemical Company | Branched polybenzazole polymer and method of preparation |
| DE10126572B4 (de) | 2001-05-31 | 2006-10-26 | Infineon Technologies Ag | Polyhydroxyamide und daraus erhältliche hochvernetzte chemisch und thermisch stabile Polymere |
-
1967
- 1967-06-05 FR FR109040A patent/FR1548307A/fr not_active Expired
-
1968
- 1968-05-28 CH CH784468A patent/CH499566A/fr not_active IP Right Cessation
- 1968-06-05 US US784959*A patent/US3644286A/en not_active Expired - Lifetime
- 1968-06-05 GB GB26828/68A patent/GB1235357A/en not_active Expired
- 1968-06-05 DE DE19681770569 patent/DE1770569A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3644286A (en) | 1972-02-22 |
| FR1548307A (enExample) | 1968-12-06 |
| CH499566A (fr) | 1970-11-30 |
| GB1235357A (en) | 1971-06-16 |
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