DE3112541A1 - Verfahren zum herstellen von sicherheitsglas mit einer zwischenschicht aus polyurethan - Google Patents
Verfahren zum herstellen von sicherheitsglas mit einer zwischenschicht aus polyurethanInfo
- Publication number
- DE3112541A1 DE3112541A1 DE19813112541 DE3112541A DE3112541A1 DE 3112541 A1 DE3112541 A1 DE 3112541A1 DE 19813112541 DE19813112541 DE 19813112541 DE 3112541 A DE3112541 A DE 3112541A DE 3112541 A1 DE3112541 A1 DE 3112541A1
- Authority
- DE
- Germany
- Prior art keywords
- polyurethane
- glass
- reaction mixture
- toluene diisocyanate
- molecular weight
- 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.)
- Withdrawn
Links
- 229920002635 polyurethane Polymers 0.000 title claims description 35
- 239000004814 polyurethane Substances 0.000 title claims description 35
- 239000011229 interlayer Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000005336 safety glass Substances 0.000 title description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 239000011521 glass Substances 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 13
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 10
- 229920001281 polyalkylene Polymers 0.000 claims description 10
- 239000002131 composite material Substances 0.000 claims description 9
- 238000005266 casting Methods 0.000 claims description 8
- 229920006264 polyurethane film Polymers 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 238000003475 lamination Methods 0.000 claims description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000001029 thermal curing Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 13
- 150000002009 diols Chemical class 0.000 description 11
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 5
- 239000004970 Chain extender Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920001692 polycarbonate urethane Polymers 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000005340 laminated glass Substances 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- -1 polyoxyethylene carbonate Polymers 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 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
- 238000009826 distribution Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C09J175/08—Polyurethanes from polyethers
-
- 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
- B32B38/00—Ancillary operations in connection with laminating processes
- B32B2038/0052—Other operations not otherwise provided for
- B32B2038/0076—Curing, vulcanising, cross-linking
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
- Joining Of Glass To Other Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14507480A | 1980-04-30 | 1980-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3112541A1 true DE3112541A1 (de) | 1982-01-28 |
Family
ID=22511500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813112541 Withdrawn DE3112541A1 (de) | 1980-04-30 | 1981-03-30 | Verfahren zum herstellen von sicherheitsglas mit einer zwischenschicht aus polyurethan |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS56164042A (enrdf_load_stackoverflow) |
| BE (1) | BE888612A (enrdf_load_stackoverflow) |
| CA (1) | CA1174577A (enrdf_load_stackoverflow) |
| DE (1) | DE3112541A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2481690A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2074940B (enrdf_load_stackoverflow) |
| IT (1) | IT1137546B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3519041A1 (de) * | 1984-06-04 | 1985-12-05 | Sierracin Corp., Sylmar, Calif. | Lichtdurchlaessiger gegenstand, verfahren zur herstellung eines lichtdurchlaessigen laminats und bei niedriger temperatur laminierbares polyurethan |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549037B1 (fr) * | 1983-07-11 | 1985-10-18 | Saint Gobain Vitrage | Vitrage feuillete de securite |
| FR2548956B1 (fr) * | 1983-07-11 | 1985-10-18 | Saint Gobain Vitrage | Feuille en matiere plastique transparente de haute qualite optique |
| FR2549036B1 (fr) * | 1983-07-11 | 1985-10-18 | Saint Gobain Vitrage | Vitrage feuillete de securite |
| FR2576012B1 (fr) * | 1985-01-15 | 1991-11-22 | Saint Gobain Vitrage | Procede et dispositif pour la fabrication d'un vitrage de securite |
| JPS61177241A (ja) * | 1985-02-04 | 1986-08-08 | 旭硝子株式会社 | 積層安全ガラスおよびその製造方法 |
| US4814412A (en) * | 1987-12-17 | 1989-03-21 | W. L. Gore & Associates, Inc. | Two component polyurethane system for casting expanded polytetrafluoroethylene |
| DE4301355A1 (de) * | 1993-01-20 | 1994-07-21 | Basf Ag | Klebfreie, hochelastische mono- und multifile Polyurethan-Elastomerfäden, Verfahren zu ihrer Herstellung und ihre Verwendung sowie teilvernetzte thermoplastische Polyurethane hierfür |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2244595A1 (de) * | 1971-09-16 | 1973-07-19 | Ppg Industries Inc | Verfahren und vorrichtung zur herstellung eines aus einer kunststoffolie und einer glasscheibe bestehenden verglasungsmaterials |
| DE2240580A1 (de) * | 1972-08-18 | 1974-02-28 | Ppg Industries Inc | Mehrschichtige fenster |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE610315A (enrdf_load_stackoverflow) * | 1965-02-24 | 1900-01-01 | ||
| US3620905A (en) * | 1969-10-21 | 1971-11-16 | Du Pont | Optically clear thermoplastic polyurethanes |
| GB1263880A (en) * | 1970-09-17 | 1972-02-16 | Du Pont | Improvements in and relating to safety glass |
| BE787039A (fr) * | 1971-08-02 | 1973-02-01 | Ppg Industries Inc | Produits feuilletes transparents, a bonne resistance au choc, en polyether-urethanne |
| BE794206A (fr) * | 1972-01-19 | 1973-07-18 | Monsanto Co | Intercalaire en polyurethane pour verre de securite feuillete |
| US4085092A (en) * | 1974-05-30 | 1978-04-18 | Ppg Industries, Inc. | Transparent, optically clear poly(lactone-urethane) interlayers for laminated safety glass |
| US4035548A (en) * | 1974-05-30 | 1977-07-12 | Ppg Industries, Inc. | Laminated articles prepared from transparent, non-blooming poly(lactone-urethane) interlayers |
-
1981
- 1981-02-10 CA CA000370515A patent/CA1174577A/en not_active Expired
- 1981-03-03 JP JP3110181A patent/JPS56164042A/ja active Granted
- 1981-03-18 FR FR8105395A patent/FR2481690A1/fr active Granted
- 1981-03-30 DE DE19813112541 patent/DE3112541A1/de not_active Withdrawn
- 1981-04-22 IT IT21327/81A patent/IT1137546B/it active
- 1981-04-29 GB GB8113145A patent/GB2074940B/en not_active Expired
- 1981-04-29 BE BE0/204638A patent/BE888612A/fr not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2244595A1 (de) * | 1971-09-16 | 1973-07-19 | Ppg Industries Inc | Verfahren und vorrichtung zur herstellung eines aus einer kunststoffolie und einer glasscheibe bestehenden verglasungsmaterials |
| DE2240580A1 (de) * | 1972-08-18 | 1974-02-28 | Ppg Industries Inc | Mehrschichtige fenster |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3519041A1 (de) * | 1984-06-04 | 1985-12-05 | Sierracin Corp., Sylmar, Calif. | Lichtdurchlaessiger gegenstand, verfahren zur herstellung eines lichtdurchlaessigen laminats und bei niedriger temperatur laminierbares polyurethan |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1174577A (en) | 1984-09-18 |
| GB2074940A (en) | 1981-11-11 |
| IT8121327A0 (it) | 1981-04-22 |
| FR2481690B1 (enrdf_load_stackoverflow) | 1984-12-21 |
| JPH0323495B2 (enrdf_load_stackoverflow) | 1991-03-29 |
| GB2074940B (en) | 1984-03-28 |
| FR2481690A1 (fr) | 1981-11-06 |
| BE888612A (fr) | 1981-10-29 |
| IT1137546B (it) | 1986-09-10 |
| JPS56164042A (en) | 1981-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal | ||
| 8180 | Miscellaneous part 1 |
Free format text: WIEDEREINSETZUNG IN DEN VORHERGEHENDEN STAND |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |