National University Corporation YOKOHAMA National University (Japan)
Inventor
Himori, Shunichi
Iuchi, Keita
Yamada, Akihiko
Gotoh, Hiroaki
Sakakibara, Kazuhisa
Abstract
A radical polymerization method may use a compound having a polycyclic aromatic skeleton and an endoperoxide compound having a polycyclic aromatic skeleton. An endoperoxide compound may have a polycyclic aromatic skeleton of formula (1), and a compound may have a polycyclic aromatic skeleton, which is a raw material of the endoperoxide compound:
6-12 aryl group.
A photopolymerization sensitizer may not cause problems of dusting or coloring of a cured product due to bleeding of additives such as the photopolymerization sensitizer on the surface, e.g., by blooming at the time of photo-curing or during storage of the cured product, and which provides a practically sufficient photo-curing rate. A 9,10-bis(alkoxycarbonylalkyleneoxy)anthracene compound having ester groups, of formula (I):
1-8 alkyl group, or a halogen.
C07C 69/736 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
C07C 67/10 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
C07C 67/26 - Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
C07C 67/343 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton by increase in the number of carbon atoms
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
[Problem] The problem of the present invention is to provide an environmentally friendly photoradical polymerization initiator that does not generate acids inducing corrosion during radical polymerization reaction and consists of carbon atoms, hydrogen atoms, and oxygen atoms, the photoradical polymerization initiator having high radical polymerization initiating performance to light in the wavelength range of 350-420 nm. [Solution] Provided is a photoradically polymerizable composition comprising a radically polymerizable compound and a photoradical polymerization initiator. The photoradically polymerizable composition is characterized in that the photoradical polymerization initiator contains the 1,4-dihydroxy-2-naphthoate compound represented by the following general formula (1). In general formula (1), R represents a hydrogen atom, an alkyl group having 1-10 carbon atoms, or an aryl group having 6-14 carbon atoms; and X represents a hydrogen atom, an alkyl group having 1-10 carbon atoms, an aryl group having 6-14 carbon atoms, a hydroxy group, an alkoxy group having 1-10 carbon atoms, or an aryloxy group having 6-14 carbon atoms.
A conventional polymerization inhibitor is for example an agent to scavenge radicals generated during storage of a radical polymerizable compound and used to stably handle the radical polymerizable compound, but is unnecessary when the radical polymerizable compound is to be subjected to radical polymerization reaction, and is preferably removed at the time of the radical polymerization reaction. The object of the present invention is to obviate inconvenience of removing the polymerization inhibitor at the time of radical polymerization.
The radical polymerization control agent contained in a radical polymerizable composition of the present invention functions as a radical polymerization inhibitor for example stored in a dark place, but loses its radical polymerization inhibiting effect when polymerization is initiated while being irradiated with light at a certain specific wavelength at the time of polymerization. Thus, radical polymerization of the radical polymerizable compound is easily initiated without increasing the amount of a radical polymerization initiator. That is, the radical polymerization control agent of the present invention is a radical polymerization control agent which is a corn pound having an effect to inhibit radical polymerization of a radical polymerizable compound and which loses the radical polymerization inhibiting effect under irradiation with light rays containing light within a wavelength range of from 300 nm to 500 nm.
C07C 43/23 - Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
C07C 43/20 - Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
C07C 50/32 - Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
C07C 255/65 - Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
C08F 2/40 - Polymerisation using regulators, e.g. chain terminating agents using retarding agents
C08F 2/48 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
The purpose of the present invention is to provide a photopolymerizable composition which can act as a photopolymerization sensitizer that is active against light having a wavelength falling within a wavelength range of from 300 to 500 nm, and which has such a property that coloring of a cured product produced by polymerizing a photopolymerizable composition containing the photopolymerization sensitizer is less.
A photopolymerization sensitizer composition characterized by comprising a photopolymerization sensitizer containing an alkoxyanthracene compound represented by the formula (1) and a singlet oxygen quencher; and a photopolymerizable composition containing the photopolymerization sensitizer composition:
1-8 alkyl group.
[Problem] To provide a coating composition wherein a photoradical composition using a photoradical polymerization initiator that is markedly affected by oxygen inhibition can be cured without problems even in the presence of oxygen through a reduction in oxygen inhibition on the coating surface. [Solution] A photoradical polymerizable composition characterized by containing at least a radical polymerizable compound, a photoradical polymerization initiator, and a 9,10-bis(alkoxycarbonylalkyleneoxy)anthracene compound having an ester group and represented by general formula (1). (In general formula (1), A represents a C1-20 alkylene group that may be branched by an alkyl group, and R represents a C1-20 alkyl group.)
[Problem] The purpose of the present invention is to provide a coating composition in which oxygen inhibition at the surface of a coating can be reduced for a photoradical composition that uses a radical photopolymerization initiator which is prominently affected by oxygen inhibition, and said coating composition being curable without any problems, even in the presence of oxygen. [Solution] A radical photopolymerizable composition characterized by containing at least a radical polymerizable compound, a radical photopolymerization initiator, and a 9,10-bis(alkoxycarbonylalkyleneoxy)anthracene compound comprising an ester group represented by general formula (1). (In general formula (1), A represents a C1–C20 alkylene group optionally branched by an alkyl group. R represents a C1–C20 alkyl group that is optionally branched by an alkyl group, is optionally a cycloalkyl group, or is optionally substituted with a hydroxy group, and in which some of the carbon atoms are optionally substituted with oxygen atoms.)
C08F 299/08 - Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
8.
PHOTO-RADICALLY CURABLE OXYGEN-INHIBITION-REDUCING AGENT, PHOTO-RADICALLY CURABLE OXYGEN-INHIBITION-REDUCING AGENT-CONTAINING PHOTO-RADICALLY POLYMERIZABLE COMPOSITION, PHOTO-RADICALLY CURABLE OXYGEN-INHIBITION-REDUCING AGENT-CONTAINING COATING FILM, AND METHOD FOR CURING SAME
[Problem] The objective of the present invention is to provide a coating film composition capable of curing a photo-radical composition using a photoradical polymerization initiator, which is significantly affected by oxygen inhibition , without any problem even in the presence of oxygen by reducing oxygen inhibition on the surface of the coating film. [Solution] This photo-radically polymerizable composition is characterized by containing at least a radically polymerizable compound, a photoradical polymerization initiator, and a 9,10-bis(alkoxycarbonylalkyleneoxy)anthracene compound having an ester group represented by general formula (1). (In general formula (1), A represents an alkylene group having 1-20 carbon atoms, and the alkylene group may be branched by an alkyl group. R represents an alkyl group having 1-20 carbon atoms.)
C08L 101/02 - Compositions of unspecified macromolecular compounds characterised by the presence of specified groups
C09D 4/00 - Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond
9.
PHOTOPOLYMERIZATION SENSITIZER HAVING MIGRATION RESISTANCE
[Problem] To provide a photopolymerization sensitizer that enables sufficient photocuring speed in practice, without blooming or the like during photocuring or storage of a cured product causing additives in the photopolymerization sensitizer or the like to bleed into the surface and create problems such as coloring or chalking of the cured product. [Solution] A 9,10-bis(alkoxycarbonylalkyleneoxy)anthracene compound having an ester group represented by general formula (1). (In general formula (1), A represents a C1-20 alkylene group, and the alkylene group may be branched by an alkyl group. R represents a C1-20 alkyl group, and the alkyl group may be branched by an alkyl group, may be substituted with a hydroxy group, and some of the carbon atoms may be replaced with oxygen atoms (except when forming a peroxide). X and Y may be the same or different, and individually represent a hydrogen atom, a C1-8 alkyl group, or a halogen atom.)
C07C 69/736 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
C07C 67/10 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
C07C 67/26 - Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
C07C 67/343 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton by increase in the number of carbon atoms
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
[Problem] To provide a photopolymerization sensitizer which imparts sufficient photocuring speed for practical purposes without causing the problem of coloring or powder blowing in cured products due to additives such as the photopolymerization sensitizer bleeding to the surface as a result of blooming or the like when photocuring or during storage of cured products. [Solution] A 9,10-bis(alkoxy carbonyl alkylene oxy)anthracene compound represented by general formula (1) and having an ester group. (In general formula (1), A represents a C1-20 alkylene group, and said alkylene group may be branched by an alkyl group. R represents a C1-20 alkyl group, and said alkyl group may be branched by an alkyl group and may be a cycloalkyl group or a cycloalkyl alkyl group. X and Y may be the same or different, and each represent a C1-8 alkyl group or a halogen atom.
C07C 69/736 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/08 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
C07C 67/10 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
C07C 67/26 - Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
C07C 67/343 - Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisationPreparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by change of size of the carbon skeleton by increase in the number of carbon atoms
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
[Problem] To provide a photopolymerization sensitizer which exhibits sufficient photocuring speed during practical use, without causing problems such as staining or powder on the cured article or the appearance of an additive such as the photopolymerization sensitizer on the surface thereof due to blooming or the like at the time of photocuring or during storage of the cured article. [Solution] An oligomer of: a 9,10-bis (alkoxycarbonyl alkyleneoxy) anthracene compound which has an ester group and is represented by general formula (1), or a 9,10-bis (alkoxycarbonyl alkyleneoxy) anthracene compound which has an ester group and is represented by general formula (10). (In the general formulas, A represents a C1-20 alkylene group, and the alkylene group may be bifurcated by an alkyl group.)
C07C 69/712 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/11 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
[Problem] To provide a photopolymerization sensitizer which exhibits sufficient photocuring speed during practical use, without causing problems such as staining or powder on the cured article or the appearance of an additive such as the photopolymerization sensitizer on the surface thereof due to blooming or the like at the time of photocuring or during storage of the cured article. [Solution] An oligomer of: a 9,10-bis (alkoxycarbonyl alkyleneoxy) anthracene compound which has an ester group and is represented by general formula (1), or a 9,10-bis (alkoxycarbonyl alkyleneoxy) anthracene compound which has an ester group and is represented by general formula (10). (In the general formulas, A represents a C1-20 alkylene group, and the alkylene group may be bifurcated by an alkyl group.)
C07C 69/712 - Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/11 - Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 59/20 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the epoxy compounds used
To provide a photopolymerization sensitizer which will not cause problems of dusting or coloring of a cured product by bleeding of additives such as the photopolymerization sensitizer on the surface e.g. by blooming at the time of photo-curing or during storage of the cured product, and which imparts a practically sufficient photo-curing rate.
An oligomer of a 9,10-bis(substituted oxy)anthracene compound having repeating units represented by the following formula (1):
1-8 alkyl group or a halogen atom, and A is a bivalent substituent.
C07C 271/52 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
C07C 271/56 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
C07C 271/58 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
C08F 220/30 - Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
C08G 59/06 - Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
C08G 63/197 - Hydroxy compounds containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
[Problem] The purpose of the present invention is to provide a photopolymerizable composition which can act as a photopolymerization sensitizer that is active against light having a wavelength falling within the wavelength range from 300 to 500 nm, and which has such a property that a cured article produced by polymerizing a photopolymerizable composition containing the photopolymerization sensitizer is rarely discolored. [Solution] A photopolymerization sensitizer composition which is characterized by comprising a photopolymerization sensitizer comprising an alkoxyanthracene compound represented by general formula (1) and a singlet oxygen quencher; and a photopolymerizable composition which contains the photopolymerization sensitizer composition. (In general formula (1), n represents an integer of 1 or 2; R represents an alkyl group having 1 to 12 carbon atoms; and X represents any one of a hydrogen atom and an alkyl group having 1 to 8 carbon atoms.)
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
NATIONAL UNIVERSITY CORPORATION YOKOHAMA NATIONAL UNIVERSITY (Japan)
Inventor
Himori Shunichi
Iuchi, Keita
Yamada, Akihiko
Gotoh,hiroaki
Sakakibara,kazuhisa
Abstract
[Problem] To provide a novel radical polymerization method using a compound having a polycyclic aromatic skeleton and an endoperoxide compound having a polycyclic aromatic skeleton. [Solution] An endoperoxide compound having a polycyclic aromatic skeleton represented by general formula (1); and a compound having a polycyclic aromatic skeleton, which is a raw material of the endoperoxide compound. (In general formula (1), R denotes an alkyl group having 1-10 carbon atoms, an alkoxymethyl group having an alkoxy group with 1-5 carbon atoms, an aryl group having 6-10 carbon atoms, an alkylcarbonyl group having an alkyl group with 1-10 carbon atoms, an arylcarbonyl group having an aryl group with 6-20 carbon atoms, an alkyloxycarbonyl group having an alkyl group with 1-10 carbon atoms, an aryloxycarbonyl group having an aryl group with 6-10 carbon atoms, an alkyloxycarbonylmethyl group having an alkyl group with 1-12 carbon atoms, or an aryloxycarbonylmethyl group having an aryl group with 6-12 carbon atoms.)
{Problem] To provide a photoradically polymerizable composition that can be radically polymerized easily without being affected by oxygen inhibition, and a method for radical polymerization. [Solution] A photoradically polymerizable composition that is photoradically polymerized by irradiating with light having a peak wavelength in a specific wavelength range in a situation in which the surface of the photoradically polymerizable composition is in contact with air, wherein the photoradically polymerizable composition contains a radically polymerizable compound, a photoradical polymerization initiator represented by general formula (1), and an onium salt photopolymerization initiator. (R1and R2 each represent a C1-20 alkyl group, a C6-20 aryl group, an alkylcarbonyl group having a C1-20 alkyl group, an arylcarbonyl group having a C6-20 aryl group, an alkyloxycarbonyl group having a C1-20 alkyl group, or an aryloxycarbonyl group having a C6-20 aryl group.)
[Problem] To provide a radically polymerizable composition which is able to be radically polymerized easily without causing oxygen inhibition even if oxygen is present in the system during a polymerization reaction of a radically polymerizable compound; and a radical polymerization method. [Solution] A radically polymerizable composition which is polymerized by being irradiated with light that includes a specific wavelength range in the presence of oxygen, and which contains, as a radical photopolymerization initiator, an anthracene compound that is represented by general formula (1). (In general formula (1), each of R1and R2represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylcarbonyl group that has an alkyl group having 1 to 20 carbon atoms, an arylcarbonyl group that has an aryl group having 6 to 20 carbon atoms, an alkyloxycarbonyl group that has an alkyl group having 1 to 20 carbon atoms or an aryloxycarbonyl group that has an aryl group having 6 to 20 carbon atoms; and R1and R2 may be the same as or different from each other.)
[Problem] Conventional polymerization inhibitors are used to capture radicals generated, for example, during storage of a radical polymerizable compound, thus allowing the radical polymerizable compound to be safely handled. However, the polymerization inhibitors constitute unnecessary additives when radical polymerization of the radical polymerizable compound is actually being effected, and are preferably removed before the radical polymerization. The purpose of the present invention is to eliminate this inconvenient removal step. [Solution] This radical polymerization control agent is contained in a radical polymerizable composition, and serves as a radical polymerization inhibitor when, for example, stored in darkness. When polymerization is initiated under irradiation with light of a specific wavelength, the radical polymerization control agent loses the radical polymerization inhibitory effect. This makes it possible to easily initiate polymerization of a radical polymerizable compound without increasing the amount of a radical polymerization initiator. Namely, the radical polymerization control agent is a compound effective in inhibiting radical polymerization of a radical polymerizable compound and characterized by losing the radical polymerization inhibitory effect under irradiation with beams including light within the wavelength range of 300 nm to 500 nm.
C08F 2/40 - Polymerisation using regulators, e.g. chain terminating agents using retarding agents
C08F 2/46 - Polymerisation initiated by wave energy or particle radiation
C08F 20/00 - Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide, or nitrile thereof
C07C 43/20 - Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
C07C 43/23 - Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
C07C 50/32 - Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
[Problem] To provide a photopolymerization sensitizer which gives a practically sufficient photocuring rate without arousing the problem wherein additives including a photopolymerization sensitizer bleed out to the surface during photocuring or during storage of the cured object to cause blooming or coloration to the cured object. [Solution] An oligomer of a 9,10-bis(substituted oxy)anthracene compound, the oligomer having repeating units represented by general formula (1). (In general formula (1), n, indicating the number of repetitions, is 2-50; X and Y may be the same or different and each represent a hydrogen atom, a C1-8 alkyl group, or a halogen atom; and A represents a divalent substituent.)
C07C 269/02 - Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
C07C 271/44 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
C07C 271/56 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
C07C 271/58 - Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
C08G 59/06 - Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
C08G 63/197 - Hydroxy compounds containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
C08G 65/38 - Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
To provide a photopolymerizable composition which can be quickly cured by light of from 300 nm to 500 nm, and a cured product of which is less colored.
A photopolymerizable composition comprising a compound having an anthracene skeleton represented by the following formula (1), a compound having a benzophenone skeleton and a radical polymerizable compound:
1-8 alkyl group.
[Problem] To provide a UV-A absorbent and a UV-A blocking film, each of which has an excellent UV-A blocking function capable of blocking light rays ranging from the near ultraviolet region to blue. [Solution] A UV-A absorbent which is characterized by being an anthracene compound represented by general formula (1). (In general formula (1) and general formula (2), R1 and R2 may be the same or different, and each represents an alkyl group having 1-12 carbon atoms, an aryl group having 6-13 carbon atoms, an alkoxy group having 1-12 carbon atoms or an aryloxy group having 6-13 carbon atoms; and X and Y may be the same or different, and each represents an alkyl group having 1-8 carbon atoms or a halogen atom.)
C07C 69/28 - Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
C07C 69/96 - Esters of carbonic or haloformic acids
23.
PHOTOPOLYMERIZATION SENSITIZER COMPOSITION AND PHOTOPOLYMERIZABLE COMPOSITION CONTAINING SAME
[Problem] To provide a photopolymerizable composition which is able to be quickly cured by means of light of from 300 nm to 500 nm, and which provides a cured product that is less colored. [Solution] A photopolymerization sensitizer composition which contains an anthracene compound (A) represented by general formula (1) and an anthracene compound (B) represented by general formula (2). (In general formula (1), R1 represents an alkyl group having 1-20 carbon atoms, an aryl group having 6-20 carbon atoms, an alkoxy group having 1-20 carbon atoms or an aryloxy group having 6-20 carbon atoms.) (In general formula (2), R2 represents a hydrogen atom, an alkyl group having 1-8 carbon atoms, an alkoxymethyl group that has an alkoxy group having 1-5 carbon atoms, an allyloxymethyl group or an aryloxymethyl group that has an aryl group having 6-10 carbon atoms.)
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08F 20/00 - Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide, or nitrile thereof
24.
PHOTOPOLYMERIZATION SENSITIZER COMPOSITION AND PHOTOPOLYMERIZABLE COMPOSITION COMPRISING SAME
[Problem] To provide a photopolymerizable composition which can be quickly cured by light of wavelength of 300-450 nm and a cured product of which is less colored. [Solution] A photopolymerization sensitizer composition which comprises a compound represented by general formula (1) and a compound the maximum absorptivity of which in the absorption within the wavelength range of 400-500 nm is larger than the maximum absorptivity of the aforesaid compound in the absorption within the wavelength range of 400-500 nm; and a photopolymerizable composition comprising the photopolymerization sensitizer composition. [In general formula (1): R represents an alkyl group having 1-20 carbon atoms, an aryl group having 6-20 carbon atoms, an alkoxy group having 1-20 carbon atoms or an aryloxy group having 6-20 carbon atoms; and X and Y may be the same or different and represent a hydrogen atom or an alkyl group having 1-8 carbon atoms.]
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C08G 65/04 - Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
[Problem] To provide a photopolymerizable composition, wherein rapid curing by 300 nm to 500 nm light is possible, and there is no coloration of the cured product. [Solution] A photopolymerizable composition including a compound having an anthracene skeleton represented by general formula (1), a compound having a benzophenone skeleton, and a radical polymerizable compound. (In general formula (1), R1 and R2 each represent a C1-20 alkyl group, a C6-20 aryl group, an alkylcarbonyl group having a C1-20 alkyl group, an arylcarbonyl group having a C6-20 aryl group, an alkyloxycarbonyl group having a C1-20 alkyl group, or an aryloxycarbonyl group having a C6-20 aryl group, and R1 and R2 may be the same or different. In general formula (1), X and Y represent a hydrogen atom or a C1-8 alkyl group, and X and Y may be the same or different.)
[Problem] To provide a photopolymerization sensitizer which is active with respect to an energy ray including light having a wavelength from 355 nm to 420 nm, and which is not susceptible to migration. [Solution] A photopolymerization sensitizer which contains an anthracene compound represented by general formula (1). In general formula (1), R represents an alkyl group having 1-12 carbon atoms, an aryl group having 6-12 carbon atoms, an alkoxy group having 1-8 carbon atoms or an allyloxy group; and X and Y may be the same or different and each represents a hydrogen atom or an alkyl group having 1-8 carbon atoms.
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C07C 69/16 - Acetic acid esters of dihydroxylic compounds
C07C 69/28 - Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
C07C 69/96 - Esters of carbonic or haloformic acids
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The object is to produce a molded article having an improved heat resistance by the crystallization of a polylactic acid resin using a conventional crystal nucleating agent at a low cost, thereby producing an molded article having improved heat resistance and impact resistance. Disclosed is a polylactic acid resin composition comprising at least a polylactic acid resin, a polyester polyol and a crystal nucleating agent, wherein the polyester polyol is a product of the esterification reaction between at least one carboxylic acid selected from succinic acid, glutaric acid and adipic acid and one or two alcohols selected from diethylene glycol and triethylene glycol, and wherein the polyester polyol and the crystal nucleating agent are contained in amounts of 0.1 to 20 parts by weight and 0.1 to 50 parts by weight, respectively, relative to 100 parts by weight of the polylactic acid resin.
Disclosed is a radical photopolymerization initiator useful for polymerization of a radically polymerizable monomer. Also disclosed is a method for curing a photocurable composition wherein a radically polymerizable monomer is cured by being irradiated with near-visible ultraviolet light while using such a radical photopolymerization initiator. Specifically disclosed is a novel radical photopolymerization initiator containing an onium salt such as a specific sulfonium salt and an anthracene-9,10-diether compound. Also specifically disclosed is a photocurable composition containing such a radical photopolymerization initiator and a radically polymerizable monomer. This photocurable composition is excellent in adhesion, and is cured by being irradiated with near-visible ultraviolet light preferably having a wavelength range of 380-420 nm.
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
An industrially advantageous process is presented whereby a high purity anthracene diether can be produced in good yield.
An aqueous medium containing an alkali salt of 9,10-anthracenediol is added to an organic solvent containing an etherifying agent in the presence or absence of a quaternary ammonium compound or a quaternary phosphonium compound, to carry out the etherifying reaction to produce the anthracene diether.
01 - Chemical and biological materials for industrial, scientific and agricultural use
Goods & Services
Industrial chemicals for use in the manufacture of lacquers, printing inks and synthetic resins that are cured with ultra-violet light; chemical reagents for scientific or research use; all of the aforementioned goods being not for medical or veterinary purposes
