Granted Patent B2

US 7,928,258 · App. 11/208,367 · Granted Apr 19, 2011

Abstract

Claims (30)

1. A cyclic and bridging dialkoxy silane composition comprising at least one component having a chemical structure selected from the group consisting of:

wherein:

each occurrence of the —SiX u Z b y Z c w group is independently selected from the group consisting of —SiXZ c , —SiZ b Z c , —SiX 2 Z b , —SiXZ b 2 and —SiZ b 3

each occurrence of R is independently selected from the group consisting of hydrogen, straight, cyclic or branched alkyl, alkenyl groups, aryl groups, and aralkyl groups, with each R, other than hydrogen, containing from 1 to 18 carbon atoms;

each occurrence of G is independently selected from the group consisting of hydrogen, monovalent alkyl, alkenyl, aryl or aralkyl group containing from 1 to 30 carbon atoms, and polyvalent group containing from 1 to 30 carbon atoms derived by substitution of alkyl, alkenyl, aryl or aralkyl group;

each occurrence of Z b , which forms a bridging structure between two different silicon atoms, is independently selected from the group consisting of (—O—) 0.5 and [—O(R 4 CR 5 ) f O—] 0.5 , wherein each occurrence of R 4 and R 5 is independently R;

each occurrence of Z c , which forms a cyclic structure with a single silicon atom, is independently given by —O(R 4 CR 5 ) f O— wherein each occurrence of R 4 and R 5 is independently R;

each occurrence of X is independently selected from the group consisting of —CI, —Br, R 1 O—, R 1 O(R 4 CR 5 ) f O—, R 1 C(═O)O—, R 1 R 2 C═NO—, R 1 R 2 NO—, R 1 R 2 N—, —R 1 , and —(OSi R 1 R 2 ) t (OSi R 1 R 2 R 3 ), wherein each occurrence of R 1 , R 2 and R 3 is independently R;

each occurrence of the subscripts, u, n, v, w, f, p, r, q, j, p, t, and s, is independently given by u is 0 to 3; n is 1 to 100, with the proviso that when n is greater than 1, v is greater than 0 and all the valences for Z b have a silicon atom bonded to them; v is 0 to 3; w is 0 to 1 with the proviso that u+v+2w is 3; f is 1 to 15; p is 0 to 5; r is 1 to 3; q is 0 to 6; j is 0 to 1, with the proviso that when j is 0, p is 1; t is 0 to 50; and s is 1 to 3;

and wherein that each of the above structures comprise at least two hydrolysable bridging dialkoxy group, Z b , or at least one hydrolysable cyclic dialkoxy group, Z c .

2. The silane composition of claim 1 , wherein the sum of the carbon atoms within the G groups is from 3 to 18.

3. The silane composition of claim 1 , wherein the sum of the carbon atoms within the G groups is from 6 to 10.

4. The silane composition of claim 1 , wherein G is a monovalent hydrocarbon group.

5. The silane composition of claim 1 , wherein G is —(CH 2 ) g — wherein g is 1 to 29.

6. The silane composition of claim 1 , wherein G is CH 3 (CH 2 ) g — wherein g is 1 to 29.

7. The silane composition of claim 1 , wherein G is diethylene cyclohexane.

8. The silane composition of claim 1 , wherein G is selected from the group consisting of 1,2,4-triethylene cyclohexane, diethylene benzene and phenylene.

9. The silane composition of claim 1 , wherein each G is independently selected from the group consisting of —CH 2 CH 2 CH 2 — and CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —.

10. The silane composition of claim 1 , wherein R is selected from the group consisting of methyl, ethyl, propyl, isopropyl, octenyl, cyclohexyl, butyl, phenyl, benzyl, tolyl and allyl.

11. The silane composition of claim 1 , wherein at least one component contains the cyclic dialkoxy group, represented by the formula:

—O(R 4 CR 5 ) f O—

wherein each occurrence of R 4 and R 5 is independently selected from the group consisting of hydrogen, straight, cyclic or branched alkyl, alkenyl groups, aryl groups, and aralkyl groups, with each R, other than hydrogen, containing from 1 to 18 carbon atoms.

12. The silane composition of claim 1 , wherein R 4 and R 5 are selected from the group consisting of hydrogen, methyl, ethyl and propyl.

13. The silane composition of claim 1 , wherein R 1 and R 2 are selected from the group consisting of hydrogen, methyl, ethyl and propyl.

14. The silane composition of claim 1 , wherein X is selected from the group consisting of methoxy, ethoxy, isobutoxy, propoxy, isopropoxy, acetoxy, methoxyethoxy, oximato and R 1 O(R 4 CR 5 ) f O—.

15. The silane composition of claim 1 , wherein Z b and Z c are selected from the group consisting of divalent alkoxy groups derived from the diols, ethylene glycol, propylene glycol, neopentyl glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, 2-methyl-2,4-pentanediol, 1,4-butanediol, cyclohexane dimethanol and pinacol.

16. The silane composition of claim 1 , wherein the ratio of v/w is between 0 and 1; p is 0 to 2; X is RO—or RC(═O)O—; Z b and Z c are dialkoxy groups derived from 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, and/or 2-methyl-2,4-pentanediol; R is a C 1 to C 4 alkyl or hydrogen; and G when univalent is a straight chain alkyl of 3 to about 18 carbon atoms.

17. The silane composition of claim 1 , wherein the ratio of v/w is between 0 and 0.1; X is ethoxy; Z b and Z c are bridging and cyclic dialkoxy groups derived from 1,3-propanediol, 2-methyl-1,3-propanediol, 1,3-butanediol, and/or 2-methyl-2,4-pentanediol; and G is a monovalent C 3 -C 12 straight-chain alkyl group or a polyvalent C 3 -C 12 group derived by substituting a straight-chain alkyl.

18. A cyclic and bridging dialkoxysilane composition comprising at least one component having a chemical component from the group consisting of

2-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-ethyl thioacetate; 2-(2-methyl-2,4-pentanedialkoxymethoxysilyl )-1-ethyl thioacetate; 2-(2-methyl-2,4-pentanedialkoxymethylsilyl )-1-ethyl thioacetate; 3-(2-methyl-2,4-pentanedialkoxymethoxysilyl )-1-propyl thioacetate; 2-methyl-2,4-pentanedialkoxyethoxysilylmethyl thioacetate; 2-methyl-2,4-pentanedialkoxyisopropoxysilylmethyl thioacetate; neopentylglycoxypropoxysilylmethyl thioacetate; propyleneglycoxymethylsilylmethyl thioacetate; neopentylglycoxyethylsilylmethyl thioacetate; 2-(neopentylglycoxyisopropoxysilyl)-1-ethyl thioacetate; 2-(neopentylglycoxymethylsilyl)-1-ethyl thioacetate; 2-(1,3-butanedialkoxymethylsilyl)-1-ethyl thioacetate; 3-(1,3-butanedialkoxyethoxysilyl)-1-propyl thioacetate; 3-(1,3-butanedialkoxyisopropoxysilyl )-4-butyl thioacetate; 3-(1,3-butanedialkoxyethylsilyl)-1-propyl thioacetate; 3-(1,3-butanedialkoxymethylsilyl)-1-propyl thioacetate; 6-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-hexyl thioacetate; 1-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-5-hexyl thioacetate; 8-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-octyl thioacetate; 10-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-decyl thioacetate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiooctanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiodecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiododecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-ethylhexanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-methylheptanoate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl) dithioadipate; 6-(1,3-butanedialkoxyethoxysilyl)-1-hexyl thioacetate; 1-(1,3-butanedialkoxyethoxysilyl)-5-hexyl thioacetate; 8-1,3-butanedialkoxyethoxysilyl )-1-octyl thioacetate; 10-(1,3-butanedialkoxyethoxysilyl)-1-decyl thioacetate; 3-(1,3-butanedialkoxyethoxysilyl)-1-propyl thiooctanoate; 3(1,3-butanedialkoxyethoxysilyl )-1-propyl thiodecanoate; 3-(1,3-butanedialkoxypropoxysilyl )-1-propyl thiododecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-ethylhexanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-methylheptanoate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)dithioadipate; tris-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)trithiophosphate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)methyldithiophosphonate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)ethyldithiophosphonate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyldimethylthiophosphinate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyldiethylthiophosphinate; tris-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl)tetrathiophosphate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)methyltrithiophosphonate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl)ethyltrithiophosphonate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyldimethyldithiophosphinate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyldiethyldithiophosphinate; tris-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl )-1-propyl)trithiophosphate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propylmethylthiosulphate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propylmethanethiosulphonate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propylethanethiosulphonate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propylbenzenethiosulphonate; 3-(2-methyl-1,3-propanedialkoxyethoxysilyl )-1-propyl thiootanoate; 3-[2-methyl-1,3-propanedialkoxy(2-methyl-3-hydroxypropoxy)silyl]-1-propyl thiooctanoate; 3-(2-methyl-1,3-propanedialkoxyethoxysilyl )-1-propyl thiodecanoate; 3-(2,2-dimethyl-1,3-propanedialkoxyethoxysilyl )-1-propyl thiodecanoate; 3-(2,2-dimethyl-1,3-propanedialkoxyethoxysilyl )-1-propyl thiooctanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiooctanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiodecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiododecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thiotetradecanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-ethylhexanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl thio-2-methylheptanoate; bis-(3-(2-methyl-2,4-pentanedialkoxyethoxysilyl )-1-propyl) dithioadipate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiooctanoate; 3-(2-methyl-2,4-pentanedialkoxyethoxysilyl)-1-propyl thiodecanoate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thioacetate; 2-methyl-2,4-pentanedialkoxyisopropylsilylmethyl thioacetate; 6-(2-methyl-2,4-pentanedialkoxyethylsilyl)-1-hexyl thioacetate; 1-(2-methyl-2,4-pentanedialkoxymethylsilyl)-5-hexyl thioacetate; 8-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-octyl thioacetate; 10-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-decyl thioacetate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiooctanoate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiodecanoate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thiododecanoate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl)-1-propyl thio-2-ethylhexanoate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl )-1-propyl thio-2-methylheptanoate; bis-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl )-1-propyl) dithioadipate; 3-(1,3-butanedialkoxybutylsilyl)-1-propyl thioacetate; 3-(1,3-butanedialkoxyisopropylsilyl)-4-butyl thioacetate; 6-(1,3-butanedialkoxymethylsilyl )-1-hexyl thioacetate; 8-(1,3-butanedialkoxymethylsilyl)-1-octyl thioacetate; 10-(1,3-butanedialkoxymethylsilyl)-1-decyl thioacetate; 3-(1,3-butanedialkoxymethylsilyl )-1-propyl thiooctanoate; 3-(1,3-butanedialkoxymethylsilyl)- 1 -propyl thiodecanoate; 3-(1,3-butanedialkoxypropylsilyl)-1-propyl thiododecanoate; 3-(2,2-dimethyl-1,3-propanedialkoxymethylsilyl )-1-propyl thiodecanoate; 3-(2,2-dimethyl-1,3-propanedialkoxymethylsilyl)-1-propyl thiooctanoate; 3-(2-methyl-1, 3-propanedialkoxymethylsilyl )-1-propyl thiooctanoate; 3-(2-methyl-1,3-propanedialkoxymethylsily 1 )-1-propyl thiodecanoate; 3-(2-methyl-1, 3-propanedialkoxymethylsilyl )-1-propyl thiododecanoate; 3-(2-methyl-1,3-propanedialkoxymethylsilyl )-1-propyl thiotetradecanoate; 3-(2-methyl-1,3-propanedialkoxymethylsilyl)-1-propyl thio-2-ethylhexanoate; 3-(2-methyl-1,3-propanedialkoxymethylsilyl )-1-propyl thio-2-methylheptanoate; bis-(3-(2-methyl-1,3-propanedialkoxymethylsilyl)-1-propyl) dithioadipate; neopentylglycoxypropylsilylmethyl thioacetate; bis-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyl)-methyl)dithiophosphonate; bis-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyl)-ethyl) dithiophosphonate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyldimethylthiophosphinate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyldiethylthiophosphinate; tris-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyl)tetrathiophosphate; bis-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyl)methyltrithiophosphonate; bis-(3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyl)ethyltrithiophosphonate; 3-(2-methyl-2,4-pentanedialkoxyethylsilyl-1-propyldimethyldithiophosphinate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propyldiethyldithiophosphinate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propylmethylthiosulphate; 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propylmethanethiosulphonate; 3-(2-methyl-2,4-pentanedialkoxypropylsilyl-1-propylethanethiosulphonate; and 3-(2-methyl-2,4-pentanedialkoxymethylsilyl-1-propylbenzenethiosulphonate.

Assignments (23)