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United States Patent (19) 11 Patent Number: 4,981,889 Baba Et Al

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United States Patent (19) 11 Patent Number: 4,981,889 Baba Et Al United States Patent (19) 11 Patent Number: 4,981,889 Baba et al. 45 Date of Patent: Jan. 1, 1991 54 PLASTISOL COMPOSITION (56) References Cited U.S. PATENT DOCUMENTS 75 Inventors: Akira Baba, Ibaraki; Takashi Maebashi; Takashi Nakayama, both 3,423,354 1/1969 Jones ................................... 524/145 3,644,229 2/1972. Butler et al. ... 525/29 of Takatsuki, all of Japan 3,917,550 1 1/1975 Clas et al. ....... ... 524/297 73 Assignee: Sunstar Gilken Kabushiki Kaisha, 4,623,686 11/1986 Hurnik et al. ....................... 524/659 Osaka, Japan Primary Examiner-Veronica P. Hoke Attorney, Agent, or Firm-Wegner, Cantor, Mueller & 21 Appl. No.: 341,704 Player 22 Filed: Apr. 21, 1989 57 ABSTRACT A plastisol composition which comprises a polyvinyl 30 Foreign Application Priority Data chloride, a plasticizer and a blocked isocyanate com pound as an adhesion-modifier, supplemented with a Apr. 26, 1988 JP Japan ................................ 63-107099 powdery curing agent for an epoxy resin having a melt 51) Int. Cl.......................... C08K 5/12; C08K 5/521 ing point of 50 to 150 C. which is surface-treated. The 52 U.S. C. .................................... 524/109; 524/143; plastisol composition of the present invention has an 524/145; 524/297; 524/314; 525/111; 525/121 improved adhesion property at a lower temperature and 58 Field of Search ............... 525/124, 127, 129, 111, is useful as an adhesive, sealing agent and coating agent, 525/121; 524/569, 109, 112, 114, 206, 257, 296, 297,143, 145, 314, 196 8 Claims, No Drawings 4,981,889 1. 2 chloride (e.g. vinylidene chloride, vinyl bromide, etc.), PLASTSOL COMPOSTION and the like. The plasticizer used in the present invention may be The present invention relates to a plastisol composi those commonly used for polyvinyl chloride and in tion, more particularly, a plastisol composition compris cludes, but not limited to, phthalic acid di(C4-C10)alkyl ing polyvinyl chloride as a main component, a plasti or (CA-C10)alkyl-(C6-C8)aryl esters such as di(n-butyl) cizer, a blocked isocyanate compound as an adhesion phthalate, octyldecyl phthalate, diisodecyl phthalate, modifier and a powdery curing agent having a melting di(2-ethylhexyl) isophthalate, di(2-ethylhexyl) phthal point of 50' to 150' C. which is surface-treated, said ate, butylbenzyl phthalate, dioctyl phthalate (DOP), composition having an improved adhesion properties 10 dinonyl phthalate, diisononyl phthalate (DINP), dihep when gelated under low temperature conditions such as tyl phthalate and butyl phthalyl butyl glycolate; ali at 110' to 130' C. for 15 to 30 minutes. phatic dibasic acid esters such as dioctyl adipate, dide cyl adipate, dioctyl sebacate, di(2-ethylhexyl) adipate, TECHNICAL BACKGROUND AND PRIOR ART diisodecyl adipate, di(2-ethylhexyl) azelate, dibutyl seb A plastisol composition comprising polyvinyl chlo 15 acate and di(2-ethylhexyl) sebacate; phosphoric acid ride as a main component has been employed as adhe esters such as tricresyl phosphate, trioctyl phosphate, sives, sealant or coating material in various fields. As tributyl phosphate, tri-2-ethylhexyl phosphate and 2 such a type of plastisol composition, for example, there ethylhexyldiphenyl phosphate; epoxy type plasticizers is known a composition which comprises a polyvinyl such as epoxydized soybean oil and 2-ethylhexyl epoxy chloride, a plasticizer and a blocked compound of diiso 20 dized tall oil fatty acid ester, and other polyester type cyanate polymer with a long-chain alkylated phenol as plasticizers, which are used alone or in combination of an adhesion-modifier (cf. Japanese Patent First Publica at least two thereof. Such plasticizer has an influence on tion No. 41278/1987). This plastisol composition, how viscosity of the plastisol and properties of the gellated ever, has been found to have less adhesion properties product, and may usually be used in an amount of under low temperature conditions such as 110 to 130 25 65-130 parts (parts by weight, hereinafter the same) per C., though it has an excellent storage stability under 100 parts of polyvinyl chloride. conditions of high temperature and high humidity with The blocked isocyanate compound used in the pres out foaming and discoloration and is capable of forming ent invention as an adhesion-modifier is prepared by a gelated compound with an excellent adhesion strength blocking a diisocyanate polymer with a conventional under high temperature conditions. 30 procedure. SUMMARY OF THE INVENTION The above diisocyanate polymer can be prepared by a conventional method, that is, by polymerizing a diiso The present inventors have intensively studied to cyanate monomer such as an aliphatic diisocyante (e.g. improve adhesion properties of the plastisol composi hexamethylene diisocyanate, lysine diisocyanate), an tion under low temperature conditions, and as a result, 35 alicyclic diisocyanate (e.g. hydrogenated diphenyl it was found that the adhesion properties under low methane diisocyanate, isophorone diisocyanate, hydro temperature conditions can remarkably be improved by genated tolylene diisocyanate) and an aromatic diisocy adding a specific curing agent for an epoxy resin to the anate (e.g. tolylene diisocyanate, diphenylmethane di above plastisol composition. isocyanate, naphthylene diisocyanate, xylene diisocya That is, the present invention provides a plastisol nate) in an inert solvent (e.g. ethyl acetate, methyl ace composition which comprises a polyvinyl chloride, a tate, butyl acetate, chlorobenzene) or in a plasticizer plasticizer and a blocked isocyanate compound as an (phthalic acid esters, phosphoric acid esters, adipic acid adhesion-modifier, supplemented with a powder curing esters, trimelitic acid esters). The diisocyanate polymer agent for an epoxy resin having a melting point of 50' to may also be an isocyanate-terminated urethane prepoly 150' C. which is surface-treated. 45 mer which is prepared by reacting a polyalkylene ether DETAILED DESCRIPTION OF THE polyol with an excess amount of the above diisocyanate INVENTION OOer. The polyvinyl chloride used in the present invention A blocking agent used for blocking the above diiso may be those commonly used for plastisol, including 50 cyanate polymer includes (C2-C4) alcohols such as those prepared by polymerizing vinyl chloride alone or ethanol, propanol, butanol and isobutanol; phenols such together with other copolymerizable monomer by as phenol, cresol, xylenol and p-nitrophenol; long emulsion polymerization, suspension polymerization, chained (C4-C10)-alkylphenols such as butylphenol, bulk polymerization, solution polymerization and the hexylphenol, octylphenol and nonylphenol; activated like. Such copolymerizable monomer includes, for ex 55 methylene compounds such as ethyl malonate, ethyl ample, vinyl esters of (C2-C10)alkanoic acids (e.g. vinyl acetoacetate and acetylacetone; (C2-C4)-alkanoic or acetate, vinyl propionate, vinyl laurate, etc.), acrylic alkenoic acid amides such as acetamide, acrylamide and acid (C1-C4)alkyl esters (e.g. methyl acrylate, ethyl acetanilide; (C2-C6)dibasic alkanoic acid imides such as acrylate, butyl acrylate, etc.), methacrylic acid (C1-C- succinimide and maleinimide; mono- or di-(C1-C4)- 4)alkyl esters (e.g. methyl methacrylate, ethyl methac alkyl-substituted imidazoles such as 2-ethylimidazole rylate, etc.), maleic acid di(C1-C4)alkyl esters (e.g. di and 2-ethyl-4-methylimidazole; lactams such as 2-pyr butyl maleate, diethyl maleate, etc.), fumaric acid di(C- rolidone and e-caprolactam; oximes of ketone or alde 1-C4)alkyl esters (e.g. dibutyl fumarate, diethyl fumar hyde such as acetoxime, methyl ethyl ketoxime, cyclo ate, etc.), vinyl (C1-C10)-alkyl ethers (e.g. vinyl methyl hexanone oxime and acetaldoxime; ethyleneimine, bisul ether, vinyl butyl ether, vinyl octyl ether, etc.), vinyl 65 fates and the like, preferably long-chained (CA-C10)al cyanates (e.g. acrylonitrile, methacrylonitrile, etc.), kylphenols, lactams and oximes, in view point of stor a-olefins (e.g. ethylene, propylene, styrene, etc.), vinyl age stability and curing characteristics, and most prefer halogenides or vinylidene halogenides other than vinyl ably butylphenol, hexylphenol, octylphenol, nonylphe 4,981889 3 4. nol, e-caprolactam, methyl ethyl ketoxime and cyclo Group B compounds): dibasic (C2-C10) carboxylic hexanone oxime. acids such as succinic acid, adipic acid, sebacic acid, These blocking agents are reacted with the diisocya phthalic acid, terephthalic acid and dimer acid; nate polymer to prepare a blocked isocyanate com (C1-C4)-alkane- or (C6-C8)aryl-sulfonic acids such as pound. In this reaction, about 0.90-1.5 equivalents, pref ethanesulfonic acid and p-toluenesulfonic acid; isocya erably about 1.0-1.3 equivalents of the blocking agent is nates such as tolylene diisocyanate, 4,4'-diphenyl diiso employed per 1 mol of the isocyanate group. When the cyanate and hexamethylene diisocyanate; p-hydroxys blocking agent is used in an amount less than 0.9 tyrene resin; phenol resin; epoxy resin; and the like. equivalents, resulting blocked isocyanate compound Amoung the above powdery curing agents having a may contain free isocyante groups to have a bad 10 melting point of 50 to 150' C., preferable are those influence on the storage stability, and on the other containing at least two active hydrogens of amino hand, when the amount of the blocking agent exceeds group in a molecule for example, the above aromatic 1.5 equivalents, the unreacted blocking agent may amines; addition product of aliphatic
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