GB2259669A - Laminated glass - Google Patents
Laminated glass Download PDFInfo
- Publication number
- GB2259669A GB2259669A GB9219792A GB9219792A GB2259669A GB 2259669 A GB2259669 A GB 2259669A GB 9219792 A GB9219792 A GB 9219792A GB 9219792 A GB9219792 A GB 9219792A GB 2259669 A GB2259669 A GB 2259669A
- Authority
- GB
- United Kingdom
- Prior art keywords
- laminated glass
- thermosetting resin
- vinyl acetate
- ethylene
- glass
- 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.)
- Granted
Links
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
- B32B17/10009—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
- B32B17/10036—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 two outer glass sheets
-
- 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
-
- 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
- B32B17/10697—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 being cross-linked
-
- 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
- B32B17/10788—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 ethylene vinylacetate
-
- 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
- B32B2315/00—Other materials containing non-metallic inorganic compounds not provided for in groups B32B2311/00 - B32B2313/04
- B32B2315/08—Glass
Landscapes
- Laminated Bodies (AREA)
- Joining Of Glass To Other Materials (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Laminated glass comprising a pair of glass plates and a sheet of a thermosetting resin made of an ethylene-vinyl acetate-vinyl alcohol terpolymer between the glass plates which has been cured so that the plates are integrated.
Description
Laminated Glass This invention relates to laminated glass which may be
used as windscreens or rear or side windows in automobiles and as window glass in buildings. A polyvinyl butyral resin has conventionally been used as the intermediate layer of laminated glass, but the resin is thermoplastic and this leads to the following problems: (1) because of the relatively low softening point, slippage between the bonded glass plates and bubble formation tend to take place due to heating; (2) because the resin is considerably affected by moisture, the intermediate layer gradually whitens from its edges and its adhesion to the glass plates tends to decrease when the laminated glass is allowed to stand in a high humidity atmosphere for a long time; (3) the resistance to impact fractures depends on temperature, and the resistance to perforation, in particular, rapidly decreases at a temperature above the room temperature i.e. a temperature of about 300C or higher. To solve the above-mentioned problems associated with the use of polyvinyl butyral resins, the present inventors have previously suggested laminated glass which has been prepared by providing a sheet of a thermosetting resin of ethylene-vinyl acetate copolymer to which an organic peroxide has been added, between glass plates, and thermosetting the resinous layer to cure and to integrate the layers (for example, see Japanese Patent Laid-open No. 196747/1982). However, with regard to safety (resistance to impact fractures and to perforation), which is one of the major reasons for using laminated glass, the laminated glass disclosed in Japanese Patent Laid-open - 2 No. 196747/1982 and other patents fails to completely satisfy this requirement under extensive conditions.
An object of the present invention is to provide laminated glass which excels in its resistance to impact fractures and to perforation and gives rise to no danger even when broken by external forces.
A further object of this invention is to provide laminated glass which is very useful as windscreens, rear and side windows for automobiles and as window glass in buildings.
Thus, according to one aspect of the present invention there is provided a laminated glass comprising a pair of glass plates and between said glass plates a sheet of a thermosetting resin made of an ethylene-vinyl acetate-vinyl alcohol terpolymer, said thermosetting resin being cured so that said plates are integrated. According to a further aspect there is provided a method of manufacturing a laminated glass, said method comprising curing a sheet of a thermosetting resin made of an ethylenevinyl acetate-vinyl alcohol terpolymer between a pair of glass plates so as to cause integration of said plates. There is also provided a laminated glass when manufactured by such a method.
In the present invention, a sheet of an ethylenevinyl acetate-vinyl alcohol terpolymer is sandwiched between two glass plates and the resinous layer is cured, thus integrating all the components. For example, an ethylene-vinyl acetate-vinyl alcohol terpolymer may preferably be prepared by saponifying 1 to 70%, more preferably 20 to 60%, of the vinyl acetate in an ethylene-vinyl acetate copolymer. Then an organic peroxide may preferably be added to this terpolymer as a curing agent, and the thermosetting polymer thus obtained is sandwiched between two glass plates. And then, the terpolymer is thermoset to integrate all the components.
The ethylene-vinyl acetate copolymer employed for Q ii 1 preparing the ethylenevinyl acetate-vinyl alcohol terpolymer used in this invention should preferably contain 10 to 50 weight %, most preferably 15 to 40 weight %, of vinyl acetate. If the content of vinyl acetate is less than 10 weight %, the crosslinked polymer obtained by thermal curing is not sufficiently transparent, while a vinyl acetate content exceeding 50 weight % results in the production of laminated glass with insufficient resistance to impact fractures and to perforation.
Such an ethylene-vinyl acetate copolymer can be easily converted into an ethylene-vinyl acetate-vinyl alcohol terpolymer by hydrolysis in the presence of a suitable alkaline catalyst.
If the saponification rate of the vinyl acetate in the ethylene-vinyl acetate copolymer is less than 1% or higher than 70%, the improvements by the process of this invention cannot be expected, while a markedly high degree of improvements can be obtained when the saponification rate is in the range of 20 to 60%.
An organic peroxide may be used as a curing catalyst for the ethylenevinyl acetate-vinyl alcohol terpolymer, in particular an organic peroxide which decomposes at a temperature of 100'C or higher to produce radicals. When considering stability during blending, the use of a peroxide whose decomposition point for a half-life period of ten hours is 70'C or higher is preferable. Typical examples of such a peroxide which may be used are 2,5-dimethylhexane-2,5dihydroperoxide, 2,5-dimethyl-2,5-di(tbutylperoxy)hexyne-3, di-t-butylperoxide, t-butyl cumyl peroxide, 2,5dinethyl-2,5-di(t-butylperoxy)hexane, dicumyl peroxide, a,al-bis(tbutylperoxyisopropyl)benzene, nbutyl-4,4-bis(t-butylperoxy)valerate, 2,2bis(tbutylperoxy)butane, 1,1-bis(t-butylperoxy)cyclohexane, 1,1-bis(tbutylperoxy) 3,3,5-trimethylcyclohexane, tbutyl peroxybenzoate and benzoyl peroxide. Any of these organic peroxides may be used either alone or in combination, and the amount to be added should preferably be 5% or less, more preferably in the range of 0.1 to 5%, based on the weight of the ethylene-vinyl acetate- vinyl alcohol terpolymer.
At least one compound selected from acryloxy-groupcontaining compounds, inethacryloxy-group-containing compounds and allyl-group-containing compounds may also_ be added as a curing assistant in order to enhance the initial modulus of the thermosetting resin comprising an ethylene- vinyl acetate-vinyl alcohol terpolymer, thereby improving its resistance to perforation. As the acryloxy-group-containing compound and the methacryloxygroup-containing compound, there may be used an acrylic acid or methacrylic acid derivative, such as esters thereof; as the alcohol radical component of the ester, there is preferred cyclohexyl, tetrahydrofurfuryl, aminoethyl, 2-hydroxyethyl, 3-hydroxypropyl and 3chloro-2-hydroxypropyl groups in addition to alkyl groups, such as methyl, ethyl, dodecyl, stearyl and lauryl groups. Furthermore, esters derived from a polyfunctional alcohol, such as ethylene glycol, triethylene glycol and polyethylene glycol, may also be used.
Preferred examples of the allyl-group-containing compound are diallyl phthalate, diallyl fumarate, diallyl maleate, triallyl isocyanurate and triallyl cyanurate.
The amount of these compounds to be added should preferably be 50% or less, most preferably in the range of 0.1 to 50%, based on the weight of the ethylene-vinyl acetate-vinyl alcohol terpolymer.
A silane coupling agent may also be added as an adhesion improver to further enhance the adhesion of the thermosetting resin comprising an ethylene-vinyl acetate-vinyl alcohol terpolymer to the glass plates. Examples of suitable silane coupling agents are known Y c 1 compounds such as y-chloropropylmethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyltris(p-methoxy-ethoxy)silane, ymethacryloxypropyltrimethoxysilane, P-(3,4ethoxycyclohexyl)ethyltrimethoxysilane, y-glycidoxypropyltrimethoxysilane, vinylthiacetoxysilane, y-mercaptopropyltrimethoxysilane, y-aminopropyltriethoxysilane, and N-P(aminoethyl)-1aminopropyltrinethoxysilane. The amount of such silane coupling agents to be added may be 5% or less, preferably in the range of 0.1 to 4%, based on the weight of the ethylene-vinyl acetatevinyl alcohol terpolymer.
A polymerisation inhibitor, such as hydroquinone, hydroquinone monomethyl ether, p-benzoquinone and methyl-hydroquinone, may also be added, as required, in an amount of 5% or less, preferably in the range of 0.1 to 5%, based on the weight of the ethylene-vinyl acetate-vinyl alcohol terpolymer to enhance the stability of the resin. In addition, colorants, UV absorbers, aging inhibitors, discoloration inhibitors and other additives may also be added as required.
A natural or synthetic hydrocarbon resin may also be used in combination with the thermosetting resin comprising an ethylene-vinyl acetate-vinyl alcohol terpolymer to further enhance the resistance to perforation. Examples of preferred natural hydrocarbon resins are rosin, derivatives thereof and terpene resins. Preferred examples of rosin are gum resin, tall oil resin and wood resin; examples of rosin derivatives are hydrogenated products, disproportionation products, polymers, esters and metal salts of the above-mentioned rosins; and examples of terpene resin are a-pinene, Ppinene and terpene phenol resins. In addition, dammar, copal and shellac may also be used as the natural resin.
As a synthetic resin, one may preferably use petroleum resins, phenolic resins and xylenic resins. Examples of petroleum resins are aliphatic petroleum resins, aromatic petroleum resins, alicyclic petroleum resins, copolymeric petroleum resins, hydrogenated petroleum resins, petroleum resins of pure monomer type and cumarone-indene resins; examples of phenolic resins are alkylphenolic resins and modified phenolic resins; and examples of xylenic resins are xylene resins and modified xylene resins.
Those hydrocarbon resins having a weight-average molecular weight in the range of 200 to 50000, particularly in the range of 200 to 10000, are preferred. Such a hydrocarbon resin should preferably be added in an amount of 1 to 100%, most preferably 2 to 80%, based on the weight of the ethylene-vinyl acetatevinyl alcohol terpolymer.
The thermosetting resin used in this invention may be easily prepared by mixing prescribed amounts of the above-mentioned components using conventional methods.
A sheet of a thermosetting resin obtained as mentioned above, formed by a method commonly employed, is sandwiched between two glass plates, and the thermosetting resin is then cured by heating at the curing temperature to integrate all the components, thereby preparing the laminated glass of this invention.
The laminated glass of this invention has a markedly high degree of resistance to impact and to perforation, causes no danger even when broken by external forces, and is therefore very useful as windscreens and rear and side windows for automobiles and as window glass in buildings.
The thermosetting resin comprising an ethylenevinyl acetate-vinyl alcohol terpolymer, when used as the intermediate layer of laminated glass, shows a markedly high degree of resistance to impact and to perforation.
In addition, a high degree of safety is assured even when the glass is broken by external forces because of the high tear strength of the intermediate layer made of this thermosetting resin.
- 7 The invention will now be illustrated by means of the following nonlimiting examples.
Examples Example 1 A thermosetting resin was prepared by mixing the components shown in Table 1 in a roll mill heated to 80C. The ethylene-vinyl acetate-vinyl alcohol terpolymer was prepared by saponifying pellets of an ethylene- vinyl acetate copolymer in methanol using an alkaline catalyst. NMR analysis showed that 60% of the vinyl acetate had been saponified. The ethylene-vinyl acetate copolymer used was 11Ultrasen-63411 (a trade mark of Toso Co., Ltd; vinyl acetate content: 26 weight %).
A 0.76 mm thick sheet was made from the thermosetting resin obtained above by using a press, and the sheet was sandwiched between two float- glass plates (3 mm. thick) previously washed and dried. The combined materials thus obtained were put into a rubber bag, deaerated under reduced pressure, and subjected to preliminary contact bonding at a temperature of 80'C. The prebonded laminated glass was then put into an oven and treated at 130'C for 30 minutes.
The laminated glass was obtained was subjected to a shot-bag test according to the method specified by JIS R3205 (1983), and no cracking was observed at a drop height of 120 cm in any of the four samples tested.
Separately, the thermosetting resin was treated using a press at 130C for 30 minutes, giving a sheet 2.0 mm thick, and this sheet was subjected to a tearing test according to the method specified by JIS K6301 (1975), showing a high vale of 50.5 Kgf/cm.
These results are summarized in Table 1.
Example 2
An experiment was carried out in the same manner as in Example 1, except that the saponification rate of the 8 vinyl acetate in the ethylene-vinyl acetate-vinyl alcohol terpolymer was adjusted to 22%, and the results obtained are also shown in Table 1. The laminated glass obtained was highly transparent and showed no optical distortion.
Comparative Example 1 An experiment was carried out in the same manner as, in Example 1, except that the vinyl acetate in the ethylene-vinyl acetate-vinyl alcohol terpolymer was not saponified, and the results are also shown in Table 1.
As is apparent from Table 1, the laminated glass of the present invention has a high degree of resistance to impact fractures, and causes no danger even when it is broken because of the high tear strength of the intermediate layer.
7 -3k Table 1
Example 1 Example 2 Comparative Example 1
Saponification rate of vinyl acetate in ethylene- vinyl acetate-vinyl alcohol terpolymer 60 22 - Composition (parts by weight):
Ethylene-vinyl acetate-vinyl alcohol terpolymer 100 100 0 Ethylene-vinyl acetate copolymer 0 0 100 Triallyl isocyanurate 3 3 3 y-Methacryloxypropyltrimethoxysilane 0.5 0.5 0.5 1,1-Bis(t-butylperoxy)-3,3,5-trimethyl- cyclohexane 3 3 3 Test results:
Tear strength (Kgf/cm) 50.5 29.2 15.7 Short-bag test (drop height: 120 cm) No crack Crack length Crack length mm 200 mm j -
Claims (17)
1. A laminated glass comprising a pair of glass plates and between said glass plates a sheet of a thermosetting resin made of an ethylene-vinyl acetate-vinyl alcohol terpolymer, said thermosetting resin being cured so that said plates are integrated.
2. A laminated glass as claimed in claim 1 wherein said thermosetting resin has been cured in the presence of an organic peroxide curing agent.
3. A laminated glass as claimed in claim 1 or claim 2, wherein said thermosetting resin is a terpolymer prepared by saponifying 1 to 70% of vinyl acetate in an ethylene-vinyl acetate copolymer and said terpolymer has been cured with an organic peroxide curing agent.
4. A laminated glass as claimed in any one of the preceding claims, wherein the ethylene-vinyl acetate copolymer, which is the starting material for preparing said ethylene-vinyl acetate-vinyl alcohol terpolymer, contains vinyl acetate in an amount of 10 to 50 weight
5. A laminated glass as claimed in any one of claims to 4, wherein said organic peroxide curing agent is an organic peroxide which decomposes at a temperature of 1000C or higher to produce radicals.
6. A laminated glass as claimed in any one of claims 2 to 4, wherein said organic peroxide curing agent has a decomposition point of-700C or higher for a half-life period of ten hours.
7. A laminated glass as claimed in any one of claims 2 to 6, wherein said organic peroxide curing agent is at A least one compound selected from 2,5-dimethylhexane-2,5dihydroperoxide, 2, 5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, di-t-butylperoxide, t-butyl cumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumyl peroxide, a,al-bis(t-butylperoxyisopropyl)benzene, nbutyl-4,4-bis(tbutylperoxy)valerate, 2,2-bis(tbutylperoxy)butane, 1,1-bis(tbutylperoxy)cyclohexane, 1,1-bis(t-butylperoxy) 3,3,5trimethylcyclohexane, tbutyl peroxybenzoate and benzoyl peroxide.
8. A laminated glass as claimed in any one of the preceding claims, wherein the amount of the curing agent added is 0.1 to 5% based on the weight of the ethylenevinyl acetate-vinyl alcohol terpolymer.
9. A laminated glass as defined in any one of the preceding claims, wherein at least one member selected from acryloxy-group-containing compounds, methacryloxygroup-containing compounds and allyl-groupcontaining compounds is added to said thermosetting resin as a curing assistant in order to enhance its initial modulus, thereby improving its resistance to perforation.
10. A laminated glass as claimed in any one of the preceding claims, wherein a silane coupling agent is added to said thermosetting resin as an adhesion improver to further enhance its adhesion to the glass plates.
11. A laminated glass as claimed in any one of the preceding claims, wherein at least one polymerization inhibitor selected from hydroquinone, hydroquinone monomethyl ether, p-benzoquinone and methylhydroquinone is added to said thermosetting resin in an amount of 5% or less based on the weight of said terpolymer to enhance its stability.
12. A laminated glass as claimed in any one of the preceding claims, comprising at least one additive selected from colorants, UV absorbers, aging inhibitors and discoloration inhibitors.
S
13. A laminated glass as claimed in any one of the preceding claims, wherein a hydrocarbon resin is used in combination with said thermosetting resin to enhance its resistance to perforation.
14. A laminated glass as claimed in claim 13, wherein said hydrocarbon resin has a weight-average molecular weight of 200 to 50000 and is used in an amount of 1 to 100% based on the weight of said thermosetting resin.
15. A laminated glass as claimed in claim 1 substantially as herein defined with reference to the Examples.
16. A method of manufacturing a laminated glass, said method comprising curing a sheet of a thermosetting resin made of an ethylene-vinyl acetatevinyl alcohol terpolymer between a pair of glass plates so as to cause integration of said plates.
17. A laminated glass when manufactured by a method as claimed in claim 16.
_:4
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23951491A JP3213979B2 (en) | 1991-09-19 | 1991-09-19 | Laminated glass |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9219792D0 GB9219792D0 (en) | 1992-10-28 |
| GB2259669A true GB2259669A (en) | 1993-03-24 |
| GB2259669B GB2259669B (en) | 1995-09-20 |
Family
ID=17045933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9219792A Expired - Lifetime GB2259669B (en) | 1991-09-19 | 1992-09-18 | Laminated glass |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP3213979B2 (en) |
| DE (1) | DE4231199C2 (en) |
| GB (1) | GB2259669B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0743175A2 (en) * | 1995-05-17 | 1996-11-20 | Bridgestone Corporation | Laminated glass |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4430311C1 (en) * | 1994-08-26 | 1996-04-25 | Buna Sow Leuna Olefinverb Gmbh | Moulding cpd. used in intermediate layers for laminated glass |
| DE19643404A1 (en) * | 1996-10-21 | 1998-04-23 | Huels Troisdorf | Process for the production of composite safety washers |
| DE102007057577A1 (en) | 2007-11-27 | 2009-05-28 | Mathias Lingott | Method for producing laminated safety glass and laminated safety glass produced by this method |
| DE102007057576A1 (en) | 2007-11-27 | 2009-05-28 | Mathias Lingott | Glass production process for architectural glass uses saccharose and derivatives from collagen and/or pectin compounds as intermediate layer |
| JP6855820B2 (en) * | 2016-02-12 | 2021-04-07 | 東ソー株式会社 | Crosslinked ethylene-vinyl acetate copolymer saponified product, hot melt adhesive resin composition, adhesive and molded article thereof |
| JP2023127000A (en) * | 2020-08-06 | 2023-09-13 | Ａｇｃ株式会社 | Production method of multilayer body, multilayer body, and production method of semiconductor package |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2399653A (en) * | 1945-02-13 | 1946-05-07 | Du Pont | Hydrolyzed polymers |
| US2448946A (en) * | 1944-06-20 | 1948-09-07 | Du Pont | Method for insolubilizing hydrolyzed ethylene vnyl ester polymers |
| US3923757A (en) * | 1971-12-23 | 1975-12-02 | Monsanto Res Corp | Transparent adhesive |
| US4137364A (en) * | 1976-11-05 | 1979-01-30 | Monsanto Research Corporation | Transparent laminate and adhesive film |
| JPH03109241A (en) * | 1989-06-06 | 1991-05-09 | Takeda Chem Ind Ltd | Adhesive plastic middle layer for sandwich glass |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923575A (en) * | 1971-08-09 | 1975-12-02 | William A Wootten | Method of forming a board structure comprising spaced panels joined by intervening tabs |
| JPS57196747A (en) * | 1981-05-29 | 1982-12-02 | Bridgestone Corp | Laminated glass |
| EP0363813B1 (en) * | 1988-10-06 | 1994-02-16 | Showa Denko Kabushiki Kaisha | Terpolymer and transparent laminate having excellent optical properties |
-
1991
- 1991-09-19 JP JP23951491A patent/JP3213979B2/en not_active Expired - Lifetime
-
1992
- 1992-09-17 DE DE4231199A patent/DE4231199C2/en not_active Expired - Lifetime
- 1992-09-18 GB GB9219792A patent/GB2259669B/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2448946A (en) * | 1944-06-20 | 1948-09-07 | Du Pont | Method for insolubilizing hydrolyzed ethylene vnyl ester polymers |
| US2399653A (en) * | 1945-02-13 | 1946-05-07 | Du Pont | Hydrolyzed polymers |
| US3923757A (en) * | 1971-12-23 | 1975-12-02 | Monsanto Res Corp | Transparent adhesive |
| US4137364A (en) * | 1976-11-05 | 1979-01-30 | Monsanto Research Corporation | Transparent laminate and adhesive film |
| JPH03109241A (en) * | 1989-06-06 | 1991-05-09 | Takeda Chem Ind Ltd | Adhesive plastic middle layer for sandwich glass |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0743175A2 (en) * | 1995-05-17 | 1996-11-20 | Bridgestone Corporation | Laminated glass |
| EP0743175A3 (en) * | 1995-05-17 | 1997-09-24 | Bridgestone Corp | Laminated glass |
| US5759698A (en) * | 1995-05-17 | 1998-06-02 | Bridgestone Corporation | Laminated glass |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2259669B (en) | 1995-09-20 |
| DE4231199C2 (en) | 2001-07-12 |
| JPH0578153A (en) | 1993-03-30 |
| DE4231199A1 (en) | 1993-03-25 |
| JP3213979B2 (en) | 2001-10-02 |
| GB9219792D0 (en) | 1992-10-28 |
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| Date | Code | Title | Description |
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| PE20 | Patent expired after termination of 20 years |
Expiry date: 20120917 |