Indane bisphenols, polymers derived therefrom, and methods of use thereof
View Patent ↗Indane bisphenol monomer units, and polymers derived from such monomer units are provided. Also provided are blends including such polymers, articles made from such polymers and blends, methods of using such monomers, polymers, and blends, and processes for preparing such monomers, polymers, and blends.
1. A polymer comprising repeating units of formula (1),
wherein
R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 2 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 3 is hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 4 is hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 5 and R 6 , at each occurrence, are each independently halogen, C 1 -C 6 alkyl, or C 3 -C 8 cycloalkyl; and
x and y, at each occurrence, are each independently 0, 1, 2, 3, or 4;
wherein the polymer further comprises:
(i) repeating units derived from one or more monomers having the structure HO-A 1 -Y 1 -A 2 -OH wherein each of A 1 and A 2 comprise a monocyclic divalent arylene group, and Y 1 is a bridging group having one or more atoms;
(ii) repeating units derived from one or more monomers having the structure
wherein each R h is independently a halogen atom, a C 1 -C 10 hydrocarbyl, or a halogen substituted C 1 -C 10 hydrocarbyl, and n is 0 to 4; or
(iii) one or more polyester repeating units having the structure
wherein D comprises one or more alkyl containing C 6 -C 20 aromatic group(s), or one or more C 6 -C 20 aromatic group(s), and T comprises a C 6 -C 20 aromatic group;
wherein the repeating units of (i), (ii), and (iii) are different from the repeating units of formula (1).
2. The polymer of claim 1 , wherein the repeating units of formula (1) are derived from a monomer of formula (II),
3. The polymer of claim 1 , wherein the polymer is free of halogen atoms.
4. The polymer of claim 1 , comprising an end cap group, wherein at least one end cap group is derived from p-cumylphenol, t-butylphenol, 4-hydroxybenzonitrile, or phenol.
5. The polymer of claim 1 , having a weight average molecular weight ranging from about 15,000 to about 50,000 g/mol [ ± 1,000 g/mol].
6. The polymer of claim 1 , having a polydispersity ranging from about 2.0 to about 7.0.
7. The polymer of claim 1 , having a glass transition temperature ranging from about 150° C. to about 220° C.
8. The polymer of claim 1 , comprising repeating units derived from 2,2-bis(4-hydroxyphenyl)propane (bisphenol-A).
9. The polymer of claim 1 , wherein the polymer comprises more than 15 mole percent repeating units of formula (1).
10. The polymer of claim 1 , wherein the polymer comprises more than 15 mole percent repeating units of formula (1), and the remainder of the structural units are derived from 2,2 bis(4-hydroxyphenyl)propane (bisphenol-A).
11. The polymer of claim 1 , made by a melt process or an interfacial polymerization process.
12. An article comprising the polymer of claim 1 .
13. The article of claim 12 , wherein the article has a glass transition temperature (Tg) of at least 160° C.
14. The article of claim 12 , selected from at least one of the following: automotive bumpers, other automotive exterior components, automobile mirror housings, automobile wheel covers, automobile instrument panels and trim, automobile glove boxes, automobile door hardware and other interior trim, automobile exterior lights, automobile parts within the engine compartment, plumbing equipment, valves and pumps, air conditioning heating and cooling parts, furnace and heat pump parts, computer parts, electronics parts, projector parts, electronic display parts, copier parts, scanner parts, electronic printer toner cartridges, hair driers, irons, coffee makers, toasters, washing machines, microwaves, ovens, power tools, electric components, lighting parts, dental instruments, medical instruments, cookware, medical instrument trays, animal cages, fibers, laser welded medical devices, fiber optics, lenses (auto and non-auto), cell phone parts, greenhouse components, sun room components, and fire helmets.
15. A blend composition, comprising:
(i) a first polymer (A) containing repeating units derived from a monomer of formula (I),
wherein
R 1 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 2 is C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 3 is hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 4 is hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, aryl, or arylalkyl;
R 5 and R 6 , at each occurrence, are each independently halogen, C 1 -C 6 alkyl, or C 3 -C 8 cycloalkyl; and
x and y, at each occurrence, are each independently 0, 1, 2, 3, or 4; and
(ii) a second polymer (B) which is different from polymer (A).
16. The blend composition of claim 15 , wherein the monomer of formula (I) is 4,4′-(3,3-dimethyl-2,2-dihydro-1H-indene-1,1-diyl)diphenol.
17. The blend composition of claim 15 , wherein polymer (A) is a copolycarbonate of 4,4′-(3,3-dimethyl-2,2-dihydro-1H-indene-1,1-diyl)diphenol and bisphenol-A.
18. The blend composition of claim 15 , wherein polymer (B) is derived from monomer units other than monomer units of formula (I).
19. The blend composition of claim 15 , wherein polymer (B) is selected from at least one of the following: a vinyl polymer, a rubber-modified graft copolymer, an acrylic polymer, polyacrylonitrile, a polystyrene, a polyolefin, a polyester, a polyesteramide, a polysiloxane, a polyurethane, a polyamide, a polyamideimide, a polysulfone, a polyepoxide, a polyether, a polyimide, a polyetherimide, a polyphenylene ether, a polyphenylene sulfide, a polyether ketone, a polyether ether ketone, an ABS resin, an ASA resin, a polyethersulfone, a polyphenylsulfone, a poly(alkenylaromatic) polymer, a polybutadiene, a polyacetal, a polycarbonate, a polyphenylene ether, an ethylene-vinyl acetate copolymer, a polyvinyl acetate, a liquid crystal polymer, an ethylene-tetrafluoroethylene copolymer, an aromatic polyester, a polyvinyl fluoride, a polyvinylidene fluoride, a polyvinylidene chloride, tetrafluoroethylene, a polylactide, a polylactic acid (PLA), a polycarbonate-polyorganosiloxane block copolymer, and a copolymer comprising: (i) an aromatic ester, (ii) an estercarbonate, and (iii) carbonate repeat units.
20. The blend composition of any one of claim 15 , further comprising at least one additive.
21. The blend composition of claim 20 , wherein the additive is an impact modifier selected from at least one of the following: polycarbonate-polysiloxane copolymers, acrylonitrile-butadiene-styrene (ABS) polymers, methacrylate-butadiene-styrene (MBS) polymers, and acrylate polymers.
22. The blend composition of claim 21 , wherein the impact modifier is a polycarbonate-polysiloxane copolymer.
23. The blend composition of claim 21 , wherein the impact modifier is a combination of a polycarbonate-polysiloxane copolymer and an acrylate polymer.
24. The blend composition of claim 20 , wherein the additive is a UV stabilizer selected from 2-(2′-hydroxyphenyl)-benzotriazoles.
25. The blend composition of claim 24 , wherein the UV stabilizer is 2-(2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenyl-ethyl)phenol.
26. An article comprising the blend composition of claim 15 .
27. The article of claim 26 , selected from at least one of the following: automotive bumpers, other automotive exterior components, automobile mirror housings, automobile wheel covers, automobile instrument panels and trim, automobile glove boxes, automobile door hardware and other interior trim, automobile exterior lights, automobile parts within the engine compartment, plumbing equipment, valves and pumps, air conditioning heating and cooling parts, furnace and heat pump parts, computer parts, electronics parts, projector parts, electronic display parts, copier parts, scanner parts, electronic printer toner cartridges, hair driers, irons, coffee makers, toasters, washing machines, microwaves, ovens, power tools, electric components, lighting parts, dental instruments, medical instruments, cookware, medical instrument trays, animal cages, fibers, laser welded medical devices, fiber optics, lenses (auto and non-auto), cell phone parts, greenhouse components, sun room components, and fire helmets.
28. The composition of claim 1 , wherein R 1 is methyl; R 2 is methyl; R 3 is hydrogen; R 4 is hydrogen; x is 0; and y is 0.
29. The polymer of claim 1 , wherein the polymer comprises about 15 mole percent to about 85 mole percent of repeating units of formula (1).
30. The polymer of claim 1 , wherein the polymer comprises about 55 mole percent or greater of repeating units of formula (1).
31. The polymer of claim 1 , having a glass transition temperature ranging from about 170° C. to about 220° C.