JP6291011B2 - 水性ポリウレタン尿素組成物含有分散体およびフィルム - Google Patents
水性ポリウレタン尿素組成物含有分散体およびフィルム Download PDFInfo
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- JP6291011B2 JP6291011B2 JP2016216068A JP2016216068A JP6291011B2 JP 6291011 B2 JP6291011 B2 JP 6291011B2 JP 2016216068 A JP2016216068 A JP 2016216068A JP 2016216068 A JP2016216068 A JP 2016216068A JP 6291011 B2 JP6291011 B2 JP 6291011B2
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- prepolymer
- polyurethaneurea
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- film
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4845—Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene end groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
Description
、一般に、引き伸ばしサイクルを繰り返し受けた時の永久歪み(set)の度合が高くかつ回復の度合も劣る。従って、ホットメルト接着剤の性能懸念を克服する接着剤が求められている。そのような接着剤は、好ましくは、また、通常の熱可塑性ポリウレタンおよびホットメルト接着剤と比べた時に布に他の利点、例えば柔軟性、形状保持および空気透過性などを与えるものであろう。
(a)ポリエーテル、ポリエステル、ポリカーボネートおよびこれらの組み合わせから選択される数平均分子量が600から4000の少なくとも1種のポリオール、
(b)芳香族ジイソシアネート、脂肪族ジイソシアネート、脂環式ジイソシアネートおよびこれらの組み合わせから成る群より選択される一員を含有して成るポリイソシアネート、
(c)(i)ポリイソシアネートと反応し得るヒドロキシ基および(ii)中和時に塩を形成する能力を有しかつ前記ポリイソシアネートと反応する能力を持たない少なくとも1種のカルボン酸基を含有して成る少なくとも1種のジオール化合物、
(d)中和剤、
(e)鎖延長剤、
(f)少なくとも1種の単官能アルコールを含有して成るイソシアネート基用ブロッキング剤、
の反応生成物である重合体、および
少なくとも1種の表面活性剤、
を含有する。
(a)(i)ポリエーテル、ポリエステル、ポリカーボネートおよびこれらの組み合わせから選択した数平均分子量が600から4000の少なくとも1種のポリオール、
(ii)芳香族ジイソシアネート、脂肪族ジイソシアネート、脂環式ジイソシアネートおよびこれらの組み合わせから成る群より選択した一員を含有して成るポリイソシアネート、
(iii)(i)ポリイソシアネートと反応し得るヒドロキシ基および(ii)中和時に塩を形成する能力を有しかつ前記ポリイソシアネートと反応する能力を持たない少なくとも1種のカルボン酸基を含有する少なくとも1種のジオール化合物、
の反応生成物を含有するプレポリマー組成物を調製し、
(b)前記プレポリマーを中和剤と表面活性剤を含有する水性組成物に入れて分散させ、
(c)前記プレポリマーの鎖延長を起こさせることで重量平均分子量が約40,000から約250,000のポリウレタン尿素重合体が入っているポリウレタン尿素分散体を生じさせ、そして
(d)イソシアネート基用ブロッキング剤を用いて前記重合体の分子量を調節する、
ことを包含する。
本発明の範囲内に入る水性ポリウレタン分散体を特定のウレタンプレポリマーから生じさせるが、それもまたいくつかの態様の一面を構成する。
ル中に耐え得ると期待する。
で使用可能である。
に引き伸ばしおよび回復、向上した弾性率、接着性、成型性、形状保持および柔軟性を与え得る。そのような製品を布および/または衣類に成形してもよい。
って、そのような製品はポリウレタン尿素フィルムを1層以上およびポリウレタン尿素分散体層を1層以上含有し得る。
めたが、その有用性を衣類に限定するものでなく、また、成形可能もしくは形を成し得る媒体のいずれに関しても適用性を有し、それには、家具用クッション(これらもまた成形可能領域に接触した状態で布が移動しかつある程度の滑りを受ける)が含まれると更に認識している。
させることも可能である。
本発明に従うウレタンプレポリマーを生じさせる時に出発材料として用いるに適したポリオール成分は、数平均分子量が約600から約3,500もしくは約4,000のポリエーテルグリコール、ポリカーボネートグリコールおよびポリエステルグリコールである。
−デカンジオールおよび1,12−ドデカンジオールなどの重縮合で生じたヒドロキシ基数が2以上のグリコールが含まれる。線状の二官能ポリエーテルポリオールが好適であり、本発明では特に分子量が約1,700から約2,100のポリ(テトラメチレンエーテル)グリコール、例えば官能性が2のTerathane(商標)1800(Invista)が好適である。
ンジオール、ネオペンチルグリコール、3−メチル−1,5−ペンタンジオール、1,7−ヘプタンジオール、1,8−オクタンジオール、1,9−ノナンジオール、1,10−デカンジオールおよび1,12−ドデカンジオールである。溶融温度が約5℃から約50℃の線状二官能ポリエステルポリオールが好適である。
適切なポリイソシアネート成分の例には、ジイソシアネート、例えば1,6−ジイソシアナトヘキサン、1,12−ジイソシアナトドデカン、イソホロンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、1,5−ジイソシアナト−2−メチルペンタン、ジイソシアナト−シクロヘキサン、メチレン−ビス(4−シクロヘキシルイソシアネート)、テトラメチル−キシレンジイソシアネート、ビス(イソシアナトメチル)シクロヘキサン、トルエンジイソシアネート、メチレンビス(4−フェニルイソシアネート)、フェニレンジイソシアネート、キシレンジイソシアネートおよび前記ジイソシアネートの
混合物などが含まれる。例えば、そのようなジイソシアネートは芳香族ジイソシアネート、例えばフェニレンジイソシアネート、トリレンジイソシアネート(TDI)、キシリレンジイソシアネート、ビフェニレンジイソシアネート、ナフチレンジイソシアネート、ジフェニルメタンジイソシアネート(MDI)およびこれらの組み合わせであってもよい。
F)およびIsonate(商標)50 O,P'(Dow Chemical)が含まれる。
本発明に従うウレタンプレポリマーを生じさせる時にさらなる出発材料として用いるに適したジオール化合物には、(i)ポリイソシアネートと反応し得るヒドロキシ基を2個および(ii)中和時に塩を形成する能力を有しかつ前記ポリイソシアネート(b)と反応する能力を持たない少なくとも1種のカルボン酸基を有する少なくとも1種のジオール化合物が含まれる。カルボン酸基を有するジオール化合物の典型的な例には、2,2−ジメチロプロピオン酸(DMPA)、2,2−ジメチロブタン酸、2,2−ジメチロ吉草酸およびDMPA開始カプロラクトン、例えばCAPA(商標)HC 1060(Solvay)などが含まれる。本発明ではDMPAが好適である。
酸基を塩基に変化させるに適した中和剤の例には、第三級アミン(例えばトリエチルアミン、N,N−ジエチルメチルアミン、N−メチルモルホリン、N,N−ジイソプロピルエチルアミンおよびトリエタノールアミン)およびアルカリ金属の水酸化物(例えばリチウム、ナトリウムおよびカリウムの水酸化物)が含まれる。また、第一級および/または第二級アミンを酸基中和用の中和剤として用いることも可能である。その中和の度合は一般に酸基の約60%から約140%、例えば約80%から約120%の範囲である。
本発明で用いるに有用な鎖延長剤には、ジアミン系鎖延長剤および水が含まれる。有用な鎖延長剤の数多くの例が通常の当業者に公知である。適切なジアミン系鎖延長剤の例には、1,2−エチレンジアミン、1,4−ブタンジアミン、1,6−ヘキサメチレンジアミン、1,12−ドデカンジアミン、1,2−プロパンジアミン、2−メチル−1,5−ペンタンジアミン、1,2−シクロヘキサンジアミン、1,4−シクロヘキサンジアミン、4,4'−メチレン−ビス(シクロヘキシルアミン)、イソホロンジアミン、2,2−ジメチル−1,3−プロパンジアミン、メタ−テトラメチルキシレンジアミンおよび分子
量が500未満のJeffamine(商標)(Texaco)が含まれる。
適切な表面活性剤(界面活性剤)の例には、アニオン性、カチオン性または非イオン性分散剤または界面活性剤、例えばドデシル硫酸ナトリウム、ナトリウムジオクチルスルホスクシネート、ドデシルベンゼンスルホン酸ナトリウム、エトキシル化アルキルフェノール、例えばエトキシル化ノニルフェノールなど、およびエトキシル化脂肪アルコール、臭化ラウリルピリジニウム、ポリエーテルホスフェートおよび燐酸エステル、修飾アルコール−エトキシレートおよびこれらの組み合わせが含まれる。
イソシアネート基用ブロッキング剤は、単官能アルコールまたは単官能アミンのいずれであってもよい。このブロッキング剤を添加する時期はプレポリマー生成前、プレポリマー生成中またはプレポリマー生成後のいずれであってもよく、それには、プレポリマーを水性媒体、例えば脱イオン水などに入れて分散させる前および後が含まれる。いくつかの態様では、そのブロッキング剤は任意であるか或はそれを排除してもよい。他の態様では、そのようなブロッキング剤を当該プレポリマーの重量を基準にして約0.05%から約10.0%(約0.1%から約6.0%および約1.0%から約4.0%を包含)の量で含有させてもよい。そのようなブロッキング剤を最終的分散体の重量を基準にして約0.01%から約6.0%(約0.05%から約3%および約0.1%から約1.0%を包含)の量で存在させてもよい。
(2−ヒドロキシエチル)スクシニミド、4−(2−ヒドロキシエチル)モルホリン、メタノール、エタノール、ブタノール、ネオペンチルアルコール、ヘキサノール、シクロヘキサノール、シクロヘキサンメタノール、ベンジルアルコール、オクタノール、オクタデカノール、N,N−ジエチルヒドロキシルアミン、2−(ジエチルアミノ)エタノール、2−ジメチルアミノエタノールおよび4−ピペリジンエタノールおよびこれらの組み合わせが含まれる。
適切な消泡もしくは脱泡または泡制御剤の例には、Additive 65およびAdditive 62(Dow Corningのシリコーンが基になった添加剤)、FoamStar(商標)I 300[Cognisの鉱油が基になった脱泡剤(シリコーンを含有しない)]およびSurfynol(商標)DF 110L(Air Products & Chemicalsの非イオン性界面活性剤である高分子量のアセチレン系グリコール)が含まれる。
ポリオールを約34%から約89%(約61%から約80%を包含)、
ポリイソシアネートを約10%から約59%(約18%から約35%を包含)、および
ジオール化合物を約1.0%から約7.0%(約2.0%から約4.0%を包含)。
で単官能アルコールを前記プレポリマーと一緒に含有させてもよい。
1)重合が完了した後であるがプレポリマーを移送して分散させる前のプレポリマーに溶媒を添加して混合してもよく、その希釈されたプレポリマーはバックボーン中にカルボン酸基(ジオール化合物に由来)および鎖末端にイソシアネート基を含有し、それを中和した後、それを水に分散させながら鎖延長を起こさせる。
2)溶媒を他の材料、例えばポリオール、ポリイソシアネートおよびジオール化合物などと一緒に添加して混合することでプレポリマーを溶液中で生じさせた後、そのようにバックボーン中にカルボン酸基を含有しかつ鎖末端にイソシアネート基を含有するプレポリマーを溶液の状態で水に分散させると同時にそれの中和および鎖延長を起こさせる。
3)溶媒をジオール化合物と中和剤の中和された塩と一緒に添加した後にポリオールおよびポリイソシアネートと混合することでプレポリマーを生じさせた後、分散を起こさせてもよい。
4)溶媒をTEAと混合しそして次に生成プレポリマーに添加した後、分散を起こさせてもよい。
5)溶媒をポリオールと一緒に添加して混合した後、ジオール化合物および中和剤を添加しそして次に続いてポリイソシアネートを溶液の状態の中和されたプレポリマーに添加した後、分散を起こさせてもよい。
6)また、溶媒を分散体から除去することも可能であり、特にアセトン工程の場合に可能である。
もよい。
− 引き伸ばした後の永久歪みが約0から10%、例えば約0から5%、典型的には約0
から約3%、
− 伸びが約400から約800%、および
− じん性が約0.5から約3Mpa。
− 50回洗濯した後の剥離強度に関して、洗濯前にそれが示した強度の少なくとも50%を維持、
− 空気透過率が少なくとも約0から約0.5cfm、および
− 24時間の水蒸気透過率が少なくとも約0から約300g/m2。
Pluracol(商標)HP 4000Dは、数平均分子量が4000の第一ヒドロキシ末端線状ポリプロピレンエーテルグリコール[BASF(Bruxelles、ベルギー)から商業的に入手可能]であり、
Mondur(商標)MLは、2,4'−MDI異性体含有量が50−60%で4,4'−MDI異性体含有量が50−40%のジフェニルメタンジイソシアネート(MDI)異性体混合物[Bayer(Baytown、TX)から商業的に入手可能]であり、
Lupranate(商標)MIは、2,4'−MDI異性体含有量が45−55%で4,4'−MDI異性体含有量が55−45%のジフェニルメタンジイソシアネート(MDI)異性体混合物[BASF(Wyandotte、ミシガン)から商業的に入手可能]であり、
Isonate(商標)125MDRは、4,4'−MDI異性体含有量が98%で2,4'−MDI異性体含有量が2%の高純度ジフェニルメタンジイソシアネート(MDI)混合物[Dow Company(Midland、ミシガン)から商業的に入手可能]であり、そして
DMPAは2,2−ジメチロプロピオン酸である。
Claims (3)
- ポリウレタン尿素の水性分散体を製造する方法であって、
(a)(i)ポリエーテル、ポリエステル、ポリカーボネートおよびこれらの組み合わせから選択した数平均分子量が600から4000の少なくとも1種のポリオール、
(ii)芳香族ジイソシアネート、脂肪族ジイソシアネート、脂環式ジイソシアネートおよびこれらの組み合わせから成る群より選択した一員を含有して成るポリイソシアネート、
(iii)(i)ポリイソシアネートと反応し得るヒドロキシ基および(ii)中和時に塩を形成する能力を有しかつ前記ポリイソシアネートと反応する能力を持たない少なくとも1種のカルボン酸基を含有して成る少なくとも1種のジオール化合物、
の反応生成物を含有して成るプレポリマー組成物を調製するステップ、
(b)前記プレポリマーを中和剤と界面活性剤を含有して成る水性組成物に入れて分散させるステップ、
(c)前記プレポリマーの鎖延長を起こさせることで重量平均分子量が40,000から250,000のポリウレタン尿素重合体が入っているポリウレタン尿素分散体を生じさせるステップ、および、
(d)前記プレポリマーの生成前に、イソシアネート基用ブロッキング剤を添加して前記重合体の分子量を調節するステップであって、前記ブロッキング剤が、単官能アルコールであり、前記単官能アルコールが、フルフリルアルコール、テトラヒドロフルフリルアルコール、N−(2−ヒドロキシエチル)スクシニミド、4−(2−ヒドロキシエチル)モルホリン、メタノール、エタノール、ネオペンチルアルコール、ヘキサノール、シクロヘキサノール、シクロヘキサンメタノール、ベンジルアルコール、オクタノール、オクタデカノール、N,N−ジエチルヒドロキシルアミン、2−(ジエチルアミノ)エタノール、2−ジメチルアミノエタノールおよび4−ピペリジンエタノールおよびこれらの組み合わせから成る群より選択される少なくとも1種である、ステップ、
を含んで成る方法。 - 前記単官能アルコールが、ヘキサノールである、請求項1に記載の方法。
- 前記分子量の調節が前記重量平均分子量の調節および前記重合体の分子量分布の調節を包含する請求項1記載の方法。
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Application Number | Priority Date | Filing Date | Title |
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US11/780,819 | 2007-07-20 | ||
US11/780,819 US20080004395A1 (en) | 2005-02-11 | 2007-07-20 | Aqueous polyurethaneurea compositions including dispersions and films |
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EP2181132B1 (en) | 2017-04-26 |
WO2009014973A3 (en) | 2009-03-26 |
CN101802040A (zh) | 2010-08-11 |
EP2181132A2 (en) | 2010-05-05 |
BRPI0813023A2 (pt) | 2020-08-18 |
HK1225748A1 (zh) | 2017-09-15 |
TWI450938B (zh) | 2014-09-01 |
CN105669934A (zh) | 2016-06-15 |
JP2017052963A (ja) | 2017-03-16 |
JP2010534275A (ja) | 2010-11-04 |
JP6324300B2 (ja) | 2018-05-16 |
TW200909539A (en) | 2009-03-01 |
BRPI0813023B1 (pt) | 2021-04-13 |
US20080004395A1 (en) | 2008-01-03 |
KR20100057816A (ko) | 2010-06-01 |
JP2015052125A (ja) | 2015-03-19 |
WO2009014973A2 (en) | 2009-01-29 |
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