EP2294113A2 - Verfahren zur herstellung eines polyamidimids, polyamidimid und dieses polyamidimid umfassende zusammensetzung - Google Patents
Verfahren zur herstellung eines polyamidimids, polyamidimid und dieses polyamidimid umfassende zusammensetzungInfo
- Publication number
- EP2294113A2 EP2294113A2 EP09765750A EP09765750A EP2294113A2 EP 2294113 A2 EP2294113 A2 EP 2294113A2 EP 09765750 A EP09765750 A EP 09765750A EP 09765750 A EP09765750 A EP 09765750A EP 2294113 A2 EP2294113 A2 EP 2294113A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- polyamideimide
- aromatic
- aliphatic
- 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.)
- Withdrawn
Links
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 75
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 diamine compound Chemical class 0.000 claims abstract description 31
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 16
- 239000011159 matrix material Substances 0.000 claims abstract description 11
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 10
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 150000004985 diamines Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 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 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 150000008064 anhydrides Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 7
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 5
- 238000007493 shaping process Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 238000001746 injection moulding Methods 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000007664 blowing Methods 0.000 claims 2
- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 238000009987 spinning Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 50
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229920002302 Nylon 6,6 Polymers 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- 150000003949 imides Chemical group 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000004953 Aliphatic polyamide Substances 0.000 description 5
- 229920003231 aliphatic polyamide Polymers 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- BUGIFNPYQVKODR-UHFFFAOYSA-N 2-methylhexane-1,6-diamine Chemical compound NCC(C)CCCCN BUGIFNPYQVKODR-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 229920001944 Plastisol Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000010101 extrusion blow moulding Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-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
- 239000012071 phase Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004999 plastisol Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- QABJRPWOBYCMBO-UHFFFAOYSA-N 1,4-dioxacyclotridecane-5,13-dione Chemical compound O=C1CCCCCCCC(=O)OCCO1 QABJRPWOBYCMBO-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- FDLFMPKQBNPIER-UHFFFAOYSA-N 1-methyl-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(C)C=CC=2)=C1 FDLFMPKQBNPIER-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
- NRMSFXMULXCZAZ-UHFFFAOYSA-N 10-(3-azabicyclo[3.2.2]nona-1(7),5,8-trien-3-yl)-10-oxodecanamide Chemical compound C1N(C(=O)CCCCCCCCC(=O)N)CC2=CC=C1C=C2 NRMSFXMULXCZAZ-UHFFFAOYSA-N 0.000 description 1
- IHEOXPWZFCUHOQ-UHFFFAOYSA-N 2,3-dimethyl-1,4-dioxocane-5,8-dione Chemical compound CC1OC(=O)CCC(=O)OC1C IHEOXPWZFCUHOQ-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
- GDYYIJNDPMFMTB-UHFFFAOYSA-N 2-[3-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(CC(O)=O)=C1 GDYYIJNDPMFMTB-UHFFFAOYSA-N 0.000 description 1
- HASUJDLTAYUWCO-UHFFFAOYSA-N 2-aminoundecanoic acid Chemical compound CCCCCCCCCC(N)C(O)=O HASUJDLTAYUWCO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- DJIHQRBJGCGSIR-UHFFFAOYSA-N 2-methylidene-1,3-dioxepane-4,7-dione Chemical compound C1(CCC(=O)OC(=C)O1)=O DJIHQRBJGCGSIR-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 description 1
- LBCHYKTUUMRFHG-UHFFFAOYSA-N 3,5-diphenyl-7-oxabicyclo[2.2.1]hepta-1(6),2,4-triene Chemical compound C=1C(C=2C=CC=CC=2)=C2OC=1C=C2C1=CC=CC=C1 LBCHYKTUUMRFHG-UHFFFAOYSA-N 0.000 description 1
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- IZXROJODNWLEHG-UHFFFAOYSA-N 4,4-bis(aminomethyl)cyclohexane-1,1-diamine Chemical class NCC1(CCC(CC1)(N)N)CN IZXROJODNWLEHG-UHFFFAOYSA-N 0.000 description 1
- PGGROMGHWHXWJL-UHFFFAOYSA-N 4-(azepane-1-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1CCCCCC1 PGGROMGHWHXWJL-UHFFFAOYSA-N 0.000 description 1
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- DZCPFKFMCCYUOU-UHFFFAOYSA-N 5-methylnonane-1,1-diamine Chemical compound CCCCC(C)CCCC(N)N DZCPFKFMCCYUOU-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004956 Amodel Substances 0.000 description 1
- 101100255205 Caenorhabditis elegans rsa-2 gene Proteins 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 1
- MXZOWUXWWWEMJS-UHFFFAOYSA-N N=C=O.N=C=O.CC1(C)CC=CC=C1C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.CC1(C)CC=CC=C1C1=CC=CC=C1 MXZOWUXWWWEMJS-UHFFFAOYSA-N 0.000 description 1
- SPTUBPSDCZNVSI-UHFFFAOYSA-N N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC Chemical compound N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC SPTUBPSDCZNVSI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000616 Poly(1,4-butylene adipate) Polymers 0.000 description 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- LKAVYBZHOYOUSX-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;styrene Chemical compound C=CC=C.CC(=C)C(O)=O.C=CC1=CC=CC=C1 LKAVYBZHOYOUSX-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 229920002852 poly(2,6-dimethyl-1,4-phenylene oxide) polymer Polymers 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000414 polyfuran Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing 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
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Definitions
- R " is a hydrocarbon radical preferably comprising between 2 and 18 carbon atoms
- Y is a trivalent hydrocarbon radical, aromatic or aliphatic, preferably aromatic
- Y ' is a tetravalent, aromatic or aliphatic hydrocarbon radical, preferably aromatic
- the invention provides a thermoplastic polymer composition comprising the semi-aromatic polyamideimide of the invention described above or obtained by the method of the invention described above.
- the invention finally relates, in a fourth object, the articles obtained by shaping the composition of the invention.
- the process for the preparation of polyamideimide of the invention uses as monomer at least one compound a) organic, preferably aromatic.
- the compound a) has at least three functional groups selected from carboxyl groups and amino groups.
- the compound a) comprises three or four carboxyl groups, preferably three or four carboxylic acid functions.
- the compound a) may for example comprise at least one pair of carboxyl groups ortho position relative to each other.
- the compound a) is of formula (I) below:
- the compound a) is preferably chosen from trimellitic acid, pyromellitic acid, their anhydrides, their esters or their amides.
- the compound a) does not include an imide function.
- the compound a) may also be a compound having an amino group and two carboxyl groups.
- examples of such compounds include aspartic acid, 3-aminophthalic acid or 4-aminophthalic acid.
- mixtures of different compounds a) can be implemented.
- Suitable aromatic diamines in the present invention include diamines wherein R in the general formula is phenylene group, a condensed aromatic group, such as naphthylene group, or two (or more) linked aromatic rings, as shown by bisphenylene, bisphenylenemethane, bisphenylenepropane, bisphenylenesulfone, bisphenylene ether and the like.
- any of the aromatic groups may carry one or more substituents on the ring, such as lower alkyl groups or halogen atoms, which do not react under the polymerization conditions.
- the diamine preferably contains 2 to 18 carbon atoms, more preferably 4 to 12 carbon atoms.
- diamines include diamines of the homologous series H 2 N (CH 2 ) InNH 2 in which m is an integer of 2 to 12, preferably 4 to 8, and diamines of the general formula H 2 N ( CH 2 ) p Z (CH 2 ) qNH 2 wherein Z is phenylene and p and q are independently 1, 2 or 3.
- the compound b) is an aliphatic diamine.
- the diamines may for example be chosen from hexamethylenediamine; butane diamine; 2-methyl pentamethylene diamine; 2-methyl hexamethylenediamine; 3-methyl hexamethylene diamine; 2,5-dimethyl hexamethylenediamine; 2,2-dimethylpentamethylene diamine; nonane diamine; 5-methylnonanediamine; dodecamethylene diamine; 2,2,4- and 2,4,4-trimethyl hexamethylenediamine; 2,2,7,7-tetramethyl octamethylene diamine; meta-xylylenediamine; paraxylylene diamine; isophorone diamine; diaminodicyclohexyl methane and C2-C16 aliphatic diamines which may be substituted by one or more alkyl groups.
- the preferred diamine is hexamethylenediamine. Mixtures of diamines can also be used in the present invention to produce polymers having recurring units wherein the group represented by R in the
- At least 45 mol%, preferably at least 50 mol% of the diamine compound is an aliphatic, cycloaliphatic or arylaliphatic diamine.
- the compound c) has the following formula (III):
- the radical R ' preferably has between 2 and 18 carbon atoms.
- arylaliphatic diacid means a diacid which at least one of the acid functions is not attached to a carbon atom forming part of an aromatic ring.
- the compound c) is an aliphatic diacid.
- the aliphatic acid may for example be chosen from oxalic, maleic, succinic, pimelic and azelaic acid. It may also include unsaturations, this is the case, for example, of maleic or fumaric acid.
- the dicarboxylic acids may also be chosen from glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedioic acid; 1,2-or 1,3-cyclohexane dicarboxylic acid; 1,2-or 1,3-phenylene diacetic acid; 1, 2-or 1,3-cyclohexane diacetic acid; isophthalic acid; terephthalic acid; 4,4'-benzophenone acid dicarboxylic acid; 2,5-naphthalene dicarboxylic acid; and pt-butyl isophthalic acid.
- the preferred dicarboxylic acid is adipic acid.
- mixtures of different compounds c) can be implemented.
- the process of the invention does not comprise lactam monomers or aliphatic amino acids, preferably no lactams or amino acids, such as caprolactam, 6-aminohexanoic acid, 5-aminopentanoic acid, the acid. 7-aminoheptanoic acid, aminoundecanoic acid, dodecanolactam.
- the method of the invention does not comprise diol monomers. Indeed the presence of such monomers may for example result in low viscosity of the polymers obtained, which is not desirable.
- the process for preparing the polyamideimide of the invention comprises a melt polymerization of the monomers a), b) and optionally c).
- melt polymerization is meant that the polymerization is carried out in the liquid state, and that the polymerization medium contains no solvent other than water, optionally.
- the polymerization is carried out in a continuous liquid phase.
- the polymerization medium may for example be an aqueous solution comprising the monomers, or a liquid comprising the monomers.
- the polymerization medium comprises water as a solvent. This facilitates the agitation of the medium, and therefore its homogeneity.
- the polymerization medium may also include additives such as chain limiters.
- the polyamideimide of the invention is generally obtained by polycondensation between the compound a), the compound b) and optionally the compound c) to form polyamideimide chains, with formation of the elimination product, in particular water, some of which can vaporize.
- the polyamideimide of the invention is generally obtained by heating at high temperature and pressure, for example an aqueous solution comprising the monomers, or a liquid comprising the monomers, to evaporate the elimination product, in particularly water (initially present in the polymerization medium and / or formed during the polycondensation) while avoiding any solid phase formation to prevent caking.
- the polycondensation reaction is generally carried out at a pressure of approximately 0.5-2.5 MPa (0.5-3.5 MPa) at a temperature of approximately 215-300 ° C. (180-320 ° C.). VS).
- the polycondensation is generally continued in the melt phase at atmospheric pressure or reduced so as to reach the desired degree of advancement.
- the polycondensation product is a polymer or molten prepolymer. It may comprise a vapor phase consisting essentially of vapor of the elimination product, in particular water, which may have been formed and / or vaporized.
- This product can be subjected to vapor phase separation and finishing steps to achieve the desired degree of polycondensation.
- the separation of the vapor phase may for example be carried out in a cyclone device. Such devices are known.
- the finish consists in maintaining the polycondensation product in the molten state, under a pressure close to atmospheric pressure or under reduced pressure, for a time sufficient to reach the desired degree of advancement. Such an operation is known to those skilled in the art.
- the temperature of the finishing step is advantageously greater than or equal to 200 ° C. and in all cases greater than the solidification temperature of the polymer.
- the residence time in the finishing device is preferably greater than or equal to 5 minutes.
- the polycondensation product may also undergo a post-condensation phase in solid phase. This step is known to the man of and increases the degree of polycondensation to a desired value.
- the process of the invention is similar in its conditions to the conventional polyamide preparation process of the type of those obtained from dicarboxylic acids and diamines, in particular the process for producing polyamide 66 from acid. adipic and hexamethylene diamine.
- This method of manufacturing polyamide 66 is known to those skilled in the art.
- the process for producing polyamide of the type of those obtained from dicarboxylic acids and diamines generally uses as raw material, a salt obtained by a mixture in stoichiometric quantity, generally in a solvent such as water, a diacid with a diamine.
- adipic acid is mixed with hexamethylene diamine generally in water to obtain hexamethylene diammonium adipate better known as nylon salt or " Salt N ".
- the process of the invention generally leads to a random polymer.
- the process of the invention is a simple process and easy to implement, which does not implement organic solvents that can be toxic.
- the polyamideimide obtained according to the process of the invention can be used directly, without additional step for example to recover the polymer, as is the case for example in solution preparation processes.
- the polyamideimide obtained at the end of the finishing step can be cooled and put into the form of granules.
- the polyamideimide obtained by the process of the invention in molten form can be directly shaped or extruded and granulated, for subsequent shaping after melting.
- R and R ' are aliphatic, cycloaliphatic or arylaliphatic hydrocarbon radicals, advantageously aliphatic or cycloaliphatic, preferably comprising between 2 and 18 carbon atoms
- Y is a trivalent aromatic hydrocarbon radical
- Y ' is a tetravalent aromatic hydrocarbon radical
- R '" is an aromatic hydrocarbon radical, preferably comprising between 2 and 18 carbon atoms
- Y ' is a tetravalent, aromatic or aliphatic hydrocarbon radical, preferably aromatic
- the polyamideimide advantageously comprises at least 60 mol%, preferably at least 80 mol% of recurring units A.
- the polyamideimides of the invention have the advantage of being easily converted into the molten route, such as aliphatic polyamides, for example, which facilitates their shaping.
- aliphatic polyamides for example, which facilitates their shaping.
- thermomechanical properties in particular the HDT property "Heat Distortion Temperature”
- they show better water absorption properties compared to aliphatic polyamides, and a reduced thermal expansion compared with aliphatic polyamides.
- the polyamideimide of the invention may be used alone or as part of a composition. It can particularly be used as an additive in thermoplastic polymer compositions comprising a thermoplastic matrix. He is involved in the composition as a reinforcing agent.
- the thermoplastic matrix is a thermoplastic polymer.
- polymers which may be suitable, mention may be made of: polylactones such as poly (pivalolactone), poly (caprolactone) and polymers of the same family; polyurethanes obtained by reaction between diisocyanates such as 1,5-naphthalene diisocyanate; p-phenylene diisocyanate, m-phenylene diisocyanate, 2,4-toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate, 3, 3-dimethyl-4,4'-biphenyl diisocyanate, 4,4'-diphenylisopropylidene diisocyanate, 3,3'-dimethyl-4,4'-diphenyl diisocyanate, 3,3'-dimethyl-4,4 ' diphenylmethane diisocyanate, 3,3'-dimethoxy-4
- the thermoplastic matrix is a polymer comprising star or H macromolecular chains, and optionally linear macromolecular chains.
- the polymers comprising such star or H macromolecular chains are for example described in the documents FR 2 743 077, FR 2 779 730, US 5 959 069, EP 0 632 703, EP 0 682 057 and EP 0 832 149.
- thermoplastic matrix of the invention is a random tree type polymer, preferably a copolyamide having a random tree structure.
- a copolyamide having a random tree structure are described in particular in WO 99/03909.
- thermoplastic matrix of the invention may also be a composition comprising a linear thermoplastic polymer and a thermoplastic star, H and / or tree polymer as described above.
- compositions of the invention may also comprise a hyperbranched copolyamide of the type of those described in WO 00/68298.
- thermostable polymers these polymers are preferably infusible or have a softening point greater than 180 ° C., preferably> 200 0 C, or higher.
- thermostable polymers may for example be chosen from aromatic polyamides, polyamide imides such as polytrimellamide imides, or polyimides such as the polyimides obtained according to document EP 0119185, known commercially under the trademark P84.
- aromatic polyamides may be as described in patent EP 0360707. They may be obtained according to the process described in patent EP 0360707.
- polymeric matrix there may also be mentioned viscose, cellulose, cellulose acetate and so on.
- the polymer matrix of the invention may also be of the type of polymers used in adhesives, such as copolymers of plastisol vinyl acetates, acrylic latices, urethane latices, PVC plastisol, etc.
- semicrystalline polyamides such as polyamide 6, polyamide 6.6, polyamide 11, polyamide 12, polyamide 4, polyamides 4-6, 6-10, are particularly preferred.
- 6-12, 6-36, 12-12, semi-aromatic polyamides obtained from terephthalic and / or isophthalic acid such as the polyamide marketed under the trade name AMODEL; polyesters such as PET, PBT, PTT; polyolefins such as polypropylene, polyethylene; aromatic polyamides, polyamide imides or polyimides; latex such as acrylic latex and urethane; PVC, viscose, cellulose, cellulose acetate; their copolymers and alloys.
- compositions may contain any other additives that may be used, for example reinforcing fillers, flame retardants, UV stabilizers, heat, mattifying agents such as titanium dioxide.
- compositions according to the invention can be used as raw material in the field of engineering plastics, for example for the production of injection molded articles or by injection / blow molding, extruded by conventional extrusion or by extrusion blow molding, or movies.
- compositions according to the invention can also be put into the form of son, fibers, filaments by melt-spinning.
- Absolute molar mass determined by gel permeation chromatography (GPC) in dichloromethane (+ trifluoroacetic anhydride), then by triple detection by refractometry R1, UV absorption and viscosimethe.
- Imide cyclization rate determined by 1 H NMR at 300 K in deuterated formic acid, using a 300 MHz Bruker DRX apparatus
- T f Melting temperature and associated enthalpy ( ⁇ Hf), glass transition temperature (T 9 ), cooling crystallization temperature (T c ): determined by differential scanning calorimetry (DSC) using a Perkin Elmer Pyris 1 device, at a rate of 10 ° C / min.
- Viscosity index (IV) measured according to ISO EN 307 Example 1 Preparation of a Polyamide Imide PAI 66 / 6TMA 90/10
- the polyamideimide is manufactured according to a standard polyamide 66 polymerization process.
- Tg 63 ° C.
- Tc 204.2 ° C.
- mp 247.2 ° C.
- Examples 2 to 7 are prepared, according to a standard method of polymerization of polyamide 66 type, as in Example 1, polyamideimides of PAI 66 / 6TMA type of molar composition 80/20 (Example 2), 67/33 ( Example 3), 60/40 (Example 4), 50/50 (Example 5), 30/70 (Example 6),
- trimellitic anhydride is used in place of trimellitic acid.
- the polyamideimide is manufactured according to a standard polyamide 66 polymerization process, as in Example 1.
- the polymer obtained is cast in the form of rod, cooled and granulated by cutting rushes.
- the polymer obtained is cast in the form of rod, cooled and granulated by cutting rushes.
- the polyamideimide used is polyamidimide of Example 9.
- N.M. No Measurable: existence of a Ta but it can not be measured.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0803263A FR2932486B1 (fr) | 2008-06-12 | 2008-06-12 | Procede de preparation d'un polyamideimide, polyamideimide et composition comprenant ce polyamideimide. |
| PCT/EP2009/056915 WO2009153170A2 (fr) | 2008-06-12 | 2009-06-05 | Procede de preparation d'un polyamideimide, polyamideimide et composition comprenant ce polyamideimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2294113A2 true EP2294113A2 (de) | 2011-03-16 |
Family
ID=40043051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP09765750A Withdrawn EP2294113A2 (de) | 2008-06-12 | 2009-06-05 | Verfahren zur herstellung eines polyamidimids, polyamidimid und dieses polyamidimid umfassende zusammensetzung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20110160407A1 (de) |
| EP (1) | EP2294113A2 (de) |
| KR (1) | KR101308319B1 (de) |
| CN (1) | CN102099398B (de) |
| BR (1) | BRPI0909912A2 (de) |
| FR (1) | FR2932486B1 (de) |
| WO (1) | WO2009153170A2 (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102585223B (zh) * | 2011-12-29 | 2013-08-28 | 东莞市信诺橡塑工业有限公司 | 一种长碳链半芳香族聚酰胺酰亚胺及其合成方法 |
| CN102532545B (zh) * | 2011-12-29 | 2013-11-06 | 东莞市信诺橡塑工业有限公司 | 一种长碳链半芳香族聚酰胺酰亚胺及其合成方法 |
| CN102702526B (zh) * | 2012-06-21 | 2014-04-02 | 东莞市信诺橡塑工业有限公司 | 松香基半脂环族聚酰胺酰亚胺共聚物及其合成方法 |
| EP2708569B1 (de) * | 2012-09-12 | 2018-05-23 | Ems-Patent Ag | Transparente polyamidimide |
| JP6913346B2 (ja) * | 2016-04-05 | 2021-08-04 | ユニチカ株式会社 | ポリアミドイミド前駆体溶液 |
| KR102717867B1 (ko) | 2018-11-08 | 2024-10-15 | 삼성전자주식회사 | 폴리(아미드-이미드) 코폴리머, 폴리(아미드-이미드) 코폴리머 제조용 조성물, 폴리(아미드-이미드) 코폴리머를 포함하는 성형품 및 표시 장치 |
| CN110437445B (zh) * | 2019-08-21 | 2021-11-16 | 中仑塑业(福建)有限公司 | 一种聚酰胺树脂及其制备方法和用途 |
| EP4028449B1 (de) * | 2019-09-09 | 2024-05-15 | Solvay Specialty Polymers USA, LLC | Verfahren zur herstellung von polyamidimidpolymer |
| WO2021048075A1 (en) | 2019-09-09 | 2021-03-18 | Solvay Specialty Polymers Usa, Llc | Polyamide-imide polymer and process for its manufacture |
| CN110734545A (zh) * | 2019-10-28 | 2020-01-31 | 中仑塑业(福建)有限公司 | 一种聚酰亚胺树脂及其制备方法和用途 |
| CN112321829B (zh) * | 2020-10-29 | 2023-01-06 | 山东君昊高性能聚合物有限公司 | 水相合成聚酰胺-酰亚胺树脂的方法 |
| CN114716678A (zh) * | 2020-12-22 | 2022-07-08 | 成都肆零壹科技有限公司 | 一种酰亚胺结构聚合物的制备方法 |
| JP7772806B2 (ja) * | 2021-09-06 | 2025-11-18 | 三井化学株式会社 | 半導体用の膜を形成するための組成物、積層体及び基板積層体 |
| CN116891687A (zh) * | 2023-07-10 | 2023-10-17 | 广东鑫华新材料科技有限公司 | 一种太阳能光伏打孔胶带组合物及其制备方法 |
| CN119570030A (zh) * | 2024-11-14 | 2025-03-07 | 东华大学 | 一种基于生物基脂肪胺的高性能耐磨液晶聚酰胺-酰亚胺树脂及其制备和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58162637A (ja) * | 1982-03-19 | 1983-09-27 | Nitto Electric Ind Co Ltd | ポリアミドイミド樹脂の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756218A (fr) * | 1969-09-16 | 1971-03-01 | Bayer Ag | Procede de production d'acides imidocarboxyliques |
| US3961009A (en) * | 1970-04-22 | 1976-06-01 | Toray Industries, Inc. | Process for the production of a shaped article of a heat resistant polymer |
| US4070524A (en) * | 1976-02-23 | 1978-01-24 | Standard Oil Company (Indiana) | Self-bonding varnish for magnetic wire comprising polyalkylenetrimellitate imide polyalkylenetrimellitate ester |
| US4831108A (en) * | 1983-02-16 | 1989-05-16 | Amoco Corporation | Polycondensation process with mean dispersion residence time |
| US5395870A (en) * | 1988-12-28 | 1995-03-07 | Asahi Kasei Kogyo Kabushiki Kaisha | Vinyl resin composition |
| DE4025346A1 (de) * | 1990-08-10 | 1992-02-13 | Bayer Ag | Transparente, thermoplastische polyetheresteramidimid-elastomere sowie ihre verwendung zur herstellung von medizinischen gebrauchsartikeln |
-
2008
- 2008-06-12 FR FR0803263A patent/FR2932486B1/fr not_active Expired - Fee Related
-
2009
- 2009-06-05 US US12/997,208 patent/US20110160407A1/en not_active Abandoned
- 2009-06-05 CN CN2009801282568A patent/CN102099398B/zh not_active Expired - Fee Related
- 2009-06-05 EP EP09765750A patent/EP2294113A2/de not_active Withdrawn
- 2009-06-05 KR KR1020107027871A patent/KR101308319B1/ko not_active Expired - Fee Related
- 2009-06-05 WO PCT/EP2009/056915 patent/WO2009153170A2/fr not_active Ceased
- 2009-06-05 BR BRPI0909912A patent/BRPI0909912A2/pt not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58162637A (ja) * | 1982-03-19 | 1983-09-27 | Nitto Electric Ind Co Ltd | ポリアミドイミド樹脂の製造方法 |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO2009153170A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102099398A (zh) | 2011-06-15 |
| CN102099398B (zh) | 2013-11-20 |
| FR2932486B1 (fr) | 2012-12-07 |
| WO2009153170A3 (fr) | 2010-02-18 |
| US20110160407A1 (en) | 2011-06-30 |
| FR2932486A1 (fr) | 2009-12-18 |
| WO2009153170A2 (fr) | 2009-12-23 |
| KR20110013472A (ko) | 2011-02-09 |
| BRPI0909912A2 (pt) | 2015-10-20 |
| KR101308319B1 (ko) | 2013-09-17 |
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