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1. (WO2019030059) BISSILYLAMINOSILYL-FUNCTIONALIZED CONJUGATED DIENES AND METHODS FOR THEIR PREPARATION
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Claims

1. A functionalized conjugated diene selected from the group of compounds of formula (Ilia), (Illb), (IIIc)


(Ilia) (Illb) (IIIc)

wherein

R is a linear or branched, saturated or unsaturated hydro- carbylene group, and the starting conjugated diene selected from the group of compounds of formula (la Ic)


from which the functionalized conjugated diene of formula (Ilia), (Illb), (IIIc) is derived, has at least 10 carbon atoms, and the starting conjugated diene of formula (la), (lb), (Ic) is selected from terpenes and 4, 8-dimethyl-l, 3, 7- nonatriene,

- R1 is selected from

i) a single bond,

ii) one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8; and

iii) a hydrocarbylene group which may have one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8,

- R2, R3, R6, R7, R8 can be the same or different and represent an alkyl group containing from 1 to 10 carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms; and

- R4 and R5 can be the same or different, and each R4 and R5 independently represents an alkyl group containing from 1 to 10 carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms.

2. The functionalized conjugated diene of claim 1, wherein R1 is (iii)

a) -(CH2)m-, wherein m represents an integer from 1 to 12; or

b) - ( (CH2) mY (CH2) n) o ~ , wherein m and n independently represent an integer from 0 to 12, o is an integer from 1 to 12, and Y is independently one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8.

3. The functionalized conjugated diene of claim 2, wherein R1 is (iii)b) - (SiR7R8CH2CH2) - .

The functionalized conjugated diene of any of claims 1 to 3, wherein R2, R3, R6, R7, and R8 are the same or different and represent CH3 or Celi5,

preferably wherein R2, R3, R6, R7, and R8 all represent CH3.

The functionalized conjugated diene of any of claims 1 to 4, wherein R4 and R5 all represent C¾ .

The functionalized conjugated diene of any of claims 1 to 5, wherein the terpene is selected from monoterpenes , sesquiterpenes, and diterpenes,

preferably wherein the monoterpene is selected from myrcene and ocimene,

more preferably wherein the myrcene is selected from -myrcene and β-myrcene,

in particular wherein the myrcene is β-myrcene.

The functionalized conjugated diene of claim 6, which is a myrcene derivative of formula (VI), (VII), or (VIII)


(VI) ,



preferably wherein the myrcene derivative is of formula (Via) , (Vila) , or (Villa)

(Via) (Vila) (Villa)

A method for the preparation of a functionalized conjugated diene selected from the group of compounds of formula (Ilia), (Illb), (IIIc)


(Ilia) (Illb) (IIIc)

wherein

- R is a linear or branched, saturated or unsaturated hydro- carbylene group, and the starting conjugated diene selected from the gro Ic)


(la) (lb) (Ic) ,

from which the functionalized conjugated diene of formula (Ilia), (Illb), (IIIc) is derived, has at least 10 carbon atoms, and the starting conjugated diene of formula (la), (lb), (Ic) is selected from terpenes and 4, 8-dimethyl-l, 3, 7- nonatriene,

- R1 is selected from

i) a single bond,

ii) one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8; and

iii) a hydrocarbylene group which may have one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8,

- R2, R3, R6, R7, R8 can be the same or different and represent an alkyl group containing from 1 to 10 carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms; and

- R4 and R5 can be the same or different, and each R4 and R5 independently represents an alkyl group containing from 1 to 10 carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms,

the method comprising reacting, under Grignard conditions, a conjugated diene chloride selected from the group of compounds of formula (Ila), (lib), (lie)


Ha li

with a compound of formula (IV)


wherein Y is selected from chlorine, bromine, and iodine atoms .

9. A method for the preparation of a functionalized conjugated diene selected from the group of compounds of formula (Ilia), (Illb), (IIIc)


(Ilia) (Illb) (IIIc) wherein

- R is a linear or branched, saturated or unsaturated hydrocarbylene group, and the starting conjugated diene selected from the gro Ic)


(la) (lb) (Ic) ,

from which the functionalized conjugated diene of formula (Ilia), (Illb), (IIIc) is derived, has at least 10 carbon atoms, and the starting conjugated diene of formula (la), (lb), (Ic) is selected from terpenes and 4, 8-dimethyl-l, 3, 7- nonatriene,

- R1 is selected from

i) a single bond,

ii) one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8; and

iii) a hydrocarbylene group which may have one or more of an oxygen atom, a sulfur atom, a group NR6, and a group SiR7R8,

- R2, R3, R6, R7, R8 can be the same or different and represent an alkyl group containing from 1 to 10 carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms; and

- R4 and R5 can be the same or different, and each R4 and R5 independently represents an alkyl group containing from 1 to - Al io carbon atoms, or an aryl or aralkyl group containing from 6 to 10 carbon atoms,

the method comprising

A) reacting, under Grignard conditions, a conjugated diene chloride selected from the group of compounds of formula (Ila), (lib), (lie)


with a compound of formula (V)


wherein Y1 and Y2 are independently selected from chlorine, bromine, and iodine atoms, and preferably Y1 and Y2 are each chlorine atoms, to result in a compound of formula (IXa),


(IXb) (IXc)

and

reacting the compound of formula (IXa), (IXb), (IXc) with a bissilylamide of formula (X)

M+

4 5

(R )3Si ^Si(R )3

(X) ,

wherein M is an alkali metal selected from lithium, sodium and potassium, and M is preferably sodium.