IP Library Granted Patent US 7,517,929
Granted Patent B2
US 7,517,929 · App. 11/003,077 · Granted Apr 14, 2009

Star-branched silicone polymers as anti-mist additives for coating applications

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,517,929
App. No.
11/003,077
Granted
Apr 14, 2009
Kind
B2
Abstract

A hydrido-silicone resin is incompletely reacted with an olefin under hydrosilylation conditions to produce a partially substituted hydrido-silicone that is further reacted under hydrosilylation conditions with a vinyl containing silicone to consume the remaining hydride species to produce a composition that is useful as an anti-mist agent in the coating of flexible supports.

Claims (93)

1. A composition comprising the reaction product of:

M a M Vi b D c D Vi d T e T Vi f and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T n T H o−i ) p Q) q ,

in the presence of a noble metal hydrosilylation catalyst wherein

M=R 2 R 3 R 4 SiO 1/2 ;

M Vi =R Vi R 5 R 6 SiO 1/2 ;

M H =HR 5 R 6 SiO 1/2 ;

M′=(R 1 CH 2 CH 2 )R 5 R 6 SiO 1/2 ;

D=R 7 R 8 SiO 2/2 ;

D Vi =R Vi R 10 SiO 2/2 ;

D H =HR 9 SiO 2/2 ;

D′=(R 1 CH 2 CH 2 )R 9 O 2/2 ;

T=R 11 SiO 3/2 ;

T Vi =R Vi SiO 3/2 ;

T H =HSiO 3/2 ;

T′=(R 1 CH 2 CH 2 )SiO 3/2 ;

Q=SiO 4/2 ;

each R 1 is a monovalent radical selected from the group consisting of halogens, hydrogen and C1 to C60 monovalent hydrocarbon radicals, polyesters, nitriles, alkyl halides and polyethers; each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group of C1 to C60 monovalent hydrocarbon radicals; each R Vi is independently selected from the group of C2 to 60 monovalent alkenyl hydrocarbon radicals; the subscripts a, b c, d, e, f, g, h, i, j, k, l, m, n, and o are zero or positive, and p and q are non-zero and positive, for the mixtures of compounds the average values of each of the subscripts will be integral or non-integral, for specific compounds the subscripts will be integral, with the proviso:

k+m+o−g−h−i<b+d+f;

p ranges from 0.4 to 4.0;

(b+d+f)/(((k+m+o−g−h−i)p)q) ranges from 4.59 to 0.25;

the sum of the subscripts a+b ranges from 2 to 12;

c+d ranges from 0 to 1000;

e+f ranges from 0 to 10;

g+h+i is 1 or greater;

and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T n T H o−i ) p Q) q is the reaction product of: ((M j M H k D l D H m T n T H o ) p Q) q and α CH 2 ═CHR 1

wherein α+1≦k+m+o; and 1.5≦k+m+o−g−h−i<100 and each CH 2 ═CHR 1 is styrene.

2. The composition of claim 1 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is methyl.

3. The composition of claim 1 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is selected from the group consisting C30 to C60 monovalent hydrocarbon radicals, C30 to C60 monovalent polyester radicals, C30 to C60 monovalent nitrile radicals, C30 to C60 monovalent alkyl halide radicals, C30 to C60 monovalent polyester radicals and mixtures thereof.

4. A composition to reduce misting during the coating of flexible supports comprising the reaction product of claim 1 .

5. The composition of claim 4 wherein each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is selected from the group consisting of C30 to C60 monovalent hydrocarbon radicals, C30 to C60 monovalent polyester radicals, C30 to C60 monovalent nitrile radicals, C30 to C60 monovalent alkyl halide radicals, C30 to C60 monovalent polyether radicals and mixtures thereof.

6. A process to reduce misting in the coating of a flexible substrate said process comprising preparing a silicone-containing coating composition for coating said substrate and adding thereto the composition of claim 1 .

7. A composition comprising the reaction product of:

M a M Vi b D c D Vi d T e T Vi f and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T′ i T n T H o−i ) p Q) q ,

in the presence of a noble metal hydrosilylation catalyst wherein

M=R 2 R 3 R 4 SiO 1/2 ;

M Vi =R Vi R 5 R 6 SiO 1/2 ;

M H =HR 5 R 6 SiO 1/2 ;

M′=(R 1 CH 2 CH 2 )R 5 R 6 SiO 1/2 ;

D=R 7 R 8 SiO 2/2 ;

D Vi =R Vi R 10 SiO 2/2 ;

D H =HR 9 SiO 2/2 ;

D′=(R 1 CH 2 CH 2 )R 9 O 2/2 ;

T=R 11 SiO 3/2 ;

T Vi =R Vi SiO 3/2 ;

T H =HSiO 3/2 ;

T′=(R 1 CH 2 CH 2 )SiO 3/2 ;

Q=SiO 4/2 ; wherein R 1 is selected from the group consisting of C15 to C60 monovalent hydrocarbon radicals, C15 to C60 monovalent polyester radicals, C15 to C60 monovalent nitrile radicals, C15 to C60 monovalent alkyl halide radicals, C15 to C60 monovalent polyether radicals and mixtures thereof; each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group of C1 to C60 monovalent hydrocarbon radicals; each R Vi is independently selected from the group of C2 to C60 monovalent alkenyl hydrocarbon radicals; the subscripts a, b c. d, e, f. h, i, j, l, m, n, and o are zero or positive, g and k are positive and p and q are non-zero and positive, for the mixtures of compounds the average values of each of the subscripts will be integral or non-integral, for specific compounds the subscripts will be integral, with the proviso:

k=m=o−g−h−i<b=d=f;

ranges from 0.4 to 4.0;

(b=d=f)/(((k=m=o−g−h−i)p)q) ranges from 4.59 to 0.25;

the sum of the subscripts a=b ranges from 2 to 12;

c=d ranges from 0 to 1000;

e=f ranges from 0 to 10;

g=h=i is 1 or greater;

and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T n T H o−i ) p Q) q is the reaction product of:

((M j M H k D l D H m T n T H o ) p Q) q and α CH 2 ═CHR 1 ,

wherein α=1≦k=m=o; and 1.5≦k=m=o−g−h−i<100.

8. The composition of claim 7 wherein R 1 is selected from the group consisting of C30 to C60 monovalent hydrocarbon radicals, C30 to C60 monovalent polyester radicals, C30 to C60 monovalent nitrile radicals, C30 to C60 monovalent alkyl halide radicals, C30 to C60 monovalent polyether radicals and mixtures thereof.

9. A composition to reduce misting during the coating of flexible supports comprising the reaction product of claim 7 .

10. The composition of claim 7 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is methyl.

11. The composition of claim 8 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is methyl.

12. A process to reduce misting in the coating of a flexible substrate said process comprising preparing a silicone-containing coating composition for coating said substrate and adding thereto the composition of claim 7 .

13. A composition comprising the reaction product of:

M a M Vi b D c D Vi d T e T Vi f and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T′ i T n T H o−i ) p Q) q ,

in the presence of a noble metal hydrosilylation catalyst wherein

M=R 2 R 3 R 4 SiO 1/2 ;

M Vi =R Vi R 5 R 6 SiO 1/2 ;

M H =HR 5 R 6 SiO 1/2 ;

M′=(R 1 CH 2 CH 2 )R 5 R 6 SiO 1/2 ;

D=R 7 R 8 SiO 2/2 ;

D Vi =R Vi R 10 SiO 2/2 ;

D H =HR 9 SiO 2/2 ;

D′=(R 1 CH 2 CH 2 )R 9 O 2/2 ;

T=R 11 SiO 3/2 ;

T Vi =R Vi SiO 3/2 ;

T H =HSiO 3/2 ;

T′=(R 1 CH 2 CH 2 )SiO 3/2 ;

Q=SiO 4/2 ;

wherein R 1 is selected from the group consisting of C15 to C60 monovalent hydrocarbon radicals, C15 to C60 monovalent polyester radicals, C15 to C60 monovalent nitrile radicals, C15 to C60 monovalent alkyl halide radicals, C15 to C60 monovalent polyether radicals and mixtures thereof; each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is independently selected from the group of C1 to C60 monovalent hydrocarbon radicals; each R Vi is independently selected from the group of C2 to C60 monovalent alkenyl hydrocarbon radicals; the subscripts a, b c, d, e, f, j, l, n are zero or positive, g and k are positive, h, i, m and o are zero and p and q are non-zero and positive, for the mixtures of compounds the average values of each of the subscripts will be integral or non-integral, for specific compounds the subscripts will be integral, with the proviso:

k=m=o−g−h−i<b=d=f;

ranges from 0.4 to 4.0;

(b=d=f)/(((k=m=o−g−h−i)p)q) ranges from 4.59 to 0.25;

the sum of the subscripts a=b ranges from 2 to 12;

c=d ranges from 0 to 1000;

e=f ranges from 0 to 10;

g=h=i is 1 or greater;

and ((M′ g M j M H k−g D′ h D l D H m−h T′ i T n T H o−i ) p Q) q is the reaction product of:

((M j M H k D l D H m T n T H o ) p Q) q and α CH 2 ═CHR 1 .

14. The composition of claim 13 wherein 1 is zero.

15. The composition of claim 13 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is methyl.

16. The composition of claim 13 wherein each CH 2 ═CHR 1 is styrene.

17. The composition of claim 16 where each R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 is methyl.

18. A process to reduce misting in the coating of a flexible substrate said process comprising preparing a silicone-containing coating composition for coating said substrate and adding thereto the composition of claim 13 .

Assignments (28)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
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 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
Reel/Frame 054387/0001 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
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 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
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 →
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 →
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 →
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 →
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 Aug 15, 2007
From: GENERAL ELECTRIC COMPANY
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 019698/0473 →
SECURITY AGREEMENT Recorded Jul 3, 2007
From: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 019511/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 1, 2005
From: KILGOUR, JOHN ALFRED; CUA, EDWIN C.; CUMMINGS, JOHN A.
To: GENERAL ELECTRIC COMPANY
Reel/Frame 016419/0838 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2004
From: KILGOUR, JOHN ALFRED; CUA, EDWIN C.; CUMMINGS, JOHN A.
To: GENERAL ELECTRIC COMPANY
Reel/Frame 016064/0222 →