[go: up one dir, main page]

WO2019112255A1 - Lentille en hydrogel de silicone ayant d'excellentes propriétés physiques - Google Patents

Lentille en hydrogel de silicone ayant d'excellentes propriétés physiques Download PDF

Info

Publication number
WO2019112255A1
WO2019112255A1 PCT/KR2018/015076 KR2018015076W WO2019112255A1 WO 2019112255 A1 WO2019112255 A1 WO 2019112255A1 KR 2018015076 W KR2018015076 W KR 2018015076W WO 2019112255 A1 WO2019112255 A1 WO 2019112255A1
Authority
WO
WIPO (PCT)
Prior art keywords
independently
alkyl
ppm
silicone hydrogel
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2018/015076
Other languages
English (en)
Korean (ko)
Inventor
신동훈
현상일
오경희
이승호
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Interojo Inc
Original Assignee
Interojo Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180150615A external-priority patent/KR102715262B1/ko
Application filed by Interojo Inc filed Critical Interojo Inc
Publication of WO2019112255A1 publication Critical patent/WO2019112255A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04—Contact lenses for the eyes

Definitions

  • the present invention relates to a silicone hydrogel lens having excellent physical properties.
  • Contact lenses need to be in contact with the eye to maintain eye safety and efficacy while maintaining the transparency and wettability of the contact lens, so oxygen must be properly supplied from the atmosphere and the release of carbon dioxide from the cornea It should be appropriate.
  • the contact lens should be designed in consideration of the clinical aspects in which the flow of the tear layer should be smooth and excessive friction between the eyelid and the eye surface should be avoided.
  • Patent Document 1 provides a method of improving the fit of a contact lens by increasing the hydrophilic property by plasma-treating the surface of an initial first generation silicone hydrogel contact lens.
  • An object of the present invention is to provide a silicone hydrogel lens having excellent physical properties, which is produced from a polymer composition containing a siloxane macromonomer to which a specific functional group is introduced, and has a high oxygen permeability and a high moisture content and a comfortable fit for a long time.
  • the present invention provides a silicone hydrogel lens that satisfies excellent physical properties, particularly high oxygen permeability and low surface contact angle
  • the silicone hydrogel lens of the present invention is a silicone hydrogel lens comprising a main chain, a side chain of siloxane macromonomer, A polysiloxane macromonomer into which a glyceryl repeating unit is introduced, and may satisfy a surface contact angle measured by an oxygen permeability of 80 barrer or more and a trapped bubble method of 40 deg. Or less.
  • the siloxane macromonomer may be a main chain, a side chain, or a halo (C 1 -C 10 ) alkyl group.
  • the silicone hydrogel lens may have a water content of 55 to 70% and a modulus of 0.3 to 0.9 MPa.
  • the silicone hydrogel lens may satisfy a surface contact angle measured by an oxygen permeability of 100 barrer or more and a trapped bubble method of 35 degrees or less.
  • the siloxane macromonomer may be a monomer represented by the following formula (1).
  • R 1 to R 4 are independently of each other hydrogen or (C 1 -C 10 ) alkyl
  • R a1 to R a12 independently from each other are hydrogen, hydroxy or (C 1 -C 10 ) alkyl;
  • o and a are each independently an integer selected from 1 to 10;
  • p, q, b and c are each independently an integer selected from 0 to 10;
  • D 1 and D 2 are independently of each other a single bond, -NHCOO-, -NHCONH-, -OCONH-R S -NHCOO-, -NHCONH-R t -NHCONH- and -OCONH-R z -NHCONH-, S , R < t > and R < z > are, independently of each other, hydrocarbylene;
  • B 1 and B 2 independently of one another are hydrocarbyl or , R a is hydrogen or (C 1 -C 10 ) alkyl, and any one of B 1 and B 2 is ;
  • A is selected from the following formulas,
  • R 5 to R 9 independently of one another are hydrogen, (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or , T is an integer selected from 0 to 20, R is independently from each other hydrogen or (C 1 -C 10 ) alkyl,
  • R is independently hydrogen or (C 1 -C 10) alkyl each other
  • T is Is a straight or branched group derived from a polyether oligomer, wherein Z 1 to Z 3 are independently from each other are selected from - (CR 11 R 12) s - a, and the R 11 to R 12 are independently hydrogen or (C 1 -C each other 5 ) alkyl, and s is an integer selected from 1 to 5;
  • 1 is an integer selected from 1 to 200, and m and n are independently an integer selected from 0 to 200.
  • R and R 11 to R 12 are independently of each other hydrogen or (C 1 -C 5 ) alkyl; And s may be an integer selected from 1 to 3.
  • the monomer represented by the formula (1) may be represented by the following formula (2).
  • R, R a and R 1 to R 4 are independently of each other hydrogen or (C 1 -C 10 ) alkyl;
  • R 5 to R 9 independently of one another are hydrogen, (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or , T is an integer selected from 0 to 20;
  • R a1 To R a2 , R a4 R a and R a10 to R a12 are independently of each other hydrogen or (C 1 -C 10 ) alkyl;
  • o, p, a and b are each independently an integer selected from 1 to 10;
  • T is Is a straight or branched group derived from a polyether oligomer, wherein Z 1 to Z 3 are independently from each other are selected from - (CR 11 R 12) s - a, and the R 11 to R 12 are independently hydrogen or (C 1 -C each other 5 ) alkyl, and s is an integer of 1 to 3;
  • 1 is an integer selected from 1 to 200, and m and n are independently an integer selected from 0 to 200.
  • the weight average molecular weight of the siloxane macromonomer may be 3,000 to 30,000 g / mol.
  • the polymer composition may include 5 to 60% by weight of the siloxane macromonomer.
  • the polymer composition may further include a reactive monomer.
  • the reactive monomer contained in the polymerization composition may be any one or a mixture of two or more selected from hydrophilic acrylic monomers, hydrophilic silicon acrylic monomers, and vinyl monomers.
  • the silicone hydrogel lens according to the present invention comprises a siloxane macromonomer containing 1 to 10 glyceryl repeating units in the main chain and side chain of the siloxane macromonomer, so that the oxygen permeability is extremely high and the surface contact angle is remarkably low .
  • the silicone hydrogel lens according to the present invention can realize a high water content and an appropriate modulus, thereby improving the wearing comfort of the lens.
  • the silicone hydrogel lens of the present invention does not provide inconvenience to wear for a long time, and gives excellent effects to the prevention of various ophthalmic diseases.
  • the term " hydrogel " refers to a polymeric material that is swellable or swellable by water in water and typically represents a network or matrix of polymer chains. At this time, the network or matrix may not be crosslinked or crosslinked.
  • the hydrogel refers to a polymeric material including contact lenses that are water-swellable or water-swellable.
  • the hydrogel may be (i) unhydrated and water swollen, (ii) partially hydrated and swollen with water, or (iii) fully hydrated and swollen with water.
  • the term "polymeric composition” is understood to mean the same as the polymerization mixture, and may be understood to be prepolymerized or precured to suit the polymerization.
  • the polymeric composition may be a lens precursor composition and may be represented as a monomeric mix.
  • the polymerizable composition may not be polymerized before curing or polymerization, and may be partially polymerized.
  • the term " monomer " refers to a compound that is polymerizable regardless of the molecular weight of the compound.
  • the monomer may be a low molecular weight monomer, an oligomer, a macromer, or the like.
  • the term "low molecular weight monomer” refers to a compound that is polymerizable and refers to a compound having a relatively low molecular weight, for example, a compound having an average molecular weight of less than 700 daltons.
  • the low molecular weight monomer may be a polymer comprising a single unit of a molecule containing at least one functional group capable of forming a polymer by combining with another molecule having the same structure or different structure as the low molecular weight monomer .
  • the term " macromer " refers to a compound that is polymerized to include one or more functional groups that can be polymerized or further polymerized, and may be a medium molecular weight, high molecular weight compound or polymer.
  • the macromer can be a compound or polymer having an average molecular weight of from 700 daltons to 2,000 daltons.
  • copolymer refers to a material formed by the polymerization of one or more monomers, macromers, or mixtures thereof.
  • the copolymer is not polymerizable, but is understood to be a material that can be crosslinked by the reaction of other monomers, macromers, and mixtures thereof in the polymerizable composition.
  • " hydrocarbyl " as used herein means a radical having one bonding position derived from a hydrocarbon, and the term " hydrocarbylene " means a radical having two bonding positions derived from a hydrocarbon.
  • the term " alkyl " includes both linear and branched forms.
  • the alkyl may have 1 to 10 carbon atoms, specifically 1 to 7 carbon atoms, more specifically 1 to 5 carbon atoms.
  • haloalkyl means that at least one halogen is substituted at the hydrogen position of the alkyl, and the halogen means an atom such as fluorine, chlorine, bromine or iodine.
  • the silicon content in order to impart a high oxygen permeability to a contact lens, the silicon content must be increased, but when the hydrophobic silicon content is increased, the moisture content is lowered.
  • the inventors of the present invention have been studying silicone hydrogel lenses satisfying all of the above characteristics, and a silicone hydrogel lens made of a polymerizable composition containing a specific functional group-introduced siloxane macromonomer Characteristics, and the present invention has been completed.
  • the silicone hydrogel lens according to an embodiment of the present invention has excellent oxygen permeability, water content, and surface contact angle, thus providing extremely improved wearing comfort and stability.
  • the silicone hydrogel lens of the present invention may comprise a main chain, a side chain of siloxane macromonomers or 1 to 10 glyceryl repeating units thereof, and may be made of a polymer composition containing the siloxane macromonomer
  • the silicone hydrogel lens may satisfy all of the following characteristics.
  • the siloxane macromonomer which is a polymerizable monomer contained in the polymer composition, has a main chain; Side chain; Or a glyceryl repeat unit derived from a glyceryl derivative in a main chain and a side chain.
  • the siloxane macromonomer may be derived from 3- (allyloxy) propane-1,2-diol in its main chain, side chain or main chain and side chain with 3- Wherein the glyceryl repeating unit is the main chain of the siloxane macromer; Side chain; Or combined with the carbon of the main chain and the side chain.
  • the glyceryl repeating unit includes all of those derived from and introduced with other functional groups in place of hydrogen atoms of glyceryl.
  • the siloxane macromonomer may contain 1 to 10 glyceryl repeating units in the main chain of the siloxane macromonomer.
  • the siloxane macromonomer may include 1 to 10 glyceryl repeating units in the main chain and side chain of the siloxane macromonomer.
  • the silicone hydrogel lens according to an embodiment of the present invention may be one in which the main chain, side chain, or halo (C 1 -C 10 ) alkyl of the siloxane macromonomer is further introduced, specifically, the siloxane macromonomer (C 1 -C 10 ) alkyl in the main chain, the side chain, or both of them, thereby imparting good coloring resistance.
  • the silicone hydrogel lens may satisfy physical properties such as an oxygen permeability of 100 barrer or more, a surface contact angle measured by a trapped bubble method of 40 ° or less, and a water content of 55 to 70%.
  • the silicone hydrogel lens may satisfy physical properties such as an oxygen permeability of 110 barrer or more, a surface contact angle measured by a trapped air bubble method of 35 ° or less, and a water content of 55 to 70%. More specifically, A surface contact angle measured by a trapped bubble method of 35 ° or less, and a water content of 60 to 70%.
  • the silicone hydrogel lens satisfies the above-mentioned physical properties and satisfies the modulus in the range of 0.3 to 0.9, thereby giving a smooth and stable feeling of wearing the lens.
  • the silicone hydrogel lens may specifically have a modulus in the range of 0.3 to 0.6, more specifically in the range of 0.3 to 0.5.
  • the silicone hydrogel lens having excellent physical properties as described above may have one to ten glyceryl repeating units and two or more hydroxy groups introduced into the main chain and the side chain of the siloxane macromonomer.
  • the polymerization may be any polymerization within a range that can be recognized by a person skilled in the art.
  • it may be a radical polymerization. Specifically, .
  • the siloxane macromonomer may be a monomer represented by the following formula (1).
  • R 1 to R 4 are independently of each other hydrogen or (C 1 -C 10 ) alkyl
  • R a1 to R a12 independently from each other are hydrogen, hydroxy or (C 1 -C 10 ) alkyl;
  • o and a are each independently an integer selected from 1 to 10;
  • p, q, b and c are each independently an integer selected from 0 to 10;
  • D 1 and D 2 are independently of each other a single bond, -NHCOO-, -NHCONH-, -OCONH-R S -NHCOO-, -NHCONH-R t -NHCONH- and -OCONH-R z -NHCONH-, S , R < t > and R < z > are, independently of each other, hydrocarbylene;
  • B 1 and B 2 independently of one another are hydrocarbyl or , R a is hydrogen or (C 1 -C 10 ) alkyl, and any one of B 1 and B 2 is ;
  • A is selected from the following formulas,
  • R 5 to R 9 independently of one another are hydrogen, (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or , T is an integer selected from 0 to 20, R is independently from each other hydrogen or (C 1 -C 10 ) alkyl,
  • R is independently hydrogen or (C 1 -C 10) alkyl each other
  • T is Is a straight or branched group derived from a polyether oligomer, wherein Z 1 to Z 3 are independently from each other are selected from - (CR 11 R 12) s - a, and the R 11 to R 12 are independently hydrogen or (C 1 -C each other 5 ) alkyl, and s is an integer selected from 1 to 5;
  • 1 is an integer selected from 1 to 200, and m and n are independently an integer selected from 0 to 200.
  • R, R 1 to R 4 , B 1 , B 2 , D 1 , D 2 , R a1 to R a12 o, p, q, a, b, c and Z 1 to Z 3 The same as the definition.
  • R and R 11 to R 12 are independently of each other hydrogen or (C 1 -C 5 ) alkyl; And s may be an integer selected from 1 to 3.
  • R is hydrogen or methyl;
  • R 11 to R 12 are independently of each other hydrogen or (C 1 -C 3 ) alkyl;
  • S may be an integer of 1 or 2.
  • R is hydrogen or methyl; R 11 to R 12 are hydrogen; And s may be an integer selected from 1 to 3.
  • p and b are each independently an integer of 1 or 2; Q and c are each independently an integer of 0 or 1; D 1 and D 2 may be a single bond.
  • A must be / RTI > And Containing macromonomer containing one or two or more repeating units selected from the above-mentioned repeating units, and these repeating units may be repeatedly included in any order.
  • the functional group Lt; / RTI > Lt; / RTI > is a straight-chain or branched-chain ether oligomer group derived from Can be represented by the following structural formula.
  • R 22 and R 23 are independently of each other hydrogen
  • R is independently hydrogen or (C 1 -C 10) alkyl with one another;
  • Z 1 to Z 3 are each independently - (CR 11 R 12 ) s -, wherein R 11 to R 12 independently of one another are hydrogen or (C 1 -C 5 ) alkyl, and s is selected from 1 to 3 Lt; / RTI >
  • R 5 is hydrogen, (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or T is an integer selected from 0 to 20;
  • l is an integer selected from 1 to 200.
  • the monomer represented by Formula 1 may be represented by Formula 2 below.
  • R, R a and R 1 to R 4 are independently of each other hydrogen or (C 1 -C 10 ) alkyl;
  • R 5 to R 9 independently of one another are hydrogen, (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or , T is an integer selected from 0 to 20;
  • R a1 To R a2 , R a4 R a and R a10 to R a12 are independently of each other hydrogen or (C 1 -C 10 ) alkyl;
  • o, p, a and b are each independently an integer selected from 1 to 10;
  • T is Is a straight or branched group derived from a polyether oligomer, wherein Z 1 to Z 3 are independently from each other are selected from - (CR 11 R 12) s - a, and the R 11 to R 12 are independently hydrogen or (C 1 -C each other 5 ) alkyl, and s is an integer selected from 1 to 3;
  • 1 is an integer selected from 1 to 200, and m and n are independently an integer selected from 0 to 200.
  • R 5 to R 9 independently represent (C 1 -C 10 ) alkyl, halo (C 1 -C 10 ) alkyl or , And t may be an integer selected from 0 to 20.
  • R 5 to R 9 may independently be (C 1 -C 10 ) alkyl or halo (C 1 -C 10 ) alkyl, and t may be an integer selected from 0 to 10.
  • R 5 is (C 1 -C 10 ) alkyl and R 6 is halo (C 1 -C 10 ) alkyl; And R 7 to R 8 may independently be (C 1 -C 10 ) alkyl.
  • 1 is an integer selected from 5 to 150; M and n are independently an integer selected from 0 to 150; R < 5 > is methyl; Wherein R < 6 & Halo (C 1 -C 2) alkyl; And R 7 to R 9 may be methyl.
  • the siloxane macromonomer may have a weight average molecular weight of 1,000 to 30,000 g / mol, and may specifically be 2,000 to 20,000 g / mol.
  • the siloxane macromonomer may have a block structure, and the block structure includes an irregular structure.
  • the polymerization composition for preparing the silicone hydrogel lens according to one embodiment of the present invention necessarily includes a siloxane macromonomer containing 1 to 10 glyceryl repeating units in the main chain and side chain of the siloxane macromonomer.
  • the polymerization composition of the present invention comprises a siloxane macromonomer and a reactive monomer having 1 to 10 glyceryl repeating units or 1 to 10 glyceryl repeating units and a hydroxy group introduced into the main chain and side chain of the siloxane macromonomer At least one additive selected from crosslinking agents, initiators, and the like.
  • the polymerizable composition for preparing a silicone hydrogel lens according to an embodiment of the present invention may have a viscosity of 10 to 20,000 cP measured at 25 ° C, and more preferably 50 to 10,000 cP. When the viscosity in the above range is satisfied, it is good because the productivity is excellent when injected into the mold part.
  • the siloxane macromonomer may be contained in an amount of 5 to 60% by weight based on the total weight, specifically 10 to 60% by weight, more specifically, By weight and 15 to 60% by weight. At this time, when the above range is satisfied, excellent physical properties such as wettability can be achieved, but it is not limited thereto.
  • the reactive monomer is a monomer having a functional group capable of reacting with the siloxane monomer, and may be specifically a hydrophilic monomer.
  • the hydrophilic monomer is not limited as long as it is commonly used in the art.
  • Non-limiting examples of the hydrophilic monomer include a hydrophilic acrylic monomer, a hydrophilic silicone acrylic monomer, a vinyl monomer, and the like.
  • Non-limiting examples of the hydrophilic acrylic monomer include C 1 -C 15 hydroxyalkyl methacrylate substituted with 1 to 3 hydroxy groups, C 1 -C 15 hydroxyalkyl substituted with 1 to 3 hydroxy groups Acrylate, acrylamide, vinyl pyrrolidone, glycerol methacrylate, acrylic acid, and methacrylic acid, and specifically, 2-hydroxyethyl methacrylate (2-hydroxyethyl methacrylate, HEMA), N-dimethyl acrylamide (DMA), N-vinyl pyrrolidone (NVP), glycerol monomethacrylate monomethacrylate, GMMA) and methacrylic acid (MAA).
  • HEMA 2-hydroxyethyl methacrylate
  • DMA N-dimethyl acrylamide
  • NDP N-vinyl pyrrolidone
  • GMMA methacrylic acid
  • MAA methacrylic acid
  • the hydrophilic silicone acrylic monomer may include a polydimethylsiloxane-based compound, and the non-limiting examples thereof include tris (3-methacryloxypropyl) silane, 2- (trimethylsilyloxy) ethylmethacrylate, 3- (Trimethylsilyloxy) silylpropyl methacrylate, 3-methacryloxypropyltris (trimethylsilyl) silane (MPTS), 3-methacryloxy-2- (hydroxypropyloxy) Silane and 4-methacryloxybutyl terminated polydimethylsiloxane, and the like.
  • tris (3-methacryloxypropyl) silane 2- (trimethylsilyloxy) ethylmethacrylate
  • 3- (Trimethylsilyloxy) silylpropyl methacrylate 3-methacryloxypropyltris (trimethylsilyl) silane (MPTS), 3-methacryloxy-2- (hydroxypropyloxy) Silane and 4-methacryloxybutyl
  • the vinyl monomer is a compound having at least one vinyl group.
  • Non-limiting examples of the vinyl monomer include N-methyl-3-methylene-2-pyrrolidone, Methyl-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, Pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl- Methyl-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, N- Vinyl pyrrolidone (NVP), allyl alcohol, vinyl pyridine, N-vinyl formamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-methylacetamide, - vinyl caprolactam, and the like.
  • hydrophobic monomer may be used together if necessary.
  • the hydrophobic monomer is not limited as long as it is commonly used in the art, and hydrophobic acrylic monomers and the like can be used as non-limiting examples thereof.
  • the hydrophobic acrylic monomers include alkyl acrylate monomers and alkyl methacrylate monomers.
  • Non-limiting examples of the hydrophobic acrylic monomers include methyl acrylate, methyl methacrylate, ethyl acrylate, acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, n-butyl acrylate, n N-butyl methacrylate, stearyl acylate, stearyl methacrylate, and the like may be used.
  • the hydrophobic acrylic monomer may be a monomer having a high glass transition temperature (T g ), and examples thereof include cyclohexyl methacrylate, tert-butyl methacrylate ) And isobornyl methacrylate, and the like.
  • T g glass transition temperature
  • examples thereof include cyclohexyl methacrylate, tert-butyl methacrylate ) And isobornyl methacrylate, and the like.
  • the reactive monomer may be contained in an amount of 30 to 95% by weight based on the total weight of the polymerizable composition, and specifically 35 to 90% But is not limited thereto.
  • the use of the reactive monomer can simultaneously manifest the physical properties of the added reactive monomer while achieving the desired releasability in the above range.
  • the crosslinking agent which is one example of the additive is not limited as long as it is commonly used in the art, and non-limiting examples thereof include ethylene glycol dimethacrylate (EGDMA), diethylene glycol methacrylate (DGMA), divinylbenzene and Trimethylolpropane trimethacrylate (TMPTMA), and the like can be used.
  • EGDMA ethylene glycol dimethacrylate
  • DGMA diethylene glycol methacrylate
  • TMPTMA Trimethylolpropane trimethacrylate
  • the crosslinking agent may be contained in the polymer composition in an amount of 0.005 to 5% by weight, specifically 0.05 to 3% by weight, more specifically 0.1 to 1% by weight.
  • the initiator which is an example of the additive, is for polymerization and is not limited as long as it is commonly used in the art.
  • Non-limiting examples of the initiator include azobisisobutylonitrile (AIBN), benzoin methyl ether (BME) 2,5-dimethyl-2,5-di- (2-ethylhexanoylperoxy) hexane and dimethoxyphenylacetophenone (DMPA).
  • the initiator may be contained in the polymerization composition in an amount of 0.005 to 2% by weight, specifically 0.01 to 1% by weight, more specifically 0.01 to 0.1% by weight.
  • additives may include a colorant, an ultraviolet blocking agent, a UV blocking agent and the like. These may be included in the polymer composition in an amount of 0.01 to 2% by weight, and more specifically 0.05 to 1.5% by weight.
  • the unit of mass not specifically mentioned in the specification may be g.
  • the specimens for example, the lenses of Examples or Comparative Examples
  • the specimens were immersed in PBS solution at room temperature for 24 hours and then stored at 35 ° C ⁇ 0.5 ° C for at least 2 hours Respectively. Thereafter, the specimen was placed in an incubator, and oxygen permeability (refractive index) was measured using an oxygen permeability measuring device (Model 201T, Rehder Development Co., West Lafayette, USA) in a lens moisture saturation state at a temperature of 35 ° C ⁇ 0.5 ° C and a humidity of 98% Dk: barrer (10 -11 (cm 2 mL (STP) O 2 ) / sec mL mmHg) was measured.
  • the surface contact angle (°) was measured by a captive air bubble method using a contact angle meter (DSA 100).
  • the specimen for example, the lens of the example or the comparative example
  • the specimen was attached to a supporter, immersed in saline at 25 ° C, and a bubble was attached to the surface of the specimen using a syringe, and the surface contact angle was measured by dropping the saline solution.
  • the weight of the swollen specimen after measuring the weight of the dried specimen (for example, the lens of the example or the comparative example) and the aqueous solution of 0.9 wt% sodium chloride (NaCl) And evaluated using the following equation (1). That is, the water content was evaluated as the ratio of the weight of the swollen specimen (W swell ) to the dry weight (W dry ).
  • the specimens eg, lenses of Examples or Comparative Examples
  • PBS standard physiological saline
  • the specimens were fixed flat and cut using a specimen cutter.
  • the cut specimen was fixed to the upper clamp of the measuring instrument and fixed to the lower clamp, and the interval between the upper and lower clamps was set to 4 mm.
  • the thickness of the specimen measured by the thickness gauge was input and the measurement was started. At this time, the measurement unit of modulus is indicated by MPa.
  • the weight average molecular weight was measured using a gel permeation chromatography (GPC) instrument manufactured by Waters.
  • the equipment consists of a mobile pump (1515 Binary Pump), a column heater (1500 Series), a detector (2414 RI Detector) and an injector (2707 automatic injector).
  • the analytical columns are Shodex KF-802, KF-802.5 and KF-803 Polystyrene (PS) SL-105 STD was used as a standard material.
  • HPLC grade tetrahydrofuran (THF) was used and the column heater temperature was 40 ° C and the mobile phase solvent flow rate was 1.0 mL / min.
  • the siloxane macromonomer prepared for the sample analysis was dissolved in tetrahydrofuran (THF), a mobile phase solvent, and then injected into a GPC machine to measure the weight average molecular weight.
  • the viscosity was measured using a Brookfield LVDV-2T viscometer.
  • the siloxane monomer was placed in a container at 25 ° C at room temperature and the viscosity was measured by rotating it at a speed of 10 rpm using a spindle (SC4-31).
  • Viscosity was measured with a viscometer to confirm the viscosity of 132 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 164 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 118 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 149 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • the obtained compound was identified as the compound of the above formula 4-5.
  • Viscosity was measured with a viscometer to confirm the viscosity of 104 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 144 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 87 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • the obtained product showed Si-CH 2 -CH 2 -CF 3 at ⁇ 0.06 to 0.12 ppm, Si-CH 3 at ⁇ 0.70 ppm (t, 20H) CH 2 CH 2 -CF 3 at ⁇ 5.60 to 6.15 ppm (dd, 4H), -CCH 3 ⁇ CH 2 at ⁇ 1.96 ppm (S, 6H), -CCH 3 ⁇ CH 2, ⁇ 0.76 ppm (m, 4H ) Si-CH 2 -CH 2 -CH 2 -O, ⁇ 1.69 ppm (m, 4H) Si-CH 2 -CH 2 -CH 2 -O, ⁇ 3.94 ppm in the (m, 4H) Si-CH 2 -CH 2 -CH 2 -O, ⁇ 3.60 ⁇ 3.80 ppm (m, 5H) O-CH 2 -CH-OH, O-CH 2 -CH-OH, O in A peak of -CH 2
  • Viscosity was measured with a viscometer to confirm the viscosity of 81 cP.
  • GPC analysis revealed a weight average molecular weight of 2,100 g / mol.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 76 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 115 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 144 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 121 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 128 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 175 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 118 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 149 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • the obtained product showed Si-CH 2 -CH 2 -CF 3 at ⁇ 0.06 to 0.12 ppm, Si-CH 3 at ⁇ 0.70 ppm (t, 20H) CH 2 CH 2 -CF 3 at ⁇ 5.60 to 6.15 ppm (dd, 4H), -CCH 3 ⁇ CH 2 at ⁇ 1.96 ppm (S, 6H), -CCH 3 ⁇ CH 2 , Si-CH 2 -CH 2 -CH 2 -O at ⁇ 0.76 ppm (m, 4H), Si-CH 2 -CH 2 -CH 2 -O at ⁇ 1.69 ppm (m, 4H) A peak of Si-CH 2 -CH 2 -CH 2 -O was confirmed at ppm (m, 4H).
  • Viscosity was measured with a viscometer to confirm the viscosity of 113 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 139 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • the obtained compound was identified as the compound of the above formula 6-7.
  • Viscosity was measured with a viscometer to confirm the viscosity of 118 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 78 cP.
  • GPC analysis revealed a weight average molecular weight of 1,870 g / mol.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 82 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 68 cP.
  • Viscosity was measured with a viscometer to confirm the viscosity of 115 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Viscosity was measured with a viscometer to confirm the viscosity of 75 cP.
  • Viscosity was measured with a viscometer to confirm a viscosity of 102 cP.
  • N-vinylpyrrolidone N-vinylpyrrolidone
  • HEMA 2-hydroxyethyl methacrylate
  • ELDMA ethylene glycol dimethacrylate
  • AIBN azobisisobutylonitrile
  • the polymer composition was injected into a female mold for cast molding, and a male mold was assembled into the female mold.
  • the assembled mold was placed in a heat oven maintained at 100 DEG C and polymerized for 1 hour, after which the mold was separated to obtain a lens.
  • the obtained lens was immersed in ethyl alcohol for 1 hour, immersed in deionized water for 1 hour, and then subjected to high-pressure sterilization in a phosphate buffered saline solution to prepare a silicone hydrogel lens.
  • Examples 1 to 9 according to the present invention show higher moisture content, higher oxygen permeability, lower surface contact angle, and appropriate modulus as compared with Comparative Examples 1 to 9. This is due to the effect of the siloxane macromonomer having a specific functional group contained in the polymerization composition of the embodiment, thereby providing a contact lens having a comfortable feeling for a long period of time by simultaneously satisfying a high water content and a high oxygen permeability.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)

Abstract

La présente invention concerne une lentille en hydrogel de silicone. La lentille en hydrogel de silicone selon la présente invention est produite à l'aide d'une composition polymère comprenant un macromonomère de siloxane dans lequel un groupe fonctionnel spécifique est introduit. Par conséquent, le silicone possède des propriétés physiques extrêmement améliorées et est confortable à porter pendant une longue période, et confère d'excellents effets dans la prévention de diverses maladies ophtalmiques.
PCT/KR2018/015076 2017-12-05 2018-11-30 Lentille en hydrogel de silicone ayant d'excellentes propriétés physiques Ceased WO2019112255A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170165601 2017-12-05
KR10-2017-0165601 2017-12-05
KR10-2018-0150615 2018-11-29
KR1020180150615A KR102715262B1 (ko) 2017-12-05 2018-11-29 우수한 물성을 가지는 실리콘 하이드로겔 렌즈

Publications (1)

Publication Number Publication Date
WO2019112255A1 true WO2019112255A1 (fr) 2019-06-13

Family

ID=66751104

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/015076 Ceased WO2019112255A1 (fr) 2017-12-05 2018-11-30 Lentille en hydrogel de silicone ayant d'excellentes propriétés physiques

Country Status (1)

Country Link
WO (1) WO2019112255A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11142870B2 (en) 2014-07-04 2021-10-12 Danapak Flexibles A/S Packaging sheet for packaging of cheese, and associated packaging and manufacturing methods
JP7451792B1 (ja) 2022-09-30 2024-03-18 ペガヴィジョン コーポレーション シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ
EP4165134A4 (fr) * 2020-06-15 2024-07-31 ForSight Vision6, Inc. Polymères de fluorosilicone, compositions et leurs utilisations
US12290433B2 (en) 2019-04-05 2025-05-06 Forsight Vision6, Inc. Fluorosilicone copolymers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08245737A (ja) * 1995-03-10 1996-09-24 Asahi Chem Ind Co Ltd 親水性含フッ素シロキサン単量体およびその組成物からなる眼科用レンズ材料
WO2001044861A1 (fr) * 1999-12-16 2001-06-21 Asahikasei Aime Co., Ltd. Lentille de contact souple pouvant etre portee longtemps
WO2015128636A1 (fr) * 2014-02-28 2015-09-03 Coopervision International Holding Company, Lp Lentilles de contact constituées de macromères polysiloxane compatibles avec l'hema
WO2016145204A1 (fr) * 2015-03-11 2016-09-15 University Of Florida Research Foundation, Inc. Contrôle de la taille de réseau de la lubrification dans des hydrogels jumeaux
CN106279699A (zh) * 2015-06-05 2017-01-04 永胜光学股份有限公司 一种硅水胶镜片基材的制备工艺
WO2017103790A1 (fr) * 2015-12-15 2017-06-22 Novartis Ag Agents de réticulation vinyliques de polydiorganosiloxane hydrophilisé et leurs utilisations
KR20180057540A (ko) * 2016-11-22 2018-05-30 주식회사 인터로조 습윤성이 우수한 실록산 단량체, 이를 포함하는 중합조성물 및 이를 이용하여 제조된 실리콘 하이드로겔 렌즈

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08245737A (ja) * 1995-03-10 1996-09-24 Asahi Chem Ind Co Ltd 親水性含フッ素シロキサン単量体およびその組成物からなる眼科用レンズ材料
WO2001044861A1 (fr) * 1999-12-16 2001-06-21 Asahikasei Aime Co., Ltd. Lentille de contact souple pouvant etre portee longtemps
WO2015128636A1 (fr) * 2014-02-28 2015-09-03 Coopervision International Holding Company, Lp Lentilles de contact constituées de macromères polysiloxane compatibles avec l'hema
WO2016145204A1 (fr) * 2015-03-11 2016-09-15 University Of Florida Research Foundation, Inc. Contrôle de la taille de réseau de la lubrification dans des hydrogels jumeaux
CN106279699A (zh) * 2015-06-05 2017-01-04 永胜光学股份有限公司 一种硅水胶镜片基材的制备工艺
WO2017103790A1 (fr) * 2015-12-15 2017-06-22 Novartis Ag Agents de réticulation vinyliques de polydiorganosiloxane hydrophilisé et leurs utilisations
KR20180057540A (ko) * 2016-11-22 2018-05-30 주식회사 인터로조 습윤성이 우수한 실록산 단량체, 이를 포함하는 중합조성물 및 이를 이용하여 제조된 실리콘 하이드로겔 렌즈

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11142870B2 (en) 2014-07-04 2021-10-12 Danapak Flexibles A/S Packaging sheet for packaging of cheese, and associated packaging and manufacturing methods
US12290433B2 (en) 2019-04-05 2025-05-06 Forsight Vision6, Inc. Fluorosilicone copolymers
EP4165134A4 (fr) * 2020-06-15 2024-07-31 ForSight Vision6, Inc. Polymères de fluorosilicone, compositions et leurs utilisations
JP7451792B1 (ja) 2022-09-30 2024-03-18 ペガヴィジョン コーポレーション シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ
JP2024052477A (ja) * 2022-09-30 2024-04-11 ペガヴィジョン コーポレーション シロキサンモノマー、コンタクトレンズ組成物及びコンタクトレンズ
US12441845B2 (en) 2022-09-30 2025-10-14 Pegavision Corporation Siloxane monomer, contact lens composition and contact lens

Similar Documents

Publication Publication Date Title
WO2019112255A1 (fr) Lentille en hydrogel de silicone ayant d'excellentes propriétés physiques
WO2017047917A1 (fr) Polyimide modifié et composition de résine durcissable le contenant
WO2023018307A1 (fr) Résine, son procédé de préparation, composition de résine et produit moulé
WO2017061826A1 (fr) Agent anti-buée
WO2017142343A1 (fr) Monomère de siloxane, composition pour la préparation d'une lentille en hydrogel de silicone le contenant, et lentille en hydrogel de silicone
WO2018097622A2 (fr) Monomère de siloxane, composition polymère le comprenant, et lentille en hydrogel de silicone préparée à l'aide de celui-ci
WO2016085087A9 (fr) Composés (méth)acryliques ayant un indice de réfraction élevé, leur procédé de préparation, feuille optique les comprenant, et dispositif d'affichage optique l'utilisant
WO2018097608A2 (fr) Monomère de siloxane ayant une excellente mouillabilité, composition polymère le comprenant, et lentilles d'hydrogel de silicone fabriquées à l'aide de ce dernier
WO2014193072A1 (fr) Film optique ayant une excellente fonction de coupure dans l'ultraviolet et plaque polarisante le comprenant
WO2023055206A1 (fr) Copolymère multi-séquencé, composition de résine le comprenant et son procédé de préparation
WO2018147617A1 (fr) Film de polyamide-imide et son procédé de production
WO2020218874A1 (fr) Composé de ligand, composé de métal de transition et composition de catalyseur le comprenant
WO2024043663A1 (fr) Résine de polycarbonate et procédé de production associé
WO2023055204A1 (fr) Copolymère à blocs multiples et son procédé de préparation
WO2022182014A1 (fr) Structure de cristal photonique et son procédé de fabrication
WO2022145795A1 (fr) Composition de résine photosensible négative ayant une aptitude au durcissement à basse température et un faible indice de réfraction
WO2018221967A1 (fr) Composition pour la polymérisation d'un hydrogel, polymère d'hydrogel dérivé de celle-ci et lentille hydrogel en comprenant
WO2021221374A1 (fr) Film composite à base de polyamide et dispositif d'affichage le comprenant
WO2023113359A1 (fr) Composition de lentille intelligente et lentille intelligente fabriquée à l'aide de cette dernière
WO2016133305A1 (fr) Caoutchouc modifié à base d'isobutylène-isoprène, procédé de préparation de celui-ci, et produit vulcanisé
WO2020130552A1 (fr) Composé diamine, précurseur de polyimide utilisant ce dernier et film de polyimide
WO2023182805A1 (fr) Composition de démoulage
WO2025211533A1 (fr) Bouchon méatique comprenant un polymère à mémoire de forme et son procédé de fabrication
WO2018159976A2 (fr) Oligomères de siloxane thiol et de siloxane (méth)acrylate pour matériau optique
WO2023055205A1 (fr) Copolymère multibloc et son procédé de préparation

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18886703

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18886703

Country of ref document: EP

Kind code of ref document: A1