GB1037169A - Stabilization of polymers - Google Patents
Stabilization of polymersInfo
- Publication number
- GB1037169A GB1037169A GB892365A GB892365A GB1037169A GB 1037169 A GB1037169 A GB 1037169A GB 892365 A GB892365 A GB 892365A GB 892365 A GB892365 A GB 892365A GB 1037169 A GB1037169 A GB 1037169A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diethyl
- methoxybenzylidene
- malonate
- incorporated
- malonates
- 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.)
- Expired
Links
- 229920000642 polymer Polymers 0.000 title abstract 2
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- -1 Benzylidene malonic acid diesters Chemical class 0.000 abstract 15
- 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 abstract 4
- XPPJWQQFELGACY-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-1,3-dioxane-4,6-dione Chemical class C1(CC(=O)OC(C2=C(C=C(C=C2)OC)OC)O1)=O XPPJWQQFELGACY-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229920002301 cellulose acetate Polymers 0.000 abstract 3
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 abstract 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 abstract 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000004793 Polystyrene Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000002530 phenolic antioxidant Substances 0.000 abstract 2
- 229920002223 polystyrene Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 abstract 1
- ZBEGLEYBWGNZJA-UHFFFAOYSA-N 4-dodecoxybenzaldehyde Chemical compound CCCCCCCCCCCCOC1=CC=C(C=O)C=C1 ZBEGLEYBWGNZJA-UHFFFAOYSA-N 0.000 abstract 1
- KVOWZHASDIKNFK-UHFFFAOYSA-N 4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=CC=C(C=O)C=C1 KVOWZHASDIKNFK-UHFFFAOYSA-N 0.000 abstract 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical class CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 abstract 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- JMFYZMAVUHNCPW-UHFFFAOYSA-N dimethyl 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound COC(=O)C(C(=O)OC)=CC1=CC=C(OC)C=C1 JMFYZMAVUHNCPW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- HCWOVPZEAFLXPL-UHFFFAOYSA-N diphenyl propanedioate Chemical class C=1C=CC=CC=1OC(=O)CC(=O)OC1=CC=CC=C1 HCWOVPZEAFLXPL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004417 polycarbonate Substances 0.000 abstract 1
- 229920000515 polycarbonate Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 239000005033 polyvinylidene chloride Substances 0.000 abstract 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 abstract 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Benzylidene malonic acid diesters may be prepared by reacting benzaldehydes with malonic acid diesters. In Example 1 p-methoxybenzaldehyde is reacted with diethyl malonate in benzene in the presence of piperidine. Corresponding products may be derived from benzaldehyde, o-methoxybenzaldehyde, p-hydroxybenzaldehyde, 2,4 - dimethoxybenzaldehyde, 2,5 - dimethoxybenzaldehyde, p - octyloxybenzaldehyde and p-dodecyloxybenzaldehyde, and from dimethyl, dioctyl, dibenzyl and diphenyl malonates.ALSO:Polymers are stabilized by incorporating therein a benzylidene malonic ester of formula <FORM:1037169/C3/1> where R and R1 are hydrogen, hydroxy, C1- 12 alkoxy, C1- 12 alkyl, C2- 12 alkanoyloxy, C2- 12 alkenyloxy or C3- 12 alkenoyloxy; and R11 and R111 are C1- 12 alkyl, aryl or aralkyl. The esters may be used together with phenolic antioxidants. Specified polymeric materials are cellulose acetate, polyethylene, polypropylene, polystyrene, polymethyl acrylate, polymetnyl methacrylate, polyvinyl chloride, polyvinylidene chloride, polyesters, polycarbonates and melamine resins. Specified phenolic antioxidants are 2,6-di-t-butyl 4-methyl-, 4-methylol-, 4 - ethyl- and 4 - octyl phenols, 2,6 - di - hexyl - 4 - methyl- and 4 - t - butyl - phenols, and 2,4,6-tri-t-butyl phenol. In comparative tests diethyl esters in which R1 is H and R is H or p-methoxy are incorporated in cellulose acetate, and in Examples (9) diethyl p-methoxybenzylidene, benzylidene, o-methoxybenzylidene, p-hydroxybenzylidene and 2,4-dimethoxybenzylidene malonates are incorporated in cellulose acetate; (10) diethyl p-methoxybenzylidene malonate and (11) diethyl 4-acryloxybenzylidene malonate, diethyl 4-octyloxybenzylidene malonate and dimethyl p-methoxybenzylidene malonate are incorporated in organo tin heat-stabilized polyvinyl chloride; (12) diethyl p-methoxybenzylidene, benzylidene, o-methoxybenzylidene, p-hydroxybenzylidene and 2,4-dimethoxybenzylidene malonates are incorporated in organo tin heat-stabilized vinyl chloride/vinyl acetate copolymers; (13) diethyl p-methoxybenzylidene, o-methoxybenzylidene, p-hydroxybenzylidene and 2,4-dimethoxybenzylidene malonates and (14) diethyl p-methoxybenzylidene malonate and 2,4,6-tri-t-butyl phenol are incorporated in polystyrene and (15) diethyl p-methoxybenzylidene malonate is incorporated in benzoguanamino - melamine - formaldehyde resins.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36218264A | 1964-04-23 | 1964-04-23 | |
| US38921064A | 1964-08-12 | 1964-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1037169A true GB1037169A (en) | 1966-07-27 |
Family
ID=27001588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB892365A Expired GB1037169A (en) | 1964-04-23 | 1965-03-02 | Stabilization of polymers |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH452185A (en) |
| DE (1) | DE1544605C3 (en) |
| GB (1) | GB1037169A (en) |
| NL (1) | NL142443B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002837A3 (en) * | 1977-12-29 | 1979-07-25 | Gaf Corporation | Radiation curable coating composition comprising an oligomer, and an ultra-violet absorber |
| EP0100651A1 (en) * | 1982-08-03 | 1984-02-15 | VAN DYK & COMPANY, INC. | Dialkyl malonates as organic suncreen adjuvants |
| EP0350386A1 (en) * | 1988-07-08 | 1990-01-10 | L'oreal | Unsaturated derivatives of lipid soluble benzal malonates, and their use as UV absorbers in the cosmetic field |
| US9051448B2 (en) | 2004-08-31 | 2015-06-09 | Basf Se | Stabilization of organic materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2310135C3 (en) * | 1973-03-01 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | 4-Phenylbenzylidenemalonic acid derivatives and their use for stabilizing polymers against UV radiation |
-
1965
- 1965-03-02 GB GB892365A patent/GB1037169A/en not_active Expired
- 1965-03-16 NL NL6503314A patent/NL142443B/en unknown
- 1965-03-27 DE DE19651544605 patent/DE1544605C3/en not_active Expired
- 1965-04-22 CH CH559065A patent/CH452185A/en not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002837A3 (en) * | 1977-12-29 | 1979-07-25 | Gaf Corporation | Radiation curable coating composition comprising an oligomer, and an ultra-violet absorber |
| EP0100651A1 (en) * | 1982-08-03 | 1984-02-15 | VAN DYK & COMPANY, INC. | Dialkyl malonates as organic suncreen adjuvants |
| EP0350386A1 (en) * | 1988-07-08 | 1990-01-10 | L'oreal | Unsaturated derivatives of lipid soluble benzal malonates, and their use as UV absorbers in the cosmetic field |
| US5175340A (en) * | 1988-07-08 | 1992-12-29 | L'oreal | New liposoluble unsaturated benzalmalonate derivatives and their use as absorbers for ultraviolet radiation in cosmetics |
| US9051448B2 (en) | 2004-08-31 | 2015-06-09 | Basf Se | Stabilization of organic materials |
| EP1791901B1 (en) * | 2004-08-31 | 2018-03-28 | Basf Se | Stabilization of organic materials |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1544605A1 (en) | 1969-05-08 |
| CH452185A (en) | 1968-05-31 |
| NL142443B (en) | 1974-06-17 |
| DE1544605C3 (en) | 1975-10-09 |
| NL6503314A (en) | 1965-10-25 |
| DE1544605B2 (en) | 1975-02-06 |
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