Polyisoindolinone compositions, methods of manufacture, and compositions and articles formed therefrom

1. A polymer composition comprising, based on the total weight of the polymers:

1-99 weight percent of a polymer component comprising a polyarylether ketone, a polybenzimdazole, a polyimide, a poly(aryl ether sulfone), a poly(phenylene sulfide), or a combination comprising at least one of the foregoing; and

1-99 weight percent of a polyisoindolinone, wherein the polyisoindolinone comprises:

1-100 mole percent of isoindolinone ether ketone units of the formula

wherein

each R 1 is independently the same or different, and is hydrogen, C 1-8 alkyl, C 3-8 cycloalkyl, or phenyl optionally substituted with 1-5 C 1-6 alkyl groups,

each R a is independently the same or different, and is C 1-6 alkyl,

each R b is independently the same or different, and is C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each R c is independently the same or different, and is C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each p, q, and r is independently the same or different, and is an integer of 0-4, and

x is an integer of 1-4; and

0-99 mole percent of arylene ether ketone units of the formula

wherein

each R 2 is independently the same or different, and is a C 6-30 substituted or unsubstituted arylene,

each R c is independently the same or different, and is C 1-12 alkyl, C 2-12 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy,

each r is independently the same or different, and is an integer of 0-4, and

x is an integer of 1-4; and

wherein when the polyisoindolinone is a poly(isoindolinone ether ether ketone), it has a least one of the following properties:

a glass transition temperature greater than 150° C. as determined by differential scanning calorimetry, or

less than 25 weight percent solubility at 23° C. in dichloromethane, orthodichlorobenzene, or chloroform.

2. The polymer composition of claim 1 , wherein the composition has at least one of:

a crystallinity of 10 percent or higher, as determined by differential scanning calorimetry; or

less than 20 weight percent solubility at 23° C. in dichloromethane, dichloroethane, or chloroform, when in the form of a melt-pressed film.

3. The polymer composition of claim 1 , wherein

a melt-pressed film of 300 micrometer thickness can be folded 180 degrees greater than 3 times without breaking; or

a melt-pressed film of 300 micrometer-thickness can be folded 180 degrees more than 3 times without breaking after autoclaving for 3 days at 130° C.; or

the polymer composition has a modulus greater than 1000 MPa at 150-300° C., as measured by ASTM D5418, on a 300 micrometer-thick film sample.

4. The polymer composition of claim 1 , wherein

a 300 micrometer-thick molded sample of the polymer composition has at least 70% transmission at 850 nm, 1310 nm, or 1550 nm, as measured on an ultraviolet-visible/near infrared spectrophotometer; or

a 300 micrometer-thick molded sample of the polymer composition has greater than 70% transmission as measured using the color space CIE1931 (Illuminant C and a 2° observer).

5. The polymer composition of claim 1 , wherein the polyarylether ketone is a poly(ether ether ketone), a poly(ether ketone), a poly(ether ketone ketone), a poly(ketone ether ketone ketone), or a combination comprising at least one of the foregoing.

6. The polymer composition of claim 5 , wherein the polyarylether ketone comprises a repeating unit of the formulas

or a combination comprising at least one of the foregoing.

7. The polymer composition of claim 1 , wherein the composition is an immiscible composition that has the following properties:

a crystalline melting point of 300-350° C.,

two glass transitions between 150 and 300° C., or

a modulus at 150 to 300° C. of greater than 300 MPa at a 300 micrometer sample thickness measured according to ASTM D5418.

8. The polymer composition of claim 1 , wherein the composition is a miscible composition that has at least one of the following properties:

no crystalline melting point;

one glass transition temperature between 150 and 300° C.; or

a modulus at 150 to 300° C. of greater than 1,000 MPa at a 300 micrometer sample thickness measured according to ASTM D5418.

9. The polymer composition of claim 1 , wherein the polyisoindolinone further has at least one of the following properties:

less than 25 parts per million by weight of benzylic protons of the polyisoindolinone;

a hydroxyl polymer end group content of less than 700 parts per million by weight of the polyisoindolinone;

a halogen content of less than 900 parts per million by weight of the polyisoindolinone;

a residual alkali or alkaline earth metal cation content of less than 500 parts per million by weight of the polyisoindolinone;

a residual solvent content of less than 500 parts per million by weight of the polyisoindolinone.

10. The polymer composition of claim 1 , wherein the polyisoindolinone further has at least one of the following properties:

a weight average molecular weight of at least 15,000 Daltons;

an onset decomposition temperature of greater than 485° C. as determined using thermogravimetric analysis in nitrogen;

a coefficient of thermal expansion of 30-90 ppm/° C. as determined according to ASTM E831;

greater than 10% crystallinity, as determined using differential scanning calorimetry on the second heat cycle, wherein heating and cooling is at a rate of 20° C./minute for both heating and cooling cycles.

11. The polymer composition of claim 1 , wherein the polyisoindolinone has the following properties:

a 300 micrometer-thick film of the polyisoindolinone has at least 70% transmission at 850 nm, 1310 nm, or 1550 nm as measured on an ultraviolet-visible/near infrared spectrophotometer; or

a 300 micrometer-thick film sample has greater than 70% transmission as measured using the color space CIE1931 (Illuminant C and a 2° observer).

12. The polymer composition of claim 1 , wherein the polyisoindolinone further has at least one of the following properties:

a water uptake of less than 3 percent at 23° C., after 24 hours by direct immersion;

a shift in melt viscosity of less than 30% over 30 min at 380° C. under a nitrogen atmosphere as measured in a small amplitude oscillatory time sweep rheology at a fixed angular frequency of 10 radians/second; or

a char yield of greater than 30 weight percent, as determined using thermogravimetric analysis under inert atmosphere of nitrogen.

13. The polymer composition of claim 1 , wherein a melt-pressed film of the polyisoindolinone can be folded 180 degrees greater than 3 times without breaking after autoclaving for 3 days at 130° C.

14. The polymer compositions of claim 1 , wherein the polyisoindolinone comprises up to 99 mole percent of the arylene ether ketone units.

15. The polymer composition of claim 1 , wherein in the polyisoindolinone

R 2 is a C 6-30 substituted or unsubstituted arylene of the formula

wherein

each R e is independently the same or different, and is C 1-12 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, or C 1-6 alkoxy,

each t is independently the same or different, and is an integer of 0-4,

each u is independently the same or different, and is an integer of 0-4, and

X a is a single bond, —O—, —S—, —S(═O)—, —S(═O) 2 —, —C(═O)—, —P(R)(═O)— wherein R is a C 1-8 alkyl or C 6-12 aryl, or a C 1-18 organic bridging group.

16. The polymer composition of claim 1 , wherein R 2 is derived from a compound that is p-hydroquinone, methyl hydroquinone, dimethyl hydroquinone, tert-butyl hydroquinone, di-tert-butyl hydroquinone, resorcinol, 4,4′-biphenol, 4,4′-dihydroxydiphenyl ether, 4,4′-isopropylidenediphenol, 4,4′-(hexafluoroisopropylidene)diphenol, bis(3,5-dimethyl-4-hydroxyphenyl)isopropylidene, bis(4-hydroxyphenyl) sulfoxide, bis(4-hydroxyphenyl) sulfone, bis(4-hydroxyphenyl) sulfide, bis(3,5-dimethyl-4-hydroxyphenyl) sulfone, 4,4′-(1-phenylethylidene)bisphenol, 4,4′-dihydroxybenzophenone, 1,4-bis-(p-hydroxybenzoyl)benzene, 1,3-bis-(p-hydroxybenzoyl)benzene, or a combination thereof.

17. The polymer composition of claim 1 , wherein

R 1 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, or phenyl optionally substituted with 1-3 C 1-6 alkyl groups;

R a is C 1-4 alkyl;

each R b is independently the same or different, and is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, or C 1-6 alkoxy;

each R c is independently the same or different, and is C 1-6 alkyl, C 2-6 alkenyl, C 3-8 cycloalkyl, or C 1-12 alkoxy;

each R c is independently the same or different, and is C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, or C 1-6 alkoxy;

each p, q, r, and t is independently the same or different, and is an integer of 0 or 1;

each u is independently the same or different, and is 0 or 1; and

each x is independently the same or different, and is an integer of 1-4.

18. The polymer composition of claim 1 , further comprising an additive, a particulate filler, a reinforcing agent, or a combination comprising at least one of the foregoing.

19. An article comprising the polymer composition of claim 1 .

20. A method of forming the article claim 19 , comprising shaping, extruding, molding, or injection molding the polymer composition.