IP Library Granted Patent US 11,098,198
Granted Patent B2
US 11,098,198 · App. 16/088,152 · Granted Aug 24, 2021

Siloxane-oxyalkylene copolymer surfactant compositions

Inventors: Juan Jesus Burdeniuc (Colmar, PA); Udo Banseberg (Stadtlohn, DE)
Assignee: Evonik Operations GmbH
C08L83/12C08G18/36C08G18/4837C08G18/61C08G18/7621C08G2110/005C08G2110/0008
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Quick Facts
Patent No.
US 11,098,198
App. No.
16/088,152
Granted
Aug 24, 2021
Kind
B2
Abstract

Siloxane-oxyalkylene copolymer surfactants in combination with alkyl esters of fatty acids are disclosed. Alkyl esters of fatty acids are represented by the general formula Z—COO—Y where Z is a saturated or unsaturated C 10-24 alkyl or alkylene group and Y is typically a C 1-6 alkyl, alkylene linear or branched group. The siloxane-oxyalkylene copolymer surfactants that are typically used with the fatty esters have the general formula MD x D′ y M wherein M represents (CH 3 ) 3 SiO 1/2 or R(CH 3 ) 2 SiO 1/2 , D represents (CH 3 ) 2 SiO 2/2 , D′ represents (CH 3 )RSiO 2/2 , and the value of x+y is from 50 to 220, and the ratio x/y is from 5 to 15 inclusive. In the above formulae for M and D′, R is a polyether-containing substituent. The siloxane-oxyalkylene copolymer surfactants used in conjunction with the fatty ester contains a major fraction (60-80 wt. %) of siloxane-oxyalkylene with one pendant R typically defined as C n H 2n O(C 2 H 4 O) a (C 3 H 6 O) b R′ moieties having weight average molecular weights of from about 1400-2000 and wherein n is 1-4 and typically 3, the values of “a” are in the range 12-22 and typically 16-20 and the values of “b” are in the range of 12-22 and typically 16-20, R′ typically represent acyl group —C(O)CH 3 . The surfactant of the invention also contains a minor fraction of a siloxane-oxyalkylene copolymer (6-10 wt. %) having two pendant R typically defined as C n H 2n O(C 2 H 4 O) a (C 3 H 6 O) b R′ moieties having average molecular weights of about 1000-3500 and wherein n is 1-4 and typically 3, the values of “a” are in the range 8-40 and typically 10-35 and the values of “b” are in the range of 8-40 and typically 10-35, R′ typically represent acyl group C(O)CH 3 .

Claims (14)

1. A composition comprising siloxane-oxyalkylene copolymers, at least one alkyl ester of a fatty acid comprising a methyl ester of rapeseed oil, and dipropylene glycol; wherein the siloxane-oxyalkylene copolymers have the general formula MD x D′ y M wherein M in each instance represents (CH 3 ) 3 SiO 1/2 or R(CH 3 ) 2 SiO 1/2 , D represents (CH 3 ) 2 SiO 2/2 , D′ represents (CH 3 )RSiO 2/2 , R in each instance is a polyether-containing substituent, the value of x+y is from 50 to 220, the ratio x/y is from 5 to 15 inclusive, and wherein the siloxane-oxyalkylene copolymers comprise

a) a first siloxane-oxyalkylene copolymer with a DP in the range of 110-130, a D/D′ in the range of 9-11, and an EO/PO molar ratio in the range of 1.0-1.05;

b) a second siloxane-oxyalkylene copolymer with a DP in the range of 190-210, a D/D′ in the range of 6-8, and an EO/PO molar ratio in the range of 1.0-1.05; and;

c) a third siloxane-oxyalkylene copolymer with a DP in the range of 60-80, a D/D′ in the range of 6-8, and an EO/PO molar ratio in the range of 1.0-1.05.

2. The composition of claim 1 wherein the siloxane-oxyalkylene copolymers include at least one siloxane-oxyalkylene copolymer comprising one pendant R moiety defined as C n H 2n O(C 2 H 4 O) a (C 3 H 6 O) b R 1 having a weight average molecular weight of from about 1400-2000 and wherein n is 1-4, the value of a is in the range of 12-22, the value of b is in the range of 12-22, and R′ is the acyl group C(O)CH 3 .

3. The composition of claim 1 wherein the siloxane-oyxalkylene copolymers include at least one siloxane-oxyalkylene copolymer comprising two pendant R moieties defined as C n H 2n O(C 2 H 4 O) a (C 3 H 6 O) b R′ having a weight average molecular weight of from about 1000-3500 and wherein n is 1-4, the value of a is in the range of 8-40, the value of b is in the range of 8-40, and R′ is the acyl group C(O)CH 3 .

4. The composition of claim 1 wherein the first siloxane-oxyalkylene copolymer comprises one pendant R moiety defined as C n H 2n O[C 2 H 3 (M)O] a R′, wherein M in the moiety C n H 2n O[C 2 H 3 (M)O] a R′ is H from ethylene oxide or methyl from propylene oxide, wherein the C n H 2n O[C 2 H 3 (M)O] a R′ moiety has a weight average molecular weight of from about 700-2500 and wherein n is 1-4, the value of a is in the range of 24-50, and R′ is the acyl group C(O)CH 3 .

5. The composition of claim 1 wherein the second siloxane-oxyalkylene copolymer comprises two pendant R moieties, wherein the first pendant R moiety is defined as C n H 2n O[C 2 H 3 (M)O] a R′, wherein M in the moiety C n H 2n O[C 2 H 3 (M)O] a R′ is H from ethylene oxide or methyl from propylene oxide, wherein the C n H 2n O[C 2 H 3 (M)O] a R′ moiety has a weight average molecular weight of from about 700-2500 and wherein n is 1-4, the value of a is in the range of 24-50, and R′ is the acyl group C(O)CH 3 , and the second pendant R moiety is defined as —C n H 2n O(C 2 H 4 O) a R′ having a weight average molecular weight of from about 2300-3200 and wherein n is 1-4, the value of a ace is in the range of 15-20, and R′ is the acyl group C(O)CH 3 .

6. The composition of claim 1 wherein the third siloxane-oxyalkylene copolymer comprises two pendant R moieties, wherein the first pendant R moiety is defined as C n H 2n O[C 2 H 3 (M)O] a R′, wherein M in the moiety C n H 2n O[C 2 H 3 (M)O] a R′ is H from ethylene oxide or methyl from propylene oxide, wherein the C n H 2n O[C 2 H 3 (M)O] a R′ moiety has a weight average molecular weight of from about 750-1800 and wherein n is 1-4, the value of a is in the range of 16-32, and R′ is the acyl group C(O)CH 3 , and the second pendant R moiety is defined as —C n H 2n O[C 2 H 3 (M)O] a R′, wherein M in the moiety C n H 2n O[C 2 H 3 (M)O] a R′ is H from ethylene oxide or methyl from propylene oxide, wherein the —C n H 2n O[C 2 H 3 (M)O] a R′ moiety has a weight average molecular weight of from about 2500-3500 and wherein n is 1-4, the value of a is in the range of 50-70, and R′ is the acyl group C(O)CH 3 .

7. The composition of claim 1 further comprising at least one alkyl ester of a fatty acid represented by the general formula Z—COO—Y wherein Z is a saturated or unsaturated C 10-24 alkyl or alkylene group, and Y is a C 1-6 alkyl group, alkylene group, linear group or branched group.

8. The composition of claim 1 further comprising at least one member selected from the group consisting of at least one polyol, at least one catalyst and at least one blowing agent.

9. A method for making a polyurethane foam comprising contacting the composition of claim 8 with at least one isocyanate.

10. A polyurethane foam made by the method of claim 9 .

11. The composition of claim 1 wherein the first siloxane-oxyalkylene copolymer is 50-70 wt % of the composition; the combination of the second siloxane-oxyalkylene copolymer, the third siloxane-oxyalkylene copolymer and dipropylene glycol is 10-20 wt % of the composition; and the methyl ester of rapeseed oil is 20-30 wt % of the composition.

Assignments (2)
CHANGE OF NAME Recorded Nov 26, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051135/0315 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2019
From: BURDENIUC, JUAN JESUS; BANSEBERG, UDO
To: EVONIK DEGUSSA GMBH
Reel/Frame 048953/0308 →
Continuity (2)
Provisional Application 62321363 · Apr 12, 2016
Related Publication 20200255665A1 · Aug 13, 2020
Cited By (1)
US 12,595,332