GA-NAPHTHALOCYANINE CHROMOPHORES WITH SHORT CHAIN ALKOXY AXIAL SUBSTITUENTS

Abstract

The present invention relates to specific Ga-naphthalocyanine chromophores with short chain alkoxy axial substituents, their use as almost colourless IR absorbers, for optical filter applications; especially for plasma display panels, or for laser welding of plastics. The compounds may be used in compositions for inks, paints and plastics, especially in a wide variety of printing systems and are particularly well-suited for security applications.

Claims

1. A compound of formula (I) ##STR00003## wherein R is C.sub.1-C.sub.6alkyl.

2. A compound according to claim 1 wherein R is C.sub.1-C.sub.5alkyl.

3. A compound according to claim 1, wherein R is ethyl, propyl or butyl.

Description

EXAMPLES

Preparation Examples

Pentoxy-Ga-Naphthalocyanine

[0097] A solution of sodium pentoxide made of 6.2 g sodium in 155 g 1-pentanol is prepared and slowly added to a solution of 15.0 g gallium chloride in 210 g toluene at room temperature. To the resulting suspension is added a mixture of 61.3 g naphthalene-2,3-dicarbonitrile, 240 g triethylenglycol-dimethylether and 240 g toluene. Toluene and the excess of 1-pentanol are distilled off under reduced pressure at 100 C. and the reaction mixture is stirred at 170 C. for 5 hours. The suspension is first cooled to 80 C., 250 g DMF is added, and then further cooled to room temperature. The green solid is collected by filtration, successively washed with DMF, acetone and water and then dried. Yield: 34.2 g (47.1%)

Butoxy-Ga-Naphthalocyanine

[0098] A solution of sodium butoxide made of 6.2 g sodium in 155 g 1-butanol is prepared and slowly added to a solution of 15.0 g gallium chloride in 210 g toluene at room temperature. To the resulting suspension is added a mixture of 61.3 g naphthalene-2,3-dicarbonitrile, 240 g triethylenglycol-dimethylether and 240 g toluene. Toluene and the excess of 1-butanol are distilled off under reduced pressure at 100 C. and the reaction mixture is stirred at 170 C. for 7 hours. The suspension is first cooled to 80 C., 250 g DMF is added, and then further cooled to room temperature. The green solid is collected by filtration, successively washed with DMF, acetone and water and then dried. Yield: 46.6 g (65.3%)

Propoxy-Ga-Naphthalocyanine

[0099] A solution of sodium propoxide made of 10.4 g sodium in 260 g 1-propanol is prepared and slowly added to a solution of 25.0 g gallium chloride in 280 g toluene at room temperature. To the resulting suspension is added a mixture of 102.4 g naphthalene-2,3-dicarbonitrile, 300 g triethylenglycol-dimethylether and 300 g toluene. Toluene and the excess of 1-propanol are distilled off under reduced pressure at 100 C. and the reaction mixture is stirred at 170 C. for 6 hours. The suspension is first cooled to 80 C., 360 g DMF is added, and then further cooled to room temperature. The green solid is collected by filtration, successively washed with DMF, acetone and water and then dried. Yield: 49.8 g (42.5%)

Ethoxy-Ga-Naphthalocyanine

[0100] A solution of sodium ethoxide made of 10.4 g sodium in 260 g ethanol is prepared and slowly added to a solution of 25.0 g gallium chloride in 280 g toluene at room temperature. To the resulting suspension is added a mixture of 102.4 g naphthalene-2,3-dicarbonitrile, 300 g triethylenglycol-dimethylether and 300 g toluene. Toluene and the excess of ethanol are distilled off by heating to 100 C. under slightly reduced pressure and the reaction mixture is stirred at 170 C. for 6 hours. The suspension is first cooled to 80 C., 360 g DMF is added, and then further cooled to room temperature. The green solid is collected by filtration, successively washed with DMF, acetone and water and then dried. Yield: 43.4 g (36.9%)

Methoxy-Ga-Naphthalocyanine

[0101] A solution of sodium methoxide made of 10.4 g sodium in 260 g methanol is prepared and slowly added to a solution of 25.0 g gallium chloride in 280 g toluene at room temperature. To the resulting suspension is added a mixture of 102.4 g naphthalene-2,3-dicarbonitrile, 300 g triethylenglycol-dimethylether and 300 g toluene. Toluene and the excess of methanol are distilled off by heating to 100 C. under slightly reduced pressure and the reaction mixture is stirred at 170 C. for 6 hours. The suspension is first cooled to 80 C., 360 g DMF is added, and then further cooled to room temperature. The green solid is collected by filtration, successively washed with DMF, acetone and water and then dried. Yield: 44.6 g (38.6%)

[0102] Pigment finishing methods can be optionally applied to the materials described in the examples above, e. g. kneading or milling.

Application Example

[0103] An offset ink is prepared by mixing the following components by means of an automatic pigment muller:

TABLE-US-00001 Offset varnish 1000 mg IR absorber, prepared as described above 40 mg (crude or after pigment finishing) Siccative 20 mg

[0104] Immediately afterwards the freshly prepared offset ink is printed onto cotton paper with a printability tester (IGT Orange Proofer). Ink transfer: 1 gram/square centimeter. Remission curves are measured afterwards with an UV/VIS/IR spectrophotometer. The remission values are given in the following Table 1.

TABLE-US-00002 TABLE 1 % R Propoxy-Ga- % R Butoxy-Ga- % R Propoxy-Ga- % R Butoxy-Ga- Naphthalocyanine Naphthalocyanine Naphthalocyanine Naphthalocyanine Wavelength crude crude kneaded kneaded 1600 90.0 91.0 88.2 88.9 1590 90.3 91.2 88.7 89.3 1580 90.5 91.4 88.7 89.4 1570 90.6 91.5 88.8 89.4 1560 90.7 91.7 89.0 89.7 1550 90.9 91.8 89.4 89.9 1540 90.8 91.7 89.3 89.8 1530 90.7 91.8 89.1 89.8 1520 90.7 91.7 89.1 89.6 1510 90.6 91.7 89.3 89.8 1500 90.9 91.7 89.3 89.9 1490 91.1 91.8 89.4 89.9 1480 91.1 92.0 89.6 90.0 1470 90.8 91.7 89.3 89.7 1460 90.4 91.3 88.7 89.2 1450 90.1 91.1 88.4 88.9 1440 89.6 90.7 88.0 88.6 1430 89.0 90.1 87.6 88.1 1420 88.4 89.6 86.8 87.4 1410 88.0 89.1 86.4 87.0 1400 87.6 88.8 85.9 86.7 1390 87.5 88.6 85.9 86.6 1380 87.7 88.8 86.1 86.8 1370 87.8 89.0 86.3 86.9 1360 87.9 89.1 86.4 86.9 1350 87.9 89.2 86.3 87.0 1340 87.9 89.3 86.5 87.2 1330 88.0 89.4 86.7 87.2 1320 88.0 89.5 86.8 87.3 1310 88.0 89.4 86.9 87.4 1300 88.1 89.4 87.0 87.4 1290 88.1 89.4 86.9 87.4 1280 88.2 89.5 86.9 87.5 1270 88.3 89.5 87.0 87.6 1260 88.2 89.5 87.1 87.5 1250 88.3 89.5 87.1 87.5 1240 88.3 89.5 87.0 87.6 1230 88.1 89.4 86.9 87.5 1220 88.1 89.2 86.9 87.3 1210 88.0 89.2 86.7 87.2 1200 87.8 89.0 86.8 87.2 1190 87.8 88.9 86.6 87.0 1180 87.8 88.9 86.7 87.1 1170 87.9 89.1 86.6 87.2 1160 88.1 89.3 86.8 87.4 1150 88.1 89.4 86.9 87.4 1140 88.1 89.5 87.0 87.5 1130 88.1 89.4 87.1 87.5 1120 88.2 89.5 87.3 87.7 1110 88.1 89.7 87.2 87.8 1100 87.8 89.7 87.3 87.9 1090 87.5 89.6 87.3 87.7 1080 86.9 89.5 87.3 87.6 1070 86.2 89.2 87.0 87.4 1060 85.2 88.9 86.7 87.0 1050 84.2 88.5 86.3 86.6 1040 83.3 88.1 86.1 86.1 1030 82.3 87.6 85.6 85.6 1020 81.4 86.9 84.8 84.6 1010 80.4 86.0 84.0 83.4 1000 79.4 85.0 82.8 82.0 990 78.4 83.9 81.6 80.3 980 77.2 82.4 79.9 78.3 970 75.6 80.7 78.0 75.9 960 73.5 78.8 75.4 73.2 950 71.1 76.7 72.5 70.2 940 68.3 74.5 68.8 66.9 930 65.3 72.6 64.8 63.5 920 62.2 70.8 60.6 60.2 910 59.4 69.3 56.5 57.2 900 57.2 68.2 52.9 54.8 890 55.5 67.5 50.2 52.7 880 54.7 66.9 47.9 51.0 870 54.2 66.6 46.2 49.3 860 54.0 66.1 44.0 47.4 850 53.1 65.1 41.7 45.6 840 50.2 61.7 35.7 39.7 830 50.1 61.4 35.0 38.7 820 50.1 60.6 34.6 38.0 810 50.2 60.3 34.5 37.6 800 50.5 60.5 34.6 37.3 790 50.5 60.8 34.2 36.6 780 50.6 60.9 33.4 35.7 770 50.4 60.7 32.0 34.2 760 50.3 60.4 30.3 32.5 750 50.6 60.4 28.9 31.0 740 51.4 60.9 28.4 30.4 730 52.9 62.1 29.3 31.1 720 55.0 63.8 31.7 33.0 710 57.2 65.8 35.1 36.0 700 59.5 67.8 39.1 39.7 690 62.0 69.9 43.5 43.8 680 64.6 72.2 48.2 48.4 670 67.7 74.5 53.5 53.7 660 70.6 76.8 58.7 58.7 650 73.3 79.0 63.8 63.8 640 75.8 80.9 68.5 68.4 630 78.0 82.6 72.5 72.4 620 79.9 84.0 75.9 75.8 610 81.8 85.3 78.6 78.5 600 83.3 86.2 80.6 80.5 590 84.6 87.0 82.1 81.8 580 85.6 87.6 83.0 82.8 570 86.3 88.2 83.7 83.6 560 86.6 88.4 83.9 83.8 550 86.3 88.2 83.3 83.1 540 85.2 87.5 82.0 81.9 530 83.9 86.7 80.8 81.1 520 83.4 86.4 80.5 81.0 510 82.9 86.0 79.8 80.2 500 81.5 85.0 77.5 77.6 490 78.2 82.7 72.3 72.6 480 72.6 79.2 65.1 65.8 470 67.5 76.2 58.6 60.0 460 66.4 75.2 56.2 57.8 450 67.2 75.7 56.2 57.3 440 66.9 76.1 54.9 56.1 430 67.0 76.7 54.1 55.6 420 67.9 78.1 54.1 55.7 410 68.7 79.5 53.5 55.4 400 69.7 81.0 52.4 54.5