ES2451815T3 - Uso de derivados protegidos n-hidroxiimida y metales de transición como sistema captador de oxígeno en películas transparentes de poliolefina - Google Patents

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Publication number

ES2451815T3

ES2451815T3 ES10784511.7T ES10784511T ES2451815T3 ES 2451815 T3 ES2451815 T3 ES 2451815T3 ES 10784511 T ES10784511 T ES 10784511T ES 2451815 T3 ES2451815 T3 ES 2451815T3

Authority

ES

Spain

Prior art keywords

substituted

unsubstituted

alkyls

phenyl

tert

Prior art date

2009-12-02

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.)

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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 101
• 239000001301 oxygen Substances 0.000 title claims abstract description 101
• 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 101
• 230000002000 scavenging effect Effects 0.000 title claims abstract description 29
• 229920000098 polyolefin Polymers 0.000 title claims abstract description 11
• 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 11
• 150000003624 transition metals Chemical class 0.000 title description 7
• -1 transition metal salt Chemical class 0.000 claims abstract description 114
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 57
• 239000000203 mixture Substances 0.000 claims abstract description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 19
• 239000000654 additive Substances 0.000 claims abstract description 18
• 229910052751 metal Inorganic materials 0.000 claims abstract description 17
• 239000002184 metal Substances 0.000 claims abstract description 17
• 229920001577 copolymer Polymers 0.000 claims abstract description 13
• 230000003647 oxidation Effects 0.000 claims abstract description 13
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 12
• 239000001257 hydrogen Substances 0.000 claims abstract description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
• 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 12
• 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 11
• 239000000758 substrate Substances 0.000 claims abstract description 11
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 11
• 239000002952 polymeric resin Substances 0.000 claims abstract description 10
• 150000003839 salts Chemical class 0.000 claims abstract description 10
• 229920003002 synthetic resin Polymers 0.000 claims abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
• 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims abstract description 8
• 125000002252 acyl group Chemical group 0.000 claims abstract description 8
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 7
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 6
• 230000000996 additive effect Effects 0.000 claims abstract description 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 4
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 4
• 229920001059 synthetic polymer Polymers 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 28
• 229920005989 resin Polymers 0.000 claims description 21
• 239000011347 resin Substances 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 238000004806 packaging method and process Methods 0.000 claims description 15
• 235000013305 food Nutrition 0.000 claims description 11
• 150000003097 polyterpenes Chemical class 0.000 claims description 11
• 229940123973 Oxygen scavenger Drugs 0.000 claims description 8
• 239000000178 monomer Substances 0.000 claims description 8
• PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229910052802 copper Inorganic materials 0.000 claims description 5
• 239000000945 filler Substances 0.000 claims description 5
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 5
• 239000004793 Polystyrene Substances 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
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• 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
• XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 3
• 229940087305 limonene Drugs 0.000 claims description 3
• 229910052748 manganese Inorganic materials 0.000 claims description 3
• 229910052759 nickel Inorganic materials 0.000 claims description 3
• 230000003287 optical effect Effects 0.000 claims description 3
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• 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 2
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
• 229910052684 Cerium Inorganic materials 0.000 claims description 2
• 239000005062 Polybutadiene Substances 0.000 claims description 2
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 2
• 150000001298 alcohols Chemical class 0.000 claims description 2
• 239000002216 antistatic agent Substances 0.000 claims description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
• JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 2
• JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
• 239000004014 plasticizer Substances 0.000 claims description 2
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• 229920000728 polyester Polymers 0.000 claims description 2
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• 239000012744 reinforcing agent Substances 0.000 claims description 2
• 229940032094 squalane Drugs 0.000 claims description 2
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• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 229920002554 vinyl polymer Polymers 0.000 claims description 2
• HUGVCNLGXYJGAC-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 2-benzoylbenzoate Chemical compound O=C1C2=CC=CC=C2C(=O)N1OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 HUGVCNLGXYJGAC-UHFFFAOYSA-N 0.000 claims 1
• MMZCYVBYIOUFEO-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C(=O)C2=CC=CC=C2C1=O MMZCYVBYIOUFEO-UHFFFAOYSA-N 0.000 claims 1
• QJACGYUVHYUJHZ-UHFFFAOYSA-N 2-trityloxyisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QJACGYUVHYUJHZ-UHFFFAOYSA-N 0.000 claims 1
• 239000004604 Blowing Agent Substances 0.000 claims 1
• RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
• 229910000071 diazene Inorganic materials 0.000 claims 1
• 239000003381 stabilizer Substances 0.000 claims 1
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 21
• 230000000052 comparative effect Effects 0.000 description 20
• 230000004888 barrier function Effects 0.000 description 19
• 239000000047 product Substances 0.000 description 19
• 235000002639 sodium chloride Nutrition 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 229920001684 low density polyethylene Polymers 0.000 description 13
• 239000004702 low-density polyethylene Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000011521 glass Substances 0.000 description 12
• 238000000034 method Methods 0.000 description 12
• 229910001868 water Inorganic materials 0.000 description 12
• 229920000642 polymer Polymers 0.000 description 11
• 125000002947 alkylene group Chemical group 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 229910052742 iron Inorganic materials 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 9
• SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 description 9
• 239000005022 packaging material Substances 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• 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
• 150000003254 radicals Chemical class 0.000 description 8
• 239000007787 solid Substances 0.000 description 7
• 239000006096 absorbing agent Substances 0.000 description 6
• 150000003857 carboxamides Chemical class 0.000 description 6
• 150000007942 carboxylates Chemical class 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
• 150000002148 esters Chemical class 0.000 description 6
• 238000001125 extrusion Methods 0.000 description 6
• 229910001507 metal halide Inorganic materials 0.000 description 6
• 150000005309 metal halides Chemical class 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 238000000465 moulding Methods 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 125000004423 acyloxy group Chemical group 0.000 description 5
• 238000013459 approach Methods 0.000 description 5
• 239000012964 benzotriazole Substances 0.000 description 5
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-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
• 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 4
• KTWCUGUUDHJVIH-UHFFFAOYSA-N 2-hydroxybenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(O)C2=O)=O)=C3C2=CC=CC3=C1 KTWCUGUUDHJVIH-UHFFFAOYSA-N 0.000 description 4
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
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