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United States Patent (19) 11 Patent Number: 4,656,211 Nasu Et Al

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United States Patent (19) 11 Patent Number: 4,656,211 Nasu Et Al United States Patent (19) 11 Patent Number: 4,656,211 Nasu et al. 45 Date of Patent: Apr. 7, 1987 54 CURABLE RESIN COMPOSITIONS AND FOREIGN PATENT DOCUMENTS THEIR USE 39797 11/1981 European Pat. Off. 75 Inventors: Kohji Nasu, Nishinomiya; Fumihiro 2068616 8/1971 France . Doura, Sakai, both of Japan 21040O8 4/1972 France . 1056079 1/1967 United Kingdom. 73) Assignee: Takeda Chemical Industries, Ltd., Osaka, Japan Primary Examiner-Maurice J. Welsh Attorney, Agent, or Firm-Wenderoth, Lind & Ponack (21) Appl. No.: 885,393 (57) ABSTRACT 22 Filed: Jul. 10, 1986 A curable resin composition which comprises (1) a copolymer composed of an aminoalkyl acrylate and/or Related U.S. Application Data aminoalkyl methacrylate and an ethylenically unsatu 63 Continuation of Ser. No. 783,627, Oct. 3, 1985, aban rated monomer and (2) a blocked polyisocyanate com doned. pound formulated therein. The curable resin composition undergoes curing at by (30) Foreign Application Priority Data far lowered temperatures as compared with the conven Oct. 5, 1984 JP Japan ................................ 59.2101.96 tionally employed baking paints consisting of hydroxyl Aug. 23, 1985 JP Japan ................................ 60-186141 containing resins and blocked polyisocyanate com pounds, and are therefore useful, for example, as a low 51) Int. Cl.".............................................. C08G 18/80 temperature baking type paint or adhesive. Heating 52 U.S. Cl. ................................. 524/198; 427/385.5; brings about the crosslinking through the reaction be 427/388.1; 427/388.2; 427/393.5; 525/188; tween isocyanate and amino groups, thus providing 525/330.5; 528/45 coating films with excellent flexibility, chemical resis 58) Field of Search ............. 524/198; 525/185, 330.5; tance, water resistance, impact resistance, corrosion 528/45; 427/385.5, 388.1, 388.2, 393.5 resistance, etc. The composition can be used to such substrates as metal, heat-resistant plastics and inorganic 56 References Cited materials, and can be applied onto electrical appliances U.S. PATENT DOCUMENTS for household uses, automobiles, building materials and 3,694,389 9/1972 Levy .............................. 260/23 TN the like. 3,716,599 2/1973 Vasta ................................... 260/859 4,444,955 4/1984 Mels et al. ........................... 525/124 8 Claims, No Drawings 4,656,211 1 2 CURABLE RESIN COMPOSITIONS AND THEIR R USE CH2FC This application is a continuation of now abandoned 5 COOR2NHR3 application Ser. No. 783,627, filed Oct. 3, 1985. This invention relates to polyurethane-based, curable wherein . resin compositions capable of forming coating films R is hydrogen or methyl group; with excellent low-temperature curing properties and R2 is an alkylene or a hydroxyalkylene group of 1 to 10 6 atoms; relates to their use. The resulting coating film excels in R is hydrogen or an alkyl group of 1 to 6 carbon flexibility, chemical resistance, water resistance, impact atons resistance and consequently, is of great use as a baking and an ethylenically unsaturated monomer. type paint and an adhesive for metal, heat-resistant Out of the copolymers, those composed from the plastics, inorganic materials, etc. 5 aminoalkyl acrylate and/or aminoalkyl methacrylate in Generally, resin compositions for paint uses consist which Rhu 2 is a hydroxyalkylene group of 1 to 6 car ing of a blocked polyisocyanate and a hydroxyl-group bon atoms are preferable in terms of excellent adhesive containing compound, such as polyester polyol, poly properties toward a substrate. ether polyols, acrylic polyols and epoxy resins, possess The aminoalkyl acrylate and/or aminoalkyl methac excellent corrosion resistance, chemical resistance, me 20 rylate includes, for example, acrylates, such as amino chanical properties, etc., and are therefore put in wide methyl acrylate, aminoethyl acrylate, aminopropyl ac use for such baking finishes as exterior painting of auto rylate, amino-n-butyl acrylate, aminohexyl acrylate, mobiles, cation electrodeposition, electrical appliances N-methylaminoethyl acrylate, N-tert-butylaminoethyl for household uses, precoat metal and enamelled wires. acrylate and aminohydroxypropyl acrylate, and meth The baking type coatings which are generally com 25 acrylates, such as aminomethyl methacrylate, amino ethyl methacrylate, amino-n-butyl methacrylate, N posed of a blocked polyisocyanate and a hydroxyl methylaminoethyl methacrylate, N-tert-butylamino group containing compound, nevertheless, require heat ethyl methacrylate and aminohydroxypropyl methacry ing at 140 to 200 C. for curing. Because of this, the cost late. The content of these aminoalkyl acrylates or ami of energy becomes increased, and the substrates to 30 noalkyl methacrylates in the copolymer is normally in which such coatings are applied are ordinarily limited the range of about 1 to 40 weight %, preferably in the to metal articles, whereby they are rarely utilized for range of about 5 to 30 weight %. substrates with greater specific heats, among others. On the other hand, the ethylenically unsaturated In the field of baking finishes for plastics articles, they monomer includes, for example, acrylates, such as are applied only to a limited extent on molded articles of 35 methyl acrylate, ethyl acrylate, n-butyl acrylate and thermosetting resins, such as phenol, urea, melamine, 2-ethylhexyl acrylate; methacrylates, such as methyl unsaturated polyester and epoxy resins, and the room methacrylate, ethyl methacrylate and n-butyl methacry temperature curing type coating systems, such as lac late; vinyl esters of fatty acids, such as vinyl acetate and quer type or two-packed type urethanes, are presently vinyl propionate; aliphatic monoolefins, such as ethyl employed for molded articles of PVC, ABS, polypro ene, propylene and isobutene; aromatic monoolefins, pylene, polyethylene, polycarbonate resins, etc. used in such as styrene and vinyltoluene; and other acryloni fields related with automobiles and electromagnetic trile, vinyl chloride and vinyl fluoride. One kind or not interference. less than two kinds of the above described monomers In view of the circumstances as described above, the 45 may be contained in the copolymer, and are contained present inventors carried out intensive research, and as in the copolymer normally at a ratio in the range of a result, found that the combination of (1) a copolymer about 60 to 99 weight %, preferably in the range of composed of an aminoalkyl acrylate and/or aminoalkyl about 70 to 95 weight %. The copolymer from an amino alkyl acrylate and/or methacrylate and an ethylenically unsaturated mono aminoalkyl methacrylate and an ethylenically unsatu mer with (2) a blocked polyisocyanate compound yields 50 rated monomer is advantageously produced for exam the coating films which undergo curing at an extremely ple by way of solution polymerization, whereby as the low temperature of not higher than 140 C. and also solvent to be used in such a polymerization reaction, exhibit excellent physical properties. These findings there are preferably employed such solvents as may be have led to the completion of this invention. 55 utilized as a solvent for the resin compositions in carry Thus, this invention is concerned with curable resin ing out this invention. Generally, the total monomer compositions which comprise (1) a copolymer com concentration is rendered about 20 to 80 weight %, posed of an aminoalkyl acrylate and/or aminoalkyl while as a polymerization initiator, there are used oil methacrylate and an ethylenically unsaturated mono soluble, free-radical producing catalysts, such as a,a'- mer and (2) a blocked polyisocyanate compound formu azobisisobutyronitrile, benzoyl peroxide, lauroyl perox lated therein, and is also concerned with a coating pro ide, t-butyl hydroperoxide and cumene hydroperoxide, cess which comprises applying the above curable resin and if necessary, it is possible to use redox catalysts composition to a substrate and heating at a temperature involving the combined use of reducing substances, as of not higher than 140 C. for curing. well. As a molecular weight modifier for the copoly The copolymer as mentioned above under (1) which 65 mer, furthermore, for example, butylmercaptan, dode is useful in this invention means copolymers composed cylmercaptan, t-dodecylmercaptain and 3-mercaptoe from an aminoalkyl acrylate and/or aminoalkyl methac thanol may be added in small amounts. The polymeriza rylate of the general formula: tion is carried out at atmospheric pressure and at a tem 4,656,211 3 4. perature in the neighborhood of 30°to 100° C. in an inert blocking agents based on phenol, lactam, active methy gas. lene, alcohol, mercaptan, acid amide, imide, amine, The copolymer thus obtained contains at least two imidazole, urea, carbamate, imine, oxime or sulfite com amino groups and exhibits a molecular weight in the pounds, and among others, blocking agents, based on range of about 1,000 to 1,000,000, preferably in the phenol, lactam, alcohol, imine, and oxime compounds range of about 5,000 to 500,000. The copolymer is used are advantageously used. as such, and may also be ketiminized with aliphatic The blocked polyisocyanate compound, when used in ketones and cyclic ketones, such as methyl ethyl ketone, combination with the copolymer (1) undergo curing at methyl isobutyl ketone and cyclohexanone. by far lowered temperature as compared with the con The polyisocyanate to be utilized for the blocked 10 ventionally employed baking paints regardless of the
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