CN104203526A - Method for producing plastic lens - Google Patents
Method for producing plastic lens Download PDFInfo
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- CN104203526A CN104203526A CN201380016414.7A CN201380016414A CN104203526A CN 104203526 A CN104203526 A CN 104203526A CN 201380016414 A CN201380016414 A CN 201380016414A CN 104203526 A CN104203526 A CN 104203526A
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- China
- Prior art keywords
- polymerization
- plastic lens
- polymeric compositions
- hours
- epithio propyl
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2011/00—Optical elements, e.g. lenses, prisms
- B29L2011/0016—Lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Abstract
Provided is a method for producing a urethane-based plastic lens, wherein striae are not easily generated even by short-time polymerization. A method for producing a plastic lens, wherein a polymerization composition, which contains (A) a polyisocyanate compound, (B) a compound having a plurality of mercapto groups or hydroxy groups in each molecule and (C) a polymerization catalyst and which satisfies the conditions (1) and (2) described below, is polymerized under such polymerization conditions that the initial temperature is 20 DEG C or less and the polymerization time is 12 hours or less. (1) The viscosity at 10 DEG C right after the blending is 200 mPa.s or less. (2) The viscosity at 10 DEG C after 8 hours under certain conditions is 400 mPa.s or more but 100 Pa.s or less.
Description
Technical field
The present invention relates to a kind of manufacture method of plastic lens, particularly relate to the manufacture method of a kind of polyurethane or thiocarbamates glasses plastic lens.
Background technology
Compared with inorganic lenses, the lightweight and difficult fragmentation of plastic lens, can dye, and is therefore used as the optical element such as eyeglass, camera lens.As the material of plastic lens, because polyurethanes resin refractive index is high and lightweight, resistance to impact is excellent, therefore conventionally use the polyurethanes resin (patent documentation 1) being formed by the polymer of polyisocyanates and multi-thioalcohol compound.These plastic lens are for example injected into the composition before polymerization in the shaping mould with glass mold and pad, heat up at leisure, carry out for a long time polymerization to amount to about 24 hours.
In the manufacture method of plastic lens, according to the volume of the lens that will manufacture and want intensity, the character of the lens that obtain, produce texture and become sometimes problem, in polyurethanes plastic lens, propose to carry out pre-reaction, the object (patent documentation 2) of such texture will be heated up the technology of the productivity ratio that improves plastic lens, can realize thus to prevent after the viscosity tackify of monomer composition.
In addition, in patent documentation 3, as thering is practical productivity ratio, and can obtain the manufacture method without the thicker plastic lens of optical distortion and texture etc., a kind of manufacture method has been proposed, the method possesses following operation: after polymerizable composition, polymerizable composition is filled in mould, and maintenance operation more than initial temperature when polymerizable composition, polymerizable composition is remained on to filling; And above-mentioned polymerizable composition, polymerizable composition is carried out to cooling refrigerating work procedure.In polymerization process, although slow at starting stage polymerization speed, sharply accelerate in certain stage, therefore, the object of the method is to prevent the unfavorable conditions such as the distortion causing because of this speed rising.
Prior art document
Patent documentation
Patent documentation 1: No. 3279784th, Japan Patent
Patent documentation 2: TOHKEMY 2007-90574 communique
Patent documentation 3: TOHKEMY 2009-226742 communique
Summary of the invention
The problem that invention will solve
In the manufacture method of plastic lens, need the plenty of time for by polymeric compositions polymerization, for example, in the method for patent documentation 2, with regard to concrete embodiment, the heating schedule arranging about approximately 20～40 hours carries out polymerization.In addition, in the method for patent documentation 3, with regard to concrete embodiment, utilize the heating schedule about approximately 17～30 hours to carry out polymerization.Consider from the viewpoint such as productivity ratio, reduction furnace equipment expense of plastic lens, preferably manufacture plastic lens with shorter polymerization time, but there are the following problems: if shorten the just easy unfavorable conditions such as texture that produce of polymerization time.
Therefore, problem of the present invention is, a kind of manufacture method of polyurethanes plastic lens is provided, even if it is with short time polymerization, is also difficult for producing thus texture bad.
The method of dealing with problems
The inventor has carried out concentrated research to the initial viscosity of composition and its polymerization property, found that, meets the polymeric compositions of specified conditions by use, even be also difficult for producing thus texture with short time polymerization, thereby has completed the present invention.
, the invention provides following [1]～[5].
[1] manufacture method for plastic lens, it comprises:
Make polymeric compositions in initial temperature below 20 DEG C, carry out polymerization under the polymerizing condition of polymerization time below 12 hours, wherein,
Described polymeric compositions contains: (A) in polyisocyanate compound, (B) a part, there is the compound of multiple sulfydryls or hydroxyl and (C) polymerization catalyst,
And described polymeric compositions meets following condition (1) and (2):
(1) the described polymeric compositions after just allotment is below 200mPas the viscosity of 10 DEG C,
(2) under 10 DEG C of controlled conditions, the viscosity of the described polymeric compositions after 8 hours is more than 400mPas and below 100Pas.
[2] manufacture method of the plastic lens described in above-mentioned [1], wherein, described polymerization catalyst is the organo-metallic compound shown in following general formula (I),
(R)
n-Sn-(X)
4-n (I)
[in formula (I), R represents the alkyl of carbon number 1 to 12, and X represents fluorine atom, chlorine atom or bromine atoms, and n is 1 to 3 integer].
[3] manufacture method of the described plastic lens in above-mentioned [1] or [2], wherein, in described polymerizing condition, final temperature is 100～150 DEG C, and the ratio of the time of polymerization is 60～90% to make it below 60 DEG C.
[4] manufacture method of the plastic lens of any one in above-mentioned [1]～[3], wherein, polymerization time is below 10 hours.
[5] manufacture method of the plastic lens of any one in above-mentioned [1]～[4], wherein, polymerization time is below 5 hours.
The effect of invention
According to the manufacture method of plastic lens of the present invention, even if provide a kind of with short time polymerization, the manufacture method of the bad also less plastic lens of texture.
Detailed description of the invention
The manufacture method of plastic lens of the present invention comprise make polymeric compositions in initial temperature below 20 DEG C, polymerization under the polymerizing condition of polymerization time below 12 hours, described polymeric compositions contains: (A) in polyisocyanate compound, (B) a part, have the compound of multiple sulfydryls or hydroxyl and (C) polymerization catalyst, and, described polymeric compositions meets following condition (1) and (2)
(1) the described polymeric compositions after just allotment is below 200mPas the viscosity of 10 DEG C,
(2) under 10 DEG C of controlled conditions, the viscosity of the described polymeric compositions after 8 hours is more than 400mPas and below 100Pas.
Meet the polymeric compositions of above-mentioned condition by use, even if polymerization is to complete with the short time, produces the bad plastic lens of texture and also can tail off.
The reason that can obtain such effect is also uncertain, but it has been generally acknowledged that its reason is as follows.
Think by using the polymeric compositions of the demonstration particular viscosity performance as the polymeric compositions of use in the present invention, can prevent the convection current (thermal convection current) of the Temperature Distribution of polymeric compositions based in die cavity, even if therefore, by short time polymerization, its texture is bad also can tail off.
Think the heat producing in the die cavity at mould in the time manufacturing that texture when plastic lens is bad to result from polymeric compositions polymerization, particularly because polymerization time is shorter, the heat that time per unit produces increases, therefore the Temperature Distribution in die cavity expands, and it is bad that result just can produce texture in a large number.
About such thermal convection current, there is the dimensionless number as fluid thermal transmission index that is known as Rayleigh number shown in following mathematical expression (a).
Ra＝[gβ△Td
3]/[νX]
Ra: Rayleigh number
G: acceleration of gravity
β: the coefficient of cubical expansion
△ T: temperature difference
D
3: 3 powers of distance between the upper and lower
ν: dynamic viscosity coefficient
X: thermal diffusion coefficient
That is, according to above-mentioned formula, in the situation that temperature difference is larger, when distance is large between the upper and lower, Rayleigh number becomes large, shows and easily causes convection current, and when viscosity is large, Rayleigh number diminishes, and shows and is difficult for causing convection current.
If consider the polymerization of the lens of definite shape herein, acceleration of gravity is constant, and the distance between the upper and lower that is equivalent to lens wall thickness is also constant.In addition, can think that the coefficient of cubical expansion, thermal diffusion coefficient are intrinsic value according to the degree of polymerization of monomer, in addition, less to the contribution of Rayleigh number.Therefore,, in the polymerization of lens, dynamic viscosity coefficient ν and temperature difference △ T are larger on Rayleigh number impact.
About condition (1), at the polymerization initial stage, in low-temperature region because the heat release that polymerization causes is few, the tendency that exists △ T value to diminish.Therefore,, as shown in condition (1), even if viscosity is low, dynamic viscosity coefficient ν value is little, Rayleigh number is also suppressed must be lower, is therefore difficult for causing thermal convection current.
About condition (2), many because of the heat release that polymerization causes in the polymerization later stage, exist △ T value to become large tendency.Therefore, as shown in condition (2), by using viscosity rise fast polymeric compositions, become the large polymerization later stage obtain sufficiently high dynamic viscosity coefficient ν at △ T, result can suppress lowlyer by Rayleigh number, is therefore difficult for causing thermal convection current.
Therefore can think, polymeric compositions that can the application of the invention, even the polymerization of short time is provided, the manufacture method of the bad also less plastic lens of texture.
Below formation of the present invention is elaborated.
[polymeric compositions]
For polymeric compositions of the present invention, after (1) its just allotment, be below 200mPas the viscosity of 10 DEG C.Be the polymeric compositions below 200mPas by using the viscosity after described allotment, polymerization initial temperature be set as below uniform temperature simultaneously, can prevent initial thermal convection current, the texture that therefore can significantly reduce plastic lens is bad.
In addition, the viscosity in condition (1) is preferably below 150mPas, more preferably below 100mPas.The lower limit of the viscosity in condition (1) is not particularly limited, for example, be 10mPas.
Just the viscosity after allotment refers to composition is mixed, and the viscosity of measuring in 10 minutes.
In addition, in the present invention, viscosity is to use the vibrating type viscometer VISCOMATE processed VM-10A of SEKONIC company, the value of measuring according to JIS Z8803 standard at 10 DEG C.
(2) under 10 DEG C of controlled conditions, the viscosity of the described polymeric compositions after 8 hours is more than 400mPas and below 100Pas.
Satisfy condition (1) and the polymeric compositions of the range of viscosities of condition (2) by use, can significantly reduce texture bad.
More than viscosity in condition (2) is preferably 500mPas and below 50Pas, more preferably more than 700mPas and below 3Pas.
It should be noted that, the viscosity in condition (2) is also the value of measuring according to the method identical with condition (1), at 10 DEG C.
For polymeric compositions used in the present invention, based on the general knowledge of this area, the addition of polymerization catalyst that can be by regulating the monomer component character that use and adapt with the polymerization property of monomer component obtains the polymeric compositions that meets above-mentioned condition (1) and (2).Particularly the content of the polymerization catalyst in polymeric compositions easily exerts an influence to the physical property of condition (2).Below each composition and the content of polymeric compositions used in the present invention are described.
The polymeric compositions using in the present invention contains and in (A) polyisocyanate compound (being designated hereinafter simply as " (A) composition "), (B) a part, has the compound (being designated hereinafter simply as " (B) composition ") of multiple sulfydryls or hydroxyl and (C) polymerization catalyst (being designated hereinafter simply as " (C) composition ").
< (A) polyisocyanate compound >
As polyisocyanate compound, be not particularly limited, for example can enumerate: xyxylene vulcabond (1,3-bis-(isocyanates ylmethyl) benzene), durol dimethyl vulcabond, 3,3 '-dichloro diphenyl-4,4 '-vulcabond, 4,4 '-methyl diphenylene diisocyanate, hexamethylene diisocyanate, 2,2 ', 5,5 '-Tetrachlorodiphenyl-4,4 '-vulcabond, toluene di-isocyanate(TDI), two (isocyanates ylmethyl) cyclohexane, two (4-NCO cyclohexyl) methane, two (4-NCO methylcyclohexyl) methane, cyclohexane diisocyanate, IPDI, two (isocyanates ylmethyl) dicyclo [2.2.2] octanes, two (isocyanates ylmethyl) dicyclo [2.2.1] heptane, 2-isocyanates ylmethyl-3-(3-NCO propyl group)-5-NCO methyl bicycle [2.2.1] heptane, 2-isocyanates ylmethyl-3-(3-isocyanates propyl group)-6-NCO methyl bicycle [2.2.1] heptane, 2-isocyanates ylmethyl-2-[3-NCO propyl group]-5-NCO methyl bicycle [2.2.1] heptane, 2-isocyanates ylmethyl-2-(3-NCO propyl group)-6-NCO methyl bicycle [2.2.1] heptane, 2-isocyanates ylmethyl-3-(3-NCO propyl group)-6-(2-NCO ethyl) dicyclo [2.2.1] heptane, 2-isocyanates ylmethyl-3-(3-NCO propyl group)-6-(2-NCO ethyl) dicyclo [2.2.1] heptane, 2-isocyanates ylmethyl-2-(3-NCO propyl group)-5-(2-NCO ethyl) dicyclo [2.2.1] heptane, 2-isocyanates ylmethyl-2-(3-NCO propyl group)-6-(2-NCO ethyl) dicyclo [2.2.1] heptane etc.Particularly preferably xyxylene vulcabond, durol dimethyl vulcabond, two (isocyanates ylmethyl) dicyclo [2.2.1] heptane and two (isocyanates ylmethyl) cyclohexane.Above-claimed cpd can be used alone or in combination of two or more kinds.
The content of polyisocyanate compound is preferably 0.6～1.4 with respect to (B) composition in polymeric compositions by equivalent proportion, and more preferably 0.8～1.2, more preferably 0.9～1.1.Here said equivalent proportion refers to the molal quantity of NCO of (A) composition and the ratio of (B) sulfydryl of composition and the total mole number of hydroxyl [(A)/(B)].
The content of polyisocyanate compound is not particularly limited, and is preferably 30～60 quality % with respect to polymeric compositions total amount, more preferably 35～55 quality %, more preferably 40～50 quality %.
In < (B) a part, there is the compound > of multiple sulfydryls or hydroxyl
As the compound in (B) a part with multiple sulfydryls or hydroxyl, the mercaptan compound that can enumerate following multi-thioalcohol compound, polyol compound, contains hydroxyl.It should be noted that, the compound in so-called a part with multiple sulfydryls or hydroxyl comprises the compound in a part with multiple sulfydryls and hydroxyl.
As multi-thioalcohol compound, for example can enumerate: dimercapto methane, 1,1-dimercaptoethane, 1,2-dimercaptoethane, 1,1-dimercaptopropane, 1,2-dimercaptopropane, 1,3-dimercaptopropane, 2,2-dimercaptopropane, 1,1-dimercapto butane, 1,2-dimercapto butane, 1,3-dimercapto butane, Isosorbide-5-Nitrae-dimercapto butane, 2,2-dimercapto butane, 2,3-dimercapto butane, 1,2-thioresorcin, 1,3-thioresorcin, Isosorbide-5-Nitrae-thioresorcin, 1,2-dimercapto dimethylbenzene, 1,3-dimercapto dimethylbenzene, Isosorbide-5-Nitrae-dimercapto dimethylbenzene, two mercapto methyl-Isosorbide-5-Nitrae-the dithiane of 2,5-and polymer thereof, two mercapto methyl-1 of 4,5-, 3-dithiane and polymer thereof, 2,5-dimercapto-Isosorbide-5-Nitrae-dithiane, 4,5-dimercapto-1,3-dithiane, two mercapto methyl-1 of 4,5-, 3-dithiolane, 4,5-dimercapto-1, two mercaptan compounds such as 3-dithiolane, 2,3-bis-(2-sulfydryl ethylmercapto group)-1-propane mercaptan, two mercapto methyl-3,6,9-, tri-sulfo--1,11-hendecane two mercaptan, four mercapto methyl methane, pentaerythrite four mercaptopropionic acid esters, pentaerythrite four mercaptoacetates etc. or its mixture.
As polyol compound, for example can enumerate: ethylene glycol, diethylene glycol, propane diols, DPG, butanediol, neopentyl glycol, glycerine, trimethylolethane, trimethylolpropane, butane triol, 1,2-methyl glucoside, pentaerythrite, dipentaerythritol, tripentaerythritol, D-sorbite, erythrite, threitol, ribitol, arabite, xylitol, allitol, mannitol, cholesterine (dorcitol), iditol, glycol, inositol, hexanetriol, triglycerin, two glycerine, triethylene glycol, polyethylene glycol, three (2-hydroxyethyl) chlorinated isocyanurates, cyclobutane glycol, pentamethylene glycol, cyclohexane diol, cycloheptane glycol, cyclooctane glycol, cyclohexanedimethanol, hydroxypropyl cyclohexanol, three ring [5,2,1,0,2,6] decane dimethanols, two ring [4,3,0] nonane glycol, bicyclohexane glycol, three ring [5,3,1,1] dodecanediols, two ring [4,3,0] nonane dimethanols, three ring [5,3,1,1] dodecane diethanol, hydroxypropyl three encircles [5,3,1,1] dodecanol, spiral shell [3,4] octane glycol, butyl cyclohexane glycol, 1,1 '-bis-cyclohexylidene glycol, phloroglucitol, maltitol, the aliphatic polyols such as lactitol, dihydroxy naphthlene, trihydroxynaphthalene, tetrahydroxy naphthalene, dihydroxy benzenes, benzene triol, biphenyl tetrol, pyrogallol, (hydroxyl naphthyl) pyrogallol, trihydroxy phenanthrene, bisphenol-A, Bisphenol F, benzene dimethanol, the aromatic polyols such as tetrabromobisphenol A, two (2-hydroxyethyl) thioether, two (the 2-hydroxyethyl sulfydryl) ethane of 1,2-, two (2-hydroxyethyl) disulfide, Isosorbide-5-Nitrae-dithiane-2,5-glycol, two (2,3-dihydroxypropyl) thioether, four (4-hydroxyl-2-sulphur butyl) methane, two (4-hydroxy phenyl) sulfone (trade name bisphenol S), tetrabromo-bisphenol s, tetramethyl bisphenol S, 4,4 '-thiobis (the 6-tert-butyl group-3-methylphenol), the polyalcohol that two (the 2-hydroxyethyl sulphur ethyl) cyclohexanes etc. of 1,3-contain sulphur atom etc.
In addition, as the mercaptan compound that contains hydroxyl, for example can enumerate: 2 mercapto ethanol, 2,3-dimercapto-1-propyl alcohol, 3-hydroxyl-2-butane mercaptan, 3-sulfydryl hexanol, 3-sulfydryl-2-methyl butanol, 3-sulfydryl-3-methyl butanol, 3-sulfydryl-2-methyl anyl alcohol etc.
Above-claimed cpd can be used singly or in combination two or more.
< (C) polymerization catalyst >
As polymerization catalyst, be not particularly limited, can enumerate amines, organo-metallic compound etc.
As amines, for example can enumerate: triethylenediamine, hexa, N, N-dimethyl octylame, N, N, N ', N '-tetramethyl-1,6-diamino hexane, 4,4 '-trimethylene two (1-methyl piperidine), 1,8-diazabicylo (5,4,0)-7-endecatylene.
As organo-metallic compound, can enumerate organotin, copper oleate, acetylacetone copper, ferric acetyl acetonade, iron naphthenate, ferric lactate, ironic citrate, iron gluconate, metatitanic acid 2-Octyl Nitrite etc.
As polymerization catalyst, wherein preferred organotin, the organo-metallic compound shown in preferred following general formula (1).
(R)
n-Sn-(X)
4-n (1)
[in formula (1), R represents the alkyl of carbon number 1 to 12 (preferably 4 to 8), and X represents that fluorine atom, chlorine atom or bromine atoms (preferably chlorine atom), n are 1 to 3 integer (being preferably 2).]
As above-mentioned concrete example, can enumerate dimethyltin chloride, dibutyl tin dichloride, dioctyl stannous chloride, dimethyl tin bibromide, dibutyl tin bibromide, dioctyl tin bibromide, dioctyl tin bifluoride etc.These catalyst may be used singly or in combination of two or more.
In these polymer, preferably dimethyltin chloride, dibutyl tin dichloride.
The content of polymer can suitably be set as basis taking the technology general knowledge of this area according to the polymerization property of polymeric compositions, with respect to polymeric compositions total amount, be preferably 0.001～2.0 quality %, more preferably 0.005～1.5 quality %, more preferably 0.01～1.0 quality %.
In addition, in polymeric compositions of the present invention, also can contain episulfide compounds.As episulfide compounds, for example can enumerate: two (β-epithio propyl group) thioether, two (β-epithio propyl dithiocarbamate) methane, two (β-epithio propyl dithiocarbamate) ethane of 1,2-, two (β-epithio propyl dithiocarbamate) propane of 1,3-, two (β-epithio propyl dithiocarbamate) propane of 1,2-, 1-(β-epithio propyl dithiocarbamate)-2-(β-epithio propyl dithiocarbamate methyl) propane, Isosorbide-5-Nitrae-bis-(β-epithio propyl dithiocarbamate) butane, two (β-epithio propyl dithiocarbamate) butane of 1,3-, 1-(β-epithio propyl dithiocarbamate)-3-(β-epithio propyl dithiocarbamate methyl) butane, two (β-epithio propyl dithiocarbamate) pentanes of 1,5-, 1-(β-epithio propyl dithiocarbamate)-4-(β-epithio propyl dithiocarbamate methyl) pentane, two (β-epithio propyl dithiocarbamate) hexanes of 1,6-, 1-(β-epithio propyl dithiocarbamate)-5-(β-epithio propyl dithiocarbamate methyl) hexane, 1-(β-epithio propyl dithiocarbamate)-2-[(2-β-epithio propyl dithiocarbamate ethyl) sulfo-] ethane, 1-(β-epithio propyl dithiocarbamate)-2-{[2-(2-β-epithio propyl dithiocarbamate ethyl) thio-ethyl] sulfo-} chain compound such as ethane, four-(β-epithio propyl dithiocarbamate methyl) methane, 1, 1, 1-tri-(β-epithio propyl dithiocarbamate methyl) propane, 1, two (β-epithio propyl dithiocarbamate)-2-(β-epithio propyl dithiocarbamate methyl)-3-thia pentanes of 5-, 1, two (β-epithio propyl dithiocarbamates)-2 of 5-, two (β-epithio propyl dithiocarbamate methyl)-3-thia pentanes of 4-, 1-(β-epithio propyl dithiocarbamate)-2, two (β-epithio propyl dithiocarbamate methyl)-4-thia hexanes of 2-, 1, 5, 6-tri-(β-epithio propyl dithiocarbamate)-4-(β-epithio propyl dithiocarbamate methyl)-3-thia hexane, 1, two (β-epithio propyl dithiocarbamate)-4-(β-epithio propyl dithiocarbamate methyl)-3 of 8-, 6-dithia octane, 1, two (β-epithio propyl dithiocarbamates)-4 of 8-, two (β-epithio propyl dithiocarbamate methyl)-3 of 5-, 6-dithia octane, 1, two (β-epithio propyl dithiocarbamates)-4 of 8-, two (β-epithio propyl dithiocarbamate methyl)-3 of 4-, 6-dithia octane, 1, two (β-epithio propyl dithiocarbamates)-2 of 8-, 4, 5-tri-(β-epithio propyl dithiocarbamate methyl)-3, 6-dithia octane, 1, two (β-epithio propyl dithiocarbamates)-2 of 8-, two (β-epithio propyl dithiocarbamate methyl)-3 of 5-, 6-dithia octane, 1, two (β-epithio propyl dithiocarbamate)-5-(β-epithio propyl dithiocarbamate methyl)-5-[(2-β-epithio propyl dithiocarbamate ethyls of 9-) sulphomethyl]-3, 7-dithia nonane, 1, two (β-epithio propyl dithiocarbamates)-5 of 10-, two [(2-β-epithio propyl dithiocarbamate ethyl) sulfo-s]-3 of 6-, 6, 9-tri-thia decane, 1, two (β-epithio propyl dithiocarbamates)-4 of 11-, two (β-epithio propyl dithiocarbamate methyl)-3 of 8-, 6, 9-tri-thia hendecanes, 1, two (β-epithio propyl dithiocarbamates)-5 of 11-, two (β-epithio propyl dithiocarbamate methyl)-3 of 7-, 6, 9-tri-thia hendecanes, 1, two (β-epithio propyl dithiocarbamates)-5 of 11-, 7-[(2-β-epithio propyl dithiocarbamate ethyl) sulphomethyl]-3, 6, 9-tri-thia hendecanes, 1, two (β-epithio propyl dithiocarbamates)-4 of 11-, two (β-epithio propyl dithiocarbamate methyl)-3 of 7-, 6, a chain compound such as 9-tri-thia hendecanes, 1,3-and 1, two (β-epithio propyl dithiocarbamate) cyclohexanes, 1 of 4-, 3-and 1, two (β-epithio propyl dithiocarbamate methyl) cyclohexanes of 4-, two [4-(β-epithio propyl dithiocarbamate) cyclohexyl] methane, 2, two [4-(β-epithio propyl dithiocarbamate) cyclohexyl] propane of 2-, two [4-(β-epithio propyl dithiocarbamate) cyclohexyl] sulfide, 2, two (β-epithio propyl dithiocarbamate methyl)-1 of 5-, 4-dithiane, 2, two (β-epithio propyl dithiocarbamate ethylmercapto group methyl)-ester ring type compounds such as Isosorbide-5-Nitrae-dithiane of 5-, 1, two (β-epithio propyl dithiocarbamate) benzene and 1 of 3-, two (β-epithio propyl dithiocarbamate) benzene, 1 of 4-, two (β-epithio propyl dithiocarbamate methyl) benzene and 1 of 3-, two (β-epithio propyl dithiocarbamate methyl) benzene of 4-, two [4-(β-epithio propyl dithiocarbamate) phenyl] methane, 2, two [4-(β-epithio propyl dithiocarbamate) phenyl] propane of 2-, two [4-(β-epithio propyl dithiocarbamate) phenyl] thioether, two [4-(β-epithio propyl dithiocarbamate) phenyl] sulfone, 4, the aromatic compounds such as 4 '-bis-(β-epithio propyl dithiocarbamate) biphenyl, and the compound that formed by methyl substituted of at least 1 hydrogen of the epithio base of these compounds etc.Particularly preferably two (β-epithio propyl group) thioethers.These compounds can be used alone or in combination of two or more kinds.
In order easily to peel off with mold from lens moulding after polymerization, polymeric compositions of the present invention also can contain releasing agent.
As releasing agent, preferably use phosphate, particularly, can enumerate the phosphate monoesters such as acidic isopropyl phosphate, acid butyl phosphate, acid octyl phosphate, acid phosphoric acid ester in the ninth of the ten Heavenly Stems, acid phosphoric acid ester in the last of the ten Heavenly stems, acid phosphoric acid isodecyl ester, acid phosphoric acid 13 esters, acid phosphoric acid stearyl ester, acid phosphoric acid propyl group phenylester, acid phosphoric acid butyl phenyl ester, acid phosphoric acid butoxy ethyl ester; The di-phosphate esters such as acid diisopropyl phosphate, dibutyl acid phosphate, acid dioctylphosphoric acid ester, acid di(2-ethylhexyl)phosphate isodecyl ester, two (acid phosphoric acid 13 esters), acid di(2-ethylhexyl)phosphate stearyl ester, acid di(2-ethylhexyl)phosphate propyl group phenylester, acid di(2-ethylhexyl)phosphate butyl phenyl ester, acid di(2-ethylhexyl)phosphate butoxy ethyl ester etc.These releasing agents can be used singly or in combination two or more.
The content of releasing agent is preferably 0.001～0.5 % by weight with respect to polymeric compositions total amount.
As other any composition of polymeric compositions, also can contain such as blueing agent, ultra-violet absorber etc.
As blueing agent, can enumerate dyestuff or the pigment of blue system and red system.The content of blueing agent is not particularly limited, and is preferably 0.00002～0.0002 quality % with respect to polymeric compositions total amount.
As ultra-violet absorber, for example can enumerate: 2,4-dihydroxy benaophenonel, ESCALOL 567, BP-4, UV-531,2-hydroxyl-4-positive 12-alkoxy benzophenone, 2-hydroxyl-4-benzyloxy benzophenone, 2, the benzophenone compounds such as 2 '-dihydroxy-4-methoxy benzophenone, 2-(2 '-hydroxyl-5 '-aminomethyl phenyl) BTA, 2-(2 '-hydroxyl-3 ', 5 '-bis--tert-butyl-phenyl)-5-chlorobenzotriazole, 2-(2 '-hydroxyl-3 '-tert-butyl group-5 '-aminomethyl phenyl)-5-chlorobenzotriazole, 2-(2 '-hydroxyl-3 ', 5 '-bis--tertiary pentyl phenyl) BTA, 2-(2 '-hydroxyl-3 ', 5 '-bis--tert-butyl-phenyl) BTA, 2-(2 '-hydroxyl-5 '-tert-butyl-phenyl) BTA, 2-(2 '-hydroxyl-5 '-tertiary octyl phenyl) BTA, the benzotriazole cpds such as 2-(2 '-hydroxyl-4 '-octyloxyphenyl) BTA, dibenzoyl methane, Eusolex 9020 etc.These ultra-violet absorbers can be used singly or in combination two or more.The content of ultra-violet absorber also depends on ultraviolet radiation absorption energy and maximum absorption wavelength, but with respect to the total amount of polymeric compositions, is preferably 0.03～3 quality %.
[manufacture method]
The manufacture method of plastic lens of the present invention is in initial temperature below 20 DEG C, under the polymerizing condition of polymerization time below 12 hours, makes above-mentioned polymeric compositions polymerization obtain plastic lens.
Polymerization is that above-mentioned polymeric compositions is injected to lens moulding mold, and polymerization is carried out in heating.
Lens moulding is preferably used the existing known mold being made up of pad and mould with mold.As the material of pad, can enumerate the fluororesin such as tetrafluoroethene.As the material of mould, generally use glass.
The temperature conditions of polymerization preferably carries out the scope of 0～150 DEG C.In addition, as the temperature conditions of polymerization, initial temperature is below 20 DEG C, more preferably 0～15 DEG C, and more preferably 0～10 DEG C.Final temperature is not particularly limited, but for example preferably 100～150 DEG C, and more preferably 110～140 DEG C, further preferably 120～130 DEG C.These temperature conditions are considered art technology general knowledge, according to the rheological parameters' change with time of polymeric compositions viscosity, set heating schedule and be warming up to final temperature under the condition that does not produce thermal convection current.
Make below the ratio of the time of its polymerization be not particularly limited at 60 DEG C, but in the case of in the low state of polymeric compositions viscosity, from compared with lowland keep temperature, prevent thermal convection current viewpoint consider, be preferably 60～90% with respect to the total polymerization time, more preferably 65～85%, more preferably 70～80%.Particularly in the manufacture method of plastic lens of the present invention, due to the satisfy condition polymeric compositions of (2) of use, even if therefore under above-mentioned cryogenic conditions, polymerization also can high viscosity, therefore in the heating schedule later stage, even with short time intensification, plastic lens is also difficult for producing texture.
Polymerization time is below 12 hours, considers from the viewpoint of productivity ratio, is preferably below 10 hours, more preferably below 5 hours.The lower limit of polymerization time is not particularly limited, but is more than 3 hours.Can set above-mentioned heating schedule according to these polymerization times.
By manufacture method of the present invention, can manufacture pellicle mirror and finishing lenses.Wherein, if manufacturing the lens weight of cutting as before the processing such as eyeglass frame shape is lens more than 20g and has certain thickness lens, due to a large amount of polymeric compositions of needs, based on easily causing that thermal convection current etc. is former thereby easily producing texture, but the polymeric compositions using in the application of the invention, can reduce the generation of texture.
Embodiment
, by embodiment, the present invention is described in further detail below, but the present invention is not limited to these embodiment.It should be noted that, the glasses that obtain in embodiment and comparative example carry out as follows with the evaluation of physical property of plastic lens.
(1) viscosity (mPas (10 DEG C))
Use the vibrating type viscometer VISCOMATE processed VM-10A of SEKONIC company, measure at 10 DEG C.It should be noted that, assay method is according to JIS Z8803 standard.
(2) have or not texture
Use USHIO motor (strain) appearance inspection device Optical processed Modulex SX-UI251HQ to carry out projection check.
The high pressure UV lamp of light source uses USH-102D, in the distance of 1m, white screen is set, and tested lens are inserted between light source and screen, and whether qualified determine according to the projected image on screen.
The lens that there is no irregular wire on projected image are defined as to certified products, the lens that have irregular wire are defined as to defective products.
(embodiment 1～10, comparative example 1～4)
Polymeric compositions shown in following table 1 is poured into a mould, then lens moulding with mold in, in table, under the Elevated Temperature Conditions of the polymerization procedure of record, carry out polymerizing curable, manufactured plastic lens.
* 1 finishing lenses: diameter 70mm, the lens number of degrees-6.00 diopter, center wall thickness 1.0mm, the thick 9.0mm in edge
* 2 pellicle mirrors: diameter 70mm, lens base arc 136mm (radius of curvature R), center wall thickness 4.0mm, the thick 8.0mm in edge
(polymerization procedure)
P1: 10 DEG C of initial temperatures, be warming up to 40 DEG C through 3.5 hours, be then warming up to 125 DEG C with 0.5 hour, and then keep 1 hour (totally 5 hours, 60 DEG C following approximately 4 hours) at 125 DEG C.
P2: keep 5.0 hours 7.5 DEG C of initial temperatures, be then warming up to 55 DEG C through 3.0 hours, thereafter, be warming up to 125 DEG C with 1.0 hours, and then keep 1 hour (totally 10 hours, 60 DEG C approximately 8 hours below) at 125 DEG C.
P3: keep 5.0 hours 15 DEG C of initial temperatures, be warming up to 55 DEG C through 3.0 hours after it, thereafter, be warming up to 125 DEG C with 1.0 hours, and then keep 1 hour (totally 10 hours, 60 DEG C approximately 8 hours below) at 125 DEG C.
P4: keep 5.0 hours 25 DEG C of initial temperatures, be warming up to 55 DEG C through 3.0 hours after it, thereafter, be warming up to 125 DEG C with 1.0 hours, and then keep 1 hour (totally 10 hours, 60 DEG C approximately 8 hours below) at 125 DEG C.
P5: keep 4.0 hours 13 DEG C of initial temperatures, be warming up to 80 DEG C through 4.0 hours after it, thereafter, be warming up to 125 DEG C with 0.5 hour, and then keep 1 hour (totally 9.5 hours, 60 DEG C approximately 7 hours below) at 125 DEG C.
From above result, satisfy condition in use the polymeric compositions of (1) and (2), even utilize in the situation of manufacturing plastic lens for 12 hours with interior polymerization procedure, by making its polymerization under the condition below 20 DEG C in initial temperature, be difficult for producing texture bad.
industrial applicibility
According to the present invention, owing to manufacturing the bad less plastic lens of texture with short polymerization time, therefore can improve plastic lens productivity ratio, and then can reduce furnace equipment expense.
Claims (5)
1. a manufacture method for plastic lens, it comprises:
Make polymeric compositions in initial temperature below 20 DEG C, carry out polymerization under the polymerizing condition of polymerization time below 12 hours, wherein,
Described polymeric compositions contains: (A) in polyisocyanate compound, (B) a part, there is the compound of multiple sulfydryls or hydroxyl and (C) polymerization catalyst,
And described polymeric compositions meets following condition (1) and (2):
(1) the described polymeric compositions after just allotment is below 200mPas the viscosity of 10 DEG C,
(2) under 10 DEG C of controlled conditions, the viscosity of the described polymeric compositions after 8 hours is more than 400mPas and below 100Pas.
2. the manufacture method of plastic lens as claimed in claim 1, wherein, described polymerization catalyst is the organo-metallic compound shown in following general formula (I),
(R)
n-Sn-(X)
4-n (I)
In formula (I), R represents the alkyl of carbon number 1 to 12, and X represents fluorine atom, chlorine atom or bromine atoms, and n is 1 to 3 integer.
3. the manufacture method of plastic lens as claimed in claim 1 or 2, wherein, in described polymerizing condition, final temperature is 100～150 DEG C, and the ratio of the time of polymerization is 60～90% to make it below 60 DEG C.
4. the manufacture method of the plastic lens as described in any one in claim 1～3, wherein, in described polymerizing condition, polymerization time is below 10 hours.
5. the manufacture method of the plastic lens as described in any one in claim 1～4, wherein, in described polymerizing condition, polymerization time is below 5 hours.
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| JP2012072547 | 2012-03-27 | ||
| JP2012-072547 | 2012-03-27 | ||
| PCT/JP2013/057869 WO2013146481A1 (en) | 2012-03-27 | 2013-03-19 | Method for producing plastic lens |
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| CN104203526A true CN104203526A (en) | 2014-12-10 |
| CN104203526B CN104203526B (en) | 2016-11-09 |
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| JP (1) | JP6095646B2 (en) |
| CN (1) | CN104203526B (en) |
| WO (1) | WO2013146481A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293865A (en) * | 2017-10-18 | 2019-02-01 | Skc株式会社 | Polymerisable compound for glass lens |
| CN112313565A (en) * | 2018-06-28 | 2021-02-02 | 豪雅镜片泰国有限公司 | Polymerizable composition for optical member |
| CN113631613A (en) * | 2019-03-28 | 2021-11-09 | 豪雅镜片泰国有限公司 | Polymerizable composition for optical member, and spectacle lens |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20190079956A (en) * | 2017-12-28 | 2019-07-08 | 에스케이씨 주식회사 | Polymerizable composition for optical material |
| KR102003056B1 (en) * | 2018-01-12 | 2019-07-23 | 에스케이씨 주식회사 | Plastic tinted lenses and manufacturing method thereof |
| KR102150592B1 (en) * | 2019-09-11 | 2020-09-01 | 에스케이씨 주식회사 | Polymerizable composition for optical material |
| CN115286758A (en) | 2020-01-27 | 2022-11-04 | 三井化学株式会社 | Polymerizable composition for optical material, polymerizable prepolymer composition for optical material, cured product, and method for producing optical material |
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| JP4214870B2 (en) * | 2003-09-10 | 2009-01-28 | セイコーエプソン株式会社 | Method for manufacturing optical article |
| JP2009226742A (en) * | 2008-03-24 | 2009-10-08 | Seiko Epson Corp | Manufacturing method of plastic lens |
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- 2013-03-19 JP JP2014507759A patent/JP6095646B2/en active Active
- 2013-03-19 WO PCT/JP2013/057869 patent/WO2013146481A1/en active Application Filing
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| CN1035520A (en) * | 1988-02-17 | 1989-09-13 | 三井东圧化学株式会社 | Based on the resin for making lens of urethane, contain the manufacture method of plastic lens and this kind lens of this kind resin |
| US5744568A (en) * | 1993-09-29 | 1998-04-28 | Hoya Corporation | Process for the production of polyurethane lens |
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| CN109293865A (en) * | 2017-10-18 | 2019-02-01 | Skc株式会社 | Polymerisable compound for glass lens |
| CN112313565A (en) * | 2018-06-28 | 2021-02-02 | 豪雅镜片泰国有限公司 | Polymerizable composition for optical member |
| CN112313565B (en) * | 2018-06-28 | 2022-11-29 | 豪雅镜片泰国有限公司 | Polymerizable composition for optical member |
| CN113631613A (en) * | 2019-03-28 | 2021-11-09 | 豪雅镜片泰国有限公司 | Polymerizable composition for optical member, and spectacle lens |
Also Published As
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| WO2013146481A1 (en) | 2013-10-03 |
| JPWO2013146481A1 (en) | 2015-12-10 |
| CN104203526B (en) | 2016-11-09 |
| JP6095646B2 (en) | 2017-03-15 |
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