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United States Patent (19) 11 Patent Number: 4992,507 Coogan Et Al

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United States Patent (19) 11 Patent Number: 4992,507 Coogan Et Al United States Patent (19) 11 Patent Number: 4992,507 Coogan et al. 45) Date of Patent: Feb. 12, 1991 (54) AQUEOUS DISPERSION OF ANONIONIC, 56) References Cited WATER-DESPERSIBLE POLYURETHANE U.S. PATENT DOCUMENTS 3,412,054 ll/1968 Milligan et al. ..................... 524/591 75 Inventors: Richard G. Coogan, North Reading: 3,479,310 1 1/1969 Dieterich et al. ..... ... 524/591 Razmik Vartan-Boghossian, Belmont; 3,756,992 9/1973 Dieterich ............................ 524/591 Milton Lapkin, Sudbury, all of Mass. 3,905,929 9/1975 Noll ........... ...... 524/839 3,920,598 11/1975 Reiff et al. .......................... 524/871 73) Assignee: ICI Americas, Inc., Wilmington, Del. 4,045,396 8/1977 Marans et al. ........................ 528/72 4,116,061 10/1986 Henning et al. .................... 524/59 4,258,222 3/1981 Mohring et al. .. ... 568/863 21 Appl. No.: 408,958 4,408,008 10/1983 Markusch .......... ... 524/591 4,569,981 2/1986 Wenzel et al. ... ... 528/67 (22 Filed: Sep. 18, 1989 4,622,360 l 1/1986 Gomi et al. ....... ... 524/507 4,670,100 6/1987 Henning et al. ...... 524/591 4,70,480 10/1987 Markusch et al. .................. 524/591 Related U.S. Application Data 4,764,553 8/1988 Mosbach et al. ................... 524/591 (63) Continuation of Ser. No. 244,394, Sep. 14, 1988, aban 4,857,565 8/1989 Henning et al. .................... 524/59 doned. Primary Examiner-Morton Foelak Assistant Examiner-Dennis R. Daley (30) Foreign Application Priority Data Attorney, Agent, or Firm-Cushman, Darby & Cushman Sep. 14, 1987 (GB) United Kingdom ................. 8721534 57 ABSTRACT Sep. 14, 1987 GB). United Kingdom ................. 8721535 An aqueous dispersion of a nonionic, water-dispersible polyurethane having pendent polyoxyethylene chains 51 Int. Cl.' ....................... C08L 75/00; C08L 75/04 and free acid or free tertiary amino groups. The disper 52 U.S. Cl. .................................... 524/591; 524/839; sions are useful as coating compositions. 524/589 58) Field of Search ........................ 524/591, 839, 589 15 Claims, No Drawings 4,992,507 1. 2 A free acid content may be introduced into the poly AQUEOUS DISPERSION OF ANONIONIC, urethane by including at an appropriate point in its WATER-DSPERSIBLE POLYURETHANE synthesis at least one component having at least one free acid group and at least two groups, for example hy This is a continuation of application Ser. No. 5 droxyl groups, which are more reactive than the acid 07/244,394, filed Sept. 14, 1988, which was abandoned groups towards isocyanate groups. In view of the essen upon the filing hereof. tially nonionic character of the polyurethane, the free This invention relates to aqueous dispersions and acid groups should not ionise to any substantial extent more particularly to aqueous dispersions of nonionic during storage or use of the dispersions. Particularly polyurethanes containing free acid or free tertiary 10 suitable acid groups are carboxylic acid groups. The amino groups and to the use of the dispersions as coat free acid group content of the polyurethane is suitably ing compositions. in the range from 5 to 185 milliequivalents per 100 g, Aqueous polyurethane dispersions are well known preferably from 10 to 100 milliequivalents per 100 g. and are used in the production of useful polyurethane A tertiary amino content may be introduced into the products, for example coatings and films. Dispersion of 15 polyurethane by including among the polyurethane the polyurethane in the aqueous system has been forming components at least one component having at achieved by the use of either external or internal dis least one tertiary amino group and at least two isocya persing or emulsifying agents but, in general, the inter nate-reactive groups. The free tertiary amino group nal agents, which can be ionic or nonionic, have been content of the polyurethane is suitably in the range from found to be more satisfactory. 20 8 to 180 milliequivalents per 100 g, preferably from 15 Water-dispersible polyurethanes of nonionic charac to 100 milliequivalents per 100 g. ter generally owe their dispersibility to the presence of The water-dispersible polyurethane may be linear or pendent polyoxyethylene chains along the main poly branched, branching being introduced by including urethane backbone. Thus, U.S. Pat. No. 3,905,929 de among the polyurethane-forming components at least scribes water-dispersible nonionic polyurethanes ob 25 one component having more than two isocyanate or tained by reacting an organic diisocyanate with an or isocyanate-reactive groups per molecule. The degree of ganic difunctional isocyanate-reactive compound and branching may be as high as one crosslink for each 3000 with an organic difunctional isocyanate-reactive com atomic weight units. pound containing side chain polyethylene oxide units. It will be appreciated by those skilled in the art that 30 polyurethane formulations frequently contain minor Aqueous dispersions containing the polyurethanes are proportions of reactants, such as water or diamines, used in the production of films and coatings. In the which introduce urea groups rather than urethane process of U.S. Pat. No 3,920,598, the polyethylene groups into the overall polyurethane structure. For the oxide chain is incorporated by being attached to a diisor purpose of calculating crosslink densities of the product cyanate molecule by means of an allophanate orbiuret 35 of the present invention, such reactants are regarded as linkage. polyurethane-forming components. German Offenlegungsschrift No. 2551094 describes A suitable free acid group containing water-dispersi water-dispersible polyurethanes which contain both ble polyurethane is the reaction product of: ionic and nonionic hydrophilic groups, the ionic centres (A) a nonionic, water-dispersible, isocyanate-ter being quaternary ammonium, carboxylate or sulphonate 40 minated polyurethane prepolymer formed by react ions which are associated with appropriate salt-forming ling: counter-ions. (i) an organic polyisocyanate; It has now been found that aqueous dispersions of (ii) at least one organic polyol having a molecular nonionic, water-dispersible polyurethanes containing weight in the range 62 to 6000; free acid or free tertiary amino groups, that is to say 45 (iii) a dispersing diol and/or diisocyanate having a unneutralised acid or tertiary amino groups, have excel pendent polyoxyethylene chain, and lent storage stability and can be used in the preparation (iv) an isocyanate-reactive compound containing at of linear or crosslinked polyurethanes of various types. least one carboxylic acid group and at least two Accordingly, the invention provides an aqueous dis groups which are more reactive than carboxylic persion of a nonionic, water-dispersible polyurethane acid groups towards isocyanate groups; and having pendent polyoxyethylene chains and free acid or (B)an active hydrogen containing chain extender, free tertiary amino groups. A suitable free tertiary amino group containing wa For the purpose of the invention, an "aqueous disper ter-dispersible polyurethane is the reaction product of: sion' means a dispersion of the polyurethane in an aque (A) a nonionic, water-dispersible, isocyanate-ter ous medium of which water is the principal ingredient. 55 minated polyurethane prepolymer formed by react Minor amounts of organic solvents may optionally be 1ng: present. (i) an organic polyisocyanate; The pendent polyoxyethylene chain content of the (ii) at least one organic polyol having a molecular water-dispersible polyurethane may vary within wide weight in the range 62 to 6000, and limits but in all cases should be sufficient to provide the (iii) a dispersing diol and/or diisocyanate having a polyurethane with the required degree of water dispers pendent polyoxyethylene chain; and ibility. The polyoxyethylene side chains may be intro (B) an active hydrogen containing chain extender, duced into the polyurethane by methods described in wherein at least one polyol and/or chain extender the prior art. Thus, the polyurethane-forming ingredi contains a free tertiary amino group. ents may include one or more components having pen 65 The polyisocyanate used in making the prepolymer dent polyoxyethylene chains, for example a diol and/or may be an aliphatic, cycloaliphatic, araliphatic or aro diisocyanate having a poly(ethylene oxide) side chain as matic polyisocyanate. Examples of suitable polyisocya described in U.S. Pat. Nos. 3,905,929 or 3,920,598. nates include ethylene diisocyanate, 1,6-hexamethylene 4,992,507 3 4. diisocyanate, isophorone diisocyanate, cyclohexane glycol, neopentyl glycol, i,4-butanediol, furan dine 1,4-diisocyanate, 4,4'-dicyclohexylmethane diisocya thanol, cyclohexane dimethanol, glycerol, trimethylol nate, p-xylylene diisocyanate, 1.4-phenylene diisocya propane or pentaerythritol or mixtures thereof with nate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, polycarboxylic acids, especially dicarboxylic acids or 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylme their ester-forming derivatives, for example succinic, thane diisocyanate, polymethylene polyphenyl polyiso glutaric and adipic acids or their dimethyl esters, cyanates and 1,5-naphthylene diisocyanate. Mixtures of phthalic anhydride or dimethyl terephthalate. Polyes polyisocyanates can be used and also polyisocyanates ters obtained by the polymerisation of lactones, for which have been modified by the introduction of ure example caprolactone, in conjunction with a polyol thane, allophanate, urea, biuret, carbodiimide,
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