IP Library Granted Patent US 7,666,933
Granted Patent B2
US 7,666,933 · App. 10/828,170 · Granted Feb 23, 2010

Organosilane masterbatch

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,666,933
App. No.
10/828,170
Granted
Feb 23, 2010
Kind
B2
Abstract

An organosilane masterbatch containing (a) 2-20 parts by weight of rubber, (b) 0-60 parts by weight of filler, (c) 5-55 parts by weight of organosilane and (d) 0-10 parts by weight of dispersing agent. A process for preparing the organosilane masterbatch by mixing the rubber, filler, organosilane and dispersing agent in a banbury or kneader, extruding and cutting into pieces. Rubber mixtures containing the organosilane masterbatch can be used in rubber mixtures.

Claims (70)

1. An organosilane masterbatch comprising

(a) 2 to 9 parts by weight of one or more rubbers,

(b) 30 to 60 parts by weight of one or more carbon black fillers, wherein said fillers are the only fillers in the organosilane masterbatch,

(c) 15 to 55 parts by weight of one or more organosilanes, and

(d) 0.5 to 5 parts by weight of one or more dispersing agents.

2. The organosilane masterbatch according to claim 1 , wherein the rubber is at least one of E-SBR or S-SBR.

3. The organosilane masterbatch according to claim 1 , wherein the organosilane is of formula I

Z—A—S x —A—Z  (I)

wherein

x is a number from 1 to 12;

Z is SiX 1 X 2 X 3 wherein X 1 , X 2 , X 3 can each mutually or independently be a hydrogen, a halogen, a hydroxy, an alkyl substituent, an alkenyl acid substituent, a linear hydrocarbon chain with 1-6 carbon atoms, a branched hydrocarbon chain with 1-6 carbon atoms, a cycloalkyl radical with 5-12 carbon atoms, a benzyl radical, a halogen-substituted phenyl radical, an alkyl-substituted phenyl radical, an alkoxy group with one or more linear or branched hydrocarbon chains having from 1 to 6 carbon atoms, a cycloalkoxy group having 1 to 5 carbon atoms, a halogen-substituted phenoxy group, an alkyl-substituted phenoxy group or a benzyloxy group;

A is a C 1 -C 16 branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent hydrocarbon group or an organosilane of formula II

Z—A—Y  (II)

wherein

Z and A have the same meaning as in formula (I) and

Y is SH, SCN, S—C(O)—X 1 , a straight-chain (C 1 -C 18 ) alkyl, a branched (C 1 -C 18 ) alkyl, a cyclic (C 1 -C 18 ) alkyl, a (C 1 -C 5 ) alkoxy, a halogen, a hydroxy, a nitrile, a (C 1 -C 4 ) haloalkyl, —NO 2 , a (C 1 -C 8 ) thioalkyl, —NH 2 , —NHR 1 , —NR 1 R 2 , an alkenyl, an allyl, a vinyl, an aryl or a (C 7 -C 16 ) aralkyl.

4. The organosilane masterbatch according to claim 3 , wherein the organosilane is at least one selected from the group consisting of

3,3′-bis(trimethoxysilylpropyl) disulfide,

3,3′-bis(triethoxysilylpropyl) tetrasulfide,

3,3′-bis(trimethoxysilylpropyl) tetrasulfide,

2,2′-bis(triethoxysilylethyl) tetrasulfide,

3,3′-bis(trimethoxysilylpropyl) trisulfide,

3,3′-bis(triethoxysilylpropyl) trisulfide,

3,3′-bis(trimethoxysilylpropyl) hexasulfide,

2,2′-bis(methoxy diethoxy silyl ethyl) tetrasulfide,

2,2′-bis(tripropoxysilylethyl) pentasulfide, bis(trimethoxysilylmethyl) tetrasulfide,

2,2′-bis(methyl dimethoxysilylethyl) trisulfide,

2,2′-bis(methyl ethoxypropoxysilylethyl) tetrasulfide,

5,5′-bis(dimethoxymethylsilylpentyl) trisulfide,

3,3′-bis(trimethoxysilyl-2-methoxypropyl) tetrasulfide,

5,5′-bis(triethoxysilylpentyl) tetrasulfide,

4,4′-bis(triethoxysilylbutyl) tetrasulfide,

3,3′-bis(diethoxymethylsilylpropyl) trisulfide,

bis(triethoxysilylmethyl) tetrasulfide,

3,3′-bis(dimethylethoxysilylpropyl) tetrasulfide,

3,3-bis(dimethylmethoxysilylpropyl) tetrasulfide,

3,3′-bis(dimethylethoxysilylpropyl) disulfide,

3,3′-bis(dimethylmethoxysilylpropyl) disulfide,

3-mercaptopropyltriethoxysilane,

3-mercaptopropyltrimethoxysilane,

3,3′-bis(dodecanyldiethoxysilylpropyl) tetrasulfide,

3,3′-bis(didodecanylethoxysilylpropyl) tetrasulfide,

3,3′-bis(hexadecanyldiethoxysilylpropyl) tetrasulfide,

3,3′-bis(dihexadecanylethoxysilylpropyl) tetrasulfide,

3,3′-bis(dodecanyldiethoxysilylpropyl) disulfide,

3,3-bis(didodecanylethoxysilylpropyl) disulfide,

3,3′-bis(hexadecanyldiethoxysilylpropyl) disulfide,

3,3′-bis(dihexadecanylethoxysilylpropyl) disulfide,

3-triethoxysilyl-1-propylthiooctoate,

3-trimethoxysilyl-1-propylthiooctoate,

3-triethoxysilyl-1-propylthiohexanoate,

3-trimethoxysilyl-1-propylthiohexanoate,

3-triethoxysilyl-1-propylthiobenzoate,

3-trimethoxysilyl-1-propylthiobenzoate and

3-thiocyanatopropyltriethoxysilane.

5. The organosilane masterbatch of claim 1 , comprising (a) from 2 to 5 parts by weight of the rubber, (b) from 40 to 55 parts by weight of the filler, (c) from 45 to 55 parts by weight of the organosilane and (d) from 0.5 to 1.5 parts by weight of the dispersing agent.

6. The organosilane masterbatch of claim 3 , wherein x is from 1 to 8.

7. The organosilane masterbatch of claim 3 , wherein x is from 2 to 6.

8. The organosilane masterbatch of claim 1 , wherein the organosilane is bis(triethoxysilylpropyl)tetrasulfane.

9. The organosilane masterbatch of claim 1 , wherein the rubber is E-SBR, the filler is a pelletized carbon black, the organosilane is bis(triethoxysilylpropyl)tetrasulfane and the dispersing agent is a blend of high molecular weight aliphatic fatty acid esters and condensation products bound to chemically inert fillers.

10. The organosilane masterbatch of claim 1 , obtained by mixing the rubber, the filler, the organosilane and the dispersing agent in a banbury mixer or a kneader to form a mixture, extruding the mixture and then cutting the extruded mixture to form a granulate.

11. A rubber-containing composition comprising the organosilane masterbatch according to claim 1 .

12. An article of manufacture comprising the rubber-containing composition of claim 11 .

13. The article of manufacture of claim 12 selected from the group consisting of a molding, a pneumatic tire, a tire tread, a cable covering, a flexible tube, a drive belt, a conveyor belt, a roller coating, a tire, a shoe sole, a washer and a damping element.

14. A vulcanized rubber composition comprising the organosilane composition of claim 1 .

15. A process for the production of the organosilane masterbatch according to claim 1 , comprising:

mixing the rubber, the filler, the organosilane and the dispersing agent in a banbury mixer or a kneader to form a mixture,

extruding the mixture, and

cutting the extruded mixture to form the organosilane masterbatch as a granulate.

16. The process as claimed in claim 15 , wherein the temperature is below 80° C.

Assignments (2)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
CHANGE ADDRESS Recorded Feb 22, 2010
From: EVONIK DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 023985/0296 →