JP5423943B2 - Cleaning agent and cleaning method for composition containing sulfur and selenium atoms - Google Patents

Description

  The present invention relates to a cleaning agent and a cleaning method for a composition for an optical material obtained by using an inorganic compound having a sulfur atom and / or a selenium atom, which is a raw material of an optical material having a high refractive index and Abbe number. This composition for optical materials is useful for optical products such as plastic lenses, prisms, optical fibers, information recording substrates, filters, and adhesives, especially for plastic lenses for spectacles.

  In recent years, plastic materials have been widely used in various optical materials, particularly eyeglass lenses, because they are light and tough and easy to dye. The main performance most required for optical materials, particularly spectacle lenses, is a high refractive index, and the lens becomes thinner as the refractive index increases. In recent years, optical materials using inorganic compounds having sulfur atoms and / or selenium atoms for the purpose of increasing the refractive index have been reported (Patent Documents 1 to 3). However, a specific organic sulfur compound is used from the viewpoint of solubility when cleaning the devices used for the preparation of these optical material compositions. For example, bis (2-mercaptoethyl) sulfide and 1,2-ethanedithiol have a strong odor and thus have a poor working environment. Further, in order to treat exhaust gas, it is necessary to provide a special exhaust device such as an alkali scrubber. . Furthermore, it is necessary to ensure the stability of the waste liquid after washing, and so far no cleaning agent has been clarified in consideration of the safety of the waste liquid. When the stability of the waste liquid is poor, precipitates are generated during storage, and general waste liquid treatment may not be possible.

Japanese Patent No. 3738817 JP 2002-82203 A JP 2002-122701 A

  Detergent and cleaning method with good cleaning properties and high stability of waste liquid after cleaning for a composition for optical materials using an inorganic compound having a sulfur atom and / or selenium atom capable of increasing the refractive index I will provide a.

  As a result of intensive studies to solve the problems of the present invention, the present inventor, when washing a composition for optical materials containing an inorganic compound having a sulfur atom and / or selenium atom, (A) a compound having a lactam and (B) The present inventors have found a cleaning agent and a cleaning method for an optical material composition characterized by containing a cyclic ether compound, and have solved the problem.

That is, the present invention is as follows.
1. A detergent for cleaning composition for optical materials containing sulfur, N- alkylpyrrolidones (hereinafter, (A) compound) and 5- or 6-membered ring cyclic ether compound (hereinafter, (B) Compound) And (A) the compound is 20 to 50% by weight, and (B) the compound is 50 to 80% by weight .
2. (A) The cleaning agent for an optical material composition according to item 1, wherein the compound is at least one selected from N-methylpyrrolidone, N-ethylpyrrolidone, and N-propylpyrrolidone.
3. (B) The cleaning agent for an optical material composition according to item 1 or 2, wherein the compound is one or more selected from tetrahydrofuran, dioxane and furan.
4). (A) Compound is N-methylpyrrolidone, (B) Compound is 1 or more types chosen from tetrahydrofuran, dioxane, and furan, The cleaning agent of the composition for optical materials of Claim 1 characterized by the above-mentioned.
5). A cleaning method for cleaning an optical material composition containing sulfur with the cleaning agent according to any one of claims 1 to 4.
6). A cleaning method for cleaning equipment used for preparing a composition for optical material containing sulfur with the cleaning agent according to Item 4.

  When cleaning a composition for an optical material containing an inorganic compound having a sulfur atom and / or a selenium atom, by using a cleaning agent that uses (A) a lactam-containing compound and (B) a cyclic ether compound, The composition for materials can be washed and removed, and the waste liquid after washing has high stability, and general waste liquid treatment becomes possible.

  The compound having (A) lactam used in the present invention is a compound having a bond formed by dehydration condensation of a carboxyl group and an amino group and forming a ring. Among various lactams, a lactam having 3 to 8 carbon atoms is preferable, a γ-lactam is more preferable, and an -alkylpyrrolidone is particularly preferable. Particularly preferred specific examples are N-methylpyrrolidone, N-ethylpyrrolidone and N-propylpyrrolidone, and the most preferred specific example is N-methylpyrrolidone. These lactams may be used alone or in combination of two or more.

    Preferred as the (B) cyclic ether compound used in the present invention is a compound having 2 to 18 carbon atoms, and includes a monocyclic or polycyclic compound and alkyl-substituted products thereof. Specific examples include ethylene oxide, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, dioxane, trioxane, furan, pyran, benzofuran, isobenzofuran, 1-benzopyran, 2-isobenzopyran, and a mixture of two or more. May be used. Among these, a 5-membered ring or a 6-membered ring compound is preferable in terms of safety and ease of drying. Particularly preferred specific examples are tetrahydrofuran, dioxane and furan, and the most preferred specific example is tetrahydrofuran.

  The proportion of the compound (A) having a lactam and (B) the cyclic ether compound is preferably 5 to 95% by weight for the (A) compound and 5 to 95% by weight for the (B) compound. More preferably, the ratio of the compound (A) is 10 to 90% by weight and the compound (B) is 1 to 90% by weight, and more preferably the compound (A) is 15 to 70% by weight, and the compound (B) is 30%. It is a ratio of -85 weight%. Particularly preferred is a ratio of 20 to 50% by weight of the compound (A) and 50 to 80% by weight of the compound (B).

  In the present invention, a mixture of (A) a lactam-containing compound and (B) a cyclic ether compound is used as a cleaning agent. However, a surfactant, an antioxidant, and an ultraviolet absorber as long as the object of the present invention is not impaired. It is also possible to add known additives such as a rust inhibitor and a diluent.

  The composition for an optical material containing an inorganic compound having a sulfur atom and / or selenium atom to be cleaned in the present invention comprises 1 to 50 parts by weight of an inorganic compound having a sulfur atom and / or selenium atom, and reacts with the inorganic compound. It is a composition containing 50 to 99 parts by weight of a possible compound and, if necessary, other known compounds such as a catalyst, an ultraviolet absorber, an antioxidant, a dye, and a release agent. Examples of inorganic compounds having a sulfur atom and / or selenium atom include sulfur, carbon disulfide, phosphorus sulfide, selenium sulfide, metal sulfide and metal hydrosulfide, selenium, carbon diselenide, phosphorus selenide, metal selenide More preferred are sulfur, carbon disulfide and selenium sulfide, and particularly preferred is sulfur. These inorganic compounds having a sulfur atom and a selenium atom may be used alone or in combination of two or more. The compound capable of reacting with an inorganic compound having a sulfur atom and / or selenium atom is not particularly limited as long as it can become a resin by polymerization and curing, but has a sulfur atom and / or selenium atom. One or more organic compounds selected from organic compounds are preferred for making the optical material obtained by polymerization and curing have a higher refractive index. Specifically, mercaptans, sulfides, polysulfides, thioketones, thioisocyanates, thiolsulfinates, thiolsulfonates, sulfilimines and derivatives thereof, sulfonium salts, sulfonium ylides, sulfones , Sulfoximines and derivatives thereof, sulfinic acids and derivatives thereof, sulfonic acids and derivatives thereof, preferably mercaptans, sulfides, polysulfides, and more preferably episulfides in sulfides. A more preferred specific example is a compound having a structure represented by the following formula (1):

CH ₂ CH ₂
/ \ / \
_{S-CH- (CH 2) a} - [S b - (CH 2) c -S d] e - (CH 2) f -CH-S (1)
(Wherein, a, b, c, d, e and f each independently represent an integer of 0 to 3)
Particularly preferred are bis (β-epithiopropyl) sulfide and bis (β-epithiopropyl) disulfide.

  In the method for cleaning an optical material composition containing an inorganic compound having a sulfur atom and / or a selenium atom, the apparatus used for the preparation of the composition for optical material is composed of (A) a compound having a lactam and (B) a ring. A mixture of ether compounds is used with a cleaning agent. The method of contacting with the composition for optical materials is, for example, spraying a cleaning agent on the device, soaking it in a sponge or waste cloth, wiping it, filling the device with the cleaning agent, immersing the device in the cleaning agent, etc. Not limited. If necessary, simultaneous stirring, vibration, ultrasonic irradiation, air bubbling, etc. may be used. The temperature at the time of washing may be room temperature, under heating, or under cooling.

  EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

The solubility of the composition was evaluated as follows.
A: Completely dissolved and the cleaning agent became transparent B: Almost dissolved but the cleaning agent became turbid C: Dissolved little but could not be dissolved D: Not dissolved at all

The stability of the waste liquid after washing was visually observed after being allowed to stand at 30 ° C. for 1, 7, and 30 days.
A: Waste liquid is transparent B: Slightly opaque C: Clearly opaque but no sediment D: Clearly opaque and sediment

Example of preparation of composition for optical material Preparation of composition for optical material containing inorganic compound having sulfur atom and / or selenium atom 50 g of sulfur and 450 g of bis (thioglycidyl) sulfide were mixed and stirred at 30 ° C. in a 500 ml glass flask. . After about 3 hours, a uniform composition was obtained.

Example 1
After removing most of the composition from the glass flask used in the preparation of the optical material composition described in the preparation example of the optical material composition, N-methylpyrrolidone (NMP) 5 wt% and tetrahydrofuran as a cleaning agent A cleaning solution consisting of 95% by weight of (THF) was sprayed. The composition was completely dissolved and the cleaning agent became clear, and the flask could be cleaned cleanly. When the waste solution of the cleaning agent in which the composition was dissolved was stored at 30 ° C., it was transparent for 7 days. The results are shown in Table 1.

Examples 2-11, Comparative Examples 1-4
The same operation as in Example 1 was repeated except that the cleaning agent shown in Table 1 was used. The results are shown in Table 1.

Claims (6)

A detergent for cleaning composition for optical materials containing sulfur, N- alkylpyrrolidones (hereinafter, (A) compound) and 5- or 6-membered ring cyclic ether compound (hereinafter, (B) Compound) A cleaning agent for an optical material composition, wherein the compound (A) is 20 to 50% by weight, and the compound (B) is 50 to 80% by weight . The cleaning agent for a composition for optical materials according to claim 1, wherein the compound (A) is at least one selected from N-methylpyrrolidone, N-ethylpyrrolidone and N-propylpyrrolidone. The cleaning agent for a composition for optical materials according to claim 1 or 2, wherein the compound (B) is at least one selected from tetrahydrofuran, dioxane and furan. The cleaning agent for an optical material composition according to claim 1, wherein the compound (A) is N-methylpyrrolidone, and the compound (B) is at least one selected from tetrahydrofuran, dioxane and furan. A cleaning method for cleaning a composition for optical material containing sulfur with the cleaning agent according to claim 1. The washing | cleaning method which wash | cleans the apparatuses with which the cleaning agent of Claim 4 was used for preparation of the composition for optical materials containing sulfur.