JP2017521527A - ポリウレタンフォームから放出されるアルデヒドの量を低減させるための組成物 - Google Patents
ポリウレタンフォームから放出されるアルデヒドの量を低減させるための組成物 Download PDFInfo
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- JP2017521527A JP2017521527A JP2017500987A JP2017500987A JP2017521527A JP 2017521527 A JP2017521527 A JP 2017521527A JP 2017500987 A JP2017500987 A JP 2017500987A JP 2017500987 A JP2017500987 A JP 2017500987A JP 2017521527 A JP2017521527 A JP 2017521527A
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- isocyanate
- acid
- amine
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Classifications
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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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
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- C08G18/325—Polyamines containing secondary or tertiary amino groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
Description
ポリウレタンフォーム中にいわゆるスキャベンジャーを組み込むべく、種々の試みがなされている。例えばDE10003157A1は、ポリエチレンイミンポリマーを溶媒中に溶解してから、その溶液をフォーム構造中に吸収させることを開示している。溶媒を乾燥もしくは蒸発させた後に、ポリマー分子がフォーム構造中に残り、アルデヒドスキャベンジャーとして作用する。
■ ポリエーテルポリオール、ポリエステルポリオール、ポリエーテルポリアミン、およびポリエステルポリアミンからなる群から選ばれる少なくとも1種のポリイソシアネート反応性成分;
■ 少なくとも1種のイソシアネート反応性基で置換された環状ウレア、ラジカルスキャベンジャー、ポリマー酸、およびこれらの混合物からなる群から選ばれる処理剤;ならびに、
■ 下式のいずれかの構造を有する1種以上のアミン成分:
単位R1、R2、及び/又はR3のランダム配列とは、式R1、R2、及び/又はR3のそれぞれがアミン成分中に数回現われるという場合の、そしてアミン成分が、式R1、R2、またはR3のうちの少なくとも1種を、あるいはR1、R2、及び/又はR3の組合わせを含んでよい、という場合のR1、R2、及び/又はR3の配列をアミン成分が有してよい、ということを意味する。アミン成分中のR1、R2、またはR3の単位の配列は、好ましくは1〜10回であり、さらに好ましくは1〜5回である。1つの実施態様では、アミン成分がR1、R2、またはR3の単位の配列を含む。他の実施態様では、アミン成分が、R1とR2、R1とR3、またはR2とR3の単位の配列を含む。
平均窒素原子数は、下記の定義に基づいて算出される。
代表的な平均値は6.5〜7.5(たとえば約7)である。
上記式を有する1種以上のアミン成分は、ポリウレアまたはポリウレタンを製造するのに適した反応混合物の一部であるので、製造後のフォームに(たとえば含浸による)後処理を施して、フォーム中にアルデヒド掃去特性を組み込む必要がない。
■ ポリエーテルポリオール、ポリエステルポリオール、ポリエーテルポリアミン、およびポリエステルポリアミンからなる群から選ばれる少なくとも1種の成分;および、
■ 下式のいずれかの構造を有する1種以上のアミン成分:
組成物中の1種以上のアミン成分の量は、組成物の総重量を基準として0.05重量%〜1.0重量%である。
1つの実施態様では、R7'、R8'、およびR9'は独立していて、HまたはCH3から選ばれ、R10'は、HまたはC1-C4アルキル基である。さらに他の実施態様では、R7'、R8'、およびR9'はそれぞれCH3基であり、R10'は、H、メチル基、エチル基、プロピル基、またはイソプロピル基である。
さらに他の実施態様では、処理剤は、上記の少なくとも1種のイソシアネート反応性基で置換された環状ウレアと上記ホスファイトとの混合物である。
好ましい実施態様によれば、1種以上のアミン成分を全て合わせた総重量は、前記のポリウレタンフォームまたはポリウレアフォームを製造するための反応混合物の0.10重量%〜0.35重量%を構成する。
好ましい実施態様によれば、処理剤を全て合わせた総重量は、前記のポリウレタンフォームまたはポリウレアフォームを製造するための反応混合物の0.05重量%〜1重量%、あるいはさらに0.10重量%〜0.45重量%を構成する。
イソシアネート成分は、好ましくはポリイソシアネートであり、トルエンジイソシアネート(TDI)タイプのイソシアネート、ジフェニルメタンジイソシアネート(MDI)タイプのイソシアネート、およびこれらのイソシアネートのプレポリマー(これらに限定されない)を含めて、いかなる種類のポリイソシアネートも含んでよい。
■ 本発明の第1の態様に関して記載した構造を有する1種以上のアミン成分を供給する工程;
■ 本発明の第1の態様に関して記載した処理剤を加える工程;および、
■ 本発明の第1の態様に関して記載した少なくとも1つのイソシアネート反応性成分を加える工程。
留意しておかねばならないことは、特許請求の範囲において使用する「〜を含む」(comprising)という用語は、そのあとに記載されているものに限定されると解釈すべきではなく、他の要素や工程を除外しない、という点である。したがって「〜を含む」(comprising)という用語は、言及されている特徴、工程、または成分の存在を明示しているが、1つ以上の他の特徴、工程、成分、またはこれらの群の存在もしくは付加を除外しない、と解釈しなければならない。したがって「手段AとBを含むデバイス」という表現の範囲は、成分AとBだけからなるデバイスに限定すべきではない。この表現は、本発明に関して、装置の最適の関連成分がAとBである、ということを意味している。
(1) 特に明記しない限り、ある成分の%w、w%、または重量%とは、該成分の重量を、その時点で該成分が存在する組成物の総重量に対するパーセント値として表わしたものである。
下記の成分を含む種々のイソシアネート反応性組成物を準備する(詳細は表1に示す)。
・ 100gのDaltocel(登録商標)F428(Huntsman International社から供給);
・ 4gのDaltocel(登録商標)F526(Huntsman International社から供給);
・ 4gの水;
・ 0.15gのJEFFCAT(登録商標)LED-103(Huntsman International社から供給);
・ 1gのJEFFCAT(登録商標)DPA(Huntsman International社から供給);
・ 0.25gのジエタノールアミン(DELA)
・ 0.9gの気泡安定剤(Evonik社からTegostab B8734 LF2として市販、Tegostab B8734 LF2:低フォギング性のシロキサンベース界面活性剤);
・ 0.33gのアミン成分−本実施例ではテトラエチレンペンタミン(TEPA、Huntsman International社から供給);
・ 0.67gの処理剤1e〔ヒドロキシエチルエチレンウレアとトリス(ジプロピレングリコール)ホスファイトとの混合物を含有する〕
Bでは、上記アミン成分を0.33重量%加えた。この重量%は、反応混合物の重量(すなわち、ポリオール、ポリイソシアネート、および全ての添加剤の合計重量)を基準としたパーセント値である。
こうして得られるポリウレタンフォームを、「Verband Der Automobil Industrie」からの試験法であるVDA276放出試験にかける。
驚くべきことに、組成物が、アミン化合物のほかに処理剤(たとえば、少なくとも1種のイソシアネート反応性基で置換された環状ウレアやラジカルスキャベンジャー)も含む場合、この組成物をポリウレタンフォームの製造に使用すると、アミン化合物だけを使用した場合(E)と比較して、該フォームにおけるホルムアルデヒドの放出量がかなり低いままであるだけでなく、アセトアルデヒドの増大もはるかに低くなる、ということが見出された。
理解しておかねばならないことは、本発明に従った実施態様を提供する上で好ましい実施態様及び/又は材料について説明してきたが、本発明の要旨を逸脱しない範囲において、種々の改良や変更を行ってよい、という点である。
表3に示す成分を使用して、実施例1に記載のようにポリウレタンフォームを製造した。
このフォームはWeston430(Addivant LLC社から市販のホスファイト)を含む。ヒドロキシエチレンウレアはBASF社から市販されており、ポリマー酸は分子量5000のポリアクリル酸である。
Claims (20)
- ポリエーテルポリオール、ポリエステルポリオール、ポリエーテルポリアミン、およびポリエステルポリアミンからなる群から選ばれる少なくとも1つのイソシアネート反応性成分;少なくとも1種のイソシアネート反応性基で置換された環状ウレア、ラジカルスキャベンジャー、ポリマー酸、およびこれらの混合物からなる群から選ばれる処理剤;ならびに、
下式のいずれかの構造を有する1種以上のアミン成分:
を含む組成物。 - 少なくとも1種のイソシアネート反応性基を含有する環状ウレアが、以下の式(I)または(II)を有する、請求項1に記載の組成物:
- 少なくとも1種のイソシアネート反応性基を含有する環状ウレアが、4,5-ジヒドロキシ-2-イミダゾリジノン、4,5-ジメトキシ-2-イミダゾリジノン、4-ヒドロキシエチルエチレンウレア、4-ヒドロキシ-5-メチルプロピレンウレア、4-メトキシ-5-メチルプロピレンウレア、4-ヒドロキシ-5,5-ジメチルプロピレンウレア、1-(2-ヒドロキシエチル)-2-イミダゾリジノン、またはこれらの混合物からなる群から選ばれる、請求項1または2に記載の組成物。
- ラジカルスキャベンジャーが、以下の式(III)を有する立体障害フェノール類を含む、請求項1〜3のいずれか一項に記載の組成物:
- ラジカルスキャベンジャーがホスファイトである、請求項1〜4のいずれか一項に記載の組成物。
- ラジカルスキャベンジャーが、式(IV):
を有する置換ジフェニルアミン芳香族アミン化合物である立体障害アミンである、請求項1〜5のいずれか一項に記載の組成物。 - 前記1種以上のアミン成分の平均窒素原子数が5〜10の範囲であり、好ましくは5〜8の範囲である、請求項1〜6のいずれか一項に記載の組成物。
- 前記1種以上のアミン成分が、少なくとも2つの第一アミン基と少なくとも1つの第二アミン基を含む少なくとも1種の成分を含む、請求項1〜7のいずれか一項に記載の組成物。
- R4基、R5基、R6基、およびR7基の全てが水素である、請求項1〜8のいずれか一項に記載の組成物。
- ポリマー酸が、不飽和カルボン酸または酸無水物の少なくとも3つの同じ繰り返しモノマーを含有するか、あるいはポリマー酸が、少なくとも2つの繰り返しモノマーを含有し、このとき第1のモノマーが不飽和カルボン酸または酸無水物であり、第2のモノマーが第1のモノマーとは異なる、請求項1〜9のいずれか一項に記載の組成物。
- 前記1種以上のアミン成分が、トリエチルアミン(TETA)、テトラエチルペンタミン(TEPA)、ペンタエチルヘキサミン(PEHA)、ヘキサエチルヘプタミン(HEHA)、ヘプタエチルオクタミン(HEOA)、及び/又はオクタエチレンノナミン(OENO)を含む混合物である、請求項1〜10のいずれか一項に記載の組成物。
- 組成物中の1種以上のアミン成分の量が、組成物の総重量を基準として0.05重量%〜1重量%である、請求項1〜11のいずれか一項に記載の組成物。
- 組成物中の処理剤の量が、組成物の総重量を基準として0.05重量%〜2.5重量%である、請求項1〜12のいずれか一項に記載の組成物。
- ポリウレタンフォームまたはポリウレアフォームを製造するための反応混合物中に、請求項1〜13のいずれか一項に記載の組成物を使用することによって、ポリウレタンフォームまたはポリウレアフォームからのホルムアルデヒド及び/又はアセトアルデヒドの放出量を低減させる方法。
- 反応混合物中の1種以上のアミン成分の量が、反応混合物の総重量を基準として0.05重量%〜0.5重量%である、請求項14に記載の方法。
- 反応混合物中の処理剤の量が、反応混合物の総重量を基準として0.05重量%〜2重量%である、請求項14または15に記載の方法。
- 前記反応混合物がさらに、少なくともあるイソシアネート成分;発泡触媒及び/又はゲル化触媒から選ばれる触媒;ならびに必要に応じて、難燃剤、酸化防止剤、界面活性剤、物理的もしくは化学的発泡剤、フィラー、顔料、またはポリウレタン材料において使用される他の任意の一般的添加剤;を含む、請求項14〜16のいずれか一項に記載の方法。
- 前記1種以上のアミン成分が反応混合物に、反応性水素原子を含むイソシアネート反応性成分であるポリエーテルポリオール、ポリエステルポリオール、ポリエーテルポリアミン、およびポリエステルポリアミンからなる群から選ばれるイソシアネート反応性成分の一部として供給される、請求項14〜17のいずれか一項に記載の方法。
- 下式のいずれかの構造を有する1種以上のアミン成分を供給する工程:
少なくとも1種のイソシアネート反応性基で置換された環状ウレア、ラジカルスキャベンジャー、ポリマー酸、またはこれらの混合物からなる群から選ばれる処理剤を加える工程;ならびに、
ポリエーテルポリオール、ポリエステルポリオール、ポリエーテルポリアミン、およびポリエステルポリアミンからなる群から選ばれる少なくとも1種のイソシアネート反応性成分を加える工程;
を含む、請求項1〜13のいずれか一項に記載の組成物の製造方法。 - 組成物がポリマー酸と他の処理剤を含み、1種以上のアミン成分にポリマー酸を加えてから他の処理剤を加える、請求項19に記載の製造方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462022928P | 2014-07-10 | 2014-07-10 | |
US62/022,928 | 2014-07-10 | ||
EP14178274.8 | 2014-07-24 | ||
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PCT/EP2015/065657 WO2016005479A1 (en) | 2014-07-10 | 2015-07-09 | A composition to reduce the amount of aldehydes emitted from polyurethane foams |
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WO2021187070A1 (ja) * | 2020-03-16 | 2021-09-23 | 東ソー株式会社 | 軟質ポリウレタンフォーム形成用二液型組成物、並びに、軟質ポリウレタンフォーム及びその製造方法 |
JP2022512531A (ja) * | 2018-08-02 | 2022-02-07 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタン発泡体のアルデヒド排出量を減少させるための方法 |
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EP2703421A1 (en) * | 2012-08-28 | 2014-03-05 | Huntsman Petrochemical LLC | A composition for making foams with reduced aldehyde emission |
PL3411420T3 (pl) * | 2016-02-05 | 2020-11-16 | Huntsman International Llc | Sposób obniżenia emisji aldehydu w piance poliuretanowej |
EP3293218A1 (de) * | 2016-09-13 | 2018-03-14 | Covestro Deutschland AG | Verfahren zur erniedrigung der aldehydemissionen von polyurethanschaumstoffen |
EP3580248A4 (en) * | 2017-02-09 | 2020-10-21 | Dow Global Technologies LLC | POLYURETHANE FOAMS WITH LOW ALDEHYDE EMISSION VALUES |
WO2018234348A1 (en) | 2017-06-21 | 2018-12-27 | Huntsman International Llc | FORMULATION FOR REDUCING FORMALDEHYDE EMISSION IN PU FOAM |
EP3728368A1 (en) | 2017-12-18 | 2020-10-28 | Huntsman International LLC | Method for reduction of aldehyde emission in polyurethane comprising materials |
PT110585B (pt) * | 2018-02-22 | 2021-04-22 | Hovione Farmaciencia Sa | Processo de produção contínua de partículas compreendendo secagem por atomização com preparação contínua da solução de atomização |
FR3081469B1 (fr) * | 2018-05-28 | 2021-09-03 | Groupe Fp Bois | Utilisation de derives cycliques d'uree pour diminuer la teneur en composes organiques volatils dans l'air ambiant |
JP7227347B2 (ja) * | 2018-08-02 | 2023-02-21 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタン発泡体のアルデヒド排出量を減少させるための方法 |
US20240067771A1 (en) | 2020-12-23 | 2024-02-29 | Basf Se | New catalyst for producing polyurethanes |
WO2023200641A1 (en) * | 2022-04-14 | 2023-10-19 | Huntsman Petrochemical Llc | Mixture for inhibiting the emission of aldehydes from polyurethane foam for an extended period of time |
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BR112016030534A8 (pt) | 2021-05-04 |
RU2712184C2 (ru) | 2020-01-24 |
RU2017104242A (ru) | 2018-08-15 |
BR112016030534A2 (pt) | 2017-08-22 |
CA2954558A1 (en) | 2016-01-14 |
EP3166986B1 (en) | 2023-04-19 |
US10472456B2 (en) | 2019-11-12 |
US20170129988A1 (en) | 2017-05-11 |
RU2017104242A3 (ja) | 2019-01-23 |
JP6722168B2 (ja) | 2020-07-15 |
CN117106151A (zh) | 2023-11-24 |
EP3166986A1 (en) | 2017-05-17 |
WO2016005479A1 (en) | 2016-01-14 |
MX2017000340A (es) | 2017-04-27 |
BR112016030534B1 (pt) | 2021-08-17 |
CN107075062A (zh) | 2017-08-18 |
CA2954558C (en) | 2023-09-26 |
PL3166986T3 (pl) | 2023-07-31 |
KR102390574B1 (ko) | 2022-04-26 |
KR20170032346A (ko) | 2017-03-22 |
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