JPH02178350A - Polyurethane composition - Google Patents
Polyurethane compositionInfo
- Publication number
- JPH02178350A JPH02178350A JP33470388A JP33470388A JPH02178350A JP H02178350 A JPH02178350 A JP H02178350A JP 33470388 A JP33470388 A JP 33470388A JP 33470388 A JP33470388 A JP 33470388A JP H02178350 A JPH02178350 A JP H02178350A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- polyurethane
- molecular weight
- polyurethane composition
- 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.)
- Granted
Links
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 32
- 239000004814 polyurethane Substances 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000012964 benzotriazole Substances 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- -1 amine compound Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- CGRTZESQZZGAAU-UHFFFAOYSA-N [2-[3-[1-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]-2-methylpropan-2-yl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-2-methylpropyl] 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCC(C)(C)C2OCC3(CO2)COC(OC3)C(C)(C)COC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 CGRTZESQZZGAAU-UHFFFAOYSA-N 0.000 claims 1
- JFHGLVIOIANSIN-UHFFFAOYSA-N dimethyl butanedioate;1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound COC(=O)CCC(=O)OC.CC1(C)CC(O)CC(C)(C)N1CCO JFHGLVIOIANSIN-UHFFFAOYSA-N 0.000 claims 1
- 238000002845 discoloration Methods 0.000 abstract description 6
- 238000000465 moulding Methods 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 6
- 239000000654 additive Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000002649 leather substitute Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- IJLQBCRKBCAKNJ-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-dibutylphenol Chemical compound CCCCC1=CC(CCCC)=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IJLQBCRKBCAKNJ-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004649 discoloration prevention Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、安定化されたポリウレタン組成物に関する。[Detailed description of the invention] (Industrial application field) FIELD OF THE INVENTION This invention relates to stabilized polyurethane compositions.
更に詳しくは、特に成形加工性に優れた耐光変色性ポリ
ウレタン組成物に関するものである。More specifically, the present invention relates to a photochromic-resistant polyurethane composition that has particularly excellent moldability.
（従来の技術）
ポリインシアネート、低分子量多官能活性水素化合物及
び尚分子ポリマージオールから得られるポリウレタンは
力学的性能が優れており、かつ。(Prior Art) Polyurethanes obtained from polyincyanates, low molecular weight polyfunctional active hydrogen compounds, and molecular polymer diols have excellent mechanical properties and.
加工も容易であることから、射出成形品、ホース・チュ
ーブ、フィルム、繊維あるいは人工皮革等の広範囲の用
途に利用ごｔている。中でも４，４′−ジフェニルメタ
ンジイソシアネーｈｔ［Ｉｌ）などの芳香族系のインシ
アネートを成分にしたポリウレタンは、特に力学的性能
が優れているために、重要なものである。しかしながら
、芳香族系のインシアネートを成分にしたポリウレタン
は、日光や人工の光に当った場合に友色するという欠点
がある。Because it is easy to process, it is used in a wide range of applications such as injection molded products, hoses and tubes, films, fibers, and artificial leather. Among them, polyurethanes containing aromatic incyanates such as 4,4'-diphenylmethane diisocyanate ht[Il] are particularly important because of their excellent mechanical performance. However, polyurethanes containing aromatic incyanates have the disadvantage of becoming amochromic when exposed to sunlight or artificial light.
この欠点をＩＩＪｌ決するだのに主に二つの方法が提案
されている。一つは、芳香族イソシアネートの代りに脂
肪族イソシアネートや脂環族イソシア不−１・全便う方
法である。二つめは、芳香族イソシアネートを用いて、
制光性改良剤を加える方法である。Two main methods have been proposed to overcome this drawback. One is a method in which an aliphatic isocyanate or an alicyclic isocyanate is used instead of an aromatic isocyanate. The second method is to use aromatic isocyanates.
This method involves adding a light control improver.
（発明が解決しようとする課題）
前者の方法では、光での変色は改良されるが、ポリウレ
タンの力学的性能が低下するという欠点がある。衷だ後
稽の方法では、フィルム、チューブなどの押出成形加工
時にダイ部に不融の汚れ物が付着して製品欠点の原因に
なったり、繊維の紡糸時に口金が汚れて断糸の原因にな
ると（・う欠点があった。また、ポリウレタン製品とし
て長期間使用している間に、１光改良剤が製品表面にブ
リードアウトして外観を損なうという欠点があった。(Problems to be Solved by the Invention) The former method improves discoloration due to light, but has the disadvantage that the mechanical performance of polyurethane deteriorates. With this method, infusible dirt may adhere to the die during extrusion processing of films, tubes, etc., causing product defects, or the nozzle may become dirty during fiber spinning, causing yarn breakage. However, there was also a drawback that, during long-term use as a polyurethane product, the light improving agent bleed out onto the surface of the product, impairing its appearance.
（課題を解決するための手段）
本発明者らは、これらの問題を解決するために鋭意研究
を重ねた結果、本発明に係る限定された添加剤の組合せ
によって、成形加工性が著しく改良でさることを見い出
した。(Means for Solving the Problems) As a result of extensive research in order to solve these problems, the present inventors have found that moldability can be significantly improved by the limited combination of additives according to the present invention. I discovered something.
即ち本発明は、ポリウレタンに一般式
（式中Ａは炭素数２〜４のアルキレン基を表わす。）で
表わされる基を少なくとも１個有する分子量が一般式
で表わされる基を少なくとも１個有する分子量が５００
以上のヒンダードフェノール糸化合物（ＪＩ）テ表ワさ
れるベンゾトリアゾール系化合物（ＩＩＩｌを含有させ
てなることを特徴とするポリウレタン組成物である。That is, the present invention provides polyurethane with a molecular weight having at least one group represented by the general formula (wherein A represents an alkylene group having 2 to 4 carbon atoms) and a polyurethane having a molecular weight having at least one group represented by the general formula 500
This is a polyurethane composition characterized by containing a benzotriazole compound (III) represented by the above-mentioned hindered phenol compound (JI).
化合物（Ｉｌの分子量は１０００以上である。また化合
物（１１）の分子量は５００以上である。これよりも小
ざいものでは、ポリウレタンの光変色の防止効果はある
が、成形加工時のトラブルが発生し易く、またポリウレ
タン表面へのブリードアウト現象が発生し易いので好王
しくない。The molecular weight of the compound (Il is 1000 or more. The molecular weight of compound (11) is 500 or more. If it is smaller than this, it will have the effect of preventing photodiscoloration of polyurethane, but it will cause trouble during molding processing. This is undesirable because it tends to cause bleed-out to the polyurethane surface.
化合物ｔＩ＋、ｍ＋及び［１１１の添加量はいずれもポ
リウレタンに対して０．１〜０５重量％が好ましい。こ
れより少ない場合は、光変色防止効果が小ざい。The amount of compounds tI+, m+ and [111 added is preferably 0.1 to 05% by weight based on the polyurethane. If the amount is less than this, the effect of preventing photodiscoloration will be small.
多い場合は、ポリウレタンが白濁し１こり、ブリードア
ウト現象が発生し易くなるので好ましくない。If the amount is too large, the polyurethane becomes cloudy, stiff, and bleed-out phenomenon is likely to occur, which is not preferable.
化合物ｉｌ＋、（ＩＩＩ ｆｆｉたは＠）をポリウレタ
ンの光安定剤として単独で用いた場合は、いずれも成形
加工時のドラフルやポリウレタンの分解やブリードアウ
トなどの障害は起こし難いが、変色防止効果は充分では
なく、満足のいくものではない。When the compound il+, (III ffi or @) is used alone as a light stabilizer for polyurethane, problems such as drafting during molding, polyurethane decomposition and bleed-out are unlikely to occur, but the discoloration prevention effect is low. Not enough, not satisfying.
しかしながら、化合物（Ｉｌ、 ［■）及びＱｌｌｌを
併用した場合にのみ卓店した効果が発現される。However, significant effects are expressed only when compound (Il, [■) and Qlll are used together.
化合物［Ｉ］としては、コハク酸ジメチル−１〜（２−
ヒドロキシエチル）−４−ヒドロキシ−２゜２、Ｊ６−
テトラメチルビペリジン重縮合物（Ｉ−ａ）などがある
。Compound [I] includes dimethyl succinate-1 to (2-
hydroxyethyl)-4-hydroxy-2゜2, J6-
Examples include tetramethylbiperidine polycondensate (I-a).
ｎ：分子量が３０００以上の数（Ｉ−１化合物〔■〕と
しては、
テトラギスー〔メチレン−３−（３’、５−ジーも一ブ
チルー４−ヒドロキシフェニルクプロビオネート）−メ
タン （ｎ−ａ）３．９
−ヒス（２−［３−（３−ｔ−ブチル−４−ヒドロキシ
−５−メチルフェニル）プロピオニルオキシ〕−１，１
−ジメチルエチル） −２，４，８，１０−テトラオキ
サスピロ （５，５］ ウンデカン（ＩＩ−ｂＪトリエ
チレングリコール−ビス（３−（３−ｔ−ブチル−５−
メチル−４−ヒドロキシフェニル）プロピオネート〕（
■−Ｃ）
２−（２−ヒドロキシ−３，５−ジ〜ｔ −’７ミルフ
エニル）−ベンゾトリアゾール （ｉ−ｂ）１
．６−ヘキサンシオールービス（３−（３，５−ジ−ｔ
−７’チル−４−ヒドロキシフェニル）プロピオネート
〕
（ｎ−ｄ）
などがある。n: number with a molecular weight of 3000 or more (I-1 compound [■] is tetragysu[methylene-3-(3',5-di-butyl-4-hydroxyphenylcuprobionate)-methane (n-a) 3.9
-His(2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1
-dimethylethyl) -2,4,8,10-tetraoxaspiro (5,5] undecane (II-bJ triethylene glycol-bis(3-(3-t-butyl-5-
Methyl-4-hydroxyphenyl)propionate] (
-C) 2-(2-hydroxy-3,5-di-t-'7milphenyl)-benzotriazole (ib)1
．． 6-hexanethiolubis(3-(3,5-di-t)
-7'thyl-4-hydroxyphenyl)propionate] (nd).
化合物（皿としては。Compound (as a dish.
２−（２’−ヒドロキシ−５−１−オクチルフエニｔ
−ｃＢ［Ｉ。2-(2'-hydroxy-5-1-octylphenyl
-cB[I.
Ｌ−Ｃ出１１
２−（２−ヒドロキシ−３’、 ５’−ジーも一ブチル
フェニル）−ベンゾトリアゾール （ｉｌｌ−
ｅ）Ｃ（ＣＨ３）３
などがある。L-C Output 11 2-(2-hydroxy-3', 5'-di-butylphenyl)-benzotriazole (ill-
e) C(CH3)3, etc.
化合物（Ｉｌ、（川及び皿とポリウレタンとの混合方法
は特に限定されるものではなく、ポリウレタンの生成中
もしくは生成後に混合することが可能であるが、生成後
に混合する方が、効果はより顕著であり、好ましい。The method of mixing the compound (Il) with the polyurethane is not particularly limited, and it is possible to mix it during or after the production of the polyurethane, but the effect is more pronounced when mixed after the production of the polyurethane. and is preferable.
本発明のポリウレタン組成物は、従来のボリウつ
レタン用途上いずれにでも使用できるが、光変色が少な
いので、透明なチューブ・フィルム、透明な靴底部品に
代表される透明もしくは淡色の押出成形品・射出成形品
、人工皮革、合成皮革、あるいは繊維分野で有効に使用
されうる。The polyurethane composition of the present invention can be used in any conventional polyurethane application, but since it has little photodiscoloration, it can be used in transparent or light-colored extrusion molded products such as transparent tube films and transparent shoe sole parts. - Can be effectively used in injection molded products, artificial leather, synthetic leather, or textile fields.
以下に実施例にて本発明を更に詳しく説明するが、本発
明は実施例で限定されうるものではない。The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited to the Examples.
化合物ＩＶ
ｍ−なお、添加剤は本文説明中の（）内の略号および以
下の（）内の略号で示した。Compound IV m-Additives are indicated by the abbreviations in parentheses in the text description and the abbreviations in parentheses below.
化合物■−ａ ２− （３，５−ジ−ｔ−ブチル−４
−ヒドロキシベンジル）−２−ｎ
ブチルマロン酸ビス（１，２，２，６゜６−ベンタメチ
ルー４−ピペリジ
ル）
化合物■
テトラキス−（２，２，６，６−テトラメチル−４−ピ
ペリジル） −１，２゜３．４−ブタンテトラカルボキ
シレ
ート
４．４−ブチリデン−ビス−（３−
メチル−６−ｔ−プチルフエ／−
ルン
化合物ＩＶ−ｂ ビス−（２，２，６，６−テトラメ
チル−４−ピペリジル）セバケート
化合物ｖ−ｂ
（引ｊハＣ
２，６−ジ
ｔ−フチルー４−メチ
実施例１〜５、比較例
１．４−ブタンジオールとアジピン酸とから縮重合して
得られた平均分子量が約１０００の高分子ジオール１９
０重量部、１．４−ブタンジオール１９重量部及び４．
４′−ジフェニルメタンジイソシアネート１００重量部
から、無溶媒下の溶融重合法で得られた熱可塑性ポリウ
レタンと各種添加剤を表１に示した割合で、２５φ、Ｌ
／Ｄ＝２５の単軸スクリュー押出機（■プラスチック工
学研究所製二〇Ｔ−２５）で混合し、ベレット化した。Compound ■-a 2- (3,5-di-t-butyl-4
-Hydroxybenzyl)-2-n Butylmalonate bis(1,2,2,6゜6-bentamethyl-4-piperidyl) Compound ■ Tetrakis-(2,2,6,6-tetramethyl-4-piperidyl) -1 ,2゜3.4-butanetetracarboxylate 4.4-butylidene-bis-(3-methyl-6-t-butylphene/-Run compound IV-b bis-(2,2,6,6-tetramethyl- 4-Piperidyl) sebacate compound v-b (ind. 2,6-dit-phthyl-4-methythyl) Examples 1 to 5, Comparative Example 1. Obtained by condensation polymerization from 4-butanediol and adipic acid Polymeric diol 19 with an average molecular weight of about 1000
0 parts by weight, 19 parts by weight of 1,4-butanediol, and 4.
From 100 parts by weight of 4'-diphenylmethane diisocyanate, a thermoplastic polyurethane obtained by a solvent-free melt polymerization method and various additives were added in the proportions shown in Table 1 to form a 25φ, L
/D=25 single screw extruder (■20T-25 manufactured by Plastic Engineering Research Institute) and pelletized.
このペレットを８０℃で４時間除湿乾燥し、前記押出機
で長時間押出実験を行ない、３φのダイ陥
部分に目視状の塊りが発生するまでの時間を測定し成形
性を評価した。The pellets were dehumidified and dried at 80° C. for 4 hours, and extruded for a long time using the extruder described above, and the moldability was evaluated by measuring the time until visible lumps appeared in the 3φ die cavity.
また、同一のベレットを用いて射出成形機（日精樹脂工
業株製： Ｆ８ ８０８ １２Δ ＳＥ目こて厚ざ２Ｍ
１１．直径１２０閣の円板を作成した。この板を用いて
フェード照射実験を行ない耐光性を評価した。照射条件
と評価方法は下記のとおりである。In addition, using the same pellet, an injection molding machine (manufactured by Nissei Jushi Kogyo Co., Ltd.: F8 808 12Δ SE, trowel thickness 2M) was used.
11. A disk with a diameter of 120 temples was created. A fade irradiation experiment was conducted using this plate to evaluate its light resistance. The irradiation conditions and evaluation method are as follows.
（１）照射条件： ＪＩＳ Ｋ−０８２４の染色堅牢
度試験用カーボン灯型耐光試験機（６３±２℃）による
２００時間照射
（２）評価方法
（１）変色度； ＪＩＳ Ｌ−０８０４の変退色グレ
ースケールに準じて判断した。(1) Irradiation conditions: Irradiation for 200 hours using a carbon lamp type light fastness tester (63±2°C) for color fastness testing according to JIS K-0824 (2) Evaluation method (1) Degree of discoloration: Discoloration and fading according to JIS L-0804 Judgment was made according to gray scale.
（５号：変色なし、１号：変色大）
（１１）ブリート７ウト：内眼観察による判定（良ニブ
リードアウトなし、不良ニ
ブリードアウトあり）
亮犀邊＆ｘ＝ 禾し「−
）・を丁１″；白
（発明の効果）
以上説明したように、ポリウレタンに対し特定の添加剤
を配合することにより、成形加工性に優れた耐光変色性
ポリウレタン組成物が提供される。(No. 5: No discoloration, No. 1: Severe discoloration) (11) Burito 7 out: Judgment by intraocular observation (good nib lead-out, no bad nib lead-out) 1''; White (Effects of the Invention) As explained above, by blending specific additives with polyurethane, a light-resistant polyurethane composition with excellent moldability can be provided.
Claims (3)
表わされる基を少なくとも１個有する分子量が１０００
以上のヒンダードアミン系化合物（ I ）一般式 ▲数式、化学式、表等があります▼ 式中、Ｂは炭素数２〜４のアルキレン基を表わす。また
Ｒ＿１及びＲ＿２は水素原子またはアルキル基を表わし
、同時に水素原子であることはない。 で表わされる基を少なくとも１個有する分子量が５００
以上のヒンダードフエノール系化合物（II）及び一般式 ▲数式、化学式、表等があります▼ （式中、Ｒ＿３及びＲ＿４は水素原子またはアルキル基
を表わし、同時に水素原子であることはない。）で表わ
されるベンゾトリアゾール系化合物（III）を含有させ
てなることを特徴とするポリウレタン組成物。(1) Polyurethane has a general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, A represents an alkylene group having 2 to 4 carbon atoms.)
General formula of the above hindered amine compound (I) ▲ Numerical formula, chemical formula, table, etc. ▼ In the formula, B represents an alkylene group having 2 to 4 carbon atoms. Further, R_1 and R_2 represent a hydrogen atom or an alkyl group, and cannot be hydrogen atoms at the same time. The molecular weight is 500 and has at least one group represented by
The above hindered phenol compound (II) and general formula ▲ mathematical formula, chemical formula, table, etc. ▼ (In the formula, R_3 and R_4 represent a hydrogen atom or an alkyl group, and cannot be hydrogen atoms at the same time.) A polyurethane composition comprising the benzotriazole compound (III) shown below.
ンに対していずれも０．１〜０．５重量％である請求項
１に記載のポリウレタン組成物。(2) The polyurethane composition according to claim 1, wherein each of the compounds (I), (II) and (III) is contained in an amount of 0.1 to 0.5% by weight based on the polyurethane.
ジメチル−１−（２−ヒドロキシエチル）−４−ヒドロ
キシ−２，２，６，６−テトラメチルピペリジン重縮合
物 ▲数式、化学式、表等があります▼ であり、化合物（II）が３，９−ビス［２−〔３−（３
−ｔ−ブチル−４−ヒドロキシ−５−メチルフェニル）
プロピオニルオキシ〕−１，１−ジメチルエチル〕−２
，４，８，１０−テトラオキサスピロ（５，５）ウンデ
カン ▲数式、化学式、表等があります▼ であり、化合物（III）が２−（２′−ヒドロキシ−５
′−ｔ−オクチルフェニル）−ベンゾトリアゾール▲数
式、化学式、表等があります▼ である請求項１に記載のポリウレタン組成物。(3) Compound (I) is a dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate with a molecular weight of 1000 or more▲Mathematical formulas, chemical formulas, tables, etc. ▼ and compound (II) is 3,9-bis[2-[3-(3
-t-butyl-4-hydroxy-5-methylphenyl)
Propionyloxy]-1,1-dimethylethyl]-2
,4,8,10-tetraoxaspiro(5,5)undecane▲Mathematical formulas, chemical formulas, tables, etc.▼, and compound (III) is 2-(2'-hydroxy-5
2. The polyurethane composition according to claim 1, which is `-t-octylphenyl)-benzotriazole (numerical formula, chemical formula, table, etc.).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33470388A JP2765899B2 (en) | 1988-12-29 | 1988-12-29 | Polyurethane composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33470388A JP2765899B2 (en) | 1988-12-29 | 1988-12-29 | Polyurethane composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02178350A true JPH02178350A (en) | 1990-07-11 |
| JP2765899B2 JP2765899B2 (en) | 1998-06-18 |
Family
ID=18280272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33470388A Expired - Lifetime JP2765899B2 (en) | 1988-12-29 | 1988-12-29 | Polyurethane composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2765899B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0665294A2 (en) * | 1994-01-19 | 1995-08-02 | Ciba-Geigy Ag | Stabilisation of leather against thermic and photochemical decomposition |
-
1988
- 1988-12-29 JP JP33470388A patent/JP2765899B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0665294A2 (en) * | 1994-01-19 | 1995-08-02 | Ciba-Geigy Ag | Stabilisation of leather against thermic and photochemical decomposition |
| EP0665294A3 (en) * | 1994-01-19 | 1995-08-16 | Ciba Geigy Ag |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2765899B2 (en) | 1998-06-18 |
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