Compositions containing cyanate ester and aromatic compounds...

Details Compositions containing cyanate ester and aromatic compounds... Compositions containing cyanate ester and aromatic compounds...

2000-06-26

2002-04-02

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C560S301000, C560S130000, C560S138000, C560S140000, C528S422000, C525S437000, C525S523000, C525S419000, C525S903000

Reexamination Certificate

active

06365671

ABSTRACT:

BACKGROUND OF THE INVENTION
Phenolic cyanate esters have been described extensively in the art. U.S. Pat. No. 5,360,887, for example, describes a flame resistant thermosetting composition containing a monocyanate ester and a dicyanate ester of the formula
wherein the bridging member A can be a direct bond, methylene or mono- or disubstituted methylene with alkyl and/or an aryl group, or a five or six membered cycolalkylene, sulfonyl, thio, oxyl, carbonyl or xylylene. The teachings in U.S. Pat. No. 5,109,078 represent one of many teachings of cyanato-group containing phenolic resins of the formula:
wherein X is a divalent organic radical, preferably a radical selected from the group consisting of: —CH2—, —CO—, —SO2—, (S)y,
There is a need in the transportation industry, particularly for aircraft interiors, for molded polymeric components that exhibit very low peak heat release rates. Many cyanate esters exhibit good dielectric properties, water absorption and flame retardancy. However, all of the currently known cyanate esters fail to have heat release rates below 35 Joule/g-°K, more preferably below 10 Joule/g-°K. Low peak heat release rates can be attained using other high performance polymers such as polyphenylsulfone, polyamineimides, polybenzoimadazoles and polybenzoxazoles.
All of the currently available polymers having relatively low peak heat release rates suffer from one or more disadvantages such as high cost of manufacture or challenging processing requirements. The present invention produces molded articles having the desired low peak heat release rate using cyanate ester compounds and compositions thereof.
SUMMARY OF THE INVENTION
The present invention relates, in a first aspect, to a composition of matter containing
1) a selected cyanate ester compound represented by formula (I):
 wherein
Z is C
1
-C
4
alkylene group or a five or six membered cycolalkylene;
R
1
, R
5
, R
6
and R
10
, independently of one another, are unsubstituted or halogen- or C
1
-C
3
alkyl-substituted C
1
-C
4
alkyl that can be saturated or unsaturated, halogen, H, OCN, OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl;
R
2
, R
4
, R
7
and R
9
, independently of one another, are C
1
-C
4
alkyl, halogen, H, OCN, or OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl;
R
3
and R
8
, independently of one another, are C
1
-C
4
alkyl, halogen H, OCN or OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl; or
R
1
and R
2
together and/or R
2
and R
3
together, and/or R
9
and R
10
together, and/or R
8
and R
9
together, independently of one another, form one or more aromatic rings or five or six membered cycloalkylene that can each be substituted with C
1
-C
4
alkyl or halogen;
R
11
and R
12
, independently of one another are H, phenyl, C
1
-C
4
alkyl or halogen; wherein at least one of aromatic rings A and B or at least one of the aromatic rings or the five or six membered ring formed by R
1
and R
2
and/or R
2
and R
3
and/or R
9
and R
10
and/or R
8
and R
9
is substituted by at least one cyanato group;
2) up to about 15% by weight of selected aromatic hydroxy compounds having at least two rings having at least 6 carbon atoms per ring;
3) up to about 15% by weight of a halogenated compound according to formula II
 wherein
Z is C
1
-C
4
alkylene group;
R
1
, R
5
, R
6
and R
10
, independently of one another, are unsubstituted or halogen- or C
1
-C
3
alkyl-substituted C
1
-C
4
alkyl that can be saturated or unsaturated, halogen, H, OCN, OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl;
R
2
, R
4
, R
7
and R
9
, independently of one another, are C
1
-C
4
alkyl, halogen, H, OCN, or OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl;
R
3
and R
8
, independently of one another, are C
1
-C
4
alkyl, halogen H, OCN or OH, C
1
-C
4
alkoxy, alkythio, mercaptan, nitro, —OCOR(C
1
-C
3
alkyl), —NCOR(C
1
-C
3
alkyl), —COR, —NO
2
, —NR′R″, wherein R, R′ and R″ are H or C
1
-C
3
alkyl; or
R
1
and R
2
together and/or R
2
and R
3
together, and/or R
9
and R
10
together, and/or R
8
and R
9
together, independently of one another, form one or more aromatic rings or five or six membered cycloalkylene that can each be substituted with C
1
-C
4
alkyl or halogen;
R
11
, and R
12
, independently of one another are H, phenyl, C
1
-C
4
alkyl or halogen; wherein at least one of aromatic rings A and B or at least one of the aromatic rings or the five or six membered ring formed by R
1
and R
2
and/or R
2
and R
3
and/or R
9
and R
10
and/or R
8
and R
9
is substituted by at least one hydroxyl group and at least one of R
11
and R
12
are a halogen group.
A preferred compound according to formula (I) is represented said formula where Z is C
1
-C
2
alkylene; R
1
and R
10
are H; R
2
, R
4
, R
7
and R
9
, independently of one another, are halogen, H, OCN, or OH; R
3
, R
5
, R
6
and R
8
, independently of one another, are H, OCN or OH; R
11
and R
12
are halogen; and at least one of aromatic rings A and B is substituted by at least one cyanato group.
A particularly preferred compound according to formula (I) is represented by said formula where Z is C
1
-C
2
alkylene; R
1
, R
5
, R
6
and R
10
are H; R
2
, R
4
, R
7
and R
9
, independently of are halogen or H; R
11
and R
12
are halogen; and R
3
and R
8
are OCN. More preferably, R
11
, and R
12
are chlorine or bromine. Most preferably, R
11
, and R
12
are chlorine.
A further preferred compound is characterized according to formula (1) above wherein Z is methylene; R
1
, R
2
, R
4
, R
5
, R
6
, R
7
, R
9
and R
10
are H; R
3
and R
8
are OCN; and R
11
and R
12
are chlorine.
A preferred compound is characterized according to formula (11) above wherein Z is C
1
-C
2
alkylene; R
1
and R
10
are H; R
2
, R
4
, R
7
and R
9
, independently of one another, are halogen, H, OCN, or OH; R
3
, R
5
, R
6
and R
8
, independently of one another, are H, OCN or OH; R
11
and R
12
are halogen; and at least one of aromatic rings A and B is substituted by at least one hydroxyl group.
A particularly preferred compound is characterized according to formula (II) above wherein Z is C
1
-C
2
alkylene; R
1
, R
5
, R
6
and R
10
are H; R
2
, R
4
, R
7
and R
9
, independently of one another, are halogen or H; R
11
, and R
12
are halogen; and R
3
and R
8
are OH. More preferably, R
11
, and R
12
are chlorine or bromine. Most preferably, R
11
, and R
12
are chlorine.
A further preferred compound is characterized according to formula (II) above wherein Z is methylene; R
1
, R
2
, R
4
, R
5
, R
6
, R
7
, R
9
and R
10
are H; R
3
and R
8
are OH; and R
11
and R
12
are chlorine.
The present invention relates, in a second aspect, to a prepolymer mixture containing a cyclotrimerized reaction product of either the selected aromatic hydroxyl compound or compound according to formula 11 and at least one of compound according to formula (I) above. Preferably, up to about 60% of the cyanato groups in the overall mixture are trimerized as a part of the cyclotrimerized reaction product. More particularly, about 10 to 40%, preferably, about 20 to 30% of the cyanato groups in the overall composition are trimerized as a part of the cyclotrimerized reaction product.
The present invention, in a further aspect, relates to a composition containing
a) a compound according to formula (I) above and
b) a co-curing component selected from
b1) a selected aromatic hydroxyl compou

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