Compositions – Compositions containing a single chemical reactant or plural... – Organic reactant
Reexamination Certificate
2002-07-31
2004-06-01
Gorr, Rachel (Department: 1711)
Compositions
Compositions containing a single chemical reactant or plural...
Organic reactant
C528S049000, C528S056000, C560S025000, C560S026000, C560S115000, C560S158000, C560S166000, C560S330000, C560S336000, C560S355000, C524S591000, C524S839000, C524S840000
Reexamination Certificate
active
06743374
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
The present invention relates to a self-emulsifiable polyisocyanate with high functionality, and to a process for producing the same.
(2) Related Prior Art
Various processes for producing a self-emulsifiable polyisocyanate having allophanate bonds have been conventionally known as disclosed in, for example, JP-A-2000-34439, JP-A-11-349805, JP-A-11-100426 and the like.
Most of processes for producing a modified polyisocyanate containing allophanate bonds as disclosed in the above publications aims to produce allophanate bonds. However, these processes have the problem that a self-addition reaction of isocyanate groups and/or a self-polymerization reaction thereof are progressed as a side reaction, whereby a by-product is produced, which gives rise to a final product with a change in color and with turbidity. As the by-product, for example, a dimer with uretdione groups which is thermally unstable, or a trimer with isocyanurate groups which remarkably increases the viscosity of a final product while decreases solubility to a nonpolar solvent and compatibility to a resin such as a high molecular polyester is enumerated. Furthermore, when it is an object of the above processes to produce a polyisocyanate with high functionality, the system of reaction may be probably gelled.
OBJECTS AND SUMMARY OF THE INVENTION
The present invention has been carried out in order to solve the above-mentioned problems. Thus it is an object of the invention to provide a self-emulsifiable polyisocyanate with high functionality and low viscosity which substantially does not contain a dimers or a trimer, and to provide a method of producing the same.
The present inventors have eagerly studied to find the fact that a specific metallic salt can be used as an allophanate-forming catalyst to solve the above problems, whereby the present invention has been accomplished.
That is, the present invention is what is described in the following (1) to (8):
(1) A self-emulsifiable polyisocyanate with high functionality, having the average number of functional groups in 4.3 or more and a viscosity of 8,000 mPa·s (at 25° C.) or less, which is obtained by subjecting a modified polyisocyanate containing allophanate bonds and a poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to a urethanization reaction, said modified polyisocyanate being obtained by reacting a polyol (a) having the average number of functional groups in an amount of 2 or more with an organic polyisocyanate (b) in the presence of an allophanate-forming catalyst (c) comprising a zirconium carboxylate;
(2) A self-emulsifiable polyisocyanate with high functionality according to the above item (1), wherein said polyol (a) having the average number of functional groups in an amount of 2 or more is a polyol including side chain alkyl groups having the average number of functional groups in an amount of 2 or more;
(3) A self-emulsifiable polyisocyanate with high functionality according to the above item (1), wherein said organic polyisocyanate (b) is hexamethylene diisocyanate;
(4) A self-emulsifiable polyisocyanate with high functionality according to the above item (1), wherein the content of said poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to be used is in the range of 1 to 30% by weight of the resultant self-emulsifiable polyisocyanate with high functionality;
(5) A process for producing a self-emulsifiable polyisocyanate with high functionality according to the above item (1), wherein said process comprises the following first to fourth steps:
the first step: of reacting a polyol (a) having the average number of functional groups in an amount of 2 or more with an organic polyisocyanate (b) under an allophanate-forming catalyst (c) comprising a zirconium carboxylate;
the second step: of terminating the allophanate-forming reaction by adding a catalytic poison (d) thereto;
the third step: of removing a free organic polyisocyanate (b); and
the fourth step: of subjecting a modified polyisocyanate containing allophanate bonds as provided in the third step and a poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to a urethanization reaction;
(6) A process for producing a self-emulsifiable polyisocyanate with high functionality according to the above item (5), wherein said polyol (a) having the average number of functional groups in an amount of 2 or more is a polyol including side chain alkyl groups having the average number of functional groups in an amount of 2 or more;
(7) A process for producing a self-emulsifiable polyisocyanate with high functionality according to the above item (5), wherein said organic polyisocyanate (b) is hexamethylene diisocyanate; and
(8) A process for producing a self-emulsifiable polyisocyanate with high functionality according to the above item (5), wherein the amount of said poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to be used is 1 to 30% by weight of the resultant self-emulsifiable polyisocyanate with high functionality.
DETAILED DESCRIPTION OF THE INVENTION
First of all, materials used in the present invention will be explained.
As the polyol (a) having the average number of functional groups in an amount of 2 or more as used in the present invention, a low molecular weight polyol such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-buthanediol, 1,3-buthanediol, 1,4-buthanediol, 1,5-pentanediol, 1,6-hexanediol, 2-methyl-1,5-pentanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 1,8-octanediol, 1,9-nonanediol, 2,2-diethyl-1,3-propanediol, 2-n-butyl-2-ethyl-1,3-propanediol, 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol, 2-n-hexadecane-1,2-ethylene glycol, 2-n-eicosane-1,2-ethylene glycol, 2-n-octacosane-1,2-ethylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, hydrogenated bisphenol A, bis (&bgr;-hydroxyethyl)benzene, an addition product of bisphenol A to ethylene oxide or propylene oxide, trimethylolpropane, glycerin or pentaerythriol; or a polyether polyol as obtained by adding a low molecular weight cyclic ether such as ethylene oxide or propylene oxide to an initiator selected from the group consisting of the above-mentioned low molecular weight polyol, the after-mentioned low molecular weight polyamine, and a low molecular weight amino alcohol; or a polyester polyol which is obtained by adding a low molecular weight cyclic ester such as &egr;-caprolactone or &ggr;-valerolactone to an initiator selected from the group consisting of the above-mentioned low molecular weight polyol, the low molecular weight polyamine, and the low molecular weight amino alcohol; or a polyester polyol as obtained by the condensation polymerization of the above low molecular weight polyol and a polycarboxylic acid such as succinic acid, adipic acid or phthalic acid can be enumerated.
These polyols may be individually used, or two or more thereof may be mixed with each other for use.
Incidentally, as the low molecular weight polyamine, ethylenediamine, isophoronediamine, diethylenetriamine, and the like can be enumerated. As the low molecular weight amino alcohol, monoethanolamine, dimonoethanolamine, and the like can be enumerated.
In the present invention, when a polyol with side chain alkyl groups is used as a polyol (a), the resultant self-emulsifiable polyisocyanate is decreased in viscosity, and thus it is preferred. As the polyol (a), a polyether polyol or an aliphatic polyol with side chain alkyl groups having a carbon atom number of 10 or less is more preferred, and 1,2-propanediol, 1,3-butanediol, 2-methyl-1,5-penthanediol, 3-methyl-1,5-penthanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 2-n-butyl-2-ethyl-1,3-propanediol, or poly(oxypropylene)polyol is specifically preferred.
Th
Ikemoto Mitsushige
Kita Motomu
Sasahara Toshiaki
Gorr Rachel
Nippon Polyurethane Industry Co., Ltd.
Sughrue & Mion, PLLC
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