BRPI0407255B1 - Composições de resina, artigo conformado, processos para provimento de uma poliolefina e para o aumento de temperatura de cristalização desta, filme orientado monoaxial ou biaxialmente, sistemas multicamadas, compostos e seus usos, e mistura - Google Patents

Info

Publication number

BRPI0407255B1

BRPI0407255B1 BRPI0407255-3A BRPI0407255A BRPI0407255B1 BR PI0407255 B1 BRPI0407255 B1 BR PI0407255B1 BR PI0407255 A BRPI0407255 A BR PI0407255A BR PI0407255 B1 BRPI0407255 B1 BR PI0407255B1

Authority

BR

Brazil

Prior art keywords

bis

butyl

benzamide

methyl

fact

Prior art date

2003-02-14

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 100
• 238000000034 method Methods 0.000 title claims description 65
• 230000008569 process Effects 0.000 title claims description 44
• 238000002425 crystallisation Methods 0.000 title claims description 13
• 230000008025 crystallization Effects 0.000 title claims description 13
• 239000011342 resin composition Substances 0.000 title abstract description 4
• 238000002156 mixing Methods 0.000 title description 3
• 239000000203 mixture Substances 0.000 claims abstract description 119
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 113
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 19
• -1 -tert-butyl diamide Chemical compound 0.000 claims description 321
• 229910052757 nitrogen Inorganic materials 0.000 claims description 79
• 229920001577 copolymer Polymers 0.000 claims description 70
• 239000000654 additive Substances 0.000 claims description 32
• 239000004743 Polypropylene Substances 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 23
• 150000003254 radicals Chemical class 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 20
• 229920001155 polypropylene Polymers 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
• 239000005977 Ethylene Substances 0.000 claims description 19
• 230000000996 additive effect Effects 0.000 claims description 18
• 238000002347 injection Methods 0.000 claims description 17
• 239000007924 injection Substances 0.000 claims description 17
• 239000002667 nucleating agent Substances 0.000 claims description 16
• 229920000098 polyolefin Polymers 0.000 claims description 15
• 229920002554 vinyl polymer Polymers 0.000 claims description 15
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 239000004952 Polyamide Substances 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 229920002647 polyamide Polymers 0.000 claims description 12
• 238000001125 extrusion Methods 0.000 claims description 11
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 239000000835 fiber Substances 0.000 claims description 9
• 238000000465 moulding Methods 0.000 claims description 9
• YARNUSSCRCMUME-UHFFFAOYSA-N 5-(2,2-dimethylpropanoylamino)benzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C(=O)NC1=CC(C(O)=O)=CC(C(O)=O)=C1 YARNUSSCRCMUME-UHFFFAOYSA-N 0.000 claims description 8
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 229920001519 homopolymer Polymers 0.000 claims description 7
• 239000000314 lubricant Substances 0.000 claims description 7
• 239000004711 α-olefin Substances 0.000 claims description 7
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 6
• XGPSTLRFHJVMTP-UHFFFAOYSA-N n'-(2,2-dimethylpropanoyl)benzohydrazide Chemical compound CC(C)(C)C(=O)NNC(=O)C1=CC=CC=C1 XGPSTLRFHJVMTP-UHFFFAOYSA-N 0.000 claims description 6
• CPEULHAPWXMDDV-UHFFFAOYSA-N n-[3,5-bis(2,2-dimethylpropanoylamino)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC(NC(=O)C(C)(C)C)=CC(NC(=O)C(C)(C)C)=C1 CPEULHAPWXMDDV-UHFFFAOYSA-N 0.000 claims description 6
• 229920005629 polypropylene homopolymer Polymers 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 150000002978 peroxides Chemical class 0.000 claims description 5
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 4
• XXNOZIMYHXRVAG-UHFFFAOYSA-N 3,5-bis(2,2-dimethylpropanoylamino)-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC(NC(=O)C(C)(C)C)=CC(NC(=O)C(C)(C)C)=C1 XXNOZIMYHXRVAG-UHFFFAOYSA-N 0.000 claims description 4
• CPYKOJLWWVNMQZ-UHFFFAOYSA-N 3,5-bis(2-methylpropanoylamino)-n-(2,4,4-trimethylpentan-2-yl)benzamide Chemical compound CC(C)C(=O)NC1=CC(NC(=O)C(C)C)=CC(C(=O)NC(C)(C)CC(C)(C)C)=C1 CPYKOJLWWVNMQZ-UHFFFAOYSA-N 0.000 claims description 4
• HXRKJMFSXYOVOW-UHFFFAOYSA-N 3,5-bis(2-methylpropanoylamino)-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC(NC(=O)C(C)C)=CC(NC(=O)C(C)C)=C1 HXRKJMFSXYOVOW-UHFFFAOYSA-N 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 235000006708 antioxidants Nutrition 0.000 claims description 4
• 229920001400 block copolymer Polymers 0.000 claims description 4
• 238000010348 incorporation Methods 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• CMLHEHXOWQWJKX-UHFFFAOYSA-N n-(3-methylbutyl)-3,5-bis(4-methylpentanoylamino)benzamide Chemical compound CC(C)CCNC(=O)C1=CC(NC(=O)CCC(C)C)=CC(NC(=O)CCC(C)C)=C1 CMLHEHXOWQWJKX-UHFFFAOYSA-N 0.000 claims description 4
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 229920005604 random copolymer Polymers 0.000 claims description 4
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
• YOUSVCIYWQHESX-UHFFFAOYSA-N 3,5-bis(3-methylbutanoylamino)-n-(3-methylbutyl)benzamide Chemical compound CC(C)CCNC(=O)C1=CC(NC(=O)CC(C)C)=CC(NC(=O)CC(C)C)=C1 YOUSVCIYWQHESX-UHFFFAOYSA-N 0.000 claims description 3
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 238000007664 blowing Methods 0.000 claims description 3
• RNMNIWCXWPCKEN-UHFFFAOYSA-N n-[3,5-bis(2,2-dimethylpropanoylamino)phenyl]-3,3-dimethylbutanamide Chemical compound CC(C)(C)CC(=O)NC1=CC(NC(=O)C(C)(C)C)=CC(NC(=O)C(C)(C)C)=C1 RNMNIWCXWPCKEN-UHFFFAOYSA-N 0.000 claims description 3
• GYXDNDSUBCPBNZ-UHFFFAOYSA-N n-[3-(2,2-dimethylpropanoylamino)-5-(2-methylpropanoylamino)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)C(=O)NC1=CC(NC(=O)C(C)(C)C)=CC(NC(=O)C(C)(C)C)=C1 GYXDNDSUBCPBNZ-UHFFFAOYSA-N 0.000 claims description 3
• 150000002989 phenols Chemical class 0.000 claims description 3
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
• 238000001175 rotational moulding Methods 0.000 claims description 3
• 238000009987 spinning Methods 0.000 claims description 3
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 2
• 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 2
• QLMGIWHWWWXXME-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetic acid Chemical class CC(C)(C)C1=CC(CC(O)=O)=CC(C(C)(C)C)=C1O QLMGIWHWWWXXME-UHFFFAOYSA-N 0.000 claims description 2
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 2
• WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical class CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 2
• FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical class CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 claims description 2
• VPWLFOOAVIRLEF-UHFFFAOYSA-N 3-hydroperoxy-3-oxopropanoic acid Chemical class OOC(=O)CC(O)=O VPWLFOOAVIRLEF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 229930185605 Bisphenol Natural products 0.000 claims description 2
• LTBRACVJRXLQHC-UHFFFAOYSA-N OP(=O)OCC1=CC=CC=C1 Chemical class OP(=O)OCC1=CC=CC=C1 LTBRACVJRXLQHC-UHFFFAOYSA-N 0.000 claims description 2
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 2
• 235000010323 ascorbic acid Nutrition 0.000 claims description 2
• 239000011668 ascorbic acid Substances 0.000 claims description 2
• 229960005070 ascorbic acid Drugs 0.000 claims description 2
• 150000001559 benzoic acids Chemical class 0.000 claims description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 2
• 238000007906 compression Methods 0.000 claims description 2
• 230000006835 compression Effects 0.000 claims description 2
• 150000002443 hydroxylamines Chemical class 0.000 claims description 2
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 2
• 239000006078 metal deactivator Substances 0.000 claims description 2
• ZOPZLMGYAAOUQM-UHFFFAOYSA-N n-[3,5-bis(2-methylpropanoylamino)phenyl]-3,3-dimethylbutanamide Chemical compound CC(C)C(=O)NC1=CC(NC(=O)CC(C)(C)C)=CC(NC(=O)C(C)C)=C1 ZOPZLMGYAAOUQM-UHFFFAOYSA-N 0.000 claims description 2
• GNEBSLDFZWGFSB-UHFFFAOYSA-N n-[3-(3,3-dimethylbutanoylamino)-5-(2,2-dimethylpropanoylamino)phenyl]-3,3-dimethylbutanamide Chemical compound CC(C)(C)CC(=O)NC1=CC(NC(=O)CC(C)(C)C)=CC(NC(=O)C(C)(C)C)=C1 GNEBSLDFZWGFSB-UHFFFAOYSA-N 0.000 claims description 2
• 150000002816 nickel compounds Chemical class 0.000 claims description 2
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
• 229930003799 tocopherol Natural products 0.000 claims description 2
• 239000011732 tocopherol Substances 0.000 claims description 2
• 235000019149 tocopherols Nutrition 0.000 claims description 2
• 150000003918 triazines Chemical class 0.000 claims description 2
• JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• GZUZMDDAJCZRRI-UHFFFAOYSA-N 5-(2,2-dimethylbutanoylamino)benzene-1,3-dicarboxylic acid Chemical compound CCC(C)(C)C(=O)NC1=CC(C(O)=O)=CC(C(O)=O)=C1 GZUZMDDAJCZRRI-UHFFFAOYSA-N 0.000 claims 4
• 239000004744 fabric Substances 0.000 claims 4
• NEZORLJFVGEQNO-UHFFFAOYSA-N CC(CC(=O)NC1=C(C(=CC(=C1)NC(C(CC)(C)C)=O)NC(CC(C)(C)C)=O)N)(C)C Chemical compound CC(CC(=O)NC1=C(C(=CC(=C1)NC(C(CC)(C)C)=O)NC(CC(C)(C)C)=O)N)(C)C NEZORLJFVGEQNO-UHFFFAOYSA-N 0.000 claims 1
• 230000009977 dual effect Effects 0.000 claims 1
• 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims 1
• 229920005615 natural polymer Polymers 0.000 abstract description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 201
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• 238000002360 preparation method Methods 0.000 description 96
• 238000002844 melting Methods 0.000 description 83
• 230000008018 melting Effects 0.000 description 83
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• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 54
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• 238000001953 recrystallisation Methods 0.000 description 45
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• 238000000746 purification Methods 0.000 description 42
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• 239000000047 product Substances 0.000 description 36
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
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• 229940086542 triethylamine Drugs 0.000 description 25
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• 239000001993 wax Substances 0.000 description 22
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• 125000004356 hydroxy functional group Chemical group O* 0.000 description 18
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 18
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• KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
• 238000005917 acylation reaction Methods 0.000 description 12
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• 238000005984 hydrogenation reaction Methods 0.000 description 12
• PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 11
• 230000010933 acylation Effects 0.000 description 11
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• NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 10
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
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