Curable resin composition

Details Curable resin composition Curable resin composition

1997-10-31

2001-02-06

Dawson, Robert (Department: 1712)

Compositions: coating or plastic

Coating or plastic compositions

Silicon containing other than solely as silicon dioxide or...

C106S287160, C524S858000, C524S860000, C524S863000

Reexamination Certificate

active

06183551

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
the present invention relates to a curable resin composition comprising a saturated hydrocarbon polymer having at least one silicon-containing group which has at least one hydroxyl or hydrolyzable group bonded to a silicon atom and is crosslinkable through the formation of a siloxane bond (hereinafter referred to as a “reactive silicon-containing group”).
2. Description of the Prior Art
It is known that saturated hydrocarbon polymers having at least one reactive silicon-containing group in a molecule have interesting properties that they are crosslinked through the formation of siloxane bonds which is associated with the hydrolysis of reactive silicon-containing groups with moisture even at room temperature, and provide rubbery cured materials. Such polymers are useful as sealing materials for construction or sealing materials for insulating glass units, since they have excellent heat resistance, water resistance, weather resistance and the like.
The sealing materials for construction are required to have good handling properties and workability, since they are applied at construction sites using caulking guns and the like. The sealing materials for insulating glass units are discharged using applicators, that is, apparatuses for discharging sealing materials, in factories for insulating glass units. In this case, good workability with good discharging properties is required for the sealing materials.
However, saturated hydrocarbon polymers such as polyisobutylene have high viscosity and thus low handling properties, when they are used as sealants such as the sealing materials for construction or insulating glass units. Thus, they are plasticized by the addition of hydrogenated polybutene, paraffinic oils, naphthenic oils, and the like. However, the use of such plasticizers may be associated with some problems, for example, large heating loss, insufficient plasticizing effects, low flowability at low temperature, etc. Because of the low flowability at low temperature, the sealing materials for construction, which have to be applied at the construction sites, are attended with low extrudability or workability in winter seasons.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a curable resin composition comprising a saturated hydrocarbon polymer having a reactive silicon-containing group which has improved workability, in particular, at low temperature without deteriorating physical, adhesion and curing properties and storage stability of the composition.
According to the first aspect, the present invention provides a curable resin composition comprising:
(A) a saturated hydrocarbon polymer having at least one reactive silicon-containing group in a molecule, and
(B) a hydrogenated oligomer of an &agr;-olefin.
According to the second aspect, the present invention provides a curable resin composition comprising:
(A) a saturated hydrocarbon polymer having at least one reactive silicon-containing group in a molecule,
(C) a saturated hydrocarbon oligomer, and
(D) an ester plasticizer.
DETAILED DESCRIPTION OF THE INVENTION
A saturated hydrocarbon polymer contained in the curable resin composition of the present invention has, in a molecule, at least one silicon-containing group which has at least one hydroxyl or hydrolyzable group bonded to a silicon atom and is crosslinkable through the formation of a siloxane bond, that is, at least one reactive silicon-containing group.
The saturated hydrocarbon polymer means a polymer which contains substantially no carbon—carbon unsaturated bond except aromatic rings. Examples of the saturated hydrocarbon polymer are polyethylene, polypropylene, polyisobutylene, hydrogenated polybutadiene, hydrogenated polyisoprene, and the like.
A preferable example of the reactive silicon-containing group is a group of the formula (1):
wherein R
1
and R
2
are the same or different and represent a hydrogen atom, a C
1-20
alkyl group, a C
6-20
aryl group, a C
7-20
aralkyl group or a triorganosiloxy group of the formula: (R′)
3
SiO— in which three R′ groups are the same or different and represent a hydrogen atom or a C
1-20
alkyl group which may be substituted with, for example, a halogen atom, C
6-20
aryl group, and the like; the X groups are the same or different and represent a hydroxyl group or a hydrolyzable group; a is 0, 1, 2 or 3; and b is 0, 1 or 2, provided that the sum of a and b is not 0; and m is an integer of 0 to 19.
The hydrolyzable group may be any conventional hydrolyzable group, and examples of such a group are a hydrogen atom, an alkoxy group, an acyloxy group, a ketoxymate group, an amino group, an amido group, an aminoxy group, a mercapto group, an alkenyloxy group, and the like.
Among them, the alkoxy, amido and aminoxy groups are preferable. In particular, the alkoxy group is preferable in view of its mild hydrolyzability and easy handling.
One, two or three hydrolyzable groups and/or hydroxyl groups can be attached to one silicon atom, and the total number of the hydrolyzable groups and/or hydroxyl groups, that is, (a+mb) is preferably between 1 and 5. When two or more hydrolyzable or hydroxyl groups are present in the reactive silicon-containing group, they may be the same or different.
The reactive silicon-containing group contains at least one silicon atom. When the silicon atoms are bonded through siloxane bonds or the like, the number of silicon atoms is preferably 20 or less. In particular, a reactive silicon-containing group of the formula (2):
wherein R
2
and X are the same as defined above and a′ is 1, 2 or 3, is preferable, because of easy availability.
The saturated hydrocarbon polymer contains at least one reactive silicon-containing group, preferably 1.1 to 5 reactive silicon-containing groups in a molecule on the average. When the number of the reactive silicon-containing group in a molecule is less than one, the composition tends to have insufficient curing properties, and thus the cured material may not have good rubbery elasticity.
The reactive silicon-containing group(s) may be bonded to an end or an internal part of each polymer chain of the saturated hydrocarbon polymer, or both. The reactive silicon-containing groups are preferably bonded to the ends of polymer chains, since they can maximize the chain length between cross-linking sites in the final cured material. Thus, a rubbery cured material having high strength and large elongation is easily obtained.
The saturated hydrocarbon polymers may be used independently or in admixture of two or more of them.
The polymer which constitutes the backbone of the saturated hydrocarbon polymer having the reactive silicon-containing group may be prepared by any conventional polymerization method. For example, such a polymer can be prepared by (1) polymerizing a C
1-6
olefin such as ethylene, propylene, 1-butene, isobutylene, etc. as a main monomer, or (2) polymerizing a diene compound such as butadiene, isoprene, etc. or copolymerizing such a diene compound with the above olefin, and then hydrogenating the polymer.
Among the polymers, isobutylene polymers and hydrogenated polybutadiene polymers are preferred, since functional groups are easily introduced at the polymer chain ends, their molecular weights can be easily controlled and the number of the functional groups to be introduced is increased.
Isobutylene polymers may consist of isobutylene repeating units. Alternatively, the isobutylene polymers may contain 50 wt. % or less, preferably 30 wt % or less, more preferably 10 wt. % or less of comonomeric repeating units.
Examples of the comonomer which may be copolymerized with isobutylene are C
4-12
olefins, vinyl ethers, aromatic vinyl compounds, vinylsilanes, allylsilanes, and the like. Specific examples of the comonomers are 1-butene, 2-butene, 2-methyl-1-butene, 3-methyl-1-butene, pentene, 4-methyl-1-pentene, hexane, vinylcyclohexene, methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, styrene, &agr;-methylstyrene, dimethylstyrene, monochlorostyrene,

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