Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2000-02-16
2002-03-19
Zitomer, Fred (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S240000, C526S303100, C526S304000, C526S307100, C526S310000, C526S312000, C526S321000, C526S328000
Reexamination Certificate
active
06359093
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
The present invention relates to an amphipathic compound, a high molecular compound using the same, and a process for producing the same.
Since the amphipathic compound of the present invention has at least one double bond in a molecule and is capable of polymerizing with various ethylenically unsaturated compounds, it is a useful compound as a raw material for a synthetic resin. Further, the amphipathic compound of the present invention is a compound which is classified as a reactive surfactant, and a high molecular compound obtained by copolymerizing the amphipathic compound of the present invention with an ethylenically unsaturated compound is used for plasticizers, heat resistant resins, lubricants, antistatic agents, paints, adhesives, dispersants, and additives for cement. A copolymer of the amphipathic compound of the present invention with a hydrophilic ethylenically unsaturated compound is soluble or dispersible in water and useful as a high molecular type surfactant. In particular, the copolymer with (meth)acrylamide has a high utility value as a novel paper making additive, which can improve sizing performance and paper reinforcing performance at the same time.
(2) Description of the Related Art
Japanese Patent Laid-open SHO 63-235595 and HEI 5-125681 disclose alkenyl succinic acid semi-ester and a reaction product of alkyl or alkenyl succinic acid with an alkylene oxide adduct of polyhydric alcohol. However, the amphipathic compound of the present invention is a novel compound which has not so far been reported. Further, the copolymer of the amphipathic compound of the present invention with an ethylenically unsaturated compound is also a novel compound which has not so far been reported.
SUMMARY OF THE INVENTION
An object of the present invention is to provide (1) a novel amphipathic compound having a succinic acid derivative skeleton with a polymerizable unsaturated bond, (2) a novel amphipathic compound having phthalic acid and its derivative skeletons, (3) a high molecular compound obtained by copolymerizing the amphipathic compound having a succinic acid derivative skeleton with a copolymerizable ethylenically unsaturated compound, (4) a high molecular compound obtained by copolymerizing the amphipathic compound having phthalic acid and its derivative skeletons with a copolymerizable ethylenically unsaturated compound, (5) a water soluble or dispersible high molecular compound obtained by copolymerizing the amphipathic compound having a succinic acid derivative skeleton with a hydrophilic ethylenically unsaturated compound, (6) a water soluble or dispersible high molecular compound obtained by copolymerizing the amphipathic compound having phthalic acid and its derivative skeletons with the copolymerizable, hydrophilic ethylenically unsaturated compound, and a paper making additive containing the water soluble or dispersible high molecular compounds of (5) and (6) as an active ingredient. Among them, particularly the copolymer with (meth)acrylamide is abbreviated as a PAM group sizing agent.
Further, an another object of the present invention is to provide (7) an emulsion having an ability to form a polymer film having excellent heat resistance and water resistance, in which the amphipathic compound of the present invention is used as an emulsifier, (8) a process for producing an amphipathic high molecular compound having a high molecular weight and a low viscosity by copolymerizing the amphipathic compound of the present invention with a hydrophilic ethylenically unsaturated compound in the presence of a colloidizing agent, and (9) a process for producing an emulsion having a heteromorphic structure, obtained by polymerizing a hydrophobic ethylenically unsaturated compound in the presence of the amphipathic compound of the present invention.
That is, the present invention relates to:
1) an amphipathic compound having a succinic acid skeleton represented by any of the following Formulas (1) to (4):
wherein R
1
is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R
2
and R
3
are independently a hydrogen atom or a methyl group; R
4
is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; M is a hydrogen atom, an alkali metal, or an ammonium group; and X is NH or N—(CH
2
—CH═CH
2
);
2) an amphipathic compound having a succinic acid skeleton represented by any of the following Formulas (5) to (8):
wherein R
1
is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R
2
and R
3
are independently a hydrogen atom or a methyl group; R
4
is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; Y is NH, N—(CH
2
—CH═CH
2
), or O; and m is an integer of 1 to 100;
3) an amphipathic compound in which R
1
in Formulas (1) to (4) of 1) is represented by any of the following Formulas (9) to (13):
wherein R
5
and R
6
are independently a hydrogen atom, or a linear alkyl group or alkenyl group of C
1
to C
23
, provided that a carbon number of (R
5
+R
6
) falls in a range of 3 to 45;
wherein n is an integer of 0 to 6;
wherein p is an integer of 0 to 6;
4) an amphipathic compound in which R
1
in Formulas (5) to (8) of 2) is represented by any of the following Formulas (9) to (13):
wherein R
5
and R
6
are independently a hydrogen atom, or a linear alkyl group or alkenyl group of C
1
to C
23
, provided that a carbon number of (R
5
+R
6
) falls in a range of 3 to 45;
wherein n is an integer of 0 to 6;
wherein p is an integer of 0 to 6;
5) an amphipathic compound having any of phthalic acid or tetrahydrophthalic acid, hexahydrophthalic acid, norbornenedicarboxylic acid, and norbornanedicarboxylic acid structures represented by following Formulas (14) to (17):
wherein R
7
and R
8
are independently a hydrogen atom or a methyl group; R
9
is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; R
10
and R
11
are independently a hydrogen atom or a methyl group; M is a hydrogen atom, an alkali metal, or an ammonium group; and X is NH or N—(CH
2
—CH═CH
2
);
6) a high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of an amphipathic compound having a succinic acid skeleton represented by any of Formulas (18) to (21) or a mixture thereof with 10.0 to 99.9 weight % of a copolymerizable ethylenically unsaturated compound:
wherein R
1
is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R
2
and R
3
are independently a hydrogen atom or a methyl group; R
4
is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; M is a hydrogen atom, an alkali metal, or an ammonium group; and Y is NH, N—(CH
2
—CH═CH
2
), or O;
7) a water soluble or dispersible amphipathic high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (18) to (21) as described in 6) or a mixture thereof with 10.0 to 99.9 weight % of a hydrophilic ethylenically unsaturated compound;
8) a paper making additive containing the water soluble or dispersible amphipathic high molecular compound as described in 7) as an active ingredient;
9) a high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (5) to (8) as described in 2) or a mixture thereof with 10.0 to 99.9 weight % of a copolymerizable ethylenically unsaturated compound;
10) a water soluble or dispersible amphipathic high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (5) to (8) as described in 2) or a mixture
Oyanagi Shoko
Takaki Toshihiko
Tanabe Masaru
Burns Doane Swecker & Mathis L.L.P.
Mitsui Chemicals Inc.
Zitomer Fred
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