CA1121380A - Phenol-hydrazones empeches et substances stabilises au moyen de ces derniers - Google Patents

Phenol-hydrazones empeches et substances stabilises au moyen de ces derniers

Info

Publication number: CA1121380A
Authority: CA; Canada
Prior art keywords: butyl; compound; hydrazone; alkyl; hydroxyphenyl
Prior art date: 1976-12-30
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

Application number

CA000293996A

Other languages

English (en)

Inventor

David H. Steinberg

Martin Dexter

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1976-12-30

Filing date

1977-12-28

Publication date

1982-04-06

1977-12-28 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1982-04-06 Application granted granted Critical

1982-04-06 Publication of CA1121380A publication Critical patent/CA1121380A/fr

Status Expired legal-status Critical Current

Links

-1 phenol hydrazones Chemical class 0.000 title claims abstract description 25
239000000203 mixture Substances 0.000 title claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 21
239000003381 stabilizer Substances 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
239000011593 sulfur Substances 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 16
229920001971 elastomer Polymers 0.000 claims description 14
239000005060 rubber Substances 0.000 claims description 14
150000007857 hydrazones Chemical class 0.000 claims description 8
239000005062 Polybutadiene Substances 0.000 claims description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 5
229920002857 polybutadiene Polymers 0.000 claims description 5
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 4
229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 4
239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 4
229920001195 polyisoprene Polymers 0.000 claims description 4
229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims 1
KNYDGAALLPCERY-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CCC(=O)CC(C=NN)(C)SCCCCCCCCCCCCC Chemical group C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CCC(=O)CC(C=NN)(C)SCCCCCCCCCCCCC KNYDGAALLPCERY-UHFFFAOYSA-N 0.000 claims 1
238000010525 oxidative degradation reaction Methods 0.000 claims 1
229920003244 diene elastomer Polymers 0.000 abstract description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
229920001577 copolymer Polymers 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004132 cross linking Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000004743 Polypropylene Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
AXONOMLMGXEKIQ-UHFFFAOYSA-N 2-dodecylsulfanylpropanal Chemical compound CCCCCCCCCCCCSC(C)C=O AXONOMLMGXEKIQ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
210000004905 finger nail Anatomy 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000000758 substrate Substances 0.000 description 3
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
229920013623 Solprene Polymers 0.000 description 2
239000002174 Styrene-butadiene Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000032683 aging Effects 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000007906 compression Methods 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
OWPOPWLPWKSLMS-UHFFFAOYSA-N hydrazine;phenol Chemical compound NN.OC1=CC=CC=C1 OWPOPWLPWKSLMS-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 2
229940049964 oleate Drugs 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
DMIIFJJYGCGBLR-UHFFFAOYSA-N 2-dodecylsulfanyl-3-phenylpropanal Chemical compound CCCCCCCCCCCCSC(C=O)CC1=CC=CC=C1 DMIIFJJYGCGBLR-UHFFFAOYSA-N 0.000 description 1
FQXONOISHKWAAT-UHFFFAOYSA-N 2-dodecylsulfanylbutanal Chemical compound CCCCCCCCCCCCSC(CC)C=O FQXONOISHKWAAT-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
PAUVHUASIFNNSR-UHFFFAOYSA-N 2-ethylsulfanylbutanal Chemical compound CCSC(CC)C=O PAUVHUASIFNNSR-UHFFFAOYSA-N 0.000 description 1
QCXHWPKUSWMCSZ-UHFFFAOYSA-N 2-octylsulfanylacetaldehyde Chemical compound CCCCCCCCSCC=O QCXHWPKUSWMCSZ-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
PXMJCECEFTYEKE-UHFFFAOYSA-N Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester Chemical compound COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PXMJCECEFTYEKE-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
RMGRWKPHSDKRQP-UHFFFAOYSA-N acetic acid;2-ethylsulfanylbutanal Chemical compound CC(O)=O.CCSC(CC)C=O RMGRWKPHSDKRQP-UHFFFAOYSA-N 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
QAWVDHLPGCSZMM-UHFFFAOYSA-N dodecanoic acid;2-ethylsulfanylbutanal Chemical compound CCSC(CC)C=O.CCCCCCCCCCCC(O)=O QAWVDHLPGCSZMM-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002118 epoxides Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
125000005597 hydrazone group Chemical group 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000018984 mastication Effects 0.000 description 1
238000010077 mastication Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
239000010723 turbine oil Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
- C08K5/30—Hydrazones; Semicarbazones
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen

Landscapes

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

CA000293996A 1976-12-30 1977-12-28 Phenol-hydrazones empeches et substances stabilises au moyen de ces derniers Expired CA1121380A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US75603076A	1976-12-30	1976-12-30
US756,030		1991-09-06

Publications (1)

Publication Number	Publication Date
CA1121380A true CA1121380A (fr)	1982-04-06

Family

ID=25041735

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000293996A Expired CA1121380A (fr)	1976-12-30	1977-12-28	Phenol-hydrazones empeches et substances stabilises au moyen de ces derniers

Country Status (7)

Country	Link
JP (1)	JPS5384939A (fr)
BE (1)	BE862458A (fr)
CA (1)	CA1121380A (fr)
DE (1)	DE2756612A1 (fr)
FR (1)	FR2376129A1 (fr)
GB (1)	GB1544764A (fr)
NL (1)	NL7713922A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1192559A (fr) *	1982-04-09	1985-08-27	Ralph H. Hansen	Constituants polymeriques et compose utile pour ces constituants
US5302744A (en) *	1992-03-27	1994-04-12	Eastman Kodak Company	Phenolic-hydrazide compounds and polyolefin compositions stabilized therewith

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3773722A (en) *	1969-03-28	1973-11-20	Ciba Geigy Corp	Synthetic organic polymeric substances stabilized with alkylhydroxyphenyl-alkanoyl-hydrazines

1977
- 1977-12-08 GB GB51213/77A patent/GB1544764A/en not_active Expired
- 1977-12-15 NL NL7713922A patent/NL7713922A/xx not_active Application Discontinuation
- 1977-12-19 DE DE19772756612 patent/DE2756612A1/de not_active Withdrawn
- 1977-12-28 JP JP15863077A patent/JPS5384939A/ja active Pending
- 1977-12-28 CA CA000293996A patent/CA1121380A/fr not_active Expired
- 1977-12-29 FR FR7739619A patent/FR2376129A1/fr active Granted
- 1977-12-29 BE BE183956A patent/BE862458A/fr unknown

Also Published As

Publication number	Publication date
DE2756612A1 (de)	1978-07-13
FR2376129A1 (fr)	1978-07-28
BE862458A (fr)	1978-06-29
FR2376129B1 (fr)	1980-02-01
GB1544764A (en)	1979-04-25
NL7713922A (nl)	1978-07-04
JPS5384939A (en)	1978-07-26

Legal Events

Date	Code	Title	Description
1999-04-06	MKEX	Expiry

Publication	Publication Date	Title
JP2683100B2 (ja)	1997-11-26	酸化防止剤
US4446264A (en)	1984-05-01	Synergistic antioxidant mixtures
CA1121380A (fr)	1982-04-06	Phenol-hydrazones empeches et substances stabilises au moyen de ces derniers
US3062895A (en)	1962-11-06	Polynuclear polyphenols
US4058502A (en)	1977-11-15	Stabilized compositions containing hindered hydroxyalkanoates
US3676449A (en)	1972-07-11	1,3,4-thiadiazole-bridged thiomethylenephenol antioxidants
US3975360A (en)	1976-08-17	Age resisters for oxidizable polymers
US4081475A (en)	1978-03-28	Trialkylsubstituted hydroxybenzyl malonates and stabilized compositions
EP0006745B1 (fr)	1982-11-10	Esters d'un acide phénylpropionique substitué contenant un groupe nitro, compositions les contenant comme agents stabilisants contre la dégradation oxydative et compositions stabilisantes
US4067933A (en)	1978-01-10	Phenolic phosphites as stabilizers for polymers
US3896146A (en)	1975-07-22	3,5-dialkyl-4-hydroxyphenylalkyl substituted tricyclic imides
US3594424A (en)	1971-07-20	2,6-bis(3,5-dialkyl-4-hydroxybenzyl) cycloalkanones
US3991131A (en)	1976-11-09	Azidoformyl antioxidants
US3644539A (en)	1972-02-22	Synthesis of hindered alkenyl phenols
US4233209A (en)	1980-11-11	Hindered phenol hydrazones and compositions stabilized therewith
US3265661A (en)	1966-08-09	2, 4, 6-tris (3, 5-di-tert butyl-4-hydroxybenzyl) phenyl alkanoates and polypropylene compositions stabilized therewith
CA1084062A (fr)	1980-08-19	Antioxydants biphenoliques contenant du soufre
US3987086A (en)	1976-10-19	Hindered hydroxyphenylalkanoates of substituted vicinal glycols
US4618637A (en)	1986-10-21	Polymer mixture which comprises a polyphenylene ether and a dihydrazide as a stabilizer
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