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US4098991A Expired / Lapsed US ⏱️ 0.0 years remaining

Removal of catalytic residues from hydrogenated thermoplastic or elastomeric polymers

Assignee: Bridgestone Firestone Inc
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Filing: 1977-02-25
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Granted: 1978-07-04
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Expires: 1997-02-25
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Abstract

Abstract A process for the removal of catalytic residues from hydrogenated thermoplastic or elastomeric polymers is achieved by treating the residue with an amine compound. The amine compound is selected from the class consisting of an HCl salt of an amine or a diamine having an alkyl group containing from 1 to 12 carbon atoms, a cycloalkyl group containing from 4 to 12 carbon atoms, an aryl group containing from 6 to 12 carbon atoms, and combinations thereof; a substituted glyoxime wherein the substituted group is selected from the class consisting of an alkyl having from 1 to 12 carbon atoms, a cycloalkyl having from 4 to 6 carbon atoms, an aryl having from 6 to 12 carbon atoms, and combinations thereof; and the heterocyclic nitrogen compounds of pyrrole and pyridine.

Inventors

  • 👤 Jung Wong Kang

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:15
CPC Classifications
C; C08; C08F; C08F6/00; C08F6/02; C08C; C08C2/00; C08C2/02; C08C2/04; Y; Y10; Y10S; Y10S528/00; Y10S528/931

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 153 words
A process for the removal of a metal catalytic residue, comprising; precipitating a metal catalytic residue of a hydrogenated polymer by reacting said metal catalytic residue with an amine compound, said metal catalytic residue selected from the class consisting of nickel, cobalt and iron, said amine compound selected from the class consisting of, an HCl salt of an amine, said amine selected from the class consisting of an amine having an alkyl group selected from the class consisting of ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, and an amine having a phenyl group, an HCl salt of a diamine having an alkyl group selected from the class consisting of ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, or a phenyl group, a substituted glyoxime compound selected from the class consisting of methylglyoxime, phenylmethylglyoxime, dimethylglyoxime and diphenylglyoxime, and a heterocyclic nitrogen compound selected from the class consisting of pyrrole and the HCl salt of pyridine.
Claim 2
Dependent Claim 153 words
A process for the removal of a metal catalytic residue, comprising; precipitating a metal catalytic residue of a hydrogenated polymer by reacting said metal catalytic residue with an amine compound, said metal catalytic residue selected from the class consisting of nickel, cobalt and iron, said amine compound selected from the class consisting of, an HCl salt of an amine, said amine selected from the class consisting of an amine having an alkyl group selected from the class consisting of ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, and an amine having a phenyl group, an HCl salt of a diamine having an alkyl group selected from the class consisting of ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, or a phenyl group, a substituted glyoxime compound selected from the class consisting of methylglyoxime, phenylmethylglyoxime, dimethylglyoxime and diphenylglyoxime, and a heterocyclic nitrogen compound selected from the class consisting of pyrrole and the HCl salt of pyridine.
Claim 3
Dependent Claim 34 words
A process for the removal of a metal catalytic residue according to claim 1, wherein the amount of amine compound to said metal catalytic residue is in a stoichiometric excess of at least two.
Claim 4
Dependent Claim 32 words
A process for the removal of a metal catalytic residue according to claim 2, wherein said stoichiometric excess of said amine compound to said metal catalytic residue ranges from 2 to 10.
Claim 5
Dependent Claim 83 words
A process for the removal of a metal catalytic residue according to claim 3, wherein the hydrogenated polymer is selected from the class consisting of natural rubber, a homopolymer, and a copolymer, said homopolymer made from a monomer selected from the class consisting of dienes having from 3 to 12 carbon atoms and alkynes having from 3 to 12 carbon atoms, and said copolymers made from various combinations of monomers containing at least 1 diene monomer having from 3 to 12 carbon atoms.
Claim 6
Dependent Claim 74 words
A process for the removal of a metal catalytic residue according to claim 4, wherein the hydrogenated polymer is selected from the class consisting of natural rubber, a homopolymer, and a copolymer, said homopolymer is made from monomers selected from the class consisting of propadiene, 1,3-butadiene, isoprene, piperylene, 1,5-hexadiene, 1,5-heptadiene, acetylene, 1,5-hexadiyne, 2,4-hexadiyne, and 1,4-octadiene; said copolymer is made from monomers selected from the class consisting of butadiene-isoprene, butadiene-propylene, isoprene-styrene, butadiene-ethylene, alpha-methylstyrene-butadiene and styrene-butadiene.
Claim 7
Dependent Claim 36 words
A process for the removal of a metal catalytic residue according to claim 5, wherein said amine compounds are reacted with said metal catalytic residue at a temperature of from about 25° to about 150° C.
Claim 8
Dependent Claim 21 words
A process for the removal of a metal catalytic residue according to claim 6, including separating said precipitated metal catalytic residue.
Claim 9
Dependent Claim 21 words
A process for the removal of a metal catalytic residue according to claim 7, wherein said separation is achieved by filtration.
Claim 10
Dependent Claim 34 words
A process for the removal of a metal catalytic residue according to claim 8, wherein said precipitated metal catalytic residue is washed with a compound selected from the class consisting of water and alcohol.
Claim 11
Dependent Claim 209 words
A process for the removal of a metal catalytic residue from a hydrogenated polymer, comprising; precipitating the metal catalytic residue of the hydrogenated polymer by reacting said catalytic residue with an amine compound selected from the class consisting of, an HCl salt of an amine, said amine selected from the class consisting of an alkyl amine containing from 1 to 12 carbon atoms, a cycloalkyl amine containing from 4 to 12 carbon atoms, an aryl amine containing from 6 to 12 carbon atoms, and combinations thereof, an HCl salt of a diamine, said diamine selected from the class consisting of an alkyl diamine having from 1 to 12 carbon atoms, a cycloalkyl diamine having from 4 to 12 carbon atoms, an aryl diamine having from 6 to 12 carbon atoms, and combinations thereof, a substituted glyoxime, said substituted group selected from the class consisting of an alkyl containing from 1 to 12 carbon atoms, a cycloalkyl containing from 4 to 12 carbon atoms, an aryl containing from 6 to 12 carbon atoms, and combinations thereof, a heterocyclic nitrogen compound selected from the class consisting of pyrrole and the HCl salt of pyridine, and said catalytic residue containing a metal selected from the class consisting of nickel, cobalt and iron.
Claim 12
Dependent Claim 209 words
A process for the removal of a metal catalytic residue from a hydrogenated polymer, comprising; precipitating the metal catalytic residue of the hydrogenated polymer by reacting said catalytic residue with an amine compound selected from the class consisting of, an HCl salt of an amine, said amine selected from the class consisting of an alkyl amine containing from 1 to 12 carbon atoms, a cycloalkyl amine containing from 4 to 12 carbon atoms, an aryl amine containing from 6 to 12 carbon atoms, and combinations thereof, an HCl salt of a diamine, said diamine selected from the class consisting of an alkyl diamine having from 1 to 12 carbon atoms, a cycloalkyl diamine having from 4 to 12 carbon atoms, an aryl diamine having from 6 to 12 carbon atoms, and combinations thereof, a substituted glyoxime, said substituted group selected from the class consisting of an alkyl containing from 1 to 12 carbon atoms, a cycloalkyl containing from 4 to 12 carbon atoms, an aryl containing from 6 to 12 carbon atoms, and combinations thereof, a heterocyclic nitrogen compound selected from the class consisting of pyrrole and the HCl salt of pyridine, and said catalytic residue containing a metal selected from the class consisting of nickel, cobalt and iron.
Claim 13
Dependent Claim 35 words
A process for the removal of a metal catalytic residue according to claim 10, wherein the amount of said amine compound to said metal catalytic residue is in a stoichiometric excess of at least two.
Claim 14
Dependent Claim 34 words
A process for the removal of a metal catalytic residue according to claim 11, wherein the stoichiometric excess of said amine compound to said metal catalytic residue ranges from about 3.0 to about 10.0.
Claim 15
Dependent Claim 82 words
A process for the removal of a metal catalytic residue according to claim 12, wherein the hydrogenated polymer is selected from the class consisting of natural rubber, a homopolymer, and a copolymer, said homopolymer made from a monomer selected from the class consisting of dienes having from 3 to 12 carbon atoms and alkynes having from 3 to 12 carbon atoms, said copolymers made from various combinations of monomers containing at least one diene monomer having from 3 to 12 carbon atoms.
Claim 16
Dependent Claim 74 words
A process for the removal of a metal catalytic residue according to claim 13, wherein the hydrogenated polymer is selected from the class consisting of natural rubber, a homopolymer, and a copolymer, said homopolymer is made from monomers selected from the class consisting of propadiene, 1,3-butadiene, isoprene, piperylene, 1,5-hexadiene, 1,5-heptadiene, acetylene, 1,5-hexadiyne, 2,4-hexadiyne, and 1,4-octadiene; said copolymer is made from monomers selected from the class consisting of butadiene-isoprene, butadiene-propylene, isoprene-styrene, butadiene-ethylene, alpha-methylstyrene-butadiene and styrene-butadiene.
Claim 17
Dependent Claim 48 words
A process for the removal of a metal catalytic residue according to claim 13, wherein said homopolymer is made from monomers selected from the class consisting of butadiene and isoprene, and said copolymers are made from monomers selected from the class consisting of alpha-methylstyrene-butadiene, butadiene-isoprene, styrene-butadiene and styrene-isoprene.
Claim 18
Dependent Claim 30 words
A process for the removal of a metal catalytic residue according to claim 13, including carrying out said reaction at a temperature of from about 25 to about 50° C.
Claim 19
Dependent Claim 85 words
A process for the removal of a metal catalytic residue according to claim 13, wherein said metal catalytic residue is a trihydrocarbonyl aluminum reduced organonickel compound wherein said aluminum compound has the formula Al(R) 3 where R is an alkyl, a cycloalkyl, or an aryl radical having from 1 to 20 carbon atoms, and combinations thereof, and said nickel compound has the formula ##STR4## where R' is an alkyl, a cycloalkyl, or an aryl radical having from 1 to 20 carbon atoms, and combinations thereof.

References Cited (Backward Citations)

US3037011A Cited
US3071566A Cited
US3258456A Cited
US3780138A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-07-03 1982-01-02 1982-07-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-07-03 1986-01-02 1986-07-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-07-03 1990-01-02 1990-07-04 $7700.00 Window Closed / Lapsed

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