CA2019110C - Compositions de polyacetal contenant un agent stabilisant polymerique non fusible, ameliore avec une petite quantite d'au moins un costabilisant fusible et d'au moins un antioxydant primaire - Google Patents

Compositions de polyacetal contenant un agent stabilisant polymerique non fusible, ameliore avec une petite quantite d'au moins un costabilisant fusible et d'au moins un antioxydant primaire Download PDF

Info

Publication number: CA2019110C
Authority: CA; Canada
Prior art keywords: stabilizer; meltable; composition; hydroxy; polymer
Prior art date: 1989-06-15
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.): Expired - Fee Related

Application number

CA 2019110

Other languages

English (en)

Other versions

CA2019110A1 (fr

Inventor

Richard A. Hayes

Leonard E.R. Kosinski

Mark E. Wagman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1989-06-15

Filing date

1990-06-15

Publication date

2001-05-29

1990-06-15 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1990-12-15 Publication of CA2019110A1 publication Critical patent/CA2019110A1/fr

2001-05-29 Application granted granted Critical

2001-05-29 Publication of CA2019110C publication Critical patent/CA2019110C/fr

2010-06-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003381 stabilizer Substances 0.000 title claims abstract description 210
229920000642 polymer Polymers 0.000 title claims abstract description 187
229920006324 polyoxymethylene Polymers 0.000 title claims abstract description 114
229930182556 Polyacetal Natural products 0.000 title claims abstract description 109
239000000203 mixture Substances 0.000 title claims abstract description 108
239000003963 antioxidant agent Substances 0.000 title claims abstract description 43
230000003078 antioxidant effect Effects 0.000 title claims abstract description 34
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 166
239000002245 particle Substances 0.000 claims description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
-1 poly(vinyl alcohol) Polymers 0.000 claims description 38
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
229920001577 copolymer Polymers 0.000 claims description 21
229920001223 polyethylene glycol Polymers 0.000 claims description 15
239000004952 Polyamide Substances 0.000 claims description 10
229920002647 polyamide Polymers 0.000 claims description 10
230000002378 acidificating effect Effects 0.000 claims description 9
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 8
150000001408 amides Chemical group 0.000 claims description 8
239000000463 material Substances 0.000 claims description 8
239000002530 phenolic antioxidant Substances 0.000 claims description 8
229920001897 terpolymer Polymers 0.000 claims description 7
229920002292 Nylon 6 Polymers 0.000 claims description 6
229920002302 Nylon 6,6 Polymers 0.000 claims description 6
239000002202 Polyethylene glycol Substances 0.000 claims description 6
YWJUZWOHLHBWQY-UHFFFAOYSA-N decanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCC(O)=O YWJUZWOHLHBWQY-UHFFFAOYSA-N 0.000 claims description 6
229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
239000004810 polytetrafluoroethylene Substances 0.000 claims description 6
239000004698 Polyethylene Substances 0.000 claims description 5
229920000573 polyethylene Polymers 0.000 claims description 5
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical group CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 claims description 4
235000013877 carbamide Nutrition 0.000 claims description 4
239000000049 pigment Substances 0.000 claims description 4
150000003673 urethanes Chemical class 0.000 claims description 4
239000003086 colorant Substances 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
239000002667 nucleating agent Substances 0.000 claims description 3
229920002401 polyacrylamide Polymers 0.000 claims description 3
239000000843 powder Substances 0.000 claims description 3
150000003336 secondary aromatic amines Chemical class 0.000 claims description 3
229920002545 silicone oil Polymers 0.000 claims description 3
150000003672 ureas Chemical class 0.000 claims description 3
ROHFBIREHKPELA-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O ROHFBIREHKPELA-UHFFFAOYSA-N 0.000 claims description 2
WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
229920000193 polymethacrylate Polymers 0.000 claims description 2
229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
229920001169 thermoplastic Polymers 0.000 claims description 2
239000004416 thermosoftening plastic Substances 0.000 claims description 2
239000012745 toughening agent Substances 0.000 claims description 2
239000012963 UV stabilizer Substances 0.000 claims 1
229920002959 polymer blend Polymers 0.000 claims 1
239000012744 reinforcing agent Substances 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
230000007774 longterm Effects 0.000 abstract description 13
238000012545 processing Methods 0.000 abstract description 13
239000003017 thermal stabilizer Substances 0.000 abstract description 10
230000000704 physical effect Effects 0.000 abstract description 8
230000014759 maintenance of location Effects 0.000 abstract description 5
238000000465 moulding Methods 0.000 abstract description 3
238000010348 incorporation Methods 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
238000006116 polymerization reaction Methods 0.000 description 32
238000000034 method Methods 0.000 description 26
239000000178 monomer Substances 0.000 description 25
239000002270 dispersing agent Substances 0.000 description 20
150000001875 compounds Chemical class 0.000 description 17
239000000243 solution Substances 0.000 description 17
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
229920001519 homopolymer Polymers 0.000 description 12
239000000155 melt Substances 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
239000003995 emulsifying agent Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000004356 hydroxy functional group Chemical group O* 0.000 description 9
238000005259 measurement Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000012535 impurity Substances 0.000 description 8
238000010128 melt processing Methods 0.000 description 8
238000002156 mixing Methods 0.000 description 8
239000000654 additive Substances 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
238000005406 washing Methods 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000001746 injection moulding Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000000113 differential scanning calorimetry Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000003999 initiator Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
230000003993 interaction Effects 0.000 description 4
238000010526 radical polymerization reaction Methods 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
230000005540 biological transmission Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
229910003460 diamond Inorganic materials 0.000 description 3
239000010432 diamond Substances 0.000 description 3
238000012674 dispersion polymerization Methods 0.000 description 3
238000001125 extrusion Methods 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
239000003607 modifier Substances 0.000 description 3
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
229940117969 neopentyl glycol Drugs 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
230000000087 stabilizing effect Effects 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
238000004627 transmission electron microscopy Methods 0.000 description 3
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
239000004677 Nylon Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000032683 aging Effects 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
238000000071 blow moulding Methods 0.000 description 2
239000001273 butane Substances 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000013329 compounding Methods 0.000 description 2
238000000748 compression moulding Methods 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
230000007423 decrease Effects 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
125000004464 hydroxyphenyl group Chemical group 0.000 description 2
230000006872 improvement Effects 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
238000002074 melt spinning Methods 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
229920001778 nylon Polymers 0.000 description 2
125000005702 oxyalkylene group Chemical group 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001175 rotational moulding Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000003856 thermoforming Methods 0.000 description 2
229940113165 trimethylolpropane Drugs 0.000 description 2
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical class CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
SNJAYFIFURSZQU-UHFFFAOYSA-N (3-amino-1h-1,2,4-triazol-5-yl)-(2-hydroxyphenyl)methanone Chemical compound N1C(N)=NC(C(=O)C=2C(=CC=CC=2)O)=N1 SNJAYFIFURSZQU-UHFFFAOYSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
BGSBXDJLUNXANY-UHFFFAOYSA-N 1-butylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCC BGSBXDJLUNXANY-UHFFFAOYSA-N 0.000 description 1
VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
WGCOJSGVXOMWKK-UHFFFAOYSA-N 10-(2,2-diphenylhydrazinyl)-10-oxodecanoic acid Chemical compound C1(=CC=CC=C1)N(NC(CCCCCCCCC(=O)O)=O)C1=CC=CC=C1 WGCOJSGVXOMWKK-UHFFFAOYSA-N 0.000 description 1
BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 description 1
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
QHPKIUDQDCWRKO-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 QHPKIUDQDCWRKO-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
HBXWTSGRLITCMK-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;propane-1,2-diol Chemical compound CC(O)CO.OCCOCCO HBXWTSGRLITCMK-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
UCNKQFJKNGKQTI-UHFFFAOYSA-N 2-[[2-hydroxy-5-methyl-3-(4-methylcyclohexyl)phenyl]methyl]-4-methyl-6-(4-methylcyclohexyl)phenol Chemical compound C1CC(C)CCC1C1=CC(C)=CC(CC=2C(=C(C3CCC(C)CC3)C=C(C)C=2)O)=C1O UCNKQFJKNGKQTI-UHFFFAOYSA-N 0.000 description 1
OMCYEZUIYGPHDJ-UHFFFAOYSA-N 2-hydroxy-N-[(2-hydroxyphenyl)methylideneamino]benzamide Chemical compound OC1=CC=CC=C1C=NNC(=O)C1=CC=CC=C1O OMCYEZUIYGPHDJ-UHFFFAOYSA-N 0.000 description 1
ZMNKLZZCQGIIOV-UHFFFAOYSA-N 2-n,2-n'-bis(2-hydroxybenzoyl)ethanedihydrazide Chemical compound C=1C=CC=C(O)C=1C(=O)N(C(=O)C(=O)NN)NC(=O)C1=CC=CC=C1O ZMNKLZZCQGIIOV-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 1
PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
LZAIWKMQABZIDI-UHFFFAOYSA-N 4-methyl-2,6-dioctadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C)=CC(CCCCCCCCCCCCCCCCCC)=C1O LZAIWKMQABZIDI-UHFFFAOYSA-N 0.000 description 1
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
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RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000010030 laminating Methods 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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230000004048 modification Effects 0.000 description 1
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FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000004989 p-phenylenediamines Chemical class 0.000 description 1
238000010422 painting Methods 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
238000007747 plating Methods 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
238000012643 polycondensation polymerization Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920003225 polyurethane elastomer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000001454 recorded image Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

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Compositions Of Macromolecular Compounds (AREA)

CA 2019110 1989-06-15 1990-06-15 Compositions de polyacetal contenant un agent stabilisant polymerique non fusible, ameliore avec une petite quantite d'au moins un costabilisant fusible et d'au moins un antioxydant primaire Expired - Fee Related CA2019110C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US36655889A	1989-06-15	1989-06-15
US366,558		1989-06-15

Publications (2)

Publication Number	Publication Date
CA2019110A1 CA2019110A1 (fr)	1990-12-15
CA2019110C true CA2019110C (fr)	2001-05-29

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ID=23443533

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Application Number	Title	Priority Date	Filing Date
CA 2019110 Expired - Fee Related CA2019110C (fr)	1989-06-15	1990-06-15	Compositions de polyacetal contenant un agent stabilisant polymerique non fusible, ameliore avec une petite quantite d'au moins un costabilisant fusible et d'au moins un antioxydant primaire

Country Status (1)

Country	Link
CA (1)	CA2019110C (fr)

1990
- 1990-06-15 CA CA 2019110 patent/CA2019110C/fr not_active Expired - Fee Related

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Publication number	Publication date
CA2019110A1 (fr)	1990-12-15

Legal Events

Date	Code	Title	Description
1997-05-15	EEER	Examination request
2003-06-16	MKLA	Lapsed

Publication	Publication Date	Title
US5011890A (en)	1991-04-30	Polyacetal resins containing non-meltable polymer stabilizers
US5063263A (en)	1991-11-05	Polyacetal compositions containing a non-meltable polymer stabilizer improved with a minor amount of at least one meltable co-stabilizer and at least one primary antioxidant
KR960004480B1 (ko)	1996-04-06	안정화된 폴리아세탈 조성물
KR950006810B1 (ko)	1995-06-22	안정화된 폴리아세탈 조성물
US6147146A (en)	2000-11-14	Resin composition
KR960013124B1 (ko)	1996-09-30	비용융성 중합체 안정제를 함유하는 폴리아세탈 조성물 및 그의 제조 방법
US4972014A (en)	1990-11-20	Polyacetal compositions containing a non-meltable polymer stabilizer improved with at least one amide-containing phenolic antioxidant
EP0477286B1 (fr)	1996-08-21	Compositions de polyacetal stabilisees
JP3130121B2 (ja)	2001-01-31	安定化されたポリアセタール組成物
WO1991018051A1 (fr)	1991-11-28	Melanges de polyoxymethylene thermostables
CA2019110C (fr)	2001-05-29	Compositions de polyacetal contenant un agent stabilisant polymerique non fusible, ameliore avec une petite quantite d'au moins un costabilisant fusible et d'au moins un antioxydant primaire
KR20210141958A (ko)	2021-11-23	폴리옥시메틸렌 조성물
EP0554392A1 (fr)	1993-08-11	Compositions a base de polyoxymethylene contenant du polyethylene lineaire de faible densite.
DE69623945T2 (de)	2003-05-22	Polyketonpolymer-zusammensetzung
DE69616538T2 (de)	2002-05-08	Polyketonpolymer-zusammensetzung
CA1293076C (fr)	1991-12-10	Compositions stabilisees de polyacetal
JPH07126481A (ja)	1995-05-16	耐候性ポリアセタール樹脂組成物
JPH07309994A (ja)	1995-11-28	ポリオキシメチレン樹脂組成物
JPH04222852A (ja)	1992-08-12	トリアジン系遮蔽アミン光安定剤を含有するポリアセタール組成物