JP7039724B2 - ポリウレタン発泡体のアルデヒド含有量を減少させるための組成物および方法 - Google Patents
ポリウレタン発泡体のアルデヒド含有量を減少させるための組成物および方法 Download PDFInfo
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- JP7039724B2 JP7039724B2 JP2020551841A JP2020551841A JP7039724B2 JP 7039724 B2 JP7039724 B2 JP 7039724B2 JP 2020551841 A JP2020551841 A JP 2020551841A JP 2020551841 A JP2020551841 A JP 2020551841A JP 7039724 B2 JP7039724 B2 JP 7039724B2
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- 238000000034 method Methods 0.000 title claims description 21
- 229920005830 Polyurethane Foam Polymers 0.000 title description 19
- 239000011496 polyurethane foam Substances 0.000 title description 19
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- -1 Sulfite compound Chemical class 0.000 claims description 71
- 229920005862 polyol Polymers 0.000 claims description 71
- 150000003077 polyols Chemical class 0.000 claims description 71
- 229920002873 Polyethylenimine Polymers 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 62
- 229920000642 polymer Polymers 0.000 claims description 17
- 229920002635 polyurethane Polymers 0.000 claims description 16
- 239000004814 polyurethane Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 235000010265 sodium sulphite Nutrition 0.000 claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 30
- 239000006260 foam Substances 0.000 description 20
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
- 239000000523 sample Substances 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000012855 volatile organic compound Substances 0.000 description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
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- 235000019645 odor Nutrition 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- 239000002184 metal Substances 0.000 description 4
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- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 206010051181 Nasal odour Diseases 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
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- 230000008821 health effect Effects 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08G18/3228—Polyamines acyclic
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- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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- C08J9/286—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
背景
[0002]ポリウレタンポリマーは、多種多様な用途、たとえばポリウレタン発泡体の生成に使用される。これらのポリウレタン発泡体は次に、多くの異なる最終用途に使用される。たとえば、ポリウレタン発泡体は、たとえば、交通機関の座席(たとえば、自動車の座席)ならびに家具、たとえばマットレスおよび他のクッション付き家具におけるクッション材および詰め物として頻繁に使用される。これらのポリウレタン発泡体が密閉環境、たとえば自動車または他の車両の内部で使用される場合、発泡体は、典型的には、発泡体が放出する可能性のある揮発性有機化合物の量を制限する試験に合格しなければならない。試験中にポリウレタン発泡体が放散する揮発性有機化合物は、ポリウレタンポリマーを生成する反応の副生成物として生成される可能性がある。揮発性有機化合物(たとえば、アルデヒド、たとえばホルムアルデヒド、アセトアルデヒド、およびプロピオンアルデヒド)は、発泡体の作製に使用される原料(たとえば、ポリオール)中に存在する可能性もある。これらの揮発性有機化合物は、原料およびそれらの原料を用いて作製されるポリウレタンポリマー/発泡体に望ましくない悪臭を付与する可能性がある。したがって、これらの原料および/またはそうした材料を用いて製造されるポリウレタンポリマー/発泡体中に存在する揮発性有機化合物の検出可能レベルを低下させる組成物または方法を見出すことが望ましい。本願は、そうした組成物および方法の提供を追求するものである。
発明の概要
[0003]第1の態様において、本発明は、
(a)ポリオール;
(b)ポリエチレンイミン化合物;および
(c)亜硫酸塩化合物
を含む組成物を提供する。
(a)ポリオールを準備する工程;
(b)ポリエチレンイミン化合物と亜硫酸塩化合物とを含む添加剤組成物を準備する工程;
(c)ポリオールと添加剤組成物とを組み合わせてポリオール組成物を生成する工程;
(d)イソシアネート化合物を準備する工程;および
(e)ポリオール組成物とイソシアネート化合物とを組み合わせ、反応させて、ポリウレタンポリマーを生成する工程
を含む。
発明の詳細な説明
[0005]第1の態様において、本発明は、ポリオール、ポリエチレンイミン化合物、および亜硫酸塩化合物を含む組成物を提供する。ポリエチレンイミン化合物と亜硫酸塩化合物との組合せは、ポリウレタン発泡体の製造に使用される成分(たとえば、ポリオール)に添加すると、驚くべきことに、ポリウレタン発泡体からのアルデヒドの放散を減少させることが見出されている。さらに、ポリエチレンイミン化合物と亜硫酸塩化合物との組合せは、硫黄化合物を含有する他の組合せが発する可能性のある硫黄臭を発しない。
[0024]この例は、本発明による組成物の生成、およびポリウレタンポリマー、より具体的には、ポリウレタン発泡体の生成におけるこの組成物の使用を実証するものである。この例の結果は、本発明の組成物を用いて製造されたポリウレタンポリマー/発泡体から観察されたアルデヒド放散の劇的な減少も示している。
Claims (23)
- (a)ポリオール;
(b)ポリエチレンイミン化合物;および
(c)亜硫酸塩化合物
を含み、
ここで、前記亜硫酸塩化合物は、組成物中に存在するポリオールの重量を基準として、200ppm~5,000ppm存在する、組成物。 - 前記ポリオールが、400g/mol以上のモル質量を有する、請求項1に記載の組成物。
- 前記ポリオールが、ポリエーテルポリオールである、請求項1または2に記載の組成物。
- 前記ポリエチレンイミン化合物が、前記ポリオールの重量を基準として、100ppm以上の量で前記ポリオール中に存在する、請求項1~3の何れか1項に記載の組成物。
- 前記ポリエチレンイミン化合物が、前記ポリオールの重量を基準として、100ppm~2,000ppmの量で前記ポリオール中に存在する、請求項4に記載の組成物。
- 前記ポリエチレンイミン化合物が、500g/mol以上のモル質量を有する、請求項1~5の何れか1項に記載の組成物。
- 前記亜硫酸塩化合物が、亜硫酸ナトリウムである、請求項1~6の何れか1項に記載の組成物。
- 前記ポリエチレンイミン化合物と前記亜硫酸塩化合物が、前記ポリエチレンイミン化合物1重量部当たり亜硫酸塩化合物が0.5~5重量部の量で存在する、請求項1~7の何れか1項に記載の組成物。
- 前記ポリエチレンイミン化合物と前記亜硫酸塩化合物が、前記ポリエチレンイミン化合物1重量部当たり亜硫酸塩化合物が3~5重量部の量で存在する、請求項8に記載の組成物。
- 前記亜硫酸塩化合物が、前記ポリオールの重量を基準として、500ppm~5,000ppmの量で前記組成物中に存在する、請求項9に記載の組成物。
- 前記組成物が水をさらに含む、請求項1~10の何れか1項に記載の組成物。
- 前記組成物中に存在する前記ポリエチレンイミン化合物と前記亜硫酸塩化合物が総重量を有し、前記組成物が、前記ポリエチレンイミン化合物と前記亜硫酸塩化合物の前記総重量の1~5倍の量で水を含む、請求項11に記載の組成物。
- ポリウレタンポリマーを生成するための方法であって、
(a)ポリオールを準備する工程;
(b)ポリエチレンイミン化合物と亜硫酸塩化合物とを含む添加剤組成物を準備する工程;
(c)前記ポリオールと前記添加剤組成物とを組み合わせてポリオール組成物を生成する工程
(d)イソシアネート化合物を準備する工程;および
(e)前記ポリオール組成物と前記イソシアネート化合物とを組み合わせ、反応させて、ポリウレタンポリマーを生成する工程
を含み、
ここで、前記亜硫酸塩化合物は、組成物中に存在するポリオールの重量を基準として、200ppm~5,000ppm存在する、方法。 - 前記ポリオールが、400g/mol以上のモル質量を有する、請求項13に記載の方法。
- 前記ポリオールが、ポリエーテルポリオールである、請求項13または14に記載の方法。
- 前記ポリエチレンイミン化合物が、前記ポリオールの重量を基準として、100ppm以上の量で添加される、請求項13~15の何れか1項に記載の方法。
- 前記ポリエチレンイミン化合物が、前記ポリオールの重量を基準として、100ppm~2,000ppmの量で添加される、請求項16に記載の方法。
- 前記ポリエチレンイミン化合物が、500g/mol以上のモル質量を有する、請求項13~17の何れか1項に記載の方法。
- 前記亜硫酸塩化合物が、亜硫酸ナトリウムである、請求項13~18の何れか1項に記載の方法。
- 前記添加剤組成物が、前記ポリエチレンイミン化合物1重量部当たり0.5~5重量部の亜硫酸塩化合物を含む、請求項13~19の何れか1項に記載の方法。
- 前記亜硫酸塩化合物が、前記ポリオールの重量を基準として、500ppm~5,000ppmの量で添加される、請求項20に記載の方法。
- 前記添加剤組成物が水をさらに含む、請求項12~21の何れか1項に記載の方法。
- 前記添加剤組成物が、50~90重量%の水を含む、請求項22に記載の方法。
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| US62/648,626 | 2018-03-27 | ||
| PCT/US2019/020544 WO2019190704A1 (en) | 2018-03-27 | 2019-03-04 | Composition and method for reducing aldehyde content in polyurethane foams |
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| US11629251B2 (en) | 2023-04-18 |
| CN111868134B (zh) | 2022-07-05 |
| CN111868134A (zh) | 2020-10-30 |
| US20210222004A1 (en) | 2021-07-22 |
| BR112020017565B1 (pt) | 2024-01-30 |
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