Crystalline polypropylene resin composition and amide compounds

Details Crystalline polypropylene resin composition and amide compounds Crystalline polypropylene resin composition and amide compounds

1993-01-13

2001-05-22

Sanders, Kriellion (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S214000, C564S152000, C564S155000, C564S180000

Reexamination Certificate

active

06235823

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a crystalline polypropylene resin composition containing an amide compound capable of acting as a nucleating agent for predominant formation of the &bgr;-crystal form and to a novel amide compound which is of use as a nucleating agent for the formation of the &bgr;-crystal form.
PRIOR ART
It is known that crystalline polypropylene may occur in &agr;, &bgr;, &ggr; and &dgr; crystal forms as well as in the smectic crystal form which is formed on quenching of melted polypropylene. The &bgr;-crystal form (hereinafter referred to as “&bgr;-form”) differs from the a-form which is found in the conventional natural pellet in that it is lower in melting point and in density, not to speak of differences in the mode of crystallization and of fracture, thus being of interest from application points of view (Kobunshi Kagaku 30, 694-698, (1973)).
For the production of crystalline polypropylene containing the &bgr;-form, a process comprising crystallizing molten polypropylene on a temperature gradient and a process comprising blending with a small amount of a nucleating agent (hereinafter referred to as “&bgr;-nucleating agent”) are known. Since the former process is time-consuming and provides only a low yield, the latter process employing a &bgr;-nucleating agent is more advantageous for all practical purposes.
As such a &bgr;-nucleating agent, &ggr;-quinacridone is well-known (Polymer Letters, 6, 539-546, (1968)). However, this nucleating agent has the drawback that it imparts a red tint to the product and requires special apparatus and operation for blending it with the polymer.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a novel &bgr;-nucleating agent insuring an efficient production of a product containing &bgr;-crystalline polypropylene in a large amount and much improved in the aspect of product color because of substantial absence of coloring property, and to provide a practically useful crystalline polypropylene resin composition containing said &bgr;-nucleating agent.
The inventors of the present invention discovered, after extensive research to provide a &bgr;-nucleating agent that would solve the above-mentioned problems, that a class of amide compounds having a specific chemical structure can accomplish the above object and that some of said amide compounds are novel compounds which are not described before in the published literature. The present invention has been achieved on the basis of the above findings.
The crystalline polypropylene resin composition of the present invention is characterized in that, in addition to a crystalline polypropylene resin, it contains at least one &bgr;-nucleating agent selected from the group consisting of amide compounds of the formula (1), amide compounds of the formula (2) and amide compounds of the formula (3) to be described below in an amount effective for increasing the content of the &bgr;-crystal form:
(1) an amide compound of the formula:
R
2
—NHCO—R
1
—CONH—R
3
  (1)
wherein R
1
is a residue of a C
3-20
saturated or unsaturated aliphatic dicarboxylic acid, a residue of a C
6-30
saturated or unsaturated alicycic dicarboxylic acid or a residue of a C
8-30
aromatic dicarboxylic acid; R
2
and R
3
are the same or different and each represents a C
3-12
cycloalkyl group, a C
3-12
cycloalkenyl group, or a group of the formula
wherein R
4
is a hydrogen atom, a C
1-12
straight- or branched-chain alkyl group, a C
2-12
straight- or branched-chain alkenyl group, a C
6-10
cycloalkyl group or a phenyl group; R
5
is a C
1-12
straight- or branched-chain alkyl group, a C
2-12
straight- or branched-chain alkenyl group, a C
6-10
cycloalkyl group or a phenyl group; and R
6
and R
7
each represents a C
1-4
straight- or branched-chain alkylene group; with the proviso that when R
4
is a hydrogen atom, a C
1-12
alkyl group or a C
6-10
cycloalkyl group, R
1
is a residue of a C
6
or C
8
saturated aliphatic dicarboxylic acid,
(2) an amide compound of the formula:
R
9
—CONH—R
8
—NHCO—R
10
  (2)
wherein R
8
is a residue of a C
4-28
alicyclic diamine, a residue of a C
4-14
heterocyclic diamine or a residue of a C
6-28
aromatic diamine; R
9
and R
10
are the same or different and each represents a C
3-12
cycloalkyl group, a C
3-12
cycloalkenyl group, or a group of the formula
wherein R
11
is a hydrogen atom, a C
1-12
straight- or branched-chain alkyl group, a C
2-12
straight- or branched-chain alkenyl group, a C
6-10
cycloalkyl group or a phenyl group; R
12
is a C
1-12
straight- or branched-chain alkyl group, a C
2-12
alkenyl group, a C
6-10
cycloalkyl group or a phenyl group; and R
13
and R
14
each represents a C
1-4
straight- or branched-chain alkylene group; with the proviso that R
8
is not
(3) an amide compound of the formula:
R
16
—CONH—R
15
—CONH—R
17
  (3)
wherein R
15
is a residue of a C
2-29
saturated or unsaturated aliphatic amino acid, a residue of a C
7-13
saturated or unsaturated alicyclic amino acid or a residue of a C
7-15
aromatic amino acid; R
16
and R
17
are the same or different and R
16
has the same meaning as R
9
or R
10
in the formula (2) and R
17
has the same meaning as R
2
or R
3
in the formula (1).
The present invention also provides a method for increasing the proportion of the &bgr;-crystal form in a crystalline polypropylene resin molded product which comprises molding the composition comprising a crystalline polypropylene resin and containing at least one amide compound of the above formulas (1), (2) and (3) in an amount effective for increasing the proportion of the &bgr;-crystal form.
Among these amide compounds of the formulas (1), (2) and (3), the compounds of the formula (1) and those of the formula (2) are preferred. Particularly preferred are amide compounds of the formula (1) wherein R
1
is —(CH
2
)
4
—,
and R
2
and R
3
are the same or different and each represents a C
6-8
cycloalkyl group or represents a phenyl group substituted by a C
1-4
alkyl or cyclohexyl group, and amide compounds of the formula (2) wherein R
8
is
and R
9
and R
10
are the same or different and each is a cyclohexyl group or a phenyl group.


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