CH621565A5 - Process for producing new polymers containing hydroquinone groups - Google Patents

Process for producing new polymers containing hydroquinone groups Download PDF

Info

Publication number: CH621565A5
Authority: CH; Switzerland
Prior art keywords: formula; tert; per mole; compound; hydrogen
Prior art date: 1975-02-24

Application number

CH218476A

Other languages

German (de)

English (en)

Inventor

James A Dale

Patricia C Wang

Ned M Weinshenker

Leonard A Bunes

Roman Davis

Original Assignee

Dynapol Corp

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.)

1975-02-24

Filing date

1976-02-23

Publication date

1981-02-13

1975-02-24 Priority claimed from US05/552,017 external-priority patent/US3996160A/en

1976-02-17 Priority claimed from US05/658,943 external-priority patent/US3996199A/en

1976-02-23 Application filed by Dynapol Corp filed Critical Dynapol Corp

1981-02-13 Publication of CH621565A5 publication Critical patent/CH621565A5/de

Links

229920000642 polymer Polymers 0.000 title claims description 37
238000000034 method Methods 0.000 title claims description 22
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 73
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 49
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 25
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 25
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 claims description 20
239000003054 catalyst Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 14
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 14
229910052782 aluminium Inorganic materials 0.000 claims description 13
239000004250 tert-Butylhydroquinone Substances 0.000 claims description 13
235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 13
238000005804 alkylation reaction Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
-1 tert-amyl Chemical group 0.000 claims description 9
230000029936 alkylation Effects 0.000 claims description 8
150000002989 phenols Chemical class 0.000 claims description 8
239000000376 reactant Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims 4
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
125000000732 arylene group Chemical group 0.000 claims 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
239000000047 product Substances 0.000 description 35
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 17
239000008096 xylene Substances 0.000 description 14
239000003963 antioxidant agent Substances 0.000 description 13
235000006708 antioxidants Nutrition 0.000 description 13
239000002904 solvent Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
229920002554 vinyl polymer Polymers 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000003078 antioxidant effect Effects 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
239000000126 substance Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000012476 oxidizable substance Substances 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
150000002978 peroxides Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229960003742 phenol Drugs 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000004448 titration Methods 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229940106691 bisphenol a Drugs 0.000 description 3
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
150000003738 xylenes Chemical class 0.000 description 3
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 2
VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 2
SGWZVZZVXOJRAQ-UHFFFAOYSA-N 2,6-Dimethyl-1,4-benzenediol Chemical compound CC1=CC(O)=CC(C)=C1O SGWZVZZVXOJRAQ-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
235000005979 Citrus limon Nutrition 0.000 description 2
244000131522 Citrus pyriformis Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229920005603 alternating copolymer Polymers 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
VJIDDJAKLVOBSE-UHFFFAOYSA-N ethylhydroquinone Natural products CCC1=CC(O)=CC=C1O VJIDDJAKLVOBSE-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
VJHGSLHHMIELQD-UHFFFAOYSA-N nona-1,8-diene Chemical compound C=CCCCCCC=C VJHGSLHHMIELQD-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
150000004707 phenolate Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
GCYUJISWSVALJD-UHFFFAOYSA-N 1,1-diethylcyclohexane Chemical compound CCC1(CC)CCCCC1 GCYUJISWSVALJD-UHFFFAOYSA-N 0.000 description 1
IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 1
AAJXNXUGVYIBAY-UHFFFAOYSA-N 1,4-bis(ethenyl)-2-methylbenzene Chemical compound CC1=CC(C=C)=CC=C1C=C AAJXNXUGVYIBAY-UHFFFAOYSA-N 0.000 description 1
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
GWYFZTJDIQALEB-UHFFFAOYSA-N 2-ethenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=C)=C1 GWYFZTJDIQALEB-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
VGTATGVAAOIEQC-UHFFFAOYSA-N 3,5-dimethylocta-1,7-diene Chemical compound C=CCC(C)CC(C)C=C VGTATGVAAOIEQC-UHFFFAOYSA-N 0.000 description 1
IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
AGZNHDUBGPTFIN-UHFFFAOYSA-N 3-ethylhexa-1,4-diene Chemical compound CCC(C=C)C=CC AGZNHDUBGPTFIN-UHFFFAOYSA-N 0.000 description 1
CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
XYWCSESPHBTCSP-UHFFFAOYSA-N 3-tert-butyl-4-(1-phenylethyl)phenol Chemical compound C=1C=C(O)C=C(C(C)(C)C)C=1C(C)C1=CC=CC=C1 XYWCSESPHBTCSP-UHFFFAOYSA-N 0.000 description 1
CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
JKINPMFPGULFQY-UHFFFAOYSA-N 4-tert-butyl-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C(C)(C)C JKINPMFPGULFQY-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GGISZLOBBISXOZ-UHFFFAOYSA-N acetic acid;chloroform Chemical compound CC(O)=O.ClC(Cl)Cl GGISZLOBBISXOZ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
ODJYLDXOPCUNCR-UHFFFAOYSA-K aluminum;2-carboxy-4-hydroxyphenolate Chemical compound [Al+3].OC(=O)C1=CC(O)=CC=C1[O-].OC(=O)C1=CC(O)=CC=C1[O-].OC(=O)C1=CC(O)=CC=C1[O-] ODJYLDXOPCUNCR-UHFFFAOYSA-K 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
PUKPNLXRVXJPRD-UHFFFAOYSA-N benzene-1,4-diol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.OC1=CC=C(O)C=C1 PUKPNLXRVXJPRD-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000895 extractive distillation Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000005454 flavour additive Substances 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000005417 food ingredient Substances 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
230000001151 other effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000036284 oxygen consumption Effects 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
150000005199 trimethylbenzenes Chemical class 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Food Science & Technology (AREA)
Zoology (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CH218476A 1975-02-24 1976-02-23 Process for producing new polymers containing hydroquinone groups CH621565A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/552,017 US3996160A (en)	1975-02-24	1975-02-24	Hydroquinonoid ortho-alkylation polymers and the process of their production
US05/658,943 US3996199A (en)	1976-02-17	1976-02-17	Oil soluble polymeric antioxidant prepared by condensation of divinylbenzene, hydroxyanisole, tertiary butyl hydroquinone, tertiary butyl phenol and bisphenol A under ortho alkylation conditions

Publications (1)

Publication Number	Publication Date
CH621565A5 true CH621565A5 (en)	1981-02-13

Family

ID=27069932

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH218476A CH621565A5 (en)	1975-02-24	1976-02-23	Process for producing new polymers containing hydroquinone groups

Country Status (5)

Country	Link
BE (1)	BE838834A (fr)
CH (1)	CH621565A5 (fr)
FR (1)	FR2301550A1 (fr)
GB (1)	GB1498756A (fr)
IT (1)	IT1061218B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3862376A1 (fr)	2020-02-07	2021-08-11	Rain Carbon Germany GmbH	Agent poisseux pour composés élastomères

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2665312A (en) *	1951-08-03	1954-01-05	Dow Chemical Co	Stabilized polyglycol compositions
US2832808A (en) *	1955-12-08	1958-04-29	Monsanto Chemicals	Alkylation of hydroquinone
DE1495710A1 (de) *	1963-01-23	1969-08-14	Hoechst Ag	Verfahren zur Herstellung flexibler Harze
NL6404699A (fr) *	1963-04-29	1964-10-30
US3644533A (en) *	1969-12-29	1972-02-22	Hooker Chemical Corp	Phenols and phenolic resins
US3644537A (en) *	1969-12-29	1972-02-22	Hooker Chemical Corp	Phenols and phenolic resins

1976
- 1976-02-23 CH CH218476A patent/CH621565A5/de not_active IP Right Cessation
- 1976-02-23 IT IT48238/76A patent/IT1061218B/it active
- 1976-02-23 GB GB7086/76A patent/GB1498756A/en not_active Expired
- 1976-02-23 FR FR7604892A patent/FR2301550A1/fr active Granted
- 1976-02-23 BE BE164544A patent/BE838834A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2301550A1 (fr)	1976-09-17
BE838834A (fr)	1976-06-16
IT1061218B (it)	1983-02-28
FR2301550B1 (fr)	1979-07-20
GB1498756A (en)	1978-01-25

Legal Events

Date	Code	Title	Description
1988-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2607431C2 (de)	1986-02-13	Hydrochinongruppen enthaltendes Polymer und Verfahren zu seiner Herstellung
US3996198A (en)	1976-12-07	One step preparation of linear antioxidant phenolic polymers involving use of impure diolefin feedstock and aluminum catalyst under ortho alkylation conditions
DE1645470A1 (de)	1970-05-21	Verfahren zur Herstellung von substituierten Phenolen
DE2746547C2 (fr)	1988-10-27
DE882987C (de)	1953-07-13	Verfahren zur Herstellung von tert.-Alkylbenzolcarbonsaeuren
DE1495985B1 (de)	1971-06-09	Verfahren zur herstellung von polyaddukten
DE1150206B (de)	1963-06-12	Verfahren zur Herstellung von Polymerisaten aus Olefinoxyden
DE2139564B2 (de)	1980-10-30	Verfahren zur Herstellung von 33'33'-Tetra-isopropyl-4,4'-hydroxydiphenyl
DE69902566T2 (de)	2002-12-19	Verfahren zur Herstellung von modifizierten Terpen-Phenol Harzen
DE674984C (de)	1939-04-26	Verfahren zur Herstellung von Reaktionsprodukten des Styrols
CH621565A5 (en)	1981-02-13	Process for producing new polymers containing hydroquinone groups
DE2141186C3 (de)	1981-04-02	Verfahren zur Herstellung primärer oder sekundärer, ungesättigter Ca u. C&darr;11&darr;- Alkohole
EP0363659A1 (fr)	1990-04-18	Utilisation de dérivés du stilbène dans la polymérisation anionique
DE1937384A1 (de)	1971-02-11	Stabilisatoren
DE2452912A1 (de)	1975-05-15	Verfahren zur herstellung von ungesaettigten dimeren von alpha-methylstyrolen
DE3887859T2 (de)	1994-05-19	Zersetzung von Dihydroperoxyd zu Resorcin.
DE2133584A1 (de)	1972-02-03	Kohlenwasserstoffe
DE1179768B (de)	1964-10-15	Fluessiger bzw. fluessig-viskoser bis fester Brennstoff fuer fluessige oder feste Raketen- und/oder Duesentreibstoffe
DE1594487C3 (de)	1975-08-07	Diphenoxydiphenyle, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE2135484A1 (de)	1972-11-23	Phenolausgangsverbindungen und Verfahren zu deren Herstellung
DE1092027B (de)	1960-11-03	Verfahren zur Herstellung von antioxydierend wirkenden Bis-(hydroxy-benzyl)-alkylbenzolen
DE69701143T2 (de)	2000-09-28	Polymere mit dihydroxygruppen
DE1543512C3 (de)	1979-11-15	Verfahren zur Aralkylierung von Phenolen mit Styrol oder a-MethylstyroI
DE652551C (de)	1937-11-02	Verfahren zur Herstellung von Alkylresorcinen
DE3783431T2 (de)	1993-05-06	Herstellungsverfahren von 2,6-diacetoxynaphthalen.