Carboxyl-functionalized silicon-containing precursor compound of various organic carboxylic acids

1. A composition comprising:

at least one carboxy-functionalized, silicon-containing precursor of two different organic acids, the precursor compound comprising: two carboxyl groups functionalized with different hydrocarbon radicals,

wherein the precursor compound is of formula I, is an oligomeric siloxane of formula II derived from a compound of formula I, or is a mixture thereof:

(A) z SiR 2 x (OR 1 ) 4−(z+x)   (I)

(R 1 O)[(R 1 O) 2−(x+z) (R 2 ) x Si(A) z O] a [Si(A) z (R 2 ) x (OR 1 ) 2−(x+z) O] b R 1   (II),

wherein

each z is independently 0, 1, or 2,

each x is independently 0, 1 or 2,

each (z+x) is less than or equal to 2,

each A is independently an unsubstituted or substituted hydrocarbon group,

each R 1 is independently at least two carbonyl-R 3 groups,

each R 3 is independently a substituted or unsubstituted hydrocarbon radical having 3 to 45 C atoms,

each R 2 is independently a linear, branched, or cyclic alkyl group having 1 to 24 C atoms, or an aryl group,

a is greater than or equal to 1, and

b is greater than or equal to 1.

2. The composition of claim 1 , wherein each A is independently a linear, branched, or cyclic alkyl-, alkenyl-, aryl-, alkylaryl-, arylalkylene-, cycloalkenyl-alkylene-, haloalkyl-, or acryloyloxyalkyl-functional group.

3. The composition of claim 1 ,

wherein either:

(i) each z is 1; each x is 0; each A is independently a linear, branched, or cyclic alkyl, alkenyl or haloalkyl group having 1 to 8 C atoms or a cyclohexenyl-ethylene group; each R 1 is independently two or three different carbonyl-R 3 groups; and each R 3 is independently an unsubstituted hydrocarbon radical having 3 to 45 C atoms,

or

(ii) each z is 0; each x is 0; each R 1 is independently two, three, or four different carbonyl-R 3 groups; and each R 3 is independently an unsubstituted hydrocarbon radical having 3 to 45 C atoms.

4. The composition of claim 1 , wherein

each R 1 is independently at least two different carbonyl-R 3 groups,

a first R 3 group is an unsubstituted hydrocarbon radical having 3 to 14 C atoms, and

another R 3 group is an unsubstituted hydrocarbon radical having 15 to 45 C atoms.

5. The composition of claim 1 ,

wherein the composition is liquid from about 10° C. to 80° C.

6. The composition of claim 1 , wherein the precursor compound has a solubility of greater than 40% in a hydrocarbon-functionalized alkoxysilane or siloxane.

7. The composition of claim 1 ,

wherein the precursor compound comprises a compound of formula I, and optionally an oligomeric compound of formula II, and

wherein either:

(iii) z is 1; A is H 3 C(CH 2 ) 2 —, H 2 C═CH 2 —, ClCH 2 (CH 2 ) 2 —, C 6 H 9 —(CH 2 ) 2 —, 3-C 6 H 9 —(CH 2 ) 2 —, 2-C 6 H 9 —(CH 2 ) 2 —, 1-C 6 H 9 —(CH 2 ) 2 —, C 6 H 8 —(CH 2 ) 2 —, 1,3-C 6 H 8 —(CH 2 ) 2 —, or 2,4-C 6 H 8 —(CH 2 ) 2 —; OR 1 in formula I comprises two or three different radicals R 1 that are each independently —COC 7 H 15 , —COC 9 H 19 , —COC 11 H 23 , —COC 13 H 27 , —COC 15 H 31 , —COC 17 H 35 , or —COC 21 H 43 ; or

(iv) z is 0 and OR 1 in formula I comprises two, three, or four different radicals R 1 that are each independently —COC 7 H 15 , —COC 9 H 19 , —COC 11 H 23 , —COC 13 H 27 , —COC 15 H 31 , —COC 17 H 35 , or —COC 21 H 43 .

8. The composition of claim 1 ,

wherein the precursor compound comprises at least two carboxyl groups functionalized with different hydrocarbon radicals, and is obtained by a process comprising reacting a halosilane of formula III:

(A) z SiR 2 x (Hal) 4−(z+x)   (III)

with at least two different organic acids of the formula IV:

HOR 1   (IV),

wherein

z is 0, 1, or 2,

x is 0, 1, or 2,

(x+z) is less than or equal to 2,

each Hal is independently a halogen that is chlorine or bromine, and a molar ratio of the at least two different organic acids to the halogen groups is at least stoichiometric.

9. The composition of claim 1 ,

wherein the precursor compound comprises at least one selected from the group consisting of a compound of formula I and a corresponding oligomeric compound thereof;

the compound of formula I is selected from the group consisting of:

H 3 C(CH 2 ) 2 —Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

H 3 C(CH 2 ) 2 —Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

H 2 C═CH 2 —Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

H 2 C═CH 2 —Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

C 6 H 9 —(CH 2 ) 2 —Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

C 6 H 9 —(CH 2 ) 2 —Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

ClCH 2 (CH 2 ) 2 —Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

ClCH 2 (CH 2 ) 2 —Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

(H 19 C 9 OCO) p (ClCH 2 (CH 2 ) 2 )Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

(H 43 C 21 OCO) p (ClCH 2 (CH 2 ) 2 Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

(H 19 C 9 OCO) p (ClCH 2 (CH 2 ) 2 )Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

(H 19 C 9 OCO) p Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

(H 43 C 21 OCO) p Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

(H 33 C 16 )—Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

(H 33 C 16 )—Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

(H 17 C 8 )—Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p ,

(H 17 C 8 )—Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ,

(H 9 C 4 )—Si(OCOC 7 H 15 ) p (OCOC 11 H 23 ) p (OCOC 13 H 27 ) p , and

(H 9 C 4 )—Si(OCOC 13 H 27 ) p (OCOC 15 H 31 ) p (OCOC 17 H 35 ) p ;

each p is independently 0, 1, 2, or 3, with the proviso that p is 1 for at least two different carboxyl groups;

a sum of all ps per precursor compound is 3 if z in formula I is 1; and

a sum of all ps is 4 if the precursor compound is a tetra-carboxy-functionalized precursor compound of formula I and if z=0.

10. A carrier material, comprising the composition of claim 1 .

11. The composition of claim 1 , further comprising:

an organofunctional silane compound of formula V:

(B) b SiR 4 c (OR 5 ) 3−d−c   (V)

wherein each d is independently 0, 1, 2, or 3,

each c is independently 0, 1, 2, or 3,

each sum c+d is less than or equal to 3,

each B is independently a monovalent unsaturated hydrocarbon group, each R 7 independently is a hydrogen atom, a methyl group, or a phenyl group, E is —CH 2 —, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —O(O)C(CH 2 ) 3 — or —C(O)O—(CH 2 ) 3 —,

q is 0 or 1,

each R 5 independently is methyl, ethyl, n-propyl, or isopropyl,

each R 4 independently is a substituted or unsubstituted hydrocarbon group.

12. A carboxy-functionalized, silicon-containing precursor compound of two different organic acids, the precursor compound comprising: two carboxyl groups functionalized with different hydrocarbon radicals,

wherein the precursor compound is of formula I, is an oligomeric siloxane of formula II derived from a compound of formula I, or is a mixture thereof:

(A) z SiR 2 x (OR 1 ) 4−(z+x)   (I)

(R 1 O)[(R 1 O) 2−(x+z) (R 2 ) x Si(A) z O] a [Si(A) z (R 2 ) x (OR 1 ) 2−(x+z) O] b R 1   (II),

each z is independently 0, 1, or 2,

each x is independently 0, 1 or 2,

each (z+x) is less than or equal to 2,

each A is independently an unsubstituted or substituted hydrocarbon group,

each R 1 is independently at least two carbonyl-R 3 groups,

each R 3 is independently a substituted or unsubstituted hydrocarbon radical having 3 to 45 C atoms,

each R 2 is independently a linear, branched, or cyclic alkyl group having 1 to 24 C atoms, or an aryl group,

a is greater than or equal to 1, and

b is greater than or equal to 1.

13. A masterbatch, comprising:

the precursor compound of claim 12 ;

a thermoplastic base polymer, a silane-grafted base polymer, a silane-copolymerized base polymer, a monomer of a thermoplastic base polymer, a monomer of a silane-grafted base polymer, a monomer of a silane-copolymerized base polymer, a prepolymer of a thermoplastic base polymer, a prepolymer of a silane-grafted base polymer, a prepolymer of a silane-copolymerized base polymer, or a mixture thereof; and

optionally a radical initiator.

14. The composition of claim 8 , wherein:

x is 0, and

z is 0 or 1.

15. The composition of claim 1 , further comprising:

a radical initiator,

wherein the composition is suitable for crosslinking thermoplastic base polymers.