PH26588A - Laminated safety pane - Google Patents
Laminated safety pane Download PDFInfo
- Publication number
- PH26588A PH26588A PH30957A PH30957A PH26588A PH 26588 A PH26588 A PH 26588A PH 30957 A PH30957 A PH 30957A PH 30957 A PH30957 A PH 30957A PH 26588 A PH26588 A PH 26588A
- Authority
- PH
- Philippines
- Prior art keywords
- component
- layer
- isocyanate
- polyol
- plastics material
- Prior art date
Links
- 229920005862 polyol Polymers 0.000 claims abstract description 39
- 150000003077 polyols Chemical class 0.000 claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 26
- 239000012948 isocyanate Substances 0.000 claims abstract description 25
- 229920003023 plastic Polymers 0.000 claims abstract description 24
- 239000011521 glass Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 19
- 150000002009 diols Chemical class 0.000 claims abstract description 18
- 239000004033 plastic Substances 0.000 claims abstract description 18
- 238000005266 casting Methods 0.000 claims abstract description 15
- 238000005299 abrasion Methods 0.000 claims abstract description 14
- 239000004814 polyurethane Substances 0.000 claims abstract description 13
- 229920002635 polyurethane Polymers 0.000 claims abstract description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 238000010521 absorption reaction Methods 0.000 claims abstract description 6
- 239000004202 carbamide Substances 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 3
- 238000006748 scratching Methods 0.000 claims description 12
- 230000002393 scratching effect Effects 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000003892 spreading Methods 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 241000206607 Porphyra umbilicalis Species 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 44
- -1 aliphatic isocyanates Chemical class 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 229920001169 thermoplastic Polymers 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 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 4
- 238000000034 method Methods 0.000 description 4
- 230000035939 shock Effects 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 208000034693 Laceration Diseases 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- LYDHLGJJJAWBDY-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatocyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(N=C=O)CCC1C(C)(C)C1CCC(N=C=O)CC1 LYDHLGJJJAWBDY-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- CTNICFBTUIFPOE-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)ethane-1,1-diol Chemical compound OC(O)COC1=CC=C(O)C=C1 CTNICFBTUIFPOE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- 241000985627 Lota Species 0.000 description 1
- 101100490488 Mus musculus Add3 gene Proteins 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- CKFGINPQOCXMAZ-UHFFFAOYSA-N formaldehyde hydrate Natural products OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
- C03C27/06—Joining glass to glass by processes other than fusing
- C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10807—Making laminated safety glass or glazing; Apparatus therefor
- B32B17/10899—Making laminated safety glass or glazing; Apparatus therefor by introducing interlayers of synthetic resin
- B32B17/10908—Making laminated safety glass or glazing; Apparatus therefor by introducing interlayers of synthetic resin in liquid form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
- B32B17/10018—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising only one glass sheet
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/1077—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing polyurethane
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
-
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7825—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing ureum groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Geochemistry & Mineralogy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Laminated Bodies (AREA)
- Joining Of Glass To Other Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
- Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
- Glass Compositions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Optical Communication System (AREA)
- Jib Cranes (AREA)
- Surface Treatment Of Glass (AREA)
Abstract
1. A laminated pane comprising only a glass sheet and a layer of transparent plastics material, characterised in that the layer of transparent plastics material has properties of absorption of energy and interior protection defined by a scratch resistance greater than 20 g measured with the Erichsen type 413 apparatus and an abrasion resistance according to European Standard R43 such that the haze difference is less than 4% and at a thickness of about 0.5 mm a flow stress sigma y at -20 degrees C not exceeding 3 daN/mm**2 , a rupture stress sigma R at +20 degrees C of at least 2 daN/mm**2 , a lengthening at rupture epsilon R at +20 degrees C from 250% to 500%, and a tear resistance Ra at +20 degrees C of at least 9 daN/mm**2 , and in that the layer of plastics material is formed essentially of a polyurethane obtained by continuous reactive casting on a flat horizontal support of a reaction mixture of an isocyanate component and a polyol component, the isocyanate component comprising at least one aliphatic or cycloaliphatic di-isocyanate or a di-isocyanate prepolymer, this component having a viscosity measured at +40 degrees C less than about 5 Pas, the isocyanate component containing urea functions, the content of urea being up to 10% of the total weight of isocyanate component, the urea content preferably being from 5 to 7%, and the polyol component comprising at least one long difunctional polyol of molecular weight from 500 to 4000 and at least one short polyol as a chain lengthening agent, the ratio of isocyanate group equivalents to hydroxyl group equivalents is about 1, and the proportions between the different polyols are selected so that the number of hydroxyl group equivalents due to the short diol represents from 20 to 70% of the total hydroxyl groups.
Description
\ WL
Laminated Safety Pane : 9) 6 i S) OO
RAH CDN
The invention relates to a new laminated pane comprising a glass sheet and a single layer of plastics material.
Laminated panes known as safety panes are generally composed of two glass sheets and an intermediate layer having the property of absorbing energy, generally of polyvinylbutyral. One of the disadvantages of tuis type of laminated pane when it is used as a windscreen for a vehicle, is that in the case of impact of the head of the occupant of the vehicle with the pane the edges of the internal glass sheet which is broken may cause lacerations and other injuries. This is why it has been suggested for example in French Patent Publication 2 187 719 and 2 251 608 to apply to this glass sheet inside the vehicle a sheet of plastics material formed essentially of a thermohardening polyurethane which has anti-laceration properties. Further, this sheet of plastics material is self-healing, that is to say it is of a material in which superficial damage or local impressions disappear rapidly, the speed of disappearance being a function of the nature of the damage and the temperature of the plastics material.
It has also been suggested for example in French Patent
Publication 2 398 606 to provide a laminated pane comprising a glass sheet, a thermoplastics layer having properties of absorbtion of energy and a self-healing coating layer resistant to scratches formed essentially of a thermohardening polyurethane. In this type of pane each of the layers fulfills a particular function, the thermoplastics layer fulfilling essentially the function of absorbing energy but being insufficiently resistant to abrasion or other exterior effects and the coating layer fulfilling the function of protection of the layer absorbing energy but not having itself good properties of energy absorption. 0 > et
Cees i Pn (ib oC Hh
_2- 2 G SEARS)
POO
It has already been suggested for example in Patent
Publications US-3 509 015 and US-3 808 077 to provide laminated panes comprising a ‘glass sheet and a single layer of plastics material having properties of absorption of energy. This type of pane has not apparently given entire satisfaction, probably because of an insufficient resistance to abrasion and scratching of the layer of plastics material used as the external layer.
It is known in a general way that a structure of a laminated pane comprising a single layer of plastics material having simultaneously the properties of absorbing energy and a good resistance to scratching and to attack by exterior agents was unlikely to be satisfactory. In fact, for a man in the art there exists a certain incompatibility between the functions of absorbing energy and resistance to scratching for a single layer. For the layer to have properties of absorption of energy it is believed that it has to have an essentially thermoplastic character. On the other hand, for the layer to have a good resistance to scratching it is believed that it has to have an essentially thermohardening character with a cross-linked structure. These mechanical properties associated with thermoplastic or thermohardening characteristics are described for example in French Patent Publication 2398606 and European Patent
Publication 0054191.
There has now been found a single layer of plastics material which, in a laminated pane structure in which it is associated with a glass sheet fulfills the function of absorbing energy, protection against fragments of glass and which also has a good resistance to abrasion and scratching and to different attacks from exterior agents.
The layer according to the invention is formed in a process which is continuous by reactive casting on a flat horizontal support from which it may be detached, of a , = : / /
JE rie reaction mixture of an isocyanate component and a component having active hydrogens, notably a polyol component, the isocyanate component comprising at least one aliphatic diisocyanate or a cycloaliphatic- diisocyanate or a diisocyanate prepolymer, this component having a viscosity measured at 40°C less than about 5000 centipoises and the polyol component comprising at least one long polyol which is difunctional of molecular weight from 500 to 4000 and at least one short diol as a chain lengthening agent.
By reactive casting is meant casting in the form of a layer or film of a liquid mixture of components in the monomeric or prepolymeric state followed by polymerisation of this mixture by heating. This reactive casting which forms the layer having good mechanical and optical properties will be described more completely in the following description.
The proportions of components of the polyurethane are chosen to obtain preferably a balanced stoichiometric system, that is to say the ratio of equivalent NCO groups provided by the diisocyanate component to equivalent OH groups provided by the polyol component, that is to say the long polyol or polyols and the short diols is of the order of 1. When the ratio NCO/OH is less than 1, the more it decreases the more the desired mechanical properties for this application become less satisfactory. When all the components of the polyurethane are difunctional the lower limit of the NCO/OH ratio for obtaining satisfactory mechanical properties is about 0.9. When one of the components at least is trifunctional this low limit may be lowered to about 0.8. When the ratio NCO/OH is greater than 1, the more it increases and the greater become certain mechanical properties of the layer obtained by reactive casting, for example the layer becoming more rigid, but given the higher cost of the isocyanate component with respect of that of the polyol component, - - 7)
Lota Les ( Lee oc Coteg — 0 the choice of a ratio NCO/OH substantially equal to 1 is a good compromise between the properties obtained and the cost.
The proportions between the long polyol and the short diol may vary as a function of the desired properties as indicated in the following, the number of OH group equivalents due to the short diol however representing generally from 20 to 70% of the total group equivalents of the mixture forming the polyol component in the case where the ratio of OH groups is of the order of 1. When the proportion of short diol is increased, the layer is hardened and its modulus is generally increased.
Suitable diisocyanates which may be used in the invention are chosen especially from the difunctional aliphatic isocyanates following: hexamethylenediisocyanate (HMDI), 2,2,4-trimethyl 1,6-hexanediisocyanate (TMDI), bis U- isocyanatocyclohexylmethane (Hylene W) bis 3-methyl-H4- isocyanatocyclohexylmethane, 2,2 bis (4- isocyanatocyclohexyl) propane, 3-isocyanatomethyl-3,5,5 trimethylcyclohexyl-isocyanate (1PDI), m- xylylenediisocyanate (XDI), m-and p- tetramethylxylylenedi-isocyanate (n- and p- TMXDI), trans-cyclohexane-1,4 diisocyanate (CHDI), and 1,3 - (diisocyanatomethyl)-cyclohexane (hydrogenated XDI).
IPDI is preferably used especially for reasons of cost.
According to one of the aspect of the invention there is used an isocyanate component containing urea functions.
These urea functions improve certain mechanical properties of the layer. The content of the urea may be up to about 10% of - the total weight of the isocyanate component having urea functions. Preferably the content of the urea is from 5 to 7% by weight of the total of said component. For the reason mentioned previously there is
Leal oe CS ny Se CA ; A preferably used 3-isocyanatomethyl-3,5,5- trimethylcyclohexylisocyanate comprising urea functions (IPDI and derivatives thereof).
The long polyols which are suitable are chosen from polyether diols and polyester diols of molecular weight 500 to 4000; the polyesterdiols being products of esterification of a diacid such as adipic acid, succinic acid, palmitic acid, azelaic acid, sebacic acid, orthophthalic acid and a diol such as ethyleneglycol, propanediol -1,3, butanediol -1,4, hexanediol -1,6, and polyetherdiols of general formula
H [o (chp), OH where n = 2 to 6; m is such that the molecular weight is situated in the range 500 to 4000, or polyether-diols of general formula:
CH
HfocH-cH, J, OH where m is such that the molecular weight is also situated in the range 500 to 4000. It is also possible to use polycaprolactonediols.
There is used preferably a polytetramethyleneglycol (n = 4) of molecular weight also equal to about 1000.
The lengthening agents for chains which may be used are the short diols such as ethyleneglycol, propanediol-1,2, propanediol-1,3, butanediol-1,2, -1,3 and -1,4, dimethyl- 2,2-propanediol-1,3 (neopentylglycol), pentanediol-1,5, hexanediol-1,6, . octanediol-1,8, decanediol-1,10, dodecanediol-1,12, cyclohexanedimethanol, bisphenol A, methyl-2 pentanediol-2,4, methyl-3 pentanediol- 2,4, ethyl- 2 hexane-diol-1,3, trimethyl-2,2,4-pentanediol- 1,3, diethylene-glycol, triethyleneglycol, tetraethyleneglycol, butyne-2-diol-1,4, and subst tured ‘ : | Ne TT il
Lobe Sy, NET i Coron My
~6- and/or etherified decynediol, hydroquinone-bis- hydroxyethylether, bisphenol A etherified by two or four propylene oxide groups and dimethylolpropionic acid. In general the shorter the diol the harder the layer.
There is preferably used butanediol-1,4 which is a good compromise to obtain a layer which is neither too hard nor ' too soft which is desired for this type of application.
One of the characteristics of the layer according to the invention is that it is obtained by reactive casting on a flat horizontal support, this reactive casting being already described in French Patent Publication 2 442 128 for obtaining a layer of thermohardening polyurethane from a mixture of trifunctional components providing in surprising manner, according to the invention, in the case of difunctional starting components, a layer which is not entirely thermoplastic when the group NCO/OH ratio is substantially equal to or greater than 1.
Reactive casting implies a rapid polymerisation reaction so that the layer may be formed in a time compatible with industrial manufacture. This requires a higher temperature, of the order of about 100 to 140°C, the temperature at which the secondary reactions of branching which are produced creating for example allophanate groups or biurets between the polyurethane chains, such as: -R-NH-CO-0-R'"=-0-~-
OCN - R - NCO -R-NH-CO=-0-R"=0 - oY - R 4 N - Cor 0 -R'-0 - ‘CO f alophanate he \ \ . i '
NH
CO
- R - N - CO -R' -0 - le to cole Gey I — Chey — hy
JU neve C— ( Hi
Py eam erie or - R" - NH - CO - NH - R" -
OCN - R - NCO - R" - NH - CO - NH - R" - - RY RY - ! CO ,’ “WH - biuret
RT fin co - R" - k - CO - NH - R" -
In these operating conditions, even with difunctional components, when the NCO/OH ratio is substantially equal to or greater than 1, as indicated before, the product obtained is not completely thermoplastic; in fact it is infusible and insoluble in the majority of solvents for polyurethanes such as tetrahydrofuran and dimethylformamide. This does not present any disadvantage when the layer is already formed; on the contrary advantage is taken of the improved mechanical properties for the layer especially regarding the stress at the start of flow y, the stress at rupture R, elongation at rupture
R, and resistance to the start of tearing Ro» the resistance to scratching measured in the ERIKSEN test as described below, or the resistance to abrasion, in comparison with an equivalent system polymerised at low temperature when only a linear polycondensation is produced.
When the NCO/OH ratio is less than 1 and of the order of 0.8 to 0.9, a reticulation of the type described above is produced only to an insignificant extent. fe Ce ee CS my FINE CEE
In one embodiment of the layer of polyurethane according to the invention, the polyol component may contain a small proportion of at least one polyol of functionality greater than two and especially the monomeric aliphatic triols such as glycerol, trimethylolpropane, triols having polyether chains and polycaprolactone triols, the molecular weight of these triols generally being from 90 to 1000, and mixed polyether/polyester polyols of functionality greater than 2, for example of functionality from 2 to 3. The addition of a polyol of functionality greater than 2 gives supplementary bridging connections between the polyurethane chains and may thus increase the cohesion of the layer.
The proportions of the long polyol, the short diol and possibly the polyol of functionality greater than 2 may vary according to the desired properties. There are generally chosen proportions such that for one hydroxyl equivalent the long polyol represents about 0.3 to 0.45 equivalent, the short diol about 0.2 to 0.7 equivalent and the polyol of functionality greater than 2, about 0 to 0.35 equivalent. In these conditions the layer has the following mechanical characteristics measured according to standards AFNOR/NFT 46.002, 51 034 and 54 108.
A stress at the start of flow Oy at -20°C less than or equal to 3 daN/mm?,
A stress at rupture 0” R at + 40°c greater than or equal to 2 daN/mn®,
An elongation at rupture £ R at +20°C from 250 to 500%,
A resistance to the start of tearing Ra at +20°C greater than or equal to 9 daN/mm thickness,
A resistance to scratching greater than 20 g measured according to the test described below,
Le ea lbaeo— JU ee bo a 4 — (Mlle
Resistance to abrasion, with a difference in haze less than 49 measured according to the abrasion test indicated below.
According to one of the aspects of the invention, a part of the polyol component may be replaced by a different product having active hydrogens such as an amine.
According to another embodiment of the layer of plastics material according to the invention, the isocyanate component may contain within limited proportions, for example less than about 15% in NCO equivalents, at least one triisocyanate such as a isocyanate biuret or a triisocyanurate.
To fulfill all the functions which are demanded, the polyurethane layer according to the invention should have a thickness generally greater than 0.4mm and preferably greater than 0.5mm.
The layer according to the invention may contain various additives which generally serve to facilitate manufacture by reactive casting. It may contain a catalyst such as a tin catalyst for example tin dibutyldilaurate, tributyltin oxide, tin octoate, an organomercuric catalyst, for example mercuricphenylester, an amine catalyst such as for example diazabicyclo-(2,2,2)-octane, and 1,8-diazabicyclo (5,4,0)-1 decene-T7. The layer may contain stabilisers such as bis (2,2,6,6-tetramethyl-Ht- piperidyl)sebacate, and a phenolic antioxidant.
The layer may also contain a spreading agent such as a silicone resin, a fluoroalkyl ester, or an acrylic ester.
Examples of manufacture of laminated panes and the layer of plastics material used for this manufacture are described in the following. eer ’ LoL
Example 1
To make the layer of plastics material, there is first prepared the polyol component by. mixing a polytetramethylene glycol of molecular weight 1000 (for example the product sold commercially under the name
Polymeg 1000 by the QUAKER OATS company, with butanediol- 1,4, the proportions of the two constituents being such that the polytetra-methyleneglycol contributes 0.37 equivalent of hydroxyl groups whereas the butanediol-1,4 contributes 0.63.
To the polyol component there is added a stabiliser in an amount of 0.5% by weight of the total weight of polyol component and isocyanate component, a spreading agent in an amount of 0.05% by weight calculated in the same way and a dibutyltin dilaurate catalyst in an amount of 0.02% by weight calculated in the same way.
The isocyanate component used is 3-isocyanatomethyl- 3,5,5-trimethylcyclohexylisocyanate (IPDI) having urea functions obtained by partial hydrolysis of IPDI and having a content of NCO groups of about 31.5% by weight.
The components are used in quantities such that the NCO/OH ratio is 1. After degassing under vacuum of the components, the mixture brought to 40°c is cast by means of a casting head such as that described in French Patent
Publication 2 347 170 on a movable glass support covered with a separating agent. There is thus formed a layer of homogeneous thickness of about 0.755 mm thickness which is subjected to a polymerisation cycle, that is to say a temperature of 120°C for about 25 minutes.
After polymerisation, the layer is removed from the support of glass and forms a sheet which may be stored or used just after for manufacture of laminated panes. ae In i cL A ve Cer A. —_— Cl
To make the pane there is assembled a sheet of plastics material with a sheet of 2.6mm thickness of heated glass.
The glass may possibly be hardened or tempered. This assembly may be carried out in two stages, a first stage consisting of a preliminary assembly obtained by passage of the elements forming the pane between two rollers of a calendar and it is possible to use for this purpose a device described in European Patent Publication 0015209, and a second stage consisting of putting the laminated product in an autoclave where, for about one hour it is subjected to a pressure of about 10 bars at a temperature of about 13°C. This autoclave cycle may possibly be replaced by a stoving cycle at normal pressure.
The pane obtained has an excellent optical quality and a perfect transparency.
The adhesion obtained between the glass sheet and the sheet of plastics material is measured by a peel test described below.
There is cut a strip of 5S5cm width from the covering layer.
The end of the strip is unstuck and there is applied thereto a pulling force perpendicular to the surface of the glass at a pulling speed of 5 cm per minute. The operation is carried out at 20°c. There is noted the pulling force required for unsticking of the strip.
Operating in this way there is obtained a pulling force of 10 daN/5cm.
Trials for resistance to shock at different temperatures are carried out on the pane made according to the example.
A first trial for ‘resistance to shock is carried out at +20°C with a steel ball weighing 2.260 kg (heavy ball test) which is allowed to fall onto the central part of a square glass sample of 30.5 cm side, held on a rigid frame. There is determined the approximate height for i es Tm co (A f ev 7 ( Mls which 90% of the samples tested at the chosen temperature resist fall of the ball without the ball passing through.
For the laminated pane according to the example, the value obtained is 12 metres.
Another trial for resistance to shock is carried out with a steel ball of 0.227 kg weight at 38mm diameter. One trial is carried out at a temperature of -20°C. Another trial is carried out at a temperature at +40°C. The values obtained are respectively 12 and 11 metres.
Taking account of European standard RY43 which is in force, the desired results are at least 4 metres for the heavy 5 ball, at least 8.5 metres for the light ball at -20°C and at least 9 metres for the light ball at +40°C.
The resistance to scratching is measured by a known scratch test called MAR resistance test which is carried out with an ERICHSEN apparatus, type #413. There is measured the loading applied on a diamond head to introduce a persistent scratch on the layer of plastics material assembled with a glass support. The load should be greater than or equal to 20 grams for the layer of plastics material to have the property of being self- healing.
The resistance to scratching measured according to this test, for the pane according to the example is 32 grams.
The resistance to abrasion is measured according to
European standard RY3. For this purpose, an assembled sample of pane is subjected to abrasion by means of an abrasive mill. After 100 rotations in abrasion, there is measured with a spectrophotometer the difference in haziness between the abraded part and non-abraded part.
The difference in haziness (A haze) has to be less than 4% for the layer to have anti-abrasive qualities. oo
Lia baw—y JO dreeel (Cet Mh
-13-~
The layer according to the example has a difference in haze of 0.94%.
The pane according to the example has all the characteristics which render it suitable for use as a vehicle windscreen.
Example 2
The procedure of Example 1 is followed except that the polyol component is formed of a mixture of polytetra- methylene glycol of molecular weight 1000, butanediol-1,H4 and polycaprolactonetriol (for example the product sold commercially under the name Niax 301 by UNION CARBIDE) in respective proportions such that for one total hydroxyl equivalent, there is used 0.35, 0.45 and 0.20 hydroxyl equivalent.
There is made a layer of 0.70mm thickness. The pane obtained shows mechanical and optical characteristics which are completely satisfactory. The values measured in different tests are as follows: - an adhesion of 11 daN/Scm, values of 8 metres with a heavy ball, 11 at 11 metres respectively with a light ball at -20°C and + 40°C. a resistance to scratching of 35 g and a difference in haze on abrasion of 1.2%.
The pane made according to the example is thus suitable for use as a windscreen.
Example 3 J
The procedure of Example 2 is followed except that the proportions between the different polyols are such that for an equivalent total hydroxyl there is used 0.35, 0.55 and 0.10 hydroxyl equivalent respectively for the long - / { \ Co oo 0 ) , : ( Ar ! i polyol, the short diol and the triol.
There is formed a layer of 0.66 mm thickness. The values measured in different tests are as follows: - an adhesion of 11 daN/5 cm, values of 10 metres with the heavy ball, 13.5 and 13.5 metres with the light ball at -20°C and +40°C respectively, a resistance to scratching of 25 g, and a difference in haze on abrasion of 1.2%.
The pane made, according to the example, is thus capable of being used as a windscreen.
Example 4
The procedure of Example 1 is followed except that peclymerisation of the layer is carried out at a temperature of 60°C only for 20 hours.
Trials for resistance to shock give a value with a small ball of -20°C at 6.5 metres which is insufficient.
This example, compared with Example 1 shows the effect of the polymerisation temperature used during reactive casting. In this case this temperature is too low.
Le to Addl On = ! > N Anes Lr _ gr ,
Co —— / ie ol
Claims (8)
- = See a8 il : oo 1 CLAIMS; i / A laminated pane comprising only a glass i sheet and a layer of transparent plastica material, characterised in that the layer of b transparent plastics material has properties of abgorption of energy and interior protection definad by a gcrateh resistance greater than 20 g measured with the Erichsen type 413 apparatus and an abrasion resistance according to 1d European Standard R43 with the haze difference ig leas than 4% and at a thickness of about 0.5 min a flow etress ol at -2A°C not exceeding 3 dal/mn® a rupture stress ok at +2@°C of at least 2 daN/mn®, a lengthening at rupture ER at +2390 from 200% to RAA%, and a tear resistance Ra at +20°0C of at least 9 daN/mm and inthat the layer of plastics material is formed essentially of a polyurethans obtained hy continuous reactive casting on a 1fat 5%) horizontal support of a reaction mixture of an igoeyanate component and a polyol component, the isocyanate component comprising one aliphatic or cycloaliphatic di-isocyanate or a di-isocyanate prepolymer, this component having a viscosity measured at +42°C less than 5 Fas, the isocyanate component containing urea functions, the content of urea being up to 10% of the total weight of 1socysnate component, and the polyol component comprising one long difunctional polyol of molecular welght from 500 to 40PA and one short polyol as a chailn 14 lengthening sgent, the ratio of 1socvanate group equivalents to hydroxyl group equivalents is about 1 and the proportions beteeen the different polyols are so that the number of hydroxyl group equivalents due to the short diol represents from 20 to TO% of the total hydroxyl groups.
- 2. A laminated pane comprising only a glass sheet and a laver of transparent plastics material, characteriged in that the layer of 28 transparent plastics material has properties of absorption of energy and interior protection defined bvy a resistance to scratching greater i than 28 g@ measured with the Erichsen type 413 . apparatus and RB registance to abrasion according to European Standard R43 with the difference in haze ie less than 4% and at a thickness of about 0.5 wn, a flow strees, oY at -20°C not exceeding 3 daN/mus a stress at rupture ar at +20°C of at least 2 dan/un?, a lengthning at rupture ER at +20°C from 258 to 500%, mnd a tear resistance at +20°C of at 19 least 9 daN/wm, and in that the layer of plastics material is formed essentially of a polyurethane obtained by continous reactivve casting on a flat horizontal support of a reaction mixture of an isocyanate component and a polyol component, the isocyanate component comprising one aliphatic or cycloaliphatic di- igocyvanate or a di-igocyanate prepolymer, this component having a viscosity measured at 42°C leas thar 5 Pas. the polyol component 29 comprising one long difunctional rolyol of molecular weight from 580 to 443, one short diol as = chain lengthning agent and one rolyol of functionality greater than 2, the ratio of —_ 31 —isocyanate group equivalent to hydroxyl group equivalents 1s about 1, and the proportions between the different polyols are such that the number of hydroxyl group equivalents due to the short diol represents from 20 to 70% of the total hydroxyl groups.
- 3. A laminated pane according to claim 1 or 2, characterised in that the isocyanate component po comprises 3-isocyanatomethyl-3,5, 5- 12 trimethylcyclohexylisooyanate.
- 4. a laminated pane according to claim 3 characlerised in that the lsocyauste component is formed of J-isocyanatomethyl-3,5,5- trimethyloyclohexylisocyanate having urea i : 15 groups and in Lthat the palyol component is formed of polybetramethylene glycol and 1,4- butanediol.
- 5. A laminated pane according to claim 2 4 characterised in that the rolyol of za functionality greater than 2 is a polycaprolactonetriol. ¥ ¢:
- 6. A laminated pane according to one of claim 1 or 2 characterised in that for one equivalent b of hydroxyl groups in total, the long polyol represents 0.30 to 0.45 equivalent, the short diol 0.2 to 0.7 equivalent and the polyol of functionality greater than 2 has O to 0.35 equivalent.
- 7. A laminated pane according to one of claim 12 1 or 2 characterised in that the polyurethane layer having properties of absorption of energy and interior protection further comprises additives such as a catalyst, a spreading agent and a stabiliser.
- 8. A laminated pane according to any one of claim 1 or 2, characterised in that the layer of transparent plastics material is obtained by 3 reactive casting using a polymerisation 8 b temperature greater bthan 88°C, L:*2. A laminated pane according to one of claim 1 or 2, characterised in that the isocyanate component further contains at least one Lri- isocyanate,yo .
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8311507A FR2549037B1 (en) | 1983-07-11 | 1983-07-11 | SAFETY SHEET GLAZING |
Publications (1)
Publication Number | Publication Date |
---|---|
PH26588A true PH26588A (en) | 1992-08-19 |
Family
ID=9290703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PH30957A PH26588A (en) | 1983-07-11 | 1984-07-10 | Laminated safety pane |
Country Status (24)
Country | Link |
---|---|
EP (1) | EP0131523B1 (en) |
JP (1) | JPS6071253A (en) |
KR (1) | KR930000775B1 (en) |
AT (1) | ATE31896T1 (en) |
AU (1) | AU575059B2 (en) |
BR (1) | BR8403426A (en) |
CA (1) | CA1261241A (en) |
DE (1) | DE3468647D1 (en) |
DK (1) | DK163039C (en) |
ES (1) | ES534172A0 (en) |
FI (1) | FI77602C (en) |
FR (1) | FR2549037B1 (en) |
HU (1) | HU194770B (en) |
IE (1) | IE57796B1 (en) |
IL (1) | IL72360A (en) |
IN (1) | IN162382B (en) |
MA (1) | MA20175A1 (en) |
NO (1) | NO161967C (en) |
NZ (1) | NZ208854A (en) |
PH (1) | PH26588A (en) |
PT (1) | PT78883B (en) |
SU (1) | SU1491326A3 (en) |
YU (1) | YU43368B (en) |
ZA (1) | ZA845292B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4592947A (en) * | 1984-06-04 | 1986-06-03 | Sierracin Corporation | Low temperature laminatable polyurethane |
FR2576011B1 (en) * | 1985-01-15 | 1991-10-31 | Saint Gobain Vitrage | PROCESS AND DEVICE FOR MANUFACTURING SAFETY GLAZING |
FR2576012B1 (en) * | 1985-01-15 | 1991-11-22 | Saint Gobain Vitrage | PROCESS AND DEVICE FOR MANUFACTURING SAFETY GLAZING |
IT1204812B (en) * | 1986-02-19 | 1989-03-10 | Siv Soc Italiana Vetro | PROCEDURE FOR THE MANUFACTURE OF A SAFETY GLASS FOR VEHICLES AND BUILDINGS, AND PRODUCT SO OBTAINED |
DE3881570T2 (en) * | 1987-03-17 | 1994-02-03 | Asahi Glass Co Ltd | Reactive curable composition and products containing the cured products of this composition. |
DE4021113A1 (en) * | 1990-07-03 | 1992-01-09 | Bayer Ag | Adhesives based on polyols and polyisocyanates |
DE4124839C1 (en) * | 1991-07-26 | 1992-07-09 | Vegla Vereinigte Glaswerke Gmbh, 5100 Aachen, De | |
US5846897A (en) * | 1997-03-19 | 1998-12-08 | King Industries, Inc. | Zirconium urethane catalysts |
FR2827855B1 (en) | 2001-07-25 | 2004-07-02 | Saint Gobain | GLAZING PROVIDED WITH A STACK OF THIN FILMS REFLECTING INFRARED AND / OR SOLAR RADIATION |
EA008369B1 (en) * | 2005-04-12 | 2007-04-27 | Светлана Сергеевна Стацевич | Method of advertising information and information device |
US7595759B2 (en) * | 2007-01-04 | 2009-09-29 | Apple Inc. | Handheld electronic devices with isolated antennas |
FR3013043B1 (en) | 2013-11-08 | 2015-11-20 | Saint Gobain | SUBSTRATE COATED WITH A FUNCTIONAL LAYER STACK HAVING IMPROVED MECHANICAL PROPERTIES |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4024113A (en) * | 1976-04-28 | 1977-05-17 | Ppg Industries, Inc. | Polycarbonate polyurethanes based on particular aliphatic/cycloaliphatic polycarbonates |
DE2629779C3 (en) * | 1976-07-02 | 1985-04-04 | Saint Gobain | Process for the production of a two-layer film with self-healing properties using polyurethanes as a shatterproof layer on safety glass |
FR2385751A1 (en) * | 1977-03-28 | 1978-10-27 | Ppg Industries Inc | Polyurethane free from ether linkages - used for glazing or optical lenses, and hard, flexible and resist to weathering |
FR2442128A1 (en) * | 1978-11-23 | 1980-06-20 | Saint Gobain | PROCESS FOR PRODUCING SHEETS OF PLASTIC MATERIAL |
FR2470682A1 (en) * | 1979-12-06 | 1981-06-12 | Saint Gobain | PROCESS FOR PRODUCING LAMINATES, LAMINATES OBTAINED AND GLUE USED THEREIN |
CA1174577A (en) * | 1980-04-30 | 1984-09-18 | Vernon G. Ammons | Polyurethane composition for safety glass interlayer |
FR2496089A1 (en) * | 1980-12-11 | 1982-06-18 | Saint Gobain Vitrage | SECURITY SHEET GLAZING |
JPS57199649A (en) * | 1981-06-03 | 1982-12-07 | Asahi Glass Co Ltd | Polyurethane sheet and glass-polyurethane laminated sheet |
DE3135672A1 (en) * | 1981-09-09 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Use of low-viscosity self-curing mixtures for polyurethane interlayers in laminated panes |
FR2549036B1 (en) * | 1983-07-11 | 1985-10-18 | Saint Gobain Vitrage | SAFETY SHEET GLAZING |
-
1983
- 1983-07-11 FR FR8311507A patent/FR2549037B1/en not_active Expired
-
1984
- 1984-07-09 DK DK337184A patent/DK163039C/en not_active IP Right Cessation
- 1984-07-10 IL IL7236084A patent/IL72360A/en not_active IP Right Cessation
- 1984-07-10 DE DE8484401464T patent/DE3468647D1/en not_active Expired
- 1984-07-10 HU HU842694A patent/HU194770B/en not_active IP Right Cessation
- 1984-07-10 FI FI842766A patent/FI77602C/en not_active IP Right Cessation
- 1984-07-10 IN IN496/CAL/84A patent/IN162382B/en unknown
- 1984-07-10 SU SU843791615A patent/SU1491326A3/en active
- 1984-07-10 NO NO842804A patent/NO161967C/en unknown
- 1984-07-10 IE IE1759/84A patent/IE57796B1/en not_active IP Right Cessation
- 1984-07-10 PT PT78883A patent/PT78883B/en unknown
- 1984-07-10 AU AU30456/84A patent/AU575059B2/en not_active Ceased
- 1984-07-10 YU YU1206/84A patent/YU43368B/en unknown
- 1984-07-10 ZA ZA845292A patent/ZA845292B/en unknown
- 1984-07-10 ES ES534172A patent/ES534172A0/en active Granted
- 1984-07-10 BR BR8403426A patent/BR8403426A/en not_active IP Right Cessation
- 1984-07-10 EP EP84401464A patent/EP0131523B1/en not_active Expired
- 1984-07-10 NZ NZ208854A patent/NZ208854A/en unknown
- 1984-07-10 PH PH30957A patent/PH26588A/en unknown
- 1984-07-10 JP JP59141570A patent/JPS6071253A/en active Granted
- 1984-07-10 AT AT84401464T patent/ATE31896T1/en active
- 1984-07-11 KR KR1019840004059A patent/KR930000775B1/en not_active IP Right Cessation
- 1984-07-11 CA CA000458655A patent/CA1261241A/en not_active Expired
- 1984-07-11 MA MA20399A patent/MA20175A1/en unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5100731A (en) | Reaction curable composition and products comprising a cured product of the composition | |
FI77601C (en) | Multi-layer safety glass. | |
US4671838A (en) | Preparation of bilayer laminate and preformed sheet for use therein | |
US5766755A (en) | Laminated safety pane for aircraft | |
FI84794C (en) | FOERFARANDE OCH ANORDNING FOER FRAMSTAELLNING AV EN FILM AV PLASTMATERIAL MED HOEG OPTISK KVALITET. | |
PH26588A (en) | Laminated safety pane | |
EP0320871B1 (en) | Bilayer windshield with an abrasion and solvent resistant polyurethane protective coating | |
US5039573A (en) | Polyurethane layer possessing energy-absorbing properties and its use in safety glass | |
KR920002355B1 (en) | Sheet of transparent plastics material | |
US4923757A (en) | Bilayer windshield with an abrasion and solvent resistant polyurethane protective coating | |
US4789600A (en) | Method for manufacturing laminated glasses | |
US4732725A (en) | Process and device for the production of a safety pane | |
AU625119B2 (en) | Bonding polyvinyl butyral and polyurethane and method for obtaining same |