JPS5917133B2 - Additive for mineral-filled thermosetting resin composite materials - Google Patents
Additive for mineral-filled thermosetting resin composite materialsInfo
- Publication number
- JPS5917133B2 JPS5917133B2 JP8465181A JP8465181A JPS5917133B2 JP S5917133 B2 JPS5917133 B2 JP S5917133B2 JP 8465181 A JP8465181 A JP 8465181A JP 8465181 A JP8465181 A JP 8465181A JP S5917133 B2 JPS5917133 B2 JP S5917133B2
- Authority
- JP
- Japan
- Prior art keywords
- additive
- thermosetting resin
- carbon atoms
- group
- composite materials
- 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.)
- Expired
Links
- 239000000654 additive Substances 0.000 title claims description 19
- 230000000996 additive effect Effects 0.000 title claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 16
- 239000000463 material Substances 0.000 title claims description 8
- 239000000805 composite resin Substances 0.000 title claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 title description 2
- 239000011707 mineral Substances 0.000 title description 2
- 239000000126 substance Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 14
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 238000011049 filling Methods 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 239000011147 inorganic material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000180587 Pinnidae Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
本発明は無機物充填熱硬化性樹脂複合材料用添加剤に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to additives for mineral-filled thermosetting resin composite materials.
より詳述すれば、熱硬化性樹脂に無機物を充填して複合
材料を得るにおいて使用す０ る添加剤に関する。熱硬
化性樹脂に無機材料であるところの無機物を充填して、
複合材料が得られることはよく知られている。More specifically, the present invention relates to an additive used in obtaining a composite material by filling a thermosetting resin with an inorganic substance. By filling a thermosetting resin with an inorganic material,
It is well known that composite materials can be obtained.
熱硬化性樹脂に無機物を充填する目的は樹脂に５ よつ
て異るが、大ざつぱに言つて、製品のコストダウン、作
業性の改善、弾性率および硬度の同士、硬化時および成
形時の発熱温度の低下、熱膨張係数および収縮率等の減
少等である。The purposes of filling thermosetting resins with inorganic substances vary depending on the resin, but broadly speaking, they can be used to reduce product costs, improve workability, improve elastic modulus and hardness, and reduce heat generation during curing and molding. These include a decrease in temperature, a decrease in the coefficient of thermal expansion and contraction rate, etc.
一般にこれら無機物の熱硬化性樹脂への充填に際し、添
加剤と９ して例えばカップリング剤、定着剤がじばじ
ば使用されている。このカップリング剤、定着剤は、樹
脂申への無機物の配合または充填を促進すると、共に、
それらの界面に接着層を形成する。カップリング剤、定
着剤はシランおよびチタン５ 系材料である。Generally, when filling thermosetting resins with these inorganic substances, additives such as coupling agents and fixing agents are often used. This coupling agent and fixing agent both promote the blending or filling of inorganic substances into the resin, and
An adhesive layer is formed at the interface between them. The coupling agent and fixing agent are silane and titanium 5 based materials.
しかしながら、このシランおよびチタン系材料を使用し
た場合、無機物充填時の粘度降下作用が小さく、また無
機物の充填量が低く、またある場合には表面活性特性を
減退させるという欠点が存在する。ク 本発明者等は前
記欠点を改良するため鋭意研究を重ねた結果、本発明を
提供するに至つたものである。However, when these silane and titanium-based materials are used, there are disadvantages in that the viscosity-lowering effect upon loading with inorganic substances is small, the loading amount of inorganic substances is low, and in some cases, the surface active properties are reduced. H. The present inventors have conducted intensive research to improve the above-mentioned drawbacks, and as a result, they have arrived at providing the present invention.
すなわち、一般式（Ｉ）
５ＣＨ２■Ｃ−Ｃ−Ｏ÷Ｒ１−０÷ｎＰ−Ｒ２・・・・
・・・・・（Ｉ）（式中、ＲはＨもしくはＣＨ３一基、
Ｒ１は−ＣＨ２−ＣＨ２一基もしくは−ＣＨ−ＣＨ２一
基もしくは−ＣＨ−ＣＨ２一基またはこれらの基の組み
合せを表わ
し、Ｒ２は−０Ｈ基もしくはＣＨ２＝Ｃ−Ｃ−０でＲ１
−０今。That is, general formula (I) 5CH2■C-C-O÷R1-0÷nP-R2...
...(I) (wherein R is H or one CH3 group,
R1 represents -CH2-CH2 group, -CH-CH2 group, -CH-CH2 group, or a combination of these groups, R2 is -0H group or CH2=C-C-0, and R1
-0 now.
もしくは−０−Ｒ３を表わし、Ｒ３は−（−Ｒ１−０＋
ＲＩｌＯ−Ｒ４を表わし、Ｒ４は炭素数３〜１８の飽和
アルキル基もしくは炭素数３〜１８の不飽和アルキル基
もしくは炭素数１〜１２の飽和アルキルフエノールの残
基もしくは炭素数１〜１２の不飽和アルキルフエノール
の残基を表わす。ｎは１〜５０の整数、ｍはＯもしくは
１〜５０の整数を表わす。以下同じ。）で表わされるリ
ン酸エステルを主成分とするリン酸エステル類より成る
無機物充填熱硬化性樹脂複合材料用添加剤（以下添加剤
という）である。or -0-R3, where R3 is -(-R1-0+
RIIO-R4, where R4 is a saturated alkyl group having 3 to 18 carbon atoms, an unsaturated alkyl group having 3 to 18 carbon atoms, a residue of a saturated alkylphenol having 1 to 12 carbon atoms, or an unsaturated group having 1 to 12 carbon atoms. Represents an alkylphenol residue. n represents an integer of 1 to 50, and m represents O or an integer of 1 to 50. same as below. ) is an additive for inorganic-filled thermosetting resin composite materials (hereinafter referred to as additive) consisting of phosphoric acid esters whose main component is a phosphoric acid ester represented by:
本発明で使用する一般式（１）で表わされるリン酸エス
テルを主成分とするリン酸エステル類（以下一般式（１
）で表わされるリン酸エステル類という）としてはアル
コール類と無水リン酸とを反応させたものが挙げられる
。このアルコール類と無水リン酸との反応は公知の力法
に従つて行うものであり、また必要に応じて重合禁止剤
を使用する。アルコール類としてはＣＨ２＝Ｃ−Ｃ−０
＋Ｒ１−０−）−。ＨおよびＲ４−０＋Ｒ１−０＋ＩＴ
ｌＨ（Ｒ，Ｒｌ，Ｒ４，ｎ，ｍは前記と同じ）等が挙げ
られる。ＣＨ２＝Ｃ−Ｃ−０＋Ｒ１−０＋。Phosphate esters whose main component is a phosphoric ester represented by the general formula (1) used in the present invention (hereinafter referred to as the general formula (1)
The phosphoric acid esters represented by ) include those obtained by reacting alcohols with phosphoric anhydride. The reaction between the alcohol and phosphoric anhydride is carried out according to a known force method, and a polymerization inhibitor is used if necessary. As alcohols, CH2=C-C-0
+R1-0-)-. H and R4-0+R1-0+IT
lH (R, Rl, R4, n, m are the same as above), and the like. CH2=C-C-0+R1-0+.
Ｈとしては、例えばアクリル酸、メタアクリル酸にアル
キレンオキシドを１種もしくは２種以上付加させたもの
が挙げられる。アルキしンオキシドとしては、例えばエ
チレンオキシド、プロピレンオキシド、ブチレンオキシ
ド等が挙げられ、付加形態としてはランダム、プロツク
等が挙げられる。次にＲ４−０−（−Ｒ１−０分１１１
Ｈとしては、ブチルアルコール、ラウリルアルコール、
ドバ２．３アルコールおよびオレイルアルコールまたは
これらに前記アルキしンオキシドを１種もしくは２種以
上付加させたもの、またはｔ−ブチルフエノール、ノニ
ルフエノールおよびオクチルフエノールに前記アルキレ
ンオキシドを１種もしくは２種以上付加させたもの等が
挙げられる。Examples of H include acrylic acid and methacrylic acid to which one or more alkylene oxides are added. Examples of the alkyne oxide include ethylene oxide, propylene oxide, butylene oxide, etc., and examples of the addition form include random, block, etc. Then R4-0-(-R1-0 min 111
As H, butyl alcohol, lauryl alcohol,
Doba 2.3 alcohol and oleyl alcohol, or these to which one or more of the above alkylene oxides are added, or t-butylphenol, nonylphenol and octylphenol to which one or more of the above alkylene oxides are added. Examples include those that have been made.
無水リン酸としては通常の無水リン酸等が挙げられる。Examples of the phosphoric anhydride include ordinary phosphoric anhydride.
次にアルコール類と無水リン酸とを反応させる場合のモ
ル比は任意であり、好ましくはアルコール類／無水リン
酸二３／１〜１／１である。Next, when alcohols and phosphoric anhydride are reacted, the molar ratio is arbitrary, preferably alcohol/phosphoric anhydride 23/1 to 1/1.
またアルコール類としてはＣＨ２＝Ｃ−Ｃ−０＋Ｒ１−
０−）−ＮＨとＲ４−０＋Ｒ１−０−＋１１１Ｈとの混
合物を使用する場合、両者の混合割合は任意であり、好
ましくは得られる一般式（１）で表わされるリン酸エス
テル類のＣＨ２＝Ｃ−Ｃ−０そＲ１−０÷０Ｐ−Ｒ２と
Ｒ４−０−（−Ｒ１−０−＋ＩＴｌＰ−０−Ｒ３（Ｒ３
は前記と同じ）とがｌ／１以上となるように混合する。
次に本発明で得られる一般式（１）で表わされるリン酸
エステル類を添加剤として、熱硬化性樹脂に無機物を充
填して複合材料を得る場合に使用する。熱硬化性樹脂と
しては、例えばフエノール樹脂、エポキシ樹脂、アルキ
ツド樹脂、不飽和ポリエステル樹脂、尿素ホルムアルデ
ヒド樹脂、メラミン樹脂等が挙げられる。さらに、無機
物としては炭酸カルシウム、クレイ、カオリン、タルク
、石コウ、亜硫酸カルシウム、水酸化アルミニウム、水
酸化マグネシウム、酸化亜鉛、マイカ、石英粉、ベント
ナイト、ガラス繊維および従来公知の表面処理法で表面
処理された無機物等が挙けられる。Also, as alcohols, CH2=C-C-0+R1-
When a mixture of 0-)-NH and R4-0+R1-0-+111H is used, the mixing ratio of both is arbitrary, and preferably CH2=C of the phosphoric acid ester represented by the general formula (1) obtained. -C-0soR1-0÷0P-R2 and R4-0-(-R1-0-+ITlP-0-R3(R3
(same as above) are mixed in such a manner that the ratio of 1/1 or more is 1/1 or more.
Next, the phosphoric acid esters represented by the general formula (1) obtained in the present invention are used as additives when filling a thermosetting resin with an inorganic substance to obtain a composite material. Examples of thermosetting resins include phenolic resins, epoxy resins, alkyd resins, unsaturated polyester resins, urea formaldehyde resins, and melamine resins. In addition, inorganic materials include calcium carbonate, clay, kaolin, talc, gypsum, calcium sulfite, aluminum hydroxide, magnesium hydroxide, zinc oxide, mica, quartz powder, bentonite, glass fiber, and surface treatment using conventionally known surface treatment methods. Examples include inorganic substances.
本発明の添加剤の使用量は、無機物充填熱硬化性樹脂複
合材料において使用する無機物１００重量部に対する量
で、１〜５０重量部である。The amount of the additive used in the present invention is 1 to 50 parts by weight based on 100 parts by weight of the inorganic material used in the inorganic material-filled thermosetting resin composite material.
本発明の添加剤の使用力法としては熱硬化性樹脂一無機
物充填中に本発明の添加剤を使用するか、または熱硬化
性樹脂に充填する無機物をあらかじめ本発明の添加剤を
使用して被覆するかまたは単純に本発明の添加剤を熱硬
化性樹脂に配合したのち、次に無機物を分散させるよう
にして充填する等の力法等が挙げられる。本発明の添加
剤を使用した場合、熱硬化性樹脂への無機物充填時の粘
度降下作用が大きく、無機充填量が高く、加工性および
カツプリング特性に優れている等の特徴を示す。The method of using the additive of the present invention is to use the additive of the present invention while filling the thermosetting resin with the inorganic substance, or to use the additive of the present invention in advance of filling the inorganic substance into the thermosetting resin. Examples include force methods such as coating or simply blending the additive of the present invention into a thermosetting resin and then filling the resin with an inorganic substance to disperse it. When the additive of the present invention is used, it exhibits characteristics such as a large viscosity-lowering effect when filling a thermosetting resin with an inorganic substance, a high amount of inorganic filling, and excellent processability and coupling properties.
従つて、種々の特性を有する無機物充填熱硬化性樹脂複
合材料を提供することが可能となる。Therefore, it is possible to provide inorganic-filled thermosetting resin composite materials having various properties.
以下に本発明の実施例を記載する。実施例 １
（１）本願発明の添加剤の合成
アルコール類および無水リン酸を所定のモル比で、かつ
公知の力法に従つて反応させ、本願発明の添加剤を合成
した。Examples of the present invention are described below. Example 1 (1) Synthesis of the additive of the present invention The additive of the present invention was synthesized by reacting alcohols and phosphoric anhydride at a predetermined molar ratio according to a known force method.
それらを第１表に記載する。実施例 ２ 本発明の添加剤で、あらかじめ各種無機物を被覆した。They are listed in Table 1. Example 2 Various inorganic substances were coated in advance with the additive of the present invention.
本発明の添加剤の無機物への被覆は、ペンシェルミキサ
ー中常温で１０分間高速流動混合を行つた。それらを第
２表に記載する。The additive of the present invention was coated on the inorganic substance by high-speed fluid mixing for 10 minutes at room temperature in a pen shell mixer. They are listed in Table 2.
実施例 ３
実施例２で得た本発明の添加剤で被覆した無機物をエポ
キシ樹脂１００重量部に充填した。Example 3 The inorganic material coated with the additive of the present invention obtained in Example 2 was filled into 100 parts by weight of an epoxy resin.
Claims (1)
（ I ）（式中、ＲはＨもしくはＣＨ＿３−基、Ｒ＿１
は−ＣＨ＿２−ＣＨ＿２−基もしくは▲数式、化学式、
表等があります▼基もしくは▲数式、化学式、表等があ
ります▼基またはこれらの基の組み合せを表わし、Ｒ＿
２は−ＯＨ基もしくは▲数式、化学式、表等があります
▼もしくは−Ｏ−Ｒ＿３を表わし、Ｒ＿３は▲数式、化
学式、表等があります▼を表わし、Ｒ＿４は炭素数３〜
１８の飽和アルキル基もしくは炭素数３〜１８の不飽和
アルキル基もしくは炭素数１〜１２の飽和アルキルフェ
ノールの残基もしくは炭素数１〜１２の不飽和アルキル
フェノールの残基を表わす。 ｎは１〜５０の整数、ｍは０もしくは１〜５０の整数を
表わす。）で表わされるリン酸エステルを主成分とする
リン酸エステル類より成る無機物充填熱硬化性樹脂複合
材料用添加剤。[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
(I) (wherein R is H or CH_3- group, R_1
is -CH_2-CH_2- group or ▲ mathematical formula, chemical formula,
There are tables, etc. ▼ groups or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ groups or combinations of these groups, and R_
2 represents -OH group or ▲There is a mathematical formula, chemical formula, table, etc.▼ or -O-R_3, R_3 represents ▲There is a mathematical formula, chemical formula, table, etc.▼, and R_4 represents a carbon number of 3 to 3.
It represents a saturated alkyl group having 18 carbon atoms, an unsaturated alkyl group having 3 to 18 carbon atoms, a residue of a saturated alkylphenol having 1 to 12 carbon atoms, or a residue of an unsaturated alkylphenol having 1 to 12 carbon atoms. n represents an integer of 1 to 50, and m represents 0 or an integer of 1 to 50. ) An additive for inorganic-filled thermosetting resin composite materials consisting of phosphoric acid esters whose main component is a phosphoric ester represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8465181A JPS5917133B2 (en) | 1981-06-01 | 1981-06-01 | Additive for mineral-filled thermosetting resin composite materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8465181A JPS5917133B2 (en) | 1981-06-01 | 1981-06-01 | Additive for mineral-filled thermosetting resin composite materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57198735A JPS57198735A (en) | 1982-12-06 |
| JPS5917133B2 true JPS5917133B2 (en) | 1984-04-19 |
Family
ID=13836608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8465181A Expired JPS5917133B2 (en) | 1981-06-01 | 1981-06-01 | Additive for mineral-filled thermosetting resin composite materials |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5917133B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02190232A (en) * | 1989-01-20 | 1990-07-26 | Yamaha Motor Co Ltd | Conveyor system type machinery |
| JP2525598B2 (en) * | 1987-01-23 | 1996-08-21 | オ−ケ−−ビゼ キイ | Rotary pallet system |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59170130A (en) * | 1983-03-17 | 1984-09-26 | Daihachi Kagaku Kogyosho:Kk | Plastic or rubber magnet composition |
| JPS59170131A (en) * | 1983-03-17 | 1984-09-26 | Daihachi Kagaku Kogyosho:Kk | Surface-modified inorganic powder |
| FR2554119B1 (en) * | 1983-10-26 | 1986-01-24 | Omya Sa | CALCIUM CARBONATE TREATED FOR HIGHLY LOADED COMPOSITIONS OF THERMOSETTING OR THERMOPLASTIC RESINS |
| JP5681205B2 (en) * | 2009-12-17 | 2015-03-04 | スリーエム イノベイティブ プロパティズ カンパニー | Nano-calcite composite with high magnesium surface concentration |
-
1981
- 1981-06-01 JP JP8465181A patent/JPS5917133B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2525598B2 (en) * | 1987-01-23 | 1996-08-21 | オ−ケ−−ビゼ キイ | Rotary pallet system |
| JPH02190232A (en) * | 1989-01-20 | 1990-07-26 | Yamaha Motor Co Ltd | Conveyor system type machinery |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57198735A (en) | 1982-12-06 |
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