Organopolysiloxanes containing an unsaturated group

Patent metadata

Field	Value
Publication number	US-9493615-B2
Application number	US-201013520929-A
Country	US
Kind code	B2
Filing date	Dec 22, 2010
Priority date	Jan 6, 2010
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

The invention provides a composition comprising a polyolefin and a polyorganosiloxane in which at least 50 mole % of the siloxane units are D units as herein defined and which contains at least one unsaturated group, characterized in that the unsaturated group is group of the formula —X—CH═CH—R″ (I) or —X—C≡C—R″ (II), in which X represents a divalent organic linkage having an electron withdrawing effect with respect to the —CH═CH— or —C≡C— bond and/or containing an aromatic ring or a further olefinic double bond or acetylenic unsaturation, the aromatic ring or the further olefinic double bond or acetylenic unsaturation being conjugated with the olefinic unsaturation of —X—CH═CH—R″ or with the acetylenic unsaturation of —X—C≡C—R″ and R″ represents hydrogen or a group having an electron withdrawing effect or any other activation effect with respect to the —CH═CH— or —C≡C— bond.

First claim

The invention claimed is:

1. A composition comprising a polyolefin, a filler and a polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group) and which contains at least one sorbyloxyalkyl group of formula —X—CH═CH—R″, where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH—, the filler includes aluminium trihydroxide, magnesium dihydroxide, kaolin, non-hydrated, partially hydrated or hydrated fluorides, chlorides, bromides, iodides, chromates, hydroxides, phosphates, hydrogen phosphates, nitrates, oxides and sulphates of sodium, potassium, magnesium, calcium, and barium; zinc oxide, aluminium oxide, antimony pentoxide, antimony trioxide, beryllium oxide, chromium oxide, iron oxide, lithopone, boric acid or a borate salt, zinc borate, barium metaborate or aluminium borate, mixed metal oxides, aluminosilicate, vermiculite, silica including fumed silica, fused silica, precipitated silica, quartz, sand, and silica gel; rice hull ash, ceramic and glass beads, zeolites, aluminium flakes or powder, bronze powder, molybdenum, nickel, stainless steel powder, tungsten, hydrous calcium silicate, barium titanate, silica-carbon black composite, cement, fly ash, slate flour, bentonite, clay, talc, anthracite, apatite, attapulgite, boron nitride, cristobalite, diatomaceous earth, dolomite, ferrite, feldspar, graphite, calcined kaolin, molybdenum disulfide, perlite, pumice, pyrophyllite, sepiolite, zinc stannate, zinc sulfide or wollastonite.

2. A composition according to claim 1 , wherein the polyorganosiloxane comprises 2 to 2000 siloxane units and at least 90 mole % of the siloxane units are D units.

3. A composition according to claim 1 , wherein the polyorganosiloxane is a linear polydiorganosiloxane having terminal sorbyloxyalkyl groups of the formula —X—CH═CH—R″ (I) at both ends of the polydiorganosiloxane molecule.

4. A composition according to claim 1 , wherein the polyorganosiloxane has at least one pendant sorbyloxyalkyl group.

5. A composition according to claim 1 , wherein the sorbyloxyalkyl groups are bonded to the polyorganosiloxane by a C—Si bond.

6. A polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group) and which contains at least one sorbyloxyalkyl group of formula —X—CH═CH—R″ (I), where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH—.

7. A polyorganosiloxane according to claim 6 , wherein the sorbyloxyalkyl group is a sorbyloxypropyl group of formula CH 3 —CH═CH—CH═CH—C(═O)O—(CH 2 ) 3 .

8. A composition comprising a filler, 5 to 95% by weight of a polyolefin and 95 to 5% by weight of a polyorganosiloxane as defined in claim 6 , the filler includes aluminium trihydroxide, magnesium dihydroxide, kaolin, non-hydrated, partially hydrated or hydrated fluorides, chlorides, bromides, iodides, chromates, hydroxides, phosphates, hydrogen phosphates, nitrates, oxides and sulphates of sodium, potassium, magnesium, calcium, and barium; zinc oxide, aluminium oxide, antimony pentoxide, antimony trioxide, beryllium oxide, chromium oxide, iron oxide, lithopone, boric acid or a borate salt, zinc borate, barium metaborate or aluminium borate, mixed metal oxides, aluminosilicate, vermiculite, silica including fumed silica, fused silica, precipitated silica, quartz, sand, and silica gel; rice hull ash, ceramic and glass beads, zeolites, aluminium flakes or powder, bronze powder, molybdenum, nickel, stainless steel powder, tungsten, hydrous calcium silicate, barium titanate, silica-carbon black composite, cement, fly ash, slate flour, bentonite, clay, talc, anthracite, apatite, attapulgite, boron nitride, cristobalite, diatomaceous earth, dolomite, ferrite, feldspar, graphite, calcined kaolin, molybdenum disulfide, perlite, pumice, pyrophyllite, sepiolite, zinc stannate, zinc sulfide or wollastonite.

9. A composition according to claim 1 , wherein an organic peroxide compound capable of generating free radical sites in the polyolefin is present at 0.01 to 2% by weight of the total composition.

10. A process for the preparation of a polyorganosiloxane as claimed in claim 6 , wherein a polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group) and which contains at least one Si—OH group is reacted with an alkoxysilane containing a sorbyloxyalkyl group of formula —X—CH═CH—R″ (I), where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH—.

11. A process for grafting silicone onto a polyolefin, comprising reacting the polyolefin with a silicon compound containing an unsaturated group in the presence of means capable of generating free radical sites in the polyolefin, wherein the silicon compound is a polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group) and which contains at least one unsaturated group, wherein the unsaturated group is a sorbyloxyalkyl group of formula —X—CH═CH—R″ (I), where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH—.

12. A process according to claim 11 , wherein the polyorganosiloxane containing at least one unsaturated group is deposited on a filler before being reacted with the polyolefin.

13. A process according to claim 11 , wherein the polyolefin, the polyorganosiloxane containing at least one unsaturated group and a filler are reacted in situ.

14. A stabilised polymer blend comprising a polyolefin, a filler and a polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group), the polyorganosiloxane being at least partly grafted to the polyolefin by bonds formed by free radical polymerization of sorbyloxyalkyl groups, where the sorbyloxyalkyl groups have formula —X—CH═CH—R″ (I), where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH—.

15. A stabilised polymer blend comprising a polyolefin and a polyorganosiloxane in which at least 50 mole % of the siloxane units are R 2 SiO 2/2 (D units, in which each R represents an organic group or hydrogen or a hydroxyl group), the polyorganosiloxane being at least partly grafted to the polyolefin by bonds formed by free radical polymerization of a sorbyloxyalkyl group of formula —X—CH═CH—R″ (I), where X is C(═O)OR*, R* represents a divalent hydrocarbon moiety, and R″ represents CH 3 —CH═CH— in the polyorganosiloxane.

16. The stabilized polymer blend of claim 15 , wherein the sorbyloxyalkyl group is a sorbyloxypropyl group.

17. The stabilized polymer blend of claim 15 , where the polyolefin is polypropylene.

18. The stabilized polymer blend of claim 15 , wherein the sorbyloxyalkyl groups are bonded to the polyorganosiloxane by a C—Si bond.

19. The stabilized polymer blend of claim 18 , wherein the polyorganosiloxane is a linear polydiorganosiloxane having terminal sorbyloxyalkyl groups at both ends of the polydiorganosiloxane molecule.

20. The stabilized polymer blend of claim 18 , wherein the polyorganosiloxane has at least one pendant sorbyloxyalkyl group.

Assignees

• Backer Michael
• De Buyl Francois
• Deheunynck Damien
• Smits Valerie
• Dow Corning

Inventors

• Backer Michael
• De Buyl Francois
• Deheunynck Damien
• Smits Valerie

Classifications

• C08G77/16

  to hydroxy groups · CPC title

• C08L23/04

  Homopolymers or copolymers of ethene · CPC title

• C08G77/20 Primary

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08L23/10

  Homopolymers or copolymers of propene · CPC title

• C08L83/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers · CPC title