CA2363543A1 - Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation - Google Patents
Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation Download PDFInfo
- Publication number
- CA2363543A1 CA2363543A1 CA002363543A CA2363543A CA2363543A1 CA 2363543 A1 CA2363543 A1 CA 2363543A1 CA 002363543 A CA002363543 A CA 002363543A CA 2363543 A CA2363543 A CA 2363543A CA 2363543 A1 CA2363543 A1 CA 2363543A1
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- CA
- Canada
- Prior art keywords
- group
- mixtures
- hydrogen
- physical
- alkyl
- 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.)
- Granted
Links
- -1 amine derivatives of butylated hydroxy toluene Chemical class 0.000 title abstract 2
- 238000002144 chemical decomposition reaction Methods 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 230000003078 antioxidant effect Effects 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000006165 cyclic alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical class CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000002845 discoloration Methods 0.000 abstract 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000005562 fading Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 235000010199 sorbic acid Nutrition 0.000 abstract 1
- 229940075582 sorbic acid Drugs 0.000 abstract 1
- 239000004334 sorbic acid Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
The present invention relates to novel antioxidant compounds to reduce the physical or chemical degradation or discoloration of surfaces, especially the fading of a variety of surfaces from sunlight, wherein the antioxidant compound is a derivative of butylated hydroxytoluene or sorbic acid and is selected from the group consisting of: (I), (II), (III), (IV), wherein each R1 and R3 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof; R2 is a hydroxy group; each R4 and R7 is selected from the group consisting of a saturated or unsaturated C1-C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), hydrogen, and mixtures thereof; each R5, R6, R8, and R9 is selected from the group consisting of a saturated or unsaturated C1-C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), and mixtures thereof; n is from 1 to 50; Y is a hydrogen or a methyl group; Z is a hydrogen or a methyl group; wherein the amino group of the compounds of formulas (I) to (IV) can be protonated or quaternized with R10X
where R10 is a hydrogen, a C1-C6 alkyl group, C1-C6 hydroxyl alkyl group, benzyl group and mixtures thereof; and X- is any compatible anion.
where R10 is a hydrogen, a C1-C6 alkyl group, C1-C6 hydroxyl alkyl group, benzyl group and mixtures thereof; and X- is any compatible anion.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/280,685 US5543083A (en) | 1994-07-26 | 1994-07-26 | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
| US08/280,685 | 1994-07-26 | ||
| CA002192803A CA2192803A1 (en) | 1994-07-26 | 1995-07-13 | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002192803A Division CA2192803A1 (en) | 1994-07-26 | 1995-07-13 | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2363543A1 true CA2363543A1 (en) | 1996-02-08 |
| CA2363543C CA2363543C (en) | 2003-11-11 |
Family
ID=25678921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002363543A Expired - Fee Related CA2363543C (en) | 1994-07-26 | 1995-07-13 | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2363543C (en) |
-
1995
- 1995-07-13 CA CA002363543A patent/CA2363543C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2363543C (en) | 2003-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |