US4628077A
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US
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Preparation of polyamide with catalyst comprising transition metal attached to a ligand which contains electron withdrawing groups
Assignee: Standard Oil Co
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Filing: 1985-11-01
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Granted: 1986-12-09
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Expires: 2005-11-01
Abstract
Abstract A novel transition metal complex catalyst comprised of a transition metal attached to a ligand containing electron withdrawing substituents is employed in a polymerization process for producing nylon type polyamides.
Inventors
- 👤 Michael J. Desmond
- 👤 Raymond J. Weinert, Jr.
- 👤 Lawrence E. Ball
- 👤 Kenneth C. Benton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:12
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/04; C08G69/08; C08G69/14; C08G69/16; C08G69/18; C08G69/20; C08G69/26; C08G69/28
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
102 words
A process for producing a nylon type polyamide, containing a plurality of ##STR11## amide groups as integral parts of the main polymer chain, comprising contacting at a temperature sufficient to cause polymerization, at least one polyamide forming reactant with a transition metal complex catalyst, wherein the catalyst comprises at least one transition metal attached to a ligand containing electron withdrawing substituents wherein the electron withdrawing substituents are selected from the group consisting of --F, --Cl, --Br, --I, --CF 3 , ##STR12## --CN, --NH 3 + , --NO 2 , and --NR 3 + where R is an alkyl or an aryl radical.
Claim 2
Dependent Claim
102 words
A process for producing a nylon type polyamide, containing a plurality of ##STR11## amide groups as integral parts of the main polymer chain, comprising contacting at a temperature sufficient to cause polymerization, at least one polyamide forming reactant with a transition metal complex catalyst, wherein the catalyst comprises at least one transition metal attached to a ligand containing electron withdrawing substituents wherein the electron withdrawing substituents are selected from the group consisting of --F, --Cl, --Br, --I, --CF 3 , ##STR12## --CN, --NH 3 + , --NO 2 , and --NR 3 + where R is an alkyl or an aryl radical.
Claim 3
Dependent Claim
30 words
The process of claim 1, where the transition metal in the catalyst is selected from the group consisting of cobalt, molybdenum, nickel, copper, iron, manganese, ruthenium, chromium, vanadium and rhodium.
Claim 4
Dependent Claim
24 words
The process of claim 2, where the transition metal in the catalyst is selected from the group consisting of cobalt, molybdenum, nickel and copper.
Claim 5
Dependent Claim
23 words
The process of claim 1, where the valence state of the transition metal in the catalyst is greater than or equal to +2.
Claim 6
Dependent Claim
18 words
The process of claim 1, where the ligand is organic and has a net negative or neutral charge.
Claim 7
Dependent Claim
19 words
The process of claim 1, where the electron withdrawing substituents attached to the ligand have a positive Hammet coefficient.
Claim 8
Dependent Claim
18 words
The process of claim 1, where the ligand is organic and has a net negative or neutral charge.
Claim 9
Dependent Claim
18 words
The process of claim 6, where the organic ligand includes oxygen, nitrogen, sulfur, phosphorus, arsenic or mixtures thereof.
Claim 10
Dependent Claim
31 words
The process of claim 8, where the ligand is selected from the group consisting of ##STR13## where X is an electron withdrawing substituent and R is an alkyl or aryl group.
Claim 11
Dependent Claim
32 words
The process of claim 1 where the transition metal complex catalyst is selected from the group of consisting of cobalt (II) trifluoroacetylacetonate, cobalt (III) trifluoroacetylacetonate, cobalt (II) hexafluoroacetylacetonate and cobalt (III) hexafluoroacetylacetonate.
Claim 12
Dependent Claim
76 words
The process of claim 1, where the transition metal complex catalyst is employed in conjunction with a cocatalyst selected from the group consisting of: (a) di-sec-butylmagnesium; (b) n-butylmagnesium chloride; (c) aluminum triethyl and (d) compounds of the formula: (R.sup.VI).sub.n AlX.sub.(3-n) where R VI is at least one of an aliphatic, cycloaliphatic or aromatic radical of 1 to 8 carbon atoms, X is halide and n is less than or equal to 3 but greater than 0.
Claim 13
Dependent Claim
33 words
The process of claim 11, where R VI , in the cocatalyst of the formula (R VI ) n AlX.sub.(3-n), is at least one of an alkyl, aryl, arylalkyl, alkenyl, or arylalkenyl radical.
Claim 14
Dependent Claim
25 words
The process of claim 12, where R VI is at least one of an ethyl, isopropyl, sec-butyl, isobutyl, cyclohexyl, phenyl, benzyl, 1-octenyl or 1-phenyl-1-heptenyl radical.
Claim 15
Dependent Claim
27 words
The process of claim 11, where X, in the cocatalyst of the formula (R IV ) n AlX.sub.(3-n), is at least one of chlorine, bromine or iodine.
Claim 16
Dependent Claim
9 words
The process of claim 14, where X is chlorine.
Claim 17
Dependent Claim
28 words
The process of claim 11, where the cocatalyst of the formula (R VI ) n AlX.sub.(3-n) is at least one of ethylaluminum dichloride, ethylaluminum sesquichloride or diethylaluminum chloride.
Claim 18
Dependent Claim
24 words
The process of claim 11 where the mole ratio of the cocatalyst to the transition metal complex catalyst is between approximately 1:1 and 300:1.
Claim 19
Dependent Claim
25 words
The process of claim 11 where the ratio of the organometallic compound cocatalyst to the transition metal complex catalyst is between approximately 3:1 and 50:1.
Claim 20
Dependent Claim
34 words
The process of claim 1, where the polyamide forming reactant is at least one of (1) an alpha, beta-unsaturated carboxylic acid and ammonia or (2) an ammonium salt of an alpha, beta-unsaturated carboxylic acid.
Claim 21
Dependent Claim
47 words
The process of claim 19 where the alpha,beta-carboxylic acid is of the formula ##STR14## where each R' is independently one of hydrogen, C 1 to C 4 alkyl group or a halogen and R" is one of hydrogen or a C 1 to C 10 alkyl group.
Claim 22
Dependent Claim
19 words
The process of claim 20 where the alpha,beta-carboxylic acid is at least one of acrylic acid or crotonic acid.
Claim 23
Dependent Claim
51 words
The process of claim 19 where the ammonium salt of the alpha,beta-unsaturated carboxylic acid is of the formula: ##STR15## where each R' is independently one of hydrogen, C 1 to C 4 alkyl or a halogen and R" is one of hydrogen of a C 1 to C 10 alkyl group.
Claim 24
Dependent Claim
21 words
The process of claim 22 where the ammonium salt of the alpha,beta-unsaturated carboxylic acid contains between 3 and 7 carbon atoms.
Claim 25
Dependent Claim
24 words
The process of claim 23 where the ammonium salt of the alpha,beta-unsaturated carboxylic acid is at least one of ammonium acrylate or ammonium methacrylate.
Claim 26
Dependent Claim
19 words
The process of claim 1, where the temperature sufficient to cause polymerization is between 100° C. and 300° C.
References Cited (Backward Citations)
US4283524A
Cited
US4459394A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-12-08 | 1990-06-09 | 1990-12-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-12-08 | 1994-06-09 | 1994-12-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-12-08 | 1998-06-09 | 1998-12-09 | $7700.00 | Window Closed / Lapsed |