US4022954A
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Novel polymer containing cyclopentanylvinylene units
Assignee: Resonac Holdings Corp
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Filing: 1975-07-01
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Granted: 1977-05-10
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Expires: 1995-07-01
Abstract
Abstract Processes for preparing novel polymers containing carboxyl or carboxylate groups which comprises hydrolyzing starting polymers containing acid anhydride groups in the presence of acids or alkalies, the starting polymers being prepared by ring-opening polymerization of acid anhydride-type norbornene derivatives, and the characteristics and utility of these novel polymers are disclosed.
Inventors
- 👤 Shigeru Kurosawa
- 👤 Takashi Ueshima
- 👤 Yasuzi Tanaka
- 👤 Shoichi Kobayashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:39
CPC Classifications
C; C08; C08L; C08L65/00; C08F; C08F8/00; C08F8/12; C08F8/44; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08; Y; Y10; Y10T; Y10T428/00; Y10T428/26; Y10T428/266; Y10T428/31504; Y10T428/31678; Y10T428/31692; Y10T428/31855; Y10T428/3188
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
629 words
A homopolymer or copolymer comprising recurring units of the following formula ##STR22## wherein Z is bonded to a carbon of a five-membered ring by any two of bonds a to d, the remaining two bonds being filled by R 1 and R 2 , and Z represents ##STR23## R 1 to R 6 , independently from each other, represent a hydrogen atom or an alkyl group containing 1 to 6 carbon atoms; and endomethylene linkage can exist between the carbon atom to which R 3 is attached and the carbon atom to which R 4 is attached; q is 0 or 1; m and n, independently from each other, are 0, 1 or 2. and M represents a hydrogen atom or a positive ion selected from the group consisting of alkali metals, alkaline earth metals and quaternary ammonium, with the proviso that at least 1 mole % of the existing M is the above ion other than hydrogen; the degree of polymerization of said homopolymer or copolymer being about 10 to 10,000; and said copolymer being composed of more than 1 mole % of the unit of the formula (I) or (I') and less than 99 mole % of one biradical unit selected from the following groups: a. units of the following formula ##STR24## wherein X 1 , X 2 , X 3 and X 4 independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 20 carbon atoms, polar group selected from the group consisting of cyano, ester, ether, halogen, amido and imido, or a hydrocarbon radical containing 1 to 20 carbon atoms and substituted by one said polar group, with the proviso that at least one of X 1 , X 2 , X 3 and X 4 is the polar group, the hydrocarbon substituted by the polar group, or an aryl radical group containing 6 to 20 carbon atoms; b. units of the following formula ##STR25## wherein X 5 and X 6 , independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 10 carbon atoms, an ester radical, or a hydrocarbon radical containing 1 to 10 carbon atoms substituted by an ester radical, and at least one of X 5 and X 6 is the ester radical or the ester-substituted hydrocarbon radical containing 1 to 10 carbon atoms; c. units of the following formula ##STR26## wherein X 7 , X 8 , X 9 and X 10 , independently from each other, represent a hydrocarbon radical containing 1 to 20 carbon atoms, and at least one of X 7 , X 8 , X 9 and X 10 is an aryl or alkaryl radical containing 6 to 20 carbon atoms; d. units of the following formula ##STR27## wherein X 11 represents a hydrocarbon radical containing 1 to 10 carbon atoms or an ester group-containing radical containing 3 to 21 carbon atoms, and Z, q, m and n are the same as defined above; e. units of the following formula ##STR28## wherein X 12 , X 13 , X 14 and X 15 , independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 10 carbon atoms, a polar group selected from the group consisting of cyano, ester and halogen, or a hydrocarbon radical containing 1 to 10 carbon atoms and substituted by one said polar group; e. units of the following formula ##STR29## wherein X 16 , X 17 , X 18 , X 19 , X 20 and X 21 are the same as X 12 , X 13 , X 14 and X 15 ; g. units of a monoolefinic hydrocarbon containing 4 to 20 carbon atoms; and h. units of a non-conjugated diene group containing 6 to 20 carbon atoms.
Claim 2
Dependent Claim
629 words
A homopolymer or copolymer comprising recurring units of the following formula ##STR22## wherein Z is bonded to a carbon of a five-membered ring by any two of bonds a to d, the remaining two bonds being filled by R 1 and R 2 , and Z represents ##STR23## R 1 to R 6 , independently from each other, represent a hydrogen atom or an alkyl group containing 1 to 6 carbon atoms; and endomethylene linkage can exist between the carbon atom to which R 3 is attached and the carbon atom to which R 4 is attached; q is 0 or 1; m and n, independently from each other, are 0, 1 or 2. and M represents a hydrogen atom or a positive ion selected from the group consisting of alkali metals, alkaline earth metals and quaternary ammonium, with the proviso that at least 1 mole % of the existing M is the above ion other than hydrogen; the degree of polymerization of said homopolymer or copolymer being about 10 to 10,000; and said copolymer being composed of more than 1 mole % of the unit of the formula (I) or (I') and less than 99 mole % of one biradical unit selected from the following groups: a. units of the following formula ##STR24## wherein X 1 , X 2 , X 3 and X 4 independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 20 carbon atoms, polar group selected from the group consisting of cyano, ester, ether, halogen, amido and imido, or a hydrocarbon radical containing 1 to 20 carbon atoms and substituted by one said polar group, with the proviso that at least one of X 1 , X 2 , X 3 and X 4 is the polar group, the hydrocarbon substituted by the polar group, or an aryl radical group containing 6 to 20 carbon atoms; b. units of the following formula ##STR25## wherein X 5 and X 6 , independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 10 carbon atoms, an ester radical, or a hydrocarbon radical containing 1 to 10 carbon atoms substituted by an ester radical, and at least one of X 5 and X 6 is the ester radical or the ester-substituted hydrocarbon radical containing 1 to 10 carbon atoms; c. units of the following formula ##STR26## wherein X 7 , X 8 , X 9 and X 10 , independently from each other, represent a hydrocarbon radical containing 1 to 20 carbon atoms, and at least one of X 7 , X 8 , X 9 and X 10 is an aryl or alkaryl radical containing 6 to 20 carbon atoms; d. units of the following formula ##STR27## wherein X 11 represents a hydrocarbon radical containing 1 to 10 carbon atoms or an ester group-containing radical containing 3 to 21 carbon atoms, and Z, q, m and n are the same as defined above; e. units of the following formula ##STR28## wherein X 12 , X 13 , X 14 and X 15 , independently from each other, represent a hydrogen atom, a hydrocarbon radical containing 1 to 10 carbon atoms, a polar group selected from the group consisting of cyano, ester and halogen, or a hydrocarbon radical containing 1 to 10 carbon atoms and substituted by one said polar group; e. units of the following formula ##STR29## wherein X 16 , X 17 , X 18 , X 19 , X 20 and X 21 are the same as X 12 , X 13 , X 14 and X 15 ; g. units of a monoolefinic hydrocarbon containing 4 to 20 carbon atoms; and h. units of a non-conjugated diene group containing 6 to 20 carbon atoms.
Claim 3
Dependent Claim
29 words
The homopolymer or copolymer of claim 1 which has a reduced viscosity, measured in dimethyl formamide at 30° C. in a concentration of 0.2 g/l, of 0.05 to 20.
Claim 4
Dependent Claim
8 words
The copolymer of claim 1 which is gel-like.
Claim 5
Dependent Claim
63 words
The copolymer of claim 1 which is water-soluble and in which the proportion of the recurring units of formula (I') is at least 40 mole %, and the product of the proportion in mole % of the recurring units of formula (I') multiplied by the proportion in mole % of the positive ion M present in said recurring units is at least 50.
Claim 6
Dependent Claim
36 words
The homopolymer or copolymer of claim 1 which has a reduced viscosity, measured in a 1% by weight aqueous solution of sodium carbonate at 30° C. in a concentration of 0.2 g/dl of 0.05 to 25.
Claim 7
Dependent Claim
37 words
The homopolymer of claim 1 which comprises recurring units of the following formula ##STR30## and which has a reduced viscosity, measured in dimethyl formamide at 30° C. in a concentration of 0.2 g/dl, of 0.05 to 20.
Claim 8
Dependent Claim
44 words
The homopolymer of claim 1 which comprises recurring units of the following formula ##STR31## and which has a reduced viscosity, measured in a 0.2% by weight aqueous solution of sodium carbonate at 30° C. in a concentration of 0.29 g/dl, of 0.05 to 25.
Claim 9
Dependent Claim
85 words
The polymer of claim 1 which comprises recurring units of the following formula ##STR32## wherein M represents a hydrogen atom or a positive ion selected from the group consisting of Li + , Na + , K + , ##STR33## in which R 1 , R 2 and R 3 are identical or different, hydrocarbon radicals having not more than 10 carbon atoms in total, with the proviso that at least 1 mole % of the existing M is the above ion other than hydrogen.
Claim 10
Dependent Claim
12 words
The polymer of claim 8 in which M represents H and Na.
Claim 11
Dependent Claim
52 words
The copolymer of claim 1 selected from the group consisting of ##STR34## wherein m represents a mole % of more than 1 and less than 100, and n represents a mole % of less than 99 and more than 0, and R is a hydrocarbon radical containing 1 to 20 carbon atoms.
Claim 12
Dependent Claim
38 words
Copolymers (A), (B), (C) and (D) of claim 10 which are soluble in dimethyl formamide and have a reduced viscosity, measured in the above solvent at 30° C. in a concentration of 0.2 g/dl, of 0.05 to 20.
Claim 13
Dependent Claim
51 words
Copolymers (A), (B), (C) and (D) of claim 10 which are insoluble in dimethyl formamide, but are soluble in a 1% by weight sodium carbonate aqueous solution, and have a reduced viscosity, measured in the above aqueous solution at 30° C in a concentration of 0.2 g/dl, of 0.05 to 25.
Claim 14
Dependent Claim
64 words
Copolymers (A), (B), (C) and (D) of claim 10 which are insoluble in each of dimethyl pormamide and a 1% by weight Na 2 CO 3 aqueous solution, and have a softening temperature below 200° C, and furthermore have characteristic absorption in infrared spectra at 2610 and 1730 cm - 1 attributable to carboxyl and 1600 - 1400 cm - 1 attributable to carboxylate.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-09 | 1980-11-08 | 1981-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-09 | 1984-11-08 | 1985-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-09 | 1988-11-08 | 1989-05-10 | $7700.00 | Window Closed / Lapsed |