SILICONE-POLYETHER COPOLYMER, METHOD OF PREPARING SAME, AND SEALANT COMPRISING SAME

• US 20200131369A1
• Filed: 06/26/2018
• Published: 04/30/2020
• Est. Priority Date: 06/26/2017
• Status: Active Grant

• Current Assignee: Dow Silicones Corporation (Dow, Inc.)
• Original Assignee: Dow Global Technologies LLC (Dow, Inc.), Dow Silicones Corporation (Dow, Inc.)
• Inventors: GRASMANN, Martin, HAGAN, David, HARKNESS, Brian, HEATH, William H., HLINKA, II, Stephen Michael, JOFFRE, Eric, JOHNSON, William, KRISHNAN, Bindu, YOUNG, Jeanette, ZHU, Bizhong
• Granted Patent: US 10,676,568 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 2531/828 Platinum
• CPC Class Codes: B01J 31/124 Silicones or siloxanes or comprising such units
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/242 organometallic compounds containing tin-carbon bonds
• CPC Class Codes: C08G 18/244 tin salts of carboxylic acids
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/4829 Polyethers containing at least three hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/5096 containing silicon
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C08G 65/336 containing silicon
• CPC Class Codes: C08G 65/34 from hydroxy compounds or their metallic derivatives C08G65/26 takes precedence
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08G 77/48 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08G77/42 takes precedence
• CPC Class Codes: C08K 5/0016 : Plasticisers
• CPC Class Codes: C08K 5/0025 : Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08K 5/12 : of cyclic polycarboxylic acids
• CPC Class Codes: C08K 5/5415 : containing at least one Si—O bond
• CPC Class Codes: C08K 5/57 : Organo-tin compounds
• CPC Class Codes: C08L 71/02 : Polyalkylene oxides
• CPC Class Codes: C08L 83/12 : containing polyether sequences
• CPC Class Codes: C09D 171/02 : Polyalkylene oxides
• CPC Class Codes: C09D 183/12 : containing polyether sequences
• CPC Class Codes: C09K 2200/0685 : Containing silicon
• CPC Class Codes: C09K 3/1021 : Polyurethanes or derivatives thereof

Abstract

A silicone-polyether copolymer has the formula X_g—Y, where each X is an independently selected silicone moiety having a particular structure, Y is a linear or branched polyether moiety, and subscript g is on average more than 1. A method of preparing the silicone-polyether copolymer comprising reacting a polyether compound and an organosilicon compound in the presence of a hydrosilylation-reaction catalyst. A sealant is also disclosed, the sealant comprising the silicone-polyether copolymer and a condensation-reaction catalyst.

Claims

1. A silicone-polyether copolymer having the formula X_g—

Y,

wherein Y is a linear or branched polyether moiety; and

each X is an independently selected silicone moiety having one of formulas (I)-(III);

2. The silicone-polyether copolymer of claim 1, wherein the polyether moiety Y has the formula

-D²-O—

(C_nH_2nO)_w-D²-,

where each D² is an independently selected divalent group having from 2 to 6 carbon atoms, subscript n is independently selected from 2 to 4 in each moiety indicated by subscript w, and subscript w is from 1 to 2,000.

3. The silicone-polyether copolymer of claim 1, wherein:

(i) the polyether moiety Y has the formula

-D²-O—

(C₂H₄O)_x(C₃H₆O)_y(C₄H₈O)_z-D²-,

where each D² is an independently selected divalent group having from 2 to 5 carbon atoms, subscript x is from 0 to 1,999, subscript y is from 1 to 2,000, and subscript z is from 0 to 1,999, and where units indicated by subscripts x, y and z may be in randomized or block form in the polyether moiety Y;

(ii) the polyether moiety Y has a number average molecular weight of at least about 100;

or

(iii) both (i) and (ii).

4. The silicone-polyether copolymer of claim 1, wherein:

(i) each R¹ is methyl;

(ii) each R² is propyl;

(iii) each subscript a is 0;

(iv) each D¹ is C₂H₄;

or

(v) any combination of (i) to (iv).

5. The silicone-polyether copolymer of claim 1, wherein:

(i) the polyether moiety Y is trivalent or tetravalent;

(ii) the polyether moiety Y includes at least one structural unit derived from a trihydroxyl compound and/or a tetrahydroxyl compound;

or

(iii) both (i) and (ii).

6. A method of preparing a silicone-polyether copolymer, said method comprising:

reacting a polyether compound having an average of greater than one terminal unsaturated group and an organosilicon compound in the presence of a hydrosilylation catalyst to give the silicone-polyether copolymer;

wherein the silicon-polyether copolymer is according to claim 1.

7. The method of claim 6, wherein the polyether compound has the formula

R³—

O—

(C_n′

H_2n′

O)_w′

—

R³,

where each R³ is an unsaturated group having from 2 to 6 carbon atoms, each n′

is independently selected from 2 to 4 in each moiety indicated by subscript w′

, and subscript w′

is from 1 to 2,000.

8. The method of claim 6, wherein:

(i) the polyether compound has the formula

R³—

O—

(C₂H₄O)_x(C₃H₆O)_y(C₄H₈O)_z—

R³,

where each R³ is an unsaturated group having from 2 to 6 carbon atoms, subscript x is from 0 to 1,999, subscript y is from 1 to 2,000, and subscript z is from 0 to 1,999, and where units indicated by subscripts x, y and z may be in randomized or block form in the polyether compound;

(ii) the polyether compound has a number average molecular weight of at least about 100;

or

(iii) both (i) and (ii).

9. The method of claim 6, wherein the organosilicon compound is an organohydrogensiloxane compound having one of formulas (IV)-(VI):

10. The method of claim 9, wherein:

(i) each R¹ is methyl;

(ii) R² is propyl;

(iii) each subscript a is 0;

(iv) each D¹ is C₂H₄;

or

(v) any combination of (i) to (iv).

11. A silicone-polyether copolymer prepared in accordance with the method of claim 6.

12. A sealant, comprising:

a silicone-polyether copolymer; and

a condensation reaction catalyst;

wherein the silicone-polyether copolymer is according tom claim 1.

13. The sealant of claim 12, further comprising:

(i) a filler;

(ii) a filler treating agent;

(iii) a cross-linker;

(iv) a surface modifier, (v) a drying agent;

(vi) an extender;

(vii) a biocide;

(viii) a flame retardant;

(ix) a plasticizer;

(x) an end-blocker;

(xi) a binder;

(xii) an anti-aging additive;

(xiii) a water release agent;

(xiv) a pigment;

(xv) a rheology modifier;

(xvi) a carrier;

(xvii) a tackifying agent;

(xviii) a corrosion inhibitor;

(xvix) a catalyst inhibitor;

(xx) an adhesion promotor;

(xxi) a viscosity modifier;

(xxii) a UV absorber;

(xxiii) an anti-oxidant;

(xxiv) a light-stabilizer;

or (xxv) a combination of (i)-(xxiv).

14. The sealant of claim 13, wherein the sealant comprises the filler, the cross-linker, the extender, the plasticizer, and the adhesion promotor.

15. A cured product of the sealant of claim 12.

16. A composite article comprising a substrate and the cured product of claim 15 disposed on the substrate.

17. A method of preparing a composite article, said method comprising:

disposing a sealant on a substrate; and

curing the sealant to give a cured product on the substrate, thereby forming the composite article;

wherein the sealant is according to claim 12.

18. A method of sealing a space defined between two elements, said method comprising:

applying a sealant to the space; and

curing the sealant in the space, thereby sealing the space;

wherein the sealant is according to claim 12.