DE1170633B - Stabilisierte Formmassen aus Olefinpolymerisaten - Google Patents
Stabilisierte Formmassen aus OlefinpolymerisatenInfo
- Publication number
- DE1170633B DE1170633B DEF35090A DEF0035090A DE1170633B DE 1170633 B DE1170633 B DE 1170633B DE F35090 A DEF35090 A DE F35090A DE F0035090 A DEF0035090 A DE F0035090A DE 1170633 B DE1170633 B DE 1170633B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- bis
- contain
- hydroxy
- methane
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 229920000098 polyolefin Polymers 0.000 title claims description 11
- 238000000465 moulding Methods 0.000 title claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- -1 thiodicarboxylic acid ester Chemical class 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- VXTYCJJHHMLIBM-UHFFFAOYSA-N carboxysulfanylformic acid Chemical class OC(=O)SC(O)=O VXTYCJJHHMLIBM-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 description 23
- 230000032050 esterification Effects 0.000 description 14
- 238000005886 esterification reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 4
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 4
- XOUGZRFGOBEBSK-UHFFFAOYSA-N OC1=C(C=C(C=C1C)CCCCCCCC)CC1=C(C(=CC(=C1)CCCCCCCC)C)O Chemical compound OC1=C(C=C(C=C1C)CCCCCCCC)CC1=C(C(=CC(=C1)CCCCCCCC)C)O XOUGZRFGOBEBSK-UHFFFAOYSA-N 0.000 description 4
- 239000003490 Thiodipropionic acid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 235000019303 thiodipropionic acid Nutrition 0.000 description 4
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 3
- XDILCINHTMZTGG-UHFFFAOYSA-N 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(O)=O XDILCINHTMZTGG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- HGTBAIVLETUVCG-UHFFFAOYSA-N (methylthio)acetic acid Chemical compound CSCC(O)=O HGTBAIVLETUVCG-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- LSEDQAPMYXQDRC-UHFFFAOYSA-N 11-dodecylsulfanylundecanoic acid Chemical compound CCCCCCCCCCCCSCCCCCCCCCCC(O)=O LSEDQAPMYXQDRC-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- FHTRYIHBMTYTQT-UHFFFAOYSA-N 2,4-dibromo-6-[(3,5-dibromo-2-hydroxyphenyl)methyl]phenol Chemical compound OC1=C(Br)C=C(Br)C=C1CC1=CC(Br)=CC(Br)=C1O FHTRYIHBMTYTQT-UHFFFAOYSA-N 0.000 description 1
- CELSEOKAEJGADX-UHFFFAOYSA-N 2,6-dimethyl-4-octylphenol Chemical compound CCCCCCCCC1=CC(C)=C(O)C(C)=C1 CELSEOKAEJGADX-UHFFFAOYSA-N 0.000 description 1
- SBVZHZXDINSDOC-UHFFFAOYSA-N 2-(2-octadecoxy-2-oxoethyl)sulfanylacetic acid Chemical compound C(CCCCCCCCCCCCCCCCC)OC(CSCC(=O)O)=O SBVZHZXDINSDOC-UHFFFAOYSA-N 0.000 description 1
- NLJQQCDVFXAPAG-UHFFFAOYSA-N 2-(4-hydroxy-3-methylphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(O)C(C)=C1 NLJQQCDVFXAPAG-UHFFFAOYSA-N 0.000 description 1
- CNGCNMVXDKZYNN-UHFFFAOYSA-N 2-[(2-dodecoxy-2-oxoethyl)disulfanyl]acetic acid Chemical compound CCCCCCCCCCCCOC(=O)CSSCC(=O)O CNGCNMVXDKZYNN-UHFFFAOYSA-N 0.000 description 1
- WFNXYMSIAASORV-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)cyclohexyl]phenol Chemical compound OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)CCCCC1 WFNXYMSIAASORV-UHFFFAOYSA-N 0.000 description 1
- DOGVTGGERWCNON-UHFFFAOYSA-N 2-[2-(2-hydroxy-5-nonylphenyl)propan-2-yl]-4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(C(C)(C)C=2C(=CC=C(CCCCCCCCC)C=2)O)=C1 DOGVTGGERWCNON-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- LZQSKUQISWIZQS-UHFFFAOYSA-N 2-dodecylsulfanylacetic acid Chemical compound CCCCCCCCCCCCSCC(O)=O LZQSKUQISWIZQS-UHFFFAOYSA-N 0.000 description 1
- YXNWKYMLMYBZSA-UHFFFAOYSA-N 2-dodecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCSC(C)C(O)=O YXNWKYMLMYBZSA-UHFFFAOYSA-N 0.000 description 1
- VJIKFWJCVWFZIN-UHFFFAOYSA-N 2-ethylsulfanylacetic acid Chemical compound CCSCC(O)=O VJIKFWJCVWFZIN-UHFFFAOYSA-N 0.000 description 1
- YNGUXAKJEVGKCF-UHFFFAOYSA-N 2-octadecylsulfanylacetic acid Chemical compound CCCCCCCCCCCCCCCCCCSCC(O)=O YNGUXAKJEVGKCF-UHFFFAOYSA-N 0.000 description 1
- KZYNPINQSVKGQR-UHFFFAOYSA-N 2-octadecylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCCCCCCCSC(C)C(O)=O KZYNPINQSVKGQR-UHFFFAOYSA-N 0.000 description 1
- OATWDMWDOACCLA-UHFFFAOYSA-N 3-octadecylsulfanylbutanoic acid Chemical compound CCCCCCCCCCCCCCCCCCSC(C)CC(O)=O OATWDMWDOACCLA-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical group C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- ACAYZXFEFNEADF-UHFFFAOYSA-N 5-(4-carboxybutylsulfanyl)pentanoic acid Chemical compound OC(=O)CCCCSCCCCC(O)=O ACAYZXFEFNEADF-UHFFFAOYSA-N 0.000 description 1
- UWKRBLZTYVNVAD-UHFFFAOYSA-N CCCCCCCCCCCCOC(=O)CSCC(=O)O Chemical compound CCCCCCCCCCCCOC(=O)CSCC(=O)O UWKRBLZTYVNVAD-UHFFFAOYSA-N 0.000 description 1
- UMGQZSNWCHWZDH-UHFFFAOYSA-N CCCCCCCCCCCCSSCC(O)=O Chemical compound CCCCCCCCCCCCSSCC(O)=O UMGQZSNWCHWZDH-UHFFFAOYSA-N 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- LNPSNSGMMFJKNQ-UHFFFAOYSA-N dodecyl 3,3-bis(4-hydroxy-3-methylphenyl)butanoate Chemical compound C(CCCCCCCCCCC)OC(CC(C)(C1=CC(=C(C=C1)O)C)C1=CC(=C(C=C1)O)C)=O LNPSNSGMMFJKNQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003464 sulfur compounds Chemical class 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE623355D BE623355A (en, 2012) | 1961-10-07 | ||
| DEF35090A DE1170633B (de) | 1961-10-07 | 1961-10-07 | Stabilisierte Formmassen aus Olefinpolymerisaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35090A DE1170633B (de) | 1961-10-07 | 1961-10-07 | Stabilisierte Formmassen aus Olefinpolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1170633B true DE1170633B (de) | 1964-05-21 |
Family
ID=7095845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF35090A Pending DE1170633B (de) | 1961-10-07 | 1961-10-07 | Stabilisierte Formmassen aus Olefinpolymerisaten |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE623355A (en, 2012) |
| DE (1) | DE1170633B (en, 2012) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE582162A (en, 2012) * | 1958-09-18 | |||
| BE577252A (en, 2012) * | 1958-04-04 | Hercules Powder Co Ltd |
-
0
- BE BE623355D patent/BE623355A/xx unknown
-
1961
- 1961-10-07 DE DEF35090A patent/DE1170633B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE577252A (en, 2012) * | 1958-04-04 | Hercules Powder Co Ltd | ||
| BE582162A (en, 2012) * | 1958-09-18 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE623355A (en, 2012) |
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