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United States Patent (19) (11) 4,065,435 Sakaguchi Et Al

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United States Patent (19) (11) 4,065,435 Sakaguchi Et Al United States Patent (19) (11) 4,065,435 Sakaguchi et al. 45) Dec. 27, 1977 (54) WATER-SOLUBLE POLYMERS AND (57) ABSTRACT PROCESS FOR PRODUCING THE SAME Water-soluble oxidation-reduction polymers containing 75) Inventors: Shinji Sakaguchi; Shinichi Imai; Junn therein recurring units of the formula (I): Yamaguchi; Nobuo Tsuji, all of Minami-ashigara, Japan i. (I) 73) Assignee: Fuji Photo Film Co., Ltd., -CH-C- Minami-ashigara, Japan =o -o OH (21) Appl. No.: 694,424 O N-R M (22 Filed: June 9, 1976 R Related U.S. Application Data OH 62 Division of Ser. No. 535,657, Dec. 23, 1974, abandoned. or recurring units of formula (II): 30 Foreign Application Priority Data R2 (II) Dec. 21, 1973 Japan .................................... 48-311 H 51) Int. C.’........................... Co8F8/00; C08F 8/28; OH C08F 8/30 f=o -o 52 U.S.C. ................................. 260/47 UP; 526/15; O Nan R 526/46; 526/49 M 58) Field of Search .................................... 260/47 UP R 56) References Cited OH U.S. PATENT DOCUMENTS 2,710,801 6/1955 Minsk et al. .................... 260/47 UP wherein X represents a hydrogen atom, a halogen atom, 3,032,522 5/1962 Summers ............................. 260/29.6 an alkyl group, an allyl group or an aryl group; R1 3,267,073 8/1966 Kun .............. ... 260/47 UP represents a hydrogen atom or an alkyl group; R2 repre 3,488,329 1/1970 Johnson ............................ 260/112.5 sents a hydrogen atom, an alkyl group or an aryl group; 3,877,946 4/1975 Tsuji et al. ........................... 96/87 R R3 represents a divalent group; and M represents a cat 3,879,205 4/1975 Fitzgerald .............................. 96/14 ion. These polymers have excellent oxidation-reduction Primary Examiner-Herbert J. Lilling properties, Attorney, Agent, or Firm-Sughrue, Rothwell, Mion, Zinn and Macpeak 10 Claims, No Drawings 1. 4,065,435 U.S. Pat. No. 2,816,028 discloses polymers, which WATER-SOLUBLE POLYMERS AND PROCESS contain hydroquinone derivatives in their side chains, of FOR PRODUCING THE SAME the general formula: CH-R-CH CH-R-CH COOH OH -)OH wherein R represents B B B 20 This is a Division of application Ser. No. 535,657, -ch-- -ch-- o --CH,- filed Dec. 23, 1974, and now abandoned. loot; b booh looh BACKGROUND OF THE INVENTION A &H, 1. Field of the Invention 25 The present invention relates to water-soluble poly mers. More particularly, the present invention relates to A represents a hydrogen atom, an alkyl group or a novel water-soluble oxidation-reduction polymers hav halogen atom; B represents a hydrogen atom or an alkyl ing hydroquinone structures attached to the side chains group; Z represents -O- or -NH-; x and y each of the polymers and to processes for producing the 30 represents a positive integer of 50 to 2,000; and n repre SaC. sents a positive integer of 1 to 6. 2. Description of the Prior Art The above-described polymers are, however, water Studies of polymers having oxidizing and reducing insoluble except for those polymers where R is functions have been made with the objects of utilizing such polymers as an organic oxidant, a monomer stabi 35 lizer, an electron exchanger for a battery, or an agent for preparing hydrogen peroxide, removing oxygen --CH,- contained in water, treating water or waste water in COOH industry and the like. (See U.S. Pat. Nos. 2,992,899; 2,703,792 and 2,831,045; British Pat. Nos. 891,467 and and hence possess only small oxidation-reduction ca 949,302; Ann. N.Y. Acad. Sci, 57 646 (1959) and Natl. pacities. The polymers in which R is Acad. Sci., U.S., 38934 (1952).) These oxidation-reduction polymers contain, as the B functional group having oxidizing and reducing proper ties, hydroquinone groups, thiol groups, ketone groups, 45 pyridine groups or ferrocene groups. Of these func --CH,-booH tional groups, however, hydroquinones are advanta geous for a variety of reasons, e.g., excellent oxidation are prepared using, as a starting material, poly(acrylic and reduction reversibility, appropriate oxidation or methacrylic anhydride), which are obtained by poly reduction potentials, stability and diversity of methods 50 merizing acrylic or methacrylic anhydride. However, it for their preparation, as described in large numbers of is extremely difficult to obtain soluble poly(acrylic or patents and literature references, e.g., U.S. Pat. Nos. methacrylic anhydride), because the polymerization 3,173,892 and 3,165,492; French Patent Nos. 1,362,707; reaction of acrylic or methacrylic anhydride, each of 1,362,708 and 1,336,713; K. A. Kun and H. G. Cassidy, which contains two double bonds having identical reac J. Polymer Sci., 44383 (1960); ibid., 56.83 (1962); R. E. 55 tivity, is inevitably accompanied by a cross-linking re Moser et al., ibid., A2 2401 (1964); N. Nakabayashi, action which results in the formation of insoluble gels. ibid., A-1, 6869 (1968); G. Wegner, N. Nakabayashi and Moreover, the above-described polymers are not useful H. G. Cassidy, J. Org, Chem, 32 3155 (1967); G. Weg as an additive for photographic materials. This is ner et al., J. Polymer Sci, A-1, 6 3155 (1968); H. thought to be due to the reduced oxidizing and reducing Kamogawa, ibid., B-3, 283 (1965); K. A. Kun et al., properties as a result of the electron-attracting carbonyl ibid., A3 1833 (1965); ibid., 4A-1, 847 and 859 (1966), groups attached directly to the hydroquinone nuclei of etc. the polymers. These known polymers, however, are insoluble or poorly soluble in water and have only small oxidizing SUMMARY OF THE INVENTION and reducing capacities as described, e.g., in H. G. Cas 65 An object of the present invention is to provide sidy and K. A. Kun, Oxidation-Reduction Polymers, water-soluble oxidation-reduction polymers. Interscience, New York (1965). In addition, their prepa Another object of the present invention is to provide rations are highly complicated. polymers which are useful in photography. 4,065,435 3. 4. A still further object of the present invention is to provide polymers which are useful in the production of DETAILED DESCRIPTION OF THE hydrogen peroxide, monomer stabilization, removal of INVENTION oxygen contained in water, treatment of water or waste The hydroquinones or their salts represented by the water in industry and the like. 5 formula (III) can be obtained by the methods described, Another object of the present invention is to provide e.g., in U.S. Pat. Nos. 3,062,884; 3,134,764 and a novel and convenient process for producing polymers 3,187,046; or in U.S. Patent Application Ser. No. 524,835, filed Nov. 18, 1974, (corresponding to Japanese having hydroquinone groups in their side chains. Patent Application No. 128986/1973). Still another object of the present invention is to 10 In the above general formulas, suitable examples of provide additives capable of preventing color contami alkyl groups for X are alkyl groups such as a methyl nation. group, a tert-butyl group, a 1,1,3,3-tetramethylbutyl The polymers of the present invention can be repre group, etc. Suitable examples of aryl groups for X are sented as polymers containing therein recurring units of aryl groups such as a phenyl group, a naphthyl group, a the general formula (I) or (II): 15 halogenated aryl group (e.g., a bromophenyl group, a chlorophenyl group, etc.), etc. Suitable examples of . (I) alkyl groups for R1 are alkyl groups such as a methyl -CH-C- group, an ethyl group, etc. Suitable examples of alkyl OH groups for R2 are alkyl groups having 1 to 2 carbon =o -o 20 atoms such as a methyl group and suitable examples of O N-R aryl groups for R2 are aryl groups such as a phenyl M X group. Suitable examples of divalent groups for R3 are R divalent groups such as a straight chain alkylene group having from 1 to 8 carbon atoms, a branched chain OH 25 alkylene group having from 1 to 8 carbon atoms, an R (II) arylene group or a group having the formula H OH =o -o 30 O N-R --CH g M X R OH wherein n is an integer of 1 to 4. Suitable examples of 35 straight chain alkylene groups for R3 are alkylene wherein X represents a hydrogen atom, a halogen atom groups such as -CH2-, -(CH2)2-, -(CH2)3-, etc., such as chlorine, bromine, etc., an alkyl group having and suitable examples of branched chain alkylene preferably from 1 to 8 carbon atoms, an allyl group or groups for R3 are -CH(CH3)-CH2- and an aryl group; R1 represents a hydrogen atom or an -CH(CH3)CHCH-. Suitable examples of arylene alkyl group having preferably from to 8 carbon atoms; groups for R3 are arylene groups having the formula R2 represents a hydrogen atom, an alkyl group or an aryl group; R3 represents a divalent group; M represents a cation. The polymers of the present invention can be pre 45 pared by reacting a hydroquinone compound or a salt thereof having the general formula (III): Suitable examples of substituents which can be present OH (III) on the above described groups for R3 include an alkyl 50 group (e.g., a methyl group, etc.), an alkoxy group (e.g., a methoxy group, etc.) and a halogen atom (e.g., a chlo rine atom, etc.). Suitable examples of M are a hydrogen atom, an alkali metal atom (e.g., a sodium atom, a potas sium atom, etc.) and a quaternary ammonium group X OH 55 (e.g., HN+(CH3) and HN+(CH3)).
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