Polycarbonates
View Patent ↗Polycarbonates made from polyhydric phenols that preferably exhibit estrogenic activity less than bisphenol S exhibit properties such as high impact strengths, moderate to high glass transition temperatures, chemical resistance, and good color and clarity similar to conventional BPA-derived polycarbonates.
1. A food contact or beverage contact polycarbonate article comprising a polycarbonate comprising a reaction product of a polyhydric phenol and a carbonate precursor, wherein the polyhydric phenol comprises:
a polyhydric phenol having two aryl or heteroaryl groups in which each aryl or heteroaryl group includes a hydroxyl group attached to the ring and at least one methyl substituent group attached to the ring at an ortho position relative to the hydroxyl group and wherein the substituent group is free of halogen; and the aryl or heteroaryl groups are joined through a methylene group; and
the polycarbonate is substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S.
2. The article of claim 1 , wherein each aryl or heteroaryl group includes a two methyl substituent groups attached to the ring at the ortho positions relative to the hydroxyl group.
3. The article of claim 1 , wherein the polycarbonate contains one or more segments of Formula (I):
wherein:
each of the oxygen atoms depicted in Formula (I) is part of a carbonate linkage;
H denotes a hydrogen atom, if present;
each R 1 is independently an atom or group having an atomic weight of at least 15 Daltons and at least one R 1 group is a methyl group attached to the phenylene ring at an ortho position relative to the oxygen atom;
v is independently 1 to 4;
w is 4;
R 2 is a divalent methylene group;
n is 1;
t is 1; and
the polycarbonate is substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S.
4. The article of claim 3 , wherein each of the phenylene groups depicted in Formula (I) includes at least one R 1 methyl group attached to the phenylene ring at an ortho position relative to the oxygen atom.
5. The article of claim 3 , wherein R 1 methyl groups are attached to the phenylene ring at both ortho positions relative to the oxygen atom.
6. The article of claim 3 , wherein an R 1 group independently comprises an ethyl group attached to the phenylene ring at an ortho position relative to the oxygen atom.
7. The article of claim 3 , wherein a width measured perpendicular from a centerline of the phenylene ring to the maximal outside extent of the van der Waals volume of R 1 is greater than about 4.5 Angstroms.
8. The article of claim 3 , wherein each R 1 group is free of halogen atoms.
9. The article of claim 3 , wherein:
the oxygen atom of each phenylene group depicted in Formula (I) is located at a para position relative to R 2 .
10. The article of claim 3 , wherein the segment of Formula (I) is derived from 4,4′-methylenebis(2,6-dimethylphenol).
11. The article of claim 1 , wherein the polyhydric phenol or derivative thereof exhibits a log Relative Proliferative Effect value in an MCF-7 cell proliferation assay less than that of bisphenol S.
12. The article of claim 1 , wherein the polycarbonate comprises a layer in a monolayer or multilayer article.
13. The article of claim 1 , wherein the article is a baby bottle, sports bottle, water bottle, mug, jug or glass.
14. The article of claim 1 , wherein the article is selected from food packaging, cookware, cutlery, tableware, and food processing machinery and equipment.
15. A method of making a food contact or beverage contact article comprising a polycarbonate polymer, comprising:
reacting a carbonate precursor and a polyhydric phenol of Formula (II):
wherein:
H denotes a hydrogen atom, if present;
each R 1 is independently an atom or group having an atomic weight of at least 15 Daltons and at least one R 1 group is a methyl group attached to the phenylene ring at an ortho position relative to the oxygen atom;
v is independently 1 to 4;
w is 4;
R 2 is a divalent methylene group;
n is 1;
t is 1; and
the polycarbonate is substantially free of polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S.
16. The method of claim 15 , further comprising forming the polycarbonate polymer into a food or beverage contact surface of such article by molding, film or sheet formation, lamination or coating.
17. The method of claim 15 , wherein each of the phenylene groups depicted in Formula (II) includes at least one R 1 methyl group attached to the phenylene ring at an ortho position relative to the hydroxyl group.
18. The method of claim 15 , wherein R 1 methyl groups are attached to the phenylene ring at both ortho positions relative to the hydroxyl group.
19. The method of claim 15 , wherein an R 1 group independently comprises an ethyl group attached to the phenylene ring at an ortho position relative to the hydroxyl group.
20. The method of claim 15 , wherein each R 1 group is free of halogen atoms.
21. The article of claim 1 , wherein the carbonate precursor comprises a carbonyl halide, carbonate ester derived from mono-functional alcohols or phenols or mixtures thereof, or bishaloformate.