Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2000-10-04
2001-06-12
Acquah, Samuel A. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C558S082000, C558S122000, C528S281000, C528S285000, C528S302000, C528S308000, C528S403000, C528S414000
Reexamination Certificate
active
06245880
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an organophosphorous composition comprising, as a principal component, an organophosphorous compound represented by the general formula (1):
wherein R
1
and R
2
represent an organic group or a halogen atom, and m and n represent an integer of 0 to 4, provided that R
1
and R
2
may be the same or different when m or n is an integer of 2 to 4, and a predetermined amount of a divalent metallic compound.
The present invention also relates to a method of producing the organophosphorous composition represented by the general formula (1).
The present invention relates to an organophosphorous composition comprising an organophosphorous compound represented by the general formula (4):
wherein R
1
, R
2
, m and n are as defined above and A represents an organic group which is the same as or different from that of R
1
and R
2
, which is derived from the organophosphorous compound represented by the general formula (1) in the organophosphorous composition, and a predetermined amount of a divalent metallic compound.
The present invention also relates to a polyester composition comprising polyester having a predetermined amount of a phosphorous atom related to an organophosphorous compound wherein an organic group (A) in the general formula (4) is an ester-forming functional group (B), and a predetermined amount of a divalent metallic compound, and a method of producing the same.
The organophosphorous composition comprising the organophosphorous compound represented by the general formula (1) or (4) is used for various purposes, for example, raw materials for polymer compounds, lubricating oils, antioxidants for organic compounds, flame retarders, plasticizers, bactericides, color protection agents, polymerization initiators and the like. Particularly, those wherein an organic group (A) in the general formula (4) is an ester-forming functional group (B) are useful as a copolymer component of the polyester, and are capable of producing a flame-retardant polyester.
2. Description of the Related Art
Organophosphorous compounds (also referred to as “DOP”, hereinafter) such as 6-oxo-(6H)-dibenzo-(c,e)(1,2)-oxaphosphorine, which are presented by the general formula (1), have hitherto been disclosed in production methods described in Japanese Examined Patent Publication (Kokoku) No. Sho 49-45397 and Japanese Examined Patent Publication (Kokoku) No. Sho 50-17979, and recent publications such as Japanese Unexamined Patent Publication (Kokai) No. Hei 10-1490, Japanese Unexamined Patent Publication (Kokai) No. Hei 7-145185, Japanese Unexamined Patent Publication (Kokai) No. Hei 8-99983 and Published Japanese Translation No. Hei 10-510545 of the PCT Application.
DOP has been produced by reacting an orthophenylphenol compound (also referred to as “OPP”, hereinafter) represented by the general formula (2):
wherein R
1
, R
2
, m and n are as defined above, with a phosphorous compound such as phosphorous trihalide (PX
3
: X represents a halogen atom), condensing the reaction product with heating in the presence of a Friedel-Crafts catalyst containing zinc chloride to produce a compound represented by the general formula (3):
wherein R
1
, R
2
, m and n are as defined above and X represents a halogen atom, and hydrolyzing the compound (also referred to as “DOP-X”, hereinafter) with water under heating.
In such a method, however, a zinc compound such as zinc chloride as the Friedel-Crafts catalyst used in the production of DOP-X is remained in the resulting DOP. Since the divalent metallic compound such as zinc compound forms a complex with DOP thus forming an insoluble matter during the reaction between DOP and the other organic compound, DOP containing a small amount of the divalent metal is required.
In case a compound derived from DOP, as a flame retarder component, is used in a copolymer component of the polyester, an antimony compound such as antimony trioxide used as a polymerization catalyst of the polyester is reduced by DOP, thereby causing a problem that the resulting polyester is blackish.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a composition containing DOP, which does not form a complex during the reaction between DOP and an organic compound and can satisfactorily maintain a color tone of the resulting polyester even in case of using a compound derived from DOP in a copolymer component of a polyester.
Another object of the present invention is to provide a method which can produce DOP whose zinc content is reduced to the degree where a complex is not formed during the reaction with an organic compound, and to provide a method which can produce DOP capable of satisfactorily maintaining a color tone of the resulting polyester even in case of using a DOP-derived compound in a copolymer component of a polyester.
A still another object of the present invention is to provide the DOP derivative composition described above, and to provide a polyester having a good color tone and a method of producing the same using the DOP derivative composition.
The present inventors have studied intensively to solve the problems described above and found that the objects described above can be attained by the following means, thus completing the present invention.
The objects described above of the present invention can be attained by the following means.
1. An organophosphorous composition comprising, as a principal component, an organophosphorous compound represented by the general formula (1):
wherein R
1
and R
2
represent an organic group or a halogen atom, and m and n represent an integer of 0 to 4, provided that R
1
and R
2
may be the same or different when m or n is an integer of 2 to 4, the composition further comprising, as a compound other than the organophosphorous compound, a divalent metallic compound in an amount more than 30 ppm and not more than 2300 ppm in terms of a divalent metal based on the organophosphorous compound.
2. The organophosphorous composition according to claim
1
, wherein the divalent metal is zinc.
3. The organophosphorous composition according to claim
1
, wherein the compound other than the organophosphorous compound is a halogen compound, the content of the halogen compound is not more than 250 ppm in terms of an amount of a halogen atom based on the organophosphorous compound.
4. The organophosphorous composition according to claim
1
, which does not substantially contain an organic compound other than the organophosphorous compound.
5. The organophosphorous composition according to claim
1
, which is in the form of powder.
6. A method of producing an organophosphorous compound represented by the general formula (1):
wherein R
1
and R
2
represent an organic group or a halogen atom, and m and n represent an integer of 0 to 4, provided that R
1
and R
2
may be the same or different when m or n is an integer of 2 to 4, which comprises the steps of:
reacting an orthophenylphenol compound represented by the general formula (2):
wherein R
1
and R
2
are as defined above, with phosphorous trihalide (PX
3
: X represents a halogen atom) and condensing the reaction product with heating in the presence of a Friedel-Crafts catalyst containing zinc chloride to produce an organophosphorous compound represented by the general formula (3):
wherein R
1
and R
2
are as defined above and X represents a halogen atom; and
hydrolyzing the compound represented by the general formula (3) with water; the compound represented by the general formula (3) and water in the hydrolysis step are used in an equimolar ratio and that the method further comprises a step of purifying the organophosphorous compound represented by the general formula (1) by further hydrolyzing the organophosphorous compound represented by the general formula (1), which is obtained by passing through the hydrolysis step, followed by cyclodehydration.
7. The method of producing the organophosphorous compound according to claim
6
, wherein the compound represented by the general formula (2), w
Gyobu Shoichi
Sato Maki
Takeuchi Hideo
Acquah Samuel A.
Kenyon & Kenyon
Toyo Boseki Kabushiki Kaisha
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