ES2341762T3 - Composiciones reactivas de poliuretano con bajo contenido en monomeros residuales. - Google Patents
Composiciones reactivas de poliuretano con bajo contenido en monomeros residuales. Download PDFInfo
- Publication number
- ES2341762T3 ES2341762T3 ES02782814T ES02782814T ES2341762T3 ES 2341762 T3 ES2341762 T3 ES 2341762T3 ES 02782814 T ES02782814 T ES 02782814T ES 02782814 T ES02782814 T ES 02782814T ES 2341762 T3 ES2341762 T3 ES 2341762T3
- Authority
- ES
- Spain
- Prior art keywords
- isocyanate
- isocyanophenyl
- weight
- methyl
- less
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 239000000178 monomer Substances 0.000 title description 27
- 239000004814 polyurethane Substances 0.000 title description 24
- 229920002635 polyurethane Polymers 0.000 title description 24
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 42
- 229920005862 polyol Polymers 0.000 claims abstract description 36
- 239000000853 adhesive Substances 0.000 claims abstract description 24
- 230000001070 adhesive effect Effects 0.000 claims abstract description 24
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 6
- -1 (3-isocyanophenyl) -methyl Chemical group 0.000 claims description 40
- 150000003077 polyols Chemical class 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 26
- 239000012943 hotmelt Substances 0.000 claims description 24
- 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 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 20
- 239000003292 glue Substances 0.000 claims description 18
- 150000002513 isocyanates Chemical class 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 13
- 239000005056 polyisocyanate Substances 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003623 enhancer Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 6
- 150000004072 triols Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 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 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- XGGGASQCZWCTEN-UHFFFAOYSA-N [C-]#[N+]C1=C(CC2=C(CC(C=CC=C3)=C3[N+]#[C-])C=CC=C2)C=CC=C1.N=C=O Chemical compound [C-]#[N+]C1=C(CC2=C(CC(C=CC=C3)=C3[N+]#[C-])C=CC=C2)C=CC=C1.N=C=O XGGGASQCZWCTEN-UHFFFAOYSA-N 0.000 claims description 3
- DMCDXKSLKCJIOD-UHFFFAOYSA-N [C-]#[N+]C1=CC=C(CC2=C(CC(C=C3)=CC=C3[N+]#[C-])C=CC=C2)C=C1.N=C=O Chemical compound [C-]#[N+]C1=CC=C(CC2=C(CC(C=C3)=CC=C3[N+]#[C-])C=CC=C2)C=C1.N=C=O DMCDXKSLKCJIOD-UHFFFAOYSA-N 0.000 claims description 3
- WXSCXQUYUCJDIF-UHFFFAOYSA-N [N+](#[C-])C1=CC=C(C=C1)C1=C(C=CC=C1C)C Chemical group [N+](#[C-])C1=CC=C(C=C1)C1=C(C=CC=C1C)C WXSCXQUYUCJDIF-UHFFFAOYSA-N 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 238000005829 trimerization reaction Methods 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 239000004831 Hot glue Substances 0.000 abstract description 5
- 229920001515 polyalkylene glycol Polymers 0.000 abstract description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 17
- 239000002253 acid Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
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- BDLNYQVUTQYAGX-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propane-1-thiol Chemical compound CCOC(OCC)[SiH2]CCCS BDLNYQVUTQYAGX-UHFFFAOYSA-N 0.000 description 1
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- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10150722 | 2001-10-13 | ||
| DE10150722A DE10150722A1 (de) | 2001-10-13 | 2001-10-13 | Reaktive Polyurethan-Zusammensetzungen mit niedrigem Restmonomergehalt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2341762T3 true ES2341762T3 (es) | 2010-06-28 |
Family
ID=7702492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02782814T Expired - Lifetime ES2341762T3 (es) | 2001-10-13 | 2002-10-02 | Composiciones reactivas de poliuretano con bajo contenido en monomeros residuales. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9637667B2 (enExample) |
| EP (1) | EP1434811B1 (enExample) |
| JP (1) | JP2005505664A (enExample) |
| KR (1) | KR100989308B1 (enExample) |
| CN (1) | CN100545190C (enExample) |
| AT (1) | ATE461949T1 (enExample) |
| AU (1) | AU2002347044B2 (enExample) |
| BR (1) | BR0213238B1 (enExample) |
| CA (1) | CA2463586C (enExample) |
| DE (2) | DE10150722A1 (enExample) |
| ES (1) | ES2341762T3 (enExample) |
| PL (1) | PL367889A1 (enExample) |
| WO (1) | WO2003033562A1 (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10229519A1 (de) * | 2001-07-10 | 2003-01-30 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
| DE10163857A1 (de) | 2001-12-22 | 2003-07-10 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
| DE50309990D1 (de) | 2002-02-22 | 2008-07-31 | Jowat Ag | Polyurethan-Zusammensetzungen mit geringem Anteil an Diisocyanatmonomer(en) |
| DE10343750A1 (de) * | 2003-09-22 | 2005-04-28 | Henkel Kgaa | Polyurethan-Schmelzklebstoffe mit langer Reaktivierbarkeit |
| DE602004008507T2 (de) * | 2003-11-11 | 2007-12-27 | Ube Industries, Ltd., Ube | Kristallines polyesterpolyol und schmelzklebstoff |
| DE10361277A1 (de) | 2003-12-24 | 2005-07-28 | Henkel Kgaa | Hoch elastische Polyurethan Schmelzklebstoffe |
| DE102004018048A1 (de) * | 2004-04-08 | 2005-11-10 | Henkel Kgaa | Verfahren zur Herstellung von Polyurethan-Prepolymeren |
| DE102004035764A1 (de) * | 2004-07-23 | 2006-03-16 | Bayer Materialscience Ag | Niedrigviskose Polyurethan-Prepolymere auf Basis von 2,4'-MDI |
| JP4539298B2 (ja) * | 2004-11-08 | 2010-09-08 | 横浜ゴム株式会社 | 一液湿気硬化型ウレタン組成物 |
| DE102004057292A1 (de) * | 2004-11-26 | 2006-06-01 | Klebchemie, M.G. Becker Gmbh & Co Kg | Verfahren zur Herstellung von reaktiven Polyurethanzusammensetzungen |
| DE102005012794A1 (de) * | 2005-03-19 | 2006-09-21 | Bayer Materialscience Ag | Poly(etherester)polyole und Verfahren zu ihrer Herstellung |
| DE102005030500A1 (de) * | 2005-06-28 | 2007-01-04 | Basf Ag | Beschichtungsmassen enthaltend 2,4'-Diisocyanatodiphenylmethan |
| DE102005035000A1 (de) | 2005-07-22 | 2007-01-25 | Basf Ag | Isocyanatgruppen enthaltende Prepolymere |
| US20070037955A1 (en) * | 2005-08-15 | 2007-02-15 | Richards James L | Polymeric diluents for structural adhesives |
| EP1770107A1 (de) | 2005-09-30 | 2007-04-04 | Sika Technology AG | Feuchtigkeitshärtende Polyurethanzusammensetzung |
| EP1801138A1 (de) * | 2005-12-23 | 2007-06-27 | Sika Technology AG | Feuchtigkeitshärtende Heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles Polyurethanprepolymer |
| US7732554B2 (en) * | 2006-09-21 | 2010-06-08 | Momentive Performance Materials Inc. | Process for preparing a curable silylated polyurethane resin |
| JP2008133343A (ja) * | 2006-11-28 | 2008-06-12 | Nippon Polyurethane Ind Co Ltd | 主成分として２，４’−ｍｄｉを用いて得られるウレタンプレポリマーからなるウレタンエラストマー形成性組成物 |
| EP2098578B1 (en) * | 2007-07-19 | 2016-03-23 | DIC Corporation | Moisture-curable polyurethane hot-melt adhesive, laminates made with the same, and moisture-permeable film |
| DE102007052207A1 (de) | 2007-10-30 | 2009-05-14 | Henkel Ag & Co. Kgaa | Modifizierte Polyurethanklebstoffe |
| WO2009118112A2 (de) | 2008-03-28 | 2009-10-01 | Bayer Materialscience Ag | 2,2'-mdi-basierte isocyanat-mischungen und ihre herstellung sowie verwendung |
| DE102008025793A1 (de) | 2008-05-29 | 2009-12-03 | Henkel Ag & Co. Kgaa | Reaktive Klebstoffe mit sehr geringem Gehalt an monomeren Diisocyanaten |
| US8901187B1 (en) | 2008-12-19 | 2014-12-02 | Hickory Springs Manufacturing Company | High resilience flexible polyurethane foam using MDI |
| US20100160470A1 (en) * | 2008-12-23 | 2010-06-24 | Smiecinski Theodore M | Flexible Polyurethane Foam |
| US8906975B1 (en) | 2009-02-09 | 2014-12-09 | Hickory Springs Manufacturing Company | Conventional flexible polyurethane foam using MDI |
| JP5283551B2 (ja) * | 2009-03-31 | 2013-09-04 | アイカ工業株式会社 | 湿気硬化型反応性ホットメルト接着剤 |
| US20120083566A1 (en) * | 2009-06-18 | 2012-04-05 | Jason Lazarus Deiner | Ink compositions |
| DE102009046050A1 (de) | 2009-10-27 | 2011-04-28 | Henkel Ag & Co. Kgaa | PU-Klebstoff mit Viskositätsregler |
| DE102010028269A1 (de) | 2010-04-27 | 2011-10-27 | Henkel Ag & Co. Kgaa | PU-Klebstoff mit Fließgrenze |
| JP6161866B2 (ja) | 2010-12-21 | 2017-07-12 | ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ | 接着剤組成物 |
| DE102011089783A1 (de) | 2011-12-23 | 2013-06-27 | Bayer Materialscience Aktiengesellschaft | Niedrigviskose reaktive Polyurethan-Zusammensetzungen |
| DE102012200018A1 (de) * | 2012-01-02 | 2013-07-04 | Bayer Materialscience Ag | Reaktive Polyurethan-Zubereitungen |
| US8877868B2 (en) | 2013-02-26 | 2014-11-04 | Henkel IP & Holding GmbH | Hot melt adhesive comprising cyanoacrylate curing compounds |
| EP3116930B1 (de) | 2014-03-11 | 2018-05-16 | Sika Technology AG | Polyurethan-heissschmelzklebstoff mit niedrigem gehalt an monomeren diisocyanaten und guter vernetzungsgeschwindigkeit |
| FR3021659B1 (fr) * | 2014-05-28 | 2017-11-17 | Bostik Sa | Composition de polyurethane a terminaisons nco a base de 2,4-tdi non thermofusible et a faible teneur en monomere tdi, comprenant au moins un compose isocyanate de volume molaire particulier. |
| EP3088435A1 (de) | 2015-04-28 | 2016-11-02 | Sika Technology AG | Zweistufiges verfahren zur herstellung eines polyurethan-heissschmelzklebstoffs mit niedrigem gehalt an monomeren diisocyanaten und hoher anfangsfestigkeit |
| MX2018011343A (es) | 2016-03-23 | 2019-01-31 | Fuller H B Co | Composicion de adhesivo termofusible reactivo. |
| ES2870667T3 (es) | 2016-11-01 | 2021-10-27 | Sika Tech Ag | Adhesivo termofusible curable por humedad con bajo contenido de monómeros de diisocianato, menor adhesividad en reposo y alta estabilidad térmica |
| ES2904679T3 (es) | 2016-11-01 | 2022-04-05 | Sika Tech Ag | Método para reducir la adherencia en reposo de adhesivos de poliuretano de fusión en caliente de curado por humedad |
| EP3450476A1 (de) * | 2017-08-31 | 2019-03-06 | Evonik Degussa GmbH | Reaktivklebstoffe mit niedrigem gehalt an monomerem diisocyanat |
| CN107523255A (zh) * | 2017-09-08 | 2017-12-29 | 广州市极威新材料有限公司 | 一种用于贴面装饰的湿固化聚氨酯热熔胶 |
| JP6344877B1 (ja) * | 2017-10-26 | 2018-06-20 | 太陽精機株式会社 | 湿気硬化性ポリウレタンホットメルト接着剤及びその製造方法 |
| WO2019162206A2 (de) * | 2018-02-21 | 2019-08-29 | Basf Se | Verfahren zur herstellung von mit klebstoff beschichteten artikeln |
| EP3569625A1 (en) * | 2018-05-18 | 2019-11-20 | Henkel AG & Co. KGaA | Polyurethane hotmelt adhesive which do not cause polarizer discoloration at hthh conditon |
| WO2020264159A1 (en) * | 2019-06-25 | 2020-12-30 | H.B. Fuller Company | Moisture curable polyurethane hot melt adhesive composition having low levels of diisocyanate monomer |
| CN110564354A (zh) * | 2019-07-25 | 2019-12-13 | 启东东岳化工有限公司 | 一种辊涂用高初粘力的聚氨酯粘合剂及其制备方法 |
| DE102020111278A1 (de) | 2020-04-24 | 2021-10-28 | Klebchemie M.G. Becker Gmbh & Co. Kg | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
| JP7380842B2 (ja) * | 2021-02-02 | 2023-11-15 | Dic株式会社 | 接着剤、積層体、包装材 |
| CN112980378B (zh) * | 2021-02-26 | 2022-02-18 | 中国科学院长春应用化学研究所 | 一种囊体材料用四组分聚氨酯胶粘剂及其制备方法以及应用 |
| DE102021127517A1 (de) | 2021-10-22 | 2023-04-27 | Klebchemie M.G. Becker GmbH & Co KG | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
| CN115246918B (zh) * | 2021-10-26 | 2024-04-26 | 佳化化学科技发展（上海）有限公司 | 一种硅烷改性聚氨酯树脂及其制备方法和用途 |
| KR102865449B1 (ko) * | 2021-11-30 | 2025-09-25 | 한화솔루션 주식회사 | 이소시아네이트 조성물 및 이의 제조방법 |
| WO2024199453A1 (en) * | 2023-03-31 | 2024-10-03 | Shanghai Zhiguan Polymer Materials Co., Ltd. | Reactive polyurethane hot-melt adhesive composition and article |
| WO2024248591A1 (ko) * | 2023-05-30 | 2024-12-05 | 한화솔루션 주식회사 | 이소시아네이트 조성물의 제조 방법 |
| DE102024114875A1 (de) | 2024-05-28 | 2025-12-04 | Kleiberit Se & Co. Kg | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
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| DE3739261A1 (de) | 1987-11-18 | 1989-06-01 | Bayer Ag | Verfahren zur herstellung von urethangruppen aufweisenden polyisocyanaten und ihre verwendung |
| GB8908495D0 (en) | 1989-04-14 | 1989-06-01 | Ici Plc | Polyisocyanate compositions |
| EP0448825A3 (en) * | 1990-03-23 | 1992-04-29 | Bayer Ag | Melt adhesive process |
| CA2077336C (en) | 1990-03-30 | 1997-08-19 | Gregory J. Anderson | Hot melt moisture-cure polyurethane adhesive |
| CA2039964A1 (en) * | 1990-04-27 | 1991-10-28 | Charles W. Stobbie, Iv | Mixture of isocyanate-terminated polyurethane prepolymers |
| DE4136490C2 (de) * | 1991-11-06 | 2003-04-30 | Bayer Ag | Lösungsmittelfreie Beschichtungssysteme |
| US5932680A (en) * | 1993-11-16 | 1999-08-03 | Henkel Kommanditgesellschaft Auf Aktien | Moisture-curing polyurethane hot-melt adhesive |
| DE4419449A1 (de) * | 1994-06-03 | 1995-12-07 | Henkel Kgaa | Schnell abbindender Polyurethan-Schmelzklebstoff |
| PT797604E (pt) | 1994-05-25 | 2000-05-31 | Henkel Kgaa | Cola de fusao de poliuretano que endurece por accao da humidade |
| DE4426130A1 (de) | 1994-07-22 | 1996-01-25 | Bayer Ag | Isocyanatgruppen enthaltende reaktive Hotmeltsysteme |
| ES2125651T5 (es) | 1994-08-22 | 2004-11-01 | Henkel Kommanditgesellschaft Auf Aktien | Composiciones de poliuretano con bajo contenido en diisocianatos monomeros. |
| DE19700014A1 (de) | 1997-01-02 | 1998-07-09 | Henkel Kgaa | Monomerenarmes PU-Prepolymer |
| US6784242B2 (en) | 1997-11-11 | 2004-08-31 | Henkel Kommanditgesellschaft Auf Aktien | Polyurethane binding agents having a low content of highly volatile monomers |
| DE19851182A1 (de) | 1997-11-11 | 1999-05-12 | Henkel Kgaa | Polyurethanbindemittel mit einem niedrigen Gehalt an leichtflüchtigen Monomeren |
| WO1999028363A1 (en) | 1997-12-01 | 1999-06-10 | Henkel Kommanditgesellschaft Auf Aktien | Modified polyurethane hotmelt adhesive |
| US6809171B2 (en) | 1998-07-20 | 2004-10-26 | Henkel Kommanditgesellschaft Auf Aktien | Monomer-poor polyurethane bonding agent having an improved lubricant adhesion |
| JP2000211295A (ja) | 1999-01-26 | 2000-08-02 | Sekisui Chem Co Ltd | 化粧シ―ト被覆材の製造方法 |
| JP2000297130A (ja) | 1999-04-15 | 2000-10-24 | Mitsubishi Gas Chem Co Inc | ポリイソシアネートプレポリマー |
| DK1189961T3 (da) | 1999-07-02 | 2004-06-21 | Henkel Kgaa | Kontaktklæbende polyurethansammensætning med et lavt monomerindhold |
| CZ20021146A3 (cs) * | 1999-11-29 | 2002-06-12 | Henkel Kommanditgesellschaft Auf Aktien | Aktivátor přilnavosti pro reaktivní polyuretanový prostředek |
| DE60032938T2 (de) | 1999-11-30 | 2007-07-05 | Chemtura Corporation, Middlebury | Verfahren zur herstellung von mdi-präpolymeren mit reduziertem gehalt an freiem mdi-monomer |
| DE10013186A1 (de) | 2000-03-17 | 2001-09-20 | Basf Ag | Polyisocyanate |
| DE10028810A1 (de) * | 2000-06-10 | 2001-12-20 | Henkel Kgaa | Polyurethan-Zusammensetzungen auf der Basis von Polyester-Block-Copolymeren |
| AU2002221673A1 (en) | 2000-10-23 | 2002-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Reactive adhesive with a low monomer content and with multistage hardening |
| DE10157488A1 (de) | 2000-12-15 | 2002-06-20 | Henkel Kgaa | Polyurethan-Prepolymere mit NCO-Gruppen und niedrigem Gehalt an monomeren Polyisocyanat |
| DE10229519A1 (de) | 2001-07-10 | 2003-01-30 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
-
2001
- 2001-10-13 DE DE10150722A patent/DE10150722A1/de not_active Ceased
-
2002
- 2002-10-02 DE DE50214303T patent/DE50214303D1/de not_active Expired - Lifetime
- 2002-10-02 BR BRPI0213238-9A patent/BR0213238B1/pt not_active IP Right Cessation
- 2002-10-02 AU AU2002347044A patent/AU2002347044B2/en not_active Ceased
- 2002-10-02 JP JP2003536298A patent/JP2005505664A/ja active Pending
- 2002-10-02 WO PCT/EP2002/011044 patent/WO2003033562A1/de not_active Ceased
- 2002-10-02 CN CNB02820154XA patent/CN100545190C/zh not_active Expired - Fee Related
- 2002-10-02 PL PL02367889A patent/PL367889A1/xx not_active Application Discontinuation
- 2002-10-02 KR KR1020047005361A patent/KR100989308B1/ko not_active Expired - Fee Related
- 2002-10-02 ES ES02782814T patent/ES2341762T3/es not_active Expired - Lifetime
- 2002-10-02 AT AT02782814T patent/ATE461949T1/de active
- 2002-10-02 CA CA2463586A patent/CA2463586C/en not_active Expired - Fee Related
- 2002-10-02 EP EP02782814A patent/EP1434811B1/de not_active Revoked
-
2004
- 2004-04-12 US US10/822,625 patent/US9637667B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20050032973A1 (en) | 2005-02-10 |
| US9637667B2 (en) | 2017-05-02 |
| PL367889A1 (en) | 2005-03-07 |
| CN100545190C (zh) | 2009-09-30 |
| CA2463586A1 (en) | 2003-04-24 |
| EP1434811A1 (de) | 2004-07-07 |
| AU2002347044B2 (en) | 2006-12-21 |
| DE10150722A1 (de) | 2003-04-30 |
| DE50214303D1 (de) | 2010-05-06 |
| KR100989308B1 (ko) | 2010-10-25 |
| JP2005505664A (ja) | 2005-02-24 |
| BR0213238A (pt) | 2004-09-28 |
| BR0213238B1 (pt) | 2012-11-27 |
| CN1568337A (zh) | 2005-01-19 |
| EP1434811B1 (de) | 2010-03-24 |
| WO2003033562A1 (de) | 2003-04-24 |
| CA2463586C (en) | 2011-06-21 |
| ATE461949T1 (de) | 2010-04-15 |
| KR20050033045A (ko) | 2005-04-08 |
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