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(12) United States Patent (10) Patent No.: US 6,559,231 B2 Hasegawa Et Al

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(12) United States Patent (10) Patent No.: US 6,559,231 B2 Hasegawa Et Al USOO6559231B2 (12) United States Patent (10) Patent No.: US 6,559,231 B2 Hasegawa et al. (45) Date of Patent: May 6, 2003 (54) CURING TYPE WATER BASE RESIN 5,614,582 A 3/1997 Hori et al. .................. 524/507 COMPOSITION FOREIGN PATENT DOCUMENTS (75) Inventors: Mitsutaka Hasegawa, Nagoya (JP); JP 52-22878 6/1977 Hiroshi Inukai, Nagoya (JP); Eiichi JP 56-28208 3/1981 Okazaki, Haguri-gun (JP); Nobushige JP 56-53119 5/1981 Numa, Ebina (JP); Masami Sugishima, JP 56-296.57 7/1981 Hiratsuka (JP); Koki Nakamura, JP 56-127697 10/1981 Chigasaki (JP); Keiichiro Saikawa, JP 62-1005O2 5/1987 O O JP 1-242569 9/1989 Hiratsuka (JP); Yushichi Ishihara, JP 4-538O2 2/1992 Yokohama (JP) JP 4-249587 9/1992 O TY O JP 5-339.542 12/1993 (73) ASSignee: Kansai Paint Co., Ltd., Hyogo-ken JP 8-151358 6/1996 (JP) JP 8-245878 9/1996 JP 8-283377 10/1996 (*) Notice: Subject to any disclaimer, the term of this JP 10-259356 9/1998 patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. * cited by examiner Primary Examiner-David W. Wu (21) Appl. No.: 09/996,917 Assistant Examiner Satya Sastri (74) Attorney, Agent, or Firm Wenderoth, Lind & Ponack, (22) Filed: Nov.30, 2001 LLP. (65) Prior Publication Data (57) ABSTRACT US 2002/0128379 A1 Sep. 12, 2002 The present invention relates to a curing type water base (30) Foreign Application Priority Data resin composition comprising: (I) a copolymer obtained by copolymerizing an ethylenically Nov. 30, 2000 (JP) ....................................... 2000-364667 unsaturated monomer (a) having a maleimide group, an Sep. 4, 2001 (JP) ...... ... 2001-266931 Sep. 4, 2001 (JP) ...... ... 2001-266939 ethylenically unsaturated monomer (b) having a carbonyl Sep. 26, 2001 (JP) ....................................... 2001-29.3582 group and other ethylenically unsaturated monomer (c) and (51) Int. Cl." ................................................ C08L 39/04 (II) a compound having two or more groups per molecule (52) U.S. Cl. ....................... 525/203; 525/203; 525/282; which are the same or different and selected from a 525/161; 525/448; 524/555 hydrazide group, a Semicarbazide group and hydrazone (58) Field of Search ................................. 525/203,282, group and further comprising, if necessary, as an addi 525/161, 148; 524/555 tional component: (III) a copolymer having a carbonyl group and/or (56) References Cited (IV) a water base polyurethane resin having a carbonyl U.S. PATENT DOCUMENTS group or a hydrazine group. 3.689,448 A 9/1972 Berger et al. 41 Claims, No Drawings US 6,559,231 B2 1 2 CURING TYPE WATER BASE RESN Also, the present invention provides the curing type water COMPOSITION base resin composition described above further comprising as an additional component: The present invention relates to a curing type water base (III) a copolymer having a carbonyl group and/or resin composition, more specifically to a curing type water 5 base resin composition of a Single liquid type which is (IV) a water base polyurethane resin having a carbonyl excellent in low temperature physical properties and which group or a hydrazine group. can readily be cured regardless of coating environment. The curing type water base resin composition of the In recent years, Switching from an organic Solvent type present invention shall be explained below in further details. over to a water base type has been being expedited in the In the present specification, an acryloyl group or a meth fields of coating materials, inks and adhesives from the acryloyl group is expressed as a (meth)acryloyl group; Viewpoints of resource Saving, environmental Sanitation, non-public pollution and non-hazardousness. For example, acrylate or methacrylate is expressed as (meth)acrylate; in water base coating materials in the construction field, acrylic acid or methacrylic acid is expressed as (meth) required are coating materials which are dried at a room acrylic acid; acrolein or methacrolein is expressed as (meth) temperature and excellent in coating film performances Such 15 acrolein; acrylamide or meth acrylamide is expressed as as a water resistance, a weatherability and a stain resistance, (meth)acrylamide; and an allyl group or a methallyl group is and emulsion particles having a croSS-linkable carbonyl expressed as a (meth)allyl group. group and acryl base resin compositions comprising a dihy Copolymer (I) drazide compound are disclosed in, for example, Japanese Patent Application Laid-Open No. 249587/1992 as a resin The copolymer (I) is a copolymer which is obtained by composition for a water base cold-dryable coating material copolymerizing the ethylenically unsaturated monomer (a) which Satisfies Such requirement and is Suited to construc having a maleimide groups the ethylenically unsaturated tion use. monomer (b) having a carbonyl group and the other ethyl Further, resin compositions prepared by further blending enically unsaturated monomers (c) and which has a male the above acryl base resin compositions with water base 25 imide group and a carbonyl group in a molecule. polyurethane resins are proposed in Japanese Patent Appli The ethylenically unsaturated monomer (a) having a cation Laid-Open No. 339542/1993, U.S. Pat. No. 5,614,582 maleimide group is used in order to introduce into the (=EP-A-648,794) and Japanese Patent Application Laid copolymer (I), a maleimide group for three-dimensionally Open No. 259356/1998 for the purpose to provide the above croSS-linking a coating film formed from the resin compo acryl base resin compositions with a toughness, a coating Sition of the present invention by optical dimerization by film elasticity and low temperature physical properties. The irradiating with natural light. above compositions are excellent in a Storing property and improve in coating film physical properties by using a Water Included in Such ethylenically unsaturated monomer (a) base polyurethane resin in combination, but a croSS-linking having a maleimide group is a compound hereinafter reaction does not Sufficiently proceed depending on coating 35 referred to merely as an (imide compound) having an environment in a certain case. There is, for example, the ethylenically unsaturated group and a cyclic imide group problem that the water resistance at an initial Stage after represented by the following Formula (1): coating (initial water resistance) is unsatisfactory in coating (1) in the environment in which evaporation of moisture is O notably slow as observed when the ambient temperature is 40 R low. Intensive investigations repeated by the present inventors N in order to solve the problem described above involved in conventional water base cold-dryable Single liquid type R2 coating compositions have resulted in finding that a curing 45 O type water base resin composition capable of forming a coating film which is excellent in a water resistance and a curing property even at an initial Stage after coating regard wherein R' and Reach represent independently a hydrogen less of coating environment can be obtained by introducing atom or an alkyl group, or R' and R represent a group a maleimide group cured by irradiation with natural light 50 forming a carbon ring together with carbon atoms to which into a copolymer having a croSS-linkable carbonyl group, they are bonded. using a hydrazine compound as a cross-linking agent in The ethylenically unsaturated group in the imide com combination and using Supplementarily photocuring caused pound described above includes, for example, a vinyl group, by a maleimide group in combination with a croSS-linking an allyl group and a (meth)acryloyl group, and the (meth) reaction caused by a carbonyl group/cross-linking agent, and 55 acryloyl group is particularly preferred. they have come to complete the present invention. From the Viewpoints of the polymerizing property Thus, the present invention provides a curing type water between the imide compounds and the copolymerizing prop base resin composition comprising: erty with other unsaturated monomers, R' and R in the (I) a copolymer obtained by copolymerizing an ethylenically Formula (1) described above each are independently alkyl unsaturated monomer (a) having a maleimide group, an 60 ethylenically unsaturated monomer (b) having a carbonyl groups, preferably alkyl groups having 4 or leSS Gcarbon group and other ethylenically unsaturated monomer (c) atoms, or groups forming a carbon ring together, for and example -CHCHCH- and -CHCHCHCH-, (II) a compound having two or more groups per molecule preferably -CH2CHCHCH-. which are the same or different and selected from a 65 To be specific, the imide compound includes, for example, hydrazide group, a Semicarbazide group and hydraZone imide (meth)acrylate represented by the following Formula grOup. (2): US 6,559,231 B2 4 having a maleimide group and the ethylenically unsaturated (2) monomer (b) having a carbonyl group each described above includes, for example, alkyl (meth)acrylates Such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth) acrylate, lauryl(meth) acrylate and Stearyl (meth)acrylate; cyclic (meth)acrylates Such as cyclohexyl (meth)acrylate and isobornyl (meth)acrylate, aralkyl (meth)acrylates Such as benzyl (meth)acrylate; alkoxyalkyl (meth)acrylates Such wherein R' and R are synonymous with those described as 2-methoxyethyl (meth)acrylate and 2-ethoxyethyl (meth) above; R represents an alkylene group, preferably an alky acrylate;
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