IP Library Granted Patent US 8,686,102
Granted Patent B2
US 8,686,102 · App. 12/288,974 · Granted Apr 1, 2014

Textiles treated with copolymers of epoxy compounds and amino silanes having enhanced wet-strength

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Quick Facts
Patent No.
US 8,686,102
App. No.
12/288,974
Granted
Apr 1, 2014
Kind
B2
Abstract

The present invention provides for textiles treated with a composition comprising the reaction product of e) an oxirane or oxetane compound comprising at least two oxirane or oxetane groups; and f) an amino silane having the formula: N(H)(R 1 )R 2 Si(OR 3 ) 3-a-b-c (OR 4 ) a (R 5 Si(OR 6 ) d (R 7 ) e ) b R 8 c with R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms; R 2 and R 5 are independently selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons; R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms; R 3 , R 6 , R 7 , and R 8 and are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms; the subscript b is zero or a positive number and has a value ranging from 0 to 3; the subscripts a, and c are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (a+b+c)≦3; and the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d+e)≦3, wherein the treated textile has enhanced wet strength.

Claims (161)

1. A treated textile treated with a composition consisting essentially of the reaction product of

a) an oxirane or oxetane compound comprising only two oxirane or oxetane endcapping groups; and

b) an amino silane having the formula:

N(H)(R 1 )R 2 Si(OR 3 ) 3-a-b-c (OR 4 ) a (R 5 Si(OR 6 ) d (R 7 ) e ) b R 8 c

with R 1 is H;

R 2 is selected from a group consisting of a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;

R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms;

R 5 is selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;

R 3 , R 6 , R 7 , and R 8 and are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms;

the subscript b is zero or a positive number and has a value ranging from 0 to 3;

the subscripts a, and c are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (a+b+c)≦3;

the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d+e)=3, wherein said reaction product is a linear [AB] type diblock copolymer of said oxirane or oxetane and said amino silane, and wherein said treated textile has enhanced wet strength, wherein A represents the oxetane or oxirane block and B represents the aminosilane block.

2. The treated textile of claim 1 where the oxirane or oxetane compound is selected from the group consisting of siloxanes, hydrocarbons and polyethers.

3. The treated textile of claim 2 where the oxirane or oxetane compound is a siloxane having the formula:

M f M E h M PE i M H j D k D E l D PE m D H n T o T E p T PE q T H r Q s with

M=R 9 R 10 R 11 SiO 1/2 ;

M H =R 12 R 13 H SiO 1/2 ;

M PE =R 12 R 13 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 1/2 ;

M E =R 12 R 13 (R E )SiO 1/2

D=R 18 R 19 SiO 2/2 ; and

D H =R 20 HSiO 2/2

D PE =R 20 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 2/2

D E =R 20 R E SiO 2/2

T=R 21 SiO 3/2 ;

T H =HSiO 3/2 ;

T PE =(—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 3/2 ;

T E =R E SiO 3/2 ; and

Q=SiO 4/2 ;

where R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;

R 14 is H or a 1 to 6 carbon atom alkyl group; R 15 is a divalent alkyl radical of 1 to 6 carbons; R 16 is selected from the group of divalent radicals consisting of —C 2 H 4 O—, —C 3 H 6 O—, and —C 4 H 8 O—; R 17 is selected from the group consisting of H, monofunctional hydrocarbon radicals of 1 to 6 carbons, and acetyl;

R E is independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from two to sixty carbon atoms;

the subscript f may be zero or positive subject to the limitation that when the subscript f is zero, h must be positive;

the subscript h is zero or positive subject to the limitations that when h is zero, the subscript f is positive, and that the sum of the subscripts h, l and p is positive;

the subscript k is zero or positive and has a value ranging from about 0 to about 1,000;

the subscript l is zero or positive and has a value ranging from about 0 to about 400 subject to the limitation that the sum of the subscripts h, l and p is positive;

the subscript o is zero or positive and has a value ranging from 0 to about 50;

the subscript p is zero or positive and has a value ranging from 0 to about 30 subject to the limitation that the sum of the subscripts h, l and p is positive;

the subscript s is zero or positive and has a value ranging from 0 to about 20;

the subscript i is zero or positive and has a value ranging from 0 to about 20;

the subscript m is zero or positive and has a value ranging from 0 to about 200;

the subscript q is zero or positive and has a value ranging from 0 to about 30;

the subscript j is zero or positive and has a value ranging from 0 to about 2;

the subscript n is zero or positive and has a value ranging from 0 to about 20;

the subscript r is zero or positive and has a value ranging from 0 to about 30;

the subscript t is zero or one;

the subscript u is zero or one;

the subscript v is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0;

the subscript w is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0; and

the subscript x is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0.

4. The treated textile of claim 1 where the oxirane or oxetane compound is a hydrocarbon having the formula:

R 22 y (R 23 ) z (R 24 α )(R 25 ) β

where R 22 and R 25 are independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;

R 23 and R 24 are each selected from the group consisting of a linear and a branched divalent hydrocarbon radical of 1 to 1000 carbons;

the subscripts y, z, α, β are zero or positive ranging from zero to four subject to the limitation that (y+β)=2.

5. The treated textile of claim 2 where the oxirane or oxetane compound is a polyether having the formula:

R 26 O(R 27 ) γ (C 2 H 4 O) δ (C 3 H 6 O) ε (C 4 H 8 O) ζ R 28

where R 26 and R 28 are independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;

R 27 is selected from the group of divalent radicals consisting of —C 2 H 4 O—, —C 3 H 6 O—, and —C 4 H 8 O—;

the subscript γ is zero or 1;

the subscript δ is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (δ+ε+ζ)>0;

the subscript ε is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (δ+ε+ζ)>0;

the subscript ζ is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (δ+ε+ζ)>0.

6. The treated textile of claim 3 wherein the composition producing said reaction product further comprises a compound having the formula:

R 29 (R 30 ) κ Si(OR 31 ) 3-η-θ (R 32 ) η (OR 33 ) θ

where R 29 is a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;

R 30 is a divalent hydrocarbon radical consisting of 1-60 carbons and the subscript κ has a value of zero or 1; R 31 and R 32 are independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 60 carbon atoms;

the subscript η is zero or positive and has a value ranging from 0 to 3;

the subscript θ is greater than 0 and less than or equal to 3, subject to the limitation that 3−η−θ is greater than or equal to zero; and

R 33 is a hydrocarbon radical that contains 3 to 200 carbon atoms.

7. The treated textile of claim 6 wherein

R 2 has from one to ten carbon atoms;

R 4 has from three to ten carbon atoms;

R 3 , R 6 , R 7 , and R 8 each independently have from one to twenty carbon atoms;

the subscript a ranges from 1 to 3;

the subscript b ranges from 0 to 25;

the subscript c ranges from 0 to 3;

R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to four carbon atoms;

the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 200;

the subscript k ranges from 0-500;

the subscripts v, w, and x each independently range from 0 to 50;

R 31 and R 32 each independently have from one to ten carbon atoms and

R 33 has from three to one hundred carbon atoms.

8. The treated textile of claim 6 wherein

R 2 has from two to eight carbon atoms;

R 4 has from three to eight carbon atoms;

R 3 , R 6 , R 7 , and R 8 each independently have from one to fifteen carbon atoms;

the subscript a ranges from 2 to 3;

the subscript b ranges from 0 to 15;

the subscript c ranges from 0 to 2;

R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to three carbon atoms;

the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 100;

the subscript k ranges from 5-250;

the subscripts v, w, and x each independently range from 0 to 35;

R 31 and 32 each independently have from one to eight carbon atoms and

R 33 has from three to fifty carbon atoms.

9. The treated textile of claim 6 wherein

R 2 has from two to five carbon atoms;

R 4 has from three to five carbon atoms;

R 3 , R 6 , R 7 , and R 8 each independently have from two to eight carbon atoms;

the subscript a is 3;

the subscript b is 0;

the subscript c is 0;

R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently methyl;

the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 50;

the subscript k ranges from 5 to 150;

the subscripts v, w, and x each independently range from 0 to 25;

R 31 and 32 each independently have from one to four carbon atoms and

R 33 has from three to ten carbon atoms.

10. The treated textile of claim 7 wherein

R 2 has from one to five carbon atoms;

R 4 has from three to five carbon atoms;

R 3 , R 6 , R 7 , and R 8 each independently have from two to eight carbon atoms;

the subscript a ranges from 1 to 2;

the subscript b ranges from 0 to 15;

the subscript c ranges from 1 to 3;

R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to three carbon atoms;

the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 50;

the subscript k ranges from 5 to 150;

the subscripts v, w, and x each independently range from 1 to 10;

R 31 and 32 each independently have from one to four carbon atoms and

R 33 has from three to fifty carbon atoms.

11. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 1 .

12. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 2 .

13. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 3 .

14. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the composition of claim 4 .

15. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the composition of claim 5 .

16. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 6 .

17. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 7 .

18. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 8 .

19. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 9 .

20. A treated textile treated with an aqueous emulsion where the discontinuous phase comprises water and the emulsion comprises the copolymer of claim 10 .

21. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the copolymer of claim 1 .

22. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the copolymer of claim 2 .

23. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the copolymer of claim 3 .

24. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 4 .

25. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 5 .

26. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 6 .

27. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 7 .

28. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 8 .

29. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 9 .

30. A treated textile treated with an aqueous emulsion where the continuous phase comprises water and the emulsion comprises the composition of claim 10 .

31. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the emulsion comprises the composition of claim 1 .

32. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 2 .

33. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 3 .

34. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 4 .

35. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 5 .

36. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 6 .

37. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 7 .

38. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 8 .

39. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 9 .

40. A treated textile treated with a non-aqueous emulsion where the discontinuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 10 .

41. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 1 .

42. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 2 .

43. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 3 .

44. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 4 .

45. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 5 .

46. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 6 .

47. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 7 .

48. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 8 .

49. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 9 .

50. A treated textile treated with a non-aqueous emulsion where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the emulsion comprises the composition of claim 10 .

Assignments (15)
RELEASE OF SECURITY INTEREST Recorded Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →
SECURITY AGREEMENT Recorded Jul 1, 2009
From: MOMENTIVE PERFORMANCE MATERIALS, INC.; JUNIPER BOND HOLDINGS I LLC; JUNIPER BOND HOLDINGS II LLC; JUNIPER BOND HOLDINGS III LLC; JUNIPER BOND HOLDINGS IV LLC; MOMENTIVE PERFORMANCE MATERIALS CHINA SPV INC.; MOMENTIVE PERFORMANCE MATERIALS QUARTZ, INC.; MOMENTIVE PERFORMANCE MATERIALS SOUTH AMERICA INC.; MOMENTIVE PERFORMANCE MATERIALS USA INC.; MOMENTIVE PERFORMANCE MATERIALS WORLDWIDE INC.; MPM SILICONES, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 022902/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2008
From: FALK, BENJAMIN; BRIJMOHAN, SMITA
To: MOMENTIVE PERFORMANCE MATERIALS, INC.
Reel/Frame 021811/0556 →