JP6843772B2 - ポリウレタン用途のための反応性アミン触媒 - Google Patents
ポリウレタン用途のための反応性アミン触媒 Download PDFInfo
- Publication number
- JP6843772B2 JP6843772B2 JP2017562323A JP2017562323A JP6843772B2 JP 6843772 B2 JP6843772 B2 JP 6843772B2 JP 2017562323 A JP2017562323 A JP 2017562323A JP 2017562323 A JP2017562323 A JP 2017562323A JP 6843772 B2 JP6843772 B2 JP 6843772B2
- Authority
- JP
- Japan
- Prior art keywords
- amine
- bis
- dimethylaminopropyl
- catalyst
- foam
- 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.)
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- 239000003054 catalyst Substances 0.000 title claims description 156
- 150000001412 amines Chemical class 0.000 title claims description 76
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- 150000003077 polyols Chemical class 0.000 claims description 102
- 229910052757 nitrogen Inorganic materials 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 70
- -1 3-dimethylaminopropyl Chemical group 0.000 claims description 52
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- 239000011496 polyurethane foam Substances 0.000 claims description 41
- 239000012948 isocyanate Substances 0.000 claims description 33
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 32
- 150000002513 isocyanates Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 238000005187 foaming Methods 0.000 claims description 24
- 238000001879 gelation Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 15
- FHXCMYHMMXQRBX-UHFFFAOYSA-N n',n'-bis[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCN(CCCN)CCCN(C)C FHXCMYHMMXQRBX-UHFFFAOYSA-N 0.000 claims description 15
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- WAJVSONFDQROAZ-UHFFFAOYSA-N 3-[bis[3-(dimethylamino)propyl]amino]propanenitrile Chemical compound CN(C)CCCN(CCC#N)CCCN(C)C WAJVSONFDQROAZ-UHFFFAOYSA-N 0.000 claims description 8
- BXYVQNNEFZOBOZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- NCUPDIHWMQEDPR-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol Chemical compound CN(C)CCOCCN(C)CCO NCUPDIHWMQEDPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 41
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- 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 15
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 14
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- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 12
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- 239000012970 tertiary amine catalyst Substances 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000003426 co-catalyst Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
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- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 6
- IIVBUJGYWCCLNG-UHFFFAOYSA-N 3-(dimethylamino)propylurea Chemical compound CN(C)CCCNC(N)=O IIVBUJGYWCCLNG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
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- 239000003431 cross linking reagent Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
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- 229920001228 polyisocyanate Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
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- 229920000638 styrene acrylonitrile Polymers 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
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- 239000003063 flame retardant Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
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- 150000003141 primary amines Chemical class 0.000 description 5
- 238000007142 ring opening reaction Methods 0.000 description 5
- 150000004072 triols Chemical class 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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- 239000004970 Chain extender Substances 0.000 description 4
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- 235000011054 acetic acid Nutrition 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
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- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 4
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
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- FZUWYUIYVKESIP-UHFFFAOYSA-N 9,9-dimethyldecanoic acid Chemical compound CC(C)(C)CCCCCCCC(O)=O FZUWYUIYVKESIP-UHFFFAOYSA-N 0.000 description 3
- PCVAKFVNCSPYNN-UHFFFAOYSA-N 9:0(8Me,8Me) Chemical compound CC(C)(C)CCCCCCC(O)=O PCVAKFVNCSPYNN-UHFFFAOYSA-N 0.000 description 3
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Description
本発明の分野
本発明の背景
米国特許第6,858,654号明細書は、ゲル化触媒および発泡触媒を含む、ポリウレタン生成反応を促進するための触媒組成物を開示している。ゲル化触媒は、第三級アミノアルキル置換第一級または第二級アミンから選択され、かつ発泡触媒は、アルカノール基、第一級アミン基、またはこのような第一級アミン基から誘導されたウレイド基を有するビス(アミノアルキル)エーテルから選択される。この触媒を用いて製造されたフォームは、アミンエミッションを含まない最終生成物を提供することができるが、これらは全ての物理特性要件を満たすことができない。
発明の簡単な説明
本発明は、アミン触媒組成物、およびこの組成物を製造する方法、およびポリウレタンフォームを製造するためのゲル化触媒としての触媒の使用に関する。本発明の触媒は、次の目的で使用することができる:a)フォームの物理特性について妥協することなくフォームエミッションを最小化するため;b)フォームが多様な過酷な環境条件下で水または水分に曝される場合に、水相のpHを増大させることなしに加水分解安定性であるフォームを提供するため;c)触媒がポリウレタンポリマーから移行しないことにより、ポリウレタンに接触する材料を損傷しないため(例えば、ポリカルボナート表面が、温度および湿度の多様な過酷な条件下でポリウレタンフォームに曝される場合);d)例えば目標密度(ASTM 3574−A)、エアフロー(ASTM 3574−G)、ILD(押込荷重法ASTM 3574−B1)、サポートファクタ(ASTM 3574−B1)およびレジリエンス(ASTM 3574−H)およびe)高い触媒活性のためにゲル化アミン触媒の使用レベルの明らかな低減のような物理特性の最適化のため。
本発明の一態様は、化学構造A−NR1R2[式中、A=[Me2N−(CH2)3]2N−(CH2)3−およびR1=R2=−CH2−CH(R3)OHまたはR1=HおよびR2=−CH2−CH(R3)OH、ここでR3=H、C1〜C6、またはA=[Me2N−(CH2)3]2N−(CH2)3−およびR1=HおよびR2=−CO−NH−AまたはR1=HおよびR2=−CO−NH2、ここでMe=CH3基である]を有する第三級アミン触媒に関する。本発明の触媒は、約0.1pphp〜約20pphp、約0.1pphp〜約10pphp、いくつかの場合に約0.1pphp〜約5pphpの範囲の量で使用することができる。
フォームの製造
表1 ポリウレタン成分
NCO指数=[NCO/(OH+NH)]・100
触媒
しかしながら、任意の有効量を使用してもよい。「pphp」の用語は、ポリオール100部当たりの部を意味する。
有機イソシアナート
ポリオール成分
発泡剤
他の任意成分
実施例
手動混合評価
機械評価
実施例1
N,N−ビス−(ジメチルアミノプロピル)−N−(3−アミノプロピル)−アミンの合成
実施例2
N,N−ビス−(ジメチルアミノプロピル)−N−(3−アミノプロピル)−尿素の合成
実施例3
ビス−[N,N−ビス−(ジメチルアミノプロピル)−N−(3−アミノプロピル)]−尿素の合成
実施例4
実施例5
実施例6
実施例2〜5において製造した触媒についての上昇速度論の発泡速度および使用レベル比較
表2:プレミックス成分
2 共重合したスチレンおよびアクリロニトリルを含むグラフトしたポリエーテルポリオール、約4800のベースポリオール分子量、Dow Chemical Company, Midland, MIから入手可能。
3 シリコーン界面活性剤は、Air Products and Chemicals, Inc.から入手可能である。
4 アミン触媒は、Air Products and Chemicals, Inc.から入手可能である。
表3:秒で表すカップトップ発泡時間および糸引きゲル化時間
上昇率のデータは、全ての場合に、発泡アミン触媒のN,N,N−トリチル−N−3−アミノプロピル−ビス(アミノエチル)エーテル0.17pphpを用いて行う。
実施例7
実施例2〜5の触媒を用いて製造したポリウレタンフォームの物理特性
表4:ポリウレタンTDIフレキシブル成形データ
表5:40Kg/m3の密度および指数100を有するTDIポリウレタンフレキシブル成形フォームの物理特性
2 Volkswagen老化手順:試験されるべき試料を乾燥炉内で乾燥のために90℃で24時間放置した。乾燥した後、試料を90℃かつ100%相対湿度で200時間老化させる。次いで試料を乾燥させる。
実施例8
ポリカルボナート表面と接触する場合の、アミン−3およびアミン−4を用いて製造されたPUフォームの老化
表6:ポリカルボナート試験用のフォーム試料
表7:多様な触媒を用いて製造されたフレキシブル成形ポリウレタンフォームと接触させた湿潤老化の場合のポリカルボナート試験体における質量変化
実施例9
製造されたポリウレタンフォームの物理特性
表8:物理特性評価のためのフォーム試料
表9:指数90および密度40Kg/m3でのフレキシブル成形ポリウレタンフォームについての物理特性
実施例10
製造されたフレキシブルな成形ポリウレタンフォームについてのエミッション測定
表11:指数90および指数65でのTDIを基礎とするフレキシブルな成形ポリウレタンフォームからのエミッション
実施例11
アミン−4を用いて製造されたフレキシブルポリウレタンフォームの寸法安定性および標準との比較
表12:ポリウレタンフレキシブル成形フォームの寸法安定性試験のための配合
表13:フレキシブルな成形ポリウレタンフォームの寸法安定性
2 EXT(sec)は、発泡材料が金型通気孔の一つを通して押し出される時間(秒で表す)である。
3 SGT(sec)は、押し出される成形材料について、木製舌圧子で触った際に糸を形成する時間(秒で表す)である糸引きゲル化時間である。
表13および図6は、部材を金型から取り出す際にアミン−3およびアミン−4において収縮を示さない優れた安定性を有するフォームパッドを製造する際の、アミン−3およびアミン−4のさらに付加的な利点を示す。
Claims (9)
- 一般式A−NR1R2[式中、A=[Me2N−(CH2)3]2N−(CH2)3−およびR1=R2=−CH2−CH(R3)OHまたはR1=HおよびR2=−CH2−CH(R3)OH、ここで、R3=H、C1〜C6;またはA=[Me2N−(CH2)3]2N−(CH2)3−およびR1=HおよびR2=−CO−NH−AまたはR1=HおよびR2=−CO−NH2]を示す少なくとも1種の化合物を含む、ポリウレタンを製造するためのゲル化触媒組成物。
- 前記化合物は、N,N′−ビス[ビス−N″,N″−(3−ジメチルアミノプロピル)−N″−(3−アミノプロピル)]尿素;N,N−ビス(3−ジメチルアミノプロピル)−N−(3−アミノプロピル)尿素;N,N−ビス(3−ジメチルアミノプロピル)−N−(ビス(2−ヒドロキシプロピル)−3−アミノプロピル)アミン;N,N−ビス(3−ジメチルアミノプロピル)−N−[N′,N′−ビス(2−ヒドロキシプロピル)−3−アミノプロピル]アミン;およびN,N−ビス(3−ジメチルアミノプロピル)−N−[(2−ヒドロキシプロピル)−3−アミノプロピル]アミンからなる群から選択される少なくとも1つを含む、請求項1記載の組成物。
- さらに、少なくとも1種の発泡触媒を含む、請求項1記載の組成物。
- 前記発泡触媒は、N,N,N′−トリメチル−N′−3−アミノプロピル−ビス(アミノエチル)エーテルおよび/または2−[N−(ジメチルアミノエトキシエチル)−N−メチルアミノ]エタノールを含む、請求項3記載の組成物。
- アクリロニトリルとビス(ジメチルアミノプロピル)アミンとを、ビス(ジメチルアミノプロピル)−シアノエチル−アミンを得るために十分な条件下で接触させること;およびビス(ジメチルアミノプロピル)−シアノエチル−アミンを水素と、N,N−ビス(ジメチルアミノプロピル)−N−(3−アミノプロピル)−アミンを得るために十分な条件下で接触させ、かつN,N−ビス(ジメチルアミノプロピル)−N−(3−アミノプロピル)−アミンを、尿素官能基を有する化合物を製造するために十分な条件下で反応させることを含む、請求項1に記載のゲル化触媒組成物の製造方法。
- N,N−ビス(ジメチルアミノプロピル)−N−(3−アミノプロピル)−アミンを、エチレンオキシドおよびプロピレンオキシドからなる群から選択される少なくとも1つと反応させる、請求項5記載の方法。
- N,N−ビス(ジメチルアミノプロピル)−N−(3−アミノプロピル)−アミンを尿素と反応させる、請求項5記載の方法。
- 少なくとも1種のポリオールと少なくとも1種のイソシアナートとを、請求項1記載の少なくとも1種のゲル化触媒組成物および少なくとも1種の発泡触媒の存在下で接触させることを含む、ポリウレタンフォームの製造方法。
- 少なくとも1種のポリオールを請求項1記載の少なくとも1種のゲル化触媒組成物および少なくとも1種の発泡触媒と組み合わせ、かつこの組合せ物を少なくとも1種のイソシアナートと反応させることを含む、ポリウレタンフォームの製造方法。
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