The present disclosure relates to a method for producing a thiourethane resin raw material and its application, a method for producing a polythiol composition and its application, and a polythiol composition.
Background technology
[0002]
Plastic lenses, which are lenses containing resin, are lighter than inorganic lenses, are less likely to break, and can be dyed.
For example, various studies have been made so far on lenses containing thiourethane resins (see, for example, Patent Documents 1 to 3).
[0003]
　Patent Document 1: JP-A-63-46213
　Patent Document 2: JP-A-2-270859
　Patent Document 3: JP-A-7-252207
SUMMARY OF THE INVENTION
Problems to be Solved by the Invention
[0004]
A polythiol composition and a polyisocyanate compound are usually used as raw materials for producing thiourethane resins (hereinafter also referred to as "raw materials for thiourethane resins"). Polyisocyanate compounds are produced, for example, from polyamine compounds. A polyamine compound, which is a raw material of a polyisocyanate compound, also corresponds to a thiourethane resin raw material (that is, a raw material for producing a thiourethane resin).
[0005]
A lens containing thiourethane resin (for example, an eyeglass lens) is manufactured by cutting a molded body containing thiourethane resin.
As a result, in the lens manufacturing process, a large amount of cutting powder containing thiourethane resin may be generated as waste.
In addition, in the process of manufacturing molded products containing thiourethane resin, defective molding or defective processing may occur.
Conventionally, cutting powder, molding defects, and processing defects as waste were either burned or buried as industrial waste, and were not effectively used.
However, from the viewpoint of effective use of materials (that is, recycling), a technology for manufacturing thiourethane resin raw materials is desired, using cutting powder containing thiourethane resin as waste, molding, and defective products as starting materials. The produced thiourethane resin raw material can be used as a raw material for producing a thiourethane resin.
In addition, there is a demand for a technology for manufacturing raw materials for thiourethane resins using thiourethane resins as starting materials, not limited to using thiourethane resins contained in cutting powder, moldings, and defective products as starting materials.
[0006]
The purpose of the first embodiment of the present disclosure is to provide a method for producing a thiourethane resin raw material that can produce a thiourethane resin raw material using a thiourethane resin as a starting raw material, and its application.
The purpose of the second embodiment of the present disclosure is to provide a method for producing a thiourethane resin raw material that can produce a thiourethane resin raw material using a resin mixture containing a thiourethane resin as a starting raw material, and its application.
The purpose of the third embodiment of the present disclosure is to provide a method for producing a polythiol composition that can produce a polythiol composition using a thiourethane resin as a starting material, and its application.
The purpose of the fourth embodiment of the present disclosure is to provide a method for producing a polythiol composition that can produce a polythiol composition using a thiourethane resin as a starting material, and its application.
The purpose of the fifth embodiment of the present disclosure is to provide a polythiol composition that suppresses thickening and has an excellent pot life.
Means to solve problems
[0007]
The means for solving the above problems include the following aspects.
A method for producing a thiourethane resin raw material according to the first embodiment of the present disclosure is a method for producing a thiourethane resin raw material described in <1> below.
A method for producing a thiourethane resin raw material according to the second embodiment of the present disclosure is a method for producing a thiourethane resin raw material described in <10> below.
A method for producing a polythiol composition according to the third embodiment of the present disclosure is a method for producing a polythiol composition described in <24> below.
A method for producing a polythiol composition according to the fourth embodiment of the present disclosure is a method for producing a polythiol composition described in <30> below.
The polythiol composition according to the fifth embodiment of the present disclosure is the polythiol composition described in <37> below.
There may be overlapping portions between each embodiment.
[0008]
<1> A method for producing a raw material for a thiourethane resin, including a step of reacting a thiourethane resin with an active hydrogen compound to produce a raw material for a thiourethane resin.
<2> The thiourethane resin raw material according to <1>, wherein the thiourethane resin is recovered in at least one of the eyeglass lens manufacturing process, the eyeglass manufacturing process, and the eyeglass disposal process. Production method.
<3> In the step of generating the thiourethane resin raw material, the cutting powder containing the thiourethane resin is brought into contact with the active hydrogen compound, thereby allowing the thiourethane resin and the active hydrogen compound to react. ,
The method for producing a thiourethane resin raw material according to <1> or <2>.
<4> Further, before the step of generating the thiourethane resin raw material, the cutting powder containing the thiourethane resin is classified to obtain the thiourethane resin having a smaller average particle size than the cutting powder. Including a classification step to obtain a powder containing,
In the step of generating the thiourethane resin raw material, the powder and the active hydrogen compound are brought into contact to react the thiourethane resin and the active hydrogen compound in the powder <1> or <2. > The method for producing a thiourethane resin raw material according to
<5> Furthermore, before the step of generating the thiourethane resin raw material, the cutting powder containing the thiourethane resin is sieved to obtain powder containing the thiourethane resin that has passed through the sieve. including a sieving process,
In the step of generating the thiourethane resin raw material, the powder and the active hydrogen compound are brought into contact to react the thiourethane resin and the active hydrogen compound in the powder <1> or <2. > The method for producing a thiourethane resin raw material according to
<6> The method for producing a thiourethane resin raw material according to <5>, wherein the sieve has a nominal opening defined by JIS Z-8801-1:2019 of 0.1 mm to 20 mm.
<7> Furthermore, prior to the step of generating the thiourethane resin raw material, a washing step of washing the powder containing the thiourethane resin with a hydrocarbon compound having 5 to 12 carbon atoms as a washing solvent,
In the step of generating the thiourethane resin raw material, the powder washed in the washing step and the active hydrogen compound are brought into contact with each other, so that the thiourethane resin and the active hydrogen compound in the powder The method for producing a thiourethane resin raw material according to any one of <1> to <6>, wherein the reaction is performed.
<8> The thiourethane resin raw material according to any one of <1> to <7>, wherein the thiourethane resin raw material contains at least one selected from the group consisting of a polythiol composition, a polyamine compound, and a polyisocyanate compound. A method for producing a urethane resin raw material.
<9> The method for producing a thiourethane resin raw material according to any one of <1> to <8>, wherein the active hydrogen compound is at least one selected from the group consisting of amine compounds and alcohol compounds.
[0009]
<10> In the step of generating the thiourethane resin raw material, the resin mixture containing the thiourethane resin and the active hydrogen compound are brought into contact with each other so that the thiourethane resin in the resin mixture and the active hydrogen The method for producing a thiourethane resin raw material according to any one of <1> to <9>, wherein the compound is reacted with.
<11> The thiourethane resin mixture according to <10>, wherein the resin mixture containing the thiourethane resin is recovered in at least one of the eyeglass lens manufacturing process, the eyeglass manufacturing process, and the eyeglass disposal process. A method for producing a urethane resin raw material.
<12> The method for producing a thiourethane resin raw material according to <10> or <11>, wherein the resin mixture containing the thiourethane resin contains cutting powder containing the thiourethane resin.
<13> The resin mixture containing the thiourethane resin further contains at least one selected from the group consisting of polycarbonate resins, polyallyl carbonate resins, acrylic resins, urethane resins, and episulfide resins, <10> to < 12>, the method for producing a thiourethane resin raw material according to any one of
[0010]
<14> A step of producing a polythiol composition as the thiourethane resin raw material by the method for producing a thiourethane resin raw material according to any one of <1> to <13>;
a step of mixing at least the polythiol composition and the polyisocyanate compound to obtain a polymerizable composition containing the polythiol composition and the polyisocyanate compound;
A method for producing a polymerizable composition comprising
<15> A step of producing a polymerizable composition by the method for producing a polymerizable composition according to <14>;
a step of obtaining a resin by curing the polymerizable composition;
A method for producing a resin comprising
<16> A method for manufacturing a molded body containing a resin,
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to <14>;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method for producing a molded body comprising:
<17> A method for manufacturing an optical material containing a molded body containing a resin,
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to <14>;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method for producing an optical material comprising:
<18> A method for manufacturing a lens containing a molded body containing resin,
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to <14>;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method of manufacturing a lens comprising:
<19> A polythiol composition as the thiourethane resin raw material obtained by the method for producing a thiourethane resin raw material according to any one of <1> to <13>;
with a polyisocyanate compound,
A polymerizable composition containing
<20> A resin that is a cured product of the polymerizable composition described in <19>.
<21> A molded article containing the resin described in <20>.
<22> An optical material containing the molded article according to <21>.
<23> A lens including the molded article according to <21>.
[0011]
<24> A method for producing a polythiol composition comprising a reaction step of reacting a thiourethane resin and an amine compound to produce a polythiol composition.
<25> The method for producing a polythiol composition according to <24>, wherein, in the reaction step, the thiourethane resin and the amine compound are reacted under a temperature condition of 70°C to 140°C.
<26> The amine compound is an amine compound containing at least one of an amino group and a monoalkylamino group and having a total number of amino groups and monoalkylamino groups of 1 or 2 and having a molecular weight of 300 or less <24> or <25> A method for producing the polythiol composition according to .
<27> The reaction step is a step of obtaining a reaction mixture containing the polythiol composition,
further comprising a separation step of separating the polythiol composition from the reaction mixture containing the polythiol composition,
<24> to <25> A method for producing a polythiol composition according to any one of <25>.
<28> The separation step is
obtaining a filtrate containing the polythiol composition by filtering the reaction mixture containing the polythiol composition;
acid washing the filtrate containing the polythiol composition;
separating the polythiol composition from the filtrate after the acid washing;
A method for producing a polythiol composition according to <27>.
<29> The separation step is
obtaining a filtrate containing the polythiol composition by filtering the reaction mixture containing the polythiol composition;
A water extract containing an alkali metal salt of the polythiol composition is obtained by adding a base containing an alkali metal to the filtrate containing the polythiol composition and then adding water for extraction.
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5,000 character limit. Use the arrows to translate more.obtaining
adding an acid to a water extract containing an alkali metal salt of the polythiol composition to obtain an aqueous liquid containing the polythiol composition;
obtaining an extract containing the polythiol composition by adding a hydrocarbon compound having 5 to 12 carbon atoms as an extraction solvent to the aqueous liquid containing the polythiol composition and performing extraction;
separating the polythiol composition from the extract containing the polythiol composition;
A method for producing a polythiol composition according to <27>.
[0012]
<30> A method for producing a polythiol composition comprising a reaction step of reacting a thiourethane resin and an alcohol compound in the presence of a tertiary amine compound to produce a polythiol composition.
<31> The method for producing a polythiol composition according to <30>, wherein the alcohol compound contains a compound having a boiling point of 135°C to 250°C.
<32> The method for producing a polythiol composition according to <30> or <31>, wherein, in the reaction step, the thiourethane resin and the alcohol compound are reacted under a temperature condition of 70°C to 200°C.
<33> The reaction step is a step of obtaining a reaction mixture containing the polythiol composition,
further comprising a separation step of separating the polythiol composition from the reaction mixture containing the polythiol composition,
A method for producing a polythiol composition according to any one of <30> to <32>.
<34> The separation step is
obtaining a filtrate containing the polythiol composition by filtering the reaction mixture containing the polythiol composition;
washing the filtrate containing the polythiol composition with acid and then with water;
A base containing an alkali metal is added to the filtrate containing the polythiol composition washed with water, and then water is added to perform extraction, thereby obtaining a water extract containing the alkali metal salt of the polythiol composition. to get and
adding an acid to a water extract containing an alkali metal salt of the polythiol composition to obtain an aqueous liquid containing the polythiol composition;
obtaining an extract containing the polythiol composition by adding a hydrocarbon compound having 5 to 12 carbon atoms as an extraction solvent to the aqueous liquid containing the polythiol composition and performing extraction;
separating the polythiol composition from the extract containing the polythiol composition;
A method for producing a polythiol composition according to <33>.
[0013]
<35> The polythiol composition is
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
pentaerythritol tetrakis (2-mercaptoacetate),
pentaerythritol tetrakis (3-mercaptopropionate),
2,5-dimercaptomethyl-1,4-dithiane,
bis(2-mercaptoethyl) sulfide, and
Diethylene glycol bis(3-mercaptopropionate)
The method for producing a polythiol composition according to any one of <24> to <34> containing at least one selected from the group consisting of.
<36> The method for producing a polythiol composition according to any one of <24> to <35>, which is a method for producing a polythiol composition for producing an optical material.
[0014]
<37> Containing a polythiol compound (XA) containing three or more mercapto groups as a main component,
The peak area of the compound (XB) in which at least one of the three or more mercapto groups in the polythiol compound (XA) is replaced with a group represented by the following formula (N1) by high performance liquid chromatography is is less than 0.1 with respect to 100 of the peak area of the composition,
The peak area in high performance liquid chromatography measurement of the compound (XC) in which at least one of the three or more mercapto groups in the polythiol compound (XA) is replaced with a hydroxyl group is , is less than 0.1;
Polythiol composition.
[0015]
[Chemical 1]

[0016]
In formula (N1), * represents a binding position.
The invention's effect
[0017]
According to the first embodiment of the present disclosure, a method for producing a thiourethane resin raw material and its application are provided, which can produce a thiourethane resin raw material using a thiourethane resin as a starting raw material.
According to the second embodiment of the present disclosure, a method for producing a thiourethane resin raw material and its application are provided, which can produce a thiourethane resin raw material using a resin mixture containing a thiourethane resin as a starting material.
According to the third embodiment of the present disclosure, a method for producing a polythiol composition that can produce a polythiol composition using a thiourethane resin as a starting material and its application are provided.
According to the fourth embodiment of the present disclosure, a method for producing a polythiol composition that can produce a polythiol composition using a thiourethane resin as a starting material and its application are provided.
According to the fifth embodiment of the present disclosure, a polythiol composition with suppressed thickening and excellent pot life is provided.
MODE FOR CARRYING OUT THE INVENTION
[0018]
In the present disclosure, a numerical range represented using "~" means a range including the numerical values described before and after "~" as lower and upper limits.
In the present disclosure, the term "step" includes not only independent steps, but also if the intended purpose of the step is achieved even if it cannot be clearly distinguished from other steps. .
In the present disclosure, when there are multiple substances corresponding to each component in the composition, the amount of each component contained in the composition is the total amount of the multiple substances present in the composition unless otherwise specified. means
In the numerical ranges described step by step in the present disclosure, the upper limit or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described step by step. . Moreover, in the numerical ranges described in the present disclosure, the upper or lower limits of the numerical ranges may be replaced with the values shown in the examples.
[0019]
The first to fifth embodiments of the present disclosure will be described below.
There may be overlapping portions between each embodiment. That is, one embodiment may satisfy the features of another embodiment. Therefore, preferred features of one embodiment may refer to features of other embodiments as appropriate.
[0020]
<>
[Method for producing raw material for thiourethane resin]
A method for producing a thiourethane resin raw material according to the first embodiment of the present disclosure includes a step of reacting a thiourethane resin with an active hydrogen compound to produce a thiourethane resin raw material.
[0021]
According to the manufacturing method according to the first embodiment, a thiourethane resin raw material can be manufactured using a thiourethane resin as a starting material.
The reason for such an effect is presumed as follows.
In the production method according to the first embodiment, the thiourethane resin and the active hydrogen compound react with each other, the reaction chemically decomposes the thiourethane resin, and a raw material for the thiourethane resin is obtained as a decomposition product of the thiourethane resin. it is conceivable that.
[0022]

The step of producing a thiourethane resin raw material in the manufacturing method according to the first embodiment is a step of producing a thiourethane resin raw material by reacting a thiourethane resin with an active hydrogen compound.
[0023]
(thiourethane resin)
The thiourethane resin is a starting material in this step and the manufacturing method according to the first embodiment.
The thiourethane resin is not particularly limited. Mention may be made of the thiourethane resins described.
[0024]
A thiourethane resin is usually produced as a reaction product of a polyisocyanate compound and a polythiol composition as raw materials.
For thiourethane resins, for example;
Thiourethane resin obtained from high refractive index lens materials MR-6, MR-7, MR-8, MR-8Plus, MR-60, MR-10, MR-20 (manufactured by Mitsui Chemicals, Inc.);
EYAS1.60 (manufactured by HOYA Corporation);
etc.
[0025]
The thiourethane resin is preferably recovered in at least one of the spectacle lens manufacturing process, the spectacle manufacturing process, and the spectacle disposal process. According to this aspect, it is possible to recycle the thiourethane resin, which is the material of the spectacle lenses.
here,
The manufacturing process of spectacle lenses means the process of preparing resin raw materials and performing cast polymerization to produce resin and/or the process of cutting resin moldings to obtain spectacle lenses.
The manufacturing process of eyeglasses means the process of manufacturing eyeglasses by combining eyeglass lenses and other components such as eyeglass frames.
The process of discarding eyeglasses means the process of discarding glasses that are no longer needed after being manufactured, used glasses, etc.
In any process, thiourethane resin, which is the material of eyeglass lenses, can be generated as waste.
In this embodiment, a thiourethane resin produced in at least one of these processes is used as a starting material, and this thiourethane resin is reacted with an active hydrogen compound to obtain a thiourethane resin raw material, which is a decomposition product of the thiourethane resin. get
[0026]
As described above, in the method for producing a thiourethane resin raw material of the present disclosure, including the production method according to the first embodiment, the used thiourethane resin is used for the production of the thiourethane resin raw material. As a result, it is possible to reduce the amount of thiourethane resin that is incinerated and discarded, and as a result, it is possible to reduce the generation of greenhouse gases such as carbon dioxide and air pollutants such as sulfur oxides and nitrogen oxides. In addition, since thiourea is not used in the production of the polythiol compound, there is no production of waste water containing thiourea, making the production method environmentally friendly.
To give a specific example, when 1 kg of the thiourethane resin produced in Reference Production Example 1 is incinerated, the content of carbon atoms, nitrogen atoms, and sulfur atoms in the thiourethane resin is 48.5%, 7.6% and 30.2%. When this thiourethane resin is burned, various kinds of oxides of carbon atoms, nitrogen atoms and sulfur atoms are generated as gases depending on the combustion method, but the products are carbon dioxide, nitrogen monoxide and sulfur dioxide. Then, 1.78 kg of carbon dioxide, 0.16 kg of nitrogen monoxide, and 0.6 kg of sulfur dioxide are generated when 1 kg of thiourethane resin is discarded.
The production method of the thiourethane resin raw material of the present disclosure can reduce the generation of these carbon dioxide, nitrogen monoxide, and sulfur dioxide.
[0027]
The starting material preferably contains cutting powder containing thiourethane resin.
In the step of generating the thiourethane resin raw material in this aspect, the thiourethane resin and the active hydrogen compound are reacted by bringing the cutting powder containing the thiourethane resin into contact with the active hydrogen compound.
In this aspect, since the reactivity between the active hydrogen compound and the thiourethane resin in the starting material is superior, the raw material for the thiourethane resin can be produced more effectively.
[0028]
(Active hydrogen compound)
The active hydrogen compound functions as a decomposing agent for the starting material, thiourethane resin.
From the viewpoint of the above functions, the active hydrogen compound is preferably at least one selected from the group consisting of amine compounds and alcohol compounds.
[0029]
-Amine compound-
The amine compound contains at least one of an amino group and a monoalkylamino group
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5,000 character limit. Use the arrows to translate more.Amine compounds in which the total number of amino groups and monoalkylamino groups is 1 to 6 (preferably 1 to 3, more preferably 1 or 2) are preferred.
[0030]
From the viewpoint of further improving the reactivity with the thiourethane resin, the molecular weight of the amine compound is preferably 1000 or less, more preferably 500 or less, still more preferably 300 or less, and still more preferably 200 or less. .
The lower limit of the molecular weight of the amine compound is, for example, 45 or more, preferably 59 or more, more preferably 60 or more.
[0031]
As an example of a preferable amine compound,
Examples include amine compounds containing at least one of an amino group and a monoalkylamino group and having a total number of amino groups and monoalkylamino groups of 1 or 2 and having a molecular weight of 300 or less.
[0032]
Specific examples of amine compounds include alkylamines having 2 to 10 carbon atoms, aralkylamines having 7 to 10 carbon atoms (eg, benzylamine), dialkylamines having 2 to 10 carbon atoms (eg, di-n-butylamine ), alkyldiamines having 2 to 10 carbon atoms (e.g., ethylenediamine, bis(2-aminoethyl) ether), alkyltriamines having 2 to 10 carbon atoms (e.g., bis(2-aminoethyl)amine), 2 to 10 carbon atoms, 10 hydroxyalkylamines (eg, monoethanolamine), bis(hydroxyalkyl)amines having 2 to 10 carbon atoms (eg, bis(hydroxyethyl)amine), cyclic amines having 2 to 10 carbon atoms (eg, morpholine), Secondary amines such as alkyl(hydroxyalkyl)amines having 2 to 10 carbon atoms (eg, methylethanolamine, isopropylethanolamine) and the like are included.
Benzylamine, di-n-butylamine, ethylenediamine, or monoethanolamine is preferable as the amine compound.
[0033]
-Alcohol compound-
The alcohol compound may be a monoalcohol compound containing only one hydroxy group, or a polyol compound containing two or more hydroxy groups.
[0034]
From the viewpoint of further improving the reactivity with the thiourethane resin, the molecular weight of the alcohol compound is preferably 1000 or less, more preferably 500 or less, still more preferably 300 or less, and still more preferably 200 or less. .
The lower limit of the molecular weight of the alcohol compound is, for example, 40 or more, preferably 50 or more, more preferably 60 or more.
[0035]
The alcohol compound preferably includes an alcohol compound having a boiling point of 135°C to 250°C (hereinafter also referred to as "alcohol compound A").
[0036]
In the present disclosure, the boiling point means the boiling point under 1 atmosphere (101325 Pa).
[0037]
The proportion of alcohol compound A in the total amount of alcohol compounds is preferably 50% by mass to 100% by mass, more preferably 60% by mass to 100% by mass, and still more preferably 80% by mass to 100% by mass. be.
[0038]
as an alcohol compound,
Preferably, benzyl alcohol, phenethyl alcohol, 2-octanol, 2-ethyl-1-hexanol, 1-decanol, 1-nonanol, 1-octanol, 1-heptanol, 1-hexanol, 1-pentanol, propylene glycol, or is ethylene glycol,
More preferably, benzyl alcohol, phenethyl alcohol, 1-decanol, 1-nonanol, 1-octanol, 1-heptanol, 1-hexanol, 1-pentanol, propylene glycol or ethylene glycol,
More preferred are benzyl alcohol, phenethyl alcohol, 2-octanol, 1-octanol, 1-heptanol, 1-hexanol, 1-pentanol, and propylene glycol.
[0039]
(Raw material for thiourethane resin)
The thiourethane resin raw material is the target product (more specifically, the decomposition product of the thiourethane resin that is the starting raw material) in this step and the production method according to the first embodiment, and is a raw material for producing the thiourethane resin. is.
[0040]
The thiourethane resin raw material preferably contains at least one selected from the group consisting of polythiol compositions, polyamine compounds, and diisocyanate compounds.
[0041]
-Polythiol composition-
In the present disclosure, a polythiol composition means a composition containing at least one polythiol compound.
In the present disclosure, the polythiol compound contained in the polythiol composition is also referred to as "polythiol component".
The polythiol composition may contain components other than the polythiol compound as impurities.
The polythiol composition preferably contains at least one polythiol compound as a main component.
[0042]
Here, "the polythiol composition contains at least one polythiol compound as a main component" means that the total content of at least one polythiol compound relative to the total amount of the polythiol composition is 50% or more. do.
The total content of at least one polythiol compound relative to the total amount of the polythiol composition is preferably 60% or more, more preferably 70% or more, and even more preferably 80% or more.
[0043]
Similarly, in the present disclosure, the expression that the composition “includes a certain component (hereinafter referred to as “component X”) as a main component” means the content of component X (when component X consists of two or more compounds means that the total content of two or more compounds) is 50% or more of the total amount of the composition.
The content of component X, which is the main component, is preferably 60% or more, more preferably 70% or more, and still more preferably 80% or more, relative to the total amount of the composition.
[0044]
"%" in the above explanation of the term "containing as a main component" refers to component X (e.g., at least one polythiol compound) means the ratio (area %) of the total area of all peaks.
[0045]
Examples of the polythiol composition as the target product include polythiol compositions containing known polythiol compounds.
The polythiol compound is not particularly limited as long as it contains two or more thiol groups (also known as mercapto groups).
For the polythiol compound, refer to the above-mentioned known documents (that is, JP-A-63-46213, JP-A-2-270859, JP-A-7-252207, WO 2008/047626, etc.) as appropriate. can.
[0046]
A polythiol composition as a target is
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
pentaerythritol tetrakis (2-mercaptoacetate),
pentaerythritol tetrakis (3-mercaptopropionate),
2,5-dimercaptomethyl-1,4-dithiane,
bis(2-mercaptoethyl) sulfide, and
Diethylene glycol bis(3-mercaptopropionate)
It is preferable to include at least one selected from the group consisting of (hereinafter also referred to as "polythiol component A").
The polythiol composition more preferably contains polythiol component A as a main component.
In this case, the polythiol composition may contain at least one component other than polythiol component A (eg, other polythiol compounds, components other than polythiol compounds, etc.).
[0047]
Other polythiol compounds include, for example, methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis( 3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4 -dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, etc. is mentioned.
[0048]
As a more specific embodiment of the polythiol composition as the target product,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane, and 5 ,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter collectively referred to as "polythiol component A1") as a main component;
Embodiments containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (hereinafter also referred to as "polythiol component A2") as a main component;
An embodiment containing pentaerythritol tetrakis(3-mercaptopropionate) (hereinafter also referred to as "polythiol component A3") as a main component;
Aspects containing polythiol component A1 and polythiol component A3 as main components;
Aspects containing polythiol component A2 and polythiol component A3 as main components;
etc.
The polythiol composition of each aspect may contain at least one component other than the main component (for example, other polythiol compounds, components other than polythiol compounds, etc.).
[0049]
The polythiol composition as the target product and the polythiol composition as the raw material for the thiourethane resin as the starting material need not be completely the same.
However, from the viewpoint of the performance of the thiourethane resin produced from the polythiol composition as the target product, the type of polythiol component as the main component in the polythiol composition as the target product and the main component in the polythiol composition as the raw material The type of polythiol component as a component is preferably the same. In this case, for example, an optical material B (an optical material containing a thiourethane resin) having performance comparable to that of the optical material A is obtained by using cutting powder (thiourethane resin) generated during the production of the optical material A as a raw material. can be manufactured.
[0050]
The polythiol composition as the target product may have the same polythiol component as the main component and a reduced content of impurities with respect to the polythiol composition as the raw material of the thiourethane resin as the starting material. .
In the polythiol composition as the target product, if the content of impurities is reduced, the increase in viscosity of the polythiol composition can be suppressed, and the polythiol composition can have the advantage of a long pot life.
Examples of the polythiol composition as the object in this case include, for example, the polythiol composition according to the fifth embodiment described below. Examples of the combination of the main component and impurities include the combination of the polythiol compound (XA) as the main component and the compound (XB) and the compound (XC) as impurities in the fifth embodiment described later.
[0051]
There are no particular restrictions on the use of the polythiol composition as the target product.
The polythiol composition as the target product can be used, for example, for the production of thiourethane resin.
A specific use of the polythiol composition as the target product is a polythiol composition for producing optical materials (eg, eyeglass lenses).
[0052]
-Polyamine compound-
The target polyamine compound may be any compound containing two or more amino groups.
　Polymer as a target
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5,000 character limit. Use the arrows to translate more.Amine compounds are
It preferably contains a diamine compound containing two amino groups,
pentamethylenediamine, hexamethylenediamine, m-xylylenediamine, p-xylylenediamine, isophoronediamine, bis(aminomethyl)cyclohexane, bis(aminocyclohexyl)methane, 2,5-bis(aminomethyl)bicyclo-[2 .2.1]-heptane, 2,6-bis(aminomethyl)bicyclo-[2.2.1]-heptane, tolylenediamine, 4,4′-diphenylmethanediamine and phenylenediamine It preferably contains at least one (hereinafter also referred to as "polyamine component A"),
It is more preferable to contain the polyamine component A as a main component.
[0053]
Polyamine compounds of interest include m-xylylenediamine, 2,5-bis(aminomethyl)bicyclo-[2.2.1]-heptane, and 2,6-bis(aminomethyl)bicyclo-[2. 2.1]-heptane (hereinafter also referred to as “polyamine component A1”) is further preferably included,
It is more preferable to contain polyamine component A1 as a main component.
[0054]
There are no particular restrictions on the use of the polyamine compound as the target product, and it can be applied to various uses.
A polyamine compound as a target can be used, for example, as a raw material for a polyisocyanate compound.
The produced polyisocyanate compound can be used, for example, in the production of thiourethane resins or urethane resins.
Specific uses of polyamine compounds as objects include polyamine compounds for manufacturing optical materials (for example, eyeglass lenses).
[0055]
-Polyisocyanate compound-
The target polyisocyanate compound may be any compound containing two or more isocyanate groups.
The polyisocyanate compound as the target is
It preferably contains a diisocyanate compound containing two isocyanate groups,
pentamethylene diisocyanate, hexamethylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, bis(isocyanatocyclohexyl)methane, 2,5-bis(isocyanatomethyl)bicyclo -[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate and phenylene diisocyanate It preferably contains at least one selected from (hereinafter also referred to as "polyisocyanate component A"),
It is more preferable to contain the polyisocyanate component A as a main component.
[0056]
The target polyisocyanate compounds include m-xylylene diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and 2,6-bis(isocyanatomethyl)bicyclo- [2.2.1]-It further preferably contains at least one selected from the group consisting of heptane (hereinafter also referred to as "polyisocyanate component A1"),
It is more preferable to contain the polyisocyanate component A1 as a main component.
[0057]
There are no particular restrictions on the use of the polyisocyanate compound as the target, and it can be applied to various uses.
A polyisocyanate compound as a target product can be used, for example, for producing a thiourethane resin or a urethane resin.
Specific uses of polyisocyanate compounds as objects include polyisocyanate compounds for manufacturing optical materials (for example, eyeglass lenses).
[0058]
(reaction solvent)
In the step of producing the thiourethane resin raw material, it is preferable to react the thiourethane resin and the amine compound in the presence of a reaction solvent.
Examples of the reaction solvent include hydrocarbon compounds having 5 to 12 carbon atoms (preferably 6 to 10, more preferably 7 to 9), ether compounds having 4 to 12 carbon atoms, ketone compounds having 3 to 12 carbon atoms, and 4 carbon atoms. Ester compounds having 1 to 12 carbon atoms, alcohol compounds having 2 to 12 carbon atoms, and nitrile compounds having 2 to 12 carbon atoms are preferred.
The hydrocarbon compound is preferably hexane, heptane, octane, nonane, decane, xylene, mesitylene, or toluene, more preferably heptane, octane, nonane, xylene, mesitylene, or toluene, and particularly preferably , xylene or toluene.
The ether compound is preferably diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dimethoxyethane or 1,4-dioxane, and particularly preferably dimethoxyethane.
The ketone compound is preferably acetone, methyl ethyl ketone, methyl isobutyl ketone, or 2-octanone, and particularly preferably methyl isobutyl ketone.
The above ester compound is preferably ethyl acetate, butyl acetate, or pentyl acetate, and particularly preferably pentyl acetate.
The above alcohol compound is preferably ethanol, 1-propanol, isopropanol, 1-butanol, 1-pentanol, 1-octanol, 2-octanol, benzyl alcohol, phenethyl alcohol, ethylene glycol, propylene glycol, or methyl cellosolve, Benzyl alcohol or ethylene glycol is particularly preferred.
The nitrile compound is preferably acetonitrile or propionitrile, and particularly preferably acetonitrile.
The compound used as the reaction solvent may be of only one type, or may be of two or more types.
[0059]
(Preferred embodiment of the step of generating a thiourethane resin raw material)
The step of producing a thiourethane resin raw material is preferably a step of reacting a thiourethane resin with an active hydrogen compound to produce a polythiol composition and a polyamine compound as thiourethane resin raw materials.
In such a preferred embodiment, a decomposition reaction occurs in which the thiourethane resin is decomposed into a polythiol composition and a polyamine compound by an active hydrogen compound as a decomposing agent.
When the active hydrogen compound is an amine compound, the decomposition reaction is an aminization reaction, and when the active hydrogen compound is an alcohol compound, the decomposition reaction is an alcoholysis reaction.
[0060]
(Resin mixture containing thiourethane resin)
The step of generating a thiourethane resin raw material includes bringing a resin mixture containing a thiourethane resin into contact with an active hydrogen compound, thereby reacting the thiourethane resin in the resin mixture with the active hydrogen compound to produce thiourethane. It may be a step of generating a resin raw material.
[0061]
A resin mixture containing a thiourethane resin further contains components other than the thiourethane resin.
Components other than thiourethane resins include resins other than thiourethane resins, inorganic materials for lens production (for example, glass), and the like.
[0062]
There are no particular restrictions on the resin other than the thiourethane resin.
for example;
A hybrid material of a thiourethane resin and a urethane resin, produced by adding a polyol compound to raw materials when producing a thiourethane resin;
A hybrid material of a thiourethane resin and a urea resin, produced by adding a polyamine compound to raw materials when producing a thiourethane resin;
etc. are also included in the scope of resin mixtures containing thiourethane resins and resins other than thiourethane resins.
[0063]
Also, as a resin other than thiourethane resin,
Polyolefin film that protects the surface of resin moldings for making eyeglass lenses,
A hard coat or primer coat that protects the surface of a resin molded body for making eyeglass lenses,
Abrasives used for polishing resin moldings for making eyeglass lenses,
A resin material for fixing a resin molded body when cutting a resin molded body for making eyeglass lenses,
Tape or tape glue used to fix the glass mold used when making a resin molded body for making eyeglass lenses,
etc. are also mentioned.
[0064]
The resin mixture preferably contains at least one selected from the group consisting of polycarbonate resins, polyallyl carbonate resins, acrylic resins, urethane resins, and episulfide resins, as resins other than thiourethane resins.
These resins are also resins that can be used as materials for spectacle lenses, similar to thiourethane resins.
[0065]
The resin mixture containing the thiourethane resin is preferably recovered in at least one of the eyeglass lens manufacturing process, the eyeglass manufacturing process, and the eyeglass disposal process.
The manufacturing process of eyeglass lenses, the manufacturing process of eyeglasses, and the disposal process of eyeglasses are as described above.
The resin mixture containing thiourethane resin preferably contains cutting powder containing thiourethane resin.
[0066]
(Reaction mixture containing thiourethane resin raw material)
The step of producing a thiourethane resin raw material is a step of reacting a thiourethane resin with an active hydrogen compound to produce a thiourethane resin raw material and obtaining a reaction mixture containing the thiourethane resin raw material as a target product. good too.
Components other than the thiourethane resin raw material in the reaction mixture include the reaction solvent described above, residues of raw materials (thiourethane resin and/or active hydrogen compound), impurities contained in the raw materials, and the like.
[0067]

The method for producing a thiourethane resin raw material according to the first embodiment may include a separation step of separating a thiourethane resin raw material as a target from the reaction mixture containing the thiourethane resin raw material.
The separation method in the separation process is not particularly limited, and known methods can be applied.
Separation methods in the separation process include filtration, decantation, extraction, distillation, drying (including drying under reduced pressure), and purification (eg column chromatogram). A plurality of methods may be used in combination as the separation method.
[0068]
For example, a method of separating a polythiol composition as a thiourethane resin raw material includes a method of extraction with an organic solvent or an inorganic solvent capable of dissolving the polythiol compound.
General purification methods such as column purification, distillation purification, recrystallization purification, and salt extraction are used as methods for purifying the polythiol composition.
[0069]
For example, a method for separating a polyamine compound as a raw material for a thiourethane resin includes a method of extraction with an organic solvent or an inorganic solvent capable of dissolving the polyamine compound. General purification methods such as column purification, distillation purification, recrystallization purification, and salt-forming extraction are used as purification methods for polyamine compounds.
[0070]
When the step of producing a thiourethane resin raw material is the above-described step of producing a polythiol composition and a polyamine compound as the thiourethane resin raw material, the separation step includes filtering the reaction mixture containing the polythiol composition and the polyamine derivative. and at least one of obtaining a filtrate containing the polythiol composition as a filtrate and obtaining a mixture containing a polyurea compound that is a polyamine derivative as a filtrate.
[0071]
When the separation step includes obtaining a filtrate containing a polythiol composition as a filtrate, the polythiol composition as a thiourethane resin raw material is obtained by separating the polythiol composition from the filtrate.
As an example of the separation process in this case,
obtaining a filtrate containing a polythiol composition by filtering a reaction mixture containing a polythiol composition and a polyamine compound as raw materials for a thiourethane resin;
A water extract containing an alkali metal salt of the polythiol composition is obtained by adding a base containing an alkali metal to the filtrate containing the polythiol composition and then adding water for extraction.obtaining
adding an acid to a water extract containing an alkali metal salt of a polythiol composition to obtain an aqueous liquid containing the polythiol composition;
obtaining an extract containing the polythiol composition by adding a hydrocarbon compound having 5 to 12 carbon atoms as an extraction solvent to an aqueous liquid containing the polythiol composition for extraction;
separating the polythiol composition from the extract containing the polythiol composition;
(see Example 401 below).
In this example, first, the polythiol composition in the filtrate containing the polythiol composition is converted into an alkali metal salt, and then extracted with water to obtain a water extract containing the alkali metal salt of the polythiol composition. An acid is then added here to return the alkali metal salt of the polythiol composition to the polythiol composition. The polythiol composition is extracted from the resulting aqueous liquid containing the polythiol composition with the extraction solvent to obtain an extract containing the polythiol composition. The polythiol composition is separated from the obtained extract containing the polythiol composition.
According to this example, even when the filtrate containing the polythiol composition contains many components other than the polythiol composition, a polythiol composition with a higher purity of the polythiol component as the main component can be obtained.
[0072]
In the above example, the alkali metal in the alkali metal-containing base is preferably sodium, potassium or lithium, more preferably sodium or potassium.
Bases containing alkali metals include sodium methoxide, sodium ethoxide, sodium propoxide, sodium hydroxide, potassium hydroxide, lithium hydroxide, and the like.
A base containing an alkali metal can be added to the filtrate in the form of an alcohol solution (methanol solution, ethanol solution, etc.) if necessary.
[0073]
In the above example, the acid added to the water extract containing the alkali metal salt of the polythiol composition includes hydrochloric acid, carbonic acid, nitric acid, sulfuric acid, acetic acid, formic acid, oxalic acid, and the like.
[0074]
In the above example, only one kind of extraction solvent may be used, or two or more kinds may be used.
In the separation mode B, the preferred mode of the extraction solvent is the same as the preferred mode of the reaction solvent described above.
However, the reaction solvent and the extraction solvent may be the same or different.
[0075]
When the separation step comprises obtaining a mixture comprising the polyurea compound as a filtrate or a residue from decantation or extraction, the active hydrogen compound (preferably amine compound and/or alcohol compound), the polyurea compound and the active hydrogen compound in the mixture are allowed to react, thereby producing a polyamine compound as a raw material for a thiourethane resin. By separating the polyamine compound from the reaction mixture containing the polyamine compound, a polyamine compound as a raw material for a thiourethane resin can be obtained (see Example 402 below).
[0076]

The method for producing a thiourethane resin raw material according to the first embodiment may, if necessary, include steps other than the above steps.
For other processes, for example;
A sieving step of sieving the thiourethane resin prior to the step of producing the thiourethane resin raw material;
a step of washing the thiourethane resin prior to the step of producing a thiourethane resin raw material;
Crushing and/or pulverizing the thiourethane resin prior to the step of producing the thiourethane resin raw material;
etc.
More specific examples of other processes are shown below.
[0077]
The method for producing a thiourethane resin raw material according to the first embodiment is
Before the step of generating the thiourethane resin raw material, the cutting powder containing the thiourethane resin is classified to obtain a powder containing the thiourethane resin having a smaller average particle size than the cutting powder. may include
In the step of generating the thiourethane resin raw material when this classification step is included, the powder and the active hydrogen compound are brought into contact to react the thiourethane resin in the powder and the active hydrogen compound.
For the classification process, the third embodiment or fourth embodiment described later can be referred to.
[0078]
The method for producing a thiourethane resin raw material according to the first embodiment is
Before the step of generating the thiourethane resin raw material, a sieving step of sieving the cutting powder containing the thiourethane resin to obtain a powder containing the thiourethane resin that has passed through the sieve may be included.
In the step of generating the thiourethane resin raw material when the sieving step is included, the powder and the active hydrogen compound are brought into contact to react the thiourethane resin in the powder and the active hydrogen compound.
For the sieving process, reference can be made to a third embodiment or a fourth embodiment described later.
[0079]
The nominal mesh size of the sieve specified by JIS Z-8801-1:2019 is preferably 0.1 mm to 20 mm.
[0080]
The method for producing a thiourethane resin raw material according to the first embodiment is
A washing step of washing the powder containing the thiourethane resin with a hydrocarbon compound having 5 to 12 carbon atoms as a washing solvent may be included before the step of producing the raw material for the thiourethane resin.
In the step of generating the thiourethane resin raw material when the washing step is included, the powder washed in the washing step is brought into contact with the active hydrogen compound, whereby the thiourethane resin in the powder and the above It is reacted with an active hydrogen compound.
For the sieving process, reference can be made to a third embodiment or a fourth embodiment described later.
[0081]
[Method for producing polymerizable composition]
The method for producing a polymerizable composition according to the first embodiment of the present disclosure includes
A step of producing a polythiol composition as a thiourethane resin raw material by the method for producing a thiourethane resin raw material according to the first embodiment described above;
a step of mixing at least the polythiol composition and the polyisocyanate compound to obtain a polymerizable composition containing the polythiol composition and the polyisocyanate compound;
including.
The method for producing the polymerizable composition according to the first embodiment may include other steps as necessary.
[0082]
　In the method for producing a polymerizable composition according to the first embodiment,
In the process of producing a polythiol composition, a polythiol composition is produced as a raw material for a thiourethane resin, using a thiourethane resin (for example, a thiourethane resin in grinding powder of a thiourethane resin molded body) as a starting material,
In the step of obtaining a polymerizable composition, a polymerizable composition containing the polythiol composition produced above and a polyisocyanate compound is produced.
The obtained polymerizable composition can be used again for the production of thiourethane resin.
Thus, in the method for producing a polymerizable composition according to the first embodiment, effective utilization (that is, recycling) of the materials (that is, the thiourethane resin and the polythiol composition that is its raw material) is realized.
[0083]
Further, as described above, according to the method for producing a thiourethane resin raw material according to the first embodiment, a known method (for example, a method for obtaining a polythiol composition by reacting a thiourethane resin and sodium hydroxide; a comparison described later) As compared with Example 1), a polythiol composition having a higher purity of the polythiol component as the main component is obtained.
Since such a polythiol composition is used in the method for producing a polymerizable composition according to the first embodiment, according to the polymerizable composition obtained by the method for producing a polymerizable composition according to the first embodiment, various performances A resin excellent in [for example, optical properties (eg, refractive index and/or Abbe number), heat resistance, specific gravity d, etc.] can be produced.
Therefore, the polymerizable composition obtained by the method for producing a polymerizable composition according to the first embodiment is particularly suitable as a composition for producing thiourethane resins for optical materials.
[0084]

For the process of producing the polythiol composition as the raw material for the thiourethane resin, the method for producing the polythiol composition of the present disclosure described above can be referred to as appropriate.
[0085]

In the step of obtaining a polymerizable composition, at least the polythiol composition and the polyisocyanate compound are mixed to obtain a polymerizable composition containing the polythiol composition and the polyisocyanate compound.
[0086]
The preferred embodiment of the polyisocyanate compound used in the step of obtaining the polymerizable composition is the same as the preferred embodiment of the "isocyanate compound as a raw material of the thiourethane resin" described in the "method for producing the polythiol composition" section.
[0087]
In the step of obtaining the polymerizable composition, the mixing ratio of the polythiol composition and the polyisocyanate compound is not particularly limited.
In the step of obtaining the polymerizable composition, the ratio of the charged mass of the polythiol composition to the charged mass of the polyisocyanate compound (that is, the charged mass [polythiol composition/polyisocyanate compound]) is preferably 0.10 to 10.0. , more preferably 0.20 to 5.00, still more preferably 0.50 to 1.50, still more preferably 0.70 to 1.30.
Further, the molar ratio of the mercapto group of the polythiol compound to the isocyanato group of the polyisocyanate compound contained in the polythiol composition (mercapto group/isocyanato group) is preferably 0.5 to 3.0, preferably 0.6 to 2.0. It is more preferably 0, more preferably 0.8 to 1.3.
[0088]
In the step of obtaining a polymerizable composition, the total mass of the polythiol composition and the polyisocyanate compound is not particularly limited, but is preferably 60% by mass or more based on the total amount of the polymerizable composition to be produced, It is more preferably 80% by mass or more, and still more preferably 90% by mass or more.
[0089]
In the step of obtaining the polymerizable composition, at least the polythiol composition and the polyisocyanate compound are mixed, but if necessary, the polythiol composition and the polyisocyanate compound may be mixed with other components.
In addition, in the step of obtaining the polymerizable composition, after mixing at least the polythiol composition and the polyisocyanate compound, other components may be added to the mixture.
These other components include polymerization catalysts, internal release agents, resin modifiers, chain extenders, cross-linking agents, radical scavengers, light stabilizers, UV absorbers, antioxidants, oil-soluble dyes, fillers. , adhesion improvers, antibacterial agents, antistatic agents, dyes, fluorescent whitening agents, fluorescent pigments, inorganic pigments, and the like.
[0090]
Examples of polymerization catalysts include tertiary amine compounds, inorganic or organic acid salts thereof, metal compounds, quaternary ammonium salts, organic sulfonic acids, and the like.
[0091]
An acidic phosphate ester can be used as the internal release agent. Examples of acidic phosphates include phosphate monoesters and phosphate diesters, each of which can be used alone or in combination of two or more.
[0092]
Examples of resin modifiers include episulfide compounds, alcohol compounds, amine compounds, epoxy compounds, organic acids, organic acid anhydrides, olefin compounds including (meth)acrylate compounds, and the like. Here, the (meth)acrylate compound means at least one of an acrylate compound and a methacrylate compound.
[0093]
In the step of obtaining the polymerizable composition, the above-described components can be mixed according to a conventional method, and the mixing method is not particularly limited.
[0094]
[Resin manufacturing method]
The method for manufacturing a resin according to the first embodiment of the present disclosure includes
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to the first embodiment described above;
　Curing the polymerizable compoA step of obtaining a resin by
including.
The method for manufacturing the resin according to the first embodiment may include other steps as necessary.
According to the method for producing a resin according to the first embodiment, the same effect as the method for producing a polymerizable composition according to the first embodiment described above can be obtained.
[0095]
The resin produced by the method for producing a resin according to the first embodiment and the resin according to the first embodiment described below are both thiourethane resins, but the thiourethane resin is one of the starting materials of the polythiol composition. In this disclosure, the term “resin” is simply used to distinguish from
[0096]
In the step of obtaining the resin, the resin is obtained by curing the polymerizable composition.
Curing of the polymerizable composition can be carried out by polymerizing the monomers (specifically, the polythiol composition and the polyisocyanate compound; the same shall apply hereinafter) in the polymerizable composition. As a pretreatment for polymerization, the polymerizable composition may be subjected to treatment such as filtration and degassing.
The polymerization conditions (e.g., polymerization temperature, polymerization time, etc.) for polymerizing the monomers in the polymerizable composition include the composition of the composition, the types and amounts of monomers in the composition, and the amount of polymerization catalyst in the composition. It is appropriately set in consideration of the type, amount used, and properties of the mold when using a mold described later.
Examples of the polymerization temperature include -50°C to 150°C and 10°C to 150°C.
The polymerization time includes, for example, 1 hour to 200 hours, 1 hour to 80 hours, and the like.
[0097]
In the step of obtaining the resin, the polymer obtained by polymerizing the monomer may be subjected to treatments such as annealing to obtain the resin.
Annealing temperatures include 50°C to 150°C, 90°C to 140°C, and 100°C to 130°C.
[0098]
[Method for manufacturing molded body]
A method for manufacturing a molded body according to the first embodiment of the present disclosure is a method for manufacturing a molded body containing resin,
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to the first embodiment described above;
a step of obtaining a resin-containing molding by curing the polymerizable composition;
including.
The manufacturing method of the molded article of the present disclosure may include other steps as necessary.
According to the method for producing a molded article according to the first embodiment, the same effect as the method for producing a polymerizable composition according to the first embodiment described above can be obtained.
[0099]
In the step of obtaining a resin-containing molded article, a resin-containing molded article is obtained by curing the polymerizable composition.
For preferable conditions for curing the polymerizable composition, that is, for polymerization of the monomers in the polymerizable composition, the section "Resin production method" can be referred to as appropriate.
[0100]
An example of polymerization in this process is casting polymerization.
In casting polymerization, first, the polymerizable composition is injected between molding molds held by gaskets, tapes, or the like. At this time, if necessary, defoaming treatment, filtration treatment, or the like may be performed.
Next, by polymerizing the monomer in the polymerizable composition injected between the molding molds, the composition is cured between the molding molds to obtain a cured product. Next, the cured product is removed from the molding mold to obtain a molded body containing the resin.
The polymerization of the above monomers may be carried out by heating the polymerizable composition. This heating can be performed, for example, by using a heating device having a mechanism for heating the object to be heated in an oven, in water, or the like.
[0101]
[Method for producing optical material, method for producing lens]
A method for manufacturing an optical material (for example, a lens) according to the first embodiment of the present disclosure is a method for manufacturing an optical material (for example, a lens) including a molded body containing resin,
A step of producing a polymerizable composition by the method for producing a polymerizable composition according to the first embodiment described above;
a step of obtaining a resin-containing molding by curing the polymerizable composition;
including.
The method of manufacturing an optical material (for example, a lens; the same shall apply hereinafter) of the present disclosure may include other steps as necessary.
According to the method for producing an optical material according to the first embodiment, the same effect as the method for producing a polymerizable composition according to the first embodiment described above can be obtained.

WE CLAIMS

[Claim 1]
A method for producing a raw material for thiourethane resin, including a step of reacting a thiourethane resin with an active hydrogen compound to produce a raw material for thiourethane resin.
[Claim 2]
The method for producing a thiourethane resin raw material according to claim 1, wherein the thiourethane resin is recovered in at least one of the eyeglass lens manufacturing process, the eyeglass manufacturing process, and the eyeglass disposal process.
[Claim 3]
In the step of generating the thiourethane resin raw material, the cutting powder containing the thiourethane resin is brought into contact with the active hydrogen compound, thereby allowing the thiourethane resin and the active hydrogen compound to react.
The method for producing a thiourethane resin raw material according to claim 1 or 2.
[Claim 4]
Furthermore, by classifying the cutting powder containing the thiourethane resin before the step of generating the thiourethane resin raw material, the powder containing the thiourethane resin having a smaller average particle size than the cutting powder including a classification step to obtain
In the step of generating the thiourethane resin raw material, the thiourethane resin in the powder and the active hydrogen compound are reacted by contacting the powder and the active hydrogen compound. 2. The method for producing a thiourethane resin raw material according to 2 above.
[Claim 5]
Furthermore, before the step of generating the thiourethane resin raw material, a sieving step of sieving the cutting powder containing the thiourethane resin to obtain a powder containing the thiourethane resin that has passed through the sieve. including
In the step of generating the thiourethane resin raw material, the thiourethane resin in the powder and the active hydrogen compound are reacted by contacting the powder and the active hydrogen compound. 2. The method for producing a thiourethane resin raw material according to 2 above.
[Claim 6]
The method for producing a thiourethane resin raw material according to claim 5, wherein the sieve has a nominal opening defined by JIS Z-8801-1:2019 of 0.1 mm to 20 mm.
[Claim 7]
Furthermore, prior to the step of generating the thiourethane resin raw material, a washing step of washing the powder containing the thiourethane resin with a hydrocarbon compound having 5 to 12 carbon atoms as a washing solvent,
In the step of generating the thiourethane resin raw material, the powder washed in the washing step and the active hydrogen compound are brought into contact with each other, so that the thiourethane resin and the active hydrogen compound in the powder The method for producing a thiourethane resin raw material according to any one of claims 1 to 6, wherein the reaction is performed.
[Claim 8]
The thiourethane resin raw material according to any one of claims 1 to 7, wherein the thiourethane resin raw material contains at least one selected from the group consisting of a polythiol composition, a polyamine compound, and a polyisocyanate compound. manufacturing method.
[Claim 9]
The method for producing a thiourethane resin raw material according to any one of claims 1 to 8, wherein the active hydrogen compound is at least one selected from the group consisting of amine compounds and alcohol compounds.
[Claim 10]
The step of generating the thiourethane resin raw material includes bringing the resin mixture containing the thiourethane resin into contact with the active hydrogen compound, so that the thiourethane resin in the resin mixture, the active hydrogen compound, The method for producing a thiourethane resin raw material according to any one of claims 1 to 9, wherein the reaction is performed.
[Claim 11]
The thiourethane resin raw material according to claim 10, wherein the resin mixture containing the thiourethane resin is recovered in at least one of the eyeglass lens manufacturing process, the eyeglass manufacturing process, and the eyeglass disposal process. manufacturing method.
[Claim 12]
The method for producing a thiourethane resin raw material according to claim 10 or 11, wherein the resin mixture containing the thiourethane resin contains cutting powder containing the thiourethane resin.
[Claim 13]
The resin mixture containing the thiourethane resin further contains at least one selected from the group consisting of polycarbonate resins, polyallyl carbonate resins, acrylic resins, urethane resins, and episulfide resins. A method for producing a thiourethane resin raw material according to any one of the above items.
[Claim 14]
a step of producing a polythiol composition as the thiourethane resin raw material by the method for producing a thiourethane resin raw material according to any one of claims 1 to 13;
a step of mixing at least the polythiol composition and the polyisocyanate compound to obtain a polymerizable composition containing the polythiol composition and the polyisocyanate compound;
A method for producing a polymerizable composition comprising
[Claim 15]
a step of producing a polymerizable composition by the method for producing a polymerizable composition according to claim 14;
a step of obtaining a resin by curing the polymerizable composition;
A method for producing a resin comprising
[Claim 16]
A method for manufacturing a molded body containing resin,
a step of producing a polymerizable composition by the method for producing a polymerizable composition according to claim 14;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method for producing a molded body comprising:
[Claim 17]
A method for manufacturing an optical material containing a molded body containing resin,
a step of producing a polymerizable composition by the method for producing a polymerizable composition according to claim 14;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method for producing an optical material comprising:
[Claim 18]
A method for manufacturing a lens containing a molded body containing resin,
a step of producing a polymerizable composition by the method for producing a polymerizable composition according to claim 14;
a step of obtaining a molded article containing a resin by curing the polymerizable composition;
A method of manufacturing a lens comprising:
[Claim 19]
a polythiol composition as the thiourethane resin raw material, obtained by the method for producing a thiourethane resin raw material according to any one of claims 1 to 13;
with a polyisocyanate compound,
A polymerizable composition containing
[Claim 20]
A resin that is a cured product of the polymerizable composition according to claim 19.
[Claim 21]
A molded body containing the resin according to claim 20.
[Claim 22]
An optical material containing the molded article according to claim 21.
[Claim 23]
A lens comprising the molded article according to claim 21.
[Claim 24]
A method for producing a polythiol composition, which includes a reaction step of reacting a thiourethane resin and an amine compound to produce a polythiol composition.
[Claim 25]
The method for producing a polythiol composition according to claim 24, wherein in the reaction step, the thiourethane resin and the amine compound are reacted under a temperature condition of 70°C to 140°C.
[Claim 26]
26. The amine compound according to claim 24 or 25, wherein the amine compound contains at least one of an amino group and a monoalkylamino group and the total number of amino groups and monoalkylamino groups is 1 or 2 and has a molecular weight of 300 or less. A method for producing a polythiol composition.
[Claim 27]
the reaction step is a step of obtaining a reaction mixture containing the polythiol composition,
further comprising a separation step of separating the polythiol composition from the reaction mixture containing the polythiol composition,
A method for producing a polythiol composition according to any one of claims 24 to 25.
[Claim 28]
The separation process is
obtaining a filtrate containing the polythiol composition by filtering the reaction mixture containing the polythiol composition;
acid washing the filtrate containing the polythiol composition;
separating the polythiol composition from the filtrate after the acid washing;
The method for producing a polythiol composition according to claim 27, comprising
[Claim 29]
The separation process is
obtaining a filtrate containing the polythiol composition by filtering the reaction mixture containing the polythiol composition;
A base containing an alkali metal is added to the filtrate containing the polythiol composition, and then water is added for extraction to obtain a water extract containing the alkali metal salt of the polythiol composition;
adding an acid to a water extract containing an alkali metal salt of the polythiol composition to obtain an aqueous liquid containing the polythiol composition;
obtaining an extract containing the polythiol composition by adding a hydrocarbon compound having 5 to 12 carbon atoms as an extraction solvent to the aqueous liquid containing the polythiol composition and performing extraction;
separating the polythiol composition from the extract containing the polythiol composition;
The method for producing a polythiol composition according to claim 27, comprising
[Claim 30]
A method for producing a polythiol composition, comprising a reaction step of reacting a thiourethane resin and an alcohol compound in the presence of a tertiary amine compound to produce a polythiol composition.
[Claim 31]
The method for producing a polythiol composition according to claim 30, wherein the alcohol compound contains a compound having a boiling point of 135°C to 250°C.
[Claim 32]
The method for producing a polythiol composition according to claim 30 or 31, wherein in the reaction step, the thiourethane resin and the alcohol compound are reacted under a temperature condition of 70°C to 200°C.
[Claim 33]
the reaction step is a step of obtaining a reaction mixture containing the polythiol composition,
further comprising a separation step of separating the polythiol composition from the reaction mixture containing the polythiol composition,
A method for producing a polythiol composition according to any one of claims 30 to 32.
[Claim 34]
The separation process is
The polythiol compositionobtaining a filtrate comprising the polythiol composition by filtering the reaction mixture comprising
washing the filtrate containing the polythiol composition with acid and then with water;
A base containing an alkali metal is added to the filtrate containing the polythiol composition washed with water, and then water is added to perform extraction, thereby obtaining a water extract containing the alkali metal salt of the polythiol composition. to get and
adding an acid to a water extract containing an alkali metal salt of the polythiol composition to obtain an aqueous liquid containing the polythiol composition;
obtaining an extract containing the polythiol composition by adding a hydrocarbon compound having 5 to 12 carbon atoms as an extraction solvent to the aqueous liquid containing the polythiol composition and performing extraction;
separating the polythiol composition from the extract containing the polythiol composition;
The method for producing a polythiol composition according to claim 33, comprising
[Claim 35]
The polythiol composition is
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiundecane,
pentaerythritol tetrakis (2-mercaptoacetate),
pentaerythritol tetrakis (3-mercaptopropionate),
2,5-dimercaptomethyl-1,4-dithiane,
bis(2-mercaptoethyl) sulfide, and
Diethylene glycol bis(3-mercaptopropionate)
The method for producing a polythiol composition according to any one of claims 24 to 34, comprising at least one selected from the group consisting of.
[Claim 36]
The method for producing a polythiol composition according to any one of claims 24 to 35, which is a method for producing a polythiol composition for producing an optical material.
[Claim 37]
contains a polythiol compound (XA) containing 3 or more mercapto groups as the main component,
The peak area of the compound (XB) in which at least one of the three or more mercapto groups in the polythiol compound (XA) is replaced with a group represented by the following formula (N1) by high performance liquid chromatography is is less than 0.1 with respect to 100 of the peak area of the composition,
The peak area in high performance liquid chromatography measurement of the compound (XC) in which at least one of the three or more mercapto groups in the polythiol compound (XA) is replaced with a hydroxyl group is , is less than 0.1;
Polythiol composition.