JPH03203915A - Water-soluble uv-curing resin composition - Google Patents
Water-soluble uv-curing resin compositionInfo
- Publication number
- JPH03203915A JPH03203915A JP34399989A JP34399989A JPH03203915A JP H03203915 A JPH03203915 A JP H03203915A JP 34399989 A JP34399989 A JP 34399989A JP 34399989 A JP34399989 A JP 34399989A JP H03203915 A JPH03203915 A JP H03203915A
- Authority
- JP
- Japan
- Prior art keywords
- water
- resin composition
- acrylamide
- soluble
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims description 15
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010453 quartz Substances 0.000 abstract description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract 2
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 239000004831 Hot glue Substances 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005498 polishing Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- 239000004156 Azodicarbonamide Substances 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 description 1
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 1
- -1 Michlersphenone Chemical compound 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 238000007517 polishing process Methods 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［ａ業上の利用分野］
本発明は、接着剤として用いられる水溶性の紫外線硬化
性樹脂組成物に関し、更に詳しくは水晶発振子等の製造
に際し、仮固定するために用いられる水溶性の紫外線硬
化性樹脂組成物に関する。Detailed Description of the Invention [Field of Application in Industry A] The present invention relates to a water-soluble ultraviolet curable resin composition used as an adhesive, more specifically for temporary fixing during the manufacture of crystal oscillators, etc. The present invention relates to a water-soluble ultraviolet curable resin composition used for.
［従来の技術］
従来、水晶発振子等の製造゛に際し、治具に素材を接着
剤により固定した後、切削または研磨等の機械加工を施
し、しかる後接着−剤を除去して加工製品を製造するこ
とが行われている。例えば水晶発振子の製造の場合には
、粗形状の水晶板材料を所望枚数積層した後、ホットメ
ルト接着剤により互いに接着して仮固定−し、この状態
で積層体を所定の形状に切削加工した後、ホットメルト
接着剤を除去して個々の製品を取り出すことにより製造
することが行われている。[Prior Art] Conventionally, when manufacturing crystal oscillators, etc., a material is fixed to a jig with an adhesive, then subjected to mechanical processing such as cutting or polishing, and then the adhesive is removed to produce the processed product. Manufacturing is being done. For example, in the case of manufacturing a crystal oscillator, after laminating a desired number of rough-shaped crystal plates, they are temporarily fixed by adhering them to each other with hot melt adhesive, and in this state, the laminated body is cut into a predetermined shape. After that, the hot melt adhesive is removed and the individual products are manufactured.
［発明が解決しようとする問題点］
しかしながら、このホットメルト接着剤を使用した場合
には、加熱工程を必要としするばかりでなく、接着に熟
練を要したり、接着力不足であったりする欠点を有して
おり、また接着剤の除去に際し、再度加熱工程を用いな
ければならず、更にはホットメルト接着剤の溶剤による
洗浄という操作を行う必要があり、工程が複雑となる問
題があり作業性が悪い。[Problems to be Solved by the Invention] However, when this hot melt adhesive is used, it not only requires a heating process, but also has disadvantages such as requiring skill for adhesion and insufficient adhesive strength. Moreover, when removing the adhesive, it is necessary to use a heating process again, and it is also necessary to perform an operation of cleaning the hot melt adhesive with a solvent, which complicates the process and makes the work difficult. Bad sex.
そこで本発明者は、前記の欠点ないし問題点を種々検討
した結果、仮接着剤として紫外線硬化性樹脂組成物を用
いることにより大幅な工程の簡略化が可能であることを
発見し、ここに本発明を完成するに至った。As a result of various studies on the above-mentioned drawbacks and problems, the inventors discovered that it is possible to greatly simplify the process by using an ultraviolet curable resin composition as a temporary adhesive. The invention was completed.
したがって本発明の目的は、上記問題点を解決したもの
で、水晶発振子等の製造に際し、水晶の切断、研磨工程
において水晶同士または水晶と治具との仮接着用に、大
幅な工程の簡略化が可能である紫外線硬化性樹脂組成物
を提供することにある。Therefore, an object of the present invention is to solve the above-mentioned problems, and to significantly simplify the process for temporarily adhering crystals to each other or to a jig in the cutting and polishing process of crystals in the production of crystal resonators, etc. The object of the present invention is to provide an ultraviolet curable resin composition that can be cured.
［問題点を解決するための手段］
上記問題点、即ち目的は、
１）ジアルキルアミノ（メタ）アクリルアミドもしくは
Ｎ−ビニル−２−ピロリドンまたはこれらの混合物と光
開始剤とを含むことを特徴とする水溶性紫外線硬化性樹
脂組成物及び、
２）前記第１項記載の紫外線硬化性樹脂組成物に水を含
有してなる水溶性紫外線硬化性樹脂組成物によって達成
された。[Means for Solving the Problems] The above problems, that is, objects, are characterized by: 1) containing dialkylamino(meth)acrylamide or N-vinyl-2-pyrrolidone or a mixture thereof and a photoinitiator; A water-soluble ultraviolet curable resin composition; and 2) a water-soluble ultraviolet curable resin composition comprising the ultraviolet curable resin composition described in item 1 above and water.
以下本発明を更に具体的に説明する。The present invention will be explained in more detail below.
本発明に用いられる水溶性モノマーとしてはジアルキル
アミノ（メタ）アクリルアミド、例えばＮ、Ｎ−ジメチ
ル（メタ）アクリルアミド、Ｎ。Water-soluble monomers used in the present invention include dialkylamino(meth)acrylamide, such as N,N-dimethyl(meth)acrylamide, N.
Ｎ−メチルエチル（メタ）アクリルアミド、Ｎ。N-methylethyl (meth)acrylamide, N.
Ｎ−ジエチル（メタ）アクリルアミド等、及びＮ−ビニ
ル−２−ピロリドン等の１種または２種以上の混合物が
用いられる。これらのうちＮ、Ｎ−ジメチルアクリルア
ミドが好ましく用いられる。One or a mixture of two or more of N-diethyl (meth)acrylamide and the like and N-vinyl-2-pyrrolidone are used. Among these, N,N-dimethylacrylamide is preferably used.
なお、（メタ）アクリルアミドは、アクリルアミドまた
はメタクリルアミドのいづれかを表す。Note that (meth)acrylamide represents either acrylamide or methacrylamide.
本発明に用いられる光開始剤としては、種々のものが用
いられ、例えばアセトフェノン、２．２＝ジエトキシア
セトフエノン、ベンゾフェノン、ミヒラーズフェノン、
ベンゾイン、ベンゾインメチルエーテル、ベンゾインエ
チルエーテル、ベンゾインブチルエーテル、２．２−ジ
メトキシ−２−フェニルアセトン、２−ヒドロキシ−２
−ジメトキシ−１−フェニルプロパン−１−オン、１−
ヒドロキシシクロへキシルフェニルケトン、アゾビスイ
ソブチルニトリル、メチルベンゾイルフォーメート、ア
ントラキノン、フエニルジスルフィド等が挙げられる。Various photoinitiators are used in the present invention, such as acetophenone, 2.2=diethoxyacetophenone, benzophenone, Michlersphenone,
Benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetone, 2-hydroxy-2
-dimethoxy-1-phenylpropan-1-one, 1-
Examples include hydroxycyclohexylphenyl ketone, azobisisobutylnitrile, methylbenzoyl formate, anthraquinone, phenyl disulfide, and the like.
本発明の水溶性紫外線硬化性樹脂組成物に対する光開始
剤の添加量は、０．２重量％〜１５重量％であり、好ま
しくは１重量％〜６重量％である。The amount of the photoinitiator added to the water-soluble ultraviolet curable resin composition of the present invention is 0.2% to 15% by weight, preferably 1% to 6% by weight.
また本発明では水を含有しているが、この水の含有量は
、２重量％〜５０重量％が好ましく、２重量％より少な
いと効果が乏しく、５０重量％より多いと組成物の硬化
速度の低下と硬化不足になる。Furthermore, the present invention contains water, and the content of this water is preferably 2% to 50% by weight; less than 2% by weight results in poor effects, and more than 50% by weight results in a hardening rate of the composition. This results in a decrease in hardness and insufficient curing.
本発明において、水を添加したことによる効果は、以下
の如くである。In the present invention, the effects of adding water are as follows.
１）硬化物硬度が低下し、研磨切削時の衝撃強度が増加
する。1) The hardness of the cured product decreases and the impact strength during polishing and cutting increases.
２）研磨切削後、水で溶解する場合、水になじみやすく
なり、剥離速度が速くなる。2) When dissolved in water after polishing and cutting, it becomes more compatible with water and the peeling speed becomes faster.
３）接着強度が増加する。3) Adhesive strength increases.
４）減量原価の低減が図られる。4) Reduction of costs will be achieved.
本発明の水溶性紫外線硬化性樹脂組成物には、この他必
要に応じて作業性を向上させるために増粘剤、例えばポ
リ−Ｎ−ビニル−ピロリドンを加えることができる。In addition, a thickener such as poly-N-vinyl-pyrrolidone may be added to the water-soluble ultraviolet curable resin composition of the present invention in order to improve workability, if necessary.
また剥離促進剤として発泡剤を加えることができる。好
ましい発泡剤としては、アゾ化合物、例えばアゾビスイ
ソブチルニトリル、アゾジカルボンアミド等、スルホニ
ルヒドラジド化合物、例えばｐ−トルエンスルホニルヒ
ドラジド、ｐ、 ｐ−オキシビス（ベンゼンスルホニル
ヒドラジド）等、ニトロソ化合物、例えばＮ、Ｎ−ジニ
トロソペンタメチレンテトラミン等が挙げられる。A foaming agent can also be added as a release accelerator. Preferred blowing agents include azo compounds such as azobisisobutylnitrile, azodicarbonamide, sulfonylhydrazide compounds such as p-toluenesulfonylhydrazide, p,p-oxybis(benzenesulfonylhydrazide), nitroso compounds such as N,N - dinitrosopentamethylenetetramine and the like.
［実施例］
以下本発明の実施例を挙げるが、本発明はこの実施例に
限定されるものではない。[Example] Examples of the present invention will be described below, but the present invention is not limited to these Examples.
実施例１〜５
各成分を第１表に示す配合割合で均一に攪拌して混合し
て、水溶性紫外線硬化性樹脂組成物の実施例１〜５を作
製した。Examples 1 to 5 Examples 1 to 5 of water-soluble ultraviolet curable resin compositions were prepared by uniformly stirring and mixing each component in the proportions shown in Table 1.
ついで、比較例も同様な方法で各成分を第１表に示す配
合割合で均一に攪拌して比較組成物１及び２を作製した
。Next, comparative compositions 1 and 2 were prepared in the same manner as comparative examples by uniformly stirring each component in the proportions shown in Table 1.
得られた各組成物を、それぞれ５ｆｆｌＩ＋の２枚の水
晶板に塗布して張り合せた。これを１５００１ｊ／（１
２の紫外線照射量で硬化させた。ついで研磨工程を実施
した後、６０℃の水中に浸漬し、剥離までの時間を１時
間毎に測定した。Each of the obtained compositions was applied to two 5fflI+ quartz plates and bonded together. This is 15001j/(1
It was cured with an ultraviolet irradiation dose of 2. After carrying out a polishing step, it was immersed in water at 60° C., and the time until peeling was measured every hour.
得られた結果を第２表に示す。The results obtained are shown in Table 2.
第２表から明らかなように、実施例１〜５でよ、−比較
例に比べて剥離までの時間が３〜１２時羽と短く、剪断
接着力試験も良好であることがわ１）る。As is clear from Table 2, in Examples 1 to 5, the time to peeling was shorter (3 to 12 hours) than in the comparative example, and the shear adhesion test was also good1). .
［発明の効果］
本発明は、水溶性紫外線硬化性樹脂組成物に水？加える
ことにより、組成物の特性を変えることｔく、むしろ接
着強度か増加するとともに大幅な二稀短縮を行うことが
できる効果を有する。[Effects of the Invention] The present invention provides water-soluble ultraviolet curable resin compositions. By adding it, it does not change the properties of the composition, but rather has the effect of increasing the adhesive strength and significantly shortening the adhesive strength.
ヨ願人 ケミチック株式会社た埋入弁理士
中 島 幹 雄外１名1 patent attorney, Miki Nakajima, and Yugai of Chemistic Co., Ltd.
Claims (1)
Ｎ−ビニル−２−ピロリドンまたはこれらの混合物と光
開始剤とを含むことを特徴とする水溶性紫外線硬化性樹
脂組成物。２）請求項１記載の紫外線硬化性樹脂組成物
に水を含有してなる水溶性紫外線硬化性樹脂組成物。1) A water-soluble ultraviolet curable resin composition comprising dialkylamino(meth)acrylamide or N-vinyl-2-pyrrolidone or a mixture thereof and a photoinitiator. 2) A water-soluble ultraviolet curable resin composition comprising the ultraviolet curable resin composition according to claim 1 containing water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34399989A JPH03203915A (en) | 1989-12-29 | 1989-12-29 | Water-soluble uv-curing resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34399989A JPH03203915A (en) | 1989-12-29 | 1989-12-29 | Water-soluble uv-curing resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03203915A true JPH03203915A (en) | 1991-09-05 |
Family
ID=18365876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34399989A Pending JPH03203915A (en) | 1989-12-29 | 1989-12-29 | Water-soluble uv-curing resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03203915A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019240106A1 (en) * | 2018-06-14 | 2019-12-19 | Jnc株式会社 | Polymerizable composition, ink jet ink, heat resistant soluble member, three-dimensional structure with support, and method of manufacturing three-dimensional molded article |
-
1989
- 1989-12-29 JP JP34399989A patent/JPH03203915A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019240106A1 (en) * | 2018-06-14 | 2019-12-19 | Jnc株式会社 | Polymerizable composition, ink jet ink, heat resistant soluble member, three-dimensional structure with support, and method of manufacturing three-dimensional molded article |
| CN112135846A (en) * | 2018-06-14 | 2020-12-25 | 捷恩智株式会社 | Polymerizable composition, ink for ink jet, heat-resistant soluble member, three-dimensional structure with support, and method for producing three-dimensional structure |
| JPWO2019240106A1 (en) * | 2018-06-14 | 2021-07-08 | Jnc株式会社 | Method for manufacturing polymerizable composition, ink for inkjet, heat-resistant soluble member, three-dimensional structure with support, and three-dimensional model |
| CN112135846B (en) * | 2018-06-14 | 2022-08-23 | 捷恩智株式会社 | Polymerizable composition, ink for inkjet, heat-resistant soluble member, three-dimensional structure, and method for producing three-dimensional structure |
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