USRE36233E - Use of softening additives in polyurethane foam - Google Patents
Use of softening additives in polyurethane foam Download PDFInfo
- Publication number
- USRE36233E USRE36233E US09/086,816 US8681698A USRE36233E US RE36233 E USRE36233 E US RE36233E US 8681698 A US8681698 A US 8681698A US RE36233 E USRE36233 E US RE36233E
- Authority
- US
- United States
- Prior art keywords
- foam
- polyisocyanate
- agent
- pphp
- tertiary amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2036—Heterocyclic amines; Salts thereof containing one heterocyclic ring having at least three nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1816—Catalysts containing secondary or tertiary amines or salts thereof having carbocyclic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
Definitions
- N,N-Dimethyl cyclohexylamine (CAS 98-94-2) as an early stage co-catalyst in catalyst blends intended to produce trimerized isocyanate structures in foams (WO9216574).
- U.S. Pat. No. 4,101,466 discloses the general use of bis-(3-dimethylaminopropyl) methlylamine (CAS 3855-32-1) in polyurethane foams and U.S. Pat. No. 5,173,516 teaches the use of bis-(3-dimethylaminopropyl) methylamine as a processing aid for high resiliency (HR) foam systems.
- the catalyst N,N-dimethylpiperazine (CAS 106-58-1) (DMP) has been used primarily as a processing aid in polyester foams, though one patent citation (U.S. Pat. No.
- German Patent No. 4030515 discloses the use of 3-(dimethylamino)-1-propylamine (DMAPA) (CAS 109-55-7) to prepare catalysis useful in rigid polycther polyol foams. This catalyst has also been used to catalyze HR foams according to the teachings of DE2116535.
- DMAPA 3-(dimethylamino)-1-propylamine
- the present invention describes a new additive to be used in concert with all-water blown low index flexible polyurethane technology as a means of dramatically softening the resultant foams.
- These additive based foams yield similar or better physical properties than the higher IFD (harder) foams without the additive.
- this invention relates to the use of certain tertiary amine catalysts to reduce the IFD values (hardness properties) of flexible polyurethane slabstock foam prepared using conventional secondary hydroxyl polyether polyols. More particularly, this invention relates to these amine softening additives used in all-water-based foam formulations, particularly those or low isocyanate index ( ⁇ 100). These foams exhibit a substantially open cell structure without crushing and without the use or any ABA's such as chlorofluorocarbons, methylene chloride, or other halocarbons.
- the present invention is based on the unexpected findings that small amounts or certain amine foam additives dramatically soften low density all-water based flexible polyurethane foams while maintaining the other desirable properties of the foam, e.g., small cell size, acceptable compression, etc. and without significantly affecting processability.
- Polyurethane foam formulations contemplated herein are typically all-water-blown low index formulations using stabilizing additives such as those discussed in U.S. Pat. No. 4,950,694 to Hager, which is incorporated herein by reference.
- the amine additives for use herein are typically not used in conventional flexible slabstock foams.
- Most conventional secondary hydroxyl polyol based flexible slabstock foam amine catalyst packages rely heavily on blends of strong blowing and gelling catalysts such as bis(dimethylaminoethyl) ether and triethylenediamine (TEDA).
- the catalysts of this invention are relatively weak polyurethane catalysts in comparison and typically are used in rigid, molded, and/or high resiliency (HR) foams.
- Such catalysts have been used in rigid foams systems to promote isocyanate dimerization, trimerization, and (cyclo) trimerization as one method to help harden the foam systems or as HR molded or polyester based foam processing aids as means to control early stage foam exotherms and foam gelation as it relates to flow.
- HR molded or polyester based foam processing aids as means to control early stage foam exotherms and foam gelation as it relates to flow.
- the amine additives of this invention yield foam with equal or superior processing and physical properties to all-water based polyurethane foams while exhibiting very large IFD reductions of the foams incorporating them. These properties have been mostly observed with low density, soft foam (about 1 pcf pound per cubic foot! grades. High quality foams with IFD reductions of up to about 9 lb. as compared to foams without the amine additive have been seen in these 1 pcf foams upon the addition of small quantities of the amine additives of the present invention. Similar additions or small quantities of these amine additives to high density (about 1.8 pcf), soft foam grade, all-water based formulations have shown IFD reductions approaching about 2.5 lbs.
- the additives may be described by their affect of producing a useful flexible foam with a 25% IFD of 5 to 18 lbs., preferably 10 to 18 lbs. in lower density ( ⁇ 1.5 pcf) foam and 10 to 21 lbs., preferably 16 to 21 lbs. in higher density (>1.5 pcf) foam.
- 90% compression sets (measured according to ASTM 3574) of less than about 15% can be achieved with the present invention.
- Such magnitudes of IFD change with minor amounts of amine additives are surprising, especially given that some or these additives are used to harden rigid foam or are used mainly as processing aids.
- Cell Size is another important property in foam. A fine or small-sized cell structure is generally accepted as leading to a silky feel or hand of a given piece of foam. Additionally, the relative degree of regularity of the cell sizes also strongly contributes to foam physical properties such as tingemailing and compression sets in many foam grades. Highly desirable maximum cell sizes of less than about 2.0 mm are achieved in the present by disclosed foam formulation.
- Airflow data provides a numerical measure of the amount of air to flow through a standard size piece of foam at a standard air pressure and temperature. This gives a measure to the relative openness or closedness of a given piece of foam. Foams with higher airflows are more open and conversely those with lower airflows are considered closed or tighter. Airflows achieved in foams of the present invention are greater than about 80 cfm/ft 2 for 1.0 pcf foams and greater than about 30 cfm/ft 2 for higher density foam. Thus, the airflows of the presently disclosed foams are relatively high and indicate good quality open-celled foam. These airflow ranges are for non-FR (flame retardant) foam grades. FR foams would be, by definition, of lower airflows.
- Blow times are an important property of foam disclosed herein due to the mechanical processing limitations associated with the standard foam production equipment used in the industry. Since most commercial slabstock foam is produced on continuous equipment, it is desirable to have foam formulation blowoff times within pre-described ranges that are optimal for a given machine. Outside of the normal blowoff time windows (i.e., 75-180 sec. on most equipment), the production or useful foam in a continuous, consistent manner is problematic as throughputs, fallplate settings and catalyst levels, become extremely difficult to optimize, thus inhibiting the production these foam systems. Blow times of most of the presently disclosed foam formulations are in the range of about 75-180 seconds and most preferably around 100-140 seconds and thus, fall within the commercially necessary parameters. A few of the disclosed formulations are slightly below this 75 second limit and yet are believed to be close enough to said limit that further optimizations of all of the formulation components should bring these into the range of commercially producable foam.
- the flexible polyurethane slabstock foam contemplated herein is comprised of (I) one or more polyols; (II) one or more organic isocyanates; (III) blowing agents; (IV) one or more surface active agents; (V) one or more catalysts; (VI) one or more foam processing aids; (VII) amines softening additives; and (VIII) optionally, one or more of (VIII) other standard ingredients known to those skilled in the art. To follow is a description of each component of the invention.
- the polyols, Group (I), which can be utilized in the present invention include, but are not limited to, the following polyether polyols: (a) alkylene oxide adducts of polyhydroxyalkanes; (b) alkylene oxide adducts of non-reducing sugars and sugar derivatives; (c) alkylene oxide adducts of polyphenols; and (d) alkylene oxide adducts or polyamines and polyhydroxyamines.
- Alkylene oxides having two to four carbon atoms generally are employed, with propylene oxide, ethylene oxide and mixtures thereof being particularly preferred.
- any material having active hydrogens may be utilized to some extent and therefore is included within the broad definition of the polyols of Group (I).
- amine-terminated polyether polyols, hydroxyl-terminated polybutadiene polyols and many others are known and may be used as a minor component in combination with the above-identified conventional polyether polyols.
- the polyol compound (I) should have an equivalent weight in the range of about 400 to about 1500 grams/equivalent and an ethylene oxide content of less than 20%.
- the equivalent weight is in the range of about 500 to about 1300 grams/equivalent and most preferably between about 750 and 1250 grams/equivalent.
- the polyol or polyol blend should have an average hydroxy functionality of at least 2. The equivalent weight is determined from the measured hydroxyl number. The hydroxyl number is defined as the number of milligrams of potassium hydroxide required for the complete hydrolysis of the fully acetylated derivative prepared from one gram of polyol.
- polyols have hydroxyl numbers preferably in the range of about 43 to about 110, and more preferably in the range of about 45 to about 75.
- the polyols should include the poly(oxypropylene) and poly(oxyethylene-oxypropylene) triols.
- Ethylene oxide when used can be incorporated in any fashion along the polymer chain. Stated another ways the ethylene oxide can be incorporated either in internal blocks, as terminal blocks, or may be randomly distributed along the polyol chain.
- the manner of incorporation and the ethylene oxide content of the polyol preferably is as noted above.
- ethylene oxide is used at a level below about 20% by weight, preferably below about 15% by weight, and is located primarily within the interior of the polyol chain.
- the polyols are substantially secondary hydroxyls.
- a portion or all of the polyol component may be added in the form of a polyol polymer in which reactive monomers have been polymerized within a polyol to form a stable dispersion of the polymer solids within the polyol.
- the amount of polyol used is determined by the amount of product to be produced. Such amounts may be readily determined by one skilled in the art.
- Organic isocyanates (Group II) useful in producing polyurethane foam in accordance with this invention are organic compounds that contain, on average, between about one and a half and about six isocyanate groups, and preferably about two isocyanate groups.
- Suitable organic polyisocyanates include the hydrocarbon diisocyanates, e.g., the alkylene diisocyanates and the aryl diisocyanates and more specifically, diphenylmethane diisocyanate and toluene diisocyanate ("TDI").
- Preferred polyisocyanates are 2, 4 and 2, 6 toluene diisocyanates and their mixtures having a functionality of about 2, which are broadly referred to herein simply as TDI.
- the most preferred polyisocyanate is 80/20 TDI (i.e., a mixture of 80% 2,4-toluene diisocyanate and 20% 2,6-toluene diisocyanate).
- the amount of isocyanate to be used is dependent upon the index of foam desired and the final properties of the foam to be formed. As stated above, if the index is 100, then there is a stoichiometric equivalent of the amount of isocyanate needed to react with the polyol component (Group I) and the other active hydrogen containing components in the system. While the present invention may be practiced in a wide range of indexes, 60-120; however, the preferred range of use is indexes between 80 and 115; and most preferably the range of indexes is 85-95.
- Water (Component III) is preferably the sole blowing agent to produce carbon dioxide by reaction with isocyanate. Water should be used at about 1 to 12 pphp (parts per hundred of polyol (Group I)) and preferably between 2 and 10 pphp. At foam indexes below 100, the stoichiometric excess of water cools and blows via vaporization, not as part of the reaction to produce carbon dioxide.
- Other blowing agents that are conventionally used in the art may be used herein, but because of the utility of the formulation large amounts of such agents are no longer needed and in many cases none are needed at all.
- Suitable surface active agents for slabstock applications include "hydrolyzable” polysiloxane-polyoxyalkylene block copolymers.
- Another useful class of foam surface active agents are the "non-hydrolyzable” polysiloxane-polyoxyalkylene block copolymers.
- the latter class of copolymers differs from the above-mentioned polysiloxane-polyoxyalkylene block copolymers in that the polysiloxane moiety is bonded to the polyoxyalkylene moiety through direct carbon-to-silicon bonds, rather than through carbon-to-oxygen-to-silicon bonds.
- Most preferred are the silicone surfactants L-640, L-620 and L-603 commercially available from OSi Specialties, Inc. of Danbury, Conn.
- the surface active agent should be present at about 0.0001 percent to about 7-8 percent by weight of the total reaction mixture.
- component (v) is a combination of standard tertiary amine and organometallic polyurethane catalysts which should be present at about 0.0001 to 5 weight percent of the reaction mixture.
- Suitable catalysts include, but are not limited to, dialkyltin salts of carboxylic acid, tin salts of organic acids, triethylene diamine (TEDA), bis (2,2'-dimethylaminoethyl) ether and similar compounds that are well known to the art.
- a foam processing aid (Group VI) is used for enhancing the properties of low density, flexible slabstock foam, said foam processing aid includes a crosslinking agent and/or extending agent and preferably a sufficient amount of a cell opening agent, to yield a polyurethane foam having a porosity greater than about 40 cubic feet per minute per square foot (CFM-ft 2 ), although this is dependent on foam grade.
- a relatively low molecular weight (generally below about 250 gms/mole) polyfunctional glycol crosslinking/extending agent is preferred to make stable, free-rise foams.
- the equivalent weights of these agents are generally less than about 200, but in certain circumstances they may be higher.
- the reactive group functionality of these compounds should be at least two, and preferably in a mixture of agents, at least one has a functionality or three or greater.
- Polyfunctional isocyanate reactive compounds such as a hexahydroxy functional alkane of a molecular weight or approximately 182 gms/mole with an equivalent weight of 30, are preferred. The number of such functionalities may be greater than the limitation of eight.
- the polyols that are or use herein, unlike those previously described, may include primary polyols.
- the crosslinking/extending agent should be present between about 0.1 and 10 pphp and preferably, between 0.2 and 5 pphp.
- polyfunctional isocyanate reactive components may be used with the present invention.
- These include, other high molecular weight cross-linking agents that are polyvinyl alcohol homo- and copolymers of numerous monomers, including polyvinyl butyral, which has a molecular weight of 2,000-20,000, hydroxyethyl(meth)acrylate homo- and co-polymers of molecular weight 2,000-20,000, hydroxyl derivatives or polyvinyl ethers such as hydroxybutyl vinyl ether homo- and co-polymers of molecular weight 2,000-20,000 and similar polymers.
- These polymers may have equivalent weights greater than 200 which may be preferred in certain usages. Generally, the equivalent weight is between 50 and than 2,000. Moreover, the molecular weight of these polymers are from 2,000 to 20,000.
- the cell opening agent is preferably a polyethylene oxide monol or polyol of an equivalent weight greater than 200, with 200-1,000 being preferable, with a hydroxyl functionality of two or greater.
- one of the preferred cell opening agents is a polyethylene oxide adduct of glycerol of a molecular weight or about 990 gms/mole, with an equivalent weight of about 330.
- the cell opening agent should be present at about 0.001 to 20 pphp. Note that in certain cases despite the equivalent weight difference, the cell opener may act as a crosslinking agent and vice-versa, thereby reducing the need for the crosslinking agent or cell opening agent, as the case may be.
- the weight ratio of the cell opening agent to crosslinking agent present in the composition is critical and should be about 10:1 to 1:2, with 6:1 to 3:1 being preferable. Combinations of cell opening agent and crosslinking agent within this preferred range have a symbiotic effect on the foam. For example, when a cross-linking agent was used alone, foams were stable with no splits, but were tight with low air flow resulting in poor compression sets. If a cell opening agent is used alone the foam will be very open with center splits and possessed moderate compression sets at best. In the preferred range of ratios, combinations lead to spilt-free, stable open foams with low compression sets.
- the specific softening amine additives (VII) of this invention are tertiary amino polyisocyanate catalysts which contain at least one contiguous three (3) carbon chain, which is not interrupted by a non-carbon atom.
- Said polyisocyanate catalysts may be polyisocyanurate catalysts which cause crosslinking amongst the isocyanate groups.
- These catalysts also include some polyester foam and HR foam processing aids.
- These types of catalysts are well known in the art and the type of structures included therein have been known in the art. See, e.g. Malwitz, N. et.
- Exemplary for use herein are 1,3,5-tris-(3-dimethylaminopropyl)- 1,3,5-triazine (commercially available from OSi Specialties, Inc. of Danbury, Conn. under the trade name NIAX® C-41) and bis-(3-dimethylaminopropyl) methylamine (commercially available from Air Products of Allentown, Pa. under the trade name POLYCAT® 77).
- Other examples for use herein include 1, 4, Dimethylpiperazine (DMP) and dimethyl cyclohexyl amine (NIAX® C-8 available from OSi Specialties, Inc.). The choice of the particular additive depends upon the cell opener and crosslinking agent used in the composition.
- amine softening additives or additive blends are used in relatively small amounts 0.1 to about 2 pphp, in addition to normal tin and amine catalyst.
- Solid stabilizing polymers (VIII) and other additives, including flame retardants, colorants, dyes and anti-static agents, which are conventionally known in the art may be used with the formulations of the present invention.
- additives listed in U.S. Pat. No. 4,950,694 are exemplary and are incorporated herein.
- additives such as JEFFAMINE® amine terminated polyols (available from Texaco of Houston, Tex.) and more specifically, ethylene oxide, propylene oxide based block copolymers which are terminated with a primary amine.
- the required amount of toluene di-isocyanate is calculated from the amount of polyol, water, foam processing aid and the desired index.
- the polyol, surface active agent, amine catalyst, amine additive, water, foam processing aids, and other additives are mixed together and agitated. During such agitation, the organometallic catalyst and the isocyanate are added and mixing continues until homogeneous. When the mixing stops, the liquid foam mass is poured as quickly as possible into the desired form for the foam. Frequently, this is accomplished in a continuous process. After gas release starts occurring, the foam may be mechanically cooled.
- Polyol designates a 56 hydroxyl number polyalkylene triol (nominal) produced by reacting propylene oxide (90%) and ethylene oxide (10%) onto glycerin. This material has predominantly secondary terminal hydroxyl groups.
- TDI designates commercially available 80/20 mix of toluene diisocyanate isomers.
- Tin designates a standard commercial organotin catalyst.
- T-9 consisting mainly of stannous octoate.
- Amine designates a balanced blow and gel catalyst, typically NIAX® catalyst C-183 (available from OSi Specialties, Inc.).
- Silicone designates a standard commercial non-hydrolyzable surfactant (polyether-silicone copolymer) used for conventional slabstock foam, Silicone L-620, available from OSi Specialties, Inc.
- Modifier 1 designates Geolite® modifier GM-201 foam processing aid which contains 25% of water (commercially available from OSi Specialties, Inc.)
- Modifier 2 designates Geolite® modifier GM-205 which contains foam processing aid which contains 28% water. (Commercially available from OSi Specialties, Inc.)
- Modifier 3 comprises about 25% by weight, of water, about 64% polyethylene oxide adduct of glycerol of a molecular weight of about 990 gms/mole, with an equivalent weight of about 330, and about 11% hexahydroxy functional alkane of a molecular weight of about 182 gms/mole with an equivalent weight of about 30.
- Additive A designates ORTEGOL® 310 softening agent. (Available from Th. Goldschmidt of Hopewell, Va.)
- Additive B is Carapor 2001 softening agent. (Available from Shell of Houston, Tex.)
- Additive C is NIAX® C-41 catalyst. (Available from OSi Specialties, Inc.)
- Additive D is POLYCAT® 77 catalyst. (Available from Air Products.)
- Additive E is NIAX® C-8 catalyst. (Available from OSi Specialties, Inc.)
- Additive F is JEFFAMINE® ED-600 polyol. (Available from Texaco.)
- Additive G is 1,4-dimethylpiperazine. (Available from Aldrich of Milwaukee, Wis.)
- Additive H is dirnethylaminopropylamine. (Available from Aldrich.)
- Additive I is NIAX® catalyst A-1. (Available from OSi Specialties, Inc.)
- Additive J is NIAX® catalyst A-33. (Available from OSi Specialties, Inc.)
- Additive K is 3-Dimethylamino-N,N-dimethylpropionamide. (Available from Aldrich)
- Additive L is ARMEEN® DM-16D catalyst. (Available from Akzo of Chicago. Ill.)
- Additive M is NIAX® C-5 catalyst. (Available from OSi Specialties, Inc.)
- Additive N is tetramethyl-1,3-butanediamine. (Available from OSi Specialties, Inc.)
- Additive O is tetramethyl-1,3-ethylenediamine. (Available from Aldrich.)
- Splits indicates visible evidence and degree of splitting. This may appear as a surface or interior foam split. A relative measure of severity may proceed this descriptor.
- Cell Size indicates an actual measure of averaged cell size ranges using a hand-held magnifying eyepiece with internal metric ruler.
- % Settling indicates the percentage of foam height reduction at aborn the 4 minute post pour time relative to the maximum foam height during the first 3 minutes of foam rise.
- Fingernailing is a subjective industry test which involves pressing the tingemails deeply into the foam sample and visually judging the speed at which the foam recovers. Fast recovery is desirable and is designated by adjectives such as good or mild fingernailing. Fingernailing should be moderate to mild, though mild to non-existent is most preferred. All other physical property testing of foam samples were performed according to ASTM D-3574 with minor modifications.
- All of the all-water blown flexible foams were prepared using standard, box pour, hand mixture methods as described below.
- the polyol was weighed into a half gallon paper mixing cup, followed by surfactant, amine(s), additive(s), and lastly the distilled water. This mixture was thoroughly agitated for 60 or more seconds using a drill press based blade mixing system (at 2500 RPM) which was attached to the pre-programmed timer.
- the drill press stopped for 15 seconds after the initial mixing period (according to a pre-programmed schedule) in which time the pre-weighed amount of tin catalyst was added via syringe. The mixing then restarted and continued for 9 more seconds.
- the following two tables show the foam formulations and representative physical properties of various flexible polyurethane foams prepared using the amine softening additives and additive blends of the present invention. These foams are low index, all-water-based formulations Examples 1-11 are made according to the present invention. Comparative Examples A, I-R are shown for contrast to these examples. Example A is the same as in the previous set of examples.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
______________________________________ Formulations of Comparative Commercial Additive Foams Comparative Chemical Components Example A Examples of Foam Formulations Formulation B-H ______________________________________ Polyol 100 100 Water (added) 5.25 5.25 TDI-80 64.38 64.84-66.67* Index 85 85 Tin 0.1 0.1 Amine 0.18 0.18 Silicone 1.0 1.0 Modifier 1 5.0 5.0 Additive A -- 0.0-0.5 Additive B -- 0.0-0.5 ______________________________________ *depending on the reported hydroxyl numbers of the additives
__________________________________________________________________________ Physical properties of Comparative Commercial Additive Foams Air Flow, Degree of Foam Additive blow max. cell Density, 25% IFD comp. sets (AF) Finger- Designation Additive amt. pphp time, sec size, mm pcf lb. (%) cfm/sf nailing __________________________________________________________________________ A none ` 122 1.2 1.1 21.5 8.1 116 mild-moderate B A 0.1 126 1.4 1.1 21.0 36.2 140 moderate to server C A** 0.25 126 1.0 1.1 19.3 66.0 158 moderate D A 0.5 131 1.0 1.1 19.8 86.6 3 severe E B 0.1 124 1.5 1.1 18.5 40.0 126 moderate F* B 0.1 131 1.4 1.0 18.1 76.1 129 moderate to severe G B*** 0.25 131 1.4 1.1 15.0 88.3 4 severe H B 0.5 142 1.4 1.0 8.7 89.7 21 severe __________________________________________________________________________ repeat of comparative example E. A + B do not fall within the scope of invention **9.4% settling ***6.1% settling. All other foams ≦ 2% settling.
______________________________________ Formulations of Invention and Comparative Commercial Additive Foams Examples 1-11 and Chemical Components Comparative Comparative Examples of Foam Formulations Example A 1-R ______________________________________ Polyol 100 100 Water (added) 5.25 5.25 TDI-80 64.38 64.38 Index 85 85 Tin 0.1 0.1-0.13* Amine 0.18 0.0-0.18* Silicone 1.0 1.0 Modifier 1 5.0 5.0 Additive C -- 0.0-0.30 Additive D -- 0.0-0.25 Additive E -- 0.0--0.38 Additive F -- 0.0-0.5 Additives G-O -- 0.0-0.15 ______________________________________ *The catalyst levels of these formulations were slightly modified from foam to foam to produce testable, splitfree foam with the individual additives.
__________________________________________________________________________ Physical Properties of Additive Foams max. 90% Degree of Foam Add. amt. blow time, cell size, Dens., 25% comp. sets AF Finger- Designation Additive pphp sec mm pcf IFD lb. (%) cfm/sf nailing Comments __________________________________________________________________________ 1 D 0.15 114 1.2 1.1 15.6 11.4 126 mild. improved hand 2 D 0.25 99 1.0 1.1 16.7 11.5 115 mild- improved hand moderate 3 E 0.15 125 1.4 1.1 17.8 9.6 112 moderate- severe- 4 E with 0.38 95 1.3 1.0 12.9 12.0 81 moderate improved hand F 0.50 5 E with 0.15 121 1.1 1.1 18.5 13.8 175 mild- F 0.5 moderate 6 E with 0.10 100 1.1 1.0 13.8 23.0 109 mild- C 0.15 moderate 7 D with 0.25 101 1.3 1.0 15.1 11.8 152 mild- F 0.5 moderate 8 C with 0.15 109 0.9 1.0 16.1 14.2 218 mild- F 0.5 moderate 9 C 0.3 93 1.2 1.0 14.4 12.9 179 mild- moderate 10 G 0.15 110 1.5 1.1 18.5 14.3 121 moderate 11 H 0.15 95 2.1 1.0 19.4 13.0 89 mild- moderate Comparative Examples A none -- 1.22 1.2 1.1 21.5 81 116 mild- moderate I F 0.5 128 1.2 1.0 21.7 15.0 149 mild- moderate J B with 0.25 118 1.4 1.1 15.2 84 8 moderate- F 0.5 severe K A with 0.25 116 1.0 1.0 18.0 22 145 mild- F 0.5 moderate L I 0.15 84 2.0 1.0 22.5 29.5 87 moderate M J 0.15 116 2.0 1.0 17.8 42 108 moderate N K 0.15 95 2.0 1.0 21.5 27.8 115 moderate O L 0.15 113 1.8 1.1 21.0 14.8 167 mild- moderate P M 0.15 92 2.0 1.0 18.5 73.3 69 moderate Q N 0.15 94 2.2 1.0 19.5 61.9 89 moderate R O 0.15 103 1.8 1.0 20.5 37.8 88 moderate __________________________________________________________________________
______________________________________ Formulations of Higher Density Invention Additive Foams Chemical Components Comparative Examples of Foam Formulations Example S 12-13 ______________________________________ Polyol 100 100 Water (added) 2.65 2.65 TDI-80 39.68 39.68 Index 85 85 Tin 0.13 0.19 Amine 0.22 0.22 Silicone 1.3 1.3 Modifier 1 3.0 3.0 Additive D -- 0.0-0.15 Additive C -- 0.0-0.15 ______________________________________ Physical properties of High Density, Invention Additive Foams 90% Air Additive blow 25% comp. Flow, Addi- amt. time, IFD sets (AF) tive pphp sec lb. (%) cfm/sf ______________________________________ Comparative S none -- 145 21.5 9.3 51.3 12 D 0.15 102 20.0 5.8 34.2 13 C 0.15 111 19.1 9.0 43.1 ______________________________________ All foams ≦3.0% settling.
______________________________________ Formulations Using Modifiers With Different Ratios of Cell Openers to Crosslinking/Extending agent. Compar- ative Chemical Components Example Example Example Example of Foam Formulation T 14 15 16 ______________________________________ Polyol 100 100 100 100 Water (added) 5.1 5.1 5.25 5.25 TDI-80 65.9 65.9 65.1 65.1 Index 88 88 88 88 Tin 0.18 0.25 0.28 0.28 Silicone 1.3 1.3 1.3 1.3 Amine 0.35 0.25 0.25 0 Modifier 2 5.0 5.0 0 0 Modifier 3 0 0 5 5 Additive C 0 0.4 0.4 0.4 ______________________________________
__________________________________________________________________________ Physical Properties of Invention Additive Foams 50% Additive Blow time, Density, 25% IFD, Comp. Sets Airflow Finger- Additive amt., pphp sec. pcf lbs (%) (cfm/sf) nailing __________________________________________________________________________ Comparative T None 0 90 1.05 22.3 15 65 mild Example 14* Additive C 0.4 63 1.06 8.7 6 114 very mild Example 15 Additive C 0.4 56 1.04 8.99 9 80 very mild Example 16 Additive C 0.4 64 1.03 9.62 7 95 very mild __________________________________________________________________________ *very minor splits observed
Claims (18)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/086,816 USRE36233E (en) | 1993-08-03 | 1998-05-29 | Use of softening additives in polyurethane foam |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10118993A | 1993-08-03 | 1993-08-03 | |
US08/326,293 US5539011A (en) | 1993-08-03 | 1994-10-20 | Use of softening additives in polyurethane foam |
US09/086,816 USRE36233E (en) | 1993-08-03 | 1998-05-29 | Use of softening additives in polyurethane foam |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10118993A Continuation-In-Part | 1993-08-03 | 1993-08-03 | |
US08/326,293 Reissue US5539011A (en) | 1993-08-03 | 1994-10-20 | Use of softening additives in polyurethane foam |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE36233E true USRE36233E (en) | 1999-06-22 |
Family
ID=26797995
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/086,816 Expired - Fee Related USRE36233E (en) | 1993-08-03 | 1998-05-29 | Use of softening additives in polyurethane foam |
Country Status (1)
Country | Link |
---|---|
US (1) | USRE36233E (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6683119B1 (en) * | 1998-04-16 | 2004-01-27 | Epik Entwicklung Und Produktion Innovativer Kunstoffe Gmbh | Method for producing polyols and polyols |
US20070037926A1 (en) * | 2005-08-12 | 2007-02-15 | Olsen David J | Polyvinyl chloride compositions |
US20080058450A1 (en) * | 2006-08-30 | 2008-03-06 | Eastman Chemical Company | Terephthalates as plasticizers in vinyl acetate polymer compositions |
US8784989B2 (en) | 2006-08-30 | 2014-07-22 | Eastman Chemical Company | Sealant compositions having a novel plasticizer |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3804782A (en) * | 1972-06-19 | 1974-04-16 | Basf Wyandotte Corp | Flexible cellular polyurethane foam compositions having increased flame retardance |
US4101466A (en) * | 1976-12-01 | 1978-07-18 | Texaco Development Corp. | Bis (dimethylaminopropyl)-amine derivatives as polyurethane catalysts |
US4101470A (en) * | 1976-11-11 | 1978-07-18 | Texaco Development Corp. | Urethane catalysts |
EP0358282A2 (en) * | 1989-11-08 | 1990-03-14 | Shell Internationale Researchmaatschappij B.V. | Soft flexible polyurethane foams, a process for preparing the same, and a polyol composition useful in said process |
US4950694A (en) * | 1989-06-29 | 1990-08-21 | Union Carbide Chemicals And Plastics Company Inc. | Preparation of polyurethane foams without using inert blowing agents |
US5034426A (en) * | 1987-07-20 | 1991-07-23 | Air Products And Chemicals, Inc. | Aromatic diamine catalytic chain extenders |
US5084486A (en) * | 1990-12-20 | 1992-01-28 | Union Carbide Chemicals & Plastics Technology Corporation | Reactive feed stream to replace inert blowing agent feed stream in a polyurethane foam process |
US5364852A (en) * | 1992-06-06 | 1994-11-15 | Basf Aktiengesellschaft | Preparation of compact or cellular elastomers containing urethane and urea groups, and moldings produced therefrom |
-
1998
- 1998-05-29 US US09/086,816 patent/USRE36233E/en not_active Expired - Fee Related
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3804782A (en) * | 1972-06-19 | 1974-04-16 | Basf Wyandotte Corp | Flexible cellular polyurethane foam compositions having increased flame retardance |
US4101470A (en) * | 1976-11-11 | 1978-07-18 | Texaco Development Corp. | Urethane catalysts |
US4101466A (en) * | 1976-12-01 | 1978-07-18 | Texaco Development Corp. | Bis (dimethylaminopropyl)-amine derivatives as polyurethane catalysts |
US5034426A (en) * | 1987-07-20 | 1991-07-23 | Air Products And Chemicals, Inc. | Aromatic diamine catalytic chain extenders |
US4950694A (en) * | 1989-06-29 | 1990-08-21 | Union Carbide Chemicals And Plastics Company Inc. | Preparation of polyurethane foams without using inert blowing agents |
EP0358282A2 (en) * | 1989-11-08 | 1990-03-14 | Shell Internationale Researchmaatschappij B.V. | Soft flexible polyurethane foams, a process for preparing the same, and a polyol composition useful in said process |
EP0429103A1 (en) * | 1989-11-08 | 1991-05-29 | Shell Internationale Researchmaatschappij B.V. | Soft flexible polyurethane foams, a process for preparing the same, and a polyol composition useful in said process |
US5084486A (en) * | 1990-12-20 | 1992-01-28 | Union Carbide Chemicals & Plastics Technology Corporation | Reactive feed stream to replace inert blowing agent feed stream in a polyurethane foam process |
US5364852A (en) * | 1992-06-06 | 1994-11-15 | Basf Aktiengesellschaft | Preparation of compact or cellular elastomers containing urethane and urea groups, and moldings produced therefrom |
Non-Patent Citations (27)
Title |
---|
Chemical Abstract CA105(10):79879m, Oct. 1984. * |
Chemical Abstract CA109(20):171790t, Oct. 1986. * |
Chemical Abstract CA117(10):91012d, Sep. 1990. * |
Chemical Abstract CA118(12):104433, Sep. 1990. * |
Chemical Abstract CA76(20):114507v, Dec. 1971. * |
Chemical Abstract CA81(14):78662j; May 1974. * |
Chemical Abstract CA85(24):178515q, Sep. 1976. * |
Chemical Abstract CA86(22):156226q, Feb. 1977. * |
Chemical Abstract CA87(8): 54035e, May 1977. * |
Chemical Abstract CA89(2):7054s, Mar. 1978. * |
Chemical Abstract CA90(6):39598j, Sep. 1978. * |
Chemical Abstract CA92(18):147893b, Jan. 1980. * |
Chemical Abstract CA93(6):477732q, Mar. 1980. * |
Chemical Abstract CA96(18):143542w, Feb. 1982. * |
Chemical Abstract CA97(20):163689y, Aug. 1982. * |
Chemical Abstract CA99(4):23488y, Sep. 1981. * |
Klemper, D. et. al., "Handbook of Polymeric Foams and Foam Technology" pp. 96-101; Dec. 1991. |
Klemper, D. et. al., Handbook of Polymeric Foams and Foam Technology pp. 96 101; Dec. 1991. * |
Malwitz, N., et. al., "Amine Catalysis of Polyurethane Foams", Polyurethane/Technical Marketing COnference, Oct. 1986, pp. 338-353. |
Malwitz, N., et. al., Amine Catalysis of Polyurethane Foams , Polyurethane/Technical Marketing COnference, Oct. 1986, pp. 338 353. * |
Odian, G., Principles of Polymerization second edition, p. 128; Dec. 1981. * |
Shell Urethane Chemicals Technical Manual, UC 2.5.8, "Carapor 2001", UC3.1.12, Carapor 2001 in the Manufacture of Soft Flexible Slabstock Foams Sep. 1990. |
Shell Urethane Chemicals Technical Manual, UC 2.5.8, Carapor 2001 , UC3.1.12, Carapor 2001 in the Manufacture of Soft Flexible Slabstock Foams Sep. 1990. * |
Vandichel, N. E., et. al., "Reduction of CFC-11 Usage in Flexible Polyurethane Foams through Modifications to Polymer Morphology", pp. 486-491, 30th Annual Polyurethane Technical Marketing Conference (Oct. 1990). |
Vandichel, N. E., et. al., Reduction of CFC 11 Usage in Flexible Polyurethane Foams through Modifications to Polymer Morphology , pp. 486 491, 30th Annual Polyurethane Technical Marketing Conference (Oct. 1990). * |
Zellmer, V., et al., "New Aspects in the Production of Soft Flexible Polyurethane Foams Without Auxiliary Blowing Agents", Oct. 1989. |
Zellmer, V., et al., New Aspects in the Production of Soft Flexible Polyurethane Foams Without Auxiliary Blowing Agents , Oct. 1989. * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6683119B1 (en) * | 1998-04-16 | 2004-01-27 | Epik Entwicklung Und Produktion Innovativer Kunstoffe Gmbh | Method for producing polyols and polyols |
US20070037926A1 (en) * | 2005-08-12 | 2007-02-15 | Olsen David J | Polyvinyl chloride compositions |
US8372912B2 (en) | 2005-08-12 | 2013-02-12 | Eastman Chemical Company | Polyvinyl chloride compositions |
US9388293B2 (en) | 2005-08-12 | 2016-07-12 | Eastman Chemical Company | Polyvinyl chloride compositions |
US20080058450A1 (en) * | 2006-08-30 | 2008-03-06 | Eastman Chemical Company | Terephthalates as plasticizers in vinyl acetate polymer compositions |
US8088854B2 (en) | 2006-08-30 | 2012-01-03 | Eastman Chemical Company | Terephthalates as plasticizers in vinyl acetate polymer compositions |
US8784989B2 (en) | 2006-08-30 | 2014-07-22 | Eastman Chemical Company | Sealant compositions having a novel plasticizer |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5539011A (en) | Use of softening additives in polyurethane foam | |
CA2455503C (en) | Process to manufacture flexible polyurethane foams | |
EP0406702B1 (en) | Preparation of polyurethane foams without using inert blowing agents | |
US7238730B2 (en) | Viscoelastic polyurethane foam | |
CN103221446B (en) | Flame resistant flexible polyurethane foam | |
EP2621987B1 (en) | Process for making low density high resiliency flexible polyurethane foam | |
US9688830B2 (en) | PUR foam with enlarged cell structure | |
US20040266900A1 (en) | Viscoelastic polyurethane foam | |
WO2002010245A1 (en) | Manufacture of mdi-tdi based flexible polyurethane foams | |
US5084486A (en) | Reactive feed stream to replace inert blowing agent feed stream in a polyurethane foam process | |
MXPA06013028A (en) | Flexible polyurethane foam. | |
US4497913A (en) | Process for preparing a stable dispersion of a polymer in a polyol and its use in the production of high resilience polyurethane foam | |
KR101797448B1 (en) | Method for making low density polyurethane foam for sound and vibration absorption | |
JP7204650B2 (en) | Polyol blends useful for making viscoelastic foams | |
USRE36233E (en) | Use of softening additives in polyurethane foam | |
EP1326909A2 (en) | Polyurethanes containing dispersed crystalline polyesters | |
EP1809679B1 (en) | Process for making a pipa-polyol | |
MXPA01000337A (en) | Silicone surfactants for making polyurethane flexible molded foams. | |
CN108368230B (en) | Process for producing polyurethane foam | |
WO1995023819A1 (en) | Process for producing a soft, flexible, hot molded polyurethane foam | |
WO2001032732A1 (en) | Process for making rigid and flexible polyurethane foams |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: WITCO CORPORATION, CONNECTICUT Free format text: MERGER;ASSIGNOR:OSI SPECIALTIES HOLDING COMPANY;REEL/FRAME:009731/0496 Effective date: 19981231 Owner name: OSI SPECIALTIES HOLDING COMPANY, CONNECTICUT Free format text: MERGER;ASSIGNOR:OSI SPECIALTIES INC.;REEL/FRAME:009719/0787 Effective date: 19981231 |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
AS | Assignment |
Owner name: CK WITCO CORPORATION, CONNECTICUT Free format text: CHANGE OF NAME;ASSIGNOR:WITCO CORPORATION;REEL/FRAME:013804/0317 Effective date: 19990901 |
|
AS | Assignment |
Owner name: CK WITCO CORPORATION, CONNECTICUT Free format text: CORRECTIVE CHANGE OF NAME TO CHANGE THE NATURE OF CONVEYANCE TO MERGER PREVIOUSLY RECORDED AT REEL 013804 FRAME 0317. CONVEYING PARTY HEREBY CONFIRMS THE MERGER DOCUMENT.;ASSIGNOR:WITCO CORPORATION;REEL/FRAME:013828/0977 Effective date: 19990901 Owner name: CK WITCO CORPORATION, CONNECTICUT Free format text: CHANGE OF NAME;ASSIGNOR:WITCO CORPORATION;REEL/FRAME:013821/0299 Effective date: 19990901 |
|
AS | Assignment |
Owner name: CROMPTON CORPORATION, CONNECTICUT Free format text: CHANGE OF NAME;ASSIGNOR:CK WITCO CORPORATION;REEL/FRAME:013828/0654 Effective date: 20000427 |
|
AS | Assignment |
Owner name: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT, Free format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.;MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG;MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK;REEL/FRAME:019511/0166 Effective date: 20070228 |
|
AS | Assignment |
Owner name: GENERAL ELECTRIC COMPANY,NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CROMPTON CORPORATION;REEL/FRAME:020072/0289 Effective date: 20030731 Owner name: GENERAL ELECTRIC COMPANY, NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CROMPTON CORPORATION;REEL/FRAME:020072/0289 Effective date: 20030731 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
AS | Assignment |
Owner name: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., A Free format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS, INC.;JUNIPER BOND HOLDINGS I LLC;JUNIPER BOND HOLDINGS II LLC;AND OTHERS;REEL/FRAME:022902/0461 Effective date: 20090615 |
|
AS | Assignment |
Owner name: MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK, JAPAN Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 Owner name: MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG, GERMANY Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 Owner name: MOMENTIVE PERFORMANCE MATERIALS INC., NEW YORK Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 |
|
AS | Assignment |
Owner name: MOMENTIVE PERFORMANCE MATERIALS INC., NEW YORK Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT;REEL/FRAME:054883/0855 Effective date: 20201222 |