BRPI0616728A2

BRPI0616728A2 - artigo de polìmero degradável

artigo de polìmero degradável Download PDF

Info

Publication number: BRPI0616728A2
Authority: BR; Brazil
Prior art keywords: formula; alkyl; substituted; unsubstituted; phenyl
Prior art date: 2005-09-07

Application number

BRPI0616728-4A

Other languages

English (en)

Portuguese (pt)

Inventor

Massimiliano Sala

Stefano Gardi

Gunther Schlingloff

Original Assignee

Ciba Sc Holding Ag

Priority date

2005-09-07

Filing date

2006-08-28

Publication date

2011-06-28

2006-08-28 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2011-06-28 Publication of BRPI0616728A2 publication Critical patent/BRPI0616728A2/pt

Links

229920006237 degradable polymer Polymers 0.000 title abstract 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 154
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 92
239000000203 mixture Substances 0.000 claims abstract description 91
229920000642 polymer Polymers 0.000 claims abstract description 84
229920001577 copolymer Polymers 0.000 claims abstract description 65
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
125000003342 alkenyl group Chemical group 0.000 claims abstract description 36
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 33
150000002431 hydrogen Chemical class 0.000 claims abstract description 30
125000002252 acyl group Chemical group 0.000 claims abstract description 26
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 25
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
229920000098 polyolefin Polymers 0.000 claims abstract description 18
229920001059 synthetic polymer Polymers 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
229920005615 natural polymer Polymers 0.000 claims abstract description 11
230000015556 catabolic process Effects 0.000 claims abstract description 9
238000006731 degradation reaction Methods 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000002619 bicyclic group Chemical group 0.000 claims abstract description 7
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
-1 tert-butyldiphenylsilanyl Chemical group 0.000 claims description 191
125000003118 aryl group Chemical group 0.000 claims description 42
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 29
125000004423 acyloxy group Chemical group 0.000 claims description 27
150000007942 carboxylates Chemical class 0.000 claims description 23
235000007586 terpenes Nutrition 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 19
239000004952 Polyamide Substances 0.000 claims description 19
229920002647 polyamide Polymers 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000004104 aryloxy group Chemical group 0.000 claims description 17
239000000654 additive Substances 0.000 claims description 13
125000003302 alkenyloxy group Chemical group 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
239000004743 Polypropylene Substances 0.000 claims description 11
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 10
150000004985 diamines Chemical class 0.000 claims description 10
150000003505 terpenes Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
229920000728 polyester Polymers 0.000 claims description 8
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 8
239000004698 Polyethylene Substances 0.000 claims description 7
239000000835 fiber Substances 0.000 claims description 7
229920000573 polyethylene Polymers 0.000 claims description 7
229920001155 polypropylene Polymers 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000010902 straw Substances 0.000 claims description 7
229910052723 transition metal Inorganic materials 0.000 claims description 7
150000003624 transition metals Chemical class 0.000 claims description 7
125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
229910052791 calcium Inorganic materials 0.000 claims description 6
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 description 6
230000000996 additive effect Effects 0.000 claims description 5
239000003963 antioxidant agent Substances 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
238000001125 extrusion Methods 0.000 claims description 5
239000000945 filler Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
239000005022 packaging material Substances 0.000 claims description 5
229920001169 thermoplastic Polymers 0.000 claims description 5
239000004416 thermosoftening plastic Substances 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 4
238000005266 casting Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000010410 layer Substances 0.000 claims description 4
238000004806 packaging method and process Methods 0.000 claims description 4
239000000049 pigment Substances 0.000 claims description 4
239000002356 single layer Substances 0.000 claims description 4
235000018290 Musa x paradisiaca Nutrition 0.000 claims description 3
229920002472 Starch Polymers 0.000 claims description 3
229920006328 Styrofoam Polymers 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
238000000071 blow moulding Methods 0.000 claims description 3
238000003490 calendering Methods 0.000 claims description 3
238000000748 compression moulding Methods 0.000 claims description 3
238000010096 film blowing Methods 0.000 claims description 3
238000001746 injection moulding Methods 0.000 claims description 3
229920005606 polypropylene copolymer Polymers 0.000 claims description 3
238000012545 processing Methods 0.000 claims description 3
239000012744 reinforcing agent Substances 0.000 claims description 3
238000009987 spinning Methods 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
239000008107 starch Substances 0.000 claims description 3
235000019698 starch Nutrition 0.000 claims description 3
239000008261 styrofoam Substances 0.000 claims description 3
238000003856 thermoforming Methods 0.000 claims description 3
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
150000004056 anthraquinones Chemical class 0.000 claims description 2
230000003078 antioxidant effect Effects 0.000 claims description 2
150000008366 benzophenones Chemical class 0.000 claims description 2
235000013361 beverage Nutrition 0.000 claims description 2
239000002537 cosmetic Substances 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
238000001175 rotational moulding Methods 0.000 claims description 2
229920003179 starch-based polymer Polymers 0.000 claims description 2
239000004628 starch-based polymer Substances 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
150000001491 aromatic compounds Chemical class 0.000 claims 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
240000005561 Musa balbisiana Species 0.000 claims 1
229910003849 O-Si Inorganic materials 0.000 claims 1
229910003872 O—Si Inorganic materials 0.000 claims 1
125000005431 alkyl carboxamide group Chemical group 0.000 claims 1
239000007799 cork Substances 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
238000000465 moulding Methods 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
239000007787 solid Substances 0.000 description 32
229910052757 nitrogen Inorganic materials 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000002844 melting Methods 0.000 description 24
230000008018 melting Effects 0.000 description 24
238000002360 preparation method Methods 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
229920000092 linear low density polyethylene Polymers 0.000 description 18
239000004707 linear low-density polyethylene Substances 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
229920005989 resin Polymers 0.000 description 17
239000011347 resin Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
239000005977 Ethylene Substances 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
239000000047 product Substances 0.000 description 15
150000003857 carboxamides Chemical class 0.000 description 13
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
229910052751 metal Inorganic materials 0.000 description 12
239000002184 metal Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 11
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 11
239000007983 Tris buffer Substances 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
150000002978 peroxides Chemical class 0.000 description 10
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
150000001993 dienes Chemical class 0.000 description 9
239000004417 polycarbonate Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
229920002554 vinyl polymer Polymers 0.000 description 9
GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 9
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 8
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
125000004356 hydroxy functional group Chemical group O* 0.000 description 8
229920001684 low density polyethylene Polymers 0.000 description 8
239000004702 low-density polyethylene Substances 0.000 description 8
239000000178 monomer Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
229920006324 polyoxymethylene Polymers 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
239000004721 Polyphenylene oxide Substances 0.000 description 7
125000002947 alkylene group Chemical group 0.000 description 7
XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
229920001903 high density polyethylene Polymers 0.000 description 7
239000004700 high-density polyethylene Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
229920002857 polybutadiene Polymers 0.000 description 7
150000003097 polyterpenes Chemical class 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
229920000915 polyvinyl chloride Polymers 0.000 description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000005062 Polybutadiene Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
229940022663 acetate Drugs 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 6
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
239000012964 benzotriazole Substances 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
229920001519 homopolymer Polymers 0.000 description 6
DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 6
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
229920001707 polybutylene terephthalate Polymers 0.000 description 6
239000004814 polyurethane Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
229940105296 zinc peroxide Drugs 0.000 description 6
WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000004343 Calcium peroxide Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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SPAGIJMPHSUYSE-UHFFFAOYSA-N Magnesium peroxide Chemical compound [Mg+2].[O-][O-] SPAGIJMPHSUYSE-UHFFFAOYSA-N 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
LHJQIRIGXXHNLA-UHFFFAOYSA-N calcium peroxide Chemical compound [Ca+2].[O-][O-] LHJQIRIGXXHNLA-UHFFFAOYSA-N 0.000 description 5
235000019402 calcium peroxide Nutrition 0.000 description 5
229920001971 elastomer Polymers 0.000 description 5
238000001914 filtration Methods 0.000 description 5
235000013312 flour Nutrition 0.000 description 5
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
229960004995 magnesium peroxide Drugs 0.000 description 5
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
229920006380 polyphenylene oxide Polymers 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
150000005846 sugar alcohols Polymers 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
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
ILJTZGSGCNDILQ-UHFFFAOYSA-N 2-hydroxy-1,3-dioxoisoindole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)N(O)C(=O)C2=C1 ILJTZGSGCNDILQ-UHFFFAOYSA-N 0.000 description 4
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 4
235000006708 antioxidants Nutrition 0.000 description 4
229930006722 beta-pinene Natural products 0.000 description 4
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
239000011575 calcium Substances 0.000 description 4
CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 4
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