CH585685A5 - Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde - Google Patents

Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde

Info

Publication number: CH585685A5
Authority: CH; Switzerland
Prior art keywords: tert; butyl; sep; alkyl; formula
Prior art date: 1973-07-20

Application number

CH1065073A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1973-07-20

Filing date

1973-07-20

Publication date

1977-03-15

1973-07-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-07-20 Priority to CH1065073A priority Critical patent/CH585685A5/de

1974-06-06 Priority to SE7407449A priority patent/SE7407449L/xx

1974-07-10 Priority to NL7409342A priority patent/NL7409342A/xx

1974-07-10 Priority to DE19742433050 priority patent/DE2433050C2/de

1974-07-17 Priority to GB3163874A priority patent/GB1455766A/en

1974-07-17 Priority to CA74204919A priority patent/CA1048529A/fr

1974-07-18 Priority to BR595474A priority patent/BR7405954D0/pt

1974-07-18 Priority to AU71378/74A priority patent/AU7137874A/en

1974-07-18 Priority to LU70563A priority patent/LU70563A1/xx

1974-07-18 Priority to SU742046325A priority patent/SU657741A3/ru

1974-07-19 Priority to IT2538674A priority patent/IT1017311B/it

1974-07-19 Priority to AT600874A priority patent/AT336575B/de

1974-07-19 Priority to ES428400A priority patent/ES428400A1/es

1974-07-19 Priority to BE146718A priority patent/BE817837A/fr

1974-07-19 Priority to FR7425178A priority patent/FR2237870B1/fr

1974-07-19 Priority to DK392774A priority patent/DK392774A/da

1974-07-19 Priority to JP8314774A priority patent/JPS5044182A/ja

1974-10-15 Priority to JP11858274A priority patent/JPS5111726A/ja

1977-03-15 Publication of CH585685A5 publication Critical patent/CH585685A5/de

Links

125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims description 3
239000000463 material Substances 0.000 title abstract description 5
239000003963 antioxidant agent Substances 0.000 title abstract description 3
MRVHGCMXWNDJBQ-UHFFFAOYSA-N benzyl carbamodithioate Chemical compound NC(=S)SCC1=CC=CC=C1 MRVHGCMXWNDJBQ-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
-1 phenol aldehydes Chemical class 0.000 claims description 49
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
239000002585 base Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 11
230000008569 process Effects 0.000 claims description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 10
229920000642 polymer Polymers 0.000 abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
150000001298 alcohols Chemical class 0.000 abstract description 4
150000001241 acetals Chemical class 0.000 abstract description 2
239000002253 acid Substances 0.000 abstract description 2
150000007513 acids Chemical class 0.000 abstract description 2
150000001408 amides Chemical class 0.000 abstract description 2
229930195733 hydrocarbon Natural products 0.000 abstract description 2
150000002430 hydrocarbons Chemical class 0.000 abstract description 2
239000002480 mineral oil Substances 0.000 abstract description 2
125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
239000011368 organic material Substances 0.000 abstract 1
229920002994 synthetic fiber Polymers 0.000 abstract 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
150000003673 urethanes Chemical class 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 12
229960004592 isopropanol Drugs 0.000 description 12
150000002148 esters Chemical group 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229920001577 copolymer Polymers 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-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
239000004743 Polypropylene Substances 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
229920001155 polypropylene Polymers 0.000 description 6
239000000758 substrate Substances 0.000 description 6
229920000877 Melamine resin Polymers 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000000155 melt Substances 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
XGWATTXMMMANFJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2,2-dimethylpropanal Chemical compound CC(C)(C)C1=CC(CC(C)(C)C=O)=CC(C(C)(C)C)=C1O XGWATTXMMMANFJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001125 extrusion Methods 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-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
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
229920002292 Nylon 6 Polymers 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
229920002367 Polyisobutene Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
229920006324 polyoxymethylene Polymers 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
YONUDXNHWDBVCN-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YONUDXNHWDBVCN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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 2
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 2
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 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 description 2
RYYPXOTXKAHJAL-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)-2,2-dimethylpropanal Chemical compound CC1=CC(CC(C)(C)C=O)=CC(C(C)(C)C)=C1O RYYPXOTXKAHJAL-UHFFFAOYSA-N 0.000 description 2
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
FHDXHBOQSPIKCY-UHFFFAOYSA-N CC(C)(C)C(C=C(CC(C)(C)C=O)C(C)=C1C)=C1O Chemical compound CC(C)(C)C(C=C(CC(C)(C)C=O)C(C)=C1C)=C1O FHDXHBOQSPIKCY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 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
KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000001099 ammonium carbonate Substances 0.000 description 2
235000012501 ammonium carbonate Nutrition 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 2
229950004394 ditiocarb Drugs 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000003063 flame retardant Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000003446 ligand Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920002866 paraformaldehyde Polymers 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000005060 rubber Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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
LUUMBHMWFNNZPH-UHFFFAOYSA-N tris(3,5-ditert-butyl-4-hydroxyphenyl) phosphite Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(OP(OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)OC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 LUUMBHMWFNNZPH-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
239000001993 wax Substances 0.000 description 2
YEYCMBWKTZNPDH-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC=CC=C1 YEYCMBWKTZNPDH-UHFFFAOYSA-N 0.000 description 1
JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 1
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230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
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 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl 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])[H] 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/46—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing hydroxy groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1065073A 1973-07-20 1973-07-20 Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde CH585685A5 (en)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
CH1065073A CH585685A5 (en)	1973-07-20	1973-07-20	Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde
SE7407449A SE7407449L (fr)	1973-07-20	1974-06-06
NL7409342A NL7409342A (nl)	1973-07-20	1974-07-10	Nieuwe fenolaldehyden.
DE19742433050 DE2433050C2 (de)	1973-07-20	1974-07-10	Phenolaldehyde, Verfahren zu ihrer Herstellung und Mittel zur Stabilisierung organischer Substrate
GB3163874A GB1455766A (en)	1973-07-20	1974-07-17	Pheno aldehydes
CA74204919A CA1048529A (fr)	1973-07-20	1974-07-17	Phenolaldehydes antioxydants
BR595474A BR7405954D0 (pt)	1973-07-20	1974-07-18	Processo para a preparacao de aldeidos fenolicos e composicoes de substancias a base destes
AU71378/74A AU7137874A (en)	1973-07-20	1974-07-18	Phenolaldehydes
LU70563A LU70563A1 (fr)	1973-07-20	1974-07-18
SU742046325A SU657741A3 (ru)	1973-07-20	1974-07-18	Способ получени фенолальдегидов
IT2538674A IT1017311B (it)	1973-07-20	1974-07-19	Fenol aldeidi
AT600874A AT336575B (de)	1973-07-20	1974-07-19	Verfahren zur herstellung von neuen p-hydroxyphenylalkanalen
ES428400A ES428400A1 (es)	1973-07-20	1974-07-19	Procedimiento para la preparacion de nuevos fenolaldehidos.
BE146718A BE817837A (fr)	1973-07-20	1974-07-19	Aldehyde-phenols utilisables comme stabilisants pour des matieres orgaaniques oxydables
FR7425178A FR2237870B1 (fr)	1973-07-20	1974-07-19
DK392774A DK392774A (fr)	1973-07-20	1974-07-19
JP8314774A JPS5044182A (fr)	1973-07-20	1974-07-19
JP11858274A JPS5111726A (en)	1973-07-20	1974-10-15	Fuenooruarudehidono seizohoho

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1065073A CH585685A5 (en)	1973-07-20	1973-07-20	Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde

Publications (1)

Publication Number	Publication Date
CH585685A5 true CH585685A5 (en)	1977-03-15

Family

ID=4365389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1065073A CH585685A5 (en)	1973-07-20	1973-07-20	Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde

Country Status (3)

Country	Link
BE (1)	BE817837A (fr)
CH (1)	CH585685A5 (fr)
SU (1)	SU657741A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4091225A (en)	1974-01-22	1978-05-23	The Goodyear Tire & Rubber Company	Antioxidant ester substituted phenols and process for their preparation

1973
- 1973-07-20 CH CH1065073A patent/CH585685A5/de not_active IP Right Cessation
1974
- 1974-07-18 SU SU742046325A patent/SU657741A3/ru active
- 1974-07-19 BE BE146718A patent/BE817837A/fr unknown

Also Published As

Publication number	Publication date
BE817837A (fr)	1975-01-20
SU657741A3 (ru)	1979-04-15

Legal Events

Date	Code	Title	Description
1980-05-14	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US3971757A (en)	1976-07-27	3-Alkyl-4-oxo-imidazolidines and their 1-oxyls
EP0052579B1 (fr)	1984-11-14	Stabilisants contre la lumière
DE2414417A1 (de)	1974-10-31	N-(3-hydroxyaryl-propyl)-imide
DE2428877A1 (de)	1975-01-23	4-alkyl-1,4-diaza-5-oxo-cycloheptane und ihre 1-oxyle
DE2422158A1 (de)	1974-12-12	3-hydroxybenzyl-oxadiazolon- und thiadiazolonderivate
EP0214102B1 (fr)	1990-05-23	2-H-benzotriazoles substituées en position 5 par un aralcoyle et compositions stabilisées
DE2501285A1 (de)	1975-07-24	Neue phenolacetale
DE2501332A1 (de)	1975-07-24	Neue phenolacetale
DE2623464A1 (de)	1976-12-16	Neue polymer-stabilisatoren
DE2433050C2 (de)	1983-06-09	Phenolaldehyde, Verfahren zu ihrer Herstellung und Mittel zur Stabilisierung organischer Substrate
US3992420A (en)	1976-11-16	3,5-dialkyl-4-hydroxybenzyl-oxiranes
US4044019A (en)	1977-08-23	Hydroxyphenylated hydantoins
EP0005447B1 (fr)	1982-05-05	Phénylphosphonites avec des substituants ortho-alkyle, procédé pour leur préparation et compositions stabilisées
DE2614740A1 (de)	1976-10-21	Neue dione
EP0114148B1 (fr)	1988-09-07	Dioxasilépine et dioxasilocine comme stabilisateur
DE2431623A1 (de)	1975-04-17	Bicyclische phosphite als verarbeitungsstabilisatoren
CH585685A5 (en)	1977-03-15	Aldehyde-phenols useful as antioxidants of org. materials - prepd. from substd. benzyl dithiocarbamate and aldehyde
EP0158598B1 (fr)	1989-01-04	Composés de pipéridine
DE2346458A1 (de)	1974-04-11	Thiaalkylphenole
EP0113318A1 (fr)	1984-07-11	(4-Hydroxyphénylthio)-imides utilisés comme stabilisants
DE2411666A1 (de)	1974-10-10	Phosphorsaeureanilide
US4177213A (en)	1979-12-04	Process for benzylating ketones
DE2347997A1 (de)	1974-04-04	Bicyclische phosphorverbindungen
DE2329494C2 (de)	1982-05-06	3,5-Dialkyl-4-hydroxybenzyl-oxirane und -thiirane, Verfahren zu deren Herstellung und deren Verwendung
DE2451179A1 (de)	1975-05-07	Verfahren zur benzylierung von ketonen