CN105209512A - 高吸声的硬质聚氨酯泡沫 - Google Patents
高吸声的硬质聚氨酯泡沫 Download PDFInfo
- Publication number
- CN105209512A CN105209512A CN201380075129.2A CN201380075129A CN105209512A CN 105209512 A CN105209512 A CN 105209512A CN 201380075129 A CN201380075129 A CN 201380075129A CN 105209512 A CN105209512 A CN 105209512A
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- polyurethane foams
- hydroxyl value
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- 238000010521 absorption reaction Methods 0.000 title claims abstract description 25
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- 239000012948 isocyanate Substances 0.000 claims description 21
- 150000002513 isocyanates Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 16
- 235000011187 glycerol Nutrition 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
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- 239000004814 polyurethane Substances 0.000 claims description 7
- 238000007596 consolidation process Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000011358 absorbing material Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
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- -1 chloro-2-propyl group Chemical group 0.000 description 23
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 22
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- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229920006389 polyphenyl polymer Polymers 0.000 description 6
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229960002479 isosorbide Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- DFKZNFOZJHOROX-UHFFFAOYSA-N 1-imidazol-1-ylpropan-2-amine Chemical class CC(N)CN1C=CN=C1 DFKZNFOZJHOROX-UHFFFAOYSA-N 0.000 description 1
- WCDFMPVITAWTGR-UHFFFAOYSA-N 1-imidazol-1-ylpropan-2-ol Chemical class CC(O)CN1C=CN=C1 WCDFMPVITAWTGR-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical class OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
- IIVBUJGYWCCLNG-UHFFFAOYSA-N 3-(dimethylamino)propylurea Chemical compound CN(C)CCCNC(N)=O IIVBUJGYWCCLNG-UHFFFAOYSA-N 0.000 description 1
- BRKHZWFIIVVNTA-UHFFFAOYSA-N 4-cyclohexylmorpholine Chemical compound C1CCCCC1N1CCOCC1 BRKHZWFIIVVNTA-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical group CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
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- 230000003712 anti-aging effect Effects 0.000 description 1
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- 150000001621 bismuth Chemical class 0.000 description 1
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- 125000000118 dimethyl group Polymers [H]C([H])([H])* 0.000 description 1
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- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- QATBRNFTOCXULG-UHFFFAOYSA-N n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCNCCN QATBRNFTOCXULG-UHFFFAOYSA-N 0.000 description 1
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- 239000012766 organic filler Substances 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本发明涉及主要(>50体积%)开孔的(根据DIN?ISO?4590-86)、可冷变形的硬质聚氨酯泡沫,其具有高吸声和均匀的泡孔结构并适用于制造汽车内饰,更特别是车顶内衬和柱饰板。
Description
本发明涉及主要(>50体积%)开孔的(根据DIN ISO 4590-86)、可冷变形的硬质聚氨酯泡沫,其具有高吸声和均匀的泡孔结构并适用于制造汽车内饰,更特别是车顶内衬和柱饰板。
作为夹层结构的中间层的硬质聚氨酯(PU)泡沫及其在汽车内饰制造中的用途是本身已知的。
用作车顶内衬或柱饰板的夹层结构如今通常由相应的夹层板通过冷成形法制造。在这种方法中,在硬质PU泡沫板的两面上都提供热固性粘合剂和增强材料,如玻璃纤维和/或天然纤维的垫或网,和/或玻璃纤维粗纱,还提供纸、热塑性薄膜和/或无纺纤维网的外层,和任选装饰层,并在模具中在100至150℃的温度下施以变形和压制成夹层结构。
在用于制造汽车内饰、车顶内衬等的泡沫板的分批制造(称作“箱式发泡(box foaming)”)的情况下,制成的泡沫中的合意特征是高吸声。但是,EP 0437787 A1中描述的那类标准配方的泡沫板仅达到中等吸声水平。此外,令人惊讶地,来自该泡沫块的底部区域的泡沫板仅具有明显更低的吸声。当在车顶内衬的制造中使用该泡沫板时,例如,这造成这些车顶内衬的吸声差异,这是不合意的。
根据EP 0437787 A1,可通过使具有70至90重量%的MDI含量的二苯甲烷二异氰酸酯(MDI)和多苯基-多亚甲基多异氰酸酯的混合物(其中12-30重量%为2,4'-二苯甲烷二异氰酸酯且10-30重量%为多苯基-多亚甲基多异氰酸酯)(异氰酸酯组分)与由50至70重量%的具有28至600的羟基值的二-和/或三官能聚氧化烯多元醇、20至35重量%的具有150至440的羟基值的双官能邻苯二甲酸聚酯、2至10重量%的甘油、3.5至7重量%的水、0.3至1重量%的可并入的叔胺催化剂和0.1至2重量%的有机硅泡沫稳定剂构成的多元醇混合物(多元醇组分)反应制造具有25-30千克/立方米的密度的可热塑性变形的硬质PU泡沫。这样的泡沫只有中等吸声。
但是,汽车工业需要更高的吸声水平,因为车内的行驶噪声水平应该尽可能低。同时,绝不能以泡沫加工成例如车顶内衬的简易性为代价实现良好的声性质。
本发明的目的是提供具有极高吸声的主要(>50体积%)开孔的(根据DIN ISO 4590-86)硬质PU泡沫,其可通过冷成形法压制形成汽车内饰。
开孔在本文中是指该泡沫中存在的泡孔的多于50体积%是开孔。
高吸声在本文中是指泡沫块内在800至6350 Hz频率范围内的平均吸声不小于35%,优选不小于40%。
已经令人惊讶地发现,通过使用六官能聚氧化烯多元醇——非常优选与二胺的脂肪酸酰胺,例如妥尔油酸的N,N-二甲基氨基丙基酰胺组合,可以获得由其制成的PU泡沫中的高吸声。此外,来自泡沫块的不同样品的吸声水平几乎没有彼此不同,意味着在泡沫块的整个区域中吸声相似。
本发明因此提供具有>50体积%根据DIN ISO 4590-86的开孔含量并具有高的均匀吸声的开孔的、可冷成形的、固结硬质聚氨酯(PU)泡沫,其可通过使工业多异氰酸酯组分A与组分B反应获得,多异氰酸酯组分A包含
A1) 基于有机多异氰酸酯组分A)计,0至10重量%,优选0.1至8重量%的2,2'-二苯甲烷二异氰酸酯,
A2) 基于有机多异氰酸酯组分A)计,0至30重量%,优选10至25重量%的2,4'-二苯甲烷二异氰酸酯和
A3) 基于有机多异氰酸酯组分A)计,25至75重量%,优选35至55重量%的4,4'-二苯甲烷二异氰酸酯,
组分B构成如下
B1) 基于组分B计,10至70重量%,优选15至35重量%的具有25至110 mg KOH/g,优选25至60 mg KOH/g的羟基值和2至4的数均官能度的聚氧化烯多元醇,
B2) 基于组分B计,0至20重量%,优选5至20重量%的具有150至550 mg KOH/g的羟基值和2的官能度的聚氧化烯多元醇,
B3) 基于组分B计,10至66重量%,优选15至48重量%的具有300至900 mg KOH/g,优选370至570 mg KOH/g的羟基值和2.5至4的数均官能度的聚氧化烯多元醇,
B4) 基于组分B计,2.5至25重量%,优选5至20重量%的具有25至195 mg KOH/g的羟基值和6的官能度的聚氧化烯多元醇,
B5) 基于组分B计,0至15重量%的具有195至500 mg KOH/g的羟基值和2至5的数均官能度的低聚聚酯多元醇,
B6) 基于组分B计,0至8重量%的甘油,
B7) 基于组分B计,2.5至8重量%,优选5至7重量%的水,
B8) 基于组分B计,0.5至4重量%的催化剂,
B9) 任选辅助剂和/或辅佐剂,
NCO指数为85至135,优选90至120。
NCO指数是NCO基团数与NCO-反应性基团数的比率,乘以100。
本发明的硬质聚氨酯泡沫优选具有15至65千克/立方米,更优选19至24千克/立方米的根据DIN 53420的密度。
本发明的硬质聚氨酯泡沫优选在组分B8)中包含基于可再生原材料,更优选脂肪酸的催化剂。
本发明的硬质PU泡沫优选以分批法制造。它们优选用于制造汽车内饰,更特别是车顶内衬和柱饰板。它们也可以用作建筑物的内部和外部或展会建筑中的吸声材料,在这种情况下防火性能应满足建筑材料种类的要求(DIN 4102-1或DIN EN 13501-1)。为此,如果必要,应另外加入合适的阻燃剂(磷酸三(1-氯-2-丙基)酯、磷酸三(1,3-二氯异丙基)酯、磷酸三乙酯、多溴化聚氧化烯多元醇、磷酸三(2-氯乙基)酯、磷酸三甲苯酯、磷酸三苯酯、间苯二酚双(磷酸二苯酯)、双酚A双(磷酸二苯酯))。
优选通过将多元醇制剂B与多异氰酸酯组分A通常以100:150至100:200,优选至100:165的重量比例混合来制造本发明的泡沫。通常使用低压发泡机,例如Cannon C 300或Hennecke HK 5000 R实现这种混合。优选分批制造泡沫块,将可发泡混合物倒入尺寸适当的箱中,其底面积取决于汽车内衬的稍后尺寸。
吸声的测定
在昆特管中测量该泡沫的吸声。在层厚度1厘米的泡沫上进行测量。试样的直径为3厘米并需要精确配合到昆特管中。
在昆特管中,使经过管的声波经过试样并被该试样从无间隙地位于该试样后的声学硬墙反射。使用布置在声源和反射壁之间的两个扩音器,通过捕集振幅信息和相位信息,可以测定入射声波和相关反射声波之间的振幅比。这种振幅比给出吸收度。
所用多异氰酸酯组分优选包含4,4'-、2,4'-和2,2'-二苯甲烷二异氰酸酯和多苯基-多亚甲基多异氰酸酯的混合物(粗制MDI)。
在25至110 mg KOH/g, 更优选25至60 mg KOH/g的羟基值范围内的聚氧化烯多元醇优选用作组分B1),其优选可通过环氧乙烷和/或环氧丙烷与三元醇,例如甘油、三羟甲基丙烷或与二元醇,如乙二醇、二乙二醇、1,2-或1,3-丙二醇、1,4-丁二醇、异山梨醇、新戊二醇、二溴新戊二醇、双酚等反应获得。
在150至550 mg KOH/g的羟基值范围内的双官能聚氧化烯多元醇用作组分B2),其优选可通过环氧丙烷与多元醇,如乙二醇、二乙二醇、1,2-或1,3-丙二醇、1,4-丁二醇、异山梨醇、新戊二醇、二溴新戊二醇、双酚等的反应获得。
在300至900 mg KOH/g,优选370至570 mg KOH/g的羟基值范围内的聚氧化烯多元醇用作组分B3),其优选可通过环氧丙烷与二醇,如乙二醇、二乙二醇、1,2-或1,3-丙二醇和1,4-丁二醇,和与甘油和1,1,1-三羟甲基丙烷等的反应获得。
在25至195 mg KOH/g的羟基值范围内的六官能聚氧化烯多元醇用作组分B4),其优选可通过环氧乙烷和/或环氧丙烷与山梨糖醇的反应获得。
所用催化剂B8)包括加速含反应性氢原子(更特别是羟基)的反应组分、水与有机多异氰酸酯a)的反应的化合物。所考虑的催化剂包括有机金属化合物,优选有机锡化合物,如有机羧酸的锡(II)盐,例如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)、月桂酸锡(II),和有机羧酸的二烷基锡(IV)盐,例如二乙酸二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡、二乙酸二辛基锡以及叔胺,如三乙胺、三丁胺、二甲基环己基胺、二甲基苄基胺、N-甲基咪唑、N-甲基-、N-乙基-和 N-环己基吗啉、N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基丁二胺、N,N,N',N'-四甲基己-1,6-二胺、五甲基二亚乙基三胺、四甲基二氨基乙基醚、双(二甲基氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环[3.3.0]辛烷、1,4-二氮杂双环[2.2.2]辛烷,和链烷醇胺化合物,如三乙醇胺、三异丙醇胺、N-甲基-和N-乙基二乙醇胺和二甲基乙醇胺。另外被考虑作为催化剂的是下列:氧化胺、双(2-二甲基氨基乙基)醚、三(二烷基氨基)-s-六氢三嗪,更特别是三(N,N-二甲基氨基)-s-六氢三嗪,四烷基铵盐,例如N,N,N-三甲基-N-(2-羟丙基)甲酸盐、N,N,N-三甲基-N-(2-羟基丙基)2-乙基己酸盐、氢氧化四烷基铵,如氢氧化四甲基铵,碱金属氢氧化物,如氢氧化钠,碱金属醇盐,如甲醇钠和异丙醇钾,铋盐、钛盐和锌盐,以及具有1至20个C原子和任选OH侧基的脂肪酸的碱金属盐或碱土金属盐。
优选使用异氰酸酯反应性叔胺,例如N,N-二甲基氨基丙基胺、双(二甲基氨基丙基)胺、N,N-二甲基氨基丙基-N'-甲基乙醇胺、二甲基氨基乙氧基乙醇、双(二甲基氨基丙基)氨基-2-丙醇、N,N-二甲基氨基丙基二丙醇胺、N,N,N'-三甲基-N'-羟基乙基-双氨基乙基醚、N,N-二甲基氨基丙基脲、N-(2-羟基丙基)咪唑、N-(2-羟基乙基)咪唑、N-(2-氨基丙基)咪唑、2-((二甲基氨基)乙基)甲基氨基丙醇、1,1'-((3-(二甲基氨基)丙基)亚氨基)双-2-丙醇和/或EP-A 0 629
607中描述的乙酰乙酸乙酯、聚醚多元醇和1-(二甲基氨基)-3-氨基丙烷的反应产物,特别是N,N-二甲基氨基丙基胺的妥尔油酸酰胺盐。
根据本发明也可任选使用的辅助剂和/或辅佐剂B9)的另一些实例是乳化剂、反应阻滞剂、抗老化和风化作用的稳定剂、增塑剂、无机阻燃剂、含磷-和/或含卤素-的有机阻燃剂、具有抑制真菌和抑细菌活性的物质、颜料和染料,以及本身已知的常规有机和无机填料。可给出的乳化剂的实例包括乙氧基化烷基酚、脂肪酸的碱金属盐、硫酸化脂肪酸的碱金属盐、磺酸的碱金属盐,以及脂肪酸和胺的盐。
合适的泡沫稳定剂和乳化剂的实例包括硅氧烷-聚氧化烯共聚物、有机聚硅氧烷、乙氧基化脂肪醇、烷基酚和蓖麻油酯和蓖麻醇酸酯,和基于脂肪酸的甜菜碱、胺和氧化胺。
活性开孔剂包括例如石蜡、聚丁二烯、脂肪醇和任选聚醚改性的二甲基聚硅氧烷。
例如在Kunststoff-Handbuch,
Polyurethane, 第VII卷,
Carl Hanser Verlag, Munich,
Vienna, 第2版,
1983中描述了上述辅助剂和辅佐剂的使用模式和作用模式的进一步细节。
本发明的开孔的、可冷成形的、固结硬质聚氨酯(PU)泡沫优选作为吸声材料用在复合材料中。
本发明的开孔的、可冷成形的、固结硬质聚氨酯(PU)泡沫优选用于制造汽车内饰,更特别是车顶内衬和柱饰板。
下列实施例用于更详细阐释本发明。
本发明的实施例和对比例
:
所用产品:
来自Momentive
Performance Materials的Niax®
Silicone SR 234和Niax®
Silicone SR 272,Si泡沫稳定剂。
硬质
PU
泡沫的制造
本发明的实施例
1
将下述的混合物(组分B):
22.7重量份的基于甘油/环氧丙烷/环氧乙烷的聚醚醇(B1),OH值35 mg KOH/g,官能度3,
10.0重量份的基于1,2-丙二醇的聚醚醇(B2),OH值260 mg KOH/g,官能度2,
41.4重量份的基于甘油的聚醚醇(B3),OH值450 mg KOH/g,官能度3,
8.8重量份的基于山梨糖醇/环氧丙烷/环氧乙烷的聚醚醇(B4),OH值28.5 mg KOH/g,官能度6,
6.0重量份的甘油(B6)
3.0重量份的妥尔油酸和N,N-二甲基氨基丙基胺的反应产物(B8)
1.5重量份的有机硅泡沫稳定剂(B9)(来自Momentive Performance
Materials的Niax® Silicone
SR 272),
6.50重量份的水(B7)和
0.10重量份的来自ISL-Chemie of
Kürten, DE的Isopur N黑色膏(B9)
与
165重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)混合。A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯。
对比例
1
将下述的混合物(组分B):
31.0重量份的基于甘油/环氧丙烷/环氧乙烷的聚醚醇(B1),OH值28 mg KOH/g,官能度3,
35.05重量份的基于三羟甲基丙烷/环氧丙烷的聚醚醇(B3),OH值550 mg KOH/g,官能度3,
12.0重量份的基于丙二醇/环氧丙烷的聚醚醇(B2),OH值512 mg KOH/g,官能度2,
15.0重量份的邻苯二甲酸酐、二乙二醇和环氧乙烷的反应产物,OH值300 mg KOH/g,官能度2
(B5),
0.50重量份的1,1'-((3-(二甲基氨基)丙基)亚氨基)双-2-丙醇和0.05重量份的双(2-二甲基氨基乙基)醚 (B8),
0.20重量份的有机硅泡沫稳定剂(来自Momentive
Performance Materials的Niax®
Silicone SR 234)(B9),
5.80重量份的水(B7)和
0.50重量份的来自ISL-Chemie of
Kürten, DE的Isopur N黑色膏(B9)
与
175重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)混合。A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯。
为了测量该泡沫的声性质,制造块尺寸为30 x 30 x 30 cm的块。另外,为了评估声性质的均匀性,制造尺寸为1.0 x 1.0 x 0.8至1.0 m的块和尺寸为1.4 x 2.2 x 1.0
m的块。测试和评估板厚度为10毫米和14毫米的泡沫板。
为此,切下泡沫块(1.4 x 2.2 x 1.0 m)的底部15厘米。这一区域可能具有由反应结束时的泡孔打开造成的缺陷,并因此较不合适。此外,切下泡沫块的顶部(大约10厘米)。将泡沫块切成板,然后从底部、中部和顶部区域获取板,并在昆特管中测量声性质。
下表含有来自本发明的实施例1(泡沫块:1.0 x 1.0 x 0.8至1.0 m)的吸声。该表指示获取测量试样的位置。在本文中,CT是指“边角顶部(corner top)”,CM“边角中部(middle)”,CB“边角底部(corner bottom)”,MT“中间顶部(middle top)”,MM“中间中部(middle middle)”,和MB“中间底部(middle bottom)”。
泡沫的物理性质也变得更均匀。下表含有来自本发明的实施例1(泡沫块:1.0 x
1.0 x 0.8至1.0 m)的物理性质。
下表含有来自对比例1(泡沫块:1.0 x 1.0 x 0.8至1.0 m)的吸声。
下表含有来自对比例1(泡沫块:1.0 x 1.0 x 0.8至1.0 m)的泡沫的物理性质。
已发现,六官能聚醚的使用带来更高的平均吸声以及如标准偏差所示的改进的均匀性。毛密度、开孔含量、拉伸强度和致断伸长中的标准偏差表明,就这些性质而言,六官能聚醚的使用也带来改进的均匀性。
混合比的改变(本发明的实施例2)
通过在尺寸大约1升的纸板烧杯中将包含下述的组分B)的混合物:
22.5重量份的基于甘油/环氧丙烷/环氧乙烷的聚醚醇(B1),OH值35 mg KOH/g,官能度3,
10.0重量份的基于1,2-丙二醇的聚醚醇(B2),OH值260 mg KOH/g,官能度2,
41.1重量份的基于甘油的聚醚醇(B3),OH值450 mg KOH/g,官能度3,
8.7重量份的基于山梨糖醇/环氧丙烷/环氧乙烷的聚醚醇(B4),OH值28,5 mg KOH/g,官能度6,
5.95重量份的甘油(B6),
3.1重量份的妥尔油酸和N,N-二甲基氨基丙基胺的反应产物(B8),
1.5重量份的有机硅泡沫稳定剂(B9)(来自Momentive Performance
Materials的Niax®
Silicone SR 272)和0.2重量份的有机硅泡沫稳定剂(B9)(来自Momentive
Performance Materials的Niax®
Silicone SR 234),
6.45重量份的水(B7),和
0.50重量份的Isopur N黑色膏(B9),
与
I) 160重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)[A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯],或
II) 180重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)[A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯],或
III) 200重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)[A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯]
使用带有直径6.5厘米的搅拌器板的Pendraulic搅拌器在4200
rpm下混合21秒,制造下列泡沫。
下表含有来自对比例1(泡沫块:大约0.3 x 0.3 x 0.3
m)的吸声。随着混合比升高,高度略微改变并从31.8厘米降至29.0厘米。从泡沫的中部获取试样。
2a | 2b | 2c | |
每100克多元醇的异氰酸酯 | 160 g | 180 g | 200 g |
平均800-6350 Hz | 42% | 46% | 44% |
从该表中可以看出,在所有混合比下获得高吸声。
本发明的实施例
3
混合物(组分B)
组分 | 配方3a | 配方3b | 配方3c |
基于山梨糖醇/环氧丙烷/环氧乙烷的聚醚醇(B4),OH值28.5 mg KOH/g,官能度6 | 15.00 | 20.00 | 31.20 |
基于甘油/环氧丙烷/环氧乙烷的聚醚醇(B1),OH值35 mg KOH/g,官能度3 | 16.20 | 11.20 | |
基于1,2-丙二醇的聚醚醇(B2),OH值260 mg KOH/g,官能度2 | 10.00 | 10.00 | 10.00 |
基于甘油的聚醚醇(B3),OH值450 mg KOH/g,官能度3 | 41.10 | 41.10 | 41.10 |
甘油(B6) | 5.95 | 5.95 | 5.95 |
水(B7) | 6.45 | 6.45 | 6.45 |
Niax® Silicone SR 272 (B9) | 1.50 | 1.50 | 1.50 |
Niax® Silicone SR 234 (B9) | 0.20 | 0.20 | 0.20 |
Isopur N黑色膏 | 0.50 | 0.50 | 0.50 |
妥尔油酸和二甲基氨基丙基胺的反应产物(B8) | 3.10 | 3.10 | 3.10 |
与160重量份的具有60重量%的二苯甲烷二异氰酸酯异构体含量和31.8重量%的NCO含量的二苯甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(A组分)混合[A1):基于有机多异氰酸酯组分A)计,13.9重量%的2,4'-二苯甲烷二异氰酸酯和A2):基于有机多异氰酸酯组分A)计,44.7重量%的4,4'-二苯甲烷二异氰酸酯]。
下表显示吸声(泡沫块:大约0.3 x 0.3 x 0.3 m)。
Claims (5)
1.开孔的、可冷成形的、固结硬质聚氨酯(PU)泡沫,其具有>50体积%根据DIN ISO 4590-86的开孔含量并具有高的均匀吸声,其可通过有机多异氰酸酯组分A与组分B的反应获得,多异氰酸酯组分A包含
A1) 基于有机多异氰酸酯组分A)计,0至10重量%,优选0.1至8重量%的2,2'-二苯甲烷二异氰酸酯,
A2) 基于有机多异氰酸酯组分A)计,0至30重量%,优选10至25重量%的2,4'-二苯甲烷二异氰酸酯和
A3) 基于有机多异氰酸酯组分A)计,25至75重量%,优选35至55重量%的4,4'-二苯甲烷二异氰酸酯,
组分B构成如下
B1) 基于组分B计,10至70重量%的具有25至110 mg KOH/g的羟基值和2至4的数均官能度的聚氧化烯多元醇,
B2) 基于组分B计,0至20重量%的具有150至550 mg KOH/g的羟基值和2的官能度的聚氧化烯多元醇,
B3) 基于组分B计,10至66重量%的具有300至900 mg KOH/g的羟基值和2.5至4的数均官能度的聚氧化烯多元醇,
B4) 基于组分B计,2.5至25重量%的具有25至195 mg KOH/g的羟基值和6的官能度的聚氧化烯多元醇,
B5) 基于组分B计,0至15重量%的具有195至500 mg KOH/g的羟基值和2至5的数均官能度的低聚聚酯多元醇,
B6) 基于组分B计,0至8重量%的甘油,
B7) 基于组分B计,2.5至8重量%的水,
B8) 基于组分B计,0.5至4重量%的催化剂,
B9) 任选辅助剂和/或辅佐剂,
NCO指数为85至135。
2.根据权利要求1的硬质聚氨酯泡沫,其具有15至65千克/立方米,优选19至24千克/立方米的根据DIN 53420的密度。
3.根据权利要求1的硬质聚氨酯泡沫,其在组分B8)中包含基于可再生原材料,优选脂肪酸的催化剂。
4.根据权利要求1的开孔的、可冷成形的、固结硬质聚氨酯泡沫作为吸声材料在复合材料中的用途。
5.根据权利要求1的开孔的、可冷成形的、固结硬质聚氨酯泡沫用于制造汽车内饰,更特别是车顶内衬和柱饰板的用途。
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JP2021531351A (ja) * | 2018-03-28 | 2021-11-18 | コベストロ・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・アンド・コー・カーゲー | 低臭気の硬質ポリウレタンフォーム |
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- 2013-03-25 JP JP2016504432A patent/JP6231186B2/ja not_active Expired - Fee Related
- 2013-03-25 CN CN201380075129.2A patent/CN105209512B/zh not_active Expired - Fee Related
- 2013-03-25 EP EP13880683.1A patent/EP2978787A4/en not_active Withdrawn
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CN106832204A (zh) * | 2017-01-05 | 2017-06-13 | 广州特种承压设备检测研究院 | 一种改性聚氨酯屋面保温材料及其制备方法 |
CN110317311A (zh) * | 2018-03-28 | 2019-10-11 | 科思创德国股份有限公司 | 低气味的硬质聚氨酯泡沫 |
CN109593175A (zh) * | 2018-10-23 | 2019-04-09 | 万华化学(宁波)容威聚氨酯有限公司 | 一种全水型半开孔聚氨酯硬泡组合料及其制备方法 |
CN109627418A (zh) * | 2018-12-06 | 2019-04-16 | 上海应用技术大学 | 一种高吸音性聚氨酯汽车地毯的制备方法 |
CN111533869A (zh) * | 2020-06-08 | 2020-08-14 | 上海玓墨化工科技有限公司 | 环保型热塑性聚氨酯泡沫用组合物及其应用 |
CN113004483A (zh) * | 2021-03-31 | 2021-06-22 | 华南理工大学 | 一种阻燃型硬质聚氨酯泡沫吸声材料及其全水发泡制备工艺 |
CN113004483B (zh) * | 2021-03-31 | 2022-03-29 | 华南理工大学 | 一种阻燃型硬质聚氨酯泡沫吸声材料及其全水发泡制备工艺 |
CN115651148A (zh) * | 2022-11-02 | 2023-01-31 | 佳化化学科技发展(上海)有限公司 | 一种低密度全水发泡聚氨酯硬质泡沫 |
Also Published As
Publication number | Publication date |
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US9777104B2 (en) | 2017-10-03 |
US20160046758A1 (en) | 2016-02-18 |
WO2014153701A1 (en) | 2014-10-02 |
JP2016514739A (ja) | 2016-05-23 |
JP6231186B2 (ja) | 2017-11-15 |
CN105209512B (zh) | 2018-01-09 |
EP2978787A4 (en) | 2016-11-02 |
EP2978787A1 (en) | 2016-02-03 |
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