Curable composition and compatibilizing agent

a composition and compatibilizing agent technology, applied in the field of curable composition and compatibilizing agent, can solve the problems of difficult control of acrylic polymerization, difficult to introduce a functional group into such polymers at one or both ends, and difficult to achieve radical polymerization of functional group-terminated vinyl polymers, etc., to achieve good storage stability, high gel fraction, and high elongation characteristic

Inactive Publication Date: 2009-01-08
KANEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a curable composition that includes a crosslinkable functional group-containing vinyl polymer and a crosslinkable functional group-containing polyether polymer. The composition has good storage stability and can produce cured products that show high elongation characteristics and good weatherability. The invention also provides methods for preparing the composition and a compatibilizing agent that can help to compatibilize the polyether polymer and vinyl polymer with each other. The technical effects of the invention include improved properties of the cured products and better compatibility between the polymers.

Problems solved by technology

Unlike polymers obtainable by ionic polymerization or polycondensation, functional group-containing vinyl polymers, in particular functional group-terminated vinyl polymers, obtain able by radical polymerization have scarcely been put to practical use.
On the other hand, it is not easy to control the polymerization of acrylic polymers because of side reactions, and it is very difficult to introduce a functional group into such polymers at one or both ends.
However, it is not easy to produce them on a commercial scale.
These methods can hardly ensure that a desired functional group will be introduced at each of both ends.
Hence, cured products having satisfactory characteristics cannot be obtained.
For introducing a functional group at each of both ends without fail, a chain transfer agent must be used in large amounts, and this is a problem from the production process viewpoint.
In addition, these methods use an ordinary method of radical polymerization, so that it is difficult to control the molecular weight and molecular weight distribution (ratio of weight average molecular weight to number average molecular weight) of the product polymer.
However, these polyethers, in particular polyethers having a main chain comprising a polypropylene oxide, have a problem in that hydrogen atoms each bound to a tertiary carbon atom are readily oxidized, hence the weatherability becomes poor, if no antioxidant is used.
Therefore, it is difficult to attain a high percentage of crosslinkable functional group introduction at both ends.
As a result, there arises a problem, namely the gel fraction of cured products decreases.
In this case, a problem arises, namely the high elongation characteristics intrinsic in polyether polymers are impaired.
In this case, the elongation at break, in particular, decreases and, accordingly, the range of application of the composition in question is drastically restricted.
In addition, the (meth)acrylic polymer used there is a product synthesized by free radical polymerization and, therefore, has a broad molecular weight distribution and a high viscosity, causing a problem that the mixture thereof with a polyether polymer also shows a high viscosity.
In this case, however, the compatibility of the two polymers may be poor in certain instances according to the molecular weight and molecular weight distribution of the vinyl polymer and / or polyether polymer and to the blending ratio of these two polymers.
In that case, the curable composition resulting from blending, when stored for a long period of time, may undergo phase separation, for instance, hence the storage stability thereof may deteriorate.
Furthermore, cured products obtainable from a composition with insufficient compatibility are inferior in homogeneity, so that good mechanical and physical properties may not be realized.

Method used

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  • Curable composition and compatibilizing agent
  • Curable composition and compatibilizing agent
  • Curable composition and compatibilizing agent

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of a Crosslinkable silyl Group-Terminated poly(n-butyl acrylate / stearyl acrylate) copolymer

[0309]A 2-liter flask was charged with 8.39 g (58.5 mmol) of cuprous bromide and 112 mL of acetonitrile, and the contents were heated at 70° C. with stirring under a nitrogen stream for 20 minutes. Thereto were added 17.6 g (48.8 mmol) of diethyl 2,5-dibromoadipate, 996 mL (6.94 mol) of butyl acrylate and 279 g (0.858 mol) stearyl acrylate, and the mixture was further heated at 70° C. for 40 minutes with stirring. Thereto was added 0.41 mL (1.95 mmol) of pentamethyldiethylenetriamine (herein after referred to as “triamine”) to thereby initiate the reaction. Then, heating at 70° C. was continued with stirring, and 2.05 mL (9.75 mmol) of triamine was added. At 330 minutes after the start of the reaction, 288 mL (1.95 mol) of 1,7-octadiene and 4.1 mL (19.5 mmol) of triamine were added, and heating at 70° C. was continued with stirring. At 570 minutes after the start of the reaction, the...

synthesis example 2

Synthesis of a Crosslinkable silyl Group-Terminated poly(n-butyl acrylate)

[0312]A 2-liter flask was charged with 8.39 g (58.5 mmol) of cuprous bromide and 112 mL of acetonitrile, and the contents were heated at 70° C. with stirring under a nitrogen stream for 30 minutes. Thereto were added 17.6 g (48.8 mmol) of diethyl 2,5-dibromoadipate and 224 mL (1.56 mol) of butyl acrylate, and the mixture was further heated at 70° C. with stirring for 45 minutes. Thereto was added 0.41 mL (1.95 mmol) of pentamethyldiethylenetriamine (herein after referred to as “triamine”), and the reaction was thereby started. While continued heating at 70° C. with stirring, 895 mL (6.24 mol) of butyl acrylate was added dropwise intermittently over 160 minutes beginning at 80 minutes after start of the reaction. During this dropping, 1.84 mL (8.81 mmol) of triamine was added. After the lapse of 375 minutes after start of the reaction, 288 mL (1.95 mol) of 1,7-octadiene and 4.1 mL (19.5 mmol) of triamine were a...

examples 1 to 5

[0315]The crosslinkable silyl group-containing vinyl polymer of Synthesis Example 1 was blended with a commercially available, crosslinkable silyl group-terminated polyether polymer (S203, product of Kaneka Corporation) in various mixing ratios shown in Table 1, and the mixtures were evaluated for compatibility by visual observation. Each mixture (100 parts by weight) was blended under stirring with 1 part by weight of water and 1 part by weight of dibutyltin dimethoxide, the whole mixture was defoamed at room temperature using a vacuum drier, and then curing was allowed to proceed at 50° C. for 3 days to give a rubber-like cured product. The results thus obtained are shown in Table 1.

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Abstract

It is an object of the present invention to provide a curable which has good storage stability and can give cured products retaining the high elongation characteristic originating from the polyether polymer and showing a high gel fraction and good weatherability.Thus, the present invention provides a durable compositionwhich comprises the following two components:a polyether polymer having at least one crosslinkable functional group anda vinyl polymerwhich is compatible with said polyether polymer having at least one crosslinkable functional group at a polymer terminus.Further, the present invention provides a curable compositionwhich comprises the following three components:a polyether polymer having at least one crosslinkable functional group,a vinyl polymer incompatible with said polyether polymer and having at least one crosslinkable function group, anda compatibilizing agent capable of compatibilizing said polyether polymer and said vinyl polymer with each other when added to a mixture thereof.

Description

TECHNICAL FIELD[0001]The present invention relates to a curable composition comprising a crosslinkable functional group-containing vinyl polymer and a crosslinkable functional group-containing polyether polymer and to a compatibilizing agent for compatibilizing the above polymers with each other.BACKGROUND ART[0002]Unlike polymers obtainable by ionic polymerization or polycondensation, functional group-containing vinyl polymers, in particular functional group-terminated vinyl polymers, obtain able by radical polymerization have scarcely been put to practical use. Among vinyl polymers, (meth)acrylic polymers have such characteristics as high weatherability and transparency that polyether polymers, hydrocarbon polymers or polyester polymers cannot have, and (meth)acrylic polymers having an alkenyl or crosslinking silyl group(s) on a side chain(s) are currently used in highly weather-resistant coating compositions and the like. On the other hand, it is not easy to control the polymeriz...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): C08G65/02C08F290/06C08F293/00C08G65/336C08L71/02
CPCC08F290/06C08F293/005C08G65/336C08L71/02C08L101/10C08L2666/02C08L2666/04C08L2666/14
InventorFUJITA, NAOSHIMIZU, YASUOHASEGAWA, NOBUHIRONAKAGAWA, YOSHIKI
OwnerKANEKA CORP