Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant
Reexamination Certificate
1999-08-12
2001-01-30
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From sulfur-containing reactant
C528S374000, C528S377000, C528S486000, C528S495000, C523S427000, C523S428000, C521S043000, C521S044000
Reexamination Certificate
active
06180753
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for treating a compound having epithio structure for disposal, and more particularly to a process for treating for disposal an unused portion of a mixture comprising a compound having epithio structures and a catalyst for curing the compound obtained in a process comprising casting and polymerizing the mixture to produce an optical material, such as a plastic lens, a prism, an optical fiber, an information recording substrate and a filter.
2. Description of the Related Arts
The present inventors have discovered novel compounds having epithio structures which provide optical materials having useful properties as optical materials, i.e., a small thickness, a small chromatic aberration, a refractive index of 1.7 or more and an Abbe number of 35 or more as described in the specifications of patent application for these compounds (Japanese Patent Application Laid-Open No. Heisei 9(1997)-110979 and Japanese Patent Application No. Heisei 8(1996)-5797). These compounds having epithio structures and compounds having epithio structures which are similar to these compounds (hereinafter, both referred to as compounds having epithio structures) show large reactivity in the presence of a curing catalyst. However, no process for mildly solidifying an unused portion of these compounds for disposal have been developed. Compositions containing a compound having episufide structures also show large reactivity in the presence of a curing catalyst. For example, when such compositions are left standing in a completely adiabatic system, abnormal polymerization takes place to generate a large amount of heat and to form bubbles and fumes. Therefore, to dispose these compounds and compositions, the compounds and the compositions cannot be left standing but must be divided into small portions and kept under control at a low temperature. Disposal in a large amount has been actually impossible. Moreover, compositions containing a compound having epithio groups contain a large amount of sulfur and there is the possibility that toxic gases such as carbon monoxide, sulfur oxide and hydrogen sulfide are generated in the abnormal polymerization. Thus, development of a process for mildly solidifying these compositions for disposal has been desired.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a process for treating for disposal an unused portion of a mixture comprising a compound having epithio structures represented by formula (1) shown below and a catalyst for curing the compound obtained in a process comprising casting and polymerizing the mixture to produce an optical material, wherein the portion of the mixture is solidified mildly for disposal.
As the result of intensive studies by the present inventors to develop the process for treating the above compound having epithio structures, it was found that the compound having epithio structures represented by formula (1) shown below can be mildly solidified when an acidic substance is added to a mixture containing the compound and a catalyst for curing the compound. The present invention was completed on the basis of this knowledge.
The present invention provides:
(1) A process for treating a compound having epithio structures for disposal which comprises adding an acidic substance to a portion for disposal of a mixture comprising the compound and a catalyst for curing the compound and solidifying the portion, the portion being obtained in a process comprising casting and polymerizing the mixture to produce an optical material and the epithio structure being represented by following formula (1):
wherein R
1
represents a hydrocarbon group having 1 to 10 carbon atoms, R
2
, R
3
and R
4
each represents hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, Y represents S or O and n represents 0 or 1;
(2) A process described in (1), wherein the acidic substance is an acidic organic compound; and
(3) A process described in (1), wherein the acidic substance is a compound having a phenolic hydroxyl group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
As the compound having epithio structures represented by formula (1) used in the present invention, compounds having two or more structures represented by formula (1) are preferable. Examples of the compound having epithio structures represented by formula (1) include the following compounds:
(A) Organic compounds having epithio groups
(B) Organic compounds having epithioalkyloxy groups
(C) Organic compounds having epithioalkylthio groups
Organic compounds (A), (B) and (C) have a chain backbone structure, an alicyclic backbone structure, an aromatic backbone structure or a heterocyclic backbone structure having nitrogen atom, oxygen atom or sulfur atom. The organic compounds may have epithio group, epithioalkyloxy groups and epithioalkylthio groups in one molecule. The organic compound may also have sulfide linkages, ether linkages, sulfone linkages, ketone linkages, ester linkages, amide linkages or urethane linkages.
Preferable examples of the organic compound having epithio groups of compound (A) include compounds obtained by replacing one or more epoxy groups in compounds having epoxy groups (not glycidyl groups) with epithio groups. Specific examples of the above compound include:
Organic compounds having a chain aliphatic backbone structure such as 1,1-bis(epithioethyl)methane, 1-(epithioethyl)-1-(&bgr;-epithiopropyl)methane, 1,1-bis(&bgr;-epithiopropyl)methane, 1-(epithioethyl)-1-(&bgr;-epithiopropyl)ethane, 1,2-bis(&bgr;-epithiopropyl)ethane, 1-(epithioethyl)-3-(&bgr;-epithiopropyl)butane, 1,3-bis(&bgr;-epithiopropyl)propane, 1-(epithioethyl)-4-(&bgr;-epithiopropyl)pentane, 1,4-bis(&bgr;-epithiopropyl)butane, 1-(epithioethyl)-5-(&bgr;-epithiopropyl)hexane, 1-(epithioethyl)-2-(&ggr;-epithiobutylthio)ethane, 1-(epithioethyl)-2-[2-(&ggr;-epithiobutylthio)ethylthio]ethane, tetrakis(&bgr;-epithiopropyl)methane, 1,1,1-tris(&bgr;-epithiopropyl)propane, 1,3-bis(&bgr;-epithiopropyl)-1-(&bgr;-epithiopropyl)-2-thiapropane and 1,5-bis(&bgr;-epithiopropyl)-2,4-bis(&bgr;-epithiopropyl)-3-thiapentane;
Organic compounds having an alicyclic backbone structure such as 1,3- and 1,4-bis(epithoethyl)cyclohexanes, 1,3- and 1,4-bis(&bgr;-epithiopropyl)cyclohexanes, bis[4-(epithioethyl)cyclohexyl]methane, bis[4-(&bgr;-epithiopropyl)cyclohexyl]methane, 2,2-bis[4-(epithioethyl)cyclohexyl]-propane, 2,2-bis[4-(&bgr;-epithiopropyl)cyclohexyl]propane, bis[4-(&bgr;-epithiopropyl)cyclohexyl]sulfide, bis[4-(epithioethyl)cyclohexyl]sulfide, 2,5-bis-(epithioethyl)-1,4-dithiane, 2,5-bis(&bgr;-epithiopropyl)-1,4-dithiane, 4-epithioethyl-1,2-cyclohexene sulfide and 4-epoxy-1,2-cyclohexene sulfide;
Organic compounds having an aromatic backbone structure such as 1,3- and 1,4-bis(epithioethyl)benzenes, 1,3- and 1,4-bis(&bgr;-epithiopropyl)-benzenes, bis[4-(epithoethyl)phenyl]methane, bis[4-(&bgr;-epithiopropyl)-phenyl]methane, 2,2-bis[4-(epithioethyl)phenyl]propane, 2,2-bis[4-(&bgr;-epithiopropyl)phenyl]propane, bis[4-(epithioethyl)phenyl]sulfide, bis[4-(&bgr;-epithiopropyl)phenyl]sulfide, bis[4-(epithioethyl)phenyl]sulfone, bis[4-(&bgr;-epithiopropyl)phenyl]sulfone, 4,4′-bis(epithioethyl)biphenyl and the like compounds and 4,4′-bis(&bgr;-epithiopropyl)biphenyl and the like compounds; and
Compounds obtained by replacing at least one hydrogen atom of the epithio group with methyl group.
Preferable examples of the organic compound having epithioalkyloxy groups of compound (B) include compounds obtained by replacing one or more glycidyl groups in epoxy compounds derived from an epihalohydrin with epithioalkyloxy groups (thioglycidyl groups). Specific examples of the above epoxy compound include epoxy compounds derived from phenols which are produced by condensation of epihalohydrins with polyhydric phenols such as hydroquinone, catechol, resorcinol, bisphenol A,
Amagai Akikazu
Takeuchi Motoharu
Frishauf, Holtz Goodman, Langer & Chick, P.C.
Mitsubishi Gas Chemical Company Inc.
Truong Duc
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