JPS61140589A

JPS61140589A - 耐加水分解性の改良されたペンタエリトリト−ル−スピロ−ビス−ホスフアイト組成物及び該組成物を含む組成物

耐加水分解性の改良されたペンタエリトリト−ル−スピロ−ビス−ホスフアイト組成物及び該組成物を含む組成物

Info

Publication number: JPS61140589A
Authority: JP; Japan
Prior art keywords: carbon atoms; phosphite; pentaerythritol; bis; spiro
Prior art date: 1984-12-10
Legal status : Granted

Application number

JP26062884A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0447679B2 (enExample

Inventor

マイクル・エイチ・フイツシユ

ジアミー・ブラム

ローレンス・アール・ブレツカー

Current Assignee

Argus Chemical Corp

Original Assignee

Argus Chemical Corp

Priority date

1984-12-10

Filing date

1984-12-10

Publication date

1986-06-27

1984-12-10 Application filed by Argus Chemical Corp filed Critical Argus Chemical Corp

1984-12-10 Priority to JP26062884A priority Critical patent/JPS61140589A/ja

1986-06-27 Publication of JPS61140589A publication Critical patent/JPS61140589A/ja

1992-08-04 Publication of JPH0447679B2 publication Critical patent/JPH0447679B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 76
230000007062 hydrolysis Effects 0.000 title claims description 17
238000006460 hydrolysis reaction Methods 0.000 title claims description 17
-1 hydroxyethyl group Chemical group 0.000 claims description 59
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 40
239000003381 stabilizer Substances 0.000 claims description 35
150000001412 amines Chemical class 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 26
229920000915 polyvinyl chloride Polymers 0.000 claims description 21
239000004800 polyvinyl chloride Substances 0.000 claims description 21
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
229920000098 polyolefin Polymers 0.000 claims description 15
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
239000004743 Polypropylene Substances 0.000 claims description 12
229920001155 polypropylene Polymers 0.000 claims description 12
229920001577 copolymer Polymers 0.000 claims description 11
229920005989 resin Polymers 0.000 claims description 11
239000011347 resin Substances 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 8
230000006866 deterioration Effects 0.000 claims description 8
239000011342 resin composition Substances 0.000 claims description 8
229920003002 synthetic resin Polymers 0.000 claims description 7
239000000057 synthetic resin Substances 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
239000004698 Polyethylene Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
229920000573 polyethylene Polymers 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229920001519 homopolymer Polymers 0.000 claims description 4
239000004793 Polystyrene Substances 0.000 claims description 3
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
229920002223 polystyrene Polymers 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000003078 antioxidant effect Effects 0.000 claims 1
239000004711 α-olefin Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229920000642 polymer Polymers 0.000 description 18
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 7
239000000654 additive Substances 0.000 description 7
238000002156 mixing Methods 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 6
238000004811 liquid chromatography Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 5
238000002845 discoloration Methods 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
230000003301 hydrolyzing effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
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230000000087 stabilizing effect Effects 0.000 description 5
238000004383 yellowing Methods 0.000 description 5
239000004593 Epoxy Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
150000008301 phosphite esters Chemical class 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007792 addition Methods 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000000465 moulding Methods 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
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229920000515 polycarbonate Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000011343 solid material Substances 0.000 description 3
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920001059 synthetic polymer Polymers 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
QJARJRBYFJRFGX-UHFFFAOYSA-N 1-aminohexadecan-2-ol Chemical compound CCCCCCCCCCCCCCC(O)CN QJARJRBYFJRFGX-UHFFFAOYSA-N 0.000 description 2
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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239000004952 Polyamide Substances 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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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 2
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230000032683 aging Effects 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000002216 antistatic agent Substances 0.000 description 2
125000001204 arachidyl 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])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 2
125000002511 behenyl 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])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 2
230000015572 biosynthetic process Effects 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
238000003490 calendering Methods 0.000 description 2
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238000004587 chromatography analysis Methods 0.000 description 2
VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 2
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239000012760 heat stabilizer Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
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238000004898 kneading Methods 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
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238000003760 magnetic stirring Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000001421 myristyl 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])C([H])([H])[H] 0.000 description 2
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229910017464 nitrogen compound Inorganic materials 0.000 description 2
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125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002530 phenolic antioxidant Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
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230000000704 physical effect Effects 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004448 titration Methods 0.000 description 2
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HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
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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 description 1
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LGKVAJZZWOFYSZ-UHFFFAOYSA-N 1,1-bis(2-tert-butyl-4-methylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C)C(C)(C)C LGKVAJZZWOFYSZ-UHFFFAOYSA-N 0.000 description 1
GHJOEPMHSNXADF-UHFFFAOYSA-N 1-aminoicosan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCC(O)CN GHJOEPMHSNXADF-UHFFFAOYSA-N 0.000 description 1
BTHTUCFRGFQVAM-UHFFFAOYSA-N 1-aminotetracosan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(O)CN BTHTUCFRGFQVAM-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
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YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical group CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
GUYSJSJQKCZUPG-UHFFFAOYSA-N 2-octadecylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCC(CN)CCCCCCCCCCCCCCCCCC GUYSJSJQKCZUPG-UHFFFAOYSA-N 0.000 description 1
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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