JPH05345871A - Curing agent composition - Google Patents
Curing agent compositionInfo
- Publication number
- JPH05345871A JPH05345871A JP4181845A JP18184592A JPH05345871A JP H05345871 A JPH05345871 A JP H05345871A JP 4181845 A JP4181845 A JP 4181845A JP 18184592 A JP18184592 A JP 18184592A JP H05345871 A JPH05345871 A JP H05345871A
- Authority
- JP
- Japan
- Prior art keywords
- curing agent
- agent composition
- weight
- composition
- storage stability
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 7
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- -1 ester compound Chemical class 0.000 claims description 3
- 238000000576 coating method Methods 0.000 abstract description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000006185 dispersion Substances 0.000 abstract 1
- 229960005088 urethane Drugs 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、特に貯蔵安定性に優
れ、しかも非常に使用しやすく、塗膜性能のバラツキが
少ないアクリル系ウレタン塗料用硬化剤組成物に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a curing agent composition for acrylic urethane coatings, which has excellent storage stability, is very easy to use, and has little variation in coating film performance.
【０００２】[0002]
【従来の技術及びその課題】従来、自動車の補修や、産
業機械、建造物、構築物、家具等の塗装、補修に、アク
リル系ウレタン塗料が主に使用されている。2. Description of the Related Art Conventionally, acrylic urethane paints have been mainly used for repairing automobiles, painting and repairing industrial machines, buildings, structures, furniture and the like.
【０００３】この場合、硬化剤としてポリイソシアネー
ト化合物を不揮発分として６０〜８０重量％含有するも
のが、塗料使用時にアクリルポリオールのベース塗料１
００重量％に対して１０重量％混合され、さらに塗装粘
度になるようにシンナーで希釈されて使用される。In this case, a polyisocyanate compound as a curing agent containing 60 to 80% by weight as a non-volatile component is an acrylic polyol base paint 1 when the paint is used.
10% by weight is mixed with 00% by weight, and further diluted with thinner to obtain a coating viscosity and used.
【０００４】しかしこの場合、ベース塗料重量及び硬化
剤重量を計量器にて計量して添加されずに目分量で添加
されるのが通常である。そのため、ベース塗料中のポリ
オール成分のＯＨ当量と硬化剤成分のＮＣＯ当量の比率
が大幅にずれ、十分な塗膜性能が得られなかったり、ま
た、ベース塗料、硬化剤、シンナーの３液型であるため
作業が非常に煩雑になるという問題点があった。In this case, however, the weight of the base paint and the weight of the curing agent are not measured and added by a measuring instrument, but they are usually added in a proper amount. Therefore, the ratio of the OH equivalent of the polyol component and the NCO equivalent of the curing agent component in the base coating material is significantly different, and sufficient coating performance cannot be obtained. Therefore, there is a problem that the work becomes very complicated.
【０００５】３液型を２液型にするため、硬化剤成分と
シンナーとを一緒にした組成物を考えることもできる
が、このような混合物を缶中に入れ、使用時に蓋を開け
て使用した場合、開放時の溶剤揮発により缶中に空気中
の水分が凝結し、硬化剤組成中のイソシアネートと反応
するために非常に貯蔵安定性が悪く使用できない。It is possible to consider a composition in which a curing agent component and a thinner are combined in order to change the three-pack type to the two-pack type, but such a mixture is put in a can and the lid is opened before use. In this case, water in the air is condensed in the can by volatilization of the solvent at the time of opening and reacts with the isocyanate in the curing agent composition, so that the storage stability is very poor and it cannot be used.
【０００６】[0006]
【課題を解決するための手段】そこで本発明者らは、貯
蔵安定性に優れ、しかも非常に使用しやすく、塗膜性能
のバラツキが少ないアクリル系ウレタン塗料用硬化剤組
成物を得るべく鋭意検討した結果、ポリイソシアネート
化合物、脱水剤及び有機溶剤を含有する組成物が上記問
題点を解決できることを見出し本発明を完成するに至っ
た。[Means for Solving the Problems] Therefore, the present inventors diligently studied to obtain a curing agent composition for an acrylic urethane coating which has excellent storage stability, is very easy to use, and has little variation in coating film performance. As a result, they have found that a composition containing a polyisocyanate compound, a dehydrating agent and an organic solvent can solve the above problems, and have completed the present invention.
【０００７】すなわち、本発明は、ポリイソシアネート
化合物を１〜４０重量％、脱水剤を０．１〜５．０重量
％及び有機溶剤を５５〜９８．９重量％含むことを特徴
とする硬化剤組成物を提供するものである。That is, the present invention contains 1 to 40% by weight of a polyisocyanate compound, 0.1 to 5.0% by weight of a dehydrating agent, and 55 to 98.9% by weight of an organic solvent. A composition is provided.
【０００８】以下、本発明組成物について具体的に説明
する。本発明組成物に使用し得るポリイソシアネート化
合物としては特に制限はないが、例えば、ヘキサメチレ
ンジイソシアネートもしくはトリメチルヘキサメチレン
ジイソシアネートの如き脂肪族ジイソシアネート類；水
素添加キシリレンジイソシアネートもしくはイソホロン
ジイソシアネートの如き脂環式ジイソシアネート類；ト
リレンジイソシアネートもしくは４，４´−ジフェニル
メタンジイソシアネートの如き芳香族ジイソシアネート
類等の有機ジイソシアネートそれ自体、またはこれらの
各有機ジイソシアネートと多価アルコール、低分子量ポ
リエステル樹脂もしくは水等との付加物、あるいは上記
した如き各有機ジイソシアネート同志の環状重合体、更
にはイソシアネートビウレット体等が挙げられる。これ
らの代表的な市販品の例としては、デュラネート２４
Ａ、デュラネートＴＰＡ−１００（以上、旭化成工業
（株）製品）、スミジュールＮ−３５００、スミジュー
ルＮ、スミジュールＺ−４３７０（以上、住友バイエル
ウレタン（株）製品）、バーノックＤ−７５０、バーノ
ック８００、バーノックＤＮ−９５０（以上、大日本イ
ンキ化学工業（株）製品）、タケネートＤ−１０２、タ
ケネート１４０Ｎ（以上、武田薬品工業（株）製品）等
が挙げられる。The composition of the present invention will be specifically described below. The polyisocyanate compound that can be used in the composition of the present invention is not particularly limited, and examples thereof include aliphatic diisocyanates such as hexamethylene diisocyanate or trimethylhexamethylene diisocyanate; Organic diisocyanates themselves such as aromatic diisocyanates such as tolylene diisocyanate or 4,4′-diphenylmethane diisocyanate, or adducts of each of these organic diisocyanates with polyhydric alcohols, low molecular weight polyester resins or water, or Examples include cyclic polymers of the same organic diisocyanate as described above, and further isocyanate biuret. Examples of these representative commercial products include Duranate 24
A, Duranate TPA-100 (above, product of Asahi Kasei Co., Ltd.), Sumidule N-3500, Sumidule N, Sumidule Z-4370 (above, Sumitomo Bayer Urethane Co., Ltd. product), Barnock D-750, Barnock 800, Burnock DN-950 (above, product of Dainippon Ink and Chemicals, Inc.), Takenate D-102, Takenate 140N (above, product of Takeda Pharmaceutical Co., Ltd.) and the like.
【０００９】本発明組成物に使用し得る脱水剤として
は、加水分解性エステル化合物が好適である。例えば、
オルトギ酸メチル、オルトギ酸エチル、オルト酢酸メチ
ル、オルト酢酸エチルなどが挙げられる。As the dehydrating agent which can be used in the composition of the present invention, a hydrolyzable ester compound is suitable. For example,
Methyl orthoformate, ethyl orthoformate, methyl orthoacetate, ethyl orthoacetate and the like can be mentioned.
【００１０】本発明組成物において、脱水剤の配合量は
０．１〜５．０重量％の範囲である。０．１重量％より
少ないと脱水効果が不十分で貯蔵安定性が悪く、５．０
重量％を超えて使用された場合、コストが高くなる。In the composition of the present invention, the content of the dehydrating agent is in the range of 0.1 to 5.0% by weight. If the amount is less than 0.1% by weight, the dehydration effect is insufficient and the storage stability is poor, and 5.0
If used in excess of weight%, the cost will be high.
【００１１】本発明組成物に使用し得る有機溶剤として
は、イソシアネート基と反応する官能基を含有せず、ポ
リイソシアネート化合物及び脱水剤を溶解できるもので
あれば何でもよい。例えば、トルエン、キシレン等の芳
香族炭化水素；アセトン、メチルエチルケトン等のケト
ン類；酢酸エチル、酢酸ブチル等のエステル類等が挙げ
られる。これらの溶剤は単独で、又は２種以上を混合し
て用いてもよい。Any organic solvent can be used in the composition of the present invention as long as it does not contain a functional group that reacts with an isocyanate group and can dissolve the polyisocyanate compound and the dehydrating agent. Examples thereof include aromatic hydrocarbons such as toluene and xylene; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate. You may use these solvent individually or in mixture of 2 or more types.
【００１２】本発明組成物は、貯蔵安定性に優れ、また
使用時にも空気中の水分の影響が少ないため、アクリル
系ウレタン塗料の硬化剤として使用した場合、非常に使
用しやすく、塗膜性能のバラツキが少ない。従って、本
発明組成物は、自動車の補修や、産業機械、建造物、構
築物、家具等の塗装、補修にアクリル系ウレタン塗料の
硬化剤として好適に使用できる。Since the composition of the present invention has excellent storage stability and is less affected by moisture in the air during use, it is very easy to use when used as a curing agent for acrylic urethane paints, and the coating film performance is improved. Variation is small. Therefore, the composition of the present invention can be suitably used as a curing agent for acrylic urethane paints for repairing automobiles, painting and repairing industrial machines, buildings, structures, furniture and the like.
【００１３】[0013]
【実施例】以下、実施例により本発明を具体的に説明す
る。なお、特に断わらないかぎり、部は重量基準であ
る。EXAMPLES The present invention will be specifically described below with reference to examples. In addition, unless otherwise specified, all parts are by weight.
【００１４】実施例１ デュラネートＴＰＡ−１００（ヘキサメチレンジイソシ
アネート、旭化成工業（株）製品）３０部をトルエン２
９．５部、キシレン３０部、酢酸ブチル１０部からなる
混合溶剤６９．５部に溶解し、脱水剤としてオルトギ酸
メチル０．５部を添加して硬化剤組成物を作成した。こ
れを密閉状態で４０℃、１ケ月保存したものと、開放状
態で２５℃、７日間保存したものについて貯蔵安定性を
評価した。結果を表１に示した。Example 1 30 parts of Duranate TPA-100 (hexamethylene diisocyanate, a product of Asahi Kasei Co., Ltd.) was mixed with 2 parts of toluene.
It was dissolved in 69.5 parts of a mixed solvent consisting of 9.5 parts, 30 parts of xylene and 10 parts of butyl acetate, and 0.5 part of methyl orthoformate was added as a dehydrating agent to prepare a curing agent composition. The storage stability was evaluated for one that was stored in a sealed state at 40 ° C for 1 month and one that was stored in an open state at 25 ° C for 7 days. The results are shown in Table 1.
【００１５】実施例２〜３、比較例１ 表１の配合に従って実施例１と同様に硬化剤組成物を作
成し貯蔵安定性試験を行なった。結果を表１に示した。Examples 2 to 3 and Comparative Example 1 A curing agent composition was prepared in the same manner as in Example 1 according to the formulation shown in Table 1, and a storage stability test was conducted. The results are shown in Table 1.
【００１６】[0016]
【表１】 [Table 1]
【００１７】注）貯蔵安定性の評価 ○：増粘及び白濁なく良好。 □：増粘し、白濁する。 ×：ゲル化。Note) Evaluation of storage stability ◯: Good without thickening or clouding. □: Thickens and becomes cloudy. X: Gelation.
Claims (2)
量％、脱水剤を０．１〜５．０重量％及び有機溶剤を５
５〜９８．９重量％含むことを特徴とする硬化剤組成
物。1. A polyisocyanate compound in an amount of 1 to 40% by weight, a dehydrating agent in an amount of 0.1 to 5.0% by weight, and an organic solvent in an amount of 5%.
A curing agent composition comprising 5 to 98.9% by weight.
る請求項１記載の硬化剤組成物。2. The curing agent composition according to claim 1, wherein the dehydrating agent is a hydrolyzable ester compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4181845A JPH05345871A (en) | 1992-06-16 | 1992-06-16 | Curing agent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4181845A JPH05345871A (en) | 1992-06-16 | 1992-06-16 | Curing agent composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05345871A true JPH05345871A (en) | 1993-12-27 |
Family
ID=16107826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4181845A Pending JPH05345871A (en) | 1992-06-16 | 1992-06-16 | Curing agent composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05345871A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007535582A (en) * | 2003-07-14 | 2007-12-06 | ローディア インコーポレイティド | Improved color stability of isocyanates |
| JP2008529973A (en) * | 2004-12-23 | 2008-08-07 | ロディア・シミ | Isocyanate compositions exhibiting good mixing characteristics, and the use of silylated derivatives as isocyanate composition aids, especially as mixing aids |
| JP2018510255A (en) * | 2015-04-28 | 2018-04-12 | エイチピー・インディゴ・ビー・ブイＨＰ Ｉｎｄｉｇｏ Ｂ．Ｖ． | Coating system |
| CN109942783A (en) * | 2019-02-22 | 2019-06-28 | 上海稻畑精细化工有限公司 | A kind of high stability polyurethane curing agent and preparation process thereof |
-
1992
- 1992-06-16 JP JP4181845A patent/JPH05345871A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007535582A (en) * | 2003-07-14 | 2007-12-06 | ローディア インコーポレイティド | Improved color stability of isocyanates |
| JP2008529973A (en) * | 2004-12-23 | 2008-08-07 | ロディア・シミ | Isocyanate compositions exhibiting good mixing characteristics, and the use of silylated derivatives as isocyanate composition aids, especially as mixing aids |
| JP2018510255A (en) * | 2015-04-28 | 2018-04-12 | エイチピー・インディゴ・ビー・ブイＨＰ Ｉｎｄｉｇｏ Ｂ．Ｖ． | Coating system |
| US10294363B2 (en) | 2015-04-28 | 2019-05-21 | Hp Indigo B.V. | Coating system |
| CN109942783A (en) * | 2019-02-22 | 2019-06-28 | 上海稻畑精细化工有限公司 | A kind of high stability polyurethane curing agent and preparation process thereof |
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