Silicone-polycarbonate copolymer, sealants comprising same, and related methods

Patent metadata

Field	Value
Publication number	US-2022081515-A1
Application number	US-201917416473-A
Country	US
Kind code	A1
Filing date	Dec 16, 2019
Priority date	Dec 21, 2018
Publication date	Mar 17, 2022
Grant date	—

Abstract

A silicone-polycarbonate copolymer has the formula Xg[ZjYo]c, where each X is an independently selected silicone moiety having a particular structure, each Y is an independently selected polycarbonate moiety, each Z is an independently selected siloxane moiety, subscript c is from 1 to 150, subscript g is >1, 0≤j<2, and 0<o<2, with the proviso that j+o=2 in each moiety indicated by subscript c. Methods of preparing the silicone-polycarbonate copolymer are also disclosed. Further, a sealant is disclosed, the sealant comprising the silicone-polycarbonate copolymer and a condensation-reaction catalyst.

First claim

1 . A silicone-polycarbonate copolymer having the formula X g [Z j Y o ] c , wherein each X is independently a silicone moiety having one of formulas (I) or (II):

each Y comprises an independently selected polycarbonate moiety, and each Z is an independently selected siloxane moiety having the formula [R 1 h SiO (4−h)/2 ] d ,
where each R 1 is an independently selected substituted or unsubstituted hydrocarbyl group having from 1 to 18 carbon atoms; each R 2 is an independently selected substituted or unsubstituted hydrocarbyl group having from 1 to 18 carbon atoms; each D 1 is an independently selected divalent hydrocarbon group having from 2 to 18 carbon atoms; each subscript a is independently selected from 0 to 2; each subscript b is independently 0 or 1; subscript c is from 1 to 150; each subscript d is from 1 to 1000; each subscript e is independently 1 or 2; each subscript f is independently 0 or 1, with the proviso that within each X, when f is 1, b is 1; subscript g is >1; subscript h is independently selected from 0 to 2 in each moiety indicated by subscript d; each subscript j is independently ≥0 and <2; each subscript o is independently >0 and <2, with the proviso that j+o=2 in each moiety indicated by subscript c; subscript t is ≥0; and subscript u is >0.

2 . The silicone-polycarbonate copolymer of claim 1 , wherein the silicone-polycarbonate copolymer has the formula: [XA] g [Z j Y o ] c , wherein each silicone moiety X is bonded to one polycarbonate moiety Y or one siloxane moiety Z, if present, via A, wherein each A is independently selected from a covalent bond, -D 2 -O—C(═O)—NH—, and -D 2 -NH—C(═O)—NH—, where D 2 is a divalent group.

3 . The silicone-polycarbonate copolymer of claim 2 , wherein the silicone-polycarbonate copolymer has the formula:

wherein each X, Y, A, R 1 , subscript c, and subscript d is defined above.

4 . The silicone-polycarbonate copolymer of claim 2 , wherein j is 0 and the silicone-polycarbonate copolymer has the formula: X-A-Y 1 -A-X, where X and A are independently selected and defined above and Y 1 comprises a polycarbonate moiety.

5 . (canceled)

6 . The silicone-polycarbonate copolymer of claim 1 , wherein at least one Y further comprises at least one moiety in addition to and different from the polycarbonate moiety, and optionally, wherein the moiety is selected from an alkylaluminoxane moiety, an alkylgermoxane moiety, a polythioester moiety, a polyether moiety, a polythioether moiety, a polyacrylate moiety, a polyacrylonitrile moiety, a polyacrylamide moiety, a polyester moiety, an epoxy moiety, a polyurethane moiety, a polyurea moiety, a polyacetal moiety, a polyolefin moiety, a polyvinyl alcohol moiety, a polyvinyl ester moiety, a polyvinyl ether moiety, a polyvinyl ketone moiety, a polyisobutylene moiety, a polychloroprene moiety, a polyisoprene moiety, a polybutadiene moiety, a polyvinylidiene moiety, a polyfluorocarbon moiety, a polychlorinated hydrocarbon moiety, a polyalkyne moiety, a polyamide moiety, a polyimide moiety, a polyimidazole moiety, a polyoxazole moiety, a polyoxazine moiety, a polyoxidiazole moiety, a polythiazole moiety, a polysulfone moiety, a polysulfide moiety, a polyketone moiety, a polyetherketone moiety, a polyanhydride moiety, a polyamine moiety, a polyimine moiety, a polyphosphazene moiety, a polysaccharide moiety, a polypeptide moiety, a polyisocyanate moiety, a cellulosic moiety, and combinations thereof.

7 . The silicone-polycarbonate copolymer of claim 1 , wherein: (i) each R 1 is methyl; (ii) each R 2 is propyl; (iii) each subscript a is 0; (iv) each D 1 is C 2 H 4 ; or (v) any combination of (i) to (iv).

8 . A method of preparing a silicone-polycarbonate copolymer, said method comprising:
reacting a polycarbonate compound having on average more than one unsaturated group and an endcapping organosilicon compound in the presence of a hydrosilylation catalyst to give the silicone-polycarbonate copolymer; wherein the silicone-polycarbonate copolymer is the silicone-polycarbonate copolymer of claim 1 .

9 . The method of claim 8 , further comprising reacting, along with the polycarbonate compound and the endcapping organosilicon compound, at least one of: (i) a chain extending organosilicon compound and (ii) an organic compound having on average more than one terminal unsaturated group.

10 . The method of claim 8 , wherein the polycarbonate compound has the formula:
Y[R 4 ] i , wherein each R 4 is an independently selected unsaturated group having from 2 to 14 carbon atoms; subscript i is >1; and Y is a polycarbonate moiety.

11 . The method of claim 9 , further comprising reacting the chain extending organosilicon compound, and wherein the chain extending organosilicon compound comprises: (i) a linear silicon hydride functional organosilicon compound; (ii) a branched silicon hydride functional organosilicon compound; or (iii) both (i) and (ii).

12 . The method of claim 11 , wherein the chain extending organosilicon compound comprises the linear silicon hydride functional organosilicon compound, and wherein the linear silicon hydride functional organosilicon compound has the formula:

wherein each R 1 is an independently selected substituted or unsubstituted hydrocarbyl group having from 1 to 18 carbon atoms; and each subscript d′ is from 1 to 999.

13 . The method of claim 8 , wherein the endcapping organosilicon compound has formula (III) or (IV):

wherein each R 1 , R 2 , D 1 , subscript a, subscript b, subscript e, subscript f, subscript t, and subscript u are as defined above.

14 . (canceled)

15 . A method of preparing a silicone-polycarbonate copolymer, said method comprising:
reacting an organic compound having one terminal unsaturated group and one terminal hydroxyl group with an endcapping organosilicon compound in the presence of a hydrosilylation catalyst to give a hydroxyl-functional intermediate; reacting the hydroxyl-functional intermediate with a polyisocyanate to give an isocyanate-functional intermediate; and reacting the isocyanate-functional intermediate, a polycarbonate compound having on average more than one hydroxyl group, and optionally a polysiloxane having on average more than one hydroxyl group, to give the silicone-polycarbonate copolymer; wherein the silicone-polycarbonate copolymer is the silicone-polycarbonate copolymer of claim 1 .

16 . The method of claim 15 , wherein the endcapping organosilicon compound has formula (III) or (IV):

wherein each R 1 , R 2 , D 1 , subscript a, subscript b, subscript e, subscript f, subscript t, and subscript u are as defined above.

17 . (canceled)

18 . A sealant, comprising:
a silicone-polycarbonate copolymer; and a condensation reaction catalyst; wherein the silicone-polycarbonate copolymer is the silicone-polycarbonate copolymer of claim 1 .

19 . The sealant of claim 18 , further comprising: (i) a filler; (ii) a filler treating agent; (iii) a cross-linker; (iv) a surface modifier, (v) a drying agent; (vi) an extende

Assignees

• Dow Silicones Corp
• Dow Global Technologies Llc

Inventors

• Duquesne Emmanuel
• Grasmann Martin
• Harkness Brian
• Johnson William
• Santos Elizabeth
• Scherzer Justin
• Young Jeanette
• Zhu Bizhong

Classifications

• C08G77/448 Primary

  containing polycarbonate sequences · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G64/02

  Aliphatic polycarbonates · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title