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United States Patent (19) 11 Patent Number: 6,072,024 Irizato Et Al

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United States Patent (19) 11 Patent Number: 6,072,024 Irizato Et Al US006072O24A United States Patent (19) 11 Patent Number: 6,072,024 Irizato et al. (45) Date of Patent: Jun. 6, 2000 54 PRODUCTION PROCESS OF CROSS Primary Examiner Duc Truong LINKED POLYASPARTIC ACID RESIN Attorney, Agent, or Firm-Burns, Doane, Swecker & 75 Inventors: Yoshihiro Irizatio; Makoto Sukegawa, Mathis, L.L.P. both of Kanagawa; Toshio Katoh, Saitama; Hiroaki Tamatani, Kanagawa; 57 ABSTRACT Akinori Nagatomo; Masaru Wada, both of Fukuoka, all of Japan A process is disclosed for producing with good productivity a croSS-linked polyaspartic acid resin having biodegradabil 73 Assignee: Mitsui Chemicals, Inc., Japan ity and high water absorbency. The process features inclu Sion of one of the following Steps: (a) a poly Succinimide, 21 Appl. No.: 09/042,942 which has been brought into a dispersed State by a 22 Filed: Mar 17, 1998 dispersant, and a cross-linking agent are reacted to produce 30 Foreign Application Priority Data the cross-linked polyaspartic acid resin; (b) imide rings of a croSS-linked poly Succinimide are Subjected to a hydrolysis Mar. 21, 1997 JP Japan .................................... 9-068.185 Mar. 21, 1997 JP Japan ... reaction while controlling a Swelling degree of a resulting Apr. 18, 1997 JP Japan ... gel, whereby the cross-linked polyaspartic acid resin is Apr. 18, 1997 JP Japan ... Apr. 18, 1997 JP Japan ... produced; and (c) a gel of a cross-linked poly Succinimide, Apr. 24, 1997 JP Japan . 9-10770 which has been obtained by reacting a croSS-linking agent to (51) Int. Cl. ............................................... C08G 69/10 a Solution of a poly Succinimide in an organic Solvent, is 52 U.S. Cl. .......................... 528/328; 528/322; 528/332; disintegrated to Subject imide rings of the croSS-linked 528/335; 528/345; 528/363; 528/488; 528/491; polySuccinimide to a hydrolysis reaction, So that the croSS 528/499; 525/420; 525/421; 525/422; 524/457; linked polyaspartic acid resin is produced. The process may 524/475; 524/514; 524/522; 524/538 58 Field of Search ..................................... 528/328,332, also include one or both of the following steps as needed: (d) 528/335,345, 363, 488, 491, 499; 525/420, a gel of the cross-linked polyaspartic acid resin is washed 421, 422; 524/457, 475, 514,522,538 with water and/or a water-miscible organic Solvent; and (e) the poly Succinimide is produced using a basic amino acid as 56) References Cited a croSS-linking agent. U.S. PATENT DOCUMENTS 5,461,085 10/1995 Nagamoto et al. ..................... 521/183 15 Claims, No Drawings 6,072,024 1 2 PRODUCTION PROCESS OF CROSS needed. A cautious attitude towards their use is hence LINKED POLYASPARTIC ACID RESIN desirable. Likewise, non-ionic resins have a potential prob lem of accumulating in Soil due to their undegradable nature BACKGROUND OF THE INVENTION although they do not form complexes. It is therefore likely 1. Field of the Invention that they would have adverse effects on the natural world. This invention relates to a process for the production of a Furthermore, these polymerized resins use monomers cross-linked polyaspartic acid resin having (bio) which are highly toxic to human skin and the like. A great degradability and high water absorbency and also to a deal of work has been conducted to eliminate Such mono proceSS for the production of a croSS-linked polySuccinimide mers from polymerized products. Nonetheless, their com plete elimination is difficult. Still higher difficulties are useful as a precursor for the croSS-linked polyaspartic acid expected especially in the production on an industrial Scale. CS. Technical Background of Superabsorbent Polymers Hav 2. Description of the Related Art ing Biodegradability Technical Background of Superabsorbent Polymers On the other hand, biodegradable polymers have been A Superabsorbent polymer is a resin capable of absorbing 15 attracting interest as “globe-compatible materials” in recent water from Several tens of times to Several thousands of years. Their use as Superabsorbent polymerS has also been times its own weight, and is used in Sanitary products, Such proposed. as Sanitary napkins and disposable diapers, and also in a Known examples of biodegradable Superabsorbent poly variety of other fields. merS employed in Such applications include croSS-linked Related Art on Superabsorbent Polymers polyethylene oxide (JP Kokai 6-157795, etc.), cross-linked Known examples of Superabsorbent polymers employed polyvinyl alcohol, croSS-linked carboxymethylcellulose in Such applications include partial neutralization products (U.S. Pat. No. 4,650,716), cross-linked alginic acid, cross of cross-linked polyacrylic acids (JP Kokai No. 55-84304, linked Starches, and cross-linked polyamino acids. Among U.S. Pat. No. 4,625,001), partial hydrolysis products of 25 these, the cross-linked polyethylene oxide and croSS-linked starch-acrylonitrile copolymers (JP Kokai 46-43995), polyvinyl alcohol have Small water absorption and are hence starch-acrylic acid graft copolymers (JP Kokai 51-125468), not particularly Suited for use as materials in products hydrolyzation products of vinyl acetate-acrylate ester requiring high water-absorbency Such as Sanitary products, copolymers (JP Kokai 52-14689), cross-linked copolymers disposable diapers, disposable dustcloths and paper towels. of 2-acrylamido-2-methylpropanesulfonic acid and acrylic Further, these compounds can be biodegraded only by acid (EP0068.189), cross-linked polymers of cationic mono certain particular bacteria, So that under general conditions, mers (U.S. Pat. No. 4,906,717), and hydrolysis products of their biodegradation will be slow or will not take place at all. cross-linked isobutylene-maleic anhydride copolymers Moreover, the biodegradability will be reduced extremely as (U.S. Pat. No. 4,389,513). the molecular weight becomes greater. These Superabsorbent polymers however are accompa 35 In addition, croSS-linked Saccharides Such as cross-linked nied by the problem that they do not degrade following carboxymethylcellulose, cross-linked alginic acid and croSS disposal after use. linked Starches contain many firm hydrogen bonds in their Under the circumstances, these Superabsorbent polymers molecules, thereby exhibiting Strong interaction between are currently disposed of by incineration or reclamation. molecules and/or polymers. Accordingly, molecular chains However, it is indicated that disposal in incinerators is a 40 cannot be opened widely meaning that their water cause of global warming and acid rain in addition to a cause absorbency is not high. of damage to incinerator materials due to heat occurring during incineration. On the other hand, reclamation disposal Technical Background of Polyamino Acid Superabsor is accompanied by problems. Such as poor Stabilization of bent Polymers reclaimed grounds due to the bulky and undegradable nature 45 On the other hand, polymers which are available by of plastics and, moreover, is facing a Serious problem in that croSS-linking polyamino acids do have biodegradability and there are no longer many Sites Suited for reclamation. are thus compatible with the global environment. It has also Described Specifically, these polymers are poor in degrad been found that, even when absorbed in the body, they are ability and remain Semipermanently in water or Soil. Their digested and absorbed by enzymatic action and moreover, disposal presents a very Serious problem from the viewpoint 50 they do not exhibit antigenecity in the body and their of environmental preservation. For example, in the case of metabolites are free of toxicity. These polymers are accord polymers for disposable applications, led by Sanitary prod ingly materials which are also Safe for human beings. ucts Such as disposable diaperS and Sanitary napkins, their As a disclosed example of Such a polymer, a process for recycling, if tried, would require Substantial expenditure the production of a polymer having high water-absorbency, while their incineration, if attempted, would significantly 55 which comprises irradiating Y rays to poly-Y-glutamic acid, affect the global environment due to the enormous quantities was reported by Kunioka et al. in KOBUNSHI RONBUN involved. On the other hand, it has been reported that use of SHU (The Journal of the Society of Polymer Science, a croSS-linked polyacrylic acid resin as an agricultural and Japan), 50(10), 755 (1993). From an industrial viewpoint, horticultural water-holding material leads to the formation however, a 'Co irradiation system for use in this technology of complexes with multivalent ions such as Ca" in soil and 60 requires considerable equipment for Shielding radiation, and hence results in the formation of an insoluble layer Sufficient care is also required for its control. This technol Matsumoto et al., KOBUNSHI (High Polymer, Japan), 42, ogy is therefore not practical. As a further problem, the high August, 1993). Such a layer is considered to have low cost of polyglutamic acid as the Starting Substance can also toxicity by itself but is not found at all in the natural world. be mentioned. Nothing is known about their influence on the ecosystem 65 In addition, processes for obtaining a hydrogel by croSS resulting from an accumulation of Such polymers in Soil over linking an acidic amino acid were reported by Akamatsu et a long period and therefore, a thorough investigation is al. in U.S. Pat. No. 3,948,863 (corres.JP Kokoku 52-41309) 6,072,024 3 4 and Iwatsuki et al. in JP Kokai 5-279416. Further, use of the reaction system is thus solidified. This makes it difficult croSS-linked amino acid polymers as Superabsorbent poly to perform the reaction under Stirring, or post-reaction mers was reported by Sikes et al. in JPPCT Kokai 6-506244 treatments become extremely difficult. This production pro (corres. U.S. Pat. No. 5,247,068 and U.S. Pat. No. 5,284, ceSS is therefore not Suited for industrial production. The 936), Suzuki et al. in JP Kokai 7-309943 and Harada et al. production process of a croSS-linked polySuccinimide as a in JP Kokai 8-59820.
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