Granted Patent B2

US 8,987,351 · App. 11/288,485 · Granted Mar 24, 2015

Abstract

Claims (47)

1. A method for treating filler material comprising:

(i) placing a filler into a mixer;

(ii) contacting the filler material with at least one silane of the general formula:

[Y[-G(—SiX u Z b v Z w c ) s ] r ] n   (Formula 1)

wherein

each occurrence of G is independently —(CH 2 ) m —, where m is 1 to 12, —CH 2 (CH 2 ) q CH(CH 3 )—, where q is 0 to 17, or G can be a chemical bond;

each occurrence of X is independently R 1 O— or —O(R 10 CR 11 ) f OH, wherein each occurrence of R 1 is independently hydrogen, methyl, ethyl, propyl, isopropyl or butyl;

each —R 10 and R 11 is independently hydrogen, methyl or ethyl;

each occurrence of Z b is independently (—O—) 0.5 , and [—O(R 10 CR 11 ) f O—] 0.5 , wherein each occurrence of R 10 and R 11 is independently hydrogen, methyl or ethyl;

each occurrence of Z c is independently given by —O(R 10 CR 11 ) f O— wherein each occurrence of R 10 and R 11 is independently hydrogen, methyl or ethyl;

each occurrence of the subscript f is independently an integer from 1 to 15;

each occurrence of the subscript n is an integer from 1 to 100, with the proviso that when n is greater than 1, v is an integer greater than 0 and all the valences for Z b have a silicon atom bonded to them;

each occurrence of the subscript u is independently an integer from 0 to 3;

each occurrence of the subscript v is independently an integer from 0 to 3;

each occurrence of the subscript w, is independently an integer from 0 to 1, with the proviso that u+v+22w=3;

each occurrence of the subscript s is an integer 1;

each occurrence of the subscript r is an integer 1; and

each occurrence of Y is independently an organofunctional group of valence, r, selected from the group consisting of CH 2 —═CH—, CHR═CH—, and CR 2 ═CH—, wherein each occurrence of R is independently hydrogen, methyl, ethyl, propyl, isopropyl, butyl, octenyl, cyclohexyl, phenyl, benzyl, tolyl or tolyl and R 4 is independently one of the structures given for R;

with the provisos that said silane contains at least one occurrence of Z c group and, which upon hydrolysis provides by-product diol, which is not a volatile organic compound possessing a boiling point up to 185° C. at atmospheric pressure;

(iii) mixing the silane composition in contact with the filler of step (ii); and optionally

(iv) drying the mixture of step (iii).

2. The method of claim 1 wherein Y is CH 2 ═CH—.

3. The method of claim 2 wherein G is a chemical bond.

4. The method of claim 3 wherein each occurrence of Z b and Z c is a dialkoxy group derived from ethylene glycol, propylene glycol, neopentyl glycol, 1,3-propanediol, 3-methyl-1,3-propanediol, 1,3-butanediol, 2-methyl-2,4-pentanediol, 1,4-butanediol, and pinacol.

5. The method of claim 1 wherein G is

—(CH 2 ) m — wherein m is 1 to 12 or

—CH 2 (CH 2 ) q CH(CH 3 )— wherein q is zero to 17.

6. The method of claim 1 wherein R 1 is independently methyl, ethyl, propyl, isopropyl, or butyl.

7. The method of claim 1 wherein R 10 and R 11 is each independently selected from a group consisting of hydrogen and methyl.

8. The method of claim 3 wherein R 1 is independently selected from the group consisting of hydrogen, methyl, ethyl and propyl.

9. The method of claim 3 wherein X is independently methoxy, ethoxy, butoxy, propoxy, isopropoxy, or monovalent alkoxy groups having the structure —O(R 10 CR 11 ) f OH, where each occurrence of R 10 and R 11 is independently hydrogen or methyl and f is 1 to 15.

10. The method of claim 9 wherein Z b and Z c are divalent alkoxy groups derived from the diols consisting of ethylene glycol, propylene glycol, neopentyl glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, and 2-methyl-2,4-pentanediol.

11. The method of claim 1 wherein

X is methoxy, ethoxy, propoxy, isopropoxy, butoxy or monovalent alkoxy group derived from 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, or 2-methyl-2,4-pentanediol,

Z b and Z c are derived from 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, or 2-methyl-2,4-pentanediol,

R 1 is independently selected from the group consisting of hydrogen, methyl, ethyl and propyl, and

G is a chemical bond.

12. The method of claim 1 wherein X is ethoxy or one or more of the divalent alkoxy groups derived from the diols selected from the group consisting of 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, and 2-methyl-2,4-pentanediol, and

G is a C 2 -C 12 straight-chain alkyl derivative.

13. The method of claim 1 wherein the filler material includes one or more material selected from the group consisting of silicas, tales, clays, and aluminas, wollastonite, alumina tri-hydrate (ATH), magnesium hydroxide, kaolin, bentonite, precipitated or fumed silica, titanium dioxide, glass beads, basalt, calcium sulfate, calcium carbonate, barium sulfate, graphite, carbon black, hemp, flax and kenaf.

14. The method of claim 1 wherein the filler material comprises particles or fibers.

15. The method of claim 1 wherein the silane is blended with a wax.

16. The method of claim 1 further comprising incorporating the treated filler into a polymeric matrix to provide a composite body.

17. A composite body produced by the method of claim 16 .

18. A method for treating filler material with a composition containing the silane of claim 1 wherein the mixer is a twin-shell mixer, Henschel-style mixer, Littleford-style mixer, or a ribbon blender.

19. A method for treating filler material with a composition containing the silane of claim 1 wherein the treated filler contains the by-product diol, which is not a volatile organic compound possessing a boiling point up to 185° C. at atmospheric pressure.

20. A filler treated with a silane in accordance with the method of claim 1 .

Assignments (23)