IP Library Granted Patent US 10,723,877
Granted Patent B2
US 10,723,877 · App. 16/303,393 · Granted Jul 28, 2020

Copolycarbonate lenses, methods of manufacture, and applications thereof

Inventors: Mark Adrianus Johannes Van Der Mee (Breda, NL); Nathalie Gonzalez Vidal (Bergen op Zoom, NL); Fabrizio Micciche (Breda, NL); Roland Sebastian Assink (Middelburg, NL); Kazuhiko Mitsui (Moka, JP); Johannes De Brouwer (Oisterwijk, NL); Shahram Shafaei (Bergen op Zoom, NL); Henrikus Petrus Cornelis Van Heerbeek (Bergen op Zoom, NL); Tamara Marijke Eggenhuisen (Breda, NL); Robert Dirk Van De Grampel (Tholen, NL)
Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
C08L69/00C08G64/12C08K5/42G02B1/04G02B1/041G02B1/11G02B1/14C08L2201/08C08L2205/025C08L2205/03
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Quick Facts
Patent No.
US 10,723,877
App. No.
16/303,393
Granted
Jul 28, 2020
Kind
B2
Abstract

A lens containing a polycarbonate composition is disclosed. The polycarbonate composition includes a copolycarbonate having bisphenol A carbonate units and second carbonate units of the formula and 2 to 40 ppm of an organosulfonic stabilizer of the formula 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. 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 (66)

1. A copolycarbonate lens comprising a polycarbonate composition comprising:

a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula

wherein

R a and R b are each independently a C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R 3 is independently a C 1-6 alkyl,

R 4 is hydrogen, C 2-6 alkyl or phenyl optionally substituted with 1 to 5 C 1-6 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 R 7 is independently a C 1-30 alkyl, C 6-30 aryl, C 7-30 alkylarylene, C 7-30 arylalkylene, or a polymer unit derived from a C 2-32 ethylenically unsaturated aromatic sulfonic acid or its ester, and

R 8 is C 1-30 alkyl; or R 8 is a group of the formula —S(═O) 2 —R 7 ;

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.

2. 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.

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

4. 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.

5. The copolycarbonate lens of claim 4 , 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.

6. 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.

7. The copolycarbonate lens of claim 6 , 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.

8. The copolycarbonate lens of claim 1 , wherein the second carbonate repeating units in the copolycarbonate are of the formula

wherein R 5 is hydrogen, phenyl or methyl.

9. 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.

10. 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

R c and R d are each independently a C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R 6 is independently C 1-3 alkyl or phenyl,

X a is a C 6-12 polycyclic aryl, C 3-18 mono- or polycycloalkylene, C 3-18 mono- or polycycloalkylidene, -(Q 1 ) x -G-(Q 2 ) y - group wherein Q 1 and Q 2 are each independently a C 1-3 alkylene, G is a C 3-10 cycloalkylene, x is 0 or 1, and y is 1, or —C(P 1 )(P 2 )— wherein P 1 is C 1-12 alkyl and P 2 is C 6-12 aryl, and

m and n are each independently 0 to 4.

11. The copolycarbonate lens of claim 1 , wherein in the organosulfonic stabilizer each R 7 is independently a C 6-12 aryl, C 7-24 alkylarylene, or a polymer unit derived from a C 2-14 ethylenically unsaturated aromatic sulfonic acid or its C 1-30 alkyl ester; and R 8 is C 1-24 alkyl, or a group of the formula —S(═O) 2 —R 7 wherein R 7 is a C 6-12 aryl or C 7-24 alkylarylene.

12. The copolycarbonate lens of claim 1 , wherein in the organosulfonic stabilizer

R 7 is a C 6-12 aryl, C 7-24 alkylarylene, or a polymer unit derived from a C 2-14 ethylenically unsaturated aromatic sulfonic acid or its ester; and R 8 is C 1-24 alkyl, or a group of the formula —S(═O) 2 —R 7 wherein R 7 is a C 6-12 aryl or C 7-24 alkylarylene; or

R 7 is a C 7-10 alkylarylene or a polymer unit derived from a C 2-14 ethylenically unsaturated aromatic sulfonic acid, and R 8 is a C 1-25 alkyl, or a group of the formula —S(═O) 2 —R 7 wherein R 7 is a C 7-10 alkylarylene; or

R 7 is a polymer unit derived from a C 2-14 ethylenically unsaturated aromatic sulfonic acid; or

R 7 is a C 1-10 alkyl ester of a C 7-12 alkylarylene sulfonic acid; or

R 7 is a group of the formula —S(═O) 2 —R 1 wherein R 1 is a C 6-12 aryl or C 7-24 alkylarylene, preferably a C 7-10 alkylarylene.

13. 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.

14. 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.

15. The copolycarbonate lens of claim 1 , comprising:

a copolycarbonate comprising bisphenol A carbonate units and second carbonate units of the formula

wherein R 5 is hydrogen, phenyl, or methyl,

optionally a bisphenol A homopolycarbonate; and

2 to 20 ppm of an organosulfonic stabilizer comprising a C 1-30 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.

16. 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 R 5 is hydrogen, phenyl or methyl;

25 to 40 wt % of a bisphenol A homopolycarbonate; and

2 to 20 ppm of an organosulfonic stabilizer comprising a C 1-30 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.

17. 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 R 5 is hydrogen, phenyl or methyl; and

2 to 20 ppm of an organosulfonic stabilizer comprising a C 1-30 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.

18. 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.

19. 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.

20. 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.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE REMOVE THE APPLICATION NUMBER 15039474 PREVIOUSLY RECORDED AT REEL: 054528 FRAME: 0467. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 23, 2021
From: SABIC GLOBAL TECHNOLOGIES B.V.
To: SHPP GLOBAL TECHNOLOGIES B.V.
Reel/Frame 057453/0680 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2020
From: SABIC GLOBAL TECHNOLOGIES B.V.
To: SHPP GLOBAL TECHNOLOGIES B.V.
Reel/Frame 054528/0467 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2018
From: VAN DER MEE, MARK ADRIANUS JOHANNES; GONZALEZ VIDAL, NATHALIE; MICCICHE, FABRIZIO; ASSINK, ROLAND SEBASTIAN; MITSUI, KAZUHIKO; DE BROUWER, JOHANNES; SHAFAEI, SHAHRAM; VAN HEERBEEK, HENDRIKUS PETRUS CORNELIS; EGGENHUISEN, TAMARA MARIJKE; VAN DE GRAMPEL, ROBERT DIRK
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 047562/0358 →