Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2000-02-17
2002-06-25
Hoke, Veronica P. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C252S587000, C524S145000
Reexamination Certificate
active
06410613
ABSTRACT:
TECHNICAL FIELD
The present invention relates to novel phosphate compounds and a preparation process thereof, novel phosphate copper compounds and a preparation process thereof, near infrared ray absorbers containing a copper ion, and near infrared ray-absorbing acrylic resin compositions having excellent visible ray-transmitting property and performance that near infrared rays are absorbed with high efficiency.
BACKGROUND ART
A great number of attempts have heretofore been made to impart performance that near infrared rays are absorbed with high efficiency to synthetic resins. For example, resin compositions in which an organic pigment having near infrared ray-absorbing ability is contained in an acrylic resin have been known (see Japanese Patent Application Laid-Open No. 42622/1993).
However, such a resin composition involves problems that it cannot absorb near infrared rays over a wide wavelength region because the near infrared ray-absorption wavelength region of the organic pigment itself is narrow and that this organic pigment is easy to be deteriorated by ultraviolet rays for reasons of its chemical structure, and thus the near infrared ray-absorbing ability of the pigment is lowered, and the initial near infrared ray-absorbing ability of the resin composition cannot be hence retained over a long period of time.
Compositions in which a copper ion is contained as a near infrared ray absorber in an acrylic resin have been known as resin composition having performance that near infrared rays are absorbed (see Japanese Patent Publication No. 5190/1987).
However, such a resin composition involves problems that it is difficult to contain the copper ion in a state sufficiently dispersed in the acrylic resin, and so sufficiently high near infrared ray-absorbing ability cannot be attained, and the transmittance of visible rays is reduced.
It has also been known to add a phosphate group-containing compound such as a phosphate to a synthetic resin to enhance the dispersibility of the copper ion in the synthetic resin (see Japanese Patent Publication No. 5190/1987).
However, such a means involves a problem that since the compatibility of the phosphate group-containing compound with the synthetic resin is not sufficiently high, any resin composition having excellent visible ray-transmitting property is not provided.
DISCLOSURE OF THE INVENTION
The present invention has been made in view of the foregoing circumstances.
It is the first object of the present invention to provide a novel phosphate compound by which a copper ion can be dispersed in a high proportion in a synthetic resin, thereby providing a resin composition which has excellent visible ray-transmitting property and performance that near infrared rays are absorbed with high efficiency, and is little in the deterioration of its near infrared ray-absorbing ability by ultraviolet rays.
The second object of the present invention is to provide a process capable of preparing the novel phosphate compound described above with advantages.
The third object of the present invention is to provide a near infrared ray absorber which contains a copper ion and by which the copper ion can be dispersed in a high proportion in a synthetic resin.
The fourth object of the present invention is to provide a novel phosphate copper compound which has performance that near infrared rays are absorbed with high efficiency, and is little in the deterioration of its near infrared ray-absorbing ability by ultraviolet rays and satisfactory in compatibility with synthetic resins.
The fifth object of the present invention is to provide a process capable of preparing the novel phosphate copper compound described above with advantages.
The sixth object of the present invention is to provide a near infrared ray absorber which is satisfactory in compatibility with synthetic resins and can provide a resin composition which absorbs near infrared rays with high efficiency.
The seventh object of the present invention is to provide a near infrared ray-absorbing acrylic resin composition which has excellent visible ray-transmitting property and performance that near infrared rays are absorbed with high efficiency and is little in the deterioration of its near infrared ray-absorbing ability by ultraviolet rays.
The present inventors have found that a phosphate compound having a specific structure has performance that a copper ion can be dispersed in a high proportion in a synthetic resin, thus leading to completion of the present invention.
A phosphate compound according to the present invention is represented by the following formula (1):
wherein groups R independently mean a group represented by the following formula (2) or (3), and n is 1 or 2:
wherein R
1
denotes an alkyl group having 1 to 20 carbon atoms, R
2
represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and m is an integer of 1 to 6.
The phosphate compound according to the present invention can be easily prepared in accordance with any one of the following first, second and third processes.
(First Process)
The process comprises reacting an alcohol represented by the following formula (4) or (5) with phosphorus pentoxide:
wherein R
1
denotes an alkyl group having 1 to 20 carbon atoms, R
2
represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and m is an integer of 1 to 6.
(Second Process)
The process comprises reacting the alcohol represented by the formula (4) or (5) with a phosphorus oxyhalide, and hydrolyzing the resultant product.
(Third Process)
The process comprises reacting the alcohol represented by the formula (4) or (5) with phosphorus trihalide, thereby synthesizing a phosphonate compound, and oxidizing the phosphonate compound.
A near infrared ray absorber according to the present invention comprises the phosphate compound represented by the formula (1) and a copper ion;
A phosphate copper compound according to the present invention is obtained by reacting the phosphate compound represented by the formula (1) with a copper salt.
The phosphate copper compound according to the present invention is represented by the following formula (6) or (7):
wherein groups R independently mean a group represented by the following formula (2) or (3), and M denotes a copper ion:
wherein R
1
denotes an alkyl group having 1 to 20 carbon atoms, R
2
represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and m is an integer of 1 to 6.
A process for preparing a phosphate copper compound according to the present invention comprises reacting the phosphate compound represented by the formula (1) with a copper salt.
In the preparation process of the phosphate copper compound according to the present invention, the phosphate compound represented by the formula (1) is reacted with the copper salt in an organic solvent, and an acid component formed by the reaction of the phosphate compound with the copper salt and the organic solvent are then removed.
Alternatively, an organic solvent layer containing the phosphate compound represented by the formula (1) and an alkali in an organic solvent insoluble or hardly soluble in water, is brought into contact with a water layer in which the copper salt is dissolved, thereby reacting the phosphate compound with the copper salt, and the organic layer and the water layer are then separated from each other.
A near infrared ray absorber according to the present invention comprises the phosphate copper compound described above as an effective ingredient.
A near infrared ray-absorbing acrylic resin composition according to the present invention comprises an acrylic resin, and the following component (A) and/or component (B) contained in the acrylic resin: Component (A): a component composed of a copper ion and a phosphate compound represented by the formula (l); Component (B): a component composed of a compound obtained by reacting a phosphate compound represented by the formula (1) with a copper salt.
In the near infrared ray-absorbing acrylic resin composition according to the present invention, the component (B) may
Katono Hiroki
Ohnishi Yasuhiro
Hoke Veronica P.
Kureha Kagaku Kogyo Kabushiki Kaisha
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