JP2008303260A5 - - Google Patents

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JP2008303260A5
JP2008303260A5 JP2007149993A JP2007149993A JP2008303260A5 JP 2008303260 A5 JP2008303260 A5 JP 2008303260A5 JP 2007149993 A JP2007149993 A JP 2007149993A JP 2007149993 A JP2007149993 A JP 2007149993A JP 2008303260 A5 JP2008303260 A5 JP 2008303260A5
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式（１）、（２）、または（３）で表される化合物。

Figure 2008303260

Figure 2008303260

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（式中、Ｒ１は水素、またはメチルであり、Ｒ２は炭素数２〜２０のアルキレンであり、Ｒ3はメチレンであり、Ｒ4およびＲ5は独立して、炭素数１〜２０のアルキル、フェニル、任意の水素が炭素数１〜５のアルキルで置き換えられたフェニル、または任意の水素がフェニルで置き換えられたフェニルであり、Ｒ4とＲ5が一体となって環状基を形成してもよく、ｍは１〜３０の整数であり、ｎ、ｐおよびｑは独立して、０または１である。）
A compound represented by formula (1), (2), or (3).

Figure 2008303260

Figure 2008303260

Figure 2008303260

Wherein R 1 is hydrogen or methyl, R 2 is alkylene having 2 to 20 carbon atoms, R 3 is methylene, and R 4 and R 5 are independently 1 to 20 carbon atoms. Alkyl, phenyl, phenyl in which arbitrary hydrogen is replaced with alkyl having 1 to 5 carbon atoms, or phenyl in which arbitrary hydrogen is replaced with phenyl, and R 4 and R 5 are combined to form a cyclic group. M is an integer of 1 to 30, and n, p and q are independently 0 or 1.)
式（４）、（５）、または（６）で表される化合物。

Figure 2008303260

Figure 2008303260

Figure 2008303260

（式中、Ｒ１は水素、またはメチルであり、Ｒ２は炭素数２〜２０のアルキレンであり、Ｒ3はメチレンであり、ｍは１〜３０の整数であり、ｎは０または１である。） The compound represented by Formula (4), (5), or (6).

Figure 2008303260

Figure 2008303260

Figure 2008303260

Wherein R 1 is hydrogen or methyl, R 2 is alkylene having 2 to 20 carbon atoms, R 3 is methylene, m is an integer of 1 to 30, and n is 0 or 1. is there.) 請求項１または２に記載の化合物から選ばれる難燃剤（Ａ）を２０〜１００重量％含有するラジカル重合性モノマーの混合物を重合して得られる難燃性重合体（Ｆ）。   A flame retardant polymer (F) obtained by polymerizing a mixture of radical polymerizable monomers containing 20 to 100% by weight of a flame retardant (A) selected from the compound according to claim 1 or 2. 請求項１または２に記載の化合物から選ばれる難燃剤（Ａ）および請求項３に記載の難燃性重合体（Ｆ）から選ばれる１つ以上と、オキシランまたはオキセタンを２つ以上有する化合物（Ｂ）を含有する熱硬化性組成物   One or more selected from the flame retardant (A) selected from the compound according to claim 1 or 2 and the flame retardant polymer (F) according to claim 3, and a compound having two or more oxiranes or oxetanes ( Thermosetting composition containing B) インクジェット用インクである、請求項４に記載の熱硬化性組成物。   The thermosetting composition according to claim 4, which is an inkjet ink. スクリーン印刷用インクである、請求項４に記載の熱硬化性組成物。   The thermosetting composition according to claim 4, which is a screen printing ink. 請求項１または２に記載の化合物から選ばれる難燃剤（Ａ）および請求項３に記載の難燃性重合体（Ｆ）から選ばれる１つ以上と、（メタ）アクリレート（Ｃ）、光重合開始剤（Ｄ）を含有する光硬化性組成物。   One or more selected from the flame retardant (A) selected from the compound according to claim 1 or 2 and the flame retardant polymer (F) according to claim 3, and (meth) acrylate (C), photopolymerization A photocurable composition containing an initiator (D). インクジェット用インクである、請求項７に記載の光硬化性組成物。   The photocurable composition according to claim 7, which is an inkjet ink. スクリーン印刷用インクである、請求項７に記載の光硬化性組成物。   The photocurable composition according to claim 7, which is a screen printing ink. オキシランまたはオキセタンを２つ以上有する化合物（Ｂ）が式（７）、（８）、（９）、または（１０）である、請求項４〜６のいずれか一項に記載の熱硬化性組成物。

Figure 2008303260

（式（７）中、ｎは０〜１０の整数である。） The thermosetting composition according to any one of claims 4 to 6, wherein the compound (B) having two or more oxiranes or oxetanes is a formula (7), (8), (9), or (10). object.

Figure 2008303260

(In Formula (7), n is an integer of 0-10.) （メタ）アクリレート（Ｃ）が式（１１）、（１２）、（１３）および（１４）から選ばれる１つ以上である、請求項７〜９のいずれか一項に記載の光硬化性組成物。

Figure 2008303260

（式（１１）中、ａ、ｂ、ｃはそれぞれ独立に０〜１０の整数であり、Ｒ６のうちｒ個は式（１１−１）で表される基であり、ｓ個は式（１１−２）で表される基であり、ｒは０〜２の整数であり、ｓは１〜３の整数であり、ｒ＋ｓは３であり、Ｒ1は水素またはメチルである）

Figure 2008303260

（式（１２）中、ａ、ｂ、ｃはそれぞれ独立に０〜１０の整数であり、Ｒ７のうちｒ個は式（１２−１）で表される基であり、ｓ個は式（１２−２）で表される基であり、ｒは０〜２の整数であり、ｓは１〜３の整数であり、ｒ＋ｓは３であり、Ｒ1は水素またはメチルである）

Figure 2008303260

（式（１３）中、ａ、ｂ、ｃ、ｄはそれぞれ独立に０〜１０の整数であり、Ｒ８のうちｒ個は式（１３−１）で表される基であり、ｓ個は式（１３−２）で表される基であり、ｒは０〜３の整数であり、ｓは１〜４の整数であり、ｒ＋ｓは４であり、Ｒ1は水素またはメチルである）

Figure 2008303260

（式（１４）中、ａ、ｂ、ｃ、ｄ、ｅ、ｆはそれぞれ独立に０〜１０の整数であり、Ｒ９のうちｒ個は式（１４−１）で表される基であり、ｓ個は式（１４−２）で表される基であり、ｒは０〜５の整数であり、ｓは１〜６の整数であり、ｒ＋ｓは６であり、Ｒ1は水素またはメチルである） The photocurable composition according to any one of claims 7 to 9, wherein the (meth) acrylate (C) is one or more selected from the formulas (11), (12), (13) and (14). object.

Figure 2008303260

(In the formula (11), a, b and c are each independently an integer of 0 to 10, r out of R 6 is a group represented by the formula (11-1), and s is a formula (11). 11-2), r is an integer of 0 to 2, s is an integer of 1 to 3, r + s is 3, and R 1 is hydrogen or methyl)

Figure 2008303260

(In the formula (12), a, b and c are each independently an integer of 0 to 10, r of R 7 is a group represented by the formula (12-1), and s is a formula (12). 12-2), r is an integer of 0 to 2, s is an integer of 1 to 3, r + s is 3, and R 1 is hydrogen or methyl)

Figure 2008303260

(In the formula (13), a, b, c and d are each independently an integer of 0 to 10, and r out of R 8 is a group represented by the formula (13-1), and s is A group represented by formula (13-2), r is an integer of 0 to 3, s is an integer of 1 to 4, r + s is 4, and R 1 is hydrogen or methyl)

Figure 2008303260

(In Formula (14), a, b, c, d, e, and f are each independently an integer of 0 to 10, and r of R 9 is a group represented by Formula (14-1). , S is a group represented by formula (14-2), r is an integer of 0 to 5, s is an integer of 1 to 6, r + s is 6, and R 1 is hydrogen or methyl. Is) さらに（メタ）アクリレート（Ｃ）を含有する、請求項４〜６、１０のいずれか一項に記載の熱硬化性組成物。   The thermosetting composition according to any one of claims 4 to 6, further comprising (meth) acrylate (C). （メタ）アクリレート（Ｃ）が式（１５）の化合物である、請求項７〜９のいずれか一項に記載の光硬化性組成物。

Figure 2008303260

（式（１５）中、Ｒ6は環状構造を有してよい炭素数２〜１２のアルキレンであり、Ｒ1は水素またはメチルであり、ｔは１〜３０の整数である。） The photocurable composition as described in any one of Claims 7-9 whose (meth) acrylate (C) is a compound of Formula (15) .

Figure 2008303260

(In Formula (15), R 6 is alkylene having 2 to 12 carbon atoms which may have a cyclic structure, R 1 is hydrogen or methyl, and t is an integer of 1 to 30.) （メタ）アクリレート（Ｃ）が式（１５）の化合物である、請求項１２に記載の熱硬化性組成物。

Figure 2008303260

（式（１５）中、Ｒ 6 は環状構造を有してよい炭素数２〜１２のアルキレンであり、Ｒ 1 は水素またはメチルであり、ｔは１〜３０の整数である。） The thermosetting composition of Claim 12 whose (meth) acrylate (C) is a compound of Formula (15).

Figure 2008303260

(In Formula (15), R 6 is alkylene having 2 to 12 carbon atoms which may have a cyclic structure, R 1 is hydrogen or methyl, and t is an integer of 1 to 30.) （メタ）アクリレート（Ｃ）が式（１１）〜（１４）から選ばれる１つ以上と式（１５）の化合物の混合物である、請求項７〜９のいずれか一項に記載の光硬化性組成物。  The photocurable property according to any one of claims 7 to 9, wherein the (meth) acrylate (C) is a mixture of one or more selected from the formulas (11) to (14) and the compound of the formula (15). Composition. （メタ）アクリレート（Ｃ）が式（１１）〜（１４）から選ばれる１つ以上と式（１５）の化合物の混合物である、請求項１２に記載の熱硬化性組成物。  The thermosetting composition according to claim 12, wherein the (meth) acrylate (C) is a mixture of one or more selected from the formulas (11) to (14) and the compound of the formula (15). 式（１５）の化合物が、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、および１，４−シクロヘキサンジメタノールモノ（メタ）アクリレートからなる群から選ばれる１以上である、請求項１３または１５に記載の光硬化性組成物。  The compound of formula (15) consists of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 1,4-cyclohexanedimethanol mono (meth) acrylate. The photocurable composition according to claim 13 or 15, which is one or more selected from the group. 式（１５）の化合物が、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、および１，４−シクロヘキサンジメタノールモノ（メタ）アクリレートからなる群から選ばれる１以上である、請求項１４または１６に記載の熱硬化性組成物。  The compound of formula (15) consists of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 1,4-cyclohexanedimethanol mono (meth) acrylate. The thermosetting composition according to claim 14 or 16, which is one or more selected from the group. 光重合開始剤（Ｄ）がビス（２，４，６−トリメチルベンゾイル）フェニルフォスフィンオキサイド、または２，４，６−トリメチルベンゾイルジフェニルフォスフィンオキサイドである、請求項７〜９、１１、１３、１５、１７のいずれか一項に記載の光硬化性組成物。 The photopolymerization initiator (D) is bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide , The photocurable composition according to any one of 15 and 17 . 難燃剤（Ａ）が式（４）におけるＲ２が炭素数２〜４のアルキレンである化合物と、式（５）におけるＲ２が炭素数２〜４のアルキレンである化合物の混合物であり、（メタ）アクリレート（Ｃ）が式（１４）の化合物と式（１５）の化合物の混合物である、請求項１９に記載の光硬化性組成物。 The flame retardant (A) is a mixture of a compound in which R 2 in the formula (4) is alkylene having 2 to 4 carbon atoms and a compound in which R 2 in the formula (5) is alkylene having 2 to 4 carbon atoms, ( The photocurable composition according to claim 19 , wherein the (meth) acrylate (C) is a mixture of the compound of formula (14) and the compound of formula (15). 式（１５）の化合物が、４−ヒドロキシブチルアクリレートである、請求項１９または２０に記載の光硬化性組成物。 The photocurable composition according to claim 19 or 20 , wherein the compound of the formula (15) is 4-hydroxybutyl acrylate. 常圧における沸点が３００℃以下の溶媒を含有しない、または常圧における沸点が３００℃以下の溶媒の組成物全体に占める割合が１０重量％以下である、請求項７〜９、１１、１３、１５、１７、１９〜２１のいずれか一項に記載の光硬化性組成物。 The ratio of the solvent having a boiling point at normal pressure of 300 ° C. or lower or a solvent having a boiling point at normal pressure of 300 ° C. or lower to the entire composition is 10% by weight or less , The photocurable composition according to any one of 15 , 17 , and 19-21 . 常圧における沸点が３００℃以下の溶媒を２０〜７０重量％含有する、請求項４〜６、１０、１２、１４、１６、１８のいずれか一項に記載の熱硬化性組成物。 The thermosetting composition according to any one of claims 4 to 6 , 10 , 12 , 14, 16 , and 18 containing 20 to 70% by weight of a solvent having a boiling point of 300 ° C or less at normal pressure. 常圧における沸点が３００℃以下の溶媒がガンマブチロラクトンである請求項２３に記載の熱硬化性組成物。 The thermosetting composition according to claim 23 , wherein the solvent having a boiling point of 300 ° C or less at normal pressure is gamma butyrolactone. 請求項４〜６、１０、１２、１４、１６、１８、２３、２４のいずれか一項に記載の熱硬化性組成物または請求項７〜９、１１、１３、１５、１７、１９〜２２のいずれか一項に記載の光硬化性組成物を用いて、基板上に難燃性硬化膜が形成された電子回路基板。 Claim 4～6,10,12, the thermosetting composition monomers other according to any one of 14,16,18,23,24 claims 7～9,11, 13, 15, 17, 19 using photocurable composition according to any one of to 22, the electronic circuit board flame retardant cured film is formed on the base plate. 請求項２５に記載された電子回路基板を有する電子部品。 An electronic component comprising the electronic circuit board according to claim 25 .
JP2007149993A 2007-06-06 2007-06-06 Flame retardant and curable composition using the same Expired - Fee Related JP5309478B2 (en)

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JP5699742B2 (en) * 2010-03-29 2015-04-15 日立化成株式会社 Phosphorus-containing acrylic resin and method for producing the same, acrylic resin composition, resin film, prepreg, metal foil with resin, metal foil-clad laminate, and printed wiring board
JP5699504B2 (en) * 2010-09-21 2015-04-15 Jnc株式会社 Photocurable ink composition for inkjet
JP5778514B2 (en) * 2011-07-28 2015-09-16 株式会社タムラ製作所 Flame retardant curable resin composition
WO2013114866A1 (en) * 2012-01-31 2013-08-08 片山化学工業株式会社 Flame-retardant substance and use as intermediate
JP6211781B2 (en) * 2012-03-27 2017-10-11 太陽インキ製造株式会社 Flame-retardant curable resin composition, dry film, flame-retardant coating and printed wiring board
WO2014034124A1 (en) * 2012-08-30 2014-03-06 片山化学工業株式会社 Simple production method
JP6076125B2 (en) 2013-02-15 2017-02-08 三光株式会社 Phosphorus (meth) acrylate compound and method for producing the same
JP6036937B2 (en) * 2015-08-03 2016-11-30 セイコーエプソン株式会社 Method for producing metal powder, method for producing ultraviolet curable ink jet composition, and method for producing recorded matter
CN112442212A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Phosphorus-containing reactive flame retardant and preparation method and application thereof
CN112442088A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Phosphorus-containing flame retardant with carboxyl and preparation method and application thereof
CN112442080A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Reactive flame retardant with phenolic hydroxyl groups and preparation method and application thereof
CN112442073A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Phosphorus-containing reactive flame retardant and preparation method and application thereof
CN112442072A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Reactive flame retardant with carboxylic acid or anhydride group, and preparation method and application thereof
CN112442083A (en) * 2019-08-28 2021-03-05 广东广山新材料股份有限公司 Phosphorus-containing flame retardant with anhydride and preparation method and application thereof
CN113880882B (en) * 2021-10-18 2023-07-18 泰州市正大化工有限公司 Phosphorus-nitrogen photocuring flame-retardant acrylic resin, flame-retardant coating prepared from same and application thereof

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JP3454544B2 (en) * 1993-08-02 2003-10-06 日本化薬株式会社 (Meth) acrylic acid ester, method for producing the same, curable resin composition using the same, and cured product thereof
WO2004111121A1 (en) * 2003-06-12 2004-12-23 Fuji Electric Holdings Co., Ltd. Reactive flame retardants and flame-retarded resin products
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