JPS5936135A - Photo-curable polyorgano-siloxane - Google Patents
Photo-curable polyorgano-siloxaneInfo
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- JPS5936135A JPS5936135A JP14615282A JP14615282A JPS5936135A JP S5936135 A JPS5936135 A JP S5936135A JP 14615282 A JP14615282 A JP 14615282A JP 14615282 A JP14615282 A JP 14615282A JP S5936135 A JPS5936135 A JP S5936135A
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- carbon
- group
- coating
- double bond
- polyorganosiloxane
- Prior art date
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Abstract
Description
【発明の詳細な説明】
本発明は、新規な光硬化性ポリオルガノシロキサンに関
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel photocurable polyorganosiloxane.
光重合性ポリオルガノシロキサンは、すでに種々のもの
が開発され半導体装置(ダイオード。Various photopolymerizable polyorganosiloxanes have already been developed for use in semiconductor devices (diodes, etc.).
トランジスタなど)、プリント基板などのコーテング剤
、印刷における製版などの種々の用途に利用されている
。It is used in a variety of applications, such as coating agents for printed circuit boards (transistors, etc.), and plate-making in printing.
しかし、従来の光硬化性ポリオルガノシロキサンは、感
光基がほとんどビニル基であるため光を照射するとラジ
カル反応を起こして硬化する。このため、被膜表面は酸
素の影響を受け、硬化不充分であったり、被膜が均一に
硬化しないという欠点がある。However, in conventional photocurable polyorganosiloxanes, most of the photosensitive groups are vinyl groups, so when irradiated with light, a radical reaction occurs and the polyorganosiloxane is cured. For this reason, the surface of the coating is affected by oxygen, resulting in insufficient curing or non-uniform curing of the coating.
本発明の目的は、上記した従来技術の欠点をなくし、被
膜表面の硬化が良好であり、かつ被膜が均一に硬化する
光硬化性ポリオルガノシロキサンを提供することにある
。It is an object of the present invention to provide a photocurable polyorganosiloxane which eliminates the drawbacks of the prior art described above, and which cures the coating surface well and uniformly.
上記目的は、酸素の影響を受けにくい比較的長寿命のシ
リル活性種で光硬化するもので達成される。The above object is achieved by using a photocurable silyl active species that is relatively long-lived and is not easily affected by oxygen.
すなわち、本発明は、一般式(1)で表わされる繰返し
単位を有する
以 下 余 白
R3
(但し、R1は芳香族残基、炭素−炭素二重結合を有す
る基、R,、R3,R,、R,、R,は低級脂肪族残基
、芳香族残基、炭素−炭素二重結合を有する基、lは1
〜100,77Lは0〜300の整数である。)平均分
子量2000〜100,000の光硬化性ポリオルガノ
シロキサンにより達成される。That is, the present invention has a repeating unit represented by the general formula (1). (However, R1 is an aromatic residue, a group having a carbon-carbon double bond, , R,, R, is a lower aliphatic residue, an aromatic residue, a group having a carbon-carbon double bond, l is 1
~100,77L is an integer from 0 to 300. ) Achieved by a photocurable polyorganosiloxane having an average molecular weight of 2000 to 100,000.
さらに本発明の詳細な説明する。本発明は、一般式(2
)で示されるジシラン化合物とR2
!
R8
(但し、R1は芳香族残基、炭素−炭素二重結合を有す
る基、R2y R3J R4は低級脂肪族残基。Further, the present invention will be explained in detail. The present invention is based on the general formula (2
) and R2! R8 (However, R1 is an aromatic residue, a group having a carbon-carbon double bond, R2y R3J R4 is a lower aliphatic residue.
芳香族残基、炭素〜炭素二重結合を有する基、Xはハロ
ゲン原子、炭素数6以下のアルコキン基から成る加水分
解可能な基を表わす)、必要に応じて、一般式(3)で
示されるシラン化合物とを、そのままもしくはトルエン
、キシレンなどの不活性溶媒で希釈してから加水分解し
R6
X −S i −X −−−11,=−(3)■
6
(但し、R,、R,は低級脂肪族残基、芳香族残基、炭
素−炭素二重結合を有する基、Xはハロゲン原子、炭素
数6以下のアルコキシ基からなる加水分解可能な基を示
す)、塩酸などの副生物を水洗処理などによって除去す
る。なお、上記の加水分解は、メタノールなどの低級ア
ルコールを加水分解補助剤として加えて行なっても良い
。aromatic residue, a group having a carbon-carbon double bond, R6 , indicates a lower aliphatic residue, an aromatic residue, a group having a carbon-carbon double bond, X indicates a hydrolyzable group consisting of a halogen atom or an alkoxy group having 6 or less carbon atoms) Remove living organisms by washing with water, etc. Note that the above hydrolysis may be performed by adding a lower alcohol such as methanol as a hydrolysis auxiliary agent.
ついで、加水分解生成物をトルエン、キシレンなどの不
活性溶媒で加水分解生成物濃度が5〜70重量%となる
よう希釈し、これに脱水縮合触媒として触媒量の強塩基
性物質を添加し、常温(18゛C)170°0で数10
分〜数10時間攪拌して脱水縮合反応を起こし前記した
一般式(11で示される光硬化性ポリオルガノシロキサ
ンを4る。Next, the hydrolyzed product is diluted with an inert solvent such as toluene or xylene so that the hydrolyzed product concentration is 5 to 70% by weight, and a catalytic amount of a strong basic substance is added thereto as a dehydration condensation catalyst. Number 10 at room temperature (18°C) 170°0
The photocurable polyorganosiloxane represented by the general formula (11) is prepared by stirring for several minutes to several tens of hours to cause a dehydration condensation reaction.
この脱水縮合反応は、その反応系に共存するトルエン、
キシレンなどの不活性溶媒が還流する温度で生成水を適
便系外に除去しながら行なえば、得られた光硬化性ポリ
オルガノシロキサンがゲル化を起こすことがない。This dehydration condensation reaction involves toluene coexisting in the reaction system,
If the process is carried out at a temperature at which an inert solvent such as xylene refluxes while removing the produced water conveniently from the system, the resulting photocurable polyorganosiloxane will not undergo gelation.
その後、前記脱水縮合触媒(強塩基性物質)をたとえば
酢酸で中和するなどして不活性化または除去する。Thereafter, the dehydration condensation catalyst (strongly basic substance) is inactivated or removed, for example, by neutralizing it with acetic acid.
このようにして不純物のない光硬化性ポリオルガノシロ
キサンを得る。In this way, a photocurable polyorganosiloxane free of impurities is obtained.
本発明の前記一般式(11で示される光硬化性ポリオル
ガノシロキサンとしては、例えば以下の繰返し単位を有
するものが挙げられる。Examples of the photocurable polyorganosiloxane of the present invention represented by the general formula (11) include those having the following repeating units.
Bs M ■ Ms C”E。Bs M ■ Ms C”E.
C1l。C1l.
CM −5t C’ II CHa33
CH=CH2−
(但し、式中lは1−100,771は0〜600)本
発明で用いる前記一般式(2)で示されるジシラン化合
物は、(α)例えば、1,1.1− トIJメチルー2
−フェニルジクロロジシラン、 1,1.1−トリエチ
ル−2−フェニルジクロロジシラン、1゜1.1−ヅメ
ナルフェニル−2−フェニルジクロロジシラン、 1,
1.1−ジメチルビニル−2−フェニルジクロロジシラ
ン、 1,1.1−トリメチル−2−) ’Jルジクロ
ロジシラン、1,1.1−トリメチル−2−ビニルジク
ロロジシランのうちから選ばれた少なくとも一種類の化
合物、(h)前記(α)のジクロロジシラン化合物の一
個の塩素原子を加水分解してOH−に変えた化合物のう
ちから選ばれた少な(とも一種類の化合物、(C)前記
(α)のジクロロジシラン化合物の二個の塩素原子を全
部加水分解してOR−に変えた化合物のうちから選ばれ
た少なくとも一種類の化合物、(d、)前記(α)のジ
クロロジシラン化合物の一個の塩素原子を加水分解して
OH−に変え、かつ残る一個の塩素原子をメタノール、
エタノールなどでアルコキシ化した化合物(アルコキシ
化してから加水分解しても良い)のうちから選ばれた少
なくとも一種類の化合物、(e)前記(a)のジクロロ
シフラン化合物の二個の塩素原子を全部をメタノールエ
タノールなどでアルコキシ化した化合物のうちから選ば
れた少なくとも一種類の化合物、(f)上記(a)〜(
e)項の混合物が挙げられる。CM -5t C' II CHa33 CH=CH2- (However, in the formula, l is 1-100, 771 is 0-600) The disilane compound represented by the general formula (2) used in the present invention is (α), for example, 1,1.1- IJ methyl-2
-Phenyldichlorodisilane, 1,1.1-triethyl-2-phenyldichlorodisilane, 1゜1.1-dumenalphenyl-2-phenyldichlorodisilane, 1,
At least one selected from the group consisting of 1,1-dimethylvinyl-2-phenyldichlorodisilane, 1,1,1-trimethyl-2-)'J-dichlorodisilane, and 1,1,1-trimethyl-2-vinyldichlorodisilane. one type of compound, (h) a small number of compounds selected from among the compounds in which one chlorine atom of the dichlorodisilane compound (α) is hydrolyzed and converted to OH-; (C) one type of compound as described above; (d) at least one compound selected from compounds in which all two chlorine atoms of the dichlorodisilane compound of (α) are hydrolyzed and converted to OR-; (d) of the dichlorodisilane compound of (α); One chlorine atom is hydrolyzed and converted to OH-, and the remaining chlorine atom is converted into methanol,
At least one compound selected from compounds alkoxylated with ethanol etc. (may be hydrolyzed after alkoxylation); (e) two chlorine atoms of the dichlorosifurane compound of (a) above; At least one compound selected from compounds entirely alkoxylated with methanol, ethanol, etc., (f) the above (a) to (
Mixtures of item e) may be mentioned.
さらに、本発明で用いる前記一般式(3)で示されるシ
ラン化合物は、ω)例えばジメチルジクロロシラン、ジ
エチルジクロロシラン、メチルエチルジクロロシラン、
メチルビニルジクロロシラン、メチルフェニルジクロロ
シラン、ビニルフェニルジクロロシラン、ジフェニルジ
クロロシランおよびこれらのクロロシランに対応するア
ルコキシシランのうちから選ばれた少なくとも一種類の
化合物、Ch)前記(、りのジクロロジシラン化合物の
一個の塩素原子を加水分解してOB−に変えた化合物の
うちから選ばれた少なくとも一種類の化合物、(i)前
記0)のジクロロジシラン化合物の二個の塩素原子を全
部加水分解してOH−に変えた化合物のうちから選ばれ
た少なくとも一種類の化合物、0゛)前記(!I)のジ
クロロジシラン化合物の一個の塩素原子を加水分解して
OH−に変え、かつ残る一個の塩素原子をアルコキシ化
した化合物(アルコキシ化してから加水分解しても良い
)のうちから選ばれた少な(とも一種類の化合物、(k
)前記(!I)のジクロロジシラン化合物の二個の塩素
原子を全部アルコキシ化した化合物のうちから選ばれた
少なくとも一種類の化合物、(1)上記(&)〜(k)
項の混合物が挙げられる。Furthermore, the silane compound represented by the general formula (3) used in the present invention is ω), for example, dimethyldichlorosilane, diethyldichlorosilane, methylethyldichlorosilane,
At least one compound selected from methylvinyldichlorosilane, methylphenyldichlorosilane, vinylphenyldichlorosilane, diphenyldichlorosilane, and alkoxysilanes corresponding to these chlorosilanes; At least one compound selected from compounds in which one chlorine atom is hydrolyzed to OB-, (i) all two chlorine atoms of the dichlorodisilane compound of 0 above are hydrolyzed to OB-. - at least one compound selected from the compounds in which the dichlorodisilane compound of (!I) is hydrolyzed to convert one chlorine atom into OH-, and the remaining one chlorine atom A small number of compounds (at least one kind of compound, (k
) at least one compound selected from the compounds in which all two chlorine atoms of the dichlorodisilane compound of (!I) are alkoxylated, (1) the above (&) to (k);
A mixture of terms may be mentioned.
また、前記一般式(11と前記一般式(2)の混合割合
は、光硬化性を損わない程度であれば限定されるもので
はない。Further, the mixing ratio of the general formula (11) and the general formula (2) is not limited as long as it does not impair photocurability.
本発明に用いる脱水縮合触媒(強塩基性物質)は、例え
ば水酸化カリウム、水酸化ナトリウム。Examples of the dehydration condensation catalyst (strongly basic substance) used in the present invention include potassium hydroxide and sodium hydroxide.
水酸化セシウムなどのアルカリ金属水酸化物、水酸化テ
トラメチルアンモニウム、水酸化ベンジルトリメチルア
ンモニウムなどの第4級アンモニウム水酸化物、水酸化
テトラブチルホスホニウムなどの第4級ホスホニウム水
酸化物等が挙げられる。Examples include alkali metal hydroxides such as cesium hydroxide, quaternary ammonium hydroxides such as tetramethylammonium hydroxide, benzyltrimethylammonium hydroxide, and quaternary phosphonium hydroxides such as tetrabutylphosphonium hydroxide. .
希釈剤は、例えば、下記の脱水縮合反応用の不活性溶媒
の他、光硬化性ポリオルガノシロキサンの良溶媒であれ
ばよい。The diluent may be, for example, an inert solvent for the dehydration condensation reaction described below or a good solvent for photocurable polyorganosiloxane.
本発明に用いる脱水縮合反応用の不活性溶媒は、例工ば
トルエン、キシレン、テトラリン。Examples of the inert solvent for the dehydration condensation reaction used in the present invention include toluene, xylene, and tetralin.
ヘラトロールなどの芳香族炭化水素系溶媒が挙られる。Examples include aromatic hydrocarbon solvents such as heratrol.
前記一般式(1)で示される光硬化性ポリオルガノシロ
キサンは、希釈剤に溶解し、この溶液を支持体上に塗布
し、乾燥し、これに遠紫外線。The photocurable polyorganosiloxane represented by the general formula (1) is dissolved in a diluent, and this solution is applied onto a support, dried, and then exposed to deep ultraviolet rays.
紫外線、軟X線、電子線などを照射すると被膜表面の硬
化が良好であり、かつ、被膜は均一に硬化する。When irradiated with ultraviolet rays, soft X-rays, electron beams, etc., the surface of the coating is well cured, and the coating is uniformly cured.
なお、用途によっては前記の遠紫外線、紫外線、軟X線
、を子線などを露光とともに加熱すれば基板との接着性
が向上する。Note that, depending on the application, the adhesion to the substrate may be improved by heating the above-mentioned deep ultraviolet rays, ultraviolet rays, soft X-rays, etc. together with exposure.
本発明で用いる基板は、例えば銅、アルミニウムなどの
金属、Tie、 、 SiO、Sin、 、 Ta2O
,などの金属酸化物、窒化ケイ素、ポリイミド、ポリア
ミド、ポリエステルなどの合成樹脂などが挙げられる。The substrate used in the present invention is made of, for example, metal such as copper or aluminum, Tie, SiO, Sin, Ta2O.
Examples include metal oxides such as , silicon nitride, synthetic resins such as polyimide, polyamide, and polyester.
また、本発明の光硬化性ポリオルガノシロキサンは、半
導体、磁気バブル、プリント基板などのコーテング剤、
塗料などへの応用も可能である。In addition, the photocurable polyorganosiloxane of the present invention can be used as a coating agent for semiconductors, magnetic bubbles, printed circuit boards, etc.
It can also be applied to paints, etc.
以下、実施例により本発明を説明する。The present invention will be explained below with reference to Examples.
実施例1
かきまぜ機、冷却器および滴下ロートをとりつけた10
0−の三つロフラスコに、34+d(71)0.1A’
水酸化ナトウム水溶液と、40−のエーテルを入れた。Example 1 10 equipped with stirrer, cooler and dropping funnel
34+d(71)0.1A' in a 0- three-necked flask
A sodium hydroxide aqueous solution and 40-ether were added.
これを水冷下に激しくかきませながら、滴下ロートより
10−の乾燥エーテルに溶解した1、1.1− ) I
J 、7’ チル−2−フェニルジクロロフジ。ラン5
fをできるだけ短時間に加えた。滴下終了後、直ちにエ
ーテル層を分解し、水層はエーテル抽出し、これら両エ
ーテル層を合わせて水洗した。これを炭酸カルシウム上
で乾燥してからエーテルを留去し、残液に約20−のペ
ンタンを加えて冷却した。生成物2.5tを得た。1,1.1-) I was dissolved in 10-1 dry ether from a dropping funnel while stirring vigorously while cooling with water.
J, 7' thyl-2-phenyldichlorofusi. run 5
f was added as quickly as possible. Immediately after the addition was completed, the ether layer was decomposed, the aqueous layer was extracted with ether, and both ether layers were combined and washed with water. This was dried over calcium carbonate, the ether was distilled off, and approximately 20-pentane was added to the remaining solution, followed by cooling. 2.5 t of product was obtained.
次に30m1の二つロフラスコにトルエン3 mlに溶
解した1、1.1− )ジメチル−2−フェニルジクロ
ロジシラン22および水酸化カリウム0.01Fを入れ
、マグネチツクスタラーでかきまぜながらトルエンの還
流温度で約4時間保持した。この際、生成した水は分留
し、さらにトルエンを約2−を分留し、140〜150
°0の温度で約2時間を行なった。生成物を10−のト
ルエンに溶かしこれにメタノール10コを加えて光硬化
性ポリオルガノシロキサン(以下ポリマと略す)を沈殿
させた。沈殿したポリマはメタノールで水洗しついで水
で洗浄し、減圧乾燥させた。このようにして得られたポ
リマの収率は84%(+、ar)であった。また、この
ポリマの数平均分子量は2500であった。Next, put 1,1,1-)dimethyl-2-phenyldichlorodisilane 22 dissolved in 3 ml of toluene and 0.01 F of potassium hydroxide into a 30 ml two-bottle flask, and stir with a magnetic stirrer until the reflux temperature of toluene is reached. It was held for about 4 hours. At this time, the produced water is fractionally distilled, and toluene is further fractionated to about 2-140 to 150
The test was carried out for about 2 hours at a temperature of 0°C. The product was dissolved in 10-g of toluene and 10 g of methanol was added thereto to precipitate a photocurable polyorganosiloxane (hereinafter abbreviated as polymer). The precipitated polymer was washed with methanol, then water, and dried under reduced pressure. The yield of the polymer thus obtained was 84% (+, ar). Further, the number average molecular weight of this polymer was 2,500.
上記で得られたポリマ0.5fを、トルエン5rn!。Add 0.5f of the polymer obtained above to 5rn! of toluene! .
に溶解して試料を調整した。ついで、これをガラス板上
に塗布し、これを100°0,30分間乾燥し、ついで
紫外線を30cn1はなれた3A’F超高圧水銀灯から
2分間照射したところ、被膜表面の硬化が良好であり、
かつ被膜は均一に硬化していた。また、耐薬品性もすぐ
れていた。The sample was prepared by dissolving it in Next, this was coated on a glass plate, dried at 100° for 30 minutes, and then irradiated with ultraviolet rays for 2 minutes from a 3A'F ultra-high pressure mercury lamp 30cn1 apart, and the surface of the coating was well cured.
Moreover, the coating was uniformly cured. It also had excellent chemical resistance.
実施例2 第1表のム1〜A6に示すジシラン化合物。Example 2 Disilane compounds shown in columns 1 to A6 of Table 1.
シラン化合物、溶媒および触媒を用い、実施例1と同様
にして六種類のポリマを得た。これらポリマの数平均分
子量、収率は第1表のようであった。また得られた六種
類のポリマを、それぞれガラス板上に塗布し、乾燥し、
紫外線を照射したところ、第2表の/I61〜6に示す
ようにそれぞれ被膜表面の硬化が良好であり、かつ被膜
は均一に硬化していた。また、第2表に示すように耐薬
品性も良好であった。Six types of polymers were obtained in the same manner as in Example 1 using a silane compound, a solvent, and a catalyst. The number average molecular weights and yields of these polymers were as shown in Table 1. In addition, each of the six types of polymers obtained was applied onto a glass plate, dried,
When irradiated with ultraviolet rays, as shown in /I61-6 in Table 2, the surface of each coating was well cured, and the coating was uniformly cured. Furthermore, as shown in Table 2, the chemical resistance was also good.
以 下 余 白
比較例1
末端ビニル基を有するポリジメチルシロキサン(数平均
分子量2100 ) 1yを、トルエン1〇−に溶解し
て試料を調整した。ついで、実施例1と同様にして光硬
化被膜を得た。被膜表面は硬化不十分であり、被膜は不
均一に硬化していた。Margins below Comparative Example 1 A sample was prepared by dissolving polydimethylsiloxane (number average molecular weight 2100) 1y having a terminal vinyl group in 10 - of toluene. Then, a photocured coating was obtained in the same manner as in Example 1. The surface of the coating was insufficiently cured, and the coating was non-uniformly cured.
以上詳述したように本発明によれば、以下の(1)〜6
10の効果がある。As detailed above, according to the present invention, the following (1) to 6 are possible.
There are 10 effects.
(])光硬化性ポリオルガノシロキサンの合成が容易で
ある。(]) Synthesis of photocurable polyorganosiloxane is easy.
(11)光硬化性ポリオルガノシロキサンは、被膜表面
が充分に硬化し、かつ被膜は均一に硬化する。又耐薬品
性も良好である。(11) Photocurable polyorganosiloxane has a coating surface that is sufficiently cured and a coating that is uniformly cured. It also has good chemical resistance.
(iiD コーテング剤に適している。(iiD Suitable as a coating agent.
Claims (1)
る基、R,、R,、R,、R,、R6は低級脂肪族残基
、芳香族残基、炭素−炭素二重結合を有する基、lは1
〜1oo1mはo〜3ooの整数である)で表わされる
繰返し単位を有する平均分子量約2000〜1oo、0
00の光硬化性ポリオルガノシロキサン。[Claims] General formula (where R is an aromatic residue, a group having a carbon-carbon double bond, R,, R,, R,, R,, R6 is a lower aliphatic residue, an aromatic group residue, group having a carbon-carbon double bond, l is 1
-1oo1m is an integer from o to 3oo) with an average molecular weight of about 2000 to 1oo, 0
00 photocurable polyorganosiloxane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14615282A JPS5936135A (en) | 1982-08-25 | 1982-08-25 | Photo-curable polyorgano-siloxane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14615282A JPS5936135A (en) | 1982-08-25 | 1982-08-25 | Photo-curable polyorgano-siloxane |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5936135A true JPS5936135A (en) | 1984-02-28 |
JPS6254343B2 JPS6254343B2 (en) | 1987-11-14 |
Family
ID=15401307
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14615282A Granted JPS5936135A (en) | 1982-08-25 | 1982-08-25 | Photo-curable polyorgano-siloxane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5936135A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63193127U (en) * | 1987-05-29 | 1988-12-13 | ||
JPS63193128U (en) * | 1987-05-29 | 1988-12-13 | ||
JPH0294939U (en) * | 1989-01-18 | 1990-07-27 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0830517B2 (en) * | 1987-10-12 | 1996-03-27 | 日本発条株式会社 | Block for transmission belt |
-
1982
- 1982-08-25 JP JP14615282A patent/JPS5936135A/en active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63193127U (en) * | 1987-05-29 | 1988-12-13 | ||
JPS63193128U (en) * | 1987-05-29 | 1988-12-13 | ||
JPH0294939U (en) * | 1989-01-18 | 1990-07-27 |
Also Published As
Publication number | Publication date |
---|---|
JPS6254343B2 (en) | 1987-11-14 |
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