ISOCYANATE-FUNCTIONAL SILICONE-POLYETHER COPOLYMER, SILICONE-POLYETHER-URETHANE COPOLYMER FORMED THEREWITH, SEALANTS COMPRISING SAME, AND RELATED METHODS

• US 20200131368A1
• 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, XU, Qiuyun, ZHU, Bizhong
• Granted Patent: US 10,800,921 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

An isocyanate-functional silicone-polyether copolymer having a particular structure is disclosed. A method of preparing the isocyanate-functional silicone-polyether copolymer is also disclosed, the method comprising reacting a polyether compound and an organosilicon compound to give the isocyanate-functional silicone-polyether copolymer. A silicone-polyether-urethane copolymer formed therewith, as well as a method of preparing the silicone-polyether-urethane copolymer, are also disclosed. Sealants comprising the isocyanate-functional silicone-polyether copolymer and/or the silicone-polyether-urethane copolymer are further disclosed.

Claims

1. An isocyanate-functional silicone-polyether copolymer having the following formula:

2. The isocyanate-functional silicone-polyether copolymer of claim 1, wherein the polyether moiety Y′

has the formula

—

(C_nH_2nO)_wC_mH_2m,

wherein each subscript n is independently selected from 2 to 4 in each moiety indicated by subscript w;

subscript w is from 1 to 200; and

subscript m is from 2 to 4.

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

(i) the polyether moiety Y′

has the formula

(C₂H₄O)_x(C₃H₆O)_y(C₄H₈O)_zC_mH_2m,

wherein subscript x is from 0 to 200;

subscript y is from 1 to 200;

subscript z is from 0 to 200;

subscript m is from 2 to 4; and

wherein 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 isocyanate-functional silicone-polyether copolymer of claim 1, wherein:

(i) each R¹ is methyl;

(ii) a is 0;

(iii) D is C₂H₄;

or

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

5. A method of preparing an isocyanate-functional silicone-polyether copolymer, said method comprising:

reacting a silicone-polyether copolymer and a polyisocyanate to give the isocyanate-functional silicone-polyether copolymer;

wherein the isocyanate-functional silicone-polyether copolymer is according to claim 1.

6. The method of claim 5, wherein the silicone-polyether copolymer has the following formula:

7. The method of claim 5, wherein the polyisocyanate:

(i) has a nominal functionality of at least 1.6;

or

(ii) comprises a diisocyanate compound having the formula NCO-D′

-OCN, wherein D′

is a divalent linking group.

8. An isocyanate-functional silicone-polyether copolymer prepared in accordance with the method of claim 5.

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

reacting an isocyanate-functional silicone-polyether copolymer and a coupling agent having an average of more than one isocyanate-reactive functional group to give the silicone-polyether-urethane copolymer;

wherein the isocyanate-functional silicone-polyether copolymer is according to claim 1.

10. The method of claim 9, wherein the coupling agent comprises at least one of a diol, a triol, a tetraol, a pentaol, and a hexaol.

11. The method of claim 9, wherein the silicone-polyether-urethane copolymer has the formula

X-D″

-X,

wherein D″

is a divalent linking group, and each X has the following formula;

12. A silicone-polyether-urethane copolymer prepared in accordance with the method of claim 9.

14. A sealant, comprising:

an isocyanate-functional silicone-polyether copolymer; and

a condensation reaction catalyst;

wherein the isocyanate-functional silicone-polyether copolymer is according to claim 1.

17. The sealant of claim 14, further comprising a filler, a cross-linker, an extender, a plasticizer, and an adhesion promotor.

18. A cured product of the sealant of claim 14.

19. A composite article comprising a substrate and the cured product of claim 18 disposed on the substrate.

20. 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 14.

21. 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 14.

13. A silicone-polyether-urethane copolymer having an average of more than one functional group of the following formula:

15. A sealant, comprising:

a silicone-polyether-urethane copolymer; and

a condensation reaction catalyst;

wherein the silicone-polyether-urethane copolymer is according to claim 13.

16. (canceled)