Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Cellular products or processes of preparing a cellular...
Reexamination Certificate
2000-12-07
2002-04-23
Cooney, Jr., John M. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Cellular products or processes of preparing a cellular...
C521S130000, C521S174000, C560S026000, C560S330000, C560S336000, C560S359000
Reexamination Certificate
active
06376567
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to novel polyisocyanate compositions, to a process for the production of these polyisocyanate compositions, to a process for the production of cold cure flexible molded foam wherein the isocyanate component comprises the polyisocyanate composition of the present invention, and to the cold cure flexible molded foams produced by this process.
Mixtures of diisocyanates based on diphenylmethane diisocyanate (MDI) and polymethylene poly(phenyl isocyanate) (i.e. polymeric MDI or PMDI), and prepolymers based on such mixtures are known and described in the art. The use of these mixtures of diisocyanates based on MDI and polymeric MDI or PMDI, and prepolymers based on such mixtures in the art of manufacturing flexible polyurethane foam is also known and described in, for example, U.S. Pat. Nos. 4,239,856, 4,256,849, 4,261,852 and 4,365,025.
Numerous patents have issued which describe mixtures of diphenylmethane diisocyanates (MDI), polymethylene poly(phenyl isocyanate), and prepolymers based on these mixtures. See, for example, U.S. Pat. Nos. 3,152,162, 3,644,457, 3,701,796, 4,055,548, 4,118,411, 4,154,752, 4,177,205, 4,261,852, 4,442,235, 4,478,960, 4,490,302, 4,910,333, 5,070,114, 5,240,635, 5,246,977, 5,266,604, 5,350,778, 5,399,594, 5,563,232, 5,585,452, 5,877,227, 6,077,456 and 6,090,864.
It is known that MDI can be readily liquefied through carbodiimidization. Typical of this process are the processes described in U.S. Pat. Nos. 3,152,162, 3,384,643, 3,449,256, 3,640,966, 3,641,093, 3,701,796, 4,014,935, 4,088,665, 4,154,752, and 4,177.205.
It is also known, although less common, that MDI can be reacted with N,N-di-(2-hydroxy-propyl)aniline (as described in U.S. Pat. No. 3,394,165) and heating with N,N′-disubstituted thioureas (as described in U.S. Pat. No. 3,674,828).
A well known and common reaction of MDI is with various hydroxyl functional materials. Thus, the prior art has described several types of liquid isocyanates:
1) reaction products of MDI with poly-1,2-propylene ether glycols having molecular weights of from 134 to 700 (U.S. Pat. No. 3,644,457);
2) reaction products of MDI with a mixture of alkylene glycols containing at least three carbon atoms (U.S. Pat. Nos. 3,883,571 and 4,229,347);
3) mixtures of i) 30 to 80% by weight MDI, ii) 5 to 25% by weight MDI uretonimine-containing derivatives, iii) 20 to 50% by weight reaction products of MDI with diols or mixtures of diols having molecular weights of less than 175, and iv) 0 to 10% by weight polymethylene poly(phenyl isocyanates) (U.S. Pat. No. 4,031,026);
4) reaction products of polyoxyethylene glycols of molecular weight of from 200 to 600 and polymethylene poly(phenyl isocyanates) containing from 65 to 85% by weight of MDI, with the balance being higher homologues (U.S. Pat. No. 4,055,548);
5) reaction products of MDI with polyols having molecular weights of from 240 to 1500 and functionalities of from 2.7 to 3.3 (U.S. Pat. No. 4,102,833);
6) reaction products of MDI (of various 2,4′-isomer contents) with propylene glycol or poly-1,2-propylene ether glycols (U.S. Pat. No. 4,118,411) or with polyoxyethylene glycols (U.S. Pat. No. 4,115,429);
7) mixtures of i) 50 to 90% by weight reaction products of MDI and blends of 50 to 100% by weight of polyoxypropylene diols or triols having equivalent weights of from 750 to 3000 and 0 to 50% by weight polyoxyethylene diols or triols having equivalent weights of from 750 to 3000, and ii) 10 to 50% by weight of polymethylene poly(phenyl isocyanate) containing 30 to 65% of diphenylmethane diisocyanate (U.S. Pat. No. 4,261,852);
8) mixtures of i) reaction products of MDI and a polyol blend of a polyol having a molecular weight of at least 1000 and a polyol having a molecular weight of from 115 to 300 and ii) liquefied MDI (U.S. Pat. No. 4,321,333);
9) reaction products of MDI and an N-substituted ethanolamine (U.S. Pat. No. 4,332,742);
10) reaction products of MDI containing from 10 to 20% by weight of the 2,4-isomer and a 5500 molecular weight polyether triol (U.S. Pat. No. 4,448,904);
11) reaction products of MDI with a phenyl-substituted alkane diol (U.S. Pat. No. 4,490,300) or with a monoallyl ether of trimethylol-propane (U.S. Pat. No. 4,490,301);
12) reaction products of MDI with a mixture of a monohydroxyl compound, a poly-1,2-propylene glycol and a low molecular weight triol (U.S. Pat. No. 4,490,302);
13) reaction products of MDI of various isomer contents with 1,3-butane diol and propylene glycol (U.S. Pat. No. 4,539,156), with neopentyl glycol and propylene glycol (U.S. Pat. No. 4,539,157) and 1,3-butane diol and neopentyl glycol (U.S. Pat. No. 4,539,158);
14) reaction products of MDI with amines and tripropylene glycol (U.S. Pat. No. 4,883,909);
15) reaction products of MDI high molecular weight polyols and tripropylene glycol (U.S. Pat. Nos. 4,442,235 and 4,910,333 );
16) mixtures of i) reaction products of MDI and a polyol of equivalent weight of from 30 to 600 and ii) polymethylene poly(phenyl isocyanates) (U.S. Pat. No. 5,240,635); and
17) mixtures of i) reaction products of MDI and polyoxy-tetramethylene glycols of equivalent weight of from 250 to 1500, and ii) up to 30% by weight of a second isocyanate which can be the 2,4′-isomer or a polymethylene poly(phenyl isocyanate) (U.S. Pat. No. 5,246,977).
Other liquid isocyanate compositions are described in U.S. Pat. Nos. 4,365,025,4,525,490, 4,644,018, 5,070,114, 5,266,604 and 5,430,072.
The liquid isocyanates of U.S. Pat. No. 4,365,025 are prepolymers prepared from (a) a mixture of MDI and PMDI having a functionality of greater than 2.0, and (b) one or more polyols having 2 to 3 hydroxyl groups and at least about 50% by weight of oxyethylene groups, wherein the ratio of NCO equivalents to hydroxyl equivalents is from 1.5:1 to 5:1.
U.S. Pat. No. 5,070,114 describes a liquid isocyanate-containing prepolymer having an NCO functionality greater than 2 and an NCO content of from 2 to 12%. These are prepared by reacting (i) an isocyanate-reactive polymer having a nominal functionality of 2 to 4 and an average equivalent weight of about 500 to about 5,000, with (ii) a stoichiometric excess of a MDI composition having an average functionality of from 2 to 2.3 and containing at least 2% by weight of the 2,4′-isomer of MDI.
U.S. Pat. No. 5,266,604 discloses a liquid polyisocyanate prepolymer having a free NCO-group content of from 2 to 15% by weight. These prepolymers comprise the reaction products of an isocyanate-reactive polymer having a nominal functionality of 2 to 6 and an equivalent weight of 500 to 5,000 with a stiochiometric excess of a polyisocyanate. Flexible polyurethane foams can be prepared from these prepolymers by reaction with an isocyanate-reactive composition comprising at least 50% by weight water.
Liquid isocyanate-terminated prepolymers are also disclosed by U.S. Pat. No. 5,399,594. These are characterized by a functionality of 2 or more and have an NCO content of 2 to 15%. The prepolymers are reaction products of an isocyanate-reactive polymer having a functionality of 2 to 6 and an equivalent weight of 750 to 5,000, with a stoichiometric excess of an MDI having an average functionality of 2 to 2.3. Flexible foams can also be prepared from these prepolymers.
A homogenous mixture of two polyisocyanates is disclosed by U.S. Pat. No. 5,430,072. One of the polyisocyanate components is a prepolymer having an NCO group content of from 2 to 15% by weight, and is the reaction product of an isocyanate-reactive compound having a nominal functionality of 2 to 8 and an equivalent weight of 500 to 5,000 with a stoichiometric excess of a MDI composition. The other isocyanate in the homogeneous mixture has an NCO group content of at least 25% by weight. This homogeneous mixture of isocyanates can be used to form flexible polyurethane foams by reaction with an isocyanate-reactive component which is at least 40% by weight water.
The polyisocyanate compositions of U.S. Pat. No. 5,877,227 comprise a semi-prepolymer which is the reaction product of a
Werner Joachim
Zibert Ronald
Bayer Corporation
Brown N. Denise
Cooney Jr. John M.
Gil Joseph C.
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