US4107144A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenolic antioxidants with polymer tails
Assignee: Queen's University
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Filing: 1977-04-15
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Granted: 1978-08-15
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Expires: 1997-04-15
Abstract
Abstract Non-volatile antioxidants are prepared from dialkylphenols and selected vinylic monomers which polymerize cationically with acidic Lewis acid or Friedel-Crafts catalyst systems and attach to the phenolic ring. Operative phenolic antioxidants include 2,6-dialkylphenols particularly 2,6-ditertiarybutyl and 2,6-diisopropylphenol. Suitable vinylic monomers include isobutene and styrene. With 2,6-dialkylphenols the polymer chains attach to the 4-position of the phenol. The molecular weight of the chain or tail is controlled to be within about 1000 to 5000 preferably about 2000-3500, for a balance of anti-oxidant activity and immobility in the matrix polymer.
Inventors
- 👤 Kenneth E. Russell
- 👤 Linda G. M. C. Vail
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:56
CPC Classifications
C; C08; C08F; C08F110/00; C08F2/00; C08F2/44; C08G; C08G61/00; C08G61/02; C08G2261/00; C08G2261/30; C08G2261/34; C08G2261/342; C08G2261/3424
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
80 words
A dialkylphenol antioxidant having attached to the phenol in the 4 or 6 position on the ring a vinylic polymer tail of molecular weight from about 1000 to about 5000 as determined by vapor pressure osmometry or by gel permeation chromatography, said vinylic polymer being in the form of a pendant chain attached to said ring at one end of the chain derived from vinyl monomers which polymerize cationically with an acid catalyst of the Lewis Acid or Friedel-Crafts type.
Claim 2
Dependent Claim
80 words
A dialkylphenol antioxidant having attached to the phenol in the 4 or 6 position on the ring a vinylic polymer tail of molecular weight from about 1000 to about 5000 as determined by vapor pressure osmometry or by gel permeation chromatography, said vinylic polymer being in the form of a pendant chain attached to said ring at one end of the chain derived from vinyl monomers which polymerize cationically with an acid catalyst of the Lewis Acid or Friedel-Crafts type.
Claim 3
Dependent Claim
17 words
The dialkylphenol antioxidant of claim 1 wherein the alkyl groups are in the 2 and 6 positions.
Claim 4
Dependent Claim
17 words
The dialkylphenol antioxidant of claim 1 wherein the alkyl groups have from 2 to 8 carbon atoms.
Claim 5
Dependent Claim
14 words
The dialkylphenol antioxidant of claim 3 wherein the alkyl groups are tertiarybutyl or isopropyl.
Claim 6
Dependent Claim
27 words
The dialkylphenol antioxidant of claim 1 wherein the vinylic polymer is selected from the group consisting of polymers and copolymers of isobutene, styrene, propene, butene-1 and pentenes.
Claim 7
Dependent Claim
19 words
The dialkylphenol antioxidant of claim 1 having a polymer tail attached in the 4 position, said tail being polyisobutene.
Claim 8
Dependent Claim
19 words
The dialkylphenol antioxidant of claim 1 having a polymer tail attached in the 4 position, said tail being polystyrene.
Claim 9
Dependent Claim
24 words
The dialkylphenol antioxidant of claim 1 having a polymer tail attached in the 4 position, said tail being a copolymer of isobutene and styrene.
Claim 10
Dependent Claim
20 words
The dialkylphenol antioxidant of claim 1 wherein the polymer tail has a molecular weight of about 2000 to about 3500.
Claim 11
Dependent Claim
15 words
The dialkylphenol antioxidant of claim 1 wherein the phenol is a substituted diphenol or bisphenol.
Claim 12
Independent Claim
108 words
A method of preparing a dialkylphenol antioxidant having a polymeric side chain tail comprising (a) mixing a dialkylphenol antioxidant, a vinylic monomer able to polymerize cationically, a Friedel-Crafts or Lewis acid type catalyst, and an aprotic solvent for the mixture, the amount of monomer being sufficient to form the desired molecular weight polymer on each phenol molecule, (b) polymerizing said monomer cationically at temperatures below about 0° C and stopping the polymerization when the polymer molecular weight is within the range of about 1000 to 5000 as determined by vapor pressure osmometry or by gel permeation chromatography, and (c) recovering the dialkylphenol-bound polymer compound from the reaction mixture.
Claim 13
Independent Claim
108 words
A method of preparing a dialkylphenol antioxidant having a polymeric side chain tail comprising (a) mixing a dialkylphenol antioxidant, a vinylic monomer able to polymerize cationically, a Friedel-Crafts or Lewis acid type catalyst, and an aprotic solvent for the mixture, the amount of monomer being sufficient to form the desired molecular weight polymer on each phenol molecule, (b) polymerizing said monomer cationically at temperatures below about 0° C and stopping the polymerization when the polymer molecular weight is within the range of about 1000 to 5000 as determined by vapor pressure osmometry or by gel permeation chromatography, and (c) recovering the dialkylphenol-bound polymer compound from the reaction mixture.
Claim 14
Dependent Claim
17 words
The method of claim 11 wherein the dialkylphenol has alkyl groups in the 2 and 6 positions.
Claim 15
Dependent Claim
16 words
The method of claim 11 wherein the alkyl groups have from 2 to 8 carbon atoms.
Claim 16
Dependent Claim
13 words
The method of claim 13 wherein the alkyl groups are tertiarybutyl or isopropyl.
Claim 17
Dependent Claim
22 words
The method of claim 11 wherein the vinylic monomer is selected from the group consisting of isobutene, styrene, propene, butene-1; and pentenes.
Claim 18
Dependent Claim
16 words
The method of claim 11 wherein the catalyst comprises one of aluminum chloride, and boron trifluoride.
Claim 19
Dependent Claim
19 words
The method of claim 11 wherein the polymerization temperature is from below about 0° C to about -80° C.
Claim 20
Dependent Claim
15 words
The method of claim 11 wherein the polymerization is stopped by addition of an alcohol.
Claim 21
Dependent Claim
15 words
The method of claim 18 wherein sufficient alcohol is added to precipitate the phenol-polymer compound.
Claim 22
Dependent Claim
22 words
The method of claim 11 wherein the solvent is selected from the group consisting of methyl chloride, methylene chloride and ethyl chloride.
Claim 23
Dependent Claim
16 words
The method of claim 17 wherein the temperature is of the order of about -80° C.
Claim 24
Dependent Claim
24 words
The method of claim 11 wherein there is added a cocatalyst selected from the group consisting of acetic acid, a phenol, HCl and water.
References Cited (Backward Citations)
US2831898A
Cited
US2984648A
Cited
US2975217A
Cited
US3496128A
Cited
US3502629A
Cited
US3453731A
Cited
US3477991A
Cited
US3953402A
Cited
US3962187A
Cited
US3993714A
Cited
US4010140A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-14 | 1982-02-13 | 1982-08-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-14 | 1986-02-13 | 1986-08-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-14 | 1990-02-13 | 1990-08-15 | $7700.00 | Window Closed / Lapsed |