Functionalized resin having a polar linker

Patent metadata

Field	Value
Publication number	US-10875943-B2
Application number	US-201815949887-A
Country	US
Kind code	B2
Filing date	Apr 10, 2018
Priority date	Apr 10, 2017
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

Abstract

Polar silane linkers are provided that attach to resins to form silane-functionalized resins. The functionalized resins can be bound to hydroxyl groups on the surface of silica particles to improve the dispersibility of the silica particles in rubber mixtures. Further disclosed are synthetic routes to provide the silane-functionalized resins, as well as various uses and end products that benefit from the unexpected properties of the silane-functionalized resins. Silane-functionalized resins impart remarkable properties on various rubber compositions, such as tires, belts, hoses, brakes, and the like. Automobile tires incorporating the silane-functionalized resins are shown to possess excellent results in balancing the properties of rolling resistance, tire wear, and wet braking performance.

First claim

What is claimed is:

1. A functionalized resin comprising formula I:
resin-[Z k —X n —R 1 —(CH 2 ) m —Si(R 2 ) p ] q   (I)

wherein Z is a phenyl group or a cyclo-aliphatic group, optionally comprising a heteroatom;
wherein X is a linker beginning with oxygen covalently bound to Z k ;
wherein R 1 comprises one or more of an aliphatic and/or aromatic C 1 to C 18 and/or a linkage group comprising a heteroatom;
wherein X and R 1 together comprise at least one hydroxyl group;
wherein each R 2 is the same or different and is independently selected from a C 1 to C 18 alkoxy, aryloxy, alkyl, aryl, or H, or OH, and is optionally branched, and wherein at least one R 2 is C 1 to C 18 alkoxy, aryloxy, or H, or OH;
wherein q is an integer from of at least 1;
wherein k is an integer of 1;
wherein n is an integer of 1;
wherein m is an integer from 0 to 10;
wherein p is 1, 2, or 3, and
wherein the resin is obtained by polymerizing or co-polymerizing one or more of an unsaturated aliphatic monomer, terpenes, rosin acid, unsaturated cycloaromatic monomers, unsaturated cycloaliphatic monomers, unsaturated fatty acids, methacrylates, unsaturated aromatic monomers, vinyl aromatic monomers, and/or an unsaturated aliphatic/aromatic monomer mixture, and/or wherein the resin is hydrogenated, partially hydrogenated, or non-hydrogenated.

2. The functionalized resin of claim 1 , wherein q is an integer from 2 to 8.

3. The functionalized resin of claim 1 , wherein —[Z k —X n —R 1 —(CH 2 ) m —Si(R 2 ) p ] q of Formula I is positioned at one or more ends of the functionalized resin, is distributed randomly throughout the functionalized resin, is present in blocks throughout the functionalized resin, is present in segments of the functionalized resin, is present at least once per functionalized resin, is present at least twice per functionalized resin, and/or is present in the middle of each functionalized resin.

4. The functionalized resin of claim 1 , wherein:
the aromatic monomers and/or vinyl aromatic monomer comprises one or more of styrene, vinyl toluene, alpha-methyl styrene, and/or diisopropylbenzene, or
wherein the aliphatic monomer comprises one or more of C 5 piperylenes, coumarone, indene, and/or dicyclopentadiene.

5. The functionalized resin of claim 1 , wherein:
X further comprises a phenol, an amine, an imidazole, an amide, a polysulfide, a sulfoxide, a sulfone, a sulfonamide, a sulfonium, an ammonium, a carboxylic acid, an ester, a thioester, an ether, a maleimide, a carbamate, cyanate, isocyanate, thiocyanate, a pyridinium, or combinations thereof,
R 1 is a C 1 to C 10 carbon chain or a C 1 to C 5 carbon chain, and/or
R 2 is a C 1 to C 10 alkoxy, aryloxy, alkyl, or aryl group, or a C 1 to C 5 alkoxy, aryloxy, alkyl, or aryl group, and is optionally branched.

6. The functionalized resin of claim 1 , wherein each R 2 is independently selected from a methoxy, hydroxyl, an ethoxy, and a propoxy group.

7. The functionalized resin of claim 1 , wherein an amount of silane-containing groups grafted onto the resin is about 0.001 to about 100 mol %, about 0.1 to about 50 mol %, or about 5 to about 50 mol %.

8. The functionalized resin of claim 1 , wherein the resin has a weight average molecular weight Mw of about 200 to about 200,000 g/mol, about 200 to about 50,000 g/mol, about 200 to about 20,000 g/mol, or about 200 to about 15,000 g/mol.

9. The functionalized resin of claim 1 , wherein the resin has a polydispersity index (PDI) of about 1 to 10, and/or the resin has a glass transition temperature Tg of below about 200° C.

10. The functionalized resin of claim 1 , wherein the Tg is less than about 160° C.

11. The functionalized resin of claim 1 , wherein the amount of silane groups grafted onto the resin is from about 0.01 to about 30 mol % or about 0.01 to about 50 mol %.

12. The functionalized resin of claim 1 , wherein the resin has a number average molecular weight Mn of about 500 g/mol to about 1,000 g/mol, or about 2,500 g/mol to about 10,000 g/mol.

13. The functionalized resin of claim 12 , wherein the resin has a weight average molecular weight Mw of from about 400 g/mol to about 2,000 g/mol.

14. The functionalized resin of claim 1 , wherein the polydispersity index (PDT) is about 1 to about 5.

15. The functionalized resin of claim 1 , wherein the PDI is from 1 to 2.

16. The functionalized resin of claim 1 , wherein the functionalized resin is bound to a silica particle by a Si—O—Si moiety following hydrolysis of at least one —R 2 group.

17. The functionalized resin of claim 1 , wherein a functionalized resin molecule is bound to a second functionalized resin molecule by a Si—O—Si moiety following hydrolysis of at least one R 2 group.

18. The functionalized resin of claim 1 , wherein
R 1 is one or more of —O—CO—NH—R 3 —(CH 2 ) 2 —, O—CO—R 3 —(CH 2 ) 2 —, —O—CH 2 —R 3 —(CH 2 ) 2 —, —CO—R 3 —(CH 2 ) 2 —, and —CO—NH—R 3 —(CH 2 ) 2 —, and
R 3 is an aliphatic or aromatic C 1 to C 8 carbon chain, optionally branched, and/or optionally comprising one or more heteroatom.

Assignees

• Eastman Chem Co

Inventors

• Anderson Emily Baird
• Baker Jr John Dayton
• Carvagno Terri Roxanne
• Chapelet Judicael Jacques
• Cheng Wei Min
• Deng Liu
• De Hullu Jacobus Gillis
• Finger Sebastian
• Hirschlag Hubert
• Lester Christopher Lee
• Li Wentao
• Muvundamina Mutombo Joseph
• Pavlin Mark Stanley
• Peters Fabian
• Recker Carla
• Scilla Christopher Thomas

Classifications

• C08F30/08 Primary

  containing silicon · CPC title

• C08F220/1811 Primary

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• C08F212/08

  Styrene · CPC title

• C08F20/16

  of phenols or of alcohols containing two or more carbon atoms · CPC title

• C08L23/0853

  Ethylene vinyl acetate copolymers · CPC title