IP Library Granted Patent US 12,312,429
Granted Patent B2
US 12,312,429 · App. 17/896,691 · Granted May 27, 2025

Acid-functionalized copolymers of methyl methacrylate and acrylic resin compositions based thereon

Inventors: Jiaxin Jason Ge (Lower Providence, PA); Noah E. Macy (Royersford, PA); Florence Mehlmann (Berwyn, PA); Estelle Meurice Pierrat (Corneville sur-Risle, FR)
Assignee: Trinseo Europe GmbH
C08F220/14C08F220/06C08F220/08C08F301/00C08K5/005C08K5/3492C08K5/49C08L33/12C08F220/1802C08F220/1804C08L2201/10C08L2205/02
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Quick Facts
Patent No.
US 12,312,429
App. No.
17/896,691
Granted
May 27, 2025
Kind
B2
Abstract

Acid-functionalized copolymers of methyl methacrylate having relatively high glass transition temperatures and molecular weights may be employed to manufacture articles having high light transmission values, low haze, high heat resistance, and high environmental stability, which are useful as optical protection films, zero-zero optical retardation films, and compensation films as well as lighting pipes and optical imaging lenses.

Claims (22)

1. An acrylic resin composition comprising:

a copolymer of methyl methacrylate and methacrylic acid, the copolymer having a weight average molecular weight of at least 60,000 g/mole and a glass transition temperature of at least 115° C., wherein methyl methacrylate comprises from 70 to 99 weight % of the copolymer;

a polymer of

methyl methacrylate,

methacrylic acid,

ethyl acrylate or n-butyl acrylate, and

styrene or α-methylstyrene;

the polymer having a weight average molecular weight of at least 60,000 g/mole and a glass transition temperature of at least 115° C.; and

an additional polymer of methyl methacrylate and one or more C 1 -C 4 alkyl esters of acrylic acid, wherein the additional polymer has a weight average molecular weight of at least 130,000 g/mole.

2. The acrylic resin composition of claim 1 , wherein the copolymer has a weight average molecular weight of at least 80,000 g/mole.

3. The acrylic resin composition of claim 1 , wherein the copolymer has a weight average molecular weight of at least 100,000 g/mole.

4. The acrylic resin composition of claim 1 , wherein the copolymer has a glass transition temperature of at least 120° C.

5. The acrylic resin composition of claim 1 , wherein the copolymer has a refractive index of 1.45-1.53 at a wavelength of 589 nm.

6. The acrylic resin composition of claim 1 , wherein the methacrylic acid of the copolymer comprises from 1 to 7 weight % of the copolymer.

7. The acrylic resin composition of claim 1 , wherein the methyl methacrylate of the copolymer comprises from 79 to 99 weight % of the copolymer.

8. The acrylic resin composition of claim 1 , wherein the copolymer has a light transmission of at least about 88%, and less than 10% haze when measured by ASTM D1003 on a 3.2 mm thick plaque.

9. The acrylic resin composition of claim 1 , wherein the copolymer has a melt flow rate of about 0.3 to about 2.5 g/10 minutes at 230° C. under 3.8 kg.

10. The acrylic resin composition of claim 1 , wherein the acrylic resin composition further comprises at least one additive selected from the group consisting of antioxidant, UV stabilizer, and toughening agent.

11. The acrylic resin composition of claim 10 , wherein the at least one antioxidant is selected from the group consisting of phosphite antioxidants, phosphate antioxidants, phosphonate antioxidants, phosphine antioxidants, phenolic antioxidants, triazinetrione antioxidants and combinations thereof.

12. The acrylic resin composition of claim 10 , wherein the at least one UV stabilizer is selected from the group consisting of benzophenone UV stabilizers, benzotriazole UV stabilizers, hydroxyphenyl benzotriazole UV stabilizers, hydroxyphenyl triazine UV stabilizers, benzoxazinone UV stabilizers and combinations thereof.

13. The acrylic resin composition of claim 10 , wherein the at least one toughening agent is selected from the group consisting of block copolymer toughening agents and core-shell toughening agents.

14. The acrylic resin composition of claim 1 , wherein the additional polymer is a copolymer of methyl methacrylate and at least one comonomer selected from ethyl acrylate or methyl acrylate.

Assignments (5)
SECURITY INTEREST Recorded Jan 29, 2025
From: TRINSEO EUROPE GMBH
To: ALTER DOMUS (US) LLC
Reel/Frame 070048/0159 →
SECURITY INTEREST Recorded Jan 29, 2025
From: TRINSEO EUROPE GMBH
To: ALTER DOMUS (US) LLC
Reel/Frame 070048/0204 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2023
From: ARKEMA FRANCE
To: TRINSEO EUROPE GMBH
Reel/Frame 065494/0359 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2023
From: TRINSEO EUROPE GMBH
To: TRINSEO EUROPE GMBH
Reel/Frame 065494/0396 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2023
From: GE, JIAXIN JASON; MACY, NOAH E.; MEHLMANN, FLORENCE; PIERRAT, ESTELLE MEURICE
To: ARKEMA FRANCE
Reel/Frame 063855/0333 →
Continuity (3)
Continuation 16484837
Provisional Application 62461009 · Feb 20, 2017
Related Publication 20220411552A1 · Dec 29, 2022
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