3-(Dodecenyl)dihydro-2,5-furandione

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 313.5 g (1.98 mol) calcium acetate in 1000 ml water was added to a solution of 570 g (1.98 mol) dodecenyl succinic anhydride in 1000 ml isopropanol. The mixture was then heated to 90° C., left at that temperature for 1.5 h and then concentrated in a water jet vacuum. The residue was dried in vacuo in a drying cabinet at 100° C. 680 g of the calcium soap were obtained in the form of a colorless powder. concentrated in a water jet vacuum The residue was dried in vacuo in a drying cabinet at 100° C

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

Procedure: A 500 ml, two-neck flask was charged with 105.2 g (500 mmol) dodecenylsuccinic anhydride 100 ml toluene. The flask was equipped with a thermometer and immersed in a water bath. Diallylamine (48.6 g, 500 mmol) was then dripped into the magnetically stirred anhydride plus toluene solution over a 15-minute period. Ice was added to the water bath as required to prevent temperature of the reaction mixture from getting above 35° C. The mixture was then stirred for another 45 minutes at room temperature. The toluene was then removed via rotary evaporator and air sparge to yield 153.4 g (99.8% of theory) of a red, oily liquid. An FTIR trace on this compound was found to have significant absorptions at 2924, 1726, 1605, 1440, 1221, 1174, 972, and 922 wavenumbers. The flask was equipped with a thermometer immersed in a water bath from getting above 35° C The toluene was then removed via rotary evaporator and air sparge to yield 153.4 g (99.8% of theory) of a red, oily liquid

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

Procedure: A 500 ml, two-neck flask was charged with 52.6 g (500 mmol) diethanolamine and 50 ml toluene. A temperature probe was placed into this solution through one of the necks of the flask and the flask was immersed into a water bath. A solution of 105.2 g (500 mmol) dodecenylsuccinic anhydride dissolved in 200 ml toluene was dripped into the magnetically stirred solution diethanolamine solution over a 40-minute period. Ice was added to the water bath as required to prevent temperature of the reaction mixture from getting above 25° C. The mixture was then stirred for another 2.5 hours at room temperature. The complete disappearance of the anhydride functional group was confirmed by infrared spectroscopy. The FTIR trace on this compound had significant absorptions at 2957, 2924, 2858, 1733, 1616, 1560, 1415, 1160, 1069, 969, and 728 wavenumbers. The solution was concentrated down to 50% solids in toluene and was then set aside for later use. the flask was immersed into a water bath from getting above 25° C The solution was concentrated down to 50% solids in toluene

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

Procedure: A 500 ml, two-neck flask was charged with 52.6 g (500 mmol) diethanolamine and 50 ml toluene. A temperature probe was placed into this solution through one of the necks of the flask and the flask was immersed into a water bath. A solution of 105.2 g (500 mmol) dodecenylsuccinic anhydride dissolved in 200 ml toluene was dripped into the magnetically stirred solution diethanolamine solution over a 40-minute period. Ice was added to the water bath as required to prevent temperature of the reaction mixture from getting above 25° C. The mixture was then stirred for another 2.5 hours at room temperature. The complete disappearance of the anhydride functional group was confirmed by infrared spectroscopy. The FTIR trace on this compound had significant absorptions at 2957, 2924, 2858, 1733, 1616, 1560, 1415, 1160, 1069, 969, and 728 wavenumbers. The solution was concentrated down to 50% solids in toluene and was then set aside for later use. the flask was immersed into a water bath from getting above 25° C The solution was concentrated down to 50% solids in toluene

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 313.5 g (1.98 mol) calcium acetate in 1000 ml water was added to a solution of 570 g (1.98 mol) dodecenyl succinic anhydride in 1000 ml isopropanol. The mixture was then heated to 90° C., left at that temperature for 1.5 h and then concentrated in a water jet vacuum. The residue was dried in vacuo in a drying cabinet at 100° C. 680 g of the calcium soap were obtained in the form of a colorless powder. concentrated in a water jet vacuum The residue was dried in vacuo in a drying cabinet at 100° C

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 313.5 g (1.98 mol) calcium acetate in 1000 ml water was added to a solution of 570 g (1.98 mol) dodecenyl succinic anhydride in 1000 ml isopropanol. The mixture was then heated to 90° C., left at that temperature for 1.5 h and then concentrated in a water jet vacuum. The residue was dried in vacuo in a drying cabinet at 100° C. 680 g of the calcium soap were obtained in the form of a colorless powder. concentrated in a water jet vacuum The residue was dried in vacuo in a drying cabinet at 100° C

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:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 mol of dodecenylsuccinic anhydride, 0.9 mol of propylene glycol and 40% by weight heavy aromatic naphtha was heated at 130° C. in a 1 L 3-necked, round bottomed flask equipped with a condenser and a mechanical stirrer for 6.5 hours. round bottomed flask equipped with a condenser and a mechanical stirrer for 6.5 hours

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 mol of dodecenylsuccinic anhydride, 0.9 mol of propylene glycol and 40% by weight heavy aromatic naphtha was heated at 130° C. in a 1 L 3-necked, round bottomed flask equipped with a condenser and a mechanical stirrer for 6.5 hours. round bottomed flask equipped with a condenser and a mechanical stirrer for 6.5 hours

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

Procedure: Suitable hardeners (C) for powder resins of the invention also include all those compounds known for this purpose, in particular anhydride hardeners such as, for example: phthalic anhydride, tetrahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, nadicmethyl anhydride (trivial name for isomers of methylendomethylenetetrahydrophthalic anhydride), chlorendic(HET) anhydride (3,4,5,6,7,7-hexachloro-3,6-endomethylenetetrahydrophthalic anhydride), pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, trimellitic anhydride, hardeners corresponding to the component (B) from DE 2 556 182 (which is herein incorporated by reference), dodecenylsuccinic anhydride, isooctenylsuccinic anhydride, etc., dicyandiamide which is produced, for example, under the trade name Dyhard® from SKW Trosberg, phenolic hardeners such as, for example, see Dow® hardeners D.E.H. 80, D.E.H. 82, D.E.H. 84, carboxylic acid salts of imidazole or imidazoline compounds, fusible, soluble adducts which are obtained by reaction of an epoxide compound with imidazole or imidazoline compounds or their carboxylic acid salts.

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

Procedure: Suitable hardeners (C) for powder resins of the invention also include all those compounds known for this purpose, in particular anhydride hardeners such as, for example: phthalic anhydride, tetrahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, nadicmethyl anhydride (trivial name for isomers of methylendomethylenetetrahydrophthalic anhydride), chlorendic(HET) anhydride (3,4,5,6,7,7-hexachloro-3,6-endomethylenetetrahydrophthalic anhydride), pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, trimellitic anhydride, hardeners corresponding to the component (B) from DE 2 556 182 (which is herein incorporated by reference), dodecenylsuccinic anhydride, isooctenylsuccinic anhydride, etc., dicyandiamide which is produced, for example, under the trade name Dyhard® from SKW Trosberg, phenolic hardeners such as, for example, see Dow® hardeners D.E.H. 80, D.E.H. 82, D.E.H. 84, carboxylic acid salts of imidazole or imidazoline compounds, fusible, soluble adducts which are obtained by reaction of an epoxide compound with imidazole or imidazoline compounds or their carboxylic acid salts.

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

Procedure: Suitable hardeners (C) for powder resins of the invention also include all those compounds known for this purpose, in particular anhydride hardeners such as, for example: phthalic anhydride, tetrahydrophthalic anhydride, 4-methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, nadicmethyl anhydride (trivial name for isomers of methylendomethylenetetrahydrophthalic anhydride), chlorendic(HET) anhydride (3,4,5,6,7,7-hexachloro-3,6-endomethylenetetrahydrophthalic anhydride), pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, trimellitic anhydride, hardeners corresponding to the component (B) from DE 2 556 182 (which is herein incorporated by reference), dodecenylsuccinic anhydride, isooctenylsuccinic anhydride, etc., dicyandiamide which is produced, for example, under the trade name Dyhard® from SKW Trosberg, phenolic hardeners such as, for example, see Dow® hardeners D.E.H. 80, D.E.H. 82, D.E.H. 84, carboxylic acid salts of imidazole or imidazoline compounds, fusible, soluble adducts which are obtained by reaction of an epoxide compound with imidazole or imidazoline compounds or their carboxylic acid salts.