TH49984A - Method of preparation of polymersets applied to the eye. - Google Patents

Abstract

DC60 (09/02/44) This invention is directed towards a method of preparing a polymerize, which includes a step of polymerizing a two-component mixture, including a first component consisting of at least one polycyanate reactant with at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these; the polycyanate reactant being a product of a polythiol monomer with at least two thiol groups; and a polycyanate monomer with at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these. And a second component consisting of at least one polyamine reactant containing at least two functional groups selected from primary amines, secondary amines, and combinations of these. This invention also aims at the polymerizes prepared according to the method of this invention. This invention also aims at the photochromic substances that may be prepared from the polymerizes of this invention. This invention aims at the method of preparing the polymerizes, including the polymerization procedure of the two-component mixture, which includes a first component consisting of at least one polycyanate reactant containing at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these; the polycyanate reactant being a product of the reaction of a polythiol monomer containing at least two thiol groups and a polycyanate monomer containing at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these. And a second component consisting of at least one polyamine reactant containing at least two functional groups selected from primary amines, secondary amines, and the combination of these substances. This invention also aims at polymerizes prepared according to the method of this invention. This invention also aims at photochromic substances that may be prepared from the polymerizes of this invention.

Claims (103)

Revised 08/10/2015 1. Method for preparing a polymerize consisting of a two-component polymerization step consisting of (a) Component 1, which contains at least one reactant with at least two functional groups selected from isocyanates, isothiocyanates, or combinations of these. The reactant is the product of the reaction of (i) a polythol monomer containing at least two thiol groups, (ii) a monomer containing at least two functional groups selected from isocyanates, isothiocyanates, or combinations of these, and (b) Component 2, which contains at least one polyamine reactant with at least two functional groups selected from primaryamines, secondaryamines, or combinations of these. Or the combination of these substances where such first and second components are chosen when they are polymerized, the resulting polymerize has a refractive index of at least 1.6, an Abbe value of at least 33, and a Barkol hardness of at least 1. 2. Method of Reputation 1 where such first component also contains (iii) a reactive hydrogen material with at least two reactive hydrogen groups, a reactive hydrogen material chosen from polyol-containing materials, and materials containing both hydroxyl and thiol groups, and a mixture of these materials. 3. Method of Reputation 1 where the stoichiometric ratios of (i) and (ii) in such first component are chosen so that the molar equivalence ratio of (NCO+NCS)/(SH) is greater than 1.0. 4. Method of Reputation 1 where the stoichiometric ratios of (i), (ii), and (iii) are chosen so that The molar equivalent ratio of (NCO₃+NCS)/(SH+OH) ranges from 1.2 : 1.0 to 4.0 : 1.0. 1. Method for preparing a polymerize consisting of a polymerization step of a two-component mixture containing (a) Component 1, which contains at least one polycyanate reactant with at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these, where the polycyanate reactant is the product of the reaction of (i) a polythiol monomer containing at least two thiol groups, (ii) a polycyanate monomer containing at least two functional groups selected from isocyanates, isothiocyanates, and combinations of these, and (b) Component 2, which contains at least one polyamine reactant with at least two functional groups selected from primary amines, secondary amines, and combinations of these. 2. Method of claim 1 in which such element 1 also consists of (iii) a reactive hydrogenated material containing at least two reactive hydrogenated groups, which is a selectable reactive hydrogenated material from polyol-containing materials and materials containing both hydroxyl and thiol groups, and a mixture of these materials. 3. Method of claim 1 in which the stoichiometric quantities of (i) and (ii) in such element 1 are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH) is greater than 1.0. 4. Method of claim 1 in which the stoichiometric quantities of (i), (ii) and (iii) contained in such element 1 are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH) is greater than 1. 5. Method of Claim 1 in which such 1st and 2nd components are chosen such that when they are polymerized, the resulting polymerize has a refractive index of at least 1.3, an Abbe number of at least 33, and an initial Barcol stiffness of at least 1. 6. Method of claim 2 in which the stoichiometric quantities of (i), (ii) and (iii) are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH) ranges from 1.2:1.0 to 4.0:1.0. 7. Method of Claim 1 in which such polythiol monomer can be selected from a group consisting of (chemical formula). 8. The method of claim 7 in which such polythiol oligomers have disulfide crosslinks and are prepared by reacting polythiol monomers with sulfur, which has a basic catalyst. 9. The method of claim 7 in which such polythiol oligomers can be represented by a general structural formula (chemical formula) where n is an integer from 1 to 21. 10. Method of claim 7 in which such polythiol oligomer can be represented by a general structural formula (chemical formula). 11. Method of Claim 1 where such polycyanate monomer is a polycyanate containing at least two isocyanate groups. 12. Method of claim 1 in which such polycyanate monomer is a polycyanate that has one or more sulfur atoms in its structure. 13. Method of claim 1 in which such polycyanate monomer is a polycyanate that has one or more sulfur atoms in its structure, it is a substance with a general structure (chemical formula). 14. Method of claim 11 in which such polycyanate monomer is selected from the constituent groups (chemical formula). 15. Method of Claim 1 in which such polyamine actinator contains such 2nd element is selectable from the group containing ethyleneamine C1-C2, dialkyltoluene, diamine, methylenedianiline, trimethyleneglycol di(para-aminobenzote), where the diamine is represented by the general structural formula (A) (chemical formula), diamine represented by the general structural formula (B) (chemical formula), and diamine represented by the general structural formula (C). 16. Method of claim 15 in which diamines of general structural formula (A) can be selected from one or more groups of the constituent groups (chemical formula). 17. Method of claim 15 in which diamines of general structural formula (B) can be selected from one or more of the groups that comprise (chemical formula). 18. Method of claim 15 in which diamines of general structural formula (C) can be chosen from one or more groups of the constituent groups (chemical formula). 19. The method of claim 1 also involves the step of adding a catalyst to a two-component mixture. 20. The method of claim 16 in which such catalyst is selected from groups consisting of tertiaryamine and organometal compounds. 21. The method of claim 1 also includes the steps of the first and second component mixtures. 22. The method of claim 1 also includes the step of removing the gas of the first aforementioned element. 23. The method of claim 1 also includes the procedure of removing the gas of the aforementioned 2nd element. 24. The method of claim 1 also involves the step of adding the ingredients to the mold. 25. The method of claim 24 also consists of the steps of heating the mold and the mixture of the first and second components mentioned above within the mold. 26. The method of claim 25, where the heating procedure includes heating the mold and the mixture to a temperature of up to 200 degrees Celsius for an extended period of 0.5 to 72 hours. 27. Method of Claim 1 in which the first and second components are polymerized together in sufficient quantities to obtain a molar equivalent ratio of (NCO+NCS) to (-NH2+-NH-) groups from 0.5 to 3.0. 28. The method of Claim 1 also includes a procedure for adding additives selected from a group consisting of photostabilizers, heat stabilizers, antioxidants, ultraviolet light absorbers, mold-releasing agents, non-mutagenic (non-photochromic) dyes, pigments, and modifiable additives, and anti-yellowing additives, and mixtures of such additives. 29. Method of claim 28 where the additive is present in a mixture of two such components in an amount up to 10% by weight of the mixture of two such components. 30. Method of Claim 1 in which the said polymerize also contains a photochromic substance. 31. A polymerizet prepared by polymerizing a two-component mixture consisting of (a) a first component containing at least one polycyanate reactant with at least two functional groups selected from isocyanates, isothiocyanates, and combinations thereof, in which the polycyanate reactant is a product of the reaction of (i) a polythiol monomer containing at least two thiol groups, (ii) a polycyanate monomer containing at least two functional groups selected from isocyanates, isothiocyanates, and combinations thereof, and (b) a second component containing at least one polyamine reactant with at least two functional groups selected from primary amines, secondary amines, and combinations thereof. 32. A polymerize of claim 31 in which the first such composition also consists of (iii) a reactive hydrogenated material with at least 2 reactive hydrogenated groups, which is selectively reactive hydrogenated from polyol-containing materials and materials containing both hydroxyl and thiol groups, and a mixture of these materials. 33. A polymerize of claim 31 in which the stoichiometric ratios of (i) and (ii) in the first component are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH) is greater than 1.0. 34. A polymerize of claim 32 in which the stoichiometric quantities of (i), (ii), and (iii) contained in the first component are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH+OH) is greater than 1. 35. A polymerizer of claim 31 in which the first and second aforementioned components are selected so that it is polymerized, resulting in a refractive index of at least 1.6, an Abbe number of at least 33, and an initial bar stiffness of at least 1. 36. A polymerize of claim 34 in which the stoichiometric ratios of (i), (ii) and (iii) are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH+OH) ranges from 1.2:1.0 to 4.0:1.0. 37. A polymerize of claim 31 where such polythiol monomer is selectable from groups consisting of (chemical formula). 38. A polymerize of claim 37 in which such polythiol oligomer has a disulfide crosslinking and is prepared by reacting the polythiol monomer with sulfur, which contains a basic catalyst. 39. The polymerize of claim 37 where the polythiol oligomer is represented by a general structural formula (chemical formula) where n is an integer from 1 to 21. 40. Polymerization of claim 37 where such polythiol oligomer is represented by a general structural formula (chemical formula). 41. A polymerize of claim 31 where such polycyanate monomer is a polycyanate containing at least two isocyanate groups. 42. Polymerization of claim 41 in which such polycyanate monomer is selectable from groups consisting of (chemical formula). 43. Polymerization of claim 31 where such polyamine reactant of such second component is selectable from the group containing ethyleneamine C1-C2, dialkyltoluene, diamine, methylenedianiline, trimethyleneglycol di(para-aminobenzote), where the diamine is represented by the general structural formula (A) (chemical formula), the diamine represented by structural formula (B) (chemical formula), and the diamine represented by structural formula (C). 44. Polymerization of claim 43 in which diamine of general structural formula (A) can be selected from one or more of the groups comprising (chemical formula). 45. Polymerization of claim 43 in which diamine of general structural formula (B) can be selected from one or more groups of the constituent groups (chemical formula). 46. Polymerization of claim 43 in which diamine of general structural formula (C) can be selected from one or more groups of the constituent groups (chemical formula). 47. A polymerizer of claim 31 in which a catalyst is added to a mixture of the two components to induce polymerization. 48. A polymerize of claim 47 where such catalyst is selectable from groups containing tertiaryamines and organometallic compounds. 49. Polymerization of claim 31 where the polymerization process also involves mixing the first component and the second component. 50. Polymerization of claim 31 in which the polymerization process also includes a step for removing the gases of the first component. 51. Polymerization of claim 31 in which the polymerization process also includes a step for removing the gases of the aforementioned second component. 52. Polymerization of claim 49 in which the polymerization process also includes a step of adding the mixture to the mold. 53. Polymerization of claim 52 in which the polymerization process also consists of a step of heating the mold and the mixture of the first and second aforementioned components within the mold. 54. Polymerization of the claim 53 where such heating also includes heating the mold and mixture to a temperature up to 200 °C beyond the range from 0.5 to 72 cm. 55. A polymerize of claim 31 in which the first and second components are polymerized together in sufficient quantities to give a molar equivalent ratio of (NCO+NCS) to (-NH2+-NH-) groups from 0.5 to 3.0. 56. The polymerizes of claim 31 also contain additives selected from groups containing light stabilizers, heat stabilizers, antioxidants, ultraviolet light stabilizers, absorbers, mold-releasing agents, non-changing (non-photochromic) dyes, colorimetric pigments and additives, and anti-yellowing additives and mixtures of such additives. 57. Polymerizes of claim 56 where the additive is present in such polymerize in an amount up to 10% by weight of the polymerize. 58. The polymerize of claim 31 also contains a photochromic substance. 59. Photochromic objects obtained from polymerized mixtures prepared by polymerizing a two-component mixture consisting of (a) a first component containing at least one polycyanate reactant with at least two functional groups selected from isocyanates, isothiocyanates, and combinations thereof, in which the polycyanate reactant is the product of (i) a polythiol monomer containing at least two thiol groups, and (ii) a polycyanate monomer containing at least two functional groups selected from isocyanates, isothiocyanates, and combinations thereof, and (b) a second component containing at least one polyamine reactant with at least two functional groups selected from primary amines, secondary amines, and combinations thereof. 60. Photochromic material of claim 59 in which the first such element also consists of (iii) a reactive hydrogen material containing at least two reactive hydrogen groups, a reactive hydrogen material selected from polyol-containing materials and materials containing both hydroxyl and thiol groups, and mixtures of these materials. 61. The photochromic item of claim 59 in which the stoichiometric quantities of (i) and (ii) in the first said element are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH) is greater than 1.0. 62. The photochromic object of claim 60 in which the stoichiometric quantities of (i), (ii), and (iii) contained in the first component are chosen so that the molar equivalent ratio of (NCO+NCS)/(SH+OH) is greater than 1. 63. A photochromic substance of claim 59 in which the first and second such element are selected for its polymerization shall have a minimum refractive index of 1.6, a minimum Abbe number of 33, and a minimum initial barcoll hardness of 1. 64. The photochromic items of claim 60 in which the stoichiometric quantities of (i), (ii) and (iii) are chosen to give the molar equivalent ratio of (NCO+NCS)/(SH+OH) from 1.2:1.0 to 4.0:1.0. 65. The photochromic object of claim 59 in which such polythiol monomer is selectable from the constituent groups (chemical formula). 66. A photochromic object of claim 65 in which such polythiol oligomer has disulfide crosslinks and is prepared by reacting the polythiol monomer with sulfur containing a basic catalyst. 67. The photochromic object of claim 65 where such polythiol oligomer is represented by a general structural formula (chemical formula) where n is an integer from 1 to 21. 68. The photochromic object of claim 65 in which the polythiol oligomer can be represented by a general structural formula (chemical formula). 69. A photochromic item of claim 59 in which such polycyanate monomer is a polycyanate containing at least two isocyanate groups. 70. The photochromic substance of claim 69 in which such polycyanate monomer is selectable from a group consisting of (chemical formula). 71. The photochromic substance of claim 59 in which such polyamine reactant of such second element is selectable from the groups consisting of ethyleneamine C1-C2, dialkyltoluene, diamine, methylenedianiline, trimethylene glycol di(para-aminobenzote), where diamine is represented by the general structural formula (A) (chemical formula), diamine represented by the general structural formula (B) (chemical formula), and diamine represented by the general structural formula (C). 72. Method of claim 71 in which diamine of general structural formula (A) can be chosen from one or more groups of the constituent groups (chemical formula). 73. Method of claim 71 in which diamines of general structural formula (B) can be selected from one or more of the groups that comprise (chemical formula). 74. Method of claim 71 in which diamine of general structural formula (C) can be chosen from one or more of the groups it comprises (chemical formula). 75. A photochromic substance of claim 59 in which a catalyst is added to the aforementioned two-component mixture to aid in polymerization. 76. The photochromic object of claim 75 in which such catalyst is selectable from groups consisting of tertiaryamines and organometallic compounds. 77. The photochromic substance of claim 59 in which the polymerization process also includes a step of mixing the first and second aforementioned components. 78. The photochromic object of claim 59 in which the polymerization process also includes a step of gas removal of the first such element. 79. The photochromic material of claim 59 in which the polymerization process also includes a step for the removal of the aforementioned second component gas. 80. The photochromic object of claim 59 in which the polymerization process also includes a step of adding a mixture of the first and second components to a mold. 81. The photochromic material of claim 80 in which the polymerization process also includes a step of heating the mold and the mixture within the mold. 82. Photochromic items of claim 81 where the heating procedure includes heating the mold and such mixture to a temperature of up to 200 degrees Celsius for a duration exceeding the range of 0.5 to 75 cm. 83. A photochromic substance of claim 59 in which the first and second components are polymerized together in sufficient quantities to give a molar equivalent ratio of (NCO+NCS) to (-NH2+-NH-) groups of 0.5 to 3.0. 84. The photochromic items of claim 59 also include additives selected from groups containing photostabilizers, heat stabilizers, antioxidants, ultraviolet stabilizers, absorbers, release agents, non-changing (non-photochromic) fixed dyes, pigments and non-changing additives, and anti-yellowing additives and mixtures of such additives. 85. Photochromic material of claim 84 where the additive is present in the polymerize in an amount up to 10% by weight of the polymerize. 86. The photochromic material of claim 59 also contains photochromic substances. 87. The photochromic substance of claim 86 in which the photochromic substance is mixed with the first such element. 88. The photochromic substance of claim 86 in which the photochromic substance is mixed with the second component as mentioned. 89. Photochromic objects of claim 86 whereby a photochromic substance is applied to such photochromic object at a concentration of 0.15 to 0.35 mg per square centimeter of the surface area of the photochromic object. 90. Photochromic substances of claim 86 in which a photochromic substance is selectable from a group consisting of (chemical formula). 91. A photochromic substance of claim 86 in which the photochromic substance exhibits maximum absorption of excited light within the visible range of 590 to 700 nanometers. 92. A photochromic substance of claim 86 in which the photochromic substance exhibits maximum absorption of excited light within the visible range of 400 to 500 nanometers. 93. A photochromic substance of claim 86 in which the photochromic substance exhibits maximum absorption of excited light within the visible range of 500 to 700 nanometers. 94. Photochromic objects of claim 86 where a photochromic substance is applied to or incorporated into such photochromic objects by a method of choice from a list of methods including cured molding, insertion into an organic polymer set matrix, and incorporation into a two-component mixture before curing. 95. Photochromic material of claim 86 in which the photochromic material is used by adsorption of the photochromic material to enable the penetration of the photochromic material into the polymerize. 96. The photochromic content of claim 95 in which the absorption process includes a solvent that aids in absorption and transport. 97. The photochromic object of claim 95 in which the absorption process includes the transfer of a vapor phase. 98. Photochromic objects of claim 95 where a photochromic substance is applied as a coating to the surface of a photochromic object. 99. The photochromic material of claim 95 in which the absorption process includes the steps of coating the photochromic material with a photochromic substance, heating the surface of the photochromic material, and removing the residual coating from the surface of the photochromic material. 100. Photochromic objects of claim 86, where photochromic objects are lenses used on the eye for the correction of visual impairments. 101. A photochromic object of claim 59 in which a polycyanate monomer contains one or more sulfur atoms in its structure. 102. A photochromic object of claim 101 in which a polycyanate monomer containing one or more sulfur atoms in its structure has the following general structure (chemical formula) in which R10 and R11 are independent of each other, i.e., C1 to C3 alkyl. 103. A polymerize of claim 31 where a polycyanate monomer containing one or more sulfur atoms in its structure has the following general structural formula (chemical formula) where R10 and R11 are independent, i.e., C1 to C3 alkyl (Clause 103, page 31, 0 figures).