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

Patent metadata

Field	Value
Publication number	US-10640645-B2
Application number	US-201716093282-A
Country	US
Kind code	B2
Filing date	Apr 14, 2017
Priority date	Apr 15, 2016
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

A polymer composition that includes, 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, preferably 5-100 mole percent, of isoindolinone ether ketone units of the formula (I) and 0-99 mole percent, of arylene ether ketone units of the formula (II) wherein the variables are as defined herein.

First claim

What is claimed is:

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,

Assignees

• Sabic Global Technologies Bv
• Sabic Global Tech

Inventors

• Patil Dadasaheb V
• Sista Prakash
• Gallucci Robert Russell

Classifications

• C08G65/4037

  in ring structure, e.g. pyridine group · CPC title

• C08G2650/40

  containing ketone groups, e.g. polyarylethylketones, PEEK or PEK · CPC title

• B29K2105/06

  containing reinforcements, fillers or inserts · CPC title

• C08G65/4031

  (I) or (II) containing nitrogen · CPC title

• B29C48/022

  characterised by the choice of material · CPC title