1,6-diisocyanatohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In order to prepare the test coating, 100 grams of the above oligomer were mixed with 0.1 gram of T-12 tin catalyst, and 20 grams of EEP solvent. A second component was prepared from 126.4 grams of isocyanate multifunctional oligomer biurets formed by the reaction product between hexamethylene diisocyanate and water and 20 g of EEP solvent. Three mil wet films were cast from the mixed components which dried hard in two hours and had a Sward hardness of 10 in 24 hours.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same isocyanuration reaction as in Example 1 was carried out except that 3,290 g of hexamethylene diisocyanate and 210 g of "Takenate 500" (xylylene diisocyanate produced by Takeda Chemical Industry Co., Ltd.) were used instead of 3,500 g of hexamethylene diisocyanate, and the amount of the isocyanuration catalyst used in Example 1 was changed to 4.7 g. There was obtained 4,219 g of the reaction mixture containing the deactivated catalyst. The same isocyanuration reaction as in Example 1

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-liter 3-necked flask provided with a stirrer and thermometer were metered in 365.4 parts of 2-hydroxyethyl acrylate, 0.45 parts of di-n-butyltin dilaurate, and 0.4 parts of hydroquinone monomethylether, followed by stirring at 55° C. and adding dropwise in 3 hours, 543.1 parts of a triisocyanate (tradename: Duranate TPA-100, manufactured by Asahi Kasei Kogyo Co., Ltd.), a trimer of hexamethylene diisocyanate and having an isocyanurate skeleton. After the end of the dropwise addition, the reaction was further continued for 8 hours at 70° C. when the viscosity increased so that n-butyl acetate was used to dilute to give a urethane triacrylate (UPA-3) having a final solids concentration of 90% by weight. A 2-liter 3-necked flask provided with a stirrer adding dropwise in 3 hours After the end of the dropwise addition to dilute

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-tolylene diisocyanate; p-phenylene diisocyanate; diphenylmethane diisocyanate (may be abbreviated as "MDI"); m-phenylene diisocyanate; hexamethylene diisocyanate; tetramethylene diisocyanate; 3,3'-dimethoxy-4,4'-biphenylene diisocyanate; 2,4-naphthalene diisocyanate; 3,3'-dimethyl-4,4'-biphenylene diisocyanate; 4,4'-diphenylene diisocyanate; 4,4'-diisocyanato diphenyl ether; 1,5-naphthalene diisocyanate; p-xylylene diisocyanate; m-xylylene diisocyanate; 1,3-diisocyanato methylcyclohexane; 1,4-diisocyanato methylcyclohexane; 4,4'-diisocyanato dicyclohexane; 4,4'-diisocyanato dicyclohexylmethane; and isophorone diisocyanate.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 288 g of HMDI was added 20 g of cyclohexylamine and they were stirred at 100° C. for one hour while nitrogen was bubbled thereinto and subsequently 2.9 g of the carbodiimidization catalyst was added thereto, after which the resulting mixture was subjected to a reaction at 185° C. for 30 hours, to obtain a carbodiimide resulting from HMDI and having terminal urea bonds (degree of polymerization=10). was bubbled subsequently 2.9 g of the carbodiimidization catalyst was added after which the resulting mixture was subjected to a reaction at 185° C. for 30 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 236 g of HMDI with 25.0 g of cyclohexyl isocyanate (referred to hereinafter as CHI) was added 2.60 g of the carbodiimidization catalyst, and they were subjected to a reaction at 185° C. for 19 hours while nitrogen was bubbled thereinto, to obtain a carbodiimide resulting from HMDI and CHI (degree of polymerization=10). were subjected to a reaction at 185° C. for 19 hours while nitrogen was bubbled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Examples of suitable monomers of the polyisocyanates include, but are not limited to, 1,4-diisocyanatobutane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 4,4'-diisocyanato-dicyclohexylmethane, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and/or 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl cyclohexane (isophorone or IPDI), 2,4-and/or 2,6-hexahydrotoluylene diisocyanate, hexahydro-1,3- and/or 1,4-phenylene diisocyanate, perhydro-2,4'-and/or -4,4'diphenylmethane diisocyanate, 1,3-and/or 1,4-phenylene diisocyanate, 2,4- and/or 2,6-toluylene diisocyanate, diphenyl methane-2,4'-and/or -4,4'-diisocyanate, naphthalene-1,5-diisocyanate, triphenyl methane-4,4',4"-triisocyanate and polyphenyl polymethylene polyisocyanates obtained by phosgenating-aniline/formaldehyde condensation products.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same isocyanuration reaction as in Production Example 1 was carried out except that 3,290 g of hexamethylene diisocyanate and 210 g of "Takenate 500" (xylylene diisocyanate produced by Takeda Chemical Industry Co., Ltd.) were used instead of 3,500 g of hexamethylene diisocyanate, and the amount of the isocyanuration catalyst used in production Example 1 was changed to 4.7 g. There was obtained 4,219 g of the reaction mixture containing the deactivated catalyst. The same isocyanuration reaction as in Production Example 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: diphenylmethane-4,4′-diisocyanate (MDI); hydrogenated diphenylmethane-4,4′-diisocyanate (H12MDI); tetra-methyl xylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI), of the formula OCN—(CH2)6—NCO; naphthalene-1,5-diisocyanate; 3,3′-dimethoxy-4,4′-biphenyldiisocyanate; 3,3′-dimethyl-4,4′-bimethyl-4,4′-biphenyldiisocyanate; phenylene diisocyanate; 4,4′-biphenyldiisocyanate; 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate, of the formulae

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: diphenylmethane-4,4′-diisocyanate (MDI); hydrogenated diphenylmethane-4,4′-diisocyanate (H12MDI); tetra-methyl xylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI), of the formula OCN—(CH2)6—NCO; naphthalene-1,5-diisocyanate; 3,3′-dimethoxy-4,4′-biphenyldiisocyanate; 3,3′-dimethyl-4,4′-bimethyl-4,4′-biphenyldiisocyanate; phenylene diisocyanate; 4,4′-biphenyldiisocyanate; 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate, of the formulae

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, 0.1 g of urethanation catalyst dibutyl tin dilaurate and 0.1 g of polymerization inhibitor hydroquinone monomethyl ether were added to 200 g of the isocyanurate-modified hexamethylene diisocyanate, and 1.2 mols of the hydroxyalkyl acrylate as shown in Table 5 below was dropwise added thereto over a period of 30 minutes with the reaction liquid temperature being kept at 40° C. After addition, the reaction liquid temperature was elevated up to 60° C., and the reaction was continued until the isocyanate group in the reaction liquid disappeared to obtain urethane acrylate oligomer 6 through urethane acrylate oligomer 9 as shown in Table 5. below was dropwise added over a period of 30 minutes with the reaction liquid temperature being kept at 40° C After addition the reaction liquid temperature was elevated up to 60° C. the reaction was continued until the isocyanate group in the reaction liquid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.5 Parts of 7.14-diazadispiro[5.1.5.2]pentadecan-15-one, 2.1 parts of hexamethylene diisocyanate and a trace of 1,4-diazabicyclo[2.2.2]octane in 150 parts of dry benzene were refluxed for 48 hours. The solvent was removed in vacuo and the solid material stirred in 150 parts of water for 30 minutes. The solid was filtered and recrystallised from ethanol to give hexane-1',6'-bis[14-carbamoyl-7,14-diaza dispiro5.1.5.2]pentadecan-15-one] of melting point 164° to 165°C. This material gave the following elemental analysis by weight. The solvent was removed in vacuo The solid was filtered recrystallised from ethanol