DE2042652A1 - Thiobisphenol Nickel Alkanolamm Komplexe - Google Patents
Thiobisphenol Nickel Alkanolamm KomplexeInfo
- Publication number
- DE2042652A1 DE2042652A1 DE19702042652 DE2042652A DE2042652A1 DE 2042652 A1 DE2042652 A1 DE 2042652A1 DE 19702042652 DE19702042652 DE 19702042652 DE 2042652 A DE2042652 A DE 2042652A DE 2042652 A1 DE2042652 A1 DE 2042652A1
- Authority
- DE
- Germany
- Prior art keywords
- nickel
- complexes
- alkanolamine
- carbon atoms
- thiobis
- Prior art date
- 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.)
- Ceased
Links
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims description 22
- 229910052759 nickel Inorganic materials 0.000 title claims description 12
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 title description 2
- -1 carbalkoxyalkyl Chemical group 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical group OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- HHPDFYDITNAMAM-UHFFFAOYSA-N 2-[cyclohexyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCC1 HHPDFYDITNAMAM-UHFFFAOYSA-N 0.000 claims description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000002815 nickel Chemical class 0.000 description 14
- 239000004743 Polypropylene Substances 0.000 description 9
- 239000004611 light stabiliser Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 229940124543 ultraviolet light absorber Drugs 0.000 description 4
- 229910052724 xenon Inorganic materials 0.000 description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229950004864 olamine Drugs 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XRCGPZWJUXJKJF-UHFFFAOYSA-N (2-hydroxy-4-octoxyphenyl)-(2-hydroxyphenyl)methanone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1O XRCGPZWJUXJKJF-UHFFFAOYSA-N 0.000 description 1
- IADJBCIKCXGXDN-UHFFFAOYSA-N (4-butoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCC)=CC=C1C(=O)C1=CC=CC=C1 IADJBCIKCXGXDN-UHFFFAOYSA-N 0.000 description 1
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- CICLCIIIUOCDBN-UHFFFAOYSA-N (4-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=C(O)C=C1 CICLCIIIUOCDBN-UHFFFAOYSA-N 0.000 description 1
- ZQEWOHMGRGIMAO-UHFFFAOYSA-N 1-aminoethanol;nickel Chemical compound [Ni].CC(N)O ZQEWOHMGRGIMAO-UHFFFAOYSA-N 0.000 description 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- SGZMYCSMZPSIKX-UHFFFAOYSA-N 2-(2-hydroxy-5-nonylphenyl)sulfanyl-4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCCC)C=2)O)=C1 SGZMYCSMZPSIKX-UHFFFAOYSA-N 0.000 description 1
- LBOGPIWNHXHYHN-UHFFFAOYSA-N 2-(2-hydroxy-5-octylphenyl)sulfanyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCC)C=2)O)=C1 LBOGPIWNHXHYHN-UHFFFAOYSA-N 0.000 description 1
- OFQAXGURTISEGO-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol;nickel Chemical class [Ni].OC1=CC=CC=C1SC1=CC=CC=C1O OFQAXGURTISEGO-UHFFFAOYSA-N 0.000 description 1
- LLTGNYZQUXACFO-UHFFFAOYSA-N 2-(dicyclohexylamino)ethanol Chemical compound C1CCCCC1N(CCO)C1CCCCC1 LLTGNYZQUXACFO-UHFFFAOYSA-N 0.000 description 1
- WQYFETFRIRDUPJ-UHFFFAOYSA-N 2-[2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]sulfanyl-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(SC=2C(=CC=C(C=2)C(C)(C)CC(C)(C)C)O)=C1 WQYFETFRIRDUPJ-UHFFFAOYSA-N 0.000 description 1
- RMLOQPUPBVVMCO-UHFFFAOYSA-N 2-[2-hydroxyethyl(2-phenylethyl)amino]ethanol Chemical compound OCCN(CCO)CCC1=CC=CC=C1 RMLOQPUPBVVMCO-UHFFFAOYSA-N 0.000 description 1
- NDLNTMNRNCENRZ-UHFFFAOYSA-N 2-[2-hydroxyethyl(octadecyl)amino]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CCO NDLNTMNRNCENRZ-UHFFFAOYSA-N 0.000 description 1
- FKJVYOFPTRGCSP-UHFFFAOYSA-N 2-[3-aminopropyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCCN(CCO)CCO FKJVYOFPTRGCSP-UHFFFAOYSA-N 0.000 description 1
- MIZIOHLLYXVEHJ-UHFFFAOYSA-N 2-[benzyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=CC=C1 MIZIOHLLYXVEHJ-UHFFFAOYSA-N 0.000 description 1
- NKFNBVMJTSYZDV-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCCCCCCCCCN(CCO)CCO NKFNBVMJTSYZDV-UHFFFAOYSA-N 0.000 description 1
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QMXOPBLSYWMVFJ-UHFFFAOYSA-N 4-butyl-2-(5-butyl-2-hydroxyphenyl)sulfanylphenol Chemical compound CCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCC)C=2)O)=C1 QMXOPBLSYWMVFJ-UHFFFAOYSA-N 0.000 description 1
- LQEVUWMUNFKMGV-UHFFFAOYSA-N 4-cyclohexyl-2-(5-cyclohexyl-2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=C(C2CCCCC2)C=C1SC(C(=CC=1)O)=CC=1C1CCCCC1 LQEVUWMUNFKMGV-UHFFFAOYSA-N 0.000 description 1
- QDRFHDDAGLWIAJ-UHFFFAOYSA-N 4-dodecyl-2-(5-dodecyl-2-hydroxyphenyl)sulfanylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCCCCCC)C=2)O)=C1 QDRFHDDAGLWIAJ-UHFFFAOYSA-N 0.000 description 1
- VHCGDTWHGPVICR-UHFFFAOYSA-N 4-ethyl-2-(5-ethyl-2-hydroxyphenyl)sulfanylphenol Chemical compound CCC1=CC=C(O)C(SC=2C(=CC=C(CC)C=2)O)=C1 VHCGDTWHGPVICR-UHFFFAOYSA-N 0.000 description 1
- QIZUBPHXHVWGHD-UHFFFAOYSA-N 4-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=C(O)C=C1 QIZUBPHXHVWGHD-UHFFFAOYSA-N 0.000 description 1
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical class C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 101150025591 nodT gene Proteins 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- XHLCCKLLXUAKCM-UHFFFAOYSA-N octadecyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XHLCCKLLXUAKCM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 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
- 239000000049 pigment Substances 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 239000000758 substrate Substances 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85350769A | 1969-08-27 | 1969-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2042652A1 true DE2042652A1 (de) | 1971-03-04 |
Family
ID=25316220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702042652 Ceased DE2042652A1 (de) | 1969-08-27 | 1970-08-27 | Thiobisphenol Nickel Alkanolamm Komplexe |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3636023A (forum.php) |
| JP (1) | JPS4943959B1 (forum.php) |
| BE (1) | BE755315A (forum.php) |
| CA (1) | CA966141A (forum.php) |
| CH (1) | CH571014A5 (forum.php) |
| DE (1) | DE2042652A1 (forum.php) |
| ES (1) | ES382475A1 (forum.php) |
| FR (1) | FR2058986A5 (forum.php) |
| GB (1) | GB1317473A (forum.php) |
| NL (1) | NL7012695A (forum.php) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2371431A1 (fr) * | 1975-06-19 | 1978-06-16 | Ciba Geigy Ag | Complexes metalliques de composes heterocycliques azotes, utilisables comme stabilisants de macropolymeres |
| EP0000700A1 (de) * | 1977-07-15 | 1979-02-21 | Ciba-Geigy Ag | Metallkomplexe mit einem Phenolatgruppe enthaltenden chelatbindenden Anion; deren Herstellung und Verwendung als Lichtschutzmittel insbesondere in hochmolekularen Verbindungen |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4025488A (en) * | 1971-02-08 | 1977-05-24 | Phillips Petroleum Company | Ultraviolet light stabilized α-olefins |
| BE794107A (fr) * | 1972-01-17 | 1973-07-16 | American Cyanamid Co | Caoutchoucs proteges contre l'oxydation par des complexes de nickel |
| US3975358A (en) * | 1972-04-26 | 1976-08-17 | American Cyanamid Company | Polymers stabilized with an organo-nickel compound and a dialkyl pentaerythritol diphosphite |
| CH574982A5 (forum.php) * | 1972-06-21 | 1976-04-30 | Ciba Geigy Ag | |
| US4026866A (en) * | 1972-06-21 | 1977-05-31 | Ciba-Geigy Corporation | Nickel stabilizers for synthetic polymers |
| US3819569A (en) * | 1973-06-28 | 1974-06-25 | Du Pont | Aromatic polyamides stabilized with nickelous carbonate |
| US4166105A (en) * | 1973-07-30 | 1979-08-28 | Block Engineering, Inc. | Dye tagged reagent |
| US4018808A (en) * | 1974-02-06 | 1977-04-19 | Uniroyal, Inc. | Hydrazino nickel thio-bis-phenolates and polyolefins stabilized thereby against the effects of heat and light |
| US4119548A (en) * | 1977-10-28 | 1978-10-10 | Mobil Oil Corporation | Reaction product of nickel thiobis(alkylphenolate) and thiobis(alkylphenol) and organic compositions containing the same |
| US4192757A (en) * | 1978-04-21 | 1980-03-11 | Exxon Research & Engineering Company | Alkyl phenol solutions of organo molybdenum complexes as friction reducing antiwear additives |
| US4201683A (en) * | 1978-04-21 | 1980-05-06 | Exxon Research & Engineering Co. | Alkanol solutions of organo molybdenum complexes as friction reducing antiwear additives |
| US4198303A (en) * | 1978-05-01 | 1980-04-15 | Mobil Oil Corporation | Antioxidant lubricant compositions |
| JPS5867887U (ja) * | 1981-10-30 | 1983-05-09 | 東商事株式会社 | ウインチ |
| JPS5867888U (ja) * | 1981-10-30 | 1983-05-09 | 東商事株式会社 | ウインチ |
| JPS61235399A (ja) * | 1985-04-09 | 1986-10-20 | 株式会社 山本製作所 | 物揚装置の自動逆転止め装置 |
-
1969
- 1969-08-27 US US853507A patent/US3636023A/en not_active Expired - Lifetime
-
1970
- 1970-05-11 CA CA082,459A patent/CA966141A/en not_active Expired
- 1970-05-15 GB GB2374270A patent/GB1317473A/en not_active Expired
- 1970-08-05 ES ES382475A patent/ES382475A1/es not_active Expired
- 1970-08-19 FR FR7030452A patent/FR2058986A5/fr not_active Expired
- 1970-08-21 JP JP45073397A patent/JPS4943959B1/ja active Pending
- 1970-08-26 BE BE755315D patent/BE755315A/xx unknown
- 1970-08-27 DE DE19702042652 patent/DE2042652A1/de not_active Ceased
- 1970-08-27 CH CH1286070A patent/CH571014A5/xx not_active IP Right Cessation
- 1970-08-27 NL NL7012695A patent/NL7012695A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2371431A1 (fr) * | 1975-06-19 | 1978-06-16 | Ciba Geigy Ag | Complexes metalliques de composes heterocycliques azotes, utilisables comme stabilisants de macropolymeres |
| EP0000700A1 (de) * | 1977-07-15 | 1979-02-21 | Ciba-Geigy Ag | Metallkomplexe mit einem Phenolatgruppe enthaltenden chelatbindenden Anion; deren Herstellung und Verwendung als Lichtschutzmittel insbesondere in hochmolekularen Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7012695A (forum.php) | 1971-03-02 |
| GB1317473A (en) | 1973-05-16 |
| CH571014A5 (forum.php) | 1975-12-31 |
| CA966141A (en) | 1975-04-15 |
| ES382475A1 (es) | 1973-04-16 |
| FR2058986A5 (forum.php) | 1971-05-28 |
| JPS4943959B1 (forum.php) | 1974-11-25 |
| US3636023A (en) | 1972-01-18 |
| BE755315A (fr) | 1971-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2042652A1 (de) | Thiobisphenol Nickel Alkanolamm Komplexe | |
| DE847491C (de) | Kunstharzzusammensetzung | |
| DE1769646C3 (de) | Stabilisierung von synthetischen Polymeren | |
| DE2166076A1 (de) | Dihydroxyspirochromanverbindungen, sowie diese dihydroxyspirochromanverbindungen enthaltende polyesterzusammensetzungen | |
| DE2255731A1 (de) | Sterisch gehinderte tris(metahydroxybenzyl)cyanurate | |
| DE2851448A1 (de) | Stabilisierung von polymeren | |
| DE2128757A1 (de) | Piperidinderivate und deren Verwendung als Stabilisatoren | |
| EP0019578B1 (de) | Piperidinverbindungen, Verfahren zu deren Herstellung und diese enthaltende polymere Zusammensetzungen | |
| DE2520725C3 (de) | UV-Stabilisator für Polymere | |
| DE2118298A1 (de) | Verwendung von Piperidonazinen zum Stabilisieren von organischem Material | |
| DE2017044C3 (de) | Nickel-Amid-Komplexe von 2,2'Thiobis-(p-t-octylphenol) und ein Verfahren zu ihrer Herstellung | |
| DE2316420A1 (de) | Nickel-cyclohexylamin-komplexe von 2,2' -thiobis(p-alkylphenolen) und ihre anwendung in polyolefinen | |
| DE1568884A1 (de) | Stabilisatoren fuer Polymerisate | |
| DE3012535C2 (de) | Methoxyzimtsäureester, Verfahren zu ihrer Herstellung und diese enthaltendes UV-Strahlung absorbierendes Mittel | |
| DE2616414A1 (de) | Sulfonsaeureester von 2,4-dihydroxybenzophenon | |
| DE2255730A1 (de) | Sterisch gehinderte tris(metahydroxybenzylthio)-s-triazine | |
| DE1232742B (de) | Formmassen aus Olefinpolymerisaten | |
| DE2203447A1 (de) | Diazepinon als Stabilisator | |
| DE2364120A1 (de) | Benzoyloxybenzoate und deren verwendung | |
| DE2242189A1 (de) | Metallkomplexe von aethylendinitriloessigsaeure-n,n'-dialkylestern, deren verwendung zum stabilisieren von organischen polymerisaten und damit stabilisierte produkte | |
| DE69016256T2 (de) | Stabilisierte Polypropylenfasern, pigmentiert mit Rot 144. | |
| DE2829390A1 (de) | Nickelstabilisatorzusammensetzung fuer polyolefine | |
| AT203488B (de) | Verfahren zur Herstellung von neuen Oxyketonen | |
| AT361715B (de) | Verfahren zur herstellung einer neuen nickel- stabilisatorzusammensetzung | |
| DE1768497A1 (de) | Als Antioxydantien brauchbare chemische Verbindungen und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |