# US 2019/0169368 A1 · Copolycarbonate lenses, methods of manufacture, and applications thereof

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- Number: US 2019/0169368 A1
- Document ID: US20190169368A1
- Status: Published application
- Kind: A1
- Application number: 16/303,393
- Filed: 2017-05-27
- Published: 2019-06-06
- Earliest claimed: 2016-05-27
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: MARK ADRIANUS JOHANNES VAN DER MEE; NATHALIE GONZALEZ VIDAL; FABRIZIO MICCICHE; ROLAND SEBASTIAN ASSINK; KAZUHIKO MITSUI; JOHANNES DE BROUWER; SHAHRAM SHAFAEI; HENDRIKUS PETRUS CORNELIS VAN HEERBEEK; TAMARA MARIJKE EGGENHUISEN; ROBERT DIRK VAN DE GRAMPEL
- Web page: https://patentgrep.com/patent/US20190169368A1

## CPC

- C08L 69/00: Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C08G 64/12: containing nitrogen
- C08K 5/42: Sulfonic acids; Derivatives thereof
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 1/041: {Lenses}
- G02B 1/11: Anti-reflection coatings
- G02B 1/14: Protective coatings, e.g. hard coatings
- C08L 2201/08: Stabilised against heat, light or radiation or oxydation
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C08L 2205/03: containing three or more polymers in a blend
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

A lens comprising a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula (I) and 2 to 40 ppm of an organosulfonic stabilizer of the formula (II), wherein the second carbonate units are present in an amount of 20 to 49 mol %, preferably 30 to 40 mol % based on the sum of the moles of the copolycarbonate and the bisphenol A homopolycarbonate; and the polycarbonate composition has: a Vicat B120 of 160° C. or higher measured according to ISO 306; and a yellowness index of less than 12, measured according to ASTM D1925.

## Claims

### Claim 1

A copolycarbonate lens comprising a polycarbonate composition comprising:
a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula
wherein
Ra and Rb are each independently a C1-12 alkyl, C1-12 alkenyl, C3-8 cycloalkyl, or C1-12 alkoxy,
each R3 is independently a C1-6 alkyl,
R4 is hydrogen, C2-6 alkyl or phenyl optionally substituted with 1 to 5 C1-6 alkyl groups,
p, q, and j are each independently 0 to 4,
optionally a bisphenol A homopolycarbonate; and
2 to 40 ppm of an organosulfonic stabilizer of the formula
wherein
each R7 is independently a C1-30 alkyl, C6-30 aryl, C7-30 alkylarylene, C7-30 arylalkylene, or a polymer unit derived from a C2-32 ethylenically unsaturated aromatic sulfonic acid or its ester, and
R8 is hydrogen; or R8 is C1-30 alkyl; or R8 is a group of the formula —S(═O)2—R7;
wherein the second carbonate units are present in an amount of 20 to 49 mol % based on the sum of the moles of the copolycarbonate and the bisphenol A homopolycarbonate; and
wherein the polycarbonate composition has:
a Vicat B120 of 160° C. or higher measured according to ISO 306; and
a yellowness index of less than 12, measured according to ASTM D1925 on a plaque of 2.5 mm thickness molded at a temperature of 355° C. for a residence time of 10 minutes.

### Claim 2 (depends on 1)

The copolycarbonate lens of claim 1, wherein the lens is a planar lens, a curved lens, a cylindrical lens, a toric lens, a sphero-cylindrical lens, a fresnel lens, a convex lens, a biconvex lens, a concave lens, a biconcave lens, a convex-concave lens, a plano-convex lens, a plano-concave lens, a lenticular lens, a gradient index lens, an axicon lens, a conical lens, an astigmatic lens, an aspheric lens, a corrective lens, a diverging lens, a converging lens, a compound lens, a photographic lens, a doublet lens, a triplet lens, an achromatic lens, or a multi-array lens.

### Claim 3 (depends on 1)

The copolycarbonate lens of claim 1, further comprising a macrotexture, a microtexture, a nanotexture, or a combination thereof on a surface of the lens.

### Claim 4

(canceled)

### Claim 5 (depends on 1)

The copolycarbonate lens of claim 1, further comprising an indicia or a coating disposed on at least a portion of one or both surfaces of the copolycarbonate lens.

### Claim 6 (depends on 5)

The copolycarbonate lens of claim 5, wherein the coating is a hard coat, a UV protective coat, an anti-refractive coat, an anti-reflective coat, a scratch resistant coat, or a combination comprising at least one of the foregoing, or wherein at least a portion of a surface of the lens is metallized.

### Claim 7 (depends on 1)

The copolycarbonate lens of claim 1, wherein the copolycarbonate lens is a camera lens, a sensor lens, an illumination lens, a safety glass lens, an ophthalmic corrective lens, or an imaging lens.

### Claim 8 (depends on 7)

The copolycarbonate lens of claim 7, wherein
the camera lens is a mobile phone camera lens, a table camera lens, a security camera lens, a mobile phone camera lens, a tablet camera lens, a laptop camera lens, a security camera lens, a camera sensor lens, or a vehicle camera lens,
the sensor lens can be a motion detector lens, a proximity sensor lens, a gesture control lens, an infrared sensor lens, or a camera sensor lens,
the illumination lens is an indoor lighting lens, an outdoor lighting lens, vehicle headlamp lens, a vehicle foglight lens, a vehicle rearlight lens, a vehicle running light lens, a vehicle foglight lens, a vehicle interior lens, an a light emitting diode lens, or an organic light emitting diode lens,
the safety glass lens is a glasses lens, a goggles lens, a visor, or a helmet lens,
the ophthalmic corrective lens is a monocle lens, a corrective glasses lens, or a contact lens, or
the imaging lens is a scanner lens, a projector lens, a magnifying glass lens, a microscope lens, a telescope lens, a security lens, or a reading glasses lens,

### Claim 9 (depends on 1)

The copolycarbonate lens of claim 1, wherein the second carbonate repeating units in the copolycarbonate are of the formula
wherein R5 is hydrogen, phenyl or methyl.

### Claim 10

(canceled)

### Claim 11 (depends on 1)

The copolycarbonate lens of claim 1, wherein the copolycarbonate comprises from 50 to 90 mole percent of the bisphenol A carbonate units and 10 to 50 mole percent of the second carbonate units, and has less than 15 mole percent of the second carbonate units directly coupled to another second carbonate unit, each based on the total number of carbonate units in the copolycarbonate.

### Claim 12 (depends on 1)

The copolycarbonate lens of claim 1, wherein the copolycarbonate further comprises at least 5 mole percent of a third carbonate unit different from the bisphenol A carbonate units and the second carbonate units, the third carbonate unit comprising units of the formula
or a combination thereof, wherein
Rc and Rd are each independently a C1-12 alkyl, C1-12 alkenyl, C3-8 cycloalkyl, or C1-12 alkoxy,
each R6 is independently C1-3 alkyl or phenyl,
Xa is a C6-12 polycyclic aryl, C3-18 mono- or polycycloalkylene, C3-18 mono- or polycycloalkylidene, -(Q1)x-G-(Q2)y- group wherein Q1 and Q2 are each independently a C1-3 alkylene, G is a C3-10 cycloalkylene, x is 0 or 1, and y is 1, or —C(P1)(P2)— wherein P1 is C1-12 alkyl and P2 is C6-12 aryl, and
m and n are each independently 0 to 4.

### Claim 13

(canceled)

### Claim 14

(canceled)

### Claim 15 (depends on 1)

The copolycarbonate lens of claim 1, wherein in the organosulfonic stabilizer each R7 is independently a C6-12 aryl, C7-24 alkylarylene, or a polymer unit derived from a C2-14 ethylenically unsaturated aromatic sulfonic acid or its C1-30 alkyl ester; and R8 is hydrogen, C1-24 alkyl, or a group of the formula —S(═O)2—R7 wherein R7 is a C6-12 aryl or C7-24 alkylarylene.

### Claim 16 (depends on 1)

The copolycarbonate lens of claim 1, wherein in the organosulfonic stabilizer
R7 is a C6-12 aryl, C7-24 alkylarylene, or a polymer unit derived from a C2-14 ethylenically unsaturated aromatic sulfonic acid or its ester; and R8 is hydrogen, C1-24 alkyl, or a group of the formula —S(═O)2—R7 wherein R7 is a C6-12 aryl or C7-24 alkylarylene; or
R7 is a C7-10 alkylarylene or a polymer unit derived from a C2-14 ethylenically unsaturated aromatic sulfonic acid, and R8 is a hydrogen, C1-25 alkyl, or a group of the formula —S(═O)2—R7 wherein R7 is a C7-10 alkylarylene; or
R7 is a polymer unit derived from a C2-14 ethylenically unsaturated aromatic sulfonic acid; or
R7 is a C1-10 alkyl ester of a C7-12 alkylarylene sulfonic acid; or
R7 is a group of the formula —S(═O)2—R1 wherein R7 is a C6-12 aryl or C7-24 alkylarylene, preferably a C7-10 alkylarylene.
R7 is a C11-24 alkylarylene sulfonic acid, and R7 is hydrogen.

### Claim 17 (depends on 1)

The copolycarbonate lens of claim 1, wherein the stabilizer is present in an amount of 2 ppm to 20 ppm based on the total weight of the polycarbonate composition.

### Claim 18 (depends on 1)

The copolycarbonate lens of claim 1, wherein the polycarbonate composition has a bisphenol A purity of equal to or greater than 99.6%, measured by high performance liquid chromatography.

### Claim 19

(canceled)

### Claim 20 (depends on 1)

The copolycarbonate lens of claim 1, comprising:
a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula
wherein R5 is hydrogen, phenyl, or methyl,
optionally a bisphenol A homopolycarbonate; and
2 to 20 ppm of an organosulfonic stabilizer comprising a C1-30 alkyl ester of p-toluenesulfonic acid;
wherein the polycarbonate composition has 25 mol % to 49 mol % of second carbonate units based on the sum of the moles of the copolycarbonate and the bisphenol A homopolycarbonate.

### Claim 21 (depends on 1)

The copolycarbonate lens of claim 1, comprising, based on the total weight of the polycarbonate composition:
60 to 70 wt % of a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula
wherein R5 is hydrogen, phenyl or methyl;
25 to 40 wt % of a bisphenol A homopolycarbonate; and
2 to 20 ppm of an organosulfonic stabilizer comprising p-toluenesulfonic acid, a C1-30 alkyl ester of p-toluenesulfonic acid or a combination thereof;
wherein the polycarbonate composition has 25 mol % to 49 mol % of second carbonate units based on the sum of the moles of the copolycarbonate and the bisphenol A homopolycarbonate.

### Claim 22 (depends on 1)

The copolycarbonate lens of claim 1, comprising, based on the total weight of the polycarbonate composition:
96 to 99.9 wt % of a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula
wherein R5 is hydrogen, phenyl or methyl; and
2 to 20 ppm of an organosulfonic stabilizer comprising a C1-30 alkyl ester of p-toluenesulfonic acid;
wherein the polycarbonate composition has 25 mol % to 49 mol % of second carbonate units based on the moles of the copolycarbonate.

### Claim 23

(canceled)

### Claim 24 (depends on 1)

The copolycarbonate lens of claim 1, wherein the copolycarbonate has a hydroxyl end group content of less than 200 ppm and the optional bisphenol A homopolycarbonate has a hydroxyl end group content of less than 150 ppm.

### Claim 25 (depends on 1)

The copolycarbonate lens of claim 1, wherein the copolycarbonate, the optional bisphenol A homopolycarbonate, or both are derived from a bisphenol A having a sulfur content of less than 2 ppm, each as measured by a Total Sulfur Analysis based on combustion and coulometric detection.

### Claim 26

(canceled)

### Claim 27 (depends on 1)

A device comprising the copolycarbonate lens of claim 1, wherein the device is a camera, an electronic device, a vehicle, a flashlight, a business machine, a lighting device, an imaging device, a protective article, a vision corrective article, or a toy.