GB1576483A - Creation of Inventions and Patents with Artificial Intelligence

GB1576483A – Adhesives and sealing compositions hardening with the exclusion of oxygen
– Google Patents

GB1576483A – Adhesives and sealing compositions hardening with the exclusion of oxygen
– Google Patents
Adhesives and sealing compositions hardening with the exclusion of oxygen

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Publication number
GB1576483A

GB1576483A
GB8035/77A
GB803577A
GB1576483A
GB 1576483 A
GB1576483 A
GB 1576483A
GB 8035/77 A
GB8035/77 A
GB 8035/77A
GB 803577 A
GB803577 A
GB 803577A
GB 1576483 A
GB1576483 A
GB 1576483A
Authority
GB
United Kingdom
Prior art keywords
adhesive
sealing agent
ester
weight
relative
Prior art date
1976-02-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB8035/77A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel AG and Co KGaA

Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
1976-02-27
Filing date
1977-02-25
Publication date
1980-10-08

1977-02-25
Application filed by Henkel AG and Co KGaA
filed
Critical
Henkel AG and Co KGaA

1980-10-08
Publication of GB1576483A
publication
Critical
patent/GB1576483A/en

Status
Expired
legal-status
Critical
Current

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Classifications

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

C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule

C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups

C—CHEMISTRY; METALLURGY

C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON

C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups

C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups

C08F290/06—Polymers provided for in subclass C08G

C08F290/061—Polyesters; Polycarbonates

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

C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC

Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

Y10T428/00—Stock material or miscellaneous articles

Y10T428/31504—Composite [nonstructural laminate]

Y10T428/31507—Of polycarbonate

Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC

Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

Y10T428/00—Stock material or miscellaneous articles

Y10T428/31504—Composite [nonstructural laminate]

Y10T428/31678—Of metal

Y10T428/31692—Next to addition polymer from unsaturated monomers

Description

PATENT SPECIFICATION ( 11) 1 573 483
f) ( 21) Application No 8035/77 ( 22) Filed 25 Feb 1977 ( 19) ( 31) Convention Application No 2607959 ( 32) Filed 27 Feb 1976 in ( 33) Fed Rep of Germany (DE)
( 44) Complete Specification Published 8 Oct 1980
Un ( 51) INT CL C 09 J 3/00 CO 8 F 20/26 -^ C 09 K 3/10 ( 52) Index at Acceptance C 3 P DI C 3 Y B 230 B 248 B 320 B 324 F 118 F 581 G 230 G 300 ( 54) ADHESIVES AND SEALING COMPOSITIONS HARDENING WITH THE EXCLUSION OF OXYGEN ( 71) We, HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN, a German Company, of 67 Henkelstrasse, 4000 Duesseldorf-Holthausen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: 5
The present invention relates to adhesives or sealing agents hardening with the exclusion of oxygen, comprising mixtures of acrylic or methacrylic acid esters and organic peroxides, particularly hydroperoxides.
It is known that methacrylic acid esters or acrylic acid esters of a wide variety of alcohols together with hydroperoxides constitute mixtures which harden under the exclusion of 10 atmospheric oxygen and which can be processed as adhesives or sealing agents Considerable values of the tensile shearing strength, such as are important in, for example, the securing of shafts, are measured when using (meth) acrylic acid esters of cycloaliphatic alcohols.
Furthermore, an important feature of these so-called anaerobically hardening adhesives is that they result in strong joints between the workpieces even at high temperatures A further 15 requirement is that the glued joints should have satisfactory flexibility Accordingly, adhesives or sealing agents hardening under the exclusion of atmospheric oxygen must have a number of technological properties, some of which are difficult to combine with one another.
By practice of the present invention there may be provided adhesives or sealing agents of this type which harden with the exclusion of atmospheric oxygen, which polymerize at room 20 temperature, i e harden to form a layer of adhesive or a sealing compound and result in a loadable joint after a short period of time, which rapidly and rigidly interconnect non-ferrous material such as aluminium and aluminium alloys, and which have satisfactory thermal stability and flexibility.
According to the present invention there is provided an adhesive or sealing agent which 25 hardens in the absence of oxygen, comprising an organic peroxide and an acrylic or methacrylic acid ester which is a polycarbonate ester wherein the ester groups are terminal (meth) acrylic ester groups.
The polycarbonate ester present in the adhesive or sealing agent of the present invention may be an ester of a polycarbonate having terminal OH groups and an average molecular 30 weight of from 300 to 10,000.
By way of example, suitable polycarbonates having end position hydroxyl groups contain, as the diol component ethylene glycol, propylene glycol-( 1,3), butane diol-( 1,4), hexane diol( 1,6), neopentyl glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,4dimethylolcyclohexane, preferably short-chain diols, such as butane diol or ether diols such 35 as triethylene glycol It has proved to be advantageous to use ao bishydroxypolycarbonates which are composed of a plurality of diols in different mixture ratios, for example triethylene glycol and neopentyl glycol The oa,w -bishydroxypolycarbonates can be produced by conventional methods, for example by condensation of the corresponding diols with diphenylcarbonate or other readily available carbonates 40 The esterification or ester interchange of these a,wbishydroxypolycarbonates with methyl(meth) acrylate in the presence of acid catalysts such as cation exchangers is effected by the azeotropic distilling-off of the methanol being liberated with methyl (meth) acrylate.
The a,wo -di(meth) acrylates of polycarbonates, thus obtained, are liquid substances and are stable when stored in the presence of oxygen at low temperatures 45 2 1,576,483 2 The compounds which are obtainable in the manner described above, and which are designated “polycarbonate-di (meth) acrylic ester” in the present context, can be characterised with reference to physical measuring methods They are colourless or yellow-coloured highly viscous substances.
The adhesives and sealing compounds in accordance with the present invention may 5 contain, relative to the polymerizable components, up to 90 percent by weight of the said polycarbonate di(meth)acrylic esters In accordance with a preferred embodiment, they additionally contain 10 to 40 percent by weight, relative to the total quantity of polymerizable components, of cycloaliphatic or aliphatic (meth)acrylic acid esters having, if required, at least one OH group which is still free Substances which come under consideration for this 10 purpose are monomethacrylates, such as 5,6-dihydrodicyclopentadienyl methacrylate, cyclohexylmethacrylate, ethylhexylmethacrylate, hydroxyethylmethacrylate, hydroxypropylmethacrylate or dimethacrylates such as ethyleneglycoldimethacrylate, triethyleneglycoldimethacrylate, polyethyleneglycoldimethacrylate In accordance with an advantageous embodiment, the adhesives and sealing agents in accordance with the present invention 15 comprise mixtures of 70 to 80 % by weight of so-called di (meth) acrylic esters and 20 to 30 % by weight of monomethacrylates.
In a further embodiment of the present invention, the adhesive or sealing agent comprises, in addition to the organic peroxide and the polycarbonate di (meth) acrylic acid ester, from 10 to 40 % by weight, relative to the total quantity of polymerizable components of tetrahyd 20 rofurfurylmethacrylate.
The adhesive or sealing agent in accordance with the present invention may contain, if required, a minor amount of a further polymerizable unsaturated compound and/or auxiliary substance For example, the properties of a glued joint may be enhanced by addition of a carboxylic acid containing at least one free polymerizable double bond, such as methacrylic 25 acid or acrylic acid, in a quantity of from 0 1 to 5 % by weight of the polymerizable components.
Finally, the adhesives and sealing agents in accordance with the present invention should also contain, in a known manner, peroxides, particularly hydroperoxides such as cumenehydroperoxide or tert-butylhydroperoxide They are generally added in quantities of from 1 to 30 %by weight relative to the polymerizable components Furthermore, when in the made-up form, the adhesives and sealing compounds desirably contain an additive selected from stabilizers, inhibitors and accelerators Suitable inhibitors are quinone or hydroquinone in concentrations of 100 to 100 Oppm, preferably 200 to 500 ppm Suitable accelerators are, for example, imide accelerators such as benzoic acid sulphimide, particularly sulphohydrazide 35 accelerators such as p-toluene sulphonic acid hydrazide, combined with a tert amine, preferably N,N-dimethyl-p toluidine A suitable stabilizer is peracetic acid.
The accelerator and the stabilizer, when used, should be added in ratios which are matched to one another, in order to obtain optimum properties In general, they are used in quantities of from 0 05 to 3 % by weight relative to the polymerizable components 40 If desired, the adhesives or sealing agents can contain additives of softeners, thickening agents such as polymers based on styrene or (meth) acrylic polymers, or dyes and pigments.
The adhesives or sealing agents in accordance with the present invention are produced by mixing the components at room temperature and are stable for periods ranging from months to years when they are stored in vessels permeable to air, such as polyethylene bottles When 45 the adhesives or sealing agents are applied between metal surfaces, they rapidly polymerize to form a rigid joint.
The advantages of the adhesives or sealing agents in accordance with the present invention are as follows:
Increased temperatures are not required for the purpose of hardening, and the parts to be 50 connected to one another are loadable after a short period of time In a addition to ferrous materials, aluminium parts can also be glued with satisfactory strength The glued joint has excellent thermal stability and flexibility The adhesive in accordance with the present invention is particularly suitable for interconnecting metals when high strengths, satisfactory stability and flexibility of the glued joint are required 55 The adhesives and sealing agents in accordance with the present invention can be used for the glueing of sheet metals or metal parts made from various materials, for the securing of bearing shafts and for the sealing of pipe joints and the like.
The present invention will now be further described by way of the following Examples:
The adhesives produced in accordance with the following Examples, and hardening under 60 the exclusion of oxygen, were subjected to the following tests:
In the stability test, a test tube 10 cm in length and 10 mm in width was filled to 9/1 Oths of its capacity with the mixture according to Examples 1 to 6 and was suspended in a bath maintained at 80 C, and the period of time which elapsed until the first gel formation occurred was measured All the samples were free from gel after 60 minutes 65 1,576,483 After hardening for 72 hours at room temperature, the tensile shearing strength in accordance with DIN 52383 was measured on sand-blasted, singly overlapped test bodies made from sheet steel (DIN 1541/ST 1203, 100 x 20 x 1 5 mm) and aluminium sheets (DIN 1783-Al Cu Mg 2 pl 100 x 25 x 1 55 m) (length of overlap 10 mm) on a tensile-testing machine S (advance 20 mm/min) 5 The thermal stability was determined by means of the torsional force moments applied to glued nuts and bolts Bolts (M 10 x 30 DIN 933-8 8) and nuts (M 10 DIN 9345 6) were glued and, after hardening for 3 days at room temperature, were stored for three days in a drying cabinet at 150 C and were subsequently clamped in a vice and the torsional force moment was determined by means of a torsion wrench 10 A three-point bending test was carried out in order to determine the flexibility: singly overlapped ( 2 cm 2) steel sheets (DIN 1541 ST 1405 100 x 20 x 0 8 mm) were glued to one another and, after hardening for 72 hours at room temperature, the centre of the overlap was bent by means of a mandrel ( O 10 mm) until breaks appeared The angle at which the glued joint parted was measured and is indicative of the flexibility of the glued joint 15 All the tests were carried out five times and the mean value of the test results was then determined.
Example 1 g of an a,w bishydroxypolycarbonate, produced from diphenylcarbonate and triethyleneglycol (molecular weight 1400), were ester-interchanged with 60 g of methyl 20 methacrylate in the presence of 15 g of a commercially available acid cation exchanger and 750 mg of hydroquinone by the distilling-off of the methanolmethylmethacrylate azeotrope.
The reaction mixture was then maintained at the boiling temperature of the methacrylic acid methyl ester and the ester was introduced again after the methanol had been separated out.
The dimethacrylic ester of the polycarbonate obtained constitutes a colourless, viscous liquid 25 and is suitable as a base for anaerobically hardening adhesives.
The following substances were mixed with one another in order to produce an adhesive:
g of polycarbonate dimethacrylic ester g of polyethyleneglycolidimethacrylate, mw ‘ 330 1 g of p-toluene sulphonic acid hydrazide 30 0.5 g of N,N-dimethyl-p-toluidine g of 70 % solution of cumene hydroperoxide in cumene 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found when glued joints had been made for test 35 purposes:
Tensile shearing strength on steel: 189 kp/cm 2 Tensile shearing strength on aluminium: 110 kp/cm 2 Thermal stability: 180 kp cm 40 Flexibility according to the bending test: 1200 Example 2 g of an a,wo-bishydroxypolycarbonate, produced from diphenylcarbonate and triethyleneglycol (molecular weight 700), was ester-interchanged with methylmethacrylate in the manner described in Example 1 45 The following substances were mixed with one another to produce an adhesive:
g of polycarbonate dimethacrylic ester g of hydroyethylmethacrylate 1 g of p-toluene sulphonic acid hydrazide 0 5 g of N,N-dimethyl-p-toluidine 50 g of 70 % solution of cumene hydroperoxide in cumene 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found after glued joints had been made for test purposes: 55 Tensile shearing strength on steel: 207 kp/cm 2 Tensile shearing strength on aluminium: 115 kp/cm 2 Thermal stability: 200 kp cm Flexibility according to the bending test: 120 60 Example 3 g of an a,(o-bishydroxypolycarbonate, produced from diphenylcarbonate and a mixture of triethyleneglycol and 1,4-di-methylol -cyclohexane in the ratio 2: 1 by weight molecular weight 800), were ester-interchanged with methylmethacrylate in the same manner as described in Example 1 65 1,576,483 The following substances were mixed in order to produce an adhesive:
g of polycarbonate dimethacrylic ester g of polyethyleneglycol dimethacrylate, mw’ -330 1 g of p-toluene sulphonic acid hydrazide O 5 g of N,N-dimethyl-p-toluidine S g of 70 % solution of cumene hydroperoxide in cumene 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found after making glued joints for test purposes:
Tensile shearing strength on steel: 193 kp/cm 2 10 Tensile shearing strength on aluminium: 105 kp/cm 2 Thermal stability: 220 kp cm Flexibility in accordance with the bending test: 120 Example 4 15 g of an a, o-bishydroxypolycarbonate, produced from diphenylcarbonate and a mixture of triethyleneglycol and neopentyl-glycol in the ratio 1:2 by weight (molecular weight -5000), were esterinterchanged with methylmethacrylate in the same manner as described in Example 1.
The following substances were mixed in order to produce an adhesive: 20 g of polycarbonate dimethacrylic ester g of hydroxyethylmethacrylate 1 g of p-toluene sulphonic acid hydrazide 0.5 g of N,N-dimethyl-p-toluidine 5 g of 70 % solution of cumene hydroperoxide in cumene 25 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found after glued joints had been made for test purposes:
Tensile shearing strength on steel: 187 kp/cm 2 30 Tensile shearing strength on aluminium: 103 kp/cm 2 Thermal stability: 180 kp cm Flexibility according to the bending test: 110 Example 5 35 g of an a,o-bishydroxypolycarbonate, produced from diphenylcarbonate and a mixture of triethyleneglycol and neopentylglycol in the ratio 2: 1 by weight (molecular weight 1000), were ester-interchanged with methylmethacrylate in the manner described in Example 1.
The following substances were mixed with one another in order to the produce the 40 adhesive:
g of polycarbonate dimethacrylate g of polyethyleneglycol dimethacrylate, mw-330 1 g of p-toluene sulphonic acid hydrazide 0 5 g of N,N-dimethyl-p-toluidine 45 g of 70 % solution of cumene hydroperoxide in cumene 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found after glued joints had been made for test purposes: 50 Tensile shearing strength on steel: 227 kp/cm 2 Tensile shearing strength on aluminium: 122 kp/cm 2 Thermal stability: 240 kp cm Flexibility according to the bending test: 110 55 Example 6 g of an a,o-bishydroxypolycarbonate, produced from diphenylcarbonate and triethyleneglycol and neopentylglycol in the ratio 1:1 by weight (molecular weight 7000), were ester-interchanged with methylmethacrylate in the manner described in Example 1.
The following substances were mixed with one another in order to produce the adhesive: 60 g of polycarbonate dimethacrylate g of tetrahydrofurfurylmethacrylate 1 g of p-toluene sulphonic acid hydrazide 0.5 g of N,N-dimethyl-p-toluidine 5 g of 70 % solution of cumene hydroperoxide in cumene 65 1,576,483 5 0.5 g of 40 % solution of peracetic acid in acetic acid 3 g of methacrylic acid The following average values were found after glued joints had been made for test purposes:
tensile shearing strength on steel: 205 kp/cm 2 5 Tensile shearing strength on aluminium: 110 kp/cm 2 Thermal stability: 180 kp cm Flexibility according to the bending test: 120

Claims (1)

WHAT WE CLAIM IS: 10
1 An adhesive or sealing agent which hardens in the absence of oxygen, comprising an organic peroxide and an acrylic or methacrylic acid ester which is a polycarbonate ester wherein the ester groups are terminal (meth) acrylic acid ester groups the ester groups.
2 An adhesive or sealing agent as claimed in claim 1, in which the organic peroxide is present in an amount of from 1 to 10 % by weight relative to the polymerizable constituents 15 3 An adhesive or sealing agent as claimed in claim 1 or claim 2, in which the organic peroxide is an organic hydroperoxide.
4 An adhesive or sealing agent as claimed in any one of claims 1 to 3, in which the polycarbonate ester is an ester of a polycarbonate having terminal OH groups and an average molecular weight of from 300 to 10,000 20 An adhesive or sealing agent as claimed in any one of claims 1 to 4, in which the polycarbonate ester is present in an amount of up to 90 % by weight, relative to the polymerizable constituents.
6 An adhesive or sealing agent as claimed in any one of claims 1 to 5, which also comprises 10 to 40 %by weight, relative to the total quantity of polymerizable constituents, of 25 a cycloaliphatic or aliphatic (meth) acrylic acid ester.
7 An adhesive or sealing agent as claimed in claim 6, in which the cycloaliphatic or aliphatic (meth)acrylic acid ester contains at least one free OH group.
8 An adhesive or sealing agent as claimed in any one of claims 1 to 5, which also comprises 10 to 40 % by weight, relative to the total quantity of polymerizable components, of 30 tetrahydrofurfurylmethacrylate.
9 An adhesive or sealing agent as claimed in any one of claims 1 to 8, which further comprises a minor amount of a further polymerizable unsaturated compound and/ or auxiliary substance.
10 An adhesive or sealing agent as claimed in claim 9, which comprises from O 1 to 5 % 35 by weight, relative to the polymerizable constituents, of a carboxylic acid containing at least one free polymerisable double bond.
11 An adhesive or sealing agent as claimed in claim 10, in which the carboxylic acid is acrylic or methacrylic acid.
12 An adhesive or sealing agent as claimed in any one of claims 9 to 11, which comprises 40 an additive selected from stabilizers, inhibitors, and accelerators.
13 An adhesive or sealing agent as claimed in claim 12 in which the stabilizer is peracetic acid.
14 An adhesive or sealing agent as claimed in claih 62 or claim 13, in which the accelerators or stabilizers are used in an amount of 0 05 to 3 % by weight, relative to the 45 polymerizable constituents.
An adhesive or sealing agent substantially as hereinbefore described and with reference to any one of the examples.
W.P THOMPSON & CO.
Chartered Patent Agents, 50 Coopers Building, Church Street, Liverpool L 1 3 AB Printed tor Her Malcst? Stationery Office hb Croydon Printing Company Lmnitecd Croydon Surrey 1980.
Publi hed hx hec Patent Olflc 25 Sourthampton Btldtiings London WC 2 A l AY,from xahich copic, may hbe obtained

GB8035/77A
1976-02-27
1977-02-25
Adhesives and sealing compositions hardening with the exclusion of oxygen

Expired

GB1576483A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

DE19762607959

DE2607959A1
(en)

1976-02-27
1976-02-27

ADHESIVES AND SEALING COMPOUNDS THAT CONSTITUTE WITH OXYGEN

Publications (1)

Publication Number
Publication Date

GB1576483A
true

GB1576483A
(en)

1980-10-08

Family
ID=5970997
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB8035/77A
Expired

GB1576483A
(en)

1976-02-27
1977-02-25
Adhesives and sealing compositions hardening with the exclusion of oxygen

Country Status (11)

Country
Link

US
(1)

US4107386A
(en)

JP
(1)

JPS52104553A
(en)

AT
(1)

AT353381B
(en)

BE
(1)

BE851827A
(en)

CH
(1)

CH628084A5
(en)

DE
(1)

DE2607959A1
(en)

FR
(1)

FR2342327A1
(en)

GB
(1)

GB1576483A
(en)

IT
(1)

IT1075120B
(en)

NL
(1)

NL7701101A
(en)

SE
(1)

SE7701139L
(en)

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FR2431514A1
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1978-07-19
1980-02-15
Poudres & Explosifs Ste Nale

NOVEL UNSATURATED POLY (CARBONATES-URETHANNES) AND THEIR APPLICATIONS TO PHOTORETICULATION

DE2843154A1
(en)

1978-10-04
1980-04-17
Bayer Ag

GRAFT POLYCARBONATES, THEIR PRODUCTION AND THEIR USE AS MOLDED PARTS

WO1981000852A1
(en)

1979-09-28
1981-04-02
N Gavryushenko
Method of binding conjugated surfaces

US4539358A
(en)

1980-03-20
1985-09-03
General Electric Company
Polycarbonate compositions

US4319003A
(en)

1980-09-26
1982-03-09
General Motors Corporation
Poly(methyl methacrylate) polycarbonate block copolymers

DE3175474D1
(en)

1981-08-10
1986-11-20
Gen Electric
Polycarbonate compositions

IT1151544B
(en)

1982-04-15
1986-12-24
Anic Spa

COMPOSITION BASED ON ALIPHATIC POLYCARBONATES CONTAINING URETHANE GROUPS AND ACRYLIC OR METHACRYLIC TERMINATIONS CROSS-LINKED IN THE PRESENCE OF ROOTIC INITIATORS

IT1151545B
(en)

1982-04-15
1986-12-24
Anic Spa

COMPOSITION BASED ON ALIPHATIC POLYCARBONATES WITH ACRYLIC OR METACRYLIC TERMINATIONS RETICULABLE IN THE PRESENCE OF ROOTIC INITIATORS

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1985-03-29
1994-01-04
Jeneric/Pentron, Inc.
Dental resin materials

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1985-06-19
1988-11-08
Nippon Kayaku Kabushiki Kaisha
Di-(meth)acrylic acid ester, resin composition comprising the same and coating agent comprising the same

CH671770A5
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1986-11-06
1989-09-29
Gdf Ges Dentale Forsch

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1986-11-06
1990-03-30
Schuetz Dental Gmbh

JP2586025B2
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1987-02-12
1997-02-26
三菱瓦斯化学株式会社

Graft polycarbonate resin composition.

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1996-11-27
1999-10-12
Ppg Industries Ohio, Inc.
Optical resin composition from polyol((meth)acryloyl carbonate) monomer

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2000-04-18
2001-11-02
Sumitomo Chem Co Ltd
Method for preserving photosensitive composition

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2001-01-03
2004-07-27
Sika Ag, Vorm. Kaspar Winkler & Co.
Adhesives with good mechanical properties, suitable for use with antennas

JP2007262244A
(en)

2006-03-28
2007-10-11
Sumitomo Bakelite Co Ltd
Resin composition and semiconductor device manufactured using the same

AU2012319183A1
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2011-10-03
2014-05-22
Biomimedica, Inc.
Polymeric adhesive for anchoring compliant materials to another surface

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Assignee
Title

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(en)

1968-07-15
1972-01-25
Bayer Ag
Polyurethanes process and product prepared from aliphatic polycarbonates containing in situ polymerized unsaturated compounds

US4045514A
(en)

1972-11-18
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Sumitomo Chemical Company, Limited
Thermoplastic resin composition comprising methyl methacrylate resins and a polycarbonate

JPS5228150B2
(en)

1973-01-19
1977-07-25

1976

1976-02-27
DE
DE19762607959
patent/DE2607959A1/en
not_active
Withdrawn

1977

1977-02-02
SE
SE7701139A
patent/SE7701139L/en
not_active
Application Discontinuation

1977-02-02
NL
NL7701101A
patent/NL7701101A/en
not_active
Application Discontinuation

1977-02-22
US
US05/770,386
patent/US4107386A/en
not_active
Expired – Lifetime

1977-02-22
IT
IT20548/77A
patent/IT1075120B/en
active

1977-02-24
JP
JP1875877A
patent/JPS52104553A/en
active
Pending

1977-02-25
AT
AT127777A
patent/AT353381B/en
not_active
IP Right Cessation

1977-02-25
BE
BE175257A
patent/BE851827A/xx
not_active
IP Right Cessation

1977-02-25
CH
CH240277A
patent/CH628084A5/en
not_active
IP Right Cessation

1977-02-25
GB
GB8035/77A
patent/GB1576483A/en
not_active
Expired

1977-02-25
FR
FR7705506A
patent/FR2342327A1/en
active
Granted

Also Published As

Publication number
Publication date

FR2342327B1
(en)

1980-03-28

ATA127777A
(en)

1979-04-15

FR2342327A1
(en)

1977-09-23

SE7701139L
(en)

1977-08-28

CH628084A5
(en)

1982-02-15

BE851827A
(en)

1977-08-25

IT1075120B
(en)

1985-04-22

NL7701101A
(en)

1977-08-30

DE2607959A1
(en)

1977-09-01

AT353381B
(en)

1979-11-12

JPS52104553A
(en)

1977-09-02

US4107386A
(en)

1978-08-15

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