JPS6071625A - Production of polyurethane resin containing inorganic filler - Google Patents
Production of polyurethane resin containing inorganic fillerInfo
- Publication number
- JPS6071625A JPS6071625A JP58178171A JP17817183A JPS6071625A JP S6071625 A JPS6071625 A JP S6071625A JP 58178171 A JP58178171 A JP 58178171A JP 17817183 A JP17817183 A JP 17817183A JP S6071625 A JPS6071625 A JP S6071625A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane resin
- inorganic filler
- hydrocarbon group
- parts
- inorganic
- 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
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- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、無機物充填ポリウレタン系樹脂の製造方法に
関し、特に無機物充填剤を多量に含有しても粘度が低く
、しかも樹脂硬化物の熱安定性が改善された無機物充填
ポリウレタン系樹脂の製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing an inorganic-filled polyurethane resin, and in particular, an inorganic-filled polyurethane resin that has low viscosity even when containing a large amount of inorganic filler, and has improved thermal stability of the cured resin. The present invention relates to a method for producing polyurethane resin.
シール剤、塗料、接着剤等に無機物充填ポリウレタン系
樹脂が使用されている。無機物充填ポリウレタン系樹脂
は、インシアネート成分中のNCO基が反応性に富むた
め、通常は、より安定なポリオール成分に無機充填剤を
添加混合した後でイソシアネート成分を混合し、反応せ
しめて得られる。Inorganic-filled polyurethane resins are used in sealants, paints, adhesives, etc. Inorganic-filled polyurethane resins are usually obtained by adding and mixing an inorganic filler to a more stable polyol component, then mixing the isocyanate component and reacting, because the NCO group in the inocyanate component is highly reactive. .
しかし、ポリオール成分に無機充填剤を多j(1に混合
する場合、混合系の粘度が無機充填剤の高充填で非常に
高くなるため、作画性に極めて困かII′を来す。また
、一般にポリウレタン樹脂は熱安定性に欠点があシ、従
って無機物充填ポリウレタン樹脂1例外ではなく、特に
熱による硬度の低下が著るしく大きい。However, when mixing a polyol component with an inorganic filler in a large amount, the viscosity of the mixed system becomes extremely high due to the high amount of inorganic filler, which causes extremely difficult drawing performance.Also, Generally, polyurethane resins have a drawback in thermal stability, and therefore, mineral-filled polyurethane resins are no exception, and in particular, the decrease in hardness due to heat is significantly large.
本発明は、上記の問題点に鑑みてなされたものであって
、無機充填剤を高充填しても、粘度上昇が少く、さらに
硬化して得られた樹脂の熱安定性が改善された無機物充
填ポリウレタン#を脂の製造方法を提供することを目的
とするものである。The present invention has been made in view of the above-mentioned problems, and is an inorganic material that exhibits little increase in viscosity even when filled with an inorganic filler at a high level, and further improves the thermal stability of the resin obtained by curing. The purpose is to provide a method for producing filled polyurethane resin.
定の有機チタネート化合物を添加することにより、上記
の目的が達成されることを見い出し、本発明を完成する
に至った。It has been discovered that the above object can be achieved by adding a certain organic titanate compound, and the present invention has been completed.
す々わち、本発明は、ポリオール成分とイソシアネート
成分および無機充填剤から無機物充填ポリウレタン系樹
脂を製造するに際し、無機充填剤100重邦部に対して
01ないし5重量部の下記一般式〔1〕で示される有機
チタネート化合物を添加すること全特徴とする無機物充
填ポリウレタン系樹脂の製造方法である。That is, the present invention provides a method for producing an inorganic-filled polyurethane resin from a polyol component, an isocyanate component, and an inorganic filler, by adding 0.1 to 5 parts by weight of the following general formula [1] to 100 parts by weight of the inorganic filler. ] This is a method for producing an inorganic-filled polyurethane resin, which is characterized by the addition of an organic titanate compound shown in the following.
Ti(OR)x(OCOR’)Y(OCOR′′NH2
)z ・・+・+++++ CI)(式中、Rは炭素数
3ないし8の1価の炭化水素基、R′は炭素数1ないし
18の1価の炭化水素基、R“は炭素数1ないし8の2
価の炭化水素基であり、xyzは1ないし2、X+Y+
Z=4である。)
本発明におけるポリオール成分とは、ポリウレタン樹脂
の原料として使用される各種ポリオール、例えばポリエ
ーテルポリオール、ポリエステルポリオールあるいはポ
リアクリルポリオールであり、これらポリオールの分子
量は特に限定されるものではない。Ti(OR)x(OCOR')Y(OCOR''NH2
)z ・・+・+++++ CI) (In the formula, R is a monovalent hydrocarbon group having 3 to 8 carbon atoms, R' is a monovalent hydrocarbon group having 1 to 18 carbon atoms, and R" is a monovalent hydrocarbon group having 1 to 18 carbon atoms. or 8-2
is a valent hydrocarbon group, xyz is 1 to 2, X+Y+
Z=4. ) The polyol component in the present invention refers to various polyols used as raw materials for polyurethane resins, such as polyether polyols, polyester polyols, and polyacrylic polyols, and the molecular weight of these polyols is not particularly limited.
インシアネート成分としては、ポリウレタン樹脂の原料
として従来公知のものを広く使用することができ、例え
ば芳香族系、脂肪族系、脂環族系のイソシアネート、さ
らにはプレポリマー化したインシアネート等であり、具
体的には例えはトリレンジインシアネート、4.4−ジ
フェニルメタンジイソシアネート、ナフタレンジイソシ
アネート、キンリレ/ジインシアネート、ビス(イソシ
アネートメチル)シクロヘキサン、ジシクロヘキシルメ
タンジイソシアネート、ヘキサメチレンジイソシアネー
ト、リジンジイソシアネート、イソホロンジイソシアネ
ート等が挙げられ、また活性水駆を有する官能基を複数
個有する低級多官能化合物と上記のジイソシアネートを
反応してKOられるウレタンプレポリマー等が用いられ
る。As the incyanate component, a wide range of materials conventionally known as raw materials for polyurethane resins can be used, such as aromatic, aliphatic, and alicyclic isocyanates, and even prepolymerized incyanates. , Specific examples include tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, naphthalene diisocyanate, quinrille/diincyanate, bis(isocyanatemethyl)cyclohexane, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, etc. Also used are urethane prepolymers which can be KOed by reacting a lower polyfunctional compound having a plurality of functional groups having active hydration with the above-mentioned diisocyanate.
無機物充填剤としては、これを使用する目的により種々
のものが使用されるが、例えば増量剤として、高充填し
て用いられる金属、金属酸化物、炭酸カルシュム、タル
ク、クレー、カーボンブラック、ウオラストナイト等で
ある。Various inorganic fillers are used depending on the purpose for which it is used, such as metals, metal oxides, calcium carbonate, talc, clay, carbon black, and wolast, which are used in high fillers as fillers. Knight et al.
本発明における一般式〔1〕の有機チタネート化合物は
、Ti (OR)x (OCOR’ )y (OCOR
′′NH2)zで表され、但し、式中Rは炭素数3ない
し8の1価の炭化水素基、R″は炭素数1ないし18の
1価の炭化水素基、R′−は炭素数1ないし8の2価の
炭化水素基であり、xyzは1ないし2、x+y十Z=
4である。The organic titanate compound of general formula [1] in the present invention is Ti (OR) x (OCOR' ) y (OCOR
''NH2)z, where R is a monovalent hydrocarbon group having 3 to 8 carbon atoms, R'' is a monovalent hydrocarbon group having 1 to 18 carbon atoms, and R'- is a carbon number 1 to 8 divalent hydrocarbon group, xyz is 1 to 2, x+y+Z=
It is 4.
ここで言うRの炭素数3ないし8の1価の炭化水素基と
しては、アルキル基、アルケニル基、アリール基等であ
シ、R′の炭素数1ないし18の1価の炭化水素基とし
ては、アルキル基、アルケニル基、アリール基管であり
、R“の炭素数1ないし8の2価の炭化水素基としては
、アルキレン基、了り−レン基等である。具体的な例と
して、T i (OC3H7) (OCOCH=CH2
)2 (OCO(CH2)5NH2)Ti (QC3H
7) (OCOC□7H3s )2 (OCO(CH2
)5 NI2 :)Ti(OC3H7)(OCO@)2
〔0CO(CII2)5NH2〕Ti (QC3H7)
(OCOC□7H35) C0CO(CH2)5NH
2’12T 1 (OC3H7) (OCOCR”CH
2) (OCOC17H35)(OCO(CH2) 5
NI2 )
Ti(OC4H9) (OCOC17H35)2 (O
CO(CH2)5NH2)T i (OC4H9) 2
(OCOC□7H35) (OCO(CH2)5NH
2)T i (OCsH17)2 (OCOC17Ha
s ) (OCO(CH2) 5 NI(2)T i
(OCH2CH”CH2) (OCOC,H2S )2
(OCO(CH2) 5 NI2 〕Ti (QC6
H5) (OCOC□7H3,)2 (0CO(CH2
)5NH21)等が挙げられる。The monovalent hydrocarbon group having 3 to 8 carbon atoms for R herein may be an alkyl group, alkenyl group, aryl group, etc., and the monovalent hydrocarbon group having 1 to 18 carbon atoms for R' may include an alkyl group, an alkenyl group, an aryl group, etc. , an alkyl group, an alkenyl group, an aryl group, and a divalent hydrocarbon group having 1 to 8 carbon atoms for R'' includes an alkylene group, an iri-lene group, etc. As a specific example, T i (OC3H7) (OCOCH=CH2
)2 (OCO(CH2)5NH2)Ti (QC3H
7) (OCOC□7H3s )2 (OCO(CH2
)5 NI2 :)Ti(OC3H7)(OCO@)2
[0CO(CII2)5NH2]Ti (QC3H7)
(OCOC□7H35) C0CO(CH2)5NH
2'12T 1 (OC3H7) (OCOCR"CH
2) (OCOC17H35) (OCO(CH2) 5
NI2) Ti(OC4H9) (OCOC17H35)2 (O
CO(CH2)5NH2)T i (OC4H9) 2
(OCOC□7H35) (OCO(CH2)5NH
2) T i (OCsH17)2 (OCOC17Ha
s ) (OCO(CH2) 5 NI(2)T i
(OCH2CH”CH2) (OCOC,H2S)2
(OCO(CH2) 5 NI2 ]Ti (QC6
H5) (OCOC□7H3,)2 (0CO(CH2
)5NH21) and the like.
これらの有機チタネート化合物は、1’l (OR)4
にR’C0OHとH2NR″C00IIを反応させるこ
とにより容易に得ることができる。These organotitanate compounds are 1'l (OR)4
It can be easily obtained by reacting R'C0OH with H2NR''C00II.
これらの有機チタネート化合物は単独あるいは二種以上
の混合物としても有効で、ポリオール成分に予め加えて
おいてもよいし、ポリオール成分に無機充填剤を混合す
る時に同時に加えてもよく、また無機充填剤の表面に予
め、コーティング処理しておいてもよく、特にその添加
方法は限定されるものではない。These organic titanate compounds are effective alone or as a mixture of two or more, and may be added to the polyol component in advance, or may be added simultaneously when mixing the inorganic filler with the polyol component, or may be added to the polyol component at the same time as the inorganic filler. The surface of the compound may be coated in advance, and the method of adding the compound is not particularly limited.
とれらの有機チタネート化合物の添加量は無機充填剤1
00重量部に対して0.1ないし5重量部、好ましくは
05〜2重量部である。01重量部以下ではその効果は
小さく、また5重量部以上加えても効果の増加は認めら
れ力い。Tora's organic titanate compound is added in an amount equal to 1 inorganic filler.
The amount is from 0.1 to 5 parts by weight, preferably from 0.5 to 2 parts by weight. If the amount is less than 0.01 parts by weight, the effect is small, and even if it is added in amounts of 5 parts by weight or more, no increase in the effect is observed.
本発明においては、その他に必製に応じ、触媒、架橋剤
、鎖延長剤、着色剤等の各種添加剤を使用してもよい。In the present invention, various other additives such as a catalyst, a crosslinking agent, a chain extender, and a coloring agent may be used as required.
本発明の方法によれは、無機物充填ポリウレタン樹脂の
製造に際し、一般式CI)で示される有機チタネート化
合物を少量添加することにより、作挙性が著しく改善さ
れ、さらに熱安定性の改善された無機物充填ポリウレタ
ン樹脂を得ることが出来る。従って本発明は、シール剤
、塗料、接着剤、車両部品等に使用される無機物充填ポ
リウレタン系樹脂の製造に極めて有効である。According to the method of the present invention, by adding a small amount of an organic titanate compound represented by the general formula CI) during the production of an inorganic-filled polyurethane resin, the workability is significantly improved, and the inorganic material is further improved in thermal stability. A filled polyurethane resin can be obtained. Therefore, the present invention is extremely effective for producing inorganic-filled polyurethane resins used in sealants, paints, adhesives, vehicle parts, and the like.
以下、本発明を実施例、比較例によシ具体的に説明する
が、本発明はこれら実施例にのみ限定されるものではな
い。なお例中の部およびチは重量部および重量%を示す
。EXAMPLES The present invention will be specifically explained below using Examples and Comparative Examples, but the present invention is not limited only to these Examples. Note that parts and parts in the examples indicate parts by weight and weight %.
実施例1〜5、比較例1
ポリエーテルポリオールNK−3050K(三井日曹ウ
レタンG→、商品名)に表−1の配合で、先ずエチレン
グリコール、ジブチルスズジラウレートを混合し、次い
で有史チタネート化合物(1)でろるTi (QC3H
7) (OCOC1□H35)2(OCOC6H4NH
2)(以下、化イ)物(I−1)と称す。)を添加混合
し、さらに無((゛を充填剤として炭酸カルシウム(白
石工票GM 製)を添加混合した。Examples 1 to 5, Comparative Example 1 Polyether polyol NK-3050K (Mitsui Nisso Urethane G→, trade name) was first mixed with ethylene glycol and dibutyltin dilaurate in the formulation shown in Table 1, and then a historic titanate compound (1 ) Deroru Ti (QC3H
7) (OCOC1□H35)2(OCOC6H4NH
2) (hereinafter referred to as compound (I)). ) was added and mixed, and calcium carbonate (manufactured by Shiroishi Koshou GM) was further added and mixed with (2) as a filler.
このようにして得られた混合物の粘度測定をなし、その
結果を表−1に示す。また、化合物〔1−1〕の添加し
ない混合系についても粘度測定を行い、比較例工として
その結果を表−1に示す。The viscosity of the mixture thus obtained was measured and the results are shown in Table 1. The viscosity was also measured for the mixed system without addition of compound [1-1], and the results are shown in Table 1 as a comparative example.
実施例6、比較例2
ポリエーテルポリオールDial−3000(三井日曹
つレタン■製、商品名)100部に、先ずジオクチルフ
タレート30部を混合し、次いで有機チタネート化合物
(1)であるTi (OC3H7) (OCO17H3
5)2 (OCO(CH2)5NH2) (以下、化合
物(1−2,1と称す。)0.6部を添加混合し、さら
に炭酸カルシウム(111出)60部を添加混合した。Example 6, Comparative Example 2 First, 30 parts of dioctyl phthalate was mixed with 100 parts of polyether polyol Dial-3000 (manufactured by Mitsui Nisso Tsuretan, trade name), and then Ti (OC3H7), which is an organic titanate compound (1), was mixed with 30 parts of dioctyl phthalate. ) (OCO17H3
5) 0.6 part of 2 (OCO(CH2)5NH2) (hereinafter referred to as compound (1-2,1)) was added and mixed, and further 60 parts of calcium carbonate (ex. 111) was added and mixed.
このようにして得られた混合物の粘度測定をなし、その
結果を表−2に示す。まだ、化合物〔1−2〕を添加し
ない混合系についても粘度測定を行い、比較例2として
その結果を表−2に示す。The viscosity of the mixture thus obtained was measured and the results are shown in Table 2. The viscosity of the mixed system without addition of compound [1-2] was also measured, and the results are shown in Table 2 as Comparative Example 2.
実施例7
実施例6において、化合物[:l−2) 066部の代
わりにTi (QC3H7) (OCOC,7Hあ)
(OCO(CH2)5NII2 )2 (以下、化合物
(1−3)と称す。)を06部を用いた以外は実施例6
と全く同様に行った。結果を表−2に示す。Example 7 In Example 6, Ti (QC3H7) (OCOC,7Ha) was used instead of 066 parts of the compound [:l-2).
Example 6 except that 06 parts of (OCO(CH2)5NII2)2 (hereinafter referred to as compound (1-3)) was used.
I did exactly the same thing. The results are shown in Table-2.
実施例8
実施例6において、化合物(1−2)0.6部の代わり
にTi (OC3H7) (0COC(C)la) =
CH2)2 C0CO(CH2)sNH2) (以下、
化合物(1−4)と称す。)を06部を用いた以外は実
施例6と全く同様に行った。Example 8 In Example 6, Ti (OC3H7) (0COC(C)la) = instead of 0.6 part of compound (1-2)
CH2)2 C0CO(CH2)sNH2) (hereinafter,
It is called compound (1-4). ) was carried out in exactly the same manner as in Example 6 except that 06 parts of the sample were used.
結果を表−2に示す。The results are shown in Table-2.
比較例3
実施例6において、化合物(1−2)0.6部の代わり
に市販有機チタネート化合物のTi (OC3fI7)
(ococmTH&l)306部を用いた以外は実施
例6と全く同様に行つた。結果を表−2に示す。Comparative Example 3 In Example 6, Ti (OC3fI7), a commercially available organic titanate compound, was used instead of 0.6 part of compound (1-2).
The same procedure as in Example 6 was carried out except that 306 parts of (ococmTH&l) was used. The results are shown in Table-2.
比較例4
実施例6において、化合物(1−2)0.6部の代わり
に市販有機チタネート化合物のT i (OCaHy)
C0CO(CH2)5NH2)3を0.6部を用いた
以外は実施例6と全く同様に行った結果を表−2に示す
。なお、ここで用いた有機チクネート化合物は粉末状で
混合分散が極めて困難であった。Comparative Example 4 In Example 6, T i (OCaHy), a commercially available organic titanate compound, was used instead of 0.6 part of compound (1-2).
Table 2 shows the results obtained in exactly the same manner as in Example 6 except that 0.6 part of COCO(CH2)5NH2)3 was used. The organic chicknate compound used here was in powder form and was extremely difficult to mix and disperse.
表−2
プこ施例9〜11、比較例5
実施例2〜4で得られた各々の混合物にイソシアネート
成分としてMDI −LK (三井日曹ウレタン1η製
、商品名)をNCO10H= 1.05になるように加
え、室温で混合した後、モールドに流し込んで120℃
で2時間硬化させた。さらに100℃で4日間熱処理を
行い、熱処理前後の硬度をIt!lI定した。結果を表
−3に示す。Table 2 Examples 9 to 11, Comparative Example 5 MDI-LK (manufactured by Mitsui Nisso Urethane 1η, trade name) was added as an isocyanate component to each of the mixtures obtained in Examples 2 to 4 with NCO10H = 1.05. After mixing at room temperature, pour into a mold and heat at 120℃.
It was cured for 2 hours. Furthermore, heat treatment was performed at 100℃ for 4 days, and the hardness before and after heat treatment was It! II was determined. The results are shown in Table-3.
まだ、比較例1で得られた混合物についても同様に試験
を行い、比較例5としてその結果を表−3に示す。The mixture obtained in Comparative Example 1 was also tested in the same manner, and the results are shown in Table 3 as Comparative Example 5.
実施例12、比較例6
ポリエーテルポリオールEP−330C(三井日曹つレ
タン■製、商品名)200部に、先ずエチレングリコー
ル25部、ジブチルスズジラウレート0.2部、ジオク
チルフタレート60部を混合し、次いで有機チタネート
化合物として前記の化合物(1−2)を1.2部を添加
混合し、さらに炭酸カルシウム(前出)120部を混合
した。次に、この混合物にインシアネート成分としてM
DI −LK (前出)31.6部CNCO10I(=
1.05 )を加え、室温で混合した後、モールドに
流し込んで120℃で2時間硬化させた。さらに100
℃で4日間熱処理を行い、熱処理前後の硬度を測定した
。結果を表−4に示す。Example 12, Comparative Example 6 First, 25 parts of ethylene glycol, 0.2 parts of dibutyltin dilaurate, and 60 parts of dioctyl phthalate were mixed into 200 parts of polyether polyol EP-330C (manufactured by Mitsui Nisso Tsuretan ■, trade name). Next, 1.2 parts of the above compound (1-2) as an organic titanate compound were added and mixed, and further 120 parts of calcium carbonate (described above) were mixed therein. Next, M as an incyanate component was added to this mixture.
DI -LK (previously) 31.6 parts CNCO10I (=
1.05) was added and mixed at room temperature, then poured into a mold and cured at 120°C for 2 hours. 100 more
Heat treatment was performed at ℃ for 4 days, and the hardness before and after the heat treatment was measured. The results are shown in Table 4.
また、上記化合物(1−2)を添加しない系について同
様に試験を行い、比較例6<!:してその結果を表−4
に示す。In addition, a similar test was conducted on a system in which the above compound (1-2) was not added, and Comparative Example 6<! :The results are shown in Table-4.
Shown below.
実施例13
実施例12において、化合物(1−2)1.2部の代わ
りに前記化合物(1−4)を1.2部用いた以外は実施
例12と全く同様に行った。結果を表−4に示す。Example 13 The same procedure as in Example 12 was conducted except that 1.2 parts of the compound (1-4) was used instead of 1.2 parts of the compound (1-2). The results are shown in Table 4.
表−4
手続補正書
昭和58年1り月/ン 口
昭和58年特許願第178171号
2、発明の名称
無機物充填ポリウレタン系樹脂の製造方法3、補正する
者
事件との関係 特許出願人
[相]100東京都千代田区大手町二丁目2番1号(4
30)日本曹達株式会社
代表者 −三 宮 武 夫
4、代理人
■100東京都千代田区大手町二丁目2番1号日本曹達
株式会社内
電話 (245)6234
6、補正の内容
(1)明細書の第5頁第8行目のrR″JをrR’Jに
訂正する。Table-4 Procedural amendment filed in January 1982 Patent Application No. 178171 2, Title of invention Method for producing inorganic-filled polyurethane resin 3, Relationship with the person making the amendment Patent applicant [companion] ] 100 2-2-1 Otemachi, Chiyoda-ku, Tokyo (4
30) Representative of Nippon Soda Co., Ltd. - Takeo Sannomiya 4, Agent ■ 100 2-2-1 Otemachi, Chiyoda-ku, Tokyo Nippon Soda Co., Ltd. Phone: (245) 6234 6. Contents of the amendment (1) Details Correct rR''J on page 5, line 8 of the book to rR'J.
(2) 同 第8頁第3行目のrNK−3050KJを
rMN−3050KJに訂正する。(2) Correct rNK-3050KJ in the third line of page 8 to rMN-3050KJ.
Claims (1)
充填剤から無機物充填ポリウレタン系樹脂を製造するに
際し、無機充填剤100重量部に対して01ないし5重
度部の下記一般式〔1〕で示される有機チタネート化合
物を添加することを特徴とする無機物充填ポリウレタン
系樹脂の製造方法。 Ti (OR)x (OCOR′)y (OCOR″N
H2)z −C1”J(式中、Rは炭素数3ないし8の
1価の炭化水素基、R’は炭素数1ないし18の1価の
炭化水素基、R//は炭素数1ないし8の2価の炭化水
素基であり、xyzは1ないし2、X+Y+Z=4であ
る。)(1) When producing an inorganic-filled polyurethane resin from a polyol component, an incyanate component, and an inorganic filler, an organic titanate represented by the following general formula [1] in an amount of 01 to 5 parts by weight per 100 parts by weight of the inorganic filler is used. A method for producing an inorganic-filled polyurethane resin, which comprises adding a compound. Ti (OR)x (OCOR′)y (OCOR″N
H2)z -C1''J (wherein, R is a monovalent hydrocarbon group having 3 to 8 carbon atoms, R' is a monovalent hydrocarbon group having 1 to 18 carbon atoms, and R// is a monovalent hydrocarbon group having 1 to 18 carbon atoms. 8 divalent hydrocarbon group, xyz is 1 to 2, and X+Y+Z=4.)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58178171A JPS6071625A (en) | 1983-09-28 | 1983-09-28 | Production of polyurethane resin containing inorganic filler |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58178171A JPS6071625A (en) | 1983-09-28 | 1983-09-28 | Production of polyurethane resin containing inorganic filler |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6071625A true JPS6071625A (en) | 1985-04-23 |
Family
ID=16043848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58178171A Pending JPS6071625A (en) | 1983-09-28 | 1983-09-28 | Production of polyurethane resin containing inorganic filler |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6071625A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012003843A1 (en) | 2010-07-05 | 2012-01-12 | Holger Blum | Polyurethane coating agent |
JP2015166404A (en) * | 2014-03-03 | 2015-09-24 | 東ソー株式会社 | Two-component polyurethane adhesive, laminate obtained by using the same, and protective sheet for solar cell |
CN113646351A (en) * | 2019-02-25 | 2021-11-12 | 汉高知识产权控股有限责任公司 | Thermal interface materials based on two-part polyurethanes |
-
1983
- 1983-09-28 JP JP58178171A patent/JPS6071625A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012003843A1 (en) | 2010-07-05 | 2012-01-12 | Holger Blum | Polyurethane coating agent |
US9266992B2 (en) | 2010-07-05 | 2016-02-23 | Holger Blum | Polyurethane coating agent |
JP2015166404A (en) * | 2014-03-03 | 2015-09-24 | 東ソー株式会社 | Two-component polyurethane adhesive, laminate obtained by using the same, and protective sheet for solar cell |
CN113646351A (en) * | 2019-02-25 | 2021-11-12 | 汉高知识产权控股有限责任公司 | Thermal interface materials based on two-part polyurethanes |
CN113646351B (en) * | 2019-02-25 | 2023-11-21 | 汉高股份有限及两合公司 | Thermal interface material based on two-part polyurethane |
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