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(19) United States (12) Patent Application Publication (10) Pub US 20120238701A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0238701 A1 Yamada et al. (43) Pub. Date: Sep. 20, 2012 (54) AQUEOUS POLYURETHANE RESIN Publication Classi?cation DISPERSION, PROCESS FOR PREPARING (51) Int Cl THE SAME AND USE THEREOF C09 D 175/06 (200601) (52) US. Cl. ...................................................... .. 524/839 (76) Inventors: Takeshi Yamada, Ube-shi (JP); (57) ABSTRACT Masahiro Naiki, Ube-shi (JP) An object is to obtain an aqueous polyurethane resin disper (21) Appl. No.: 13/508,934 sion Which provides a coating ?lm having high hardness, oleic acid resistance and solvent resistance. (22) PCT Filed: Nov. 8, 2010 The aqueous polyurethane resin dispersion comprises a poly urethane resin obtained by reacting (a) a polyol compound, (b) a polyisocyanate compound, (0) an acidic group-contain (86) PCT No.: PCT/JP2010/069789 ing polyol compound and (d) a chain-elongating agent being dispersed in an aqueous medium, Wherein (a) the polyol § 371 (0X1)’ compound comprises a polycarbonate polyol compound rep (2), (4) Date: May 9, 2012 resented by the formula (1), a hydroxyl equivalent of (a) the polyol compound and (c) the acidic group-containing polyol (30) Foreign Application Priority Data compound is 180 to 400, and a total acid value of (a) the polyol compound, (b) the polyisocyanate compound and (c) Nov. 10, 2009 (JP) ............................... .. 2009-257115 the acidic group-containing polyol compound is 22 to 40 mg Aug. 6, 2010 (JP) ............................... .. 2010-177086 KOH/ g. US 2012/0238701A1 Sep. 20, 2012 AQUEOUS POLYURETHANE RESIN [0008] An object of the present invention is to obtain an DISPERSION, PROCESS FOR PREPARING aqueous polyurethane resin dispersion Which gives a coating THE SAME AND USE THEREOF ?lm or surface having high strength, as Well as excellent oleic acid resistance and solvent resistance. TECHNICAL FIELD Means to Solve the Problems [0001] The present invention relates to an aqueous polyure thane resin dispersion, a process for preparing the same and [0009] The present inventors have earnestly studied to use thereof. solve the above-mentioned problems, and as a result, they have found out that by using a polycarbonate polyol com BACKGROUND ART pound having a speci?c alicyclic structure as a starting polyol, an aqueous polyurethane resin dispersion Which provides a [0002] An aqueous polyurethane resin dispersion has been coating ?lm having high hardness as Well as excellent oleic Widely utilized as a starting material for a paint or a coating acidresistance and solvent resistance, Whereby accomplished agent, for example, a starting material for a paint or a coating the present invention. agent for coating an outside and inside of an aircraft, auto [0010] That is, the present invention has the folloWing con mobile, etc., an external Wall surface, a ?oor material and stitutions. furniture of house, and synthetic leather to be used for clothes [0011] The present invention 1 is an aqueous polyurethane or a surface skin of sofa, etc. In addition, it has been also resin dispersion comprising a polyurethane resin obtained by utiliZed as an adhesive by mixing With a rubber, etc. In the reacting (a) a polyol compound, (b) a polyisocyanate com above-mentioned uses, a coating ?lm obtained by the aque ous polyurethane resin dispersion has a role of not only pound, (c) an acidic group-containing polyol compound and appealing beauty of appearance, but also protecting the base (d) a chain-elongating agent being dispersed in an aqueous medium, Wherein (a) the polyol compound contains a poly material, so that it is required to have strength and durability. carbonate polyol compound represented by the formula (1): For these purposes, it has been earnestly desired to provide an aqueous polyurethane resin dispersion Which gives a coating [Formula I] ?lm having higher strength and higher durability. (1) [0003] To satisfy the above-mentioned properties, aqueous polyurethane resin dispersions using various kinds of poly mer polyols have been developed. More speci?cally, as poly mer polyols, a polyester polyol, polyether polyol, polycar bonate polyol, etc., have been used for the preparation of aqueous polyurethane resin dispersions. Among these, the polycarbonate polyol has a characteristic that provides a (Wherein tough coating ?lm as compared With those of the polyester [0012] R1 and R2 each independently represent a direct polyol or polyether polyol. Above all, it has been knoWn that bond or an aliphatic hydrocarbon group having 1 to 10 carbon an aqueous polyurethane resin dispersion prepared by using a atoms Which may have a substituent(s), polycarbonate diol having an alicyclic structure provides a [0013] n is 0 or 1, coating ?lm excellent in Weather resistance and moist-heat [0014] m is a number Which makes a number average resistance (Patent Literature 1). molecular Weight of the formula (1) 400 to 2000), [0004] Also, it has been reported that an aqueous polyure a hydroxyl equivalent of (a) the polyol compound and (c) the thane resin dispersion produced by using a polycarbonate diol acidic group-containing polyol compound being 180 to 400, comprising l,4-butane diol Which is a diol having 4 or less and carbon atoms as a constitutional unit provides a coating ?lm a total acid value of (a) the polyol compound, (b) the poly excellent in oil resistance (Patent Literature 2). isocyanate compound and (c) the acidic group-containing [0005] [Patent Literature 1] JP H06-248046A polyol compound being 22 to 40 mg KOH/g. [0006] [Patent Literature 2] JP 2008-303285A [0015] The present invention 2 relates to the above-men tioned aqueous polyurethane resin dispersion Wherein a con DISCLOSURE OF THE INVENTION tent of an alicyclic structure in (a) the polyol compound is 35 to 65% by Weight. Problems to be Solved by the Invention [0016] The present invention 3 relates to the above-men [0007] HoWever, the diol constituting the polycarbonate tioned aqueous polyurethane resin dispersion Wherein (a) the diol in Patent Literature 1 comprises a mixture of tWo com polyol compound is a polycarbonate polyol compound rep ponents of l,4-cyclohexane dimethanol and 1,6-hexane diol, resented by the formula (1'): or a diol mixture in Which other diol(s) is/ are used in addition [Formula 2] to the above-mentioned tWo components. Therefore, Whereas Formula (I ') the coating ?lm obtained by the aqueous polyurethane resin dispersion has su?icient hardness, there are problems that O durability or dimensional stability against sebum contained in sWeat (oleic acid resistance), and solvent resistance are not suf?cient. On the other hand, the coating ?lm obtained by the aqueous polyurethane resin dispersion using a polycarbonate H O m O\H diol Which comprises l,4-butane diol as a constitutional unit as shoWn in Patent Literature 2 involves the problems that it is (Wherein m is a number Which makes the number average ?exible Whereby its hardness is insuf?cient. molecular Weight of the formula (1') 400 to 2000). US 2012/0238701A1 Sep. 20, 2012 [0017] The present invention 4 relates to the above-men [0027] (a) The polyol compound comprises a polycarbon tioned aqueous polyurethane resin dispersion Wherein the ate polyol compound represented by the formula (1): dispersion comprises a polyurethane resin Which is obtained by reacting a prepolymer obtained by reacting (a) the polyol compound, (b) the polyisocyanate compound and (c) the [Formula 3] acidic group-containing polyol compound, and (d) the chain Formula (I) elongating agent being dispersed in an aqueous medium. [0018] The present invention 5 relates to the above-men tioned aqueous polyurethane resin dispersion Wherein the prepolymer is in the form of a prepolymer solution With 14000 cP or loWer at 80° C. [0019] The present invention 6 relates to the above-men tioned aqueous polyurethane resin dispersion Wherein a molar ratio of the hydroxyl group derived from (a) the polyol compound and (c) the acidic group-containing polyol com (Wherein pound and the isocyanate group derived from (b) the polyiso [0028] R1 and R2 each independently represent a direct cyanate compound is 1:1.51 to 112.5. bond or an aliphatic hydrocarbon group having 1 to 10 carbon [0020] The present invention 7 relates to a paint composi atoms Which may have a substituent(s), tion comprising the above-mentioned aqueous polyurethane [0029] n is 0 or 1, and resin dispersion. [0030] m is a number Which makes a number average [0021] The present invention 8 relates to a coating agent molecular Weight of the formula (1) 400 to 2000). In (a) the composition comprising the above-mentioned aqueous poly polyol compound, the polycarbonate polyol compound rep urethane resin dispersion. resented by the formula (I) is preferably 50% by Weight or [0022] The present invention 9 relates to a composition for more, and more preferably 75% by Weight or more. In the a synthetic leather comprising the above-mentioned aqueous formula (1), the case where R1 and R2 are direct bonds means polyurethane resin dispersion. the carbon atom and the oxygen atom in the alicyclic structure [0023] The present invention 10 relates to a synthetic are directly bonded. leather comprising a ?ber base material treated by the above [0031] The aliphatic hydrocarbon group having 1 to 10 mentioned composition for a synthetic leather. carbon atoms of R1 and R2 in the formula (1) may be men [0024] Further, the present invention 1 1 relates to a process tioned, for example, a straight or branched C 1 to C10 alkylene for preparing the above-mentioned aqueous polyurethane group. The aliphatic hydrocarbon group having 1 to 10 carbon resin dispersion Which comprises the steps of atoms may have a substituent(s), and the substituent(s) may be mentioned a substituent(s) Which does/do not react With (l) a step of preparing a prepolymer by reacting (a) the polyol the isocyanate group.
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