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US4409408A Expired / Lapsed US ⏱️ 0.0 years remaining

Inhibiting polymerization of vinyl aromatic monomers

Assignee: Pony Industries Inc
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Filing: 1982-09-24
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Granted: 1983-10-11
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Expires: 2002-09-24
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Abstract

Abstract Vinyl aromatic compounds are stabilized against undesired polymerization by adding to the vinyl aromatic compounds small amounts of N,N-dialkylhydroxylamine and tertiary alkylcatechols. The synergistic effect of the mixture has been demonstrated.

Inventors

  • 👤 Richard F. Miller

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 02:51
CPC Classifications
C; C07; C07C; C07C7/00; C07C7/20; Y; Y10; Y10S; Y10S585/00; Y10S585/949; Y10S585/95

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 77 words
A composition comprised of (a) a vinyl aromatic compound containing an amount effective to inhibit polymerization of said vinyl aromatic compound of a mixture of (1) about 10 to 90 parts by weight of at least one N,N-dialkylhydroxylamine wherein the alkyl groups are the same or different and each alkyl group has 2 to 10 carbon atoms, and (2) about 90 to 10 parts by weight of at least one tertiary-alkylcatechol having 4 to 20 carbon atoms.
Claim 2
Dependent Claim 77 words
A composition comprised of (a) a vinyl aromatic compound containing an amount effective to inhibit polymerization of said vinyl aromatic compound of a mixture of (1) about 10 to 90 parts by weight of at least one N,N-dialkylhydroxylamine wherein the alkyl groups are the same or different and each alkyl group has 2 to 10 carbon atoms, and (2) about 90 to 10 parts by weight of at least one tertiary-alkylcatechol having 4 to 20 carbon atoms.
Claim 3
Dependent Claim 33 words
The composition of claim 1 wherein the total concentration of said mixture of N,N-dialkylhydroxylamine and tertiary-alkylcatechol in said composition is 0.5 to 1000 ppm, based on the total weight of vinyl aromatic compound.
Claim 4
Dependent Claim 93 words
The composition of claim 1 wherein the vinyl aromatic compound is styrene or alkyl substituted styrene, each alkyl group in (1) has 2 to 6 carbon atoms, the tertiary alkyl group in (2) has 4 to 8 carbon atoms and the relative concentrations of the compounds in (1) and (2) are 25 to 75 parts by weight and 75 to 25 parts by weight respectively and the total concentration of said mixture of N,N-dialkylhydroxylamine and tertiary-alkylcatechol is said composition is 5 to 500 ppm, based on the total weight of vinyl aromatic compound.
Claim 5
Dependent Claim 26 words
The composition of claim 3 wherein the vinyl aromatic compound is styrene, the compound in (1) is N,N-diethylhydroxylamine and the compound in (2) is tertiary butylcatechol.
Claim 6
Dependent Claim 106 words
In a method of inhibiting polymerization of a vinyl aromatic compound comprising adding to the vinyl aromatic compound an amount of an polymerization inhibiting agent effective to substantially reduce the rate of polymerization, the improvement comprising using as the agent a combination of: (a) about 10 to 90 parts of at least one N,N-dialkylhydroxylamine wherein the alkyl groups are the same or different and each alkyl group has 2 to 10 carbon atoms, and (b) about 90 to 10 parts of at least one tertiary alkylcatechol having 4 to 20 alkyl carbon atoms per 100 total parts by weight of the compounds in 8a) and (b).
Claim 7
Dependent Claim 106 words
In a method of inhibiting polymerization of a vinyl aromatic compound comprising adding to the vinyl aromatic compound an amount of an polymerization inhibiting agent effective to substantially reduce the rate of polymerization, the improvement comprising using as the agent a combination of: (a) about 10 to 90 parts of at least one N,N-dialkylhydroxylamine wherein the alkyl groups are the same or different and each alkyl group has 2 to 10 carbon atoms, and (b) about 90 to 10 parts of at least one tertiary alkylcatechol having 4 to 20 alkyl carbon atoms per 100 total parts by weight of the compounds in 8a) and (b).
Claim 8
Dependent Claim 34 words
The improved method of claim 5 wherein said agent is added to the vinyl aromatic compound in a concentration of about 0.5 to 1000 ppm based on the weight of said vinyl aromatic compound.
Claim 9
Dependent Claim 64 words
The improved method of claim 5 wherein each alkyl group of the compound in (a) has 2 to 6 carbon atoms, the tertiary alkyl group of the compound in (b) has 4 to 8 carbon atoms and said agent is added to the vinyl aromatic monomer in a concentration of about 5 to 500 ppm, based on the weight of said vinyl aromatic compound.
Claim 10
Dependent Claim 20 words
The improved method of claim 7 wherein the compound in (a) is N,N-diethythyhydroxylamine and the compound in (b) is tertiary-butylcatechol.
Claim 11
Dependent Claim 35 words
The improved method of claim 5, 6, 7 or 8 wherein the compounds in (a) and (b) are present in amounts of about 25 to 75 parts and 75 to 25 parts by weight, respectively.

References Cited (Backward Citations)

US3287430A Cited
US2809155A Cited
US2867672A Cited
US3248440A Cited
US3390198A Cited
SU819078A1 Cited
SU763313A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-10-10 1987-04-11 1987-10-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-10-10 1991-04-11 1991-10-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-10-10 1995-04-11 1995-10-11 $7700.00 Window Closed / Lapsed

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