Ink composition

Information

  • Patent Grant
  • 8530538
  • Patent Number
    8,530,538
  • Date Filed
    Wednesday, March 29, 2006
    19 years ago
  • Date Issued
    Tuesday, September 10, 2013
    11 years ago
Abstract
An ultraviolet hardenable ink composition excelling in the wetting characteristic (repellence prevention) of ink having impacted a recording medium. There is provided an ultraviolet hardenable ink composition characterized by containing a polyester-modified polydimethylsiloxane as a surfactant in an amount of 0.01 to 1% based on the ultraviolet hardenable ink. Preferably, at least allyl glycol and/or a N-vinyl compound is contained as a polymerizable compound. Incorporation of the polyester-modified polydimethylsiloxane in the surfactant has realized enhancing of the wetting characteristic on all nonabsorptive material surfaces and avoiding of ink repellence.
Description
TECHNICAL FIELD

The present invention relates to an ink composition. More particularly, the invention relates to an ultraviolet curing type ink composition which is curable by ultraviolet light, and excellent in ejection stability and wettability (prevention of repellency) of an ink landed on a recording medium.


BACKGROUND ART

An ink jet recording method is a printing method in which droplets of an ink composition are allowed to fly and deposited on a recording medium such as paper to perform printing. This ink jet recording method is characterized by that images having high resolution and high quality can be printed at high speed. The ink composition used in the ink jet recording method is generally one mainly comprising an aqueous solvent and containing a coloring component and a wetting agent such as glycerin for the purpose of preventing clogging.


Further, when printing is performed on a recording medium such as paper or cloth that is hard for the aqueous ink composition to penetrate thereinto, or a plate or a film made of a material such as metal or plastics into which the aqueous ink composition does not penetrate, for example, a resin such as a phenol, melamine, vinyl chloride, acrylic or polycarbonate resin, the ink composition is required to contain a component which can allow the coloring material to be stably fixed to the recording medium. In particular, when printing is performed on a printed-circuit board or the like, the ink composition is required to have quick drying properties and solvent resistance.


To such a demand, there has hitherto been proposed an ink composition comprising a component polymerizable by ultraviolet irradiation (for example, see patent document 1). Further, an ultraviolet curing type ink composition comprising a coloring material, an ultraviolet curing agent, a photopolymerization initiator and the like has been proposed (for example, see patent document 2). According to these ink compositions and ink jet recording methods, it is disclosed that blurring of the ink composition on the recording medium can be prevented to improve image quality.


In the ink jet recording method using the ink composition comprising the component polymerizable by ultraviolet irradiation as described above, an ultraviolet lay is irradiated after the ink composition has been deposited on the recording medium. Thereupon, the photopolymerization initiator in the ink composition forms radicals, thereby initiating polymerization of an oligomer and a monomer to cause curing. Accordingly, the coloring material in the ink composition is firmly fixed onto the recording medium. It is considered that printing which is high in film strength, solvent resistance and color density and decreased in blurring and unevenness can be realized by this firm fixing.


However, the ultraviolet curing type ink composition comprising the coloring material, the ultraviolet curing agent, the photopolymerization initiator and the like as described above has insufficient wettability to a surface of a nonabsorbable material such as glass or metal, so that repellency occurs on a print surface and at an interface at the time when recoating has been performed, resulting in failure to obtain a clear color image.


There is disclosed an ink composition in which a polyether-modified silicone oil is allowed to be contained as a surface tension regulator in an ultraviolet curing type ink composition for the purpose of improving wettability to a surface of a nonabsorbable material (for example, see patent document 3). However, the polyether-modified silicone oil improves wettability to only a surface of a specific nonabsorbable material, so that it is unsatisfactory.


Patent Document 1: JP-A-3-216379


Patent Document 2: U.S. Pat. No. 5,623,001


Patent Document 1: JP-A-2003-147233


DISCLOSURE OF THE INVENTION
Problems to be Solved by the Invention

It is therefore an object of the invention to solve the above-mentioned problems and to provide an ultraviolet curing type ink composition excellent in wettability to surfaces of all nonabsorbable materials.


Means for Solving the Problems

The present inventors have conducted intensive studies, and as a result, have found that the use of a polyester-modified polydimethylsiloxane can improve wettability to surfaces of all nonabsorbable materials and can prevent repellency of an ink, thus completing the invention.


That is to say, the invention is achieved by the following constitution:


(1) An ink composition comprising at least a polymerizable compound, a photopolymerization initiator, a surfactant and a coloring material, which contains a polyester-modified polydimethylsiloxane as the surfactant in an amount of 0.01% to 1%.


(2) The ink composition of (1), which contains no solvent.


(3) The ink composition of (1) or (2), which contains at least allyl glycol and/or an N-vinyl compound as the polymerizable compound.


(4) The ink composition of (3), which contains the allyl glycol and/or N-vinyl compound in an amount of 20% to 80%.


(5) The ink composition of (3) or (4), wherein the above-mentioned N-vinyl compound is N-vinylformamide.


The ultraviolet curing type ink of the invention contains the polyester-modified polydimethylsiloxane as the surfactant in an amount of 0.01% to 1%, thereby being able to improve wettability to surfaces of all nonabsorbable materials to prevent repellency of the ink.







BEST MODE FOR CARRYING OUT THE INVENTION

The polyester-modified polydimethylsiloxanes used as the surfactant in the invention include one in which polyester groups are introduced into part of methyl groups of a dimethylsiloxane. Examples thereof include one known by the trade name BYK-UV3570 (manufactured by BYK-Chemie Japan K.K.) and the like. Modified polydimethylsiloxanes also include modified polydimethylsiloxanes in which various organic groups are introduced, such as polyether—modified polydimethylsiloxanes (which include, for example, those known by the trade names KF-351 and 945 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF 4440 and 4460 (manufactured by GE Toshiba Silicone Co., Ltd.), BYK-307, 333 and 348 (manufactured by BYK-Chemie Japan K.K.) and the like), amino-modified polydimethylsiloxanes (which include, for example, those known by the trade names KF-8012 and 865 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF 4700 and 4701 (manufactured by GE Toshiba Silicone Co., Ltd.) and the like), carbinol-modified polydimethylsiloxanes (which include, for example, those known by the trade names KF-6001 and 6002 (manufactured by Shin-Etsu Chemical Co., Ltd.), XF 42-B0970 (manufactured by GE Toshiba Silicone Co., Ltd.) and the like) and alkyl-modified polydimethylsiloxanes (which include, for example, those known by the trade names KF-412, 413 and 414 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF 4421 (manufactured by GE Toshiba Silicone Co., Ltd.) and the like), as well as the polyester-modified polydimethylsiloxanes. However, in order to improve wettability of an ink composition on surfaces of all nonabsorbable materials and also improve prevention of repellency of an ink, it is necessary to use the polyester-modified polydimethylsiloxanes.


Further, the polyester-modified polydimethylsiloxane used as the surfactant in the invention is preferably used at a compounding ratio to the ink composition ranging from 0.01% to 1% in order to improve wettability to the surface of the nonabsorbable material.


The coloring material contained in the ultraviolet curing type ink used in the invention may be either a dye or a pigment. However, the pigment is more advantageous in terms of durability of printed matter.


As the dyes used in the invention, there can be used various dyes which are generally used for ink jet recording, such as a direct dye, an acid dye, a food dye, a basic dye, a reactive dye, a disperse dye, a vat dye, a soluble vat dye and a reactive disperse dye.


As the pigments used in the invention, inorganic pigments and organic pigments can be used without particular limitation.


As the inorganic pigments, there can be used carbon blacks produced by known processes such as a contact process, a furnace process and a thermal process, as well as titanium oxide and iron oxide.


Further, as the organic pigments, there can be used azo pigments (including an azo lake, an insoluble azo pigment, a condensed azo pigment, a chelate azo pigment and the like), polycyclic pigments (for example, a phthalocyanine pigment, a perylene pigment, a perynone pigment, an anthraquinone pigment, a quinacridone pigment, a dioxazine pigment, a thioindigo pigment, an isoindolinone pigment, a quinophthalone pigment and the like), dye chelates (for example, a basic dye type chelate, acid dye type chelate and the like), nitro pigments, nitroso pigments, aniline black and the like.


Specific examples of the pigments as carbon blacks include No. 2300, No. 900, MCF88, No. 33, No. 40, No. 45, No. 52, MA7, MA8, MA100, No2200B and the like manufactured by Mitsubishi Chemical Corporation, Raven 5750, Raven 5250, Raven 5000, Raven 3500, Raven 1255, Raven 700 and the like manufactured by Columbia Co., Regal 400R, Regal 330R, Regal 660R, Mogul L, Mogul 700, Monarch 800, Monarch 880, Monarch 900, Monarch 1000, Monarch 1100, Monarch 1300, Monarch 1400 and the like manufactured by Cabot Co., Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color Black FW200, Color Black S150, Color Black S160, Color Black S170, Printex 35, Printex U, Printex V, Printex 140U, Special Black 6, Special Black 5, Special Black 4A, Special Black 4 and the like manufactured by Degussa Co., C.I. Pigment Black 7 and the like.


The pigments used in yellow inks include C.I. Pigment Yellow 1, 2, 3, 12, 13, 14, 16, 17, 73, 74, 75, 83, 93, 95, 97, 98, 109, 110, 114, 128, 129, 138, 150, 151, 154, 155, 180 185 and the like.


Further, the pigments used in magenta inks include C.I. pigment red 5, 7, 12, 48(Ca), 48(Mn), 57(Ca), 57:1, 112, 122, 123, 168, 184, 202 and 209, C.I. Pigment Violet 19 and the like.


Furthermore, the pigments used in cyan inks include C.I. pigment blue 1, 2, 3, 15:3, 15:4, 60, 16 and 22.


According to a preferred embodiment of the ultraviolet curing type ink of the invention, the average particle size of the pigment ranges preferably from 10 to 200 nm, and more preferably from about 50 to 150 nm.


Further, The amount of the coloring material added in the ultraviolet curing type ink composition preferably ranges from about 0.1 to 25% by weight, and more preferably from about 0.5 to 15% by weight.


These pigments are preferably added to the ink composition as pigment dispersions obtained by dispersing them in aqueous media or polymerizable compounds with dispersing agents. As the preferred dispersing agents, there can be used dispersing agents which are conventionally used for preparing pigment dispersions, for example, polymeric dispersing agents.


The photopolymerization initiator contained in the ultraviolet curing type ink used in the invention is, for example, one which absorbs ultraviolet light in a region of about 200 nm to 450 nm or visible light to form radicals or ions, thereby initiating polymerization of the polymerizable compound.


Typical examples of the photopolymerization initiators used in the invention include benzoin methyl ether, benzoin ethyl ether, isopropyl benzoin ether, isobutyl benzoin ether, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, benzyl, diethoxyacetophenone, benzophenone, chlorothioxantone, 2-chlorothioxantone, isopropylthioxantone, 2-methylthioxantone, polychlorinated polyphenyl, hexachlorobenzene and the like, and preferred are isobutyl benzoin ether and 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime.


Further, there can also be used photopolymerization initiators available under the trade names of Vicure 10 and 30 (manufactured by Stauffer Chemical), Irgacure 184, 651, 2959, 907, 369, 1700, 1800, 1850, 819, 127, 379, 754, 500, 1300, 1870, 784, 250 and OXE01, and Darocur 1173, 4265 and TPO (manufactured by Ciba Specialty Chemicals), Quantacure CTX and ITX (manufactured by Aceto Chemical) and Lucirin TPO (manufactured by BASF).


It is preferred that at least allyl glycol and/or an N-vinyl compound are contained as the polymerizable compound contained in the ultraviolet curing type ink used in the invention.


Further, in the ultraviolet curing type ink composition, the allyl glycol and/or N-vinyl compound are preferably contained in an amount of 20% to 80%.


The N-vinyl compounds include N-vinylformamide, N-vinylcarbazole, N-vinylacetamide, N-vinylpyrrolidone, N-vinylcaprolactam, derivatives thereof and the like.


Further, the polymerizable compound contained in the ultraviolet curing type ink used in the invention may contain a different polymerizable compound other than allyl glycol and/or the N-vinyl compound, as the polymerizable compound.


The different polymerizable compound is not particularly limited, as long as it is polymerized by radicals or ions generated from the photopolymerization initiator. Such a polymerizable compound means a molecule which can form a constituent unit of a basic structure of a polymer. Such a polymerizable compound is also called a photopolymerizable monomer, and includes a monofunctional acrylate and methacrylate and a multifunctional acrylate and methacrylate.


Typical ones of such polymerizable compounds include 1,3-butylene glycol diacrylate, 1,5-pentanediol diacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,8-octanediol diacrylate, 1,9-nonanediol diacrylate, tricyclodecane-dimethanol diacrylate, polyethylene glycol diacrylate, propylene glycol diacrylate, dipropylene glycol diacrylate, polypropylene glycol diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, neopentyl glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, hydroxypiopelinic acid ester neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, t-butyl acrylate, isooctyl acrylate, lauryl acrylate, stearyl acrylate, cyclohexyl acrylate, methoxytriethylene acrylate, ethylcarbitol acrylate, 2-phenoxyethyl acrylate, dipentaerythritol polyacrylate, tripropylene glycol diacrylate, glycerin EO adduct triacrylate, isobonyl acrylate, 2-methoxyethyl acrylate, 3-methoxybutyl acrylate, 2-ethoxyethyl acrylate and the like.


A polymerization accelerator contained in the ultraviolet curing type ink used in the invention is not particularly limited. In particular, however, an aminobenzoate derivative is preferred in terms of the problem of odor and more reliable curing of the ultraviolet curing type ink composition. This is because the aminobenzoate derivative reduces polymerization inhibition caused by oxygen.


Typical ones of such aminobenzoate derivatives include ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate and the like. These are available under the trade names of Darocur EDB and EHA (manufactured by Ciba Specialty Chemicals) and the like.


The ultraviolet curing type ink used in the invention may contain an aqueous solvent. Further, as an arbitrary component, there may be added a resin emulsion, an inorganic oxide colloid, a wetting agent, a pH adjuster, a preservative, a mildewproofing agent or the like.


Furthermore, it is more preferred that the ultraviolet curing type ink used in the invention contains no organic solvent and is an ultraviolet curing type ink of a non-solvent type.


The ultraviolet curing type ink composition used in the invention is deposited on a substrate, a recording medium or the like by coating, ejection by an ink jet recording method, and the like, and then, irradiated with ultraviolet light.


The ultraviolet dose varies depending on the amount of the ultraviolet curing type ink composition deposited on a substrate, a recording medium or the like and the thickness thereof, and can not be exactly specified. Preferred conditions should be appropriately selected. For example, however, it ranges from 10 mJ/cm2 to 10,000 mJ/cm2, and preferably ranges from 50 mJ/cm2 to 6,000 mJ/cm2. When the ultraviolet dose is within such a range, the curing reaction can be sufficiently performed.


Further, as the ultraviolet light to be irradiated, it is preferred in terms of safety and environment that ultraviolet light in a long wavelength region of 350 nm or more which generates no ozone is used. Furthermore, it is preferred that the ultraviolet light to be irradiated is not one having a continuous spectrum, but one having a narrow light emission peak width. The wavelength region of this light emission peak is preferably within the range of 350 to 420 nm.


Although means for ultraviolet irradiation are not particularly limited, ultraviolet light emitting semiconductor elements such as ultraviolet LEDs and ultraviolet light emitting semiconductor lasers are preferred in terms of energy consumption, miniaturization and the life of lamps. When the ultraviolet LEDs are used, it is preferred that, for example, an LED having a light emitting peak wavelength of 365 nm, an LED having a light emitting peak wavelength of 380 nm and an LED having a light emitting peak wavelength of 395 nm are combined.


Other means for ultraviolet irradiation include lamps such as a metal halide lamp, a xenon lamp, a carbon arc lamp, a chemical lamp, a low-pressure mercury lamp and a high-pressure mercury lamp. For example, commercially available lamps such as H Lamp, D Lamp and V Lamp manufactured by Fusion System can also be used.


Further, in a recording method using the ultraviolet curing type ink composition of the invention, heating may be performed before, concurrently with or after ultraviolet light irradiation. Heating includes a method of heating by bringing a heat source into contact with the recording medium, a method of heating without contact with the recording medium, for example, by irradiating an infrared ray or a microwave (an electromagnetic wave having the maximum wavelength at about 2,450 MHz) or by blowing hot air, and the like.


EXAMPLES

The invention will be illustrated in greater detail with reference to the following Examples, but the invention should not be construed as being limited thereto.


Ink compositions having respective compositions shown in Tables 1 to 4 were each prepared.









TABLE 1







Black
















Comparative
Comparative
Comparative
Comparative



Example 1
Example 2
Example 1
Example 2
Example 3
Example 4

















Allyl Glycol
55.2







N-Vinylformamide

55.2
55.2
55.2
55.2
55.3


Tripropylene Glycol Diacrylate
20
20
20
20
20
20


EO Adduct Trimethylolpropane
15
15
15
15
15
15


Triacrylate


Irgacure 1800
5
5
5
5
5
5


Darocur EHA
1
1
1
1
1
1


BYK-UV3570
0.1
0.1


BYK-307


0.1


KF-945



0.1


KF-96L




0.1


Pigment Black-7
3
3
3
3
3
3


Dispersing Agent (Polyoxyalkylene-
0.7
0.7
0.7
0.7
0.7
0.7


polyalkylenepolyamine)
















TABLE 2







Cyan
















Comparative
Comparative
Comparative
Comparative



Example 3
Example 4
Example 5
Example 6
Example 7
Example 8

















Allyl Glycol
55.2







N-Vinylformamide

55.2
55.2
55.2
55.2
55.3


Tripropylene Glycol Diacrylate
20
20
20
20
20
20


EO Adduct Trimethylolpropane
15
15
15
15
15
15


Triacrylate


Irgacure 1800
5
5
5
5
5
5


Darocur EHA
1
1
1
1
1
1


BYK-UV3570
0.1
0.1


BYK-307


0.1


KF-945



0.1


KF-96L




0.1


Pigment Blue-15:3
3
3
3
3
3
3


Dispersing Agent (Polyoxyalkylene-
0.7
0.7
0.7
0.7
0.7
0.7


polyalkylenepolyamine)
















TABLE 3







Magenta
















Comparative
Comparative
Comparative
Comparative



Example 5
Example 6
Example 9
Example 10
Example 11
Example 12

















Allyl Glycol
55







N-Vinylformamide

55
55
55
55
55.1


Tripropylene Glycol Diacrylate
20
20
20
20
20
20


EO Adduct Trimethylolpropane
15
15
15
15
15
15


Triacrylate


Irgacure 1800
5
5
5
5
5
5


Darocur EHA
1
1
1
1
1
1


BYK-UV3570
0.1
0.1


BYK-307


0.1


KF-945



0.1


KF-96L




0.1


Pigment Violet-19
3
3
3
3
3
3


Dispersing Agent (Polyoxyalkylene-
0.9
0.9
0.9
0.9
0.9
0.9


polyalkylenepolyamine
















TABLE 4







Yellow
















Comparative
Comparative
Comparative
Comparative



Example 7
Example 8
Example 13
Example 14
Example 15
Example 16

















Allyl Glycol
55.3







N-Vinylformamide

55.3
55.3
55.3
55.3
55.4


Tripropylene Glycol Diacrylate
20
20
20
20
20
20


EO Adduct Trimethylolpropane
15
15
15
15
15
15


Triacrylate


Irgacure 1800
5
5
5
5
5
5


Darocur EHA
1
1
1
1
1
1


BYK-UV3570
0.1
0.1


BYK-307


0.1


KF-945



0.1


KF-96L




0.1


Pigment Yellow-155
3
3
3
3
3
3


Dispersing Agent (Polyoxyalkylene-
0.6
0.6
0.6
0.6
0.6
0.6


polyalkylenepolyamine)









Allyl glycol (manufactured by Nippon Nyukazai Co., Ltd.)


N-Vinylformamide (manufactured by Arakawa Chemical Industries Ltd., trade name: Beamset 770)


Tripropylene glycol diacrylate (manufactured by Toagosei Co., Ltd, trade name: Aronix M-220)


EO adduct trimethylolpropane triacrylate (manufactured by Dai-Ichi Kogyo Seiyaku Co., Ltd., trade name: New Frontier TMP-3P)


Irgacure 1800 (manufactured by Ciba Specialty Chemicals)


Darocur EHA (manufactured by Ciba Specialty Chemicals)


BYK-UV3570 (polyester-modified polydimethylsiloxane, manufactured by BYK-Chemie Japan K.K.)


BYK-307 (polyether-modified polydimethylsiloxane, manufactured by BYK-Chemie Japan K.K.)


KF-945 (polyether-modified polydimethylsiloxane, manufactured by Shin-Etsu Chemical Co., Ltd.)


KF-96L (polydimethylsiloxane, manufactured by Shin-Etsu Chemical Co., Ltd.)


Curing Test


The above-mentioned ultraviolet curing type ink composition was dropped onto a glass substrate, and treated under curing conditions of an ultraviolet wavelength of 365 nm, an irradiation intensity of 17 mW/cm2, an irradiation time of 6 seconds and an integrated light volume of 102 mJ/cm2. Then, the following visual evaluation of a surface state was conducted.


The results are shown in Table 5.









TABLE 5





Curing Test
























Comparative
Comparative
Comparative
Comparative



Example 1
Example 2
Example 1
Example 2
Example 3
Example 4





Surface State
A
A
B
C
C
D








Comparative
Comparative
Comparative
Comparative



Example 3
Example 4
Example 5
Example 6
Example 7
Example 8





Surface State
A
A
B
C
C
D








Comparative
Comparative
Comparative
Comparative



Example 5
Example 6
Example 9
Example 10
Example 11
Example 12





Surface State
A
A
B
B
C
C








Comparative
Comparative
Comparative
Comparative



Example 7
Example 8
Example 13
Example 14
Example 15
Example 16





Surface State
A
A
B
B
C
D









Evaluation Indexes


A: Cured in a smooth surface state.


B: A surface state was smooth, but wrinkles slightly occurred at an interface with the glass.


C: Wrinkles slightly occurred by curing contraction.


D: Wrinkles occurred all over a surface by curing contraction.


Print Test


Utilizing an ink jet printer, PM-G900, manufactured by Seiko Epson Corporation, solid pattern printing was performed at ordinary temperature and ordinary pressure using the above-mentioned ink compositions and a PVC sheet (manufactured by Lintec Corporation, Viewcal 900), an OHP film (manufactured by Fuji Xerox Co., Ltd., XEROX FILM <unframed>) and a PC sheet (manufactured by Teijin Chemicals Ltd. Printing and curing treatment were performed at the same time by means of an ultraviolet irradiation equipment installed at a delivery port under such curing conditions as to give an integrated light amount of 90 mJ/cm2. The following visual evaluation of a surface state was conducted.


The results are shown in Table 6.


Evaluation Indexes


A: There is no repellency, and edge portions are sharp. The effect is sufficient.


B: There is no repellency, but edge portions lack in sharpness.


C: Somewhat repelled. The effect is insufficient.


D: Almost repelled. There is no effect.









TABLE 6





Print Test
























Comparative
Comparative
Comparative
Comparative



Example 1
Example 2
Example 1
Example 2
Example 3
Example 4





PVC Sheet
A
A
B
C
C
D


OHP Film
A
A
C
D
D
D


PC Sheet
A
A
C
C
D
D








Comparative
Comparative
Comparative
Comparative



Example 3
Example 4
Example 5
Example 6
Example 7
Example 8





PVC Sheet
A
A
B
B
C
D


OHP Film
A
A
C
C
D
D


PC Sheet
A
A
C
C
D
D








Comparative
Comparative
Comparative
Comparative



Example 5
Example 6
Example 9
Example 10
Example 11
Example 12





PVC Sheet
A
A
B
B
B
C


OHP Film
A
A
B
C
C
D


PC Sheet
A
A
C
C
C
D








Comparative
Comparative
Comparative
Comparative



Example 7
Example 8
Example 13
Example 14
Example 15
Example 16





PVC Sheet
A
A
B
B
C
D


OHP Film
A
A
C
C
D
D


PC Sheet
A
A
C
C
D
D









With respect to the ultraviolet curing type inks of Examples to which the polyester-modified polydimethylsiloxane was added, clear printed matter having no repellency was obtained, regardless of the recording medium.

Claims
  • 1. An ultraviolet curing inkjet ink composition comprising at least a polymerizable compound, a photopolymerization initiator, a surfactant and a coloring material, which contains a polyester-modified polydimethylsiloxane as the surfactant in an amount of 0.01% to 1%.
  • 2. The ultraviolet curing inkjet ink composition according to claim 1, which contains no solvent.
  • 3. The ultraviolet curing inkjet ink composition according to claim 1, which contains at least allyl glycol and/or an N-vinyl compound as the polymerizable compound.
  • 4. The ultraviolet curing inkjet ink composition according to claim 3, which contains the allyl glycol and/or N-vinyl compound in an amount of 20% to 80%.
  • 5. The ultraviolet curing inkjet ink composition according to claim 3, wherein the N-vinyl compound is N-vinylformamide.
  • 6. The ultraviolet curing inkjet ink composition according to claim 2, which contains at least allyl glycol and/or an N-vinyl compound as the polymerizable compound.
  • 7. The ultraviolet curing inkjet ink composition according to claim 4, wherein the N-vinyl compound is N-vinylformamide.
  • 8. The ultraviolet curing inkjet ink composition according to claim 1, which is to be used in a recording method in which the ultraviolet curing inkjet ink composition is cured by irradiating an ultraviolet ray by an ultraviolet LED having a light emission peak within a wavelength region of 350 to 420 nm.
  • 9. The ultraviolet curing inkjet ink composition according to claim 1, which is to be used in a recording method in which the ultraviolet curing inkjet ink composition is cured by irradiating an ultraviolet ray with an ultraviolet dose within a range of from 50 mJ/cm2 to 6,000 mJ/cm2.
  • 10. The ultraviolet curing inkjet ink composition according to claim 1, wherein the photopolymerization initiator is a photopolymerization initiator which absorbs ultraviolet light in a region of 200 nm to 450 nm or visible light to form radicals or ions, thereby initiating polymerization of the polymerizable compound.
  • 11. The ultraviolet curing inkjet ink composition according to claim 1, which is to be used on a surface of a nonabsorbable material.
  • 12. The ultraviolet curing inkjet ink composition according to claim 1, wherein the coloring material is a pigment.
  • 13. The ultraviolet curing inkjet ink composition according to claim 1, wherein the polymerizable compound includes at least one of a monofunctional acrylate, a monofunctional methacrylate, a multifunctional acrylate and a multifunctional methacrylate.
Priority Claims (2)
Number Date Country Kind
2005-094829 Mar 2005 JP national
2006-058694 Mar 2006 JP national
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/JP2006/306457 3/29/2006 WO 00 8/26/2009
Publishing Document Publishing Date Country Kind
WO2006/104192 10/5/2006 WO A
US Referenced Citations (206)
Number Name Date Kind
3582487 Fuhr et al. Jun 1971 A
3607693 Heine et al. Sep 1971 A
3720635 Metzner et al. Mar 1973 A
3929693 Hochberg Dec 1975 A
4007144 Sanders et al. Feb 1977 A
4129486 Deutsch et al. Dec 1978 A
4133793 Lewis et al. Jan 1979 A
4190602 Brunisholz et al. Feb 1980 A
4233195 Mills Nov 1980 A
4239866 Reitel et al. Dec 1980 A
4239966 Wang Dec 1980 A
4308400 Felder et al. Dec 1981 A
4315807 Felder et al. Feb 1982 A
4318791 Felder et al. Mar 1982 A
4320186 Kato et al. Mar 1982 A
4321118 Felder et al. Mar 1982 A
4347111 Gehlhaus et al. Aug 1982 A
4370379 Kato et al. Jan 1983 A
4450279 Shirosaki et al. May 1984 A
4477681 Gehlhaus et al. Oct 1984 A
4507466 Tomalia et al. Mar 1985 A
4522693 Henne et al. Jun 1985 A
4558120 Tomalia et al. Dec 1985 A
4568737 Tomalia et al. Feb 1986 A
4587329 Tomalia et al. May 1986 A
4631337 Tomalia et al. Dec 1986 A
4694064 Tomalia et al. Sep 1987 A
4721734 Gehlhaus et al. Jan 1988 A
4830902 Plantenga et al. May 1989 A
4922004 Kohler et al. May 1990 A
5041516 Frechet et al. Aug 1991 A
5077402 Desobry et al. Dec 1991 A
5212212 Fonda May 1993 A
5221334 Ma et al. Jun 1993 A
5453121 Nicholls et al. Sep 1995 A
5609671 Nagasawa Mar 1997 A
5623001 Figov Apr 1997 A
5662736 Sakai et al. Sep 1997 A
5662738 Schmid et al. Sep 1997 A
5690723 Sano et al. Nov 1997 A
5846306 Kubota et al. Dec 1998 A
5903290 Nicoloff, Jr. et al. May 1999 A
5928419 Uemura et al. Jul 1999 A
5952401 Kimura et al. Sep 1999 A
5958121 Lin Sep 1999 A
5976233 Osumi et al. Nov 1999 A
6030441 Kubota et al. Feb 2000 A
6087416 Pearlstine et al. Jul 2000 A
6114404 Deeken et al. Sep 2000 A
6117606 Macholdt et al. Sep 2000 A
6123759 Mise et al. Sep 2000 A
6136286 Okuyama et al. Oct 2000 A
6179415 Okazaki et al. Jan 2001 B1
6187897 Kawashima et al. Feb 2001 B1
6300388 Verdonck et al. Oct 2001 B1
6322188 Sano Nov 2001 B1
6331111 Cao Dec 2001 B1
6332291 Flosbach et al. Dec 2001 B1
6341841 Shimada et al. Jan 2002 B1
6395079 Sano May 2002 B1
6419733 Sano et al. Jul 2002 B1
6428862 Noguchi Aug 2002 B1
6433038 Tanabe et al. Aug 2002 B1
6444019 Zou et al. Sep 2002 B1
6488751 Takemoto Dec 2002 B1
6491748 Watanabe Dec 2002 B2
6518370 Abuelyaman et al. Feb 2003 B2
6558460 Walker et al. May 2003 B1
6558753 Ylitalo et al. May 2003 B1
6602333 Miyabayashi Aug 2003 B2
6637850 Shimada et al. Oct 2003 B2
6653367 Miyabayashi Nov 2003 B2
6654367 Kaufman Nov 2003 B1
6664306 Gaddam et al. Dec 2003 B2
6726756 Zou et al. Apr 2004 B1
6793313 Adachi et al. Sep 2004 B1
6793318 Saksa Sep 2004 B2
6846074 Hirai Jan 2005 B2
6846851 Nakhmanovich et al. Jan 2005 B2
6849110 Sano Feb 2005 B2
6869470 Kato Mar 2005 B2
6877851 Watanabe Apr 2005 B2
6890049 Shimada et al. May 2005 B2
6924327 Sano et al. Aug 2005 B2
6989054 Tanabe et al. Jan 2006 B2
7008475 Randler et al. Mar 2006 B2
7025449 Simons et al. Apr 2006 B2
7040747 Kubota et al. May 2006 B2
7064153 Bruck Jun 2006 B2
7156909 Oyanagi et al. Jan 2007 B2
7259100 Zurcher et al. Aug 2007 B2
7285592 Harz et al. Oct 2007 B2
7296883 Kanaya et al. Nov 2007 B2
7303619 Oyanagi Dec 2007 B2
7348128 Yamada et al. Mar 2008 B2
7384472 Schweikart et al. Jun 2008 B2
7419255 Kawaguchi et al. Sep 2008 B2
7438405 Ichizawa et al. Oct 2008 B2
7513945 Nakano et al. Apr 2009 B2
7538144 Vanmaele et al. May 2009 B2
7581829 Oyanagi et al. Sep 2009 B2
7591889 Stoffel et al. Sep 2009 B2
7604693 Oyanagi et al. Oct 2009 B2
7619015 Oyanagi et al. Nov 2009 B2
7670418 Kato et al. Mar 2010 B2
7732505 Kito et al. Jun 2010 B2
7753514 Nakano et al. Jul 2010 B2
7790245 Oyanagi et al. Sep 2010 B2
7828888 Itano et al. Nov 2010 B2
7846246 Oyanagi et al. Dec 2010 B2
7850280 Oyanagi et al. Dec 2010 B2
7854798 Udagawa et al. Dec 2010 B2
7855041 Weber et al. Dec 2010 B2
7866807 Makuta et al. Jan 2011 B2
7968621 Oyanagi et al. Jun 2011 B2
8044116 Idemura et al. Oct 2011 B2
20030017353 Yamaguchi et al. Jan 2003 A1
20030050379 Shih et al. Mar 2003 A1
20030089271 Hirano et al. May 2003 A1
20030144377 Sano et al. Jul 2003 A1
20030153649 Bromberg Aug 2003 A1
20030157356 Tamura et al. Aug 2003 A1
20030176566 Wight et al. Sep 2003 A1
20030222959 Yamanouchi et al. Dec 2003 A1
20030231234 Ushirogouchi et al. Dec 2003 A1
20040021753 Yoshihiro et al. Feb 2004 A1
20040069183 Kamoto et al. Apr 2004 A1
20040257419 Iinuma et al. Dec 2004 A1
20040266907 Sugita et al. Dec 2004 A1
20050039631 Best et al. Feb 2005 A1
20050159501 Kiefer-Liptak Jul 2005 A1
20050176841 Krohn Aug 2005 A1
20050176847 Cagle Aug 2005 A1
20050197418 Graziano et al. Sep 2005 A1
20050197419 Graziano et al. Sep 2005 A1
20050282930 Fu et al. Dec 2005 A1
20060009546 Brown Jan 2006 A1
20060014849 Vanmaele et al. Jan 2006 A1
20060014850 Vanmaele et al. Jan 2006 A1
20060036001 Oyanagi et al. Feb 2006 A1
20060092254 Claes et al. May 2006 A1
20060158493 Nakano et al. Jul 2006 A1
20060160917 Oyanagi et al. Jul 2006 A1
20060189712 Kondo Aug 2006 A1
20060211788 Krohn Sep 2006 A1
20060229382 Schweikart et al. Oct 2006 A1
20060268084 Nishizaki et al. Nov 2006 A1
20070022547 O'Brien Feb 2007 A1
20070037961 Oyanagi et al. Feb 2007 A1
20070044684 Nakano et al. Mar 2007 A1
20070046720 Konno et al. Mar 2007 A1
20070060670 Ellis Mar 2007 A1
20070076069 Edwards et al. Apr 2007 A1
20070120926 Doumaux et al. May 2007 A1
20070129457 Nakano et al. Jun 2007 A1
20070142501 Oyanagi et al. Jun 2007 A1
20070148585 Kaneko et al. Jun 2007 A1
20070222811 Yanagi Sep 2007 A1
20070224345 Metz et al. Sep 2007 A1
20070249750 Oyanagi et al. Oct 2007 A1
20070281141 Kohlweyer Dec 2007 A1
20080022893 Mizutani Jan 2008 A1
20080024577 Nakano et al. Jan 2008 A1
20080028980 Aoki et al. Feb 2008 A1
20080081119 Oyanagi et al. Apr 2008 A1
20080090931 Nagvekar et al. Apr 2008 A1
20080096998 Oyanagi et al. Apr 2008 A1
20080098928 Oyanagi et al. May 2008 A1
20080125511 Nakano et al. May 2008 A1
20080132599 Nakano et al. Jun 2008 A1
20080145628 Oyanagi et al. Jun 2008 A1
20080146689 Oyanagi et al. Jun 2008 A1
20080152825 Mukai et al. Jun 2008 A1
20080152828 Mukai et al. Jun 2008 A1
20080152877 Mukai et al. Jun 2008 A1
20080173214 Oyanagi et al. Jul 2008 A1
20080182083 Oyanagi et al. Jul 2008 A1
20080182085 Oyanagi et al. Jul 2008 A1
20080207805 Blease et al. Aug 2008 A1
20080213518 Oyanagi et al. Sep 2008 A1
20080233362 Kato et al. Sep 2008 A1
20080250970 Oyanagi et al. Oct 2008 A1
20080308004 Deroover et al. Dec 2008 A1
20090053415 Isobe Feb 2009 A1
20090075036 Itano et al. Mar 2009 A1
20090099277 Nagvekar et al. Apr 2009 A1
20090110827 Nakano et al. Apr 2009 A1
20090142555 Sano et al. Jun 2009 A1
20090169834 Sano et al. Jul 2009 A1
20090208651 Oyanagi et al. Aug 2009 A1
20090214833 Oyanagi et al. Aug 2009 A1
20090220695 Oyanagi et al. Sep 2009 A1
20090233064 Yatake et al. Sep 2009 A1
20090246479 Mukai et al. Oct 2009 A1
20090289973 Makuta et al. Nov 2009 A1
20090295847 Mukai et al. Dec 2009 A1
20100009136 Oyanagi et al. Jan 2010 A1
20100086690 Aoki Apr 2010 A1
20100086691 Mukai et al. Apr 2010 A1
20100092674 Mukai et al. Apr 2010 A1
20100092675 Aoki Apr 2010 A1
20110014440 Itano et al. Jan 2011 A1
20110036266 Oyanagi et al. Feb 2011 A1
20110183124 Aoki et al. Jul 2011 A1
20110183125 Aoki et al. Jul 2011 A1
20120006224 Oyanagi et al. Jan 2012 A1
Foreign Referenced Citations (224)
Number Date Country
1086637 Jun 2002 CN
1398724 Feb 2003 CN
1529740 Sep 2004 CN
1721462 Jan 2006 CN
1771307 May 2006 CN
10 2005 021 160 Nov 2006 DE
0 284 561 Sep 1988 EP
0 333 224 Sep 1989 EP
0 352 821 Jan 1990 EP
0 372 778 Jun 1990 EP
0 894 835 Feb 1999 EP
0 997 507 May 2000 EP
1 045 013 Oct 2000 EP
1 260 563 Nov 2002 EP
1 295 916 Mar 2003 EP
1 422 072 May 2004 EP
1 452 569 Sep 2004 EP
1 614 730 Jan 2006 EP
1 616 920 Jan 2006 EP
1 616 921 Jan 2006 EP
1 674 499 Jun 2006 EP
1 752 504 Feb 2007 EP
1 806 387 Jul 2007 EP
1 815 978 Aug 2007 EP
1 837 381 Sep 2007 EP
1 862 511 Dec 2007 EP
1 892 105 Feb 2008 EP
1 942 157 Jul 2008 EP
1 942 158 Jul 2008 EP
1 947 151 Jul 2008 EP
1 950 260 Jul 2008 EP
1 276 369 Jun 1972 GB
1 547 283 Jun 1979 GB
2029433 Mar 1980 GB
2 172 655 Sep 1986 GB
2 367 299 Apr 2002 GB
47-3981 Feb 1972 JP
47-6416 Feb 1972 JP
47-22326 Jun 1972 JP
47-23664 Jul 1972 JP
56-028256 Mar 1981 JP
57-30704 Feb 1982 JP
59-42864 Oct 1984 JP
60-26403 Jun 1985 JP
60-26483 Jun 1985 JP
61-194062 Aug 1986 JP
62-1426 Jan 1987 JP
62-81345 Apr 1987 JP
63-61950 Nov 1988 JP
01-34242 Jul 1989 JP
01-238656 Sep 1989 JP
02-009596 Mar 1990 JP
02-009597 Mar 1990 JP
2-211452 Aug 1990 JP
3-56573 Mar 1991 JP
3-79678 Apr 1991 JP
3-160068 Jul 1991 JP
4-18462 Jan 1992 JP
05-186725 Jul 1993 JP
07-258578 Oct 1995 JP
08-003498 Jan 1996 JP
08-218018 Aug 1996 JP
08-283596 Oct 1996 JP
08-295836 Nov 1996 JP
10-110110 Apr 1998 JP
10-110111 Apr 1998 JP
10-110114 Apr 1998 JP
10-120956 May 1998 JP
10-120958 May 1998 JP
10-195331 Jul 1998 JP
10-195360 Jul 1998 JP
10-237349 Sep 1998 JP
10-287035 Oct 1998 JP
10-330665 Dec 1998 JP
11-011002 Jan 1999 JP
11-165420 Jun 1999 JP
11-193316 Jul 1999 JP
11-202558 Jul 1999 JP
11-343436 Dec 1999 JP
2000-044858 Feb 2000 JP
2000-044861 Feb 2000 JP
2000-336295 Dec 2000 JP
2000-345080 Dec 2000 JP
2000-355667 Dec 2000 JP
2001-348519 Dec 2001 JP
2002-038063 Feb 2002 JP
2007-045990 Feb 2002 JP
2002-179960 Jun 2002 JP
2002-225414 Aug 2002 JP
2002-249165 Sep 2002 JP
2002-256189 Sep 2002 JP
2002-529572 Sep 2002 JP
2002-292775 Oct 2002 JP
2002-332436 Nov 2002 JP
2002-348513 Dec 2002 JP
2003-012971 Jan 2003 JP
2003-55463 Feb 2003 JP
2003-55563 Feb 2003 JP
2003-096337 Apr 2003 JP
2003-253148 Sep 2003 JP
2003-292836 Oct 2003 JP
2003-292857 Oct 2003 JP
2003-292857 Oct 2003 JP
2003-306625 Oct 2003 JP
2003-311945 Nov 2003 JP
2003-342499 Dec 2003 JP
2004-009359 Jan 2004 JP
2004-009360 Jan 2004 JP
2004-018716 Jan 2004 JP
2004-059857 Feb 2004 JP
2004-066817 Mar 2004 JP
2004-099796 Apr 2004 JP
2004-161852 Jun 2004 JP
2004-174971 Jun 2004 JP
2004-195797 Jul 2004 JP
2004-197055 Jul 2004 JP
2004-216654 Aug 2004 JP
2004-250659 Sep 2004 JP
2004-263139 Sep 2004 JP
2004-264435 Sep 2004 JP
2004-535506 Nov 2004 JP
2004-535508 Nov 2004 JP
2004-359960 Dec 2004 JP
2005-007577 Jan 2005 JP
2005-008690 Jan 2005 JP
2005-015813 Jan 2005 JP
2005-023284 Jan 2005 JP
2005-023299 Jan 2005 JP
2005-036079 Feb 2005 JP
2005-060411 Mar 2005 JP
2005-060419 Mar 2005 JP
2005-068250 Mar 2005 JP
2005-068251 Mar 2005 JP
2005-068252 Mar 2005 JP
2005-068439 Mar 2005 JP
2005-096254 Apr 2005 JP
2005-161583 Jun 2005 JP
2005-187659 Jul 2005 JP
2005-220352 Aug 2005 JP
2005-290362 Oct 2005 JP
2005-298757 Oct 2005 JP
2005-314655 Nov 2005 JP
2005-350551 Dec 2005 JP
2005-536375 Dec 2005 JP
2006-070255 Mar 2006 JP
2006-117795 May 2006 JP
2006-117931 May 2006 JP
2006-123529 May 2006 JP
2006-123542 May 2006 JP
2006-176734 Jul 2006 JP
2006-241194 Sep 2006 JP
2006-257302 Sep 2006 JP
2006-257303 Sep 2006 JP
2006-265292 Oct 2006 JP
2006-265524 Oct 2006 JP
2006-272933 Oct 2006 JP
2006-274029 Oct 2006 JP
2006-281538 Oct 2006 JP
2006-281568 Oct 2006 JP
2006-281570 Oct 2006 JP
2006-282822 Oct 2006 JP
2006-282823 Oct 2006 JP
2006-283017 Oct 2006 JP
2006-523762 Oct 2006 JP
2006-312711 Nov 2006 JP
2007-023161 Feb 2007 JP
2007-045989 Feb 2007 JP
2007-046034 Feb 2007 JP
2007-055084 Mar 2007 JP
2007-100053 Apr 2007 JP
2007-100054 Apr 2007 JP
2007-112970 May 2007 JP
2007-131741 May 2007 JP
2007-138084 Jun 2007 JP
2007-154087 Jun 2007 JP
2007-169306 Jul 2007 JP
2007-169307 Jul 2007 JP
2007-169308 Jul 2007 JP
2007-169451 Jul 2007 JP
2007-191613 Aug 2007 JP
2007-211036 Aug 2007 JP
2007-254735 Oct 2007 JP
2007-262272 Oct 2007 JP
2007-269017 Oct 2007 JP
2007-270085 Oct 2007 JP
2007-297586 Nov 2007 JP
2008-075067 Apr 2008 JP
2008-138045 Jun 2008 JP
2008-155523 Jul 2008 JP
2008-155524 Jul 2008 JP
2008-174712 Jul 2008 JP
2009-113494 May 2009 JP
2009-114454 May 2009 JP
2009-242441 Oct 2009 JP
2010-006062 Jan 2010 JP
2010-090270 Apr 2010 JP
2010-090271 Apr 2010 JP
2010-094809 Apr 2010 JP
2010-094852 Apr 2010 JP
9321235 Oct 1993 WO
9905230 Feb 1999 WO
0052530 Sep 2000 WO
0108895 Feb 2001 WO
0238687 May 2002 WO
02055619 Jul 2002 WO
02076764 Oct 2002 WO
2004018197 Mar 2004 WO
2004031308 Apr 2004 WO
2004052947 Jun 2004 WO
2004094534 Nov 2004 WO
2004104051 Dec 2004 WO
2005047405 May 2005 WO
20051061566 Jul 2005 WO
2005089957 Sep 2005 WO
2005095006 Oct 2005 WO
2006041004 Apr 2006 WO
2006085992 Aug 2006 WO
2006087930 Aug 2006 WO
2006098676 Sep 2006 WO
2006-101054 Sep 2006 WO
20061112031 Oct 2006 WO
2007026355 Mar 2007 WO
2007026366 Mar 2007 WO
20071060264 May 2007 WO
Non-Patent Literature Citations (45)
Entry
Patent Abstract of JP 2003-055463.
Patent Abstract of JP 2003-055563.
Monroe, B., et al., “Photoinitiators for Free-Radical-Initiated Photoimaging Systems”, American Chemical Society, Chemical Rev. 93, pp. 435-448, 1993.
Saeva, F. D., et al., Topics in Current Chemistry 156, Photoinduced Electron Transfer (PET) Bond Cleavage Reactions, 1990.
Final Office Action, U.S. Appl. No. 12/228,193, dated Oct. 14, 2011.
Maslak, P., et al., Topics in Current Chemistry, 168, Fragmentations by Photoinduced Electron Transfer Fundamentals and Practical Aspects, 1993.
Chatterjee, S., et al., “Photochemistry of Carbocyanine Alkyltriphenylborate Salts: Intra-Ion-Pair Electron Transfer and the Chemistry of Boranyl Radicals”, J. Am. Chem. Soc., 112, pp. 6329-6338, 1990.
Eaton, D., et al., “One-electron oxidation of benzyltrialkylstannanes. 1. Cation radical fragmentation by dual modes”, J. Am. Chem. Soc., 1980, 102 (9), pp. 3278-3280 Publication Date: Apr. 1980.
Fouassier, J.P., “Photoinitiated Polymerisation—Theory and Applications”, Rapra Review Report, vol. 9, No. 4, 1998.
Final Office Action, U.S. Appl. No. 12/894,423, dated May 29, 2012.
Office Action, U.S. Appl. No. 12/894,423, dated Nov. 10, 2011.
Office Action, JP2007-304874 dated May 25, 2011, English Translation.
Office Action, U.S. Appl. No. 12/394,336, dated Apr. 26, 2012.
Ciba® IRGACURE® 369 Photoinitiator, Ciba Specialty Chemicals Coating Effects Segment, Edition 4.9.2001.
CIBA®, ®Ciba Secialty Chemicals, “Ciba® IRGASTAB® UV 22”, Coating Effects, 2006.
EP Search Report for Application No. 11152226.4, dated May 11, 2005.
The Japanese Research Association for Organic Materials for Imaging, Bunshin Publishing co., pp. 187-192, 1993.
Notice of Allowance, U.S. Appl. No. 12/228,224 dated Oct. 20, 2011.
Office Action, U.S. Appl. No. 12/228,224, dated Jun. 2, 2011.
Supplemental Notice of Allowance, U.S. Appl. No. 12/228,224, dated Jun. 28, 2012.
Step, E.N., et al., “Mechanism of Polymer Stabilization by Hindered-Amine Light Stabilizers (HALS). Model Investigations of the Interaction of Peroxy Radicals with HALS Amines and Amino Ethers”, Macromolecules, American Chemical Society, 27, pp. 2529-2539, 1994.
LAROMER® UA 9029 V, Technical Information Sheet, BASF, Dec. 2003.
Ciba® IRGACURE 127 Photoinitiator, Technical Data Sheet from Ciba Specialty Chemicals, 2004.
Ciba® IRGACURE 819 Photoinitiator, Technical Data Sheet from Ciba Specialty Chemicals, 2004.
Ciba® DAROCUR EDB, Photoinitiator, Ciba Specialty Chemicals Coating Effects, product technical disclosure, Feb. 20, 2003.
Kim, Y., “Highly Branched Aromatic Polymers Prepared by Single Step Syntheses”, Macromol. Symp. pp. 21-33, 1994.
Hawker, C., et al., “Hyperbranched Poly(ethylene glycol)s: A New Class of Ion-Conducting Materials”, Macromolecules, vol. 29, pp. 3831-3838, 1996.
European Search Report, EP07024545.1 dated Apr. 21, 2008.
Office Action, U.S. Appl. No. 13/240,667 dated Dec. 12, 2011.
EP Search Report, Application No. 11177753.8, dated Nov. 2, 2011.
Final Office Action, U.S. Appl. No. 12/074,308 dated Jun. 8, 2012.
Office Action, CN Application No. 200910004654.0, dated Nov. 30, 2010, with English Translation.
Office Action, JP Application No. 2007-316368, dated Mar. 9, 2011, with English Translation.
Office Action, U.S. Appl. No. 12/074,308, dated Dec. 21, 2011.
Office Action, U.S. Appl. No. 13/197,174, dated Jan. 6, 2012.
Dispersion definition from Hawley's Condensed Chemical Dictionary.
Dispersion (chemistry) Wikipedia Definition, Wikipedia the free encyclopedia, Oct. 25, 2010.
Shiraj, M., et al, “Photoacid and Photobase Generators: Chemistry and Applications to Polymeric Materials”, Prog. Polm. Sci., vol. 21, No. 1, 1996.
Office Action, U.S. Appl. No. 12/228,193 dated Jun. 2, 2011.
Office Action, U.S. Appl. No. 12/228,193, dated Mar. 8, 2012.
Davidson, R.S., “The chemistry of photoinitiators—some recent developments”, J. Photochem: Photobiol., A: Chem, 73. pp. 81-96, 1993.
Fouassier, J.P., et al., Radiation Curing in Polymer Science and Technology, vol. 1, fundamentals and methods, pp. 77-117, 1993.
EP Search Report for Application No. 08016440.3, dated Dec. 29, 2008.
Search Report for PCT/JP20081064126 dated Sep. 16, 2008.
Hawker, C., et al., “Preparation of Polymers with Controlled Molecular Architecture. A New Convergent Approach to Dendritic Macromolecules”, Journal of American Chemistry Society, 1990, 112, pp. 7638-7647.
Related Publications (1)
Number Date Country
20090318580 A1 Dec 2009 US