7a-methyl-4,5,6,7-tetrahydro-3aH-2-benzofuran-1,3-dione

Conditions: temp:112.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.35 g (0.005 mol) of the diketopyrrolopyrrole of the formula XIX (Example 6) and 30 ml of dichlorobenzene are placed under nitrogen in a sulfonating flask, 5.0 mg (0.05 mmol) of thiodiphenylamine are added, and the mixture is heated with stirring at 110-115° C. 3.17 g (0.010 mol) of the methyl-hexahydrophthalic acid derivative (isomer mixture) of the formula ##STR43## (obtained by generally known methods from methylhexahydrophthalic anhydride and hydroxyethyl methacrylate) are added dropwise with vigorous stirring over the course of 15 minutes to the clear orange-red solution, stirring is continued for about 2 hours at 110-115° C., and then the mixture is cooled to room temperature. The clear dark red solution is washed in a separating funnel 3 times with 20 ml of 5% sodium hydroxide solution and 2 times with 30 ml of deionized water, and the organic phase is dried over MgSO4.H2O, filtered and concentrated to dryness under a high vacuum. The resulting product is recrystallized from 30 ml of ethanol, to give 3.05 g (81.3% of theory) of a crystalline product formula ##STR44## R= ##STR45## with a melting point of 69.6° C. the mixture is heated

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

Procedure: The liquid, organic acid anhydrides which are used as epoxy resin curing agents in carrying out the invention, include 1-methyl hexahydrophthalic anyhydride, 1-methyltetrahydrophthalic anhydride, NADIC anhydride, NADIC methyl anhydride, and the like liquid anhydrides; and blends of hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, pyromellitic dianhydride, polyazelaic polyanhydride, the reaction product of trimellitic anhydride and a glycol, and benzophenone tetracarboxylic acid dianhydride solids with any of the above liquid anhydrides, to provide a liquid admixture of anhydrides. The anhydrides may be used singly or in admixture but the resultant material must be a liquid.

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methyl-hexahydrophthalic anhydride (Also known as 4-methyl-1,2-cyclohexanedicarboxylic anhydride; 210.0 g, 1.25 mol, CAS #19438-60-9, Alfa Aesar, lot B04w039), 4-(dimethylamino)pyridine (DMAP, 7.5 g, 0.06 mol, CAS #1122-58-3, Alfa Aesar, lot L125009), 2-hydroxyethylmethacrylate (HEMA, 162.5 g, 1.25 mol, and butylated hydroxytoluene (BHT, 0.380 g) were charged into a 1-liter 3-neck reaction flask equipped with a mechanical stirrer, a thermocouple connected to a temperature controller, a dry air stream running through a T-shape connection into the reactor then to an oil bubbler, and a heating mantle. The mixture was continuously stirred at 95° C. for 5 hours. The heat was turned off and the flask contents were allowed to cool to room temperature to give 4-methyl-(2-methacryloyloxyethyl)hexahydrophthalic acid intermediate as a colorless viscous liquid. Structure was confirmed by NMR. equipped with a mechanical stirrer to cool to room temperature

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

Procedure: The procedures of Example 1 were repeated except that 38.2 g. of methylhexahydrophthalic anhydride (Example 2) and 61.2 g. of dodecenylsuccinic anhydride (Example 3) which was a maleinization product of propylene tetramer or butylene trimer, were employed, respectively, instead of 34 g. of phthalic anhydride, to give light yellow resins. The properties thereof are shown in Table 1.

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

Procedure: The liquid, organic acid anhydrides which are used as epoxy resin curing agents in carrying out the invention, include 1-methyl hexahydrophthalic anyhydride, 1-methyltetrahydrophthalic anhydride, NADIC anhydride, NADIC methyl anhydride, and the like liquid anhydrides; and blends of hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, pyromellitic dianhydride, polyazelaic polyanhydride, the reaction product of trimellitic anhydride and a glycol, and benzophenone tetracarboxylic acid dianhydride solids with any of the above liquid anhydrides, to provide a liquid admixture of anhydrides. The anhydrides may be used singly or in admixture but the resultant material must be a liquid.

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

Procedure: The aforesaid methylhexahydrophthalic anhydride which was liquid at ordinary temperatures was a mixture of 70% by weight of 4-methylhexahydrophthalic anhydride which was liquid at ordinary temperatures and was obtained by hydrogenating 4-methyl-Δ4 -tetrahydrophthalic anhydride at 150° C. in the presence of Raney nickel catalyst and 30% by weight of 3-methylhexahydrophthalic anhydride which was liquid at ordinary temperatures and was obtained by hydrogenating 3-methyl-Δ4 -tetrahydrophthalic anhydride in the same manner as described above.

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

Procedure: tetrahydrophthalic anhydride (referred to as THPA); and methylhexahydrophthalic anhydride (referred to as Me-HHPA).

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

Procedure: 2.35 g (0.005 mol) of the diketopyrrolopyrrole of the formula XIX (Example 6) and 30 ml of dichlorobenzene are placed under nitrogen in a sulfonating flask, 5.0 mg (0.05 mmol) of thiodiphenylamine are added, and the mixture is heated with stirring at 110°-115° C. 3.17 g (0.010 mol) of the methyl-hexahydrophthalic acid derivative (isomer mixture) of the formula ##STR43## (obtained by generally known methods from methylhexahydrophthalic anhydride and hydroxyethyl methacrylate) are added dropwise with vigorous stirring over the course of 15 minutes to the clear orange-red solution, stirring is continued for about 2 hours at 110°-115° C., and then the mixture is cooled to room temperature. The clear dark red solution is washed in a separating funnel 3 times with 20 ml of 5% sodium hydroxide solution and 2 times with 30 ml of deionized water, and the organic phase is dried over MgSO4 ·H2O, filtered and concentrated to dryness under a high vacuum. The resulting product is recrystallized from 30 ml of ethanol, to give 3.05 g (81.3% of theory) of a crystalline product of the formula ##STR44## with a melting point of 69.6° C. the mixture is heated

Conditions: temp:112.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.35 g (0.005 mol) of the diketopyrrolopyrrole of the formula XIX (Example 6) and 30 ml of dichlorobenzene are placed under nitrogen in a sulfonating flask, 5.0 mg (0.05 mmol) of thiodiphenylamine are added, and the mixture is heated with stirring at 110-115° C. 3.17 g (0.010 mol) of the methyl-hexahydrophthalic acid derivative (isomer mixture) of the formula ##STR43## (obtained by generally known methods from methylhexahydrophthalic anhydride and hydroxyethyl methacrylate) are added dropwise with vigorous stirring over the course of 15 minutes to the clear orange-red solution, stirring is continued for about 2 hours at 110-115° C., and then the mixture is cooled to room temperature. The clear dark red solution is washed in a separating funnel 3 times with 20 ml of 5% sodium hydroxide solution and 2 times with 30 ml of deionized water, and the organic phase is dried over MgSO4.H2O, filtered and concentrated to dryness under a high vacuum. The resulting product is recrystallized from 30 ml of ethanol, to give 3.05 g (81.3% of theory) of a crystalline product formula ##STR44## R= ##STR45## with a melting point of 69.6° C. the mixture is heated

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methyl-hexahydrophthalic anhydride (Also known as 4-methyl-1,2-cyclohexanedicarboxylic anhydride; 210.0 g, 1.25 mol, CAS #19438-60-9, Alfa Aesar, lot B04w039), 4-(dimethylamino)pyridine (DMAP, 7.5 g, 0.06 mol, CAS #1122-58-3, Alfa Aesar, lot L125009), 2-hydroxyethylmethacrylate (HEMA, 162.5 g, 1.25 mol, and butylated hydroxytoluene (BHT, 0.380 g) were charged into a 1-liter 3-neck reaction flask equipped with a mechanical stirrer, a thermocouple connected to a temperature controller, a dry air stream running through a T-shape connection into the reactor then to an oil bubbler, and a heating mantle. The mixture was continuously stirred at 95° C. for 5 hours. The heat was turned off and the flask contents were allowed to cool to room temperature to give 4-methyl-(2-methacryloyloxyethyl)hexahydrophthalic acid intermediate as a colorless viscous liquid. Structure was confirmed by NMR. equipped with a mechanical stirrer to cool to room temperature