IP Library Granted Patent US 7,524,915
Granted Patent B2
US 7,524,915 · App. 11/260,598 · Granted Apr 28, 2009

Process for making moisture-curable silylated resin composition, the resulting composition and moisture-curable products containing the composition

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 7,524,915
App. No.
11/260,598
Granted
Apr 28, 2009
Kind
B2
Abstract

A process is provided for making a moisture-curable silylated resin composition by reacting (i) at least one polyol, (ii) at least one polyisocyanate and (iii) at least one isocyanatosilane, optionally in the presence of catalyst, wherein the NCO/OH ratio is less than 1. The resulting moisture-curable silylated resin composition is useful in the manufacturer of each product as moisture-curable sealants, coatings and adhesives.

Claims (15)

1. A process for making a moisture-curable silylated resin composition comprising reacting in the presence or absence of catalyst at least one polyether polyol (i), at least one polyisocyanate (ii) and at least one isocyanatosilane (iii), the NCO/OH ratio of the polyisocyanate (ii) and the polyol (i) being from about 0.1 to about 0.9 and the NCO/OH ratio of the isocyanatosilane (iii) and polyol (i) being from about 0.9 to about 0.1, provided, when hydroxyl-terminated polyurethane prepolymer prior to completion of the polyurethane prepolymer-forming reaction wherein the hydroxyl-terminated polyurethane prepolymer reaction medium has an isocyanate concentration of at least 0.03 % NCO, isocyanatosilane (iii) is added to the reaction medium to produce silylated polyurethane and wherein the process is a two-step process comprising:

(1) reacting polyol (i) with part of polyisocyanate (ii); and

(2) reacting the composition of step (1) with the remaining part of polyisocyanate (ii) and all of isocyanatosilane (iii).

2. The process for making a moisture-curable silylated resin composition according to claim 1 wherein the hydroxyl-terminated polyurethane prepolymer reaction medium has an isocyanate concentration of about 0.06 % to about 0.08 % NCO.

3. The process for making a moisture-curable silylated resin composition according to claim 1 wherein the NCO/OH ratio of the polyisocyanate (ii) and the polyol (i) is between about 0.4 and about 0.75.

4. The process for making a moisture-curable silylated resin composition according to claim 1 wherein polyol (i) is a polyether diol, polyisocyanate (ii) is a diisocyanate and isocyanatosilane (iii) possesses a single isocyanate group.

5. The process for making a moisture-curable silylated resin composition according to claim 4 wherein the polyether diol is a polypropylene ether diol.

6. The process for making a moisture-curable silylated resin composition according to claim 4 wherein the polyol is a polypropylene ether diol having a number average molecular weight between about 2,000 and about 20,000.

7. The process for making a moisture-curable silylated resin composition according to claim 6 wherein the polyol is a polypropylene ether diol having a number average molecular weight of at least about 4,000.

8. The process for making a moisture-curable silylated resin composition according to claim 6 wherein the polyol is a polypropylene ether diol having a number average molecular weight of at least about 8,000.

9. The process for making a moisture-curable silylated resin composition according to claim 4 wherein the diisocyanate is selected from the group consisting of ethylene diisocyanate, 1,6-hexamethylene diisocyanate, isophorone diisocyanate, cylcohexane-1,4-disocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,4-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, polymeric diphenylmethane diisocyanate, cyclohexane diisocyanate, phenylene diisocyanate and mixtures thereof.

10. The process for making a moisture-curable silylated resin composition according to claim 4 wherein the isocyanatosilane (iii) corresponds to the general formula

OCN—R 1 —Si(R 2 ) n (OR 3 ) 3-n

in which R 1 is an alkylene group having from 1-10 carbon atoms, R 2 and R 3 each are the same or different alkyl groups having from 1-10 carbon atoms, and n is 0, 1 or 2.

11. The process for making a moisture-curable silylated resin composition according to claim 10 wherein the isocyanatosilane is selected from the group consisting of 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane and mixtures thereof.

Assignments (27)
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 Apr 2, 2008
From: GENERAL ELECTRIC COMPANY
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 020742/0441 →
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 Mar 20, 2006
From: HUANG, MISTY; MEDICINO, FRANK D.; YANG, YURUN; NESHEIWAT, JERIES I.; O'KEEFE, BRENDAN J.
To: GENERAL ELECTRIC COMPANY
Reel/Frame 017351/0708 →