KR20080040640A - 포스포네이트의 존재 하에서 폴리아미드의 제조방법 - Google Patents
포스포네이트의 존재 하에서 폴리아미드의 제조방법 Download PDFInfo
- Publication number
- KR20080040640A KR20080040640A KR1020077030340A KR20077030340A KR20080040640A KR 20080040640 A KR20080040640 A KR 20080040640A KR 1020077030340 A KR1020077030340 A KR 1020077030340A KR 20077030340 A KR20077030340 A KR 20077030340A KR 20080040640 A KR20080040640 A KR 20080040640A
- Authority
- KR
- South Korea
- Prior art keywords
- tert
- alkyl
- butyl
- bis
- cyclohexyl
- Prior art date
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 45
- 229920002647 polyamide Polymers 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 28
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000004985 diamines Chemical class 0.000 claims description 11
- 150000003951 lactams Chemical class 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 9
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 125000001624 naphthyl group Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 229920002292 Nylon 6 Polymers 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- 229920000299 Nylon 12 Polymers 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical group NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- 229920000571 Nylon 11 Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- QFNNDGVVMCZKEY-UHFFFAOYSA-N azacyclododecan-2-one Chemical compound O=C1CCCCCCCCCCN1 QFNNDGVVMCZKEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical class 0.000 claims description 2
- OWEZJUPKTBEISC-UHFFFAOYSA-N decane-1,1-diamine Chemical compound CCCCCCCCCC(N)N OWEZJUPKTBEISC-UHFFFAOYSA-N 0.000 claims description 2
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 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
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- -1 PA 69 Polymers 0.000 description 88
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920002302 Nylon 6,6 Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 150000002815 nickel Chemical class 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 229940113165 trimethylolpropane Drugs 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical compound S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UCJDCGANFAKTKA-UHFFFAOYSA-N 2,4-dimethyl-1,3,5-triazine Chemical compound CC1=NC=NC(C)=N1 UCJDCGANFAKTKA-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 2
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 2
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 description 2
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
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- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
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- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
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- 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 1
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- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
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- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
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- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
- C08G69/30—Solid state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
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Abstract
본 발명은 다중축합반응 또는 다중부가반응(polyaddition) 공정의 초기에 첨가되는 포스포네이트의 존재 하에서 폴리아미드를 제조하는 방법에 관한 것이다. 그 결과 얻어진 예비중합체는 고분자량을 나타내고 거의 무색이다. 본 발명의 또 다른 요지는 중축합반응 과정에서 폴리아미드의 변성과 분자량을 증가시키기 위한 포스포네이트의 사용에 관한 것이다.
포스포네이트, 폴리아미드
Description
본 발명은 다중축합반응 또는 다중부가반응(polyaddition) 공정의 초기에 첨가되는 포스포네이트의 존재 하에서 폴리아미드를 제조하는 방법에 관한 것이다. 그 결과 얻어진 예비중합체는 고분자량을 나타내고 거의 무색이다. 본 발명의 또 다른 요지는 중축합반응 또는 다중부가반응 과정에서 폴리아미드의 변성과 분자량을 증가시키기 위한 포스포네이트의 사용에 관한 것이다.
중축합물, 특히 폴리아미드는 직물, 건축물, 전기 전자 부품, 가정 용품, 포장물 등에 플라스틱 물품으로서 널리 사용된다.
폴리아미드는 일반적으로 이를 테면 2 방법에 의해 형성된다. 제1 방법은 중간체로서 소위 "나일론 염"을 통해 디아민류와 이산류의 사이에 축합반응이다. "나일론 형태"의 첫번째 수는 디아민에서 탄소 원자의 수와 관련이 있고, 두번째 수는 각 이산(예, 나일론 6.12 또는 나일론 6.6)과 관련이 있다. 제2 공정은 산 기들과 락탐으로 알려진 아민 모두를 함유하는 단량체의 개환반응을 포함한다. 폴리아미드의 정체성은 락탐 단량체(예, 나일론 6 또는 나일론 12 등)에서 원자의 수를 기본으로 하고 있다. 기계적 및 물리적 성질은 주로 중합체의 분자량에 따라 달라진다. 중축합물은 일반적으로 용융물 내에 있는 예비중합체의 추가 축합반응에 의해 제조된다. 이와 같이 해서 고 분자량이 얻어질 수 있다. 어떤 이용 분야에 있어서, 예를 들면, 음료 팩 및 기능성 섬유에서는, 심지어 더 높은 분자량이 필요하다. 이들은 고체 상태 중축합반응[s. Fakirov, Kunststoffe, 74 (1984), 218 and R.E. Grutzner, A. Koine, Kunststoffe, 82 (1992), 284]에 의해 얻어질 수 있다. 중합체는 불활성 가스나 진공 하에 유리전이온도 이상 및 중합체의 용융 온도 이하에서 열처리된다. 그러나, 이 방법은 시간적 및 에너지 낭비적이다. 고유점도를 높이려면 진공 또는 불활성 가스 하에 180℃∼240℃에서 12 시간 이하의 체류시간을 요한다.
대부분의 폴리아미드는 반-결정질로 되는 경향이 있고, 일반적으로 내열성 및 내화학성이 좋은 매우 단단한 물질이다. 이와 같이 다양한 형태로 인해 비중, 융점 및 수분 흡수에 있어 광범위한 특성을 갖는다.
본 발명의 목적은 예비 중합 단계에서 폴리아미드의 분자량을 증가시키는 데 있다. "예비중합 단계"란 단량체로부터 출발하여 제1 중축합반응 또는 다중부가반응 단계에서 얻어지는 중합체를 의미한다.
놀랍게도, 포스포네이트의 존재 하에서 폴리아미드를 합성하면 예비중합체의 색상을 개선시키고 분자량 증가를 촉진한다는 것이 밝혀졌다. 상기 색상 개선은, 이를테면 WO 96/11978에 기재된 바와 같이, 용융 중축합반응 또는 고체 상태 중축합반응(SSP) 동안 첨가하는 경우에 비해 포스포네이트가 중축합반응이나 다중부가반응 공정 초기에 첨가되는 경우에 훨씬 더 높다.
본 발명의 일 요지는 이산 및 디아민 단량체로부터 또는 락탐 단량체로부터 출발하고 포스포네이트의 존재 하에서 중축합반응 또는 다중부가반응을 실시하는 것을 포함하는 폴리아미드 예비중합체의 제조방법에 있다.
폴리아미드, 즉 본래의 폴리아미드 및 폴리아미드 재활용물 모두는, 예를 들면, 디아민 및 디카르복시산 및/또는 아미노카르복시산 또는 상응하는 락탐으로부터 유도되는 지방족 및 방향족 폴리아미드 또는 코폴리아미드이다. 적당한 폴리아미드는, 예를 들면 PA 6, PA 11, PA 12, PA 46, PA 66, PA 69, PA 610, PA 612, PA 10.12, PA 12.12 및 무정형 폴리아미드 및 열가소성 폴리아미드 탄성중합체, 이를테면 "Vestamid, Grilamid ELY60, Pebax, Nyim and Grilon ELX" 형태의 폴리에테르 아미드이다. 이러한 형태의 폴리아미드는 공지되어 있고 시중에서 구입할 수 있다.
EP-A-0 613 919에서는 이를 테면 통상적인 폴리에테르 에스테르 아미드의 제조 및 용도에 대해서 기재하고 있다.
바람직하게 사용되는 폴리아미드는 결정질 또는 부분 결정질 폴리아미드, 특히 PA6 및 PA6.6 또는 이들의 블렌드이다.
폴리아미드 및 코폴리아미드는 디아민과 디카르복시산으로부터 및/또는 아미노카르복시산 또는 상응하는 락탐류, 이를테면 폴리아미드 4, 폴리아미드 6, 폴리아미드 6,6, 6,10, 6,9, 6,12, 4,6, 12,12, 폴리아미드 11, 폴리아미드 12, m-크실일렌, 디아민 및 아디프산으로부터 유도된 방향족 폴리아미드; 헥사메틸렌 디아민 및 이소- 및/또는 테레프탈산으로부터 제조된 폴리아미드 및 임의로는 조절제로서 탄성중합체, 예를 들면 폴리-2,4,4-트리메틸헥사메틸렌 테레프탈아미드 또는 폴리-m-페닐렌-이소프탈아미드로부터 유도된다.
예를 들면, 단량체는 테트라메틸렌디아민, 헥사메틸렌디아민, 디아미노데칸, 디아미노도데칸, 아디프산, 아젤라산, 세바스산, 도데칸디오산, ε-카프로락탐, 운데칸락탐, 라우로락탐 및 이들의 혼합물로 이루어진 군으로부터 선택된다.
바람직하게는, 단량체는 헥사메틸렌디아민 및 아디프산을 포함한다.
예를 들면, 폴리아미드 예비중합체는 폴리아미드 PA 4.6, PA 6.6; PA 6.9; PA 6.10, PA 6.12, PA 10.12, PA 12.12, PA 6, PA 11, PA 12 또는 PA 6/66 블렌드이다.
예를 들면, 포스포네이트는 하기 화학식(I)을 갖는 것이 바람직하다:
상기 식에서,
R3은 H, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸이고,
R4는 수소, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸; 또는
Mr + / r이고,
Mr +은 r-가 금속 양이온 또는 암모늄 이온이고,
n은 0, 1, 2, 3, 4, 5 또는 6이고,
r은 1, 2, 3 또는 4이고;
Q는 수소, -X-C(O)-OR7, 또는 라디칼
R1은 이소프로필, tert-부틸, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,
R2는 수소, C1-C4알킬, 시클로헥실, 또는 1-3 C1-C4알킬기 알킬기에 의해 치환된 시클로헥실이고,
R5는 H, C1-C18알킬, OH, 할로겐 또는 C3-C7시클로알킬이고;
R6은 H, 메틸, 트리메틸실일, 벤질, 페닐, 술포닐 또는 C1-C18알킬이고;
R7은 H, C1-C10알킬 또는 C3-C7시클로알킬이고; 그리고
X는 페닐렌, C1-C4알킬기-치환 페닐렌 또는 시클로헥실렌이다.
기타 적당한 포스포네이트를 하기에 열거한다.
입체장애 히드록시페닐알킬포스폰산 에스테르류 또는 반-에스테르류, 이를테면 US-A-4 778 840에 공지된 것이 바람직하다.
특히 바람직한 화합물은 하기 화학식(Ia)의 화합물이다:
상기 식에서,
R1은 H, 이소프로필, tert-부틸, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,
R2는 수소, C1-C4알킬, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,
R3은 C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸이고,
R4는 수소, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸; 또는
Mr + / r이고,
Mr +은 r-가 금속 양이온이고,
n은 1, 2, 3, 4, 5 또는 6이고,
r은 1, 2, 3 또는 4이다.
할로겐은 플루오로, 클로로, 브로모 또는 요오도이다.
탄소 원자 18 이하를 갖는 알킬 치환체로서 적당한 것은 메틸, 에틸, 프로 필, 부틸, 펜틸, 헥실 및 옥틸과 같은 라디칼; 스테아릴 및 상응하는 측쇄 이성질체이며; C2-C4알킬 및 이소옥틸이 바람직하다.
바람직하게는 1∼3, 더욱 바람직하게는 1 또는 2의 알킬기를 함유하는 C1-C4알킬-치환 페닐 또는 나프틸의 예는 o-, m- 또는 p-메틸페닐, 2,3-디메틸페닐, 2,4-디메틸페닐, 2,5-디메틸페닐, 2,6-디메틸페닐, 3,4-디메틸페닐, 3,5-디메틸페닐, 2-메틸-6-에틸페닐, 4-tert-부틸페닐, 2-에틸페닐, 2,6-디에틸페닐, 1-메틸나프틸, 2-메틸나프틸, 4-메틸나프틸, 1,6-디메틸나프틸 또는 4-tert-부틸나프틸이다.
바람직하게는 1∼3, 더욱 바람직하게는 1 또는 2의 측쇄 또는 비측쇄 알킬기 라디칼을 함유하는 C1-C4알킬-치환 시클로헥실의 예는 시클로펜틸, 메틸시클로펜틸, 디메틸시클로펜틸, 시클로헥실, 메틸시클로헥실, 디메틸시클로헥실, 트리메틸시클로헥실 또는 tert-부틸시클로헥실이다.
1-, 2-, 3- 또는 4-가 금속 양이온은 바람직하게는 알칼리 금속, 알칼리 토금속, 중금속 또는 알루미늄 양이온, 예를 들면 Na+, K+, Mg++, Ca++, Ba++, Zn++, Al+++, 또는 Ti++++이고, Ca++이 특히 바람직하다.
바람직한 화학식(Ia)의 화합물은 R1 또는 R2로서 적어도 하나의 tert-부틸기를 함유하는 것들이다. 특히 바람직한 화합물은, R1 및 R2가 동시에 tert-부틸인 것들이다.
n은 바람직하게는 1 또는 2, 특히 바람직하게는 1이다.
특히 바람직한 입체장애 아릴알킬포스폰산 에스테르류 또는 반-에스테르류는 하기 화학식(II), (III), (IV), (V) 및 (VI)의 화합물이다:
상기 식에서, R101 은 서로 독립적으로 수소, 에틸, 페닐 또는 Mr +/r이다. Mr +/r의 의미는 상술한 바와 같다.
화합물(II), (III), (IV), (V) 및 (VI) 중 일부는 시중에서 구입할 수 있거나 또는 표준 공정에 의해 제조될 수 있다.
예를 들면, 단량체 또는 단량체류 당 포스포네이트 10∼20 000 ppm, 바람직하게는 1000∼10 000 ppm, 특히 바람직하게는 200∼2000 ppm이 사용된다(ppm은 100만당 부, 중량이다).
바람직하게는, 포스포네이트는 단량체에 직접 첨가된 다음, 반응이 개시된 다. 어떤 경우에는 후에 첨가할 수도 있다.
바람직하게는, 중축합반응 또는 다중부가반응 온도는 150℃∼280℃, 특히 200℃∼250℃이다.
통상적으로 반응은 가압하에 실시된다. 바람직하게는 중축합반응 또는 다중부가반응 동안 압력은 3∼20 바아, 특히 5∼15 바아이다.
반응은 통상 불활성 분위기 하에서 실시된다.
반응은 가압할 수 있는 적당한 용기에서 실시될 수 있다. 중축합반응은 당해 기술분야에서 널리 공지되어 있다.
폴리아미드 예비중합체는, 예를 들면 추가 용융 중축합반응 또는 고체 상태 중축합반응 (SSP) 단계처럼 추가로 가공될 수 있다.
본 발명의 특정 실시양태에서, 후속적인 고체 상태 중축합반응이 폴리아미드 예비중합체에 적용된다.
고체 상태 중축합반응은 통상 180℃∼240℃에서 실시된다.
상술한 바와 같이, 상술한 방법에 따라 제조된 폴리아미드 예비중합체는 무색이거나 오로지 회백색(off-white) 색상을 나타내고, 이를테면 용융 유속에 의해 측정할 때 공지된 폴리아미드에 비해 고분자량을 갖는다.
이들 가공 단계에서 추가 반응 첨가제를 첨가하여 소망의 성질을 얻을 수 있다. 그 첨가제의 예를 하기에 열거한다.
1. 에폭시드 화합물:
I) 분자 내에 2 이상의 카르복시기를 갖는 화합물과 에피클로로히드린 및/또 는 글리세롤 디클로로히드린 및/또는 β-메틸에피클로로히드린을 반응하여 얻어질 수 있는 폴리글리시딜 및 폴리(β-메틸글리시딜) 에스테르류. 반응은 염기 존재 하에서 용이하게 실시된다.
분자 내에 2 이상의 카르복시기를 갖는 화합물로서는, 지방족 폴리카르복시산을 사용할 수 있다. 이들 폴리카르복시산의 예로는 글루타르산, 아디프산, 피멜산, 수베르산, 아젤라산, 세바스산 및 이합체화 또는 삼합체화 리놀레산이 있다.
그러나, 시클로지방족 폴리카르복시산, 이를테면 테트라하이드로프탈산, 4-메틸테트라하이드로프탈산, 헥사하이드로프탈산 및 4-메틸헥사하이드로프탈산을 이용할 수도 있다.
또한, 프탈산, 이소프탈산, 트리멜리트산 및 피로멜리트산과 같은 방향족 폴리카르복시산이 사용될 수 있다.
또한, 예를 들면, 트리멜리트산과 폴리올류와 카르복시-말단 부생물, 이를테면 글리세롤 또는 2,2-비스(4-히드록시시클로헥실)프로판을 이용할 수도 있다.
II) 2 이상의 자유 알코올성 히드록시기 및/또는 페놀성 히드록시기를 갖는 화합물과 적절히 치환된 에피클로로히드린을 알칼리 조건 하 또는 산성 촉매의 존재 하에서 반응시킨 후 알칼리 처리하여 얻어질 수 있는 폴리글리시딜 또는 폴리(β-메틸글리시딜) 에테르.
이러한 형태의 에테르는 예를 들면, 비시클릭 알코올류, 이를테면 에틸렌 글리콜, 디에틸렌 글리콜 및 고급 폴리(옥시에틸렌) 글리콜류, 프로판-1,2-디올, 또는 폴리-(옥시프로필렌)글리콜류, 프로판-1,3-디올, 부틸-1,4-디올, 폴리(옥시테트 라메틸렌) 글리콜류, 펜탄-1,5-디올, 헥산-1,6-디올, 헥산-2,4,6-트리올, 글리세롤, 1,1,1-트리메틸올프로판, 비스트리메틸올프로판, 펜타에리트리톨, 소르비톨 및 폴리에피클로로히드린으로부터 유도된다.
그러나, 이들은 또한 예를 들면, 1,3- 또는 1,4-디히드록시시클로헥산, 비스(4-히드록시시클로헥실)메탄, 2,2-비스(4-히드록시시클로헥실)-프로판 또는 1,1-비스(히드록시메틸)-시클로헥스-3-엔과 같은 시클로지방족 알코올류로부터 유도되거나, 또는 이들은 방향족 핵, 이를테면 N,N-비스(2-히드록시에틸)아닐린 또는 p,p'-비스(2-히드록시에틸아미노)디페닐메탄을 갖는다.
에폭시드 화합물은 또한 단핵 페놀류, 이를테면 레조르시놀 또는 하이드로퀴논으로부터 유도될 수 있거나; 또는 이들은 다핵 페놀류, 이를테면 비스(4-히드록시페닐)메탄, 2,2-비스(4-히드록시페닐)프로판, 2,2-비스(3,5-디브로모-4-히드록시페닐)프로판, 4,4'-디히드록시디페닐 술폰, 또는 페놀 노볼락과 같이 산성 조건 하에서 얻어지는 포름알데히드와 페놀류와의 축합 생성물을 기본으로 한다.
III) 적어도 2개의 아미노 수소 원자를 함유하는 아민과 에피클로로히드린과의 반응 생성물의 탈염화수소(dehydrochlorination) 반응에 의해 얻어질 수 있는 폴리(N-글리시딜) 화합물. 이들 아민의 예로는 아닐린, 톨루이딘, n-부틸아민, 비스(4-아미노페닐)메탄, m-크실일렌디아민 및 비스(4-메틸아미노페닐)메탄, 및 N,N,O-트리글리시딜-m-아미노페놀 및 N,N,O-트리글리시딜-p-아미노페놀이 있다.
그러나, 폴리(N-글리시딜) 화합물은 또한 에틸렌 우레아 또는 1,3-프로필렌 우레아와 같은 시클로알킬렌 우레아의 N,N'-디글리시딜 유도체, 및 5,5-디메틸히단 토인과 같은 히단토인의 N,N'-디글리시딜 유도체를 포함한다.
IV) 폴리(S-글리시딜) 화합물, 이를테면 에탄-1,2-디티올 또는 비스(4-머캅토메틸페닐) 에테르와 같은 디티올로부터 유도된 디-S-글리시딜 유도체.
적당한 에폭시드의 예는 다음과 같다:
a) 액체 비스페놀 A 디글리시딜 에테르, 이를테면 Araldit®GY 240, Araldit®GY 250, Araldit®GY 260, Araldit®GY 266, Araldit®GY 2600, Araldit®MY 790;
b) 고체 비스페놀 A 디글리시딜 에테르, 이를테면 Araldit®GT 6071, Araldit®GT 7071, Araldit®GT 7072, Araldit®GT 6063, Araldit®GT 7203, Araldit®GT 6064, Araldit®GT 7304, Araldit®GT 7004, Araldit®GT 6084, Araldit®GT 1999, Araldit®GT 7077, Araldit®GT 6097, Araldit®GT 7097, Araldit®GT 7008, Araldit®GT 6099, Araldit®GT 6608, Araldit®GT 6609, Araldit®GT 6610;
c) 액체 비스페놀 F 디글리시딜 에테르, 이를테면 Araldit®GY 281, Araldit®GY 282, Araldit®PY 302, Araldit®PY 306;
d) CG Epoxy Resin® 0163과 같은 테트라페닐에탄의 고체 폴리글리시딜 에테르;
e) 페놀-포름알데히드 노볼락의 고체 및 액체 폴리글리시딜 에테르, 이를테 면 EPN 1138, EPN 1139, GY 1180, PY 307;
f) o-크레졸-포름알데히드 노볼락의 고체 및 액체 폴리글리시딜 에테르, 이를테면 ECN 1235, ECN 1273, ECN 1280, ECN 1299;
g) 알코올류의 액체 글리시딜 에테르, 이를테면 Shell® 글리시딜 에테르 162, Araldit®DY 0390, Araldit®DY 0391;
h) 카르복시산의 액체 글리시딜 에테르, 이를테면 Shell® Cardura E 테레프탈산 에스테르, 트리멜리트산 에스테르, Araldit®PY 284;
i) 고체 헤테로시클릭 에폭시 수지 (트리글리시딜 이소시아누레이트), 이를테면 Araldit®PT 810;
j) 액체 시클로지방족 에폭시 수지, 이를테면 Araldit®CY 179;
k) p-아미노페놀의 액체 N,N,O-트리글리시딜 에테르, 이를테면 Araldit®MY 0510;
l) 테트라글리시딜-4,4'-메틸렌벤즈아민 또는 N,N,N',N'-테트라글리시딜디아미노페닐메탄, 이를테면 Araldit®MY 720, Araldit®MY 721.
2. 비스옥사졸린, 비스옥사진, 비스옥사졸론 또는 아실락탐. 이들 종류의 화합물은 예를 들면 EP-A-0 583 807 및 EP-A-0 785 967에 기재되어 있다.
비스옥사졸린류로부터의 바람직한 이관능성 화합물은 "T. Loontjens et al., Makromol. Chem., Macromol. Symp. 75, 211-216 (1993)"에 기재되어 있고, 예를 들면 하기 화학식의 화합물들이 있다:
옥사진 또는 옥사졸론으로부터 유도된 다관능성, 특히 이관능성 화합물은 공지되어 있으며, 예를 들면 "H. Inata et al., J. Applied Polymer Science Vol. 32, 4581-4594 (1986)"에 기재되어 있으며; 2,2'-비스(4H-3,1-벤즈옥사진-4-온)이 특히 바람직하다.
아실락탐류로부터 유도된 다관능성, 특히 이관능성 화합물의 예로는 다음 화학식의 화합물이 있다:
상기 식에서,
s는 1∼16, 특히 5∼10이고, 그리고
R126은 방향족 라디칼이다.
락탐 고리가 카프로락탐 또는 라우로락탐인 상기 화학식의 아실락탐류가 바람직하다.
3. 디이소시아네이트, 이를테면 테트라메틸렌 디이소시아네이트, 헥사메틸렌 디이소시아네이트, 도데카메틸렌 디이소시아네이트, 아이코산 1,20-디이소시아네이트, 4-부틸헥사메틸렌 디이소시아네이트, 2,2,4- 또는 2,4,4-트리메틸헥사메틸렌 디이소시아네이트, OCN(CH2)2O(CH2)2NCO, 톨루엔-2,4-디이소시아네이트, p-페닐렌 디이소시아네이트, 크실일렌 디이소시아네이트, 3-이소시아네이토-메틸-3,5,5-트리메틸시클로헥실 이소시아네이트, 나프탈렌 디이소시아네이트, 술포닐 디이소시아네이트, 디페닐메탄, 2,2-디페닐프로판 및 디페닐 에테르의 3,3'-, 4,4'- 및 3,4'-디이소시아네이트, 3,3'-디메틸-4,4'-디이소시아네이토비페닐, 3,3'-디메톡시-4,4'-디이소시아네이토비페닐 및 4,4'-디이소시아네이토디페닐메탄.
4. 디시아네이트, 이를테면 비스페놀 A 디시아네이트.
5. 테트라카르복시산 이무수물, 이를테면 피로멜리트산 이무수물 또는 3,3',4,4'-벤조페논-테트라카르복시산 이무수물.
6. 비스말레이미드류, 이를테면 디페닐메탄비스말레이미드 또는 1,3-페닐렌 비스말레이미드.
7. 카르보디이미드류, 이를테면 폴리(2,4,6-트리이소프로필-1,3-페닐렌카르보디이미드).
상술한 포스포네이트류 및 반응성 첨가제 이외에, 추가 첨가제를 이용할 수도 있다. 그 예는 하기와 같다.
1. 산화방지제
1.1. 알킬화 모노페놀류, 예를 들면 2,6-디-tert-부틸-4-메틸페놀, 2-tert-부틸-4,6-디메틸페놀, 2,6-디-tert-부틸-4-에틸페놀, 2,6-디-tert-부틸-4-n-부틸페놀, 2,6-디-tert-부틸-4-이소부틸페놀, 2,6-디시클로펜틸-4-메틸페놀, 2-(α-메틸시클로헥실)-4,6-디메틸-페놀, 2,6-디옥타데실-4-메틸페놀, 2,4,6-트리시클로헥실페놀, 2,6-디-tert-부틸-4-메톡시메틸페놀, 측쇄가 선형이거나 측쇄인 노닐페놀류, 예를 들면, 2,6-디-노닐-4-메틸페놀, 2,4-디메틸-6-(1'-메틸운데스-1'-일)페놀, 2,4-디메틸-6-(1'-메틸헵타데스-1'-일)페놀, 2,4-디메틸-6-(1'-메틸트리데스-1'-일)페놀 및 이들의 혼합물.
1.2. 알킬티오메틸페놀류, 예를 들면 2,4-디옥틸티오메틸-6-tert-부틸페놀, 2,4-디옥틸티오메틸-6-메틸페놀, 2,4-디옥틸티오메틸-6-에틸페놀, 2,6-디-도데실티오메틸-4-노닐페놀.
1.3. 하이드로퀴논류 및 알킬화 하이드로퀴논류, 예를 들면 2,6-디-tert-부 틸-4-메톡시-페놀, 2,5-디-tert-부틸하이드로퀴논, 2,5-디-tert-아밀하이드로퀴논, 2,6-디페닐-4-옥타데실옥시페놀, 2,6-디-tert-부틸하이드로퀴논, 2,5-디-tert-부틸-4-히드록시아니솔, 3,5-디-tert-부틸-4-히드록시아니솔, 3,5-디-tert-부틸-4-히드록시페닐 스테아레이트, 비스-(3,5-디-tert-부틸-4-히드록시페닐) 아디페이트.
1.4. 토코페롤류, 예를 들면 α-토코페롤, β-토코페롤, γ-토코페롤, δ-토코페롤 및 이들의 혼합물 (비타민 E).
1.5. 히드록실화 티오디페닐 에테르, 예를 들면 2,2'-티오비스(6-tert-부틸-4-메틸페놀), 2,2'-티오비스(4-옥틸페놀), 4,4'-티오비스(6-tert-부틸-3-메틸페놀), 4,4'-티오비스(6-tert-부틸-2-메틸페놀), 4,4'-티오비스-(3,6-디-sec-아밀페놀), 4,4'-비스(2,6-디메틸-4-히드록시페닐)디술피드.
1.6. 알킬리덴비스페놀류, 예를 들면 2,2'-메틸렌 비스(6-tert-부틸-4-메틸페놀), 2,2'-메틸렌 비스(6-tert-부틸-4-에틸페놀), 2,2'-메틸렌 비스[4-메틸-6-(α-메틸시클로헥실)-페놀], 2,2'-메틸렌 비스(4-메틸-6-시클로헥실페놀), 2,2'-메틸렌 비스(6-노닐-4-메틸-페놀), 2,2'-메틸렌 비스(4,6-디-tert-부틸페놀), 2,2'-에틸리덴비스(4,6-디-tert-부틸-페놀), 2,2'-에틸리덴비스(6-tert-부틸-4-이소부틸페놀), 2,2'-메틸렌 비스[6-(α-메틸벤질)-4-노닐페놀], 2,2'-메틸렌 비스[6-(α,α-디메틸벤질)-4-노닐페놀], 4,4'-메틸렌 비스(2,6-디-tert-부틸페놀), 4,4'-메틸렌 비스(6-tert-부틸-2-메틸페놀), 1,1-비스(5-tert-부틸-4-히드록시-2-메틸페닐)부틸, 2,6-비스(3-tert-부틸-5-메틸-2-히드록시벤질)-4-메틸-페놀, 1,1,3-트리스(5-tert-부틸-4-히드록시-2-메틸페닐)부틸, 1,1-비스(5-tert-부틸-4-히드록시-2- 메틸-페닐)-3-n-도데실머캅토부틸, 에틸렌 글리콜 비스[3,3-비스(3'-tert-부틸-4'-히드록시페닐)부티레이트], 비스(3-tert-부틸-4-히드록시-5-메틸-페닐)디시클로펜타디엔, 비스[2-(3'-tert-부틸-2'-히드록시-5'-메틸벤질)-6-tert-부틸-4-메틸페닐]테레프탈레이트, 1,1-비스-(3,5-디메틸-2-히드록시페닐)부틸, 2,2-비스-(3,5-디-tert-부틸-4-히드록시페닐)프로판, 2,2-비스-(5-tert-부틸-4-히드록시2-메틸페닐)-4-n-도데실머캅토부틸, 1,1,5,5-테트라-(5-tert-부틸-4-히드록시-2-메틸페닐)펜탄.
1.7. O-, N- 및 S-벤질 화합물, 예를 들면 3,5,3',5'-테트라-tert-부틸-4,4'-디히드록시디-벤질 에테르, 옥타데실-4-히드록시-3,5-디메틸벤질머캅토아세테이트, 트리데실-4-히드록시-3,5-디-tert-부틸벤질머캅토아세테이트, 트리스(3,5-디-tert-부틸-4-히드록시벤질)아민, 비스(4-tert-부틸-3-히드록시-2,6-디메틸벤질)디티오테레프탈레이트, 비스(3,5-디-tert-부틸-4-히드록시벤질)술피드, 이소옥틸-3,5-디-tert-부틸-4-히드록시벤질머캅토아세테이트.
1.8. 히드록시벤질화 말로네이트류, 예를 들면 디옥타데실-2,2-비스-(3,5-디-tert-부틸-2-히드록시벤질)-말로네이트, 디-옥타데실-2-(3-tert-부틸-4-히드록시-5-메틸벤질)-말로네이트, 디-도데실머캅토에틸-2,2-비스-(3,5-디-tert-부틸-4-히드록시벤질)말로네이트, 비스[4-(1,1,3,3-테트라메틸부틸)페닐]-2,2-비스(3,5-디-tert-부틸-4-히드록시벤질)말로네이트.
1.9. 방향족 히드록시벤질 화합물, 예를 들면 1,3,5-트리스-(3,5-디-tert-부틸-4-히드록시-벤질)-2,4,6-트리메틸벤젠, 1,4-비스(3,5-디-tert-부틸-4-히드록시벤질)-2,3,5,6-테트라메틸벤젠, 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시벤질)페 놀.
1.10. 트리아진 화합물, 예를 들면 2,4-비스(옥틸머캅토)-6-(3,5-디-tert-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-tert-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-tert-부틸-4-히드록시페녹시)-1,3,5-트리아진, 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시페녹시)-1,2,3-트리아진, 1,3,5-트리스-(3,5-디-tert-부틸-4-히드록시-벤질)이소시아누레이트, 1,3,5-트리스(4-tert-부틸-3-히드록시-2,6-디메틸벤질)이소시아누레이트, 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시페닐에틸)-1,3,5-트리아진, 1,3,5-트리스(3,5-디-tert-부틸-4-히드록시-페닐-프로피오닐)-헥사히드로-1,3,5-트리아진, 1,3,5-트리스(3,5-디시클로헥실-4-히드록시벤질)이소시아누레이트.
1.11. 벤질포스포네이트류, 예를 들면 디메틸-2,5-디-tert-부틸-4-히드록시벤질포스포네이트, 디에틸-3,5-디-tert-부틸-4-히드록시벤질포스포네이트, 디옥타데실-3,5-디-tert-부틸-4-히드록시벤질포스포네이트, 디옥타데실-5-tert-부틸-4-히드록시-3-메틸벤질포스포네이트, 3,5-디-tert-부틸-4-히드록시벤질포스폰산의 모노에틸 에스테르의 칼슘염.
1.12. 아실아미노페놀류, 예를 들면 4-히드록시라우르아닐리드, 4-히드록시스테아르아닐리드, 옥틸 N-(3,5-디-tert-부틸-4-히드록시페닐)카바메이트.
1.13. β-(3,5-디- tert -부틸-4- 히드록시페닐 )프로피온산과 모노- 또는 다가 알코올류, 이를테면 메탄올, 에탄올, n-옥탄올, i-옥탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸 렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올-프로판, 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄의 에스테르류.
1.14. β-(5- tert -부틸-4-히드록시-3- 메틸페닐 )프로피온산과 모노- 또는 다가 알코올류, 이를테면 메탄올, 에탄올, n-옥탄올, i-옥탄올, 옥타데칸올, 1,6-헥산-디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸) 이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판, 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄의 에스테르류.
1.15. β-(3,5- 디시클로헥실 -4- 히드록시페닐 )프로피온산과 모노- 또는 다가 알코올류, 이를테면 메탄올, 에탄올, 옥탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판, 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄의 에스테르류.
1.16. 3,5-디- tert -부틸-4- 히드록시페닐 아세트산과 모노- 또는 다가 알코올류, 이를테면 메탄올, 에탄올, 옥탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판, 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄의 에스테르류.
1.17. β-(3,5-디- tert -부틸-4- 히드록시페닐 )프로피온산의 아미드류, 이를테면 N,N'-비스(3,5-디-tert-부틸-4-히드록시페닐프로피오닐)헥사메틸렌 디아미드, N,N'-비스(3,5-디-tert-부틸-4-히드록시-페닐프로피오닐)트리메틸렌 디아미드, N,N'-비스(3,5-디-tert-부틸-4-히드록시페닐프로피오닐)-히드라지드, N,N'-비스[2-(3-[3,5-디-tert-부틸-4-히드록시페닐]프로피오닐옥시)에틸]옥사미드(Naugard®XL-1, Uniroyal 사제).
1.18. 아스코르브산 (비타민 C)
1.19. 아민성 산화방지제, 예를 들면 N,N'-디-이소프로필-p-페닐렌 디아민, N,N'-디-sec-부틸-p-페닐렌 디아민, N,N'-비스(1,4-디메틸펜틸)-p-페닐렌 디아민, N,N'-비스(1-에틸-3-메틸펜틸)-p-페닐렌 디아민, N,N'-비스(1-메틸헵틸)-p-페닐렌 디아민, N,N'-디시클로헥실-p-페닐렌 디아민, N,N'-디페닐-p-페닐렌 디아민, N,N'-비스(2-나프틸)-p-페닐렌 디아민, N-이소프로필-N'-페닐-p-페닐렌 디아민, N-(1,3-디메틸부틸)-N'-페닐-p-페닐렌 디아민, N-(1-메틸헵틸)-N'-페닐-p-페닐렌 디아민, N-시클로헥실-N'-페닐-p-페닐렌디아민, 4-(p-톨루엔술파모일)디페닐아민, N,N'-디 메틸-N,N'-디-sec-부틸-p-페닐렌 디아민, 디페닐아민, N-알릴디페닐아민, 4-이소프로폭시-디페닐아민, N-페닐-1-나프틸아민, N-(4-tert-옥틸페닐)-1-나프틸아민, N-페닐-2-나프틸아민, 옥틸화 디페닐아민, 예를 들면 p,p'-디-tert-옥틸디페닐아민, 4-n-부틸아미노페놀, 4-부티릴아미노페놀, 4-노나노일아미노페놀, 4-도데카노일아미노-페놀, 4-옥타데카노일아미노페놀, 비스(4-메톡시페닐)아민, 2,6-디-tert-부틸-4-디메틸아미노메틸페놀, 2,4'-디아미노디페닐메탄, 4,4'-디아미노디페닐메탄, N,N,N',N'-테트라메틸-4,4'-디아미노디페닐메탄, 1,2-비스[(2-메틸페닐)아미노]에탄, 1,2-비스(페닐아미노)프로판, (o-톨일)비구아니드, 비스[4-(1',3'-디메틸부틸)페닐]아민, tert-옥틸화 N-페닐-1-나프틸아민, 모노- 및 디알킬화 tert-부틸/tert-옥틸디페닐아민의 혼합물, 모노- 및 디알킬화 노닐디페닐아민의 혼합물, 모노- 및 디알킬화 도데실디페닐아민의 혼합물, 모노- 및 디알킬화 이소프로필/이소헥실디페닐아민의 혼합물, 모노- 및 디알킬화 tert-부틸디페닐아민의 혼합물, 2,3-디히드로-3,3-디메틸-4H-1,4-벤조티아진, 페노티아진, 모노- 및 디알킬화 tert-부틸/tert-옥틸페노티아진의 혼합물, 모노- 및 디알킬화 tert-옥틸-페노티아진의 혼합물, N-알릴페노티아진, N,N,N',N'-테트라페닐-1,4-디아미노부트-2-엔, N,N-비스-(2,2,6,6-테트라메틸-피페리드-4-일-헥사메틸렌 디아민, 비스(2,2,6,6-테트라메틸피페리드-4-일)-세바케이트, 2,2,6,6-테트라메틸피페리딘-4-온, 2,2,6,6-테트라메틸피페리딘-4-올.
2.
UV
흡수제 및
광안정화제
2.1. 2-(2'- 히드록시페닐 ) 벤조트리아졸류, 예를 들면 2-(2'-히드록시-5'-메 틸페닐)-벤조-트리아졸, 2-(3',5'-디-tert-부틸-2'-히드록시페닐)벤조트리아졸, 2-(5'-tert-부틸-2'-히드록시페닐)벤조트리아졸, 2-(2'-히드록시-5'-(1,1,3,3-테트라메틸부틸)페닐)벤조트리아졸, 2-(3',5'-디-tert-부틸-2'-히드록시페닐)-5-클로로-벤조트리아졸, 2-(3'-tert-부틸- 2'-히드록시-5'-메틸페닐)-5-클로로-벤조트리아졸, 2-(3'-sec-부틸-5'-tert-부틸-2'-히드록시페닐)벤조트리아졸, 2-(2'-히드록시-4'-옥틸옥시페닐)벤조트리아졸, 2-(3',5'-디-tert-아밀-2'-히드록시페닐)벤조트리-아졸, 2-(3',5'-비스-(α,α-디메틸벤질)-2'-히드록시페닐)벤조트리아졸, 2-(3'-tert-부틸-2'-히드록시-5'-(2-옥틸옥시카르보닐에틸)페닐)-5-클로로-벤조트리아졸, 2-(3'-tert-부틸-5'-[2-(2-에틸헥실-옥시)-카르보닐에틸]-2'-히드록시페닐)-5-클로로-벤조트리아졸, 2-(3'-tert-부틸-2'-히드록시-5'-(2-메톡시카르보닐에틸)페닐)-5-클로로-벤조트리아졸, 2-(3'-tert-부틸-2'-히드록시-5'-(2-메톡시-카르보닐에틸)페닐)벤조트리아졸, 2-(3'-tert-부틸-2'-히드록시-5'-(2-옥틸옥시-카르보닐-에틸)-페닐)벤조트리아졸, 2-(3'-tert-부틸-5'-[2-(2-에틸헥실옥시)카르보닐에틸]-2'-히드록시-페닐)벤조트리아졸, 2-(3'-도데실-2'-히드록시-5'-메틸페닐)벤조트리아졸, 2-(3'-tert-부틸-2'-히드록시-5'-(2-이소옥틸옥시카르보닐에틸)페닐벤조트리아졸, 2,2'-메틸렌 -비스-[4-(1,1,3,3-테트라메틸부틸)-6-벤조트리아졸-2-일페놀]; 2-[3'-tert-부틸-5'-(2-메톡시카르보닐에틸)-2'-히드록시페닐]-2H-벤조트리아졸과 폴리에틸렌 글리콜 300과의 트랜스에스테르화 생성물; (여기서 R은 3'-tert-부틸-4'-히드록시-5'-2H-벤조트리아졸-2-일페닐임), 2-[2'-히드록 시-3'-(α,α-디메틸벤질)-5'-(1,1,3,3-테트라메틸부틸)-페닐]벤조트리아졸; 2-[2'-히드록시-3'-(1,1,3,3-테트라메틸부틸)-5'-(α,α-디메틸벤질)-페닐]벤조트리아졸.
2.2. 2- 히드록시벤조페논류, 예를 들면 4-히드록시, 4-메톡시, 4-옥틸옥시, 4-데실-옥시, 4-도데실옥시, 4-벤질옥시, 4,2',4'-트리히드록시 및 2'-히드록시-4,4'-디메톡시 유도체.
2.3. 치환 및 비치환 벤조산의 에스테르류, 예를 들면 4-tert-부틸-페닐 살리실레이트, 페닐 살리실레이트, 옥틸페닐 살리실레이트, 디벤조일 레조르시놀, 비스(4-tert-부틸벤조일) 레조르시놀, 벤조일 레조르시놀, 2,4-디-tert-부틸페닐 3,5-디-tert-부틸-4-히드록시벤조에이트, 헥사데실 3,5-디-tert-부틸-4-히드록시벤조에이트, 옥타데실 3,5-디-tert-부틸-4-히드록시벤조에이트, 2-메틸-4,6-디-tert-부틸페닐 3,5-디-tert-부틸-4-히드록시벤조에이트.
2.4. 아크릴레이트류, 예를 들면 에틸 α-시아노-β,β-디페닐아크릴레이트, 이소옥틸 α-시아노-β,β-디페닐아크릴레이트, 메틸 α-카르보메톡시신나메이트, 메틸 α-시아노-β-메틸-p-메톡시신나메이트, 부틸 α-시아노-β-메틸-p-메톡시신나메이트, 메틸 α-카르보메톡시-p-메톡시신나메이트 및 N-(β-카르보메톡시-β-시아노비닐)-2-메틸인돌린.
2.5. 니켈 화합물, 예를 들면 2,2'-티오-비스-[4-(1,1,3,3-테트라메틸부틸)페놀]의 니켈 착물, 이를테면 추가 리간드, 이를테면 n-부틸아민, 트리에탄올아민 또는 N-시클로헥실디에탄올아민을 갖거나 갖지않는 1:1 또는 1:2 착물, 니켈 디부 틸디티오카바메이트, 모노알킬 에스테르, 이를테면 메틸 또는 에틸 에스테르의 니켈염, 4-히드록시-3,5-디-tert-부틸벤질포스폰산의 니켈염, 케톡심, 이를테면 2-히드록시-4-메틸페닐 운데실케톡심의 니켈 착물, 추가 리간드를 갖거나 갖지않는 1-페닐-4-라우로일-5-히드록시피라졸의 니켈 착물.
2.6. 입체장애 아민류, 예를 들면 비스(2,2,6,6-테트라메틸-4-피페리딜)세바케이트, 비스(2,2,6,6-테트라메틸-4-피페리딜)숙시네이트, 비스(1,2,2,6,6-펜타메틸-4-피페리딜)세바케이트, 비스(1-옥틸옥시-2,2,6,6-테트라메틸-4-피페리딜)세바케이트, 비스(1,2,2,6,6-펜타메틸-4-피페리딜) n-부틸-3,5-디-tert-부틸-4-히드록시벤질말로네이트, 1-(2-히드록시-에틸)-2,2,6,6-테트라메틸-4-히드록시피페리딘과 숙신산의 축합물, N,N'-비스(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌 디아민과 4-tert-옥틸아미노-2,6-디클로로-1,3,5-트리아진의 선형 또는 시클릭 축합물, 트리스(2,2,6,6-테트라메틸-4-피페리딜)니트릴로트리아세테이트, 테트라키스-(2,2,6,6-테트라메틸-4-피페리딜)-1,2,3,4-부틸-테트라카르복식레이트, 1,1'-(1,2-에탄디일)-비스-(3,3,5,5-테트라-메틸피페라지논), 4-벤조일-2,2,6,6-테트라메틸피페리딘, 4-스테아릴옥시-2,2,6,6-테트라메틸피페리딘, 비스(1,2,2,6,6-펜타메틸피페리딜)-2-n-부틸-2-(2-히드록시-3,5-디-tert-부틸벤질)말로네이트, 3-n-옥틸-7,7,9,9-테트라메틸-1,3,8-트리아자스피로[4.5]데칸-2,4-디온, 비스(1-옥틸옥시-2,2,6,6-테트라메틸피페리딜)세바케이트, 비스(1-옥틸옥시-2,2,6,6-테트라메틸-피페리딜)숙시네이트, N,N'-비스-(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌 디아민과 4-모르폴리노-2,6-디클로로-1,3,5-트리아진의 선형 또는 시클릭 축합물, 2-클로로-4,6-비 스(4-n-부틸아미노-2,2,6,6-테트라메틸피페리딜)-1,3,5-트리아진과 1,2-비스(3-아미노프로필아미노)에탄의 축합물, 2-클로로-4,6-디-(4-n-부틸아미노-1,2,2,6,6-펜타메틸피페리딜)-1,3,5-트리아진과 1,2-비스-(3-아미노프로필아미노)에탄의 축합물, 8-아세틸-3-도데실-7,7,9,9-테트라메틸-1,3,8-트리아자스피로[4.5]데칸-2,4-디온, 3-도데실-1-(2,2,6,6-테트라메틸-4-피페리딜)피롤리딘-2,5-디온, 3-도데실-1-(1,2,2,6,6-펜타메틸-4-피페리딜)피롤리딘-2,5-디온, 4-헥사데실옥시- 및 4-스테아릴옥시-2,2,6,6-테트라메틸피페리딘의 혼합물, N,N'-비스(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌 디아민과 4-시클로헥실아미노-2,6-디클로로-1,3,5-트리아진의 축합 생성물, 1,2-비스(3-아미노프로필아미노)에탄 및 2,4,6-트리클로로-1,3,5-트리아진 뿐만 아니라 4-부틸아미노-2,2,6,6-테트라메틸피페리딘의 축합 생성물(CAS Reg. No. [136504-96-6]); N-(2,2,6,6-테트라메틸-4-피페리딜)-n-도데실숙신이미드, N-(1,2,2,6,6-펜타메틸-4-피페리딜)-n-도데실숙신이미드, 2-운데실-7,7,9,9-테트라메틸-1-옥사-3,8-디아자-4-옥소-스피로[4,5]데칸, 7,7,9,9-테트라메틸-2-시클로운데실-1-옥사-3,8-디아자-4-옥소스피로[4,5]데칸과 에피클로로히드린의 반응 생성물, 1,1-비스(1,2,2,6,6-펜타메틸-4-피페리딜옥시카르보닐)-2-(4-메톡시페닐)에탄, N,N'-비스-포르밀-N,N'-비스(2,2,6,6-테트라메틸-4-피페리딜)헥사메틸렌 디아민, 4-메톡시-메틸렌-말론산과 1,2,2,6,6-펜타메틸-4-히드록시피페리딘의 디에스테르, 폴리[메틸-프로필-3-옥시-4-(2,2,6,6-테트라메틸-4-피페리딜)]실옥산, 말레산 무수물-a-올레핀-공중합체와 2,2,6,6-테트라메틸-4-아미노피페리딘 또는 1,2,2,6,6-펜타-메틸-4-아미노피페리딘의 반응 생성물.
2.7. 옥사미드, 예를 들면 4,4'-디옥틸옥시옥사닐리드, 2,2'-디에톡시옥사닐리드, 2,2'-디옥틸옥시-5,5'-디-tert-부톡사닐리드, 2,2'-디도데실옥시-5,5'-디-tert-부톡사닐리드, 2-에톡시-2'-에틸옥사닐리드, N,N'-비스(3-디메틸아미노프로필)옥사미드, 2-에톡시-5-tert-부틸-2'-에톡사닐리드 및 이와 2-에톡시-2'-에틸-5,4'-디-tert-부톡사닐리드의 혼합물, o- 및 p-메톡시-이치환 옥사닐리드의 혼합물, 및 o- 및 p-에톡시-이치환 옥사닐리드의 혼합물.
2.8. 2-(2- 히드록시페닐 )-1,3,5- 트리아진, 예를 들면 2,4,6-트리스(2-히드록시-4-옥틸옥시페닐)-1,3,5-트리아진, 2-(2-히드록시-4-옥틸옥시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2,4-디히드록시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2,4-비스-(2-히드록시-4-프로필옥시페닐)-6-(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2-히드록시-4-옥틸옥시페닐)-4,6-비스-(4-메틸페닐)-1,3,5-트리아진, 2-(2-히드록시-4-도데실옥시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2-히드록시-4-트리데실옥시페닐)-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-[2-히드록시-4-(2-히드록시-3-부틸옥시-프로폭시)페닐]-4,6-비스(2,4-디메틸)-1,3,5-트리-아진, 2-[2-히드록시-4-(2-히드록시-3-옥틸옥시-프로필옥시)페닐]-4,6-비스(2,4-디메틸)-1,3,5-트리아진, 2-[4-(도데실옥시/트리데실옥시-2-히드록시프로폭시)-2-히드록시-페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-[2-히드록시-4-(2-히드록시-3-도데실옥시-프로폭시)페닐]-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진, 2-(2-히드록시-4-헥실옥시)페닐-4,6-디페닐-1,3,5-트리아진, 2-(2-히드록시-4-메톡시페닐)-4,6-디페닐-1,3,5-트리아진, 2,4,6-트리스[2-히 드록시-4-(3-부톡시-2-히드록시-프로폭시)페닐]-1,3,5-트리아진, 2-(2-히드록시페닐)-4-(4-메톡시페닐)-6-페닐-1,3,5-트리아진, 2-{2-히드록시-4-[3-(2-에틸헥실-1-옥시)-2-히드록시프로필옥시]페닐}-4,6-비스(2,4-디메틸페닐)-1,3,5-트리아진.
3. 금속 탈활성화제, 예를 들면 N,N'-디페닐옥사미드, N-살리실알-N'-살리실로일 히드라진, N,N'-비스(살리실로일) 히드라진, N,N'-비스(3,5-디-tert-부틸-4-히드록시페닐프로피오닐) 히드라진, 3-살리실로일아미노-1,2,4-트리아졸, 비스(벤질리덴)옥살일 디히드라지드, 옥사닐리드, 이소프탈로일 디히드라지드, 세바코일 비스페닐히드라지드, N,N'-디아세틸아디포일 디히드라지드, N,N'-비스(살리실로일)옥살일 디히드라지드, N,N'-비스(살리실로일)티오프로피오닐 디히드라지드.
4. 포스파이트 및 포스포나이트, 예를 들면 트리페닐 포스파이트, 디페닐 알킬 포스파이트, 페닐 디알킬 포스파이트, 트리스(노닐페닐) 포스파이트, 트리라우릴 포스파이트, 트리옥타데실 포스파이트, 디스테아릴 펜타에리트리톨 디포스파이트, 트리스(2,4-디-tert-부틸페닐) 포스파이트, 디이소데실 펜타에리트리톨 디포스파이트, 비스(2,4-디-tert-부틸페닐) 펜타에리트리톨 디포스파이트, 비스(2,6-디-tert-부틸-4-메틸페닐)-펜타에리트리톨 디포스파이트, 디이소데실옥시펜타에리트리톨 디-포스파이트, 비스(2,4-디-tert-부틸-6-메틸페닐)펜타에리트리톨 디포스파이트, 비스(2,4,6-트리스(tert-부틸페닐)펜타에리트리톨 디포스파이트, 트리스테아릴 소르비톨 트리포스파이트, 테트라키스(2,4-디-tert-부틸페닐) 4,4'-비페닐렌 디포스포나이트, 6-이소옥틸옥시-2,4,8,10-테트라-tert-부틸-12H-디-벤즈[d,g]-1,3,2-디옥사포스포신, 6-플루오로-2,4,8,10-테트라-tert-부틸-12-메틸-디벤즈[d,g]- 1,3,2-디옥사포스포신, 비스(2,4-디-tert-부틸-6-메틸페닐) 메틸 포스파이트, 비스(2,4-디-tert-부틸-6-메틸페닐) 에틸 포스파이트, 2,2',2''-니트릴로[트리에틸트리스(3,3',5,5'-테트라-tert-부틸-1,1'-비페닐-2,2'-디일)포스파이트], 2-에틸헥실(3,3',5,5'-테트라-tert-부틸-1,1'-비페닐-2,2'-디일)포스파이트.
특히 바람직한 것은 다음과 같은 포스파이트류이다:
트리스(2,4-디-tert-부틸페닐)포스파이트 (Irgafos®68, Ciba-Geigy), 트리스(노닐페닐) 포스파이트,
5. 히드록실아민류, 예를 들면, N,N-디벤질히드록실아민, N,N-디에틸히드록실아민, N,N-디옥틸히드록실아민, N,N-디라우릴히드록실아민, N,N-디테트라데실히드록실아민, N,N-디헥사데실히드록실아민, N,N-디옥타데실히드록실아민, N-헥사데실-N-옥타데실히드록실아민, N-헵타데실-N-옥타데실히드록실아민, 수소화 수지(tallow) 아민으로부터 유도된 N,N-디알킬히드록실아민.
6. 니트론류, 예를 들면, N-벤질-α-페닐-니트론, N-에틸-α-메틸-니트론, N-옥틸-α-헵틸-니트론, N-라우릴-α-운데실-니트론, N-테트라데실-α-트리데실-니트론, N-헥사데실-α-펜타데실-니트론, N-옥타데실-α-헵타데실-니트론, N-헥사데실-α-헵타데실-니트론, N-옥타데실-α-펜타데실-니트론, N-헵타데실-α-헵타데실-니트론, N-옥타데실-α-헥사데실-니트론, 수소화 수지 아민으로부터 유도된 N,N-디 알킬히드록실아민으로부터 유도된 니트론.
7. 티오상승제류, 예를 들면, 디라우릴 티오디프로피오네이트 또는 디스테아릴 티오디프로피오네이트.
8. 과산화물 스캐빈저류, 예를 들면 β-티오디-프로피온산의 에스테르류, 이를테면 라우릴, 스테아릴, 미리스틸 또는 트리데실 에스테르, 머캅토벤즈이미다졸 또는 2-머캅토-벤즈이미다졸의 아연염, 아연 디부틸디티오카바메이트, 디옥타데실 디술피드, 펜타에리트리톨 테트라키스(β-도데실머캅토)프로피오네이트.
9. 폴리아미드 안정화제, 예를 들면, 요오드화물 및/또는 인 화합물과 조합된 구리염 및 이가 망간염.
10. 염기성( Basic ) 공- 안정화제, 예를 들면, 멜라민, 폴리비닐피롤리돈, 디시안디아미드, 트리알릴 시아누레이트, 우레아 유도체, 히드라진 유도체, 아민, 폴리아미드, 폴리우레탄, 고급 지방산의 알칼리 금속 염 및 알칼리 토 금속 염, 예를 들면 칼슘 스테아레이트, 아연 스테아레이트, 마그네슘 베헤네이트, 마그네슘 스테아레이트, 나트륨 리시놀레에이트 및 칼륨 팔미테이트, 안티몬 피로카테콜레이트 또는 아연 피로카테콜레이트.
11. 핵 생성제, 예를 들면, 무기 물질, 이를테면 할석, 금속 산화물, 이를테면 이산화티탄 또는 산화 마그네슘, 바람직하게는 알칼리 토금속의 포스페이트, 카보네이트 또는 설페이트; 유기 화합물 , 이를테면 모노- 또는 폴리카르복시산 및 그의 염, 이를테면 4-tert-부틸벤조산, 아디프산, 디페닐아세트산, 나트륨 숙시네이트 또는 나트륨 벤조에이트; 중합성 화합물, 이를테면 이온성 공중합체 (이오노 머).
12. 충전제 및 보강제, 예를 들면, 탄산칼슘, 규산염, 유리 섬유, 유리 벌브, 석면, 탈크, 카올린, 운모, 황산바륨, 금속 산화물 및 수산화물, 카본블랙, 흑연, 목재 가루 및 기타 천연 물품의 가루 또는 섬유, 합성 섬유.
13. 기타 첨가제, 예를 들면, 가소제, 윤활제, 유화제, 안료, 레올로지(rheology) 첨가제, 촉매, 유동 조절제, 광택제, 난연제, 대전방지제 및 발포제.
14. 벤조푸란온류 및 인돌리논류, 예를 들면 U.S. 4,325,863; U.S. 4,338,244; U.S. 5,175,312; U.S. 5,216,052; U.S. 5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 또는 EP-A-0591102에 기재된 것; 또는 3-[4-(2-아세톡시에톡시)-페닐]-5,7-디-tert-부틸-벤조푸란-2-온, 5,7-디-tert-부틸-3-[4-(2-스테아로일옥시에톡시)페닐]벤조푸란-2-온, 3,3'-비스[5,7-디-tert-부틸-3-(4-[2-히드록시에톡시]페닐)벤조푸란-2-온], 5,7-디-tert-부틸-3-(4-에톡시페닐)벤조푸란-2-온, 3-(4-아세톡시-3,5-디메틸페닐)-5,7-디-tert-부틸-벤조푸란-2-온, 3-(3,5-디메틸-4-피발로일옥시페닐)-5,7-디-tert-부틸-벤조푸란-2-온, 3-(3,4-디메틸페닐)-5,7-디-tert-부틸-벤조푸란-2-온, 3-(2,3-디메틸페닐)-5,7-디-tert-부틸-벤조푸란-2-온.
본 발명에서 바람직한 것은 상기 2.1, 2.6 및 2.7의 광안정화제, 이를테면 Chimassorb 944, Chimassorb 119, Tinuvin 234, Tinuvin 312, Tinuvin 622 또는 Tinuvin 770의 광안정화제이다. 바람직한 것은 또한 방향족 포스파이트 또는 포스포나이트이다.
마찬가지로 바람직한 방법은 포스파이트 및/또는 입체장애 페놀이 추가로 이용되는 방법이다. 또한 바람직한 것은 폴리아미드 안정화제, 예를 들면, 요오드화물 및/또는 인 화합물과 조합된 구리염 및 이가 망간염이다.
첨가제는 교반장치가 구비되고 가열될 수 있는 어떠한 용기 내에서 중합체에 첨가되고 혼합될 수 있다. 이들의 예는 밀페된 장치, 이를테면 반죽 장치, 혼합기 또는 교반된 용기이다. 혼합 공정은 압출기 또는 반죽 장치에서 바람직하게 실시된다. 그 공정이 불활성 분위기에서 작동되느냐 또는 산소 분위기 하에서 작동되느냐는 중요하지 않다.
포스포네이트는 1 이상의 단량체 또는 나일론 염에 용해 또는 분산될 수 있으며, 그에 따라 중축합반응 또는 다중부가반응에 첨가될 수 있다. 분말 또는 액체로서 포스포네이트를 반응 용기에 직접 첨가할 수 있다. 또한, 포스포네이트는 중축합반응 또는 다중부가반응의 어느 단계에서도 첨가될 수 있다. 한편, 폴리이미드 담체에서 포스포네이트의 고체 또는 용융 매스터뱃치(masterbatch)는 반응의 어느 단계에서도 첨가제를 첨가하는 데 사용될 수 있다.
바람직하게는, 포스포네이트는 반응 초기에 존재한다.
또한 본 발명의 요지는 다음 성분을 포함하는 조성물에 있다:
a) 이산 및 디아민 단량체 또는 락탐 단량체 및
b) 포스포네이트.
본 발명의 또 다른 요지는 이산 및 디아민 단량체로부터 출발하거나 또는 락탐 단량체로부터 출발하고 포스포네이트의 존재 하에서 중축합반응 또는 다중부가 반응을 실시하는 것을 포함하는 폴리아미드 예비중합체를 제조하기 위해 포스포네이트를 사용하는 데 있다.
또 다른 요지는 상기 방법에 따라 얻어질 수 있는 폴리아미드에 있다.
바람직한 경우와 정의는 상기 공정에서 이미 제공되었다. 이들은 또한 본 발명의 다른 요지에도 적용할 수 있다.
다음 실시예에서는 본 발명을 더욱 상세히 설명한다.
일반 사항:
상대 점도(
RV
)의 측정:
상대점도(RV) PA 6.6은 포름산 용액의 점도에 대한 90% 포름산의 용액 중에서 8.4 중량% 중합체의 용액의 점도 비이다. 5.5g의 중합체를 50 ml 포름산(90%)에 용해한다. 점도 측정은 25℃에서 Cannon-Fenske 점도계를 사용하여 실시된다.
고체 상태
중축합반응
(
SSP
):
SSP를 실시하기 전에, 매 샘플 (압출 또는 합성된 PA 6,6)을 80℃의 진공 하에서 2 시간 동안 건조한다.
폴리아미드 6.6의 합성:
제 1단계:
PA
6.6 염의 제조:
2개의 적하 깔대기가 구비되어 있고 32℃의 물이 들어있는 500 ml-플라스크에서 반응을 실시한다. 제1 적하 깔대기에는 13.92 g (0.119 몰)의 헥사메틸렌디아민을 25 ml의 메탄올에 용해하고, 다른 깔대기에는 17.70 g (0.120 몰)의 아디프산과 80 ml의 메탄올로 이루어진 용액을 함유한다. 두 용액을 동시에(2 분 동안) 플 라스크에 적하하고, 온도를 45∼50℃까지 승온시킨다. 첨가를 종료한 후, 플라스크를 8℃까지 냉각시킨다. 즉시 침전된 PA 6.6 염 (=아디프산/헥사메틸렌디아민 염)을 여과해 낸다. 22 ml의 차가운 메탄올로 2회 세척한 후, 일정량이 될 때까지 염을 60℃의 진공에서 건조하고, 사용할 때까지 데시케이터 내의 P2O5 상에 저장한다.
백색 고체의 염을 얻는다.
전환율: 96∼99%
융점: 186∼187℃
pH-값: 약 7.62
제2 단계: 폴리아미드 6.6 (
PA
6.6) 예비중합체의 제조
1L-Buchi 오토클레이브를 진공으로 한 후, 사용하기 전에 질소 가스로 채운다. 제 1단계의 아디프산/헥사메틸렌디아민 염 150g 그리고 Irgamod 195 또는 Irgamod 295 각각 1000 ppm을 첨가한 후, 반응기를 진공으로 한 다음, 다시 질소 가스로 채운다. 혼합물을 30 분 동안 교반한 다음, 온도를 225℃까지 승온시킨다. 이 온도 및 8∼11 바아에서 1.5 시간 동안 오토클레이브를 환기시키고 그 혼합물을 질소 분위기 하에서 15분 동안 교반한다. 실온까지 냉각한 후 생성된 폴리아미드 6.6을 물리적으로 제거한 다음 분쇄한다.
백색 분말로서 폴리아미드를 얻는다.
Irgamod®195는 시바스페셜티 케미칼스 사에서 생산하는 포스포네이트이다.
Irgamod®295는 시바스페셜티 케미칼스 사에서 생산하는 포스포네이트이다.
Irgafos®168은 시바스페셜티 케미칼스 사에서 생산하는 포스파이트이인 트리스(2,4-디-tert-부틸페닐) 포스파이트이다.
제 3단계:
PA
6.6의 압출
분쇄된 중합체(단계 2)를 진공 하, 260∼280℃ 및 50 rpm 에서 2중 스크루 압출기(Haake TW 100)에 의해 압출한다. 그 결과 얻어진 폴리아미드를 스트랜드 과립화하고, 그 물질을 진공에서 철야 건조한 다음, MFR (ISO 1133에 따름)의 측정 전에 진공에서 철야 건조한다.
PA6.6 압출 후(온도 260∼280℃, 50 rpm, 진공)
MFR = 용융 유동속도(melt flow rate)
RV = 상대점도
결과를 비교하면, MFR 측정과 RV 값이 일치한다는 것을 알 수 있다. 포스포네이트없이(PA 순수) 합성하면 저분자량(고 MFR; 저 RV)의 황색 중합체가 얻어진다. Irgamod 195 또는 Irgamod 295를 첨가하면, 색상이 변하지 않는 고 분자량의 폴리아미드(Irgamod 295의 경우에 시중 상품급(No. 1)를 얻게된다. 포스파이트, 이를테면 Irgafos 168을 사용하면, 고 분자량의 중합체가 얻어지지만, 그 색상은 허용할 수 없다.
결론:
이들 결과로부터, 예비중합체의 제조 초기에 포스포네이트, 이를테면 Irgamod 195 또는 Irgamod 295를 첨가하면 분자량 증가를 촉진하고 무색 중합체를 얻을 수 있다는 것을 입증한다.
후속적인 SSP:
샘플 번호 3 및 4 (제3 단계 참조)를 사용하고, 200℃의 질소 흐름 하에서 4 시간 동안 고체 상태 중축합반응을 실시한다. 비교 실험을 위해, 1000 ppm의 Irgamod 195 또는 1000 ppm의 Irgamod 295를 각각 갖는 시중 상품 PA 6.6 (Terez PA 66)을 마찬가지로 SSP에 도입한다. 이들 두 혼합물을 압출(온도 260℃∼280℃)하고, 그 결과 얻어진 중합체 샘플을 스트랜드 과립한다. 모든 샘플을 동일한 SSP 과정(샘플 번호 3 및 4, 그리고 비교 실험 3 및 4)을 거친다. 그 결과를 하기 표에 나타낸다.
비교 실험 3 = Terez PA 66 + 1000 ppm Irgamod 295, 압출
본 발명 실험 3 = 1000 ppm의 Irgamod 295를 함유하는, 합성된 PA 66, 압출
비교 실험 4 = Terez PA 66 + 1000 ppm Irgamod 195, 압출
본 발명 실험 4 = 1000 ppm의 Irgamod 195를 함유하는, 합성된 PA 66, 압출
이들 실시예에서는 첨가제가 후공정 단계에서보다 예비중합체 제조 단계에서 첨가될 때 더욱 효과적이라는 것을 나타낸다.
본 발명에서는 예비 중합 단계에서 폴리아미드의 분자량을 증가시킨다.
Claims (14)
- 이산 및 디아민 단량체로부터 또는 락탐 단량체로부터 출발하고 포스포네이트의 존재 하에서 중축합반응 또는 다중부가반응을 실시하는 것을 포함하는 폴리아미드 예비중합체의 제조방법.
- 제 1항에 있어서, 단량체가 테트라메틸렌디아민, 헥사메틸렌디아민, 디아미노데칸, 디아미노도데칸, 아디프산, 아젤라산, 세바스산, 도데칸디오산, ε-카프로락탐, 운데칸락탐, 라우로락탐 및 이들의 혼합물로 이루어진 군으로부터 선택되는 방법.
- 제 1항에 있어서, 폴리아미드 예비중합체가 폴리아미드 PA 4.6, PA 6.6; PA 6.9; PA 6.10, PA 6.12, PA 10.12, PA 12.12, PA 6, PA 11, PA 12 또는 PA 6/66 블렌드인 방법.
- 제 2항에 있어서, 단량체가 헥사메틸렌디아민 아디프산을 포함하는 방법.
- 제 1항에 있어서, 포스포네이트가 하기 화학식(I)을 갖는 방법:상기 식에서,R3은 H, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸이고,R4는 수소, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸; 또는Mr +/r이고,Mr +은 r-가 금속 양이온 또는 암모늄 이온이고,n은 0, 1, 2, 3, 4, 5 또는 6이고,r은 1, 2, 3 또는 4이고;Q는 수소, -X-C(O)-OR7, 또는 라디칼R1은 이소프로필, tert-부틸, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,R2는 수소, C1-C4알킬, 시클로헥실, 또는 1-3 C1-C4알킬기 알킬기에 의해 치환된 시클로헥실이고,R5는 H, C1-C18알킬, OH, 할로겐 또는 C3-C7시클로알킬이고;R6은 H, 메틸, 트리메틸실일, 벤질, 페닐, 술포닐 또는 C1-C18알킬이고;R7은 H, C1-C10알킬 또는 C3-C7시클로알킬이고; 그리고X는 페닐렌, C1-C4알킬기-치환 페닐렌 또는 시클로헥실렌이다.
- 제 5항에 있어서, 포스포네이트가 하기 화학식(Ia)의 화합물인 방법:상기 식에서,R1은 H, 이소프로필, tert-부틸, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,R2는 수소, C1-C4알킬, 시클로헥실, 또는 1-3 C1-C4알킬기에 의해 치환된 시클로헥실이고,R3은 C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸이고,R4는 수소, C1-C20알킬, 비치환 또는 C1-C4알킬-치환 페닐 또는 나프틸; 또는Mr +/r이고,Mr +은 r-가 금속 양이온이고,n은 1, 2, 3, 4, 5 또는 6이고, 그리고r은 1, 2, 3 또는 4이다.할로겐은 플루오로, 클로로, 브로모 또는 요오도이다.
- 제 1항에 있어서, 단량체 또는 단량체류 당 포스포네이트 10∼20 000 ppm이 사용되는 방법.
- 제 1항에 있어서, 중축합반응 또는 다중부가반응 온도가 150℃∼280℃인 방법.
- 제 1항에 있어서, 중축합반응 또는 다중부가반응 동안 압력이 3∼20 바아인 방법.
- 제 1항에 있어서, 후속적인 고체 상태 중축합반응이 폴리아미드 예비중합체에 적용되는 방법.
- 다음 성분을 포함하는 조성물:a) 이산 및 디아민 단량체 또는 락탐 단량체 및b) 포스포네이트.
- 이산 및 디아민 단량체로부터 출발하거나 또는 락탐 단량체로부터 출발하고 포스포네이트의 존재 하에서 중축합반응 또는 다중부가반응을 실시하는 것을 포함하는, 폴리아미드 예비중합체를 제조하기 위한 포스포네이트의 용도.
- 제 1항의 방법에 따라 얻어지는 폴리아미드.
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EP05106168 | 2005-07-07 | ||
EP05106168.7 | 2005-07-07 |
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US (1) | US20100036083A1 (ko) |
EP (1) | EP1907467A1 (ko) |
JP (1) | JP2008545055A (ko) |
KR (1) | KR20080040640A (ko) |
CN (1) | CN101218289A (ko) |
TW (1) | TW200714633A (ko) |
WO (1) | WO2007006647A1 (ko) |
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CN104271654B (zh) | 2012-03-20 | 2016-10-19 | 巴斯夫欧洲公司 | 具有改进的光学特性的聚酰胺组合物 |
CN104321377A (zh) | 2012-03-20 | 2015-01-28 | 巴斯夫欧洲公司 | 用于改进聚酰胺树脂固态特性的脲化合物 |
BR112016027990B1 (pt) | 2014-05-30 | 2022-01-18 | Ascend Performance Materials Operations Llc | Poliamidas de cor reduzida e baixo teor de fósforo que apresentam forma sólida |
DE102018220616B3 (de) * | 2018-11-20 | 2019-05-29 | Thyssenkrupp Ag | Verfahren zur Herstellung von Polyamid 6 |
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FR1531145A (fr) * | 1966-07-13 | 1968-06-28 | Ici Ltd | Polyamides |
US5432254A (en) * | 1993-04-26 | 1995-07-11 | Zimmer Aktiengesellschaft | Discontinuous catalytic process for the production of polyamide-6,6 |
US5496920A (en) * | 1993-06-07 | 1996-03-05 | Ciba-Geigy Corporation | Increasing the molecular weight of polyamides |
CZ292251B6 (cs) * | 1994-10-14 | 2003-08-13 | Ciba Specialty Chemicals Holding Inc. | Způsob zvyšování molekulové hmotnosti polykondenzátů |
DE10334497A1 (de) * | 2003-07-29 | 2005-02-24 | Degussa Ag | Polymerpulver mit phosphonatbasierendem Flammschutzmittel, Verfahren zu dessen Herstellung und Formkörper, hergestellt aus diesem Polymerpulver |
CA2537061A1 (en) * | 2003-09-25 | 2005-04-07 | Ciba Specialty Chemicals Holding Inc. | Molecular weight increase and modification of polycondensates |
DE602004003836T2 (de) * | 2003-09-26 | 2007-08-09 | Ciba Speciality Chemicals Holding Inc. | Verfahren zur verbesserung der farbe von polykondensaten |
WO2005054328A1 (en) * | 2003-12-04 | 2005-06-16 | Ciba Specialty Chemicals Holding Inc. | Stabilization of polyether polyols, polyester polyols and polyurethanes |
BRPI0620902A2 (pt) * | 2006-01-04 | 2011-11-29 | Ciba Holding Inc | composições estabilizadas de combustìvel biodiesel |
WO2007096276A1 (en) * | 2006-02-24 | 2007-08-30 | Ciba Holding Inc. | Viscosity breaking process for olefin polymers |
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2006
- 2006-06-28 KR KR1020077030340A patent/KR20080040640A/ko not_active Application Discontinuation
- 2006-06-28 EP EP06777495A patent/EP1907467A1/en not_active Withdrawn
- 2006-06-28 CN CNA2006800246749A patent/CN101218289A/zh active Pending
- 2006-06-28 US US11/988,198 patent/US20100036083A1/en not_active Abandoned
- 2006-06-28 JP JP2008519900A patent/JP2008545055A/ja not_active Withdrawn
- 2006-06-28 WO PCT/EP2006/063615 patent/WO2007006647A1/en active Application Filing
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CN101218289A (zh) | 2008-07-09 |
JP2008545055A (ja) | 2008-12-11 |
WO2007006647A1 (en) | 2007-01-18 |
EP1907467A1 (en) | 2008-04-09 |
US20100036083A1 (en) | 2010-02-11 |
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