CN103210023A - 基于储存稳定的反应性或高反应性聚氨酯组合物的预浸料 - Google Patents
基于储存稳定的反应性或高反应性聚氨酯组合物的预浸料 Download PDFInfo
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- CN103210023A CN103210023A CN2011800562465A CN201180056246A CN103210023A CN 103210023 A CN103210023 A CN 103210023A CN 2011800562465 A CN2011800562465 A CN 2011800562465A CN 201180056246 A CN201180056246 A CN 201180056246A CN 103210023 A CN103210023 A CN 103210023A
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- ammonium
- polyurethane composition
- aforementioned
- dye
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000004814 polyurethane Substances 0.000 title claims abstract description 75
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 75
- 239000000049 pigment Substances 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims description 40
- 239000000975 dye Substances 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 239000000758 substrate Substances 0.000 claims description 32
- -1 isocyanuric acid ester Chemical class 0.000 claims description 29
- 239000005056 polyisocyanate Substances 0.000 claims description 24
- 229920001228 polyisocyanate Polymers 0.000 claims description 24
- 239000000835 fiber Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000011159 matrix material Substances 0.000 claims description 19
- 230000009257 reactivity Effects 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 239000002131 composite material Substances 0.000 claims description 14
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 11
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 6
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 150000002118 epoxides Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- HKKDKUMUWRTAIA-UHFFFAOYSA-N nitridooxidocarbon(.) Chemical compound [O]C#N HKKDKUMUWRTAIA-UHFFFAOYSA-N 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 238000007348 radical reaction Methods 0.000 claims description 4
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 3
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 3
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 3
- DOFHXXBIPRPYSZ-UHFFFAOYSA-N [cyclohexyl(isocyanato)methyl]cyclohexane Chemical class C1CCCCC1C(N=C=O)C1CCCCC1 DOFHXXBIPRPYSZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000980 acid dye Substances 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000000034 method Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000004744 fabric Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 239000003365 glass fiber Substances 0.000 description 7
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-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 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000004917 carbon fiber Substances 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000002657 fibrous material Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920000271 Kevlar® Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- OBBQDLHBLQTARQ-UHFFFAOYSA-N hexan-1-amine;hydrate Chemical compound [OH-].CCCCCC[NH3+] OBBQDLHBLQTARQ-UHFFFAOYSA-N 0.000 description 4
- 239000004761 kevlar Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 3
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical group O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- YBNOFFZAWGMPOL-UHFFFAOYSA-N CCC(CC)(CC)C(C)O.N Chemical compound CCC(CC)(CC)C(C)O.N YBNOFFZAWGMPOL-UHFFFAOYSA-N 0.000 description 2
- ODEVNESUDCCCBZ-UHFFFAOYSA-N CCC1=C(CC)C(CC)=C(CC)C=C1.N Chemical compound CCC1=C(CC)C(CC)=C(CC)C=C1.N ODEVNESUDCCCBZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 241000196324 Embryophyta Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- DRDGCDWNOIBRFQ-UHFFFAOYSA-N [OH-].[NH4+].C(CCCCC)CO Chemical class [OH-].[NH4+].C(CCCCC)CO DRDGCDWNOIBRFQ-UHFFFAOYSA-N 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WDSYFPPDMKLHFL-UHFFFAOYSA-M azanium benzyl(triethyl)azanium dihydroxide Chemical compound [OH-].[NH4+].[OH-].C(C1=CC=CC=C1)[N+](CC)(CC)CC WDSYFPPDMKLHFL-UHFFFAOYSA-M 0.000 description 2
- UHHXUPJJDHEMGX-UHFFFAOYSA-K azanium;manganese(3+);phosphonato phosphate Chemical compound [NH4+].[Mn+3].[O-]P([O-])(=O)OP([O-])([O-])=O UHHXUPJJDHEMGX-UHFFFAOYSA-K 0.000 description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 239000000919 ceramic Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- KCUNNSOHQKQZNQ-UHFFFAOYSA-N decylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[NH3+] KCUNNSOHQKQZNQ-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 2
- LUSRALAAIUPSEY-UHFFFAOYSA-N neurine Chemical compound [O-].C[N+](C)(C)C=C LUSRALAAIUPSEY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- SDPBQTFSSSPDBS-UHFFFAOYSA-N pentan-1-amine;hydrate Chemical compound [OH-].CCCCC[NH3+] SDPBQTFSSSPDBS-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010248 power generation Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
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- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
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Abstract
本发明涉及用颜料或染料制品着色的基于储存稳定的反应性或高反应性聚氨酯组合物的预浸料。
Description
本发明涉及用颜料-或染料制品着色的基于储存稳定的反应性或高反应性聚氨酯组合物的预浸料。
从DE 102009001793、DE 102009001806、DE 10201029355已知基于储存稳定的反应性或高反应性聚氨酯组合物的预浸料。
本发明的目的是使得制造基于储存稳定的反应性或高反应性聚氨酯组合物的经着色的预浸料成为可能。
用适合于粉末漆用途的在预浸料制造过程中已存在于基于储存稳定的反应性或高反应性聚氨酯组合物的基质材料组合物中的颜料或染料制品实现所述目的。
本发明的主题是有色预浸料,其基本上如下构成
A) 至少一种纤维状载体
和
B) 至少一种反应性或高反应性聚氨酯组合物作为基质材料,
其中所述聚氨酯组合物基本上含有作为粘合剂的具有异氰酸酯反应性官能团的聚合物b)和作为固化剂的内部封端的和/或用封端剂封端的二-或多异氰酸酯a)的混合物,
其中所述基质材料另外包含
1. 粒径<150纳米的颜料
和/或
2. 染料。
原则上可按照任何方法实施预浸料的制造。
以合适的方式,通过粉末浸渍,优选通过喷粉法将包含染料和/或颜料的粉状聚氨酯组合物B)施加到载体上。流化床烧结法、拉挤成型或喷涂法也可行。优选通过喷粉法将粉末(整体或一部分)施加到纤维状载体上,例如施加到玻璃-、碳-或芳族聚酰胺-纤维网格布(Gelege)/织物的条带上,然后固定。为避免粉末损失,优选直接在喷粉程序后将该用粉末加载的纤维状载体在加热段中(例如用IR辐射器)加热,以使颗粒烧结,在此过程中不应超过80至100℃的温度,以防止高反应性基质材料的反应。这些预浸料可以按需要组合和切割成不同形式。
也可以按照直接熔体浸渍法实施预浸料的制造。预浸料的直接熔体浸渍法的原理在于,首先由其各组分在熔体中制造包含染料和/或颜料的反应性或高反应性聚氨酯组合物B)。然后将包含染料和/或颜料的反应性聚氨酯组合物B)的这种熔体直接施加到纤维状载体A)上,换言之用B)的熔体进行纤维状载体A)的浸渍。此后,可以在稍后的时间将冷却的可储存预浸料进一步加工成复合材料。通过根据本发明的直接熔体浸渍法,由于该液体低粘反应性聚氨酯组合物极好润湿载体的纤维,造成纤维状载体的极好浸渍。
也可以使用溶剂进行预浸料的制造。该预浸料制造法的原理随之在于,首先在合适的共同的溶剂中由其各组分制造包含染料和/或颜料的反应性或高反应性聚氨酯组合物B)的溶液或分散体。然后将反应性聚氨酯组合物B)的这种溶液或分散体直接施加到纤维状载体A)上,由此该纤维状载体被这种溶液浸透/浸渍。随后,除去溶剂。优选通过例如热处理或施加真空在低温,优选< 100℃下完全除去溶剂。此后,可以在稍后的时间将再脱除溶剂的该可储存预浸料进一步加工成复合材料。通过本发明的方法,由于该反应性聚氨酯组合物的溶液极好润湿载体的纤维,造成纤维状载体的极好浸渍。
作为适用于本发明的方法的溶剂,可以使用不与反应性聚氨酯组合物反应、对所用反应性聚氨酯组合物的各组分具有足够的溶解能力并可以在溶剂脱除工艺步骤过程中从浸透反应性聚氨酯组合物的预浸料中除去直到微小的痕量(<0.5重量%)的所有非质子液体,其中分离的溶剂的再循环是有利的。
例如,在此可以提及:酮(丙酮、甲乙酮、甲基异丁基酮、环己酮)、醚(四氢呋喃)、酯(乙酸正丙酯、乙酸正丁酯、乙酸异丁酯、碳酸-1,2-异丙二醇酯、丙二醇甲醚乙酸酯)。
在冷却至室温后,根据本发明的预浸料具有在室温下的极高储存稳定性,只要基质材料具有至少40℃的Tg。根据所含的反应性聚氨酯组合物,这为在室温下至少几天,但该预浸料通常在40℃和更低温度下储存稳定数周。由此制成的预浸料不是粘稠的并因此非常容易操作和进一步加工。根据本发明使用的反应性或高反应性聚氨酯组合物因此表现出在纤维状载体上的极好附着和分布。
在预浸料进一步加工成复合材料(例如通过在升高的温度下压制)的过程中,在通过反应性或高反应性聚氨酯组合物在升高的温度下的交联反应而发生胶凝或整个聚氨酯基质完全固化之前,由于在这种情况下该液态低粘反应性或高反应性聚氨酯组合物在交联反应之前极好润湿载体的纤维,造成纤维状载体的极好浸渍。
可以按需要将如此制成的预浸料组合和切割成不同形式。
为将预浸料合并成单一复合材料和为使基质材料交联成基质,裁剪预浸料,任选缝合或另外固定并在合适的模具中在压力和任选施加真空下压制。在本发明范围内,根据固化时间,在使用反应性基质材料(方案I)时在大约160℃以上的温度下或在使用带有合适的催化剂的高反应性基质材料(方案II)时在100℃以上的温度下进行由预浸料制造复合材料的操作。
根据所用的反应性或高反应性聚氨酯组合物的组成和任选添加的催化剂,可以在宽范围内改变复合部件制造中的交联反应的速率以及基质的性质。
作为基质材料,在本发明范围内,被定义为用于制造预浸料的反应性或高反应性聚氨酯组合物并在预浸料的描述中被定义为通过本发明的方法施加到纤维上的还有反应性或高反应性的聚氨酯组合物。
基质被定义为在该复合材料中交联的由反应性或高反应性聚氨酯组合物构成的基质材料。
载体
在本发明中的纤维状载体由纤维状材料(通常也称作增强纤维)构成。通常,构成该纤维的任何材料都是合适的,但优选使用玻璃、碳、塑料,例如聚酰胺(芳族聚酰胺)或聚酯、天然纤维或矿物纤维材料,如玄武岩纤维或陶瓷纤维(基于氧化铝和/或氧化硅的氧化物纤维)的纤维状材料。也可以使用纤维类型的混合物,例如芳族聚酰胺-和玻璃纤维、或碳-和玻璃纤维的织物组合。同样可以用不同纤维状载体的预浸料制造混杂复合部件。主要由于其相对低的价格,玻璃纤维是最常用的纤维类型。在此原则上,所有类型的玻璃基增强纤维均是合适的(E-玻璃-、S-玻璃-、R-玻璃-、M-玻璃-、C-玻璃-、ECR-玻璃-、D-玻璃-、AR-玻璃-或中空玻璃纤维)。碳纤维通常用在高性能复合材料中,其中与玻璃纤维相比的较低密度以及同时较高强度也是重要因素。碳纤维(也称作碳纤维)是由含碳原材料制成的工业生产的纤维,其通过热解转化成石墨状构造的碳。区分各向同性和各向异性类型:各向同性纤维仅具有低强度和较低工业重要性,各向异性纤维表现出高强度和刚度同时小的断裂伸长。在此,获自植物和动物材料的所有织物纤维和纤维材料(例如木材-、纤维素-、棉-、大麻-、黄麻-、亚麻-、西沙尔麻-、竹纤维)被称为天然纤维。也与碳纤维类似,芳族聚酰胺纤维具有负的热膨胀系数,即在加热时变短。它们的比强度及其弹性模量明显低于碳纤维。与基质树脂的正膨胀系数结合,可以制造高尺寸稳定的部件。与碳纤维增强塑料相比,芳族聚酰胺纤维复合材料的抗压强度明显更低。芳族聚酰胺纤维的已知品牌是来自DuPont的Nomex?和Kevlar?,或来自Teijin的Teijinconex?、Twaron?和Technora?。由玻璃纤维、碳纤维、芳族聚酰胺纤维或陶瓷纤维制成的载体是特别合适和优选的。该纤维状材料是织物平面构型物品。非织造织物的纺织平面构型物品,以及所谓的针织物,如针织品和纬编织物(Gestricke),以及非针织缕纱(Gebinde),如织物(Gewebe)、网格布或编织物(Geflechte)是合适的。此外,作为载体区分长纤维-和短纤维材料。根据本发明,粗纱和纱线同样是合适的。所有所述材料都适合作为本发明范围内的纤维状载体。在“Composites Technologien, Paolo Ermanni (第4版), Script zur Vorlesung ETH Zürich, 2007年8月, 第7章”中包含增强材料的综述。
基质材料
原则上,所有通常在室温下也储存稳定的反应性或高反应性聚氨酯组合物适合作为基质材料。根据本发明,合适的聚氨酯组合物由具有可与NCO基团反应的官能团的聚合物b)(粘合剂),也称作树脂和暂时失活,换言之内部封端和/或用封端剂封端的二-或多异氰酸酯,也称作固化剂a)(组分a))的混合物构成。
作为聚合物b)(粘合剂)的官能团,羟基、氨基和硫醇基是合适的,它们与游离异氰酸酯基团加成反应并由此交联和固化聚氨酯组合物。该粘合剂组分必须具有固体树脂性质(玻璃化温度高于室温)。作为粘合剂合适的是具有OH值为20至500毫克KOH/克且平均摩尔质量为250至6000克/摩尔的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯。特别优选具有OH值为20至150毫克KOH/克且平均分子量为500至6000克/摩尔的含羟基的聚酯或聚丙烯酸酯。当然,也可以使用这样的聚合物的混合物。如此选择具有所述官能团的聚合物b)的量以至于在组分b)的每个官能团上消耗组分a)的0.6至2 NCO当量或0.3至1个脲二酮基团。
作为固化剂组分a),使用被封端剂封端的或内部封端(脲二酮)的二-和多异氰酸酯。
根据本发明使用的二-和多异氰酸酯可以由任意芳族、脂族、脂环族和/或(环)脂族二-和/或多异氰酸酯构成。
作为芳族二-或多异氰酸酯,原则上,所有已知的芳族化合物都合适。特别合适的是1,3-和1,4-苯二异氰酸酯、1,5-萘二异氰酸酯、联甲苯胺二异氰酸酯、2,6-甲苯二异氰酸酯、2,4-甲苯二异氰酸酯(2,4-TDI)、2,4‘-二苯基甲烷二异氰酸酯(2,4‘-MDI)、4,4‘-二苯基甲烷二异氰酸酯、单体二苯基甲烷二异氰酸酯(MDI)和低聚二苯基甲烷二异氰酸酯(聚合MDI)的混合物、苯二亚甲基二异氰酸酯、四甲基苯二亚甲基二异氰酸酯和三异氰酸根合甲苯。
合适的脂族二-或多异氰酸酯有利地在直链或支链亚烷基残基中具有3至16个碳原子,优选4至12个碳原子,且合适的脂环族或(环)脂族二异氰酸酯有利地在环亚烷基残基中具有4至18个碳原子,优选6至15个碳原子。(环)脂族二异氰酸酯被本领域技术人员充分理解为同时环状和脂族键合的NCO基团,例如在异佛尔酮二异氰酸酯中就是这样的情况。相反,脂环族二异氰酸酯被理解为是指仅具有直接键合到脂环族环上的NCO基团的那些,例如H12MDI。实例是环己烷二异氰酸酯、甲基环己烷二异氰酸酯、乙基环己烷二异氰酸酯、丙基环己烷二异氰酸酯、甲基二乙基环己烷二异氰酸酯、丙烷二异氰酸酯、丁烷二异氰酸酯、戊烷二异氰酸酯、己烷二异氰酸酯、庚烷二异氰酸酯、辛烷二异氰酸酯、壬烷二异氰酸酯、壬烷三异氰酸酯,如4-异氰酸根合甲基-1,8-辛烷二异氰酸酯(TIN)、癸烷二-和三异氰酸酯、十一烷二-和-三异氰酸酯和十二烷二-和-三异氰酸酯。
优选异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、二异氰酸根合二环己基甲烷(H12MDI)、2-甲基戊烷二异氰酸酯(MPDI)、2,2,4-三甲基六亚甲基二异氰酸酯/2,4,4-三甲基六亚甲基二异氰酸酯(TMDI)、降冰片烷二异氰酸酯(NBDI)。非常特别优选使用IPDI、HDI、TMDI和/或H12MDI,其中也可使用异氰脲酸酯。4-甲基-环己烷-1,3-二异氰酸酯、2-丁基-2-乙基戊亚甲基二异氰酸酯、3(4)-异氰酸根合甲基-1-甲基环己基异氰酸酯、2-异氰酸根合丙基环己基异氰酸酯、2,4‘-亚甲基双(环己基)二异氰酸酯、1,4-二异氰酸根合-4-甲基-戊烷也合适。
当然,也可以使用二-和多异氰酸酯的混合物。
此外,优选使用可由所述二-或多异氰酸酯或其混合物通过用氨基甲酸酯-、脲基甲酸酯-、脲-、缩二脲-、脲二酮-、酰胺-、异氰脲酸酯-、碳二亚胺-、脲酮亚胺-、噁二嗪三酮-或亚氨基噁二嗪二酮结构连接制成的低聚或多异氰酸酯。特别合适的是异氰脲酸酯,特别是得自IPDI和HDI的。
根据本发明使用的多异氰酸酯是封端的。外部封端剂,例如乙酰乙酸乙酯、二异丙胺、甲基乙基酮肟、丙二酸二乙酯、ε-己内酰胺、1,2,4-三唑、苯酚或取代酚和3,5-二甲基吡唑可用于此。
优选使用的固化剂组分是含有异氰脲酸酯基团和ε-己内酰胺封端的异氰酸酯结构的IPDI加合物。
内部封端也可行并优选使用。通过经由脲二酮结构形成二聚体实现内部封端,所述脲二酮结构在升高的温度下又裂解成为最初存在的异氰酸酯结构并因此开始与粘合剂交联。
任选地,该反应性聚氨酯组合物可含有另外的催化剂。这些是0.001 - 1重量%的量的有机金属催化剂,例如二月桂酸二丁基锡(DBTL)、辛酸锡、新癸酸铋或叔胺,例如1,4-二氮杂双环[2.2.2]-辛烷。这些根据本发明使用的反应性聚氨酯组合物在正常条件下,例如用DBTL催化,自160℃起,通常自大约180℃起固化并被称作方案I。
为了制造反应性聚氨酯组合物,可以以0.05至5重量%的总量添加粉末涂料技术中常见的添加剂,如流平剂,例如聚有机硅或丙烯酸酯,光保护剂,例如位阻胺,或如EP 669 353中描述的其它添加剂。
在本发明范围内,反应性(方案I)是指根据本发明使用的反应性聚氨酯组合物如上所述在自160℃起的温度下,而且根据载体的性质固化。
本发明使用的反应性聚氨酯组合物在正常条件下固化,例如用DBTL催化,自160℃起,通常自大约180℃起固化。根据本发明使用的聚氨酯组合物用于固化的时间通常在5至60分钟内。
在本发明中优选使用由含有反应性的脲二酮基团的聚氨酯组合物B)制成的基质材料B),其基本上含有
a) 至少一种含有脲二酮基团的固化剂,基于脂族、(环)脂族或脂环族的含有脲二酮基团的多异氰酸酯和含羟基的化合物的加聚化合物,其中该固化剂在40℃以下以固体形式存在且在125℃以上以液体形式存在,并具有小于5重量%的游离NCO含量和3-25重量%的脲二酮含量,
b) 至少一种含羟基的聚合物,其在40℃以下以固体形式存在且在125℃以上以液体形式存在,并具有20至200毫克KOH/克之间的OH值,
c) 任选至少一种催化剂,
d) 任选地,由聚氨酯化学已知的助剂和添加剂,
以使这两种组分a)和b)以下述比率存在,即在组分b)的每个羟基上消耗组分a)的0.3至1个,优选0.45至0.55个脲二酮基团。后者相当于0.9至1.1比1的NCO/OH比。
含有脲二酮基团的多异氰酸酯是公知的并例如描述在US 4,476,054、US 4,912,210、US 4,929,724和EP 417 603中。在J. Prakt. Chem. 336 (1994) 185-200中给出关于异氰酸酯二聚化生成脲二酮的工业相关方法的全面综述。通常,异氰酸酯生成脲二酮的反应在可溶性二聚化催化剂,例如二烷基氨基吡啶、三烷基膦、亚磷酸三酰胺或咪唑存在下进行。所述反应任选在溶剂中,但优选在不存在溶剂的情况下进行,在实现所希望的转化后通过添加催化剂毒物停止该反应。然后通过短程蒸馏除去过量的单体异氰酸酯。如果该催化剂挥发性足够,则可以在脱除单体的过程中从反应混合物中除去催化剂。在这种情况下可放弃添加催化剂毒物。原则上,多种异氰酸酯适用于制造含有脲二酮基团的多异氰酸酯。可以使用上述二-和多异氰酸酯。但是,优选的是任意脂族、脂环族和/或(环)脂族二-和/或多异氰酸酯的二-和多异氰酸酯。根据本发明使用异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、二异氰酸根合二环己基甲烷(H12MDI)、2-甲基戊烷二异氰酸酯(MPDI)、2,2,4-三甲基六亚甲基二异氰酸酯/2,4,4-三甲基六亚甲基二异氰酸酯(TMDI)、降冰片烷二异氰酸酯(NBDI)。非常特别优选使用IPDI、HDI、TMDI和/或H12MDI,其中也可以使用异氰脲酸酯。
非常特别优选使用IPDI和/或HDI用于所述基质材料。这些含有脲二酮基团的多异氰酸酯生成含有脲二酮基团的固化剂a)的反应包括游离NCO基团与作为增链剂的含羟基的单体或聚合物,例如聚酯、聚硫醚、聚醚、聚己内酰胺、聚环氧化物、聚酯酰胺、聚氨酯或低分子量二-、三-和/或四元醇和任选作为链终止剂的单胺和/或一元醇的反应,并已经经常被描述(EP 669 353、EP 669 354、DE 30 30 572、EP 639 598或EP 803 524)。
优选的具有脲二酮基团的固化剂a)具有小于5重量%的游离NCO含量和3至25重量%,优选6至18重量%的脲二酮基团含量(作为C2N2O2计算,分子量84)。聚酯和单体二元醇是优选的。除脲二酮基团外,该固化剂还可具有异氰脲酸酯-、缩二脲-、脲基甲酸酯-、氨基甲酸酯-和/或脲-结构。
对含羟基的聚合物b)而言,优选使用具有OH值为20 – 200毫克KOH/克的聚酯、聚醚、聚丙烯酸酯、聚氨酯和/或聚碳酸酯。特别优选使用在40℃以下以固体形式存在和在125℃以上以液体形式存在的具有OH值为30 - 150,平均分子量为500 - 6000克/摩尔的聚酯。这样的粘合剂已经描述在例如EP 669 354和EP 254 152中。当然,也可以使用这样的聚合物的混合物。如此选择含羟基的聚合物b)的量,以至于在组分b)的每个羟基上消耗组分a)的0.3至1,优选0.45至0.55个脲二酮基团。任选地,在本发明的反应性聚氨酯组合物B)中可含有另外的催化剂c)。这些是0.001 - 1重量%的量的有机金属催化剂,例如二月桂酸二丁基锡、辛酸锌、新癸酸铋或叔胺,例如1,4-二氮杂双环[2.2.2]辛烷。这些根据本发明使用的反应性聚氨酯组合物在正常条件下,例如用DBTL催化,自160℃起,通常自大约180℃起固化并被称作方案I。
为了制造本发明的反应性和高反应性聚氨酯组合物,可以以0.05至5重量%的总量添加粉末涂料技术中常见的添加剂如流平剂,例如聚有机硅或丙烯酸酯,光保护剂,例如位阻胺,或例如在EP 669 353中描述的其它助剂。
根据本发明使用的反应性聚氨酯组合物在正常条件下,例如用DBTL催化,自160℃起,通常自大约180℃起固化。根据本发明使用的反应性聚氨酯组合物提供极好的流动和因此良好的浸渍能力和在固化状态下优异的化学品耐受性。此外,在使用脂族交联剂(例如IPDI或H12MDI)时,还另外实现良好的耐候性。
在本发明中特别优选使用由下列材料制成的基质材料
B) 至少一种含有脲二酮基团的高反应性聚氨酯组合物,其基本上含有
a) 至少一种含有脲二酮基团的固化剂
和
b) 任选至少一种具有NCO基团反应性官能团的聚合物;
c) 0.1至5重量%的至少一种催化剂,其选自以卤离子、氢氧根、烷氧离子或有机或无机酸阴离子为抗衡离子的季铵盐和/或季鏻盐;
和
d) 0.1至5重量%的至少一种助催化剂,其选自
d1) 至少一种环氧化物
和/或
d2) 至少一种金属乙酰丙酮化物和/或季铵乙酰丙酮化物和/或季鏻乙酰丙酮化物;和
e) 任选地,由聚氨酯化学已知的助剂和添加剂。
非常特别使用由下列材料制成的基质材料B)
B) 至少一种含有脲二酮基团的高反应性粉末状聚氨酯组合物作为基质材料,其基本上含有
a) 至少一种含有脲二酮基团的固化剂,所述固化剂基于脂族、(环)脂族或脂环族的含有脲二酮基团的多异氰酸酯和含羟基的化合物的加聚化合物,其中该固化剂在40℃以下以固体形式存在和在125℃以上以液体形式存在并具有小于5重量%的游离NCO含量和3-25重量%的脲二酮含量,
b) 至少一种含羟基的聚合物,其在40℃以下以固体形式存在和在125℃以上以液体形式存在并具有20至200毫克KOH/克之间的OH值;
c) 0.1至5重量%的至少一种催化剂,其选自以卤离子、氢氧根、烷氧离子或有机或无机酸阴离子为抗衡离子的季铵盐和/或季鏻盐;
和
d) 0.1至5重量%的至少一种助催化剂,其选自
d1) 至少一种环氧化物
和/或
d2) 至少一种金属乙酰丙酮化物和/或季铵乙酰丙酮化物和/或季鏻乙酰丙酮化物;和
e) 任选地,由聚氨酯化学已知的助剂和添加剂,
以使这两种组分a)和b)以下述比率存在,即在组分b)的每个羟基上消耗组分a)的0.3至1个,优选0.6至0.9个脲二酮基团。后者相当于0.6-2:1或1.2-1.8:1的NCO/OH比。根据本发明使用的这些高反应性聚氨酯组合物在100至160℃的温度下固化并被称作方案II。
根据本发明,合适的含有脲二酮基团的高反应性聚氨酯组合物含有下述组分的混合物:暂时失活的、即含有脲二酮基团的(内部封端)二-或多异氰酸酯,也称作固化剂a),和根据本发明包含的催化剂c)和d)以及任选另外具有NCO基团反应性官能团的聚合物(粘合剂),也称作树脂b)。催化剂确保含有脲二酮基团的聚氨酯组合物在低温下固化。该含有脲二酮基团的聚氨酯组合物因此是高反应性的。
作为组分a)和b),使用如上描述的那些。
作为c)下的催化剂,使用以卤离子、氢氧根、烷氧离子或有机或无机酸阴离子为抗衡离子的季铵盐,优选四烷基铵盐和/或季鏻盐。这些的实例是:四甲基甲酸铵、四甲基乙酸铵、四甲基丙酸铵、四甲基丁酸铵、四甲基苯甲酸铵、四乙基甲酸铵、四乙基乙酸铵、四乙基丙酸铵、四乙基丁酸铵、四乙基苯甲酸铵、四丙基甲酸铵、四丙基乙酸铵、四丙基丙酸铵、四丙基丁酸铵、四丙基苯甲酸铵、四丁基甲酸铵、四丁基乙酸铵、四丁基丙酸铵、四丁基丁酸铵和四丁基苯甲酸铵和四丁基乙酸鏻、四丁基甲酸鏻和乙基三苯基乙酸鏻、四丁基鏻苯并三唑盐、四苯基苯酚鏻和三己基十四烷基癸酸鏻、甲基三丁基氢氧化铵、甲基三乙基氢氧化铵、四甲基氢氧化铵、四乙基氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、四戊基氢氧化铵、四己基氢氧化铵、四辛基氢氧化铵、四癸基氢氧化铵、十四烷基三己基氢氧化铵、四-十八烷基氢氧化铵、苄基三甲基氢氧化铵、苄基三乙基氢氧化铵、三甲基苯基氢氧化铵、三乙基甲基氢氧化铵、三甲基乙烯基氢氧化铵、甲基三丁基甲醇铵、甲基三乙基甲醇铵、四甲基甲醇铵、四乙基甲醇铵、四丙基甲醇铵、四丁基甲醇铵、四戊基甲醇铵、四己基甲醇铵、四辛基甲醇铵、四癸基甲醇铵、十四烷基三己基甲醇铵、四-十八烷基甲醇铵、苄基三甲基甲醇铵、苄基三乙基甲醇铵、三甲基苯基甲醇铵、三乙基甲基甲醇铵、三甲基乙烯基甲醇铵、甲基三丁基乙醇铵、甲基三乙基乙醇铵、四甲基乙醇铵、四乙基乙醇铵、四丙基乙醇铵、四丁基乙醇铵、四戊基乙醇铵、四己基乙醇铵、四辛基甲醇铵、四癸基乙醇铵、十四烷基三己基乙醇铵、四-十八烷基乙醇铵、苄基三甲基乙醇铵、苄基三乙基乙醇铵、三甲基苯基乙醇铵、三乙基甲基乙醇铵、三甲基乙烯基乙醇铵、甲基三丁基苄醇铵、甲基三乙基苄醇铵、四甲基苄醇铵、四乙基苄醇铵、四丙基苄醇铵、四丁基苄醇铵、四戊基苄醇铵、四己基苄醇铵、四辛基苄醇铵、四癸基苄醇铵、十四烷基三己基苄醇铵、四-十八烷基苄醇铵、苄基三甲基苄醇铵、苄基三乙基苄醇铵、三甲基苯基苄醇铵、三乙基甲基苄醇铵、三甲基乙烯基苄醇铵、四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、四辛基氟化铵、苄基三甲基氟化铵、四丁基氢氧化鏻、四丁基氟化鏻、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵、四乙基氯化铵、四乙基溴化铵、四乙基碘化铵、四甲基氯化铵、四甲基溴化铵、四甲基碘化铵、苄基三甲基氯化铵、苄基三乙基氯化铵、苄基三丙基氯化铵、苄基三丁基氯化铵、甲基三丁基氯化铵、甲基三丙基氯化铵、甲基三乙基氯化铵、甲基三苯基氯化铵、苯基三甲基氯化铵、苄基三甲基溴化铵、苄基三乙基溴化铵、苄基三丙基溴化铵、苄基三丁基溴化铵、甲基三丁基溴化铵、甲基三丙基溴化铵、甲基三乙基溴化铵、甲基三苯基溴化铵、苯基三甲基溴化铵、苄基三甲基碘化铵、苄基三乙基碘化铵、苄基三丙基碘化铵、苄基三丁基碘化铵、甲基三丁基碘化铵、甲基三丙基碘化铵、甲基三乙基碘化铵、甲基三苯基碘化铵和苯基三甲基碘化铵、甲基三丁基氢氧化铵、甲基三乙基氢氧化铵、四甲基氢氧化铵、四乙基氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、四戊基氢氧化铵、四己基氢氧化铵、四辛基氢氧化铵、四癸基氢氧化铵、十四烷基三己基氢氧化铵、四-十八烷基氢氧化铵、苄基三甲基氢氧化铵、苄基三乙基氢氧化铵、三甲基苯基氢氧化铵、三乙基甲基氢氧化铵、三甲基乙烯基氢氧化铵、四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、四辛基氟化铵和苄基三甲基氟化铵。这些催化剂可以单独地或以混合物添加。优选使用四乙基苯甲酸铵和/或四丁基氢氧化铵。
催化剂c)的含量可以为0.1至5重量%,优选0.3至2重量%,基于该基质材料的总配制品计。
根据本发明的一个方案包括这样的催化剂c)键合到聚合物b)的官能团上。此外,这些催化剂可以被惰性壳包围并由此包囊。
作为助催化剂d1),使用环氧化物。在此合适的是例如缩水甘油醚和缩水甘油酯、脂族环氧化物、基于双酚A的二缩水甘油醚和甲基丙烯酸缩水甘油酯。这样的环氧化物的实例是异氰脲酸三缩水甘油酯(TGIC,商品名Araldit 810, Huntsman)、对苯二甲酸二缩水甘油酯和偏苯三酸三缩水甘油酯的混合物(商品名Araldit PT 910和912, Huntsman)、Versatic 酸的缩水甘油酯(商品名Kardura E10, Shell)、3,4-环氧环己基甲基-3’,4’-环氧环己烷甲酸酯(ECC)、基于双酚A的二缩水甘油醚(商品名EPIKOTE 828, Shell)、乙基己基缩水甘油醚、丁基缩水甘油醚、季戊四醇四缩水甘油醚(商品名Polypox R 16, UPPC AG)和具有游离环氧基的其它Polypox类型。也可以使用混合物。优选使用ARALDIT PT 910和912。
作为助催化剂d2),合适的是金属乙酰丙酮化物。这些的实例是单独或混合的乙酰丙酮化锌、乙酰丙酮化锂和乙酰丙酮化锡。优选使用乙酰丙酮化锌。
作为助催化剂d2),此外合适的是季铵乙酰丙酮化物或季鏻乙酰丙酮化物。
这样的催化剂的实例是四甲基乙酰丙酮化铵、四乙基乙酰丙酮化铵、四丙基乙酰丙酮化铵、四丁基乙酰丙酮化铵、苄基三甲基乙酰丙酮化铵、苄基三乙基乙酰丙酮化铵、四甲基乙酰丙酮化鏻、四乙基乙酰丙酮化鏻、四丙基乙酰丙酮化鏻、四丁基乙酰丙酮化鏻、苄基三甲基乙酰丙酮化鏻和苄基三乙基乙酰丙酮化鏻。特别优选使用四乙基乙酰丙酮化铵和/或四丁基乙酰丙酮化铵。当然也可以使用这些催化剂的混合物。
助催化剂d1)和/或d2)的含量可以为0.1至5重量%,优选0.3至2重量%,基于该基质材料的总配制品计。
借助于根据本发明使用的高反应性和因此低温固化聚氨酯组合物B),在100至160℃固化温度下,不仅可节省能量和固化时间,还可以使用许多温度敏感的载体。
在本发明范围内,高反应性(方案II)是指,根据本发明使用的含有脲二酮基团的聚氨酯组合物在100至160℃的温度下并且根据载体的性质固化。该固化温度优选为120至150℃,特别优选130至140℃。根据本发明使用的聚氨酯组合物的固化时间在5至60分钟内。
根据本发明使用的含有脲二酮基团的高反应性聚氨酯组合物B)提供极好的流动和因此良好的浸渍能力和在固化状态下优异的化学品耐受性。此外,在使用脂族交联剂(例如IPDI或H12MDI)时,还另外实现良好的耐候性。
原则上,所有已知颜料均为合适的颜料。
使用已知种类的天然和合成的无机颜料的颜料。作为天然颜料合适的是土质颜料,例如绿土、黄赭石或棕土,以及矿物颜料,例如氧化铁、孔雀石或辰砂。此外无机合成颜料,例如炭黑、铬颜料、钴颜料、铁颜料、群青蓝或白色颜料,例如二氧化钛也合适。天然有机颜料和合成有机颜料,如偶氮颜料(亮黄、永久红)、多环颜料(酞菁蓝、Heliogen 绿)或二酮吡咯并吡咯颜料同样合适。金属效果颜料或珠光颜料也合适。
这样的颜料的实例是:普鲁士蓝(颜料蓝27 C.I. 77510)、亮黄(颜料黄74 C.I. 11741)、镉黄(颜料黄35 C.I. 77205)、镉红(颜料红108 C.I. 77202)、氧化铬绿(颜料绿17 C.I. 77288)、钴蓝(颜料蓝28 C.I. 77346)、钴蓝浅青绿色(颜料蓝36 C.I. 77343)、淡钴紫(颜料紫49 C.I. 77362)、氧化铁黑(颜料黑11 C.I. 77499)、Irgazin红(颜料红254 C.I. 56110)、锰紫(颜料紫16 C.I. 77742)、酞菁蓝(有机)(颜料蓝15 C.I. 74160)、钛白(颜料白C.I. 77891)、群青蓝(颜料蓝29 C.I. 77007)、群青红A(颜料红259 C.I. 77007)、棕土(颜料棕7 C.I. 77491)。
合适的染料是所有已知染料,尤其是反应性染料、分散染料、颜料染料、酸染料、显色染料、阳离子或碱性染料、偶合染料、媒染染料、瓮染染料、金属络合染料、直接染料。
重要的且在本发明范围内可使用的染料物质类别是蒽醌染料、偶氮染料、二噁嗪染料、靛蓝染料、硝基染料、亚硝基染料、酞菁染料、硫化染料、三苯甲烷染料。
例如在来自Clariant “Colorants for Powder Coatings” (2005)和来自BASF “Colorants and additives from BASF for powder coatings” (2008)的文献中详述了专门适合粉末涂料用途的染料和颜料。
总之,优选的是颜料配制品,因为染料具有至少有限的光稳定性或耐候稳定性,这限制了由相应着色的本发明的预浸料制成的复合部件的直接户外使用。
所述染料以15至重量%的量包含于基质材料B)中。
颜料以0.5至20重量%的量包含于基质材料B)中。
所述基质材料的制造可以如下进行:用于制造聚氨酯组合物B)的所有组分的均化可以在合适的装置,例如可加热的搅拌釜、捏合机或甚至挤出机中进行,在此过程中不应超过120至130℃的温度上限。各组分的混合优选在挤出机中在下述温度下进行:该温度尽管位于各组分的熔融范围以上,但位于开始交联反应的温度以下。此后可以直接由熔体使用或在冷却和制造粉末后使用。也可以在溶剂中通过在前述装置中混合来进行聚氨酯组合物B)的制造。
接着,根据方法,将基质材料B)与载体A)一起加工成预浸料。
根据本发明的预浸料以及复合部件具有大于50%,优选大于50-70%,特别优选50至65%的纤维体积含量。
根据本发明用作基质材料的反应性或高反应性聚氨酯组合物基本上由反应性树脂和固化剂的混合物构成。在熔体均化后,这种混合物具有至少40℃的Tg并通常在反应性聚氨酯组合物的情况下仅在160℃以上或在高反应性聚氨酯组合物的情况下在100℃以上反应,生成交联的聚氨酯并由此形成该复合材料的基质。这意味着根据本发明的预浸料在其制成后由载体和施加的作为基质材料的反应性聚氨酯组合物(其以非交联但反应性形式存在)构成。
该预浸料因此储存稳定通常数天和甚至数周,并因此可随时进一步加工成复合材料。这是与上文已描述的反应性且不耐储存的双组分体系的本质区别,因为在涂施后后者立即开始反应和交联产生聚氨酯。
根据本发明的预浸料的制造可以借助已知装置和设备通过反应注射成型(RIM)、增强反应注射成型(RRIM)、拉挤成型法、通过在轧机机架中或借助热刮刀施加溶液或其它方法进行。
本发明的主题还有特别是具有玻璃-、碳-或芳族聚酰胺-纤维的纤维状载体的预浸料的用途。
本发明的主题还有根据本发明的预浸料用于制造船舶建造中、航空航天技术中、汽车制造中和两轮车优选摩托车和自行车中以及在汽车、建筑、医学工程、运动、电-和电子工业、发电装置(例如用于风力发电装置中的转子叶片)领域中的复合材料的用途。
本发明的主题还有由根据本发明制成的预浸料制成的复合部件。
实施例
反应性聚氨酯组合物
具有下列配方的反应性聚氨酯组合物用于制造预浸料和复合材料。
将经粉碎的该表的原料在预混器中密切混合,然后在挤出机中在最高130℃下均化。这种反应性聚氨酯组合物随后在研磨后按照粉末浸渍法用于制造预浸料。对于直接熔体浸渍法,可直接使用在挤出机中制成的均化的熔体混合物。对于基于溶剂的方法,不需要上游的熔体均化。
DSC测量
用Mettler Toledo DSC 821e根据DIN 53765进行DSC研究(玻璃化转变温度测定和反应焓测量)。
测得挤出物的玻璃化转变温度为62℃;在新鲜状态下,交联反应的反应焓为65.5 J/g。
在该预浸料的基质交联后,玻璃化转变温度升至80℃并且不再可检出用于交联的热流。结果参见图1。
所用玻璃纤维网格布和玻璃纤维织物:
在实施例中使用下列玻璃纤维网格布和玻璃纤维织物,并在下文中被称作类型I和类型II。
类型I是来自“Schl?sser & Cramer”的亚麻布-E-玻璃布281 L 型号 3103。该织物具有280克/平方米的面积重量。
类型II GBX 600 型号1023是来自“Schl?sser & Cramer”的缝合双轴E-玻璃网格布(-45/+45)。这应被理解为是指相互叠加并彼此呈90度角的两层纤维束。这种结构通过其它纤维(但其不由玻璃构成)固定在一起。玻璃纤维的表面配备有氨基硅烷改性的标准胶料。该网格布具有600克/平方米的面积重量。
预浸料的制造
根据DE 102010029355借助于直接熔体浸渍法制造预浸料。
预浸料的储存稳定性
借助DSC研究用玻璃化转变温度和交联反应的反应焓测定预浸料的储存稳定性。
通过在室温下储存5周不损害该PU-预浸料的交联能力。
复合部件制造
在复合压机上通过本领域技术人员已知的压制技术制造复合部件。将借助于直接熔体浸渍法制成的均匀预浸料在台式压机上压制成复合材料。这种台式压机是来自Schwabenthan公司的Polystat 200 T,在120至200℃之间的温度下用其将预浸料压制成相应的复合片材。压力在常压至450巴之间变化。根据部件尺寸、-厚度和聚氨酯组合物和因此在加工温度下的粘度调节,动态压制,即交替施压,经证实可有利于纤维的润湿。
在一个实例中,压机温度在熔融阶段中从90℃提高至110℃,在3分钟熔融阶段后压力提高至440巴,然后在150和440巴之间动态改变(7次,各持续1分钟),在此期间温度连续提高至140℃。接着将温度升至180℃并同时使压力保持在350巴直至在30分钟后从压机中取出复合部件。测试具有纤维体积含量> 50%的硬的刚性、耐化学品和抗冲击的复合部件(片材产品)的固化度(通过DSC测定)。经固化的基质的玻璃化转变温度的测定指示在不同固化温度下的交联进程。在所使用的聚氨酯组合物中,在大约25分钟后完全交联,然后也不再可检出交联反应的反应焓。
Claims (16)
2.根据权利要求1的预浸料,
其中所述基质材料B)具有至少40℃的Tg。
3.根据前述权利要求至少一项的预浸料,
其特征在于,
所述预浸料具有大于50%,优选大于50至70%,特别优选50至65%的纤维体积含量。
4.根据前述权利要求至少一项的预浸料,
其特征在于,
包含天然的和/或合成的无机颜料作为颜料。
5.根据前述权利要求至少一项的预浸料,
其特征在于,
包含选自下述的染料:活性染料、分散染料、颜料染料、酸染料、显色染料、阳离子或碱性染料、偶合染料、媒染染料、瓮染染料、金属络合染料、直接染料。
6.根据前述权利要求至少一项的预浸料,
其特征在于,
使用具有羟基、氨基和硫醇基的聚合物b),特别是具有OH值为20至500毫克KOH/克且平均摩尔质量为250至6000克/摩尔的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯。
7.根据前述权利要求至少一项的预浸料,
其特征在于,
使用选自下述的二-或多异氰酸酯作为组分a)的原料化合物:异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、二异氰酸根合二环己基甲烷(H12MDI)、2-甲基戊烷二异氰酸酯(MPDI)、2,2,4-三甲基六亚甲基二异氰酸酯/2,4,4-三甲基六亚甲基二异氰酸酯(TMDI)和/或降冰片烷二异氰酸酯(NBDI),特别优选IPDI、HDI、TMDI和/或H12MDI,其中也可使用异氰脲酸酯。
8.根据前述权利要求至少一项的预浸料,
其特征在于,
使用选自下述的外部封端剂用于a)的封端:乙酰乙酸乙酯、二异丙胺、甲基乙基酮肟、丙二酸二乙酯、ε-己内酰胺、1,2,4-三唑、苯酚或取代酚和/或3,5-二甲基吡唑。
9.根据前述权利要求至少一项的预浸料,
其特征在于,
使用异氰脲酸酯基团和ε-己内酰胺封端的异氰酸酯结构的IPDI加合物作为组分a)。
10.根据前述权利要求至少一项的预浸料,
其特征在于,
所述反应性聚氨酯组合物B)含有0.001 - 1重量%的量的另外的催化剂,优选为二月桂酸二丁基锡、辛酸锌、新癸酸铋,和/或叔胺,优选1,4-二氮杂双环[2.2.2]辛烷。
11.根据前述权利要求至少一项的预浸料,
其具有得自至少一种含有脲二酮基团的反应性聚氨酯组合物B)的基质材料,其基本上含有
a) 至少一种含有脲二酮基团的固化剂,所述固化剂基于脂族、(环)脂族或脂环族的含有脲二酮基团的多异氰酸酯和含羟基的化合物的加聚化合物,其中所述固化剂在40℃以下以固体形式存在和在125℃以上以液体形式存在,具有小于5重量%的游离NCO含量和3-25重量%的脲二酮含量,
b) 至少一种含羟基的聚合物,其在40℃以下以固体形式存在和在125℃以上以液体形式存在并具有20至200毫克KOH/克的OH值,
c) 任选至少一种催化剂,
d) 任选地,由聚氨酯化学已知的助剂和添加剂,
以使这两种组分a)和b)以这样的比例存在,即在组分b)的每个羟基上消耗组分a)的0.3至1个,优选0.45至0.55个脲二酮基团。
12.根据权利要求1至9至少一项的预浸料,其具有至少一种含有脲二酮基团的高反应性粉末状聚氨酯组合物B)作为基质材料,其基本上含有
a) 至少一种含有脲二酮基团的固化剂
和
b) 任选至少一种具有NCO基团反应性官能团的聚合物;
c) 0.1至5重量%的至少一种催化剂,其选自以卤离子、氢氧根、烷氧离子或有机或无机酸阴离子作为抗衡离子的季铵盐和/或季鏻盐;
和
d) 0.1至5重量%的至少一种助催化剂,其选自
d1) 至少一种环氧化物
和/或
d2) 至少一种金属乙酰丙酮化物和/或季铵乙酰丙酮化物和/或季鏻乙酰丙酮化物;
e) 任选地,由聚氨酯化学已知的助剂和添加剂。
13.根据前述权利要求1至9或12至少一项的预浸料,其具有至少一种含有脲二酮基团的高反应性粉末状聚氨酯组合物B)作为基质材料,其基本上含有
a) 至少一种含有脲二酮基团的固化剂,所述固化剂基于脂族、(环)脂族或脂环族的含有脲二酮基团的多异氰酸酯和含羟基的化合物的加聚化合物,其中所述固化剂在40℃以下以固体形式存在和在125℃以上以液体形式存在并具有小于5重量%的游离NCO含量和3-25重量%的脲二酮含量,
b) 至少一种含羟基的聚合物,其在40℃以下以固体形式存在和在125℃以上以液体形式存在并具有20至200毫克KOH/克的OH值;
c) 0.1至5重量%的至少一种催化剂,其选自以卤离子、氢氧根、烷氧离子或有机或无机酸阴离子作为抗衡离子的季铵盐和/或季鏻盐;
和
d) 0.1至5重量%的至少一种助催化剂,其选自
d1) 至少一种环氧化物
和/或
d2) 至少一种金属乙酰丙酮化物和/或季铵乙酰丙酮化物和/或季鏻乙酰丙酮化物;
e) 任选地,由聚氨酯化学已知的助剂和添加剂,
以使这两种组分a)和b)以这样的比例存在,即在组分b)的每个羟基上消耗组分a)的0.3至1个,优选0.6至0.9个脲二酮基团。
14.根据前述权利要求1至13至少一项的预浸料的用途,所述预浸料尤其具有玻璃-、碳-或芳族聚酰胺-纤维的纤维状载体。
15.根据权利要求1至13至少一项的预浸料用于制造船舶建造中、航空航天技术中、汽车制造中,用于两轮车,优选摩托车和自行车,在汽车、建筑、医学技术、运动、电-和电子工业、发电厂,例如风力发电厂中的转子叶片领域中的复合材料的用途。
16.由根据权利要求1至13至少一项的预浸料制成的复合部件。
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KR102502684B1 (ko) | 2022-09-20 | 2023-02-23 | 주식회사 새솔 | 악취 발생을 저감한 유기성 오니 처리방법 |
KR102596533B1 (ko) | 2023-06-16 | 2023-11-01 | 주식회사 태건리너텍 | 하수 오니를 처리한 부숙 연료 및 그 처리 방법과 시스템 |
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- 2011-08-30 US US13/824,084 patent/US20130231022A1/en not_active Abandoned
- 2011-08-30 EP EP11757213.1A patent/EP2619256A1/de not_active Withdrawn
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- 2011-08-30 WO PCT/EP2011/064895 patent/WO2012038200A1/de active Application Filing
- 2011-08-30 AU AU2011304536A patent/AU2011304536B2/en not_active Ceased
- 2011-08-30 JP JP2013529594A patent/JP2013537928A/ja not_active Withdrawn
- 2011-08-30 BR BR112013006846A patent/BR112013006846A2/pt not_active IP Right Cessation
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CA2811063A1 (en) | 2012-03-29 |
DE102010041239A1 (de) | 2012-03-29 |
MX2013003169A (es) | 2013-05-06 |
KR20130109142A (ko) | 2013-10-07 |
RU2013118433A (ru) | 2014-10-27 |
ZA201302838B (en) | 2013-12-23 |
EP2619256A1 (de) | 2013-07-31 |
AU2011304536A1 (en) | 2013-04-04 |
US20130231022A1 (en) | 2013-09-05 |
TW201226453A (en) | 2012-07-01 |
BR112013006846A2 (pt) | 2016-06-07 |
WO2012038200A1 (de) | 2012-03-29 |
AU2011304536B2 (en) | 2014-03-13 |
JP2013537928A (ja) | 2013-10-07 |
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