TWI322811B

TWI322811B - Amorphous solid modification of bis(2,4-dicumylphenyl)pentaerythritol diphosphite

Amorphous solid modification of bis(2,4-dicumylphenyl)pentaerythritol diphosphite Download PDF

Info

Publication number: TWI322811B
Authority: TW; Taiwan
Prior art keywords: bis; butyl; acid; ethylene; hydroxy
Prior art date: 2002-05-30

Application number

TW092114358A

Other languages

English (en)

Chinese (zh)

Other versions

TW200408646A (en

Inventor

Daniel Thibaut

Original Assignee

Ciba Sc Holding Ag

Priority date

2002-05-30

Filing date

2003-05-28

Publication date

2010-04-01

2003-05-28 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2004-06-01 Publication of TW200408646A publication Critical patent/TW200408646A/zh

2010-04-01 Application granted granted Critical

2010-04-01 Publication of TWI322811B publication Critical patent/TWI322811B/zh

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239000007787 solid Substances 0.000 title claims abstract description 24
WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 title claims abstract description 10
230000004048 modification Effects 0.000 title abstract description 12
238000012986 modification Methods 0.000 title abstract description 12
239000011368 organic material Substances 0.000 claims abstract description 17
239000000203 mixture Substances 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 11
239000000654 additive Substances 0.000 claims description 10
238000012545 processing Methods 0.000 claims description 10
239000003381 stabilizer Substances 0.000 claims description 10
239000000155 melt Substances 0.000 claims description 9
239000012768 molten material Substances 0.000 claims description 8
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 claims description 6
238000002844 melting Methods 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 6
MPTISGUJJWJZRR-UHFFFAOYSA-N 1,1-bis[2,4-bis(2-phenylpropan-2-yl)phenyl]-2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C1=CC=CC=C1)C(C)(C)C1=CC=CC=C1 MPTISGUJJWJZRR-UHFFFAOYSA-N 0.000 claims description 5
239000004305 biphenyl Substances 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
238000001816 cooling Methods 0.000 claims description 4
239000004611 light stabiliser Substances 0.000 claims description 3
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
229920001059 synthetic polymer Polymers 0.000 claims description 3
239000002530 phenolic antioxidant Substances 0.000 claims description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
230000015556 catabolic process Effects 0.000 abstract description 7
238000006731 degradation reaction Methods 0.000 abstract description 7
230000000087 stabilizing effect Effects 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
230000001590 oxidative effect Effects 0.000 abstract 1
-1 hydrazine compound Chemical class 0.000 description 109
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OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 31
229920000642 polymer Polymers 0.000 description 31
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 27
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150000002148 esters Chemical class 0.000 description 21
239000000052 vinegar Substances 0.000 description 20
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
239000000126 substance Substances 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 15
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
150000001412 amines Chemical class 0.000 description 14
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 13
239000012964 benzotriazole Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 12
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KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
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NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
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238000002360 preparation method Methods 0.000 description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
241000208340 Araliaceae Species 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 6
235000003140 Panax quinquefolius Nutrition 0.000 description 6
239000005062 Polybutadiene Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000000113 differential scanning calorimetry Methods 0.000 description 6
235000008434 ginseng Nutrition 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000178 monomer Substances 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
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239000004417 polycarbonate Substances 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
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229920001169 thermoplastic Polymers 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
229920001519 homopolymer Polymers 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229920001684 low density polyethylene Polymers 0.000 description 5
239000004702 low-density polyethylene Substances 0.000 description 5
239000000314 lubricant Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
229920000098 polyolefin Polymers 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
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ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 4
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KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
238000007792 addition Methods 0.000 description 4
230000000996 additive effect Effects 0.000 description 4
229910052797 bismuth Inorganic materials 0.000 description 4
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
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 4
239000000806 elastomer Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
229920000092 linear low density polyethylene Polymers 0.000 description 4
239000004707 linear low-density polyethylene Substances 0.000 description 4
238000005259 measurement Methods 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229920000620 organic polymer Polymers 0.000 description 4
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150000003839 salts Chemical class 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
229920001897 terpolymer Polymers 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
CYHYIIFODCKQNP-UHFFFAOYSA-N 5,7-ditert-butyl-3-(3,4-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound C1=C(C)C(C)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CYHYIIFODCKQNP-UHFFFAOYSA-N 0.000 description 3
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BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
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