Polymerizable spirobisindane monomers and polymers prepared therefrom

Patent metadata

Field	Value
Publication number	US-9296668-B2
Application number	US-201314430022-A
Country	US
Kind code	B2
Filing date	Sep 12, 2013
Priority date	Sep 25, 2012
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

Monomers and polymerizable compositions that can be polymerized using a free-radical polymerization reaction are provided. The monomers have two vinyl groups as well as a spirobisindane-type structure. Polymers prepared from the polymerizable compositions are also provided. The polymers can be porous.

First claim

I claim:

1. A compound of Formula (I)

wherein
each R1 is independently hydrogen, halo, alkyl, aryl, alkaryl, or aralkyl;
each R2 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R3 connected to a same carbon atom to form a cyclic alkyl, combines with a R3 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, or combines with R3 and the carbon atom to which both R2 and R3 are connected to form a carbonyl group;
each R3 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R2 connected to a same carbon atom to form a cyclic alkyl, combines with a R2 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, combines with R2 and the carbon to which both R2 and R3 are connected to form a carbonyl group, or combines with R4 connected to adjacent carbon atom to form a carbon-carbon bond; and
each R4 is independently hydrogen or combines with R3 connected to an adjacent carbon atom to form a carbon-carbon bond.

2. The compound of claim 1 , wherein each R1 is hydrogen or halo.

3. The compound of claim 1 , wherein each R2 and each R3 are alkyl.

4. The compound of claim 1 , wherein R4 is hydrogen.

5. The compound of claim 1 , wherein the compound is 3,3,3′,3′-tetramethyl-1,1′-spirobisindan-6,6′-divinyl.

6. A polymerizable composition comprising a compound of Formula (I)

wherein
each R1 is independently hydrogen, halo, alkyl, aryl, alkaryl, or aralkyl;
each R2 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R3 connected to a same carbon atom to form a cyclic alkyl, combines with a R3 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, or combines with R3 and the carbon atom to which both R2 and R3 are connected to form a carbonyl group;
each R3 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R2 connected to a same carbon atom to form a cyclic alkyl, combines with a R2 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, combines with R2 and the carbon to which both R2 and R3 are connected to form a carbonyl group, or combines with R4 connected to adjacent carbon atom to form a carbon-carbon bond; and
each R4 is independently hydrogen or combines with R3 connected to an adjacent carbon atom to form a carbon-carbon bond.

7. The polymerizable composition of claim 6 , wherein the polymerizable composition further comprises a polyvinyl aromatic monomer or a polyvinyl aromatic monomer substituted with one or more alkyl groups.

8. The polymerizable composition of claim 7 , wherein the polyvinyl aromatic monomer is divinylbenzene, trivinylbenzene, divinylbenzene substituted with one or more alkyl groups, or trivinylbezene substituted with one or more alkyl groups.

9. The polymerizable composition of claim 6 , further comprising up to 25 weight percent of a mono-vinyl aromatic monomer or a mono-vinyl aromatic monomer substituted with one or more alkyl groups.

10. The polymerizable composition of claim 9 , wherein polymerizable composition comprises the 1 to 99 weight percent of a monomer of Formula (I), 0 to 25 weight percent of mono-vinyl aromatic monomer, and 1 to 99 weight percent of a polyvinyl aromatic monomer, wherein the weight percents are based on a total weight of monomers in the polymerizable composition.

11. A polymer comprising the polymerized product of a polymerizable composition comprising a compound of Formula (I)

wherein
each R1 is independently hydrogen, halo, alkyl, aryl, alkaryl, or aralkyl;
each R2 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R3 connected to a same carbon atom to form a cyclic alkyl, combines with a R3 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, or combines with R3 and the carbon atom to which both R2 and R3 are connected to form a carbonyl group;
each R3 is independently hydrogen, alkyl, alkoxy, aryl, alkaryl, aralkyl, hydroxyl, silyloxy, combines with a R2 connected to a same carbon atom to form a cyclic alkyl, combines with a R2 connected to the same carbon atom to form a cyclic alkyl that is fused to one or more carbocyclic rings, combines with R2 and the carbon to which both R2 and R3 are connected to form a carbonyl group, or combines with R4 connected to adjacent carbon atom to form a carbon-carbon bond; and
each R4 is independently hydrogen or combines with R3 connected to an adjacent carbon atom to form a carbon-carbon bond.

12. The polymer of claim 11 , wherein the polymerizable composition further comprises a polyvinyl aromatic monomer or a polyvinyl aromatic monomer substituted with one or more alkyl group.

13. The polymer of claim 11 , wherein the polymer is porous.

14. The polymer of claim 13 , wherein the polymer is microporous, mesoporous, or both.

15. The polymer of claim 11 , wherein the BET surface area is at least 300 m 2 /gram.

Assignees

• 3M Innovative Properties Co

Inventors

• Wendland Michael S

Classifications

• C08F216/10

  Carbocyclic compounds · CPC title

• C08F36/20

  unconjugated · CPC title

• C07C35/44

  with a hydroxy group on a condensed ring system having more than three rings · CPC title

• C08F212/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title

• C08F216/36

  by a ketonic radical · CPC title