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US4229564A
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Friedel-Crafts polymerization of monomers in the preparation of polyketones and polysulfones
Assignee: Raychem Corp
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Filing: 1976-04-26
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Granted: 1980-10-21
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Expires: 1996-04-26
Abstract
Abstract The molecular weight of highly aromatic polymers made by the Friedel-Crafts polymerization of EN monomers of the formula Ar--L--Ar 1 --X, wherein X is selected from SO 2 Y or COY, Y being a radical selected from --OH, halogen, or alkyl, wherein Ar and Ar 1 are independently ##STR1## wherein L is --CO--, --SO 2 --, phenyleneoxy, --NHCO--, a covalent bond, --O--, or --CR 2 --, wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, phenyl or a phenyl group substituted by an electron withdrawing group such as halogen, NO 2 or --CN, is controlled by including in the reaction mixture an acylatable aromatic compound whose rate of acylation under Friedel-Crafts conditions is at least about 150 times that of benzene. The molecular weight of other polymers made from EN type monomers by Friedel-Crafts catalysis can also be controlled in this way.
Inventors
- 👤 Klaus J. Dahl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 02:13
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/12; C08G61/127; C08G61/02; C08G75/00; C08G75/20; C08G2261/00; C08G2261/10; C08G2261/12; C08G2261/124; C08G2261/30; C08G2261/34; C08G2261/342; C08G2261/3424; C08G2261/344; C08G2261/3442; C08G2261/3444; C08G2261/40; C08G2261/45
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
67 words
A process for producing a polymer comprising polymerizing at least one monomer under Friedel-Crafts conditions, said monomer having both an electrophillic and a nucleophillic reaction center under said Friedel-Crafts conditions, the electrophillic center on one monomer molecule reacting with the nucleophillic center on another to propagate said polymer, in the presence of a molecular weight control agent that reacts only as a nucleophile under the reaction conditions.
Claim 2
Dependent Claim
67 words
A process for producing a polymer comprising polymerizing at least one monomer under Friedel-Crafts conditions, said monomer having both an electrophillic and a nucleophillic reaction center under said Friedel-Crafts conditions, the electrophillic center on one monomer molecule reacting with the nucleophillic center on another to propagate said polymer, in the presence of a molecular weight control agent that reacts only as a nucleophile under the reaction conditions.
Claim 3
Dependent Claim
28 words
A process according to claim 1 wherein the molecular weight control agent is an aromatic compound whose rate of acetylation relative to benzene is greater than about 150.
Claim 4
Dependent Claim
20 words
A process according to claim 2 wherein said molecular weight control agent is a monofunctional nucleophile under the Friedel-Crafts conditions.
Claim 5
Dependent Claim
12 words
A process according to claim 3 wherein said control agent is biphenyl.
Claim 6
Dependent Claim
20 words
A process according to claim 2 wherein said molecular weight control agent is a difunctional nucleophile under the Friedel-Crafts conditions.
Claim 7
Dependent Claim
13 words
A process according to claim 5 wherein the control agent is diphenyl ether.
Claim 8
Dependent Claim
92 words
A process according to claim 1 wherein the monomer is a compound of the formula Ar--L--Ar 1 --X, wherein X is selected from SO 2 Y or COY, Y being a radical selected from --OH, halogen, or alkyl, wherein Ar and Ar 1 are independently ##STR21## wherein L is --CO--, --SO 2 --, phenyleneoxy, --NHCO--, a covalent bond, --O--, or CR 2 --, wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, phenyl or a phenyl group substituted by an electron withdrawing group such as halogen, --NO 2 or --CN.
Claim 9
Dependent Claim
17 words
A process according to claim 7 wherein the monomer is selected from the group consisting of ##STR22##
Claim 10
Dependent Claim
16 words
A process according to claim 8 wherein the Friedel-Crafts polymerization is catalyzed by BF 3 .
Claim 11
Dependent Claim
18 words
A process according to claim 9 wherein the polymerization is carried out in a solvent of hydrogen fluoride.
Claim 12
Dependent Claim
17 words
A process according to claim 7 wherein the monomer is selected from the group consisting of ##STR23##
Claim 13
Dependent Claim
12 words
A process according to claim 11 wherein the catalyst is indium trichloride.
Claim 14
Dependent Claim
18 words
A process according to claim 12 wherein the polymerization is carried out in a solvent of nitro benzene.
Claim 15
Dependent Claim
45 words
A process according to claim 1 wherein the polymerization results in a polymer having a mean inherent viscosity within the range 0.8 to 1.65 at 25° C. for a solution having a concentration of 0.1 g polymer per 100 ml. H 2 SO 4 .
Claim 16
Dependent Claim
46 words
A process according to claim 11 wherein the polymer resulting from the polymerization has a mean inherent viscosity within the range of 0.8 to 1.65 at 25° C. for a solution having a concentration of 0.1 g. polymer per 100 ml. H 2 SO 4 .
Claim 17
Dependent Claim
102 words
A polymer of the structure (NE) x --M wherein (NE) x is a polymer chain of X repeating units derived from the polymerization of a monomer unit EN having both an electrophillic reaction center E and a nucleophillic reaction center N under Friedel-Crafts reaction conditions, the electrophillic center of one monomer unit reacting with the nucleophillic reaction center of another to propagate said polymer chain, and --M is a moiety arising from the reaction of an electrophillic center on said polymer chain with a molecular weight control agent of the formula M-H having a single nucleophillic reaction center under the reaction conditions.
Claim 18
Dependent Claim
102 words
A polymer of the structure (NE) x --M wherein (NE) x is a polymer chain of X repeating units derived from the polymerization of a monomer unit EN having both an electrophillic reaction center E and a nucleophillic reaction center N under Friedel-Crafts reaction conditions, the electrophillic center of one monomer unit reacting with the nucleophillic reaction center of another to propagate said polymer chain, and --M is a moiety arising from the reaction of an electrophillic center on said polymer chain with a molecular weight control agent of the formula M-H having a single nucleophillic reaction center under the reaction conditions.
Claim 19
Dependent Claim
10 words
A polymer according to claim 16 wherein M-- is ##STR24##
Claim 20
Dependent Claim
92 words
A polymer according to claim 16 wherein said monomer is a compound of the formula Ar--L--Ar 1 --X, wherein X is selected from SO 2 Y or COY, Y being a radical selected from --OH, halogen, or alkyl, wherein Ar and Ar 1 are independently ##STR25## wherein L is --CO--, --SO 2 --, phenyleneoxy, --NHCO--, a covalent bond, --O--, or --CR 2 --, wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, phenyl or a phenyl group substituted by an electron withdrawing group such as halogen, --NO 2 or --CN.
Claim 21
Dependent Claim
9 words
A polymer according to claim 18 of formula ##STR26##
Claim 22
Dependent Claim
10 words
A polymer according to claim 18 having the structure ##STR27##
Claim 23
Dependent Claim
15 words
A polymer according to claim 18 of formula selected from the group consisting of ##STR28##
Claim 24
Dependent Claim
38 words
A polymer according to claim 21 having a mean inherent viscosity within the range 0.8 to 1.65 at 25° C. for a solution having a concentration of 0.1 g. polymer per 100 ml. H 2 SO 4 .
Claim 25
Dependent Claim
108 words
A polymer of the structure (NE) x --M'--(EN) y wherein (NE) x and (EN) y are polymer chains of x and y repeating units respectively derived from the polymerization of a monomer unit EN having both an electrophillic reaction center E and a nucleophillic reaction center N under Friedel-Crafts reaction conditions, the electrophillic center of one monomer unit reacting with the nucleophillic reaction center of another to propagate said polymer chain, and --M'--is a moiety arising from the reaction of an electrophillic center on each of said polymer chains with a molecular weight control agent of the formula H--M'--H having two nucleophillic reaction centers under the reaction conditions.
Claim 26
Dependent Claim
108 words
A polymer of the structure (NE) x --M'--(EN) y wherein (NE) x and (EN) y are polymer chains of x and y repeating units respectively derived from the polymerization of a monomer unit EN having both an electrophillic reaction center E and a nucleophillic reaction center N under Friedel-Crafts reaction conditions, the electrophillic center of one monomer unit reacting with the nucleophillic reaction center of another to propagate said polymer chain, and --M'--is a moiety arising from the reaction of an electrophillic center on each of said polymer chains with a molecular weight control agent of the formula H--M'--H having two nucleophillic reaction centers under the reaction conditions.
Claim 27
Dependent Claim
10 words
A polymer according to claim 23 wherein M' is ##STR29##
Claim 28
Dependent Claim
92 words
A polymer according to claim 23 wherein said monomer is a compound of the formula Ar--L--Ar 1 --X, wherein X is selected from SO 2 Y or COY, Y being a radical selected from --OH, halogen, or alkyl, wherein Ar and Ar 1 are independently ##STR30## wherein L is --CO--, --SO 2 --, phenyleneoxy, --NHCO--, a covalent bond, --O--, or --CR 2 --, wherein each R is independently hydrogen, an alkyl or fluoroalkyl group, phenyl or a phenyl group substituted by an electron withdrawing group such as halogen, --NO 2 or --CN.
Claim 29
Dependent Claim
9 words
A polymer according to claim 25 of formula ##STR31##
Claim 30
Dependent Claim
9 words
A polymer according to claim 25 of formula ##STR32##
Claim 31
Dependent Claim
15 words
A polymer according to claim 25 of formula selected from the group consisting of ##STR33##
Claim 32
Dependent Claim
40 words
A polymer according to claim 21 having a mean inherent viscosity within the range from about 0.8 to 1.65 at 25° C. for a solution having a concentration of 0.1 g. polymer per 100 ml. H 2 SO 4 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |