IP Library Granted Patent US 11,130,709
Granted Patent B2
US 11,130,709 · App. 14/716,139 · Granted Sep 28, 2021

Polyalkoxylated polyamine oxide defoaming compositions

Inventors: Lawrence L. Kuo (Acton, MA); Ying Chen (Arlington, MA)
Assignee: GCP Applied Technologies Inc.
C04B24/121C04B24/28C04B28/02C04B40/0039C08G73/024C09D179/02C04B2103/50C04B2111/00482
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Quick Facts
Patent No.
US 11,130,709
App. No.
14/716,139
Granted
Sep 28, 2021
Kind
B2
Abstract

The present invention provides a composition and method for controlling air voids in aqueous systems such as paints, coatings, sealants, adhesives, mastics, cements, mortar, masonry, or concrete, which comprises the reaction product of an oxidizing agent and a compound comprising at least one polyalkoxylated polyalkylene polyamine, at least one polyalkyoxylated polyethyleneimine, or a mixture thereof.

Claims (39)

1. A composition for modifying air in a cementitious composition, comprising:

the reaction product of at least one oxidizing agent and a compound comprising at least one polyalkoxylated polyalkylene polyamine represented by structural formula A

wherein

n represents an integer of 0 to 4;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 each individually represents a hydrogen, C 1 -C 6 alkyl group, —CH 2 —OH group, or -(AO) x -R 8 group, and wherein at least two of the -R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 represent an -(AO) x -R 8 group, provided that when n=0 then at least two of R 1 , R 2 , R 3 , R 4 , R 6 , and R 7 represent -(AO) x - R 8 ;

wherein AO represents an alkylene oxide group chosen from ethylene oxide, propylene oxide butylene oxide, or a mixture thereof;

wherein the relative molar amount of ethylene oxide compared to other alkylene oxide groups within AO is zero percent to less than fifty percent of the total;

wherein the total sum of the number of ethylene oxide and propylene oxide groups exceeds 25;

wherein x represents an integer of 26 to 100;

wherein R 8 represents hydrogen or a C 1 -C 6 alkyl group; and

wherein the reaction product of the at least one oxidizing agent and the compound comprising the at least one polyalkoxylated polyalkylene polyamine represented by structural Formula A is effective for modifying air within the cementitious composition and is devoid of a linear or branched alkyl group having greater than six carbon atoms which would function to entrain air within the cementitious composition.

2. The composition of claim 1 wherein the reaction product of the at least one oxidizing agent and the compound comprising the at least one polyalkoxylated polyalkylene polyamine is derived from polyalkoxylated product of ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, propylene diamine, dipropylene triamine, tripropylene tetramine, tetrapropylene pentamine, pentapropylene hexamine, N,N-dimethylethylene diamine, N,N′-dimethylethylene diamine, N,N-dimethylpropylene diamine, N,N′-dimethylpropylene diamine, N,N-diethylethylene diamine, N,N′-diethylethylene diamine, N,N-diethylpropylene diamine, N,N′-diethylpropylene diamine, or a mixture thereof.

3. The composition of claim 1 wherein the reaction product of the at least one oxidizing agent and compound comprising the at least one polyalkoxylated polyalkylene polyamine is derived from polyalkoxylated product of ethylene diamine, diethylene triamine, triethylene tetramine, or mixture thereof.

4. The composition of claim 3 wherein the reaction product of the at least one oxidizing agent and compound comprising the at least one polyalkoxylated polyalkylene polyamine is derived from polyalkoxylated ethylene diamine, diethylene triamine, or mixture thereof.

5. The composition of claim 1 wherein the at least one oxidizing agent for providing the reaction product is selected from the group consisting of hydrogen peroxide, performic acid, peracetic acid, perbenonzoic acid, chloroperoxybenzoic acid, monoperphthalic acid, perfsulfuric acid, molecular oxygen, ozone, or mixture thereof.

6. The composition of claim 1 wherein the at least one oxidizing agent for providing the reaction product is hydrogen peroxide.

7. An aqueous composition comprising an aqueous coating composition and the composition of claim 1 .

8. The composition of claim 1 further comprising a trialkanolamine, a lignosulfonate, a sulfonated naphthalene formaldehyde condensate, a sulfonated melamine formaldehyde condensate, an oxyalkylene-containing superplasticizer, an oxyalkylene-containing shrinkage reducing agent, or a mixture thereof.

9. A composition comprising a hydratable cementitious binder and the composition of claim 1 .

10. The composition of claim 1 further comprising an oxyalkylene-containing superplasticizer, an oxyalkylene-containing shrinkage reducing agent, or a mixture thereof.

11. The composition of claim 1 further comprising an oxyalkylene-containing superplasticizer.

12. The composition of claim 1 further comprising a set accelerator, a set retarder, or a mixture thereof.

13. The composition of claim 10 further comprising a set accelerator, a set retarder, or a mixture thereof.

14. The composition of claim 1 wherein ethylene oxide groups are present in the amount of 0% to 40% based on the total weight of polyethers in the polyalkoxylated polyalkylene polyamine.

15. The composition of claim 1 wherein 10 molar percent to 100 molar percent of amine groups of the polyalkoxylated polyalkylene polyamine is oxidized into amine oxide groups.

16. The composition of claim 1 wherein the reaction product has a molecular weight of 500 to 7,000.

17. The composition of claim 1 wherein the reaction product has a molecular weight of 1,000 to 6,000.

18. The composition of claim 1 wherein the reaction product has a molecular weight of 2,000 to 4,000.

19. A composition for modifying air in a cementitious composition, comprising:

the reaction product of at least one oxidizing agent and a compound comprising at least one alkoxylated polyethyleneimine represented by structural formula B,

-(AO) x (EI)y-  [Formula B],

wherein AO represents an alkylene oxide group selected from ethylene oxide, propylene oxide, butylene oxide, or a mixture thereof;

wherein the relative molar amount of ethylene oxide compared to other alkylene oxides within AO is less than fifty percent of the total;

wherein the total sum of the number of ethylene oxide and propylene oxide groups exceeds 25;

wherein x represents an integer of 26 to 100;

wherein EI represents repeating ethyleneimine units in a linear or branched structure;

wherein y represents an integer of 5 to 100;

wherein the relative number of AO chains per repeating ethyleneimine unit is 0.1 to 1.0; and

wherein the reaction product of the at least one oxidizing agent and the compound comprising the at least one alkoxylated polyethyleneimine represented by structural Formula B is effective for modifying air within the cementitious composition and is devoid of a linear or branched alkyl group having greater than six carbon atoms which would function to entrain air within the cementitious composition.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Sep 27, 2022
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: DE NEEF CONSTRUCTION CHEMICALS (US) INC.; VERIFI LLC; GCP APPLIED TECHNOLOGIES INC.
Reel/Frame 061553/0521 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER 13353676 PREVIOUSLY RECORDED ON REEL 037701 FRAME 0396. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 17, 2016
From: W. R. GRACE & CO.-CONN.
To: GCP APPLIED TECHNOLOGIES INC.
Reel/Frame 038289/0821 →
SECURITY INTEREST Recorded Mar 7, 2016
From: GCP APPLIED TECHNOLOGIES INC.
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 038012/0407 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2016
From: W. R. GRACE & CO.-CONN.
To: GCP APPLIED TECHNOLOGIES INC.
Reel/Frame 037701/0396 →