DK2285773T3 - Hærdningsaccelerator til anaerobisk hærdbare sammensætninger - Google Patents
Hærdningsaccelerator til anaerobisk hærdbare sammensætninger Download PDFInfo
- Publication number
- DK2285773T3 DK2285773T3 DK09743430.2T DK09743430T DK2285773T3 DK 2285773 T3 DK2285773 T3 DK 2285773T3 DK 09743430 T DK09743430 T DK 09743430T DK 2285773 T3 DK2285773 T3 DK 2285773T3
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- DK
- Denmark
- Prior art keywords
- group
- formula
- compound
- alkylene
- alkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 140
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000007795 chemical reaction product Substances 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- -1 heterocyclylene Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000002947 alkylene group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 239000000376 reactant Substances 0.000 claims description 17
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
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- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 230000001939 inductive effect Effects 0.000 claims description 10
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000004001 thioalkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 4
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- 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
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- 238000002360 preparation method Methods 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
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- 239000003112 inhibitor Substances 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- GYHPTPQZVBYHLC-UHFFFAOYSA-N 2-[2-[2-[2-(2-ethylhexanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOCCOC(=O)C(CC)CCCC GYHPTPQZVBYHLC-UHFFFAOYSA-N 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
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- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
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- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 238000002076 thermal analysis method Methods 0.000 description 1
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- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Forbindelse der valgt fra gruppen af forbindelser, som er repræsenteret ved strukturformel (I): Formel I
hvor i formel I: R1 er valgt fra gruppen, der består af aryl og heteroaryl; X er valgt fra gruppen, der består af -O-, -S-, -NH-, alkylen, cycloalkylen, heterocyclylen, arylen, alkarylen og heteroarylen; Y er en substitueret alkylengruppe, der omfatter et alkylen-skelet med mindst to sammenhængende carbonatomer og som eventuelt kan være afbrudt af en eller flere -O-, -S- eller -NH-molekyldele, forudsat at hver -O-, -S- eller -NH-molekyldel af Y, hvis den er til stede, ikke støder op til en -O-, -S- eller -NH- af X, hvor alkylengruppen af Y har substituenter, der uafhængigt er valgt fra gruppen, som består af -OH, -NH2, -SH, cycloalkyl, heterocyclyl, aryl og heteroaryl, eller to hydrogenatomer på det samme carbonatom af Y er erstattet af carbonyl, og hvor mindst to substituenter af Y uafhængigt er valgt fra gruppen, der består af -OH, -NH2, og -SH, og forudsat at hver af -OH, -NH2, eller -SH-grupperne ikke er knyttet til det samme carbonatom af Y eller en -O-, -S- eller -NH-skelet-molekyldel af Y.
2. Forbindelsen ifølge krav 1, hvor X er -O-.
3. Forbindelsen ifølge krav 1, hvor Y omfatter to -OH-substituenter.
4. Forbindelsen ifølge krav 1, hvor forbindelsen er repræsenteret af strukturformel (A), Formel (A)
eller strukturformel (B):
5. Sammensætning der omfatter forbindelsen ifølge krav 1.
6. Sammensætningen ifølge krav 5, hvilken sammensætning er en anaerob hærdbar sammensætning, der omfatter en (meth)acrylat-komponent og en anaerob hærdningsinducerende sammensætning, som omfatter forbindelsen ifølge krav 1.
7. Sammensætningen ifølge krav 6, hvor (meth)acrylat-komponenten er valgt blandt (meth)acrylatmonomerer, der er repræsenteret af FI2C=CGC02R8, hvor G er hydrogen, halogen eller alkylgrupper, der har fra 1 til ca. 4 carbonatomer, og R8 er valgt fra alkyl-, cycloalkyl-, alkenyl-, cycloalkenyl-, alkaryl-, aralkyl- eller arylgrupper, der har fra 1 til ca. 16 carbonatomer, hvoraf nogen eventuelt kan være substitueret eller afbrudt.
8. Sammensætningen ifølge krav 5, hvor (meth)acrylat-komponenten omfatter fra 10 til 90 vægt-% af sammensætningen.
9. Hærdbar sammensætning ifølge krav 6, hvor den anaerobe hærdningsinducerende sammensætning er i det væsentlige fri for acetylphenylhydrazin (APH).
10. Reaktionsprodukt der er fremstillet ud fra reaktanter, som omfatter: a) mindst en forbindelse der er valgt fra gruppen af forbindelser, som er
hvor i formel II: R1 er valgt fra gruppen, der består af aryl og heteroaryl; og repræsenteret ved Formel (il) strukturformel (II) b) mindst en forbindelse der er valgt fra gruppen af forbindelser, som er repræsenteret ved strukturformel (III) og strukturformel (IV): Formel (III)
hvor i formel III: X er valgt fra gruppen, der består af -O-, -S-, -NH-, alkylen, cycloalkylen, heterocyclylen, arylen, alkarylen og heteroarylen; Y er en substitueret alkylengruppe, der omfatter et alkylen-skelet, som har mindst to sammenhængende carbonatomer og som eventuelt kan være afbrudt af en eller flere -O-, -S- eller -NH-molekyldele, forudsat at hver af -O-, -S - eller -NH-molekyldelene af Y, hvis den er til stede, ikke støder op til en -O-, -S- eller -NH- af X, hvor alkylengruppen af Y har substituenter, der uafhængigt er valgt fra gruppen som består af-OH, -NH2, -SH, cycloalkyl, heterocyclyl, aryl og heteroaryl, eller to hydrogenatomer på det samme carbonatom af Y er erstattet af carbonyl, og hvor mindst to substituenter af Y uafhængigt er valgt fra gruppen, der består af -OH, -NH2, og -SH, og forudsat at hver af -OH, -NH2, eller -SH-grupperne ikke er bundet til det samme carbonatom af Y eller en -O-, -S- eller -NH-skelet-molekyldel af Y; og R2 er valgt fra gruppen, der består af -OR, NHR, alkyl og arylalkyl, hvor R er H, alkyl eller arylalkyl; og Formel (IV)
hvor i formel IV: Z og Z' hver uafhængigt er valgt fra gruppen, der består af -O-, -S- og -N(R3)-, hvor R3 er H eller alkyl; m er mindst 1; hver R4 er uafhængigt valgt fra gruppen, der består af hydroxyalkyl, aminoalkyl, thioalkyl, hydroxylsubstitueret cycloalkyl, arylalkyl som har mindst en -OH, -NH2, eller -SH-gruppe, og heteroarylalkyl der har mindst en -OH, -NH2, eller -SH-gruppe, forudsat at der ikke er mere end en R4-substituent bundet til et substituerbart ringcarbonatom; og p er 1 eller 2.
11. Reaktionsproduktet ifølge krav 10, hvor X er -O-.
12. Reaktionsproduktet ifølge krav 10, hvor Y omfatter to -OH-substituenter.
13. Fremgangsmåde til fremstilling af en forbindelse der er valgt fra gruppen af forbindelser, som er repræsenteret ved strukturformel (I): Formel (I)
hvor i formel I: R1 er valgt fra gruppen, der består af aryl og heteroaryl; X er valgt fra gruppen, der består af -O-, -S-, -NH-, alkylen, cycloalkylen, heterocyclylen, arylen, alkarylen og heteroarylen; Y er en substitueret alkylengruppe, der omfatter et alkylen-skelet som har med mindst to sammenhængende carbonatomer, der eventuelt kan være afbrudt af en -O-, -S- eller -NH-molekyldel, forudsat at -O-, -S- eller -NH- af Y, hvis den er til stede, ikke støder op til en anden -O-, -S- eller -NH-gruppe af X, hvor alkylengruppen har substituenter som uafhængigt er valgt fra gruppen, der består af -OH, -NH2, -SH, cycloalkyl, heterocyclyl, aryl og heteroaryl, eller to hydrogenatomer på det samme carbonatom af Y er erstattet af carbonyl, og hvor mindst to substituenter hver uafhængigt er valgt fra gruppen, der består af -OH, -NH2, og -SH, og forudsat at hver af -OH, -NH2, eller -SH ikke er bundet til det samme carbonatom af Y eller en -O-, -S- eller -NH-skelet-molekyldel afY, hvilken fremgangsmåde omfatter trinnet at reagere: (a) mindst en forbindelse der er valgt fra gruppen af forbindelser, som er repræsenteret ved strukturformel (II): Formel (II)
hvor i formel II: R1 er valgt fra gruppen, der består af aryl og heteroaryl; med (b) mindst en forbindelse der er valgt fra gruppen af forbindelser, som er repræsenteret ved strukturformel (III) og Formel (III) strukturformel (IV):
hvor i formel III: X er valgt fra gruppen, der består af -O-, -S-, -NH-, alkylen, cycloalkylen, heterocyclylen, arylen, alkarylen og heteroarylen; Y er en substitueret alkylengruppe, der omfatter et alkylen-skelet som har mindst to sammenhængende carbonatomer, der eventuelt kan være afbrudt af -O-, -S- eller -NH-molekyldele, forudsat at -O-, -S- eller -NH- af Y, hvis den er til stede, ikke støder op til en anden -O-, -S- eller -NH-gruppe af X, hvor alkylengruppen har substituenter, som uafhængigt er valgt fra gruppen, der består af -OH, -NH2, -SH, cycloalkyl, heterocyclyl, aryl og heteroaryl, eller to hydrogenatomer på det samme carbonatom af Y er erstattet af carbonyl, og hvor mindst to substituenter hver uafhængigt er valgt fra gruppen, der består af -OH, -NH2, og -SH, og forudsat at hver af -OH, -NH2, eller -SH ikke er bundet til det samme carbonatom af Y eller en -O-, -S- eller -NH-skelet-molekyldel af Y; og R2 er valgt fra gruppen, der består af -OR, NHR, alkyl og arylalkyl, hvor R er H, alkyl eller arylalkyl; og Formel (IV)
hvor i formel IV: Z og Z' hver er uafhængigt valgt fra gruppen, der består af -O-, -S- og -N(R3)-, hvor R3 er H eller alkyl; m er mindst 1; hver R4 er uafhængigt valgt fra gruppen, der består af hydroxyalkyl, aminoalkyl, thioalkyl, hydroxylsubstitueret cycloalkyl, arylalkyl som har mindst en -OH, -NH2, eller -SH-gruppe, og heteroarylalkyl der har mindst en -OH, -NH2, eller -SH-gruppe, forudsat at der ikke er mere end en R4-substituent bundet til et substituerbart ringcarbonatom; og p er 1 eller 2.
14. Anvendelse af en forbindelse ifølge krav 1 som en hærdningsaccelerator til anaerobe sammensætninger.
15. Anvendelse af et reaktionsprodukt ifølge krav 10 som en hærdningsaccelerator til anaerobe sammensætninger.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/116,500 US8609881B2 (en) | 2008-05-07 | 2008-05-07 | Cure accelerators for anaerobic curable compositions |
| PCT/US2009/042793 WO2009137444A2 (en) | 2008-05-07 | 2009-05-05 | Cure accelerators for anaerobic curable compositions |
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| DK2285773T3 true DK2285773T3 (da) | 2018-03-05 |
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| DK09743430.2T DK2285773T3 (da) | 2008-05-07 | 2009-05-05 | Hærdningsaccelerator til anaerobisk hærdbare sammensætninger |
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| Country | Link |
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| US (1) | US8609881B2 (da) |
| EP (1) | EP2285773B1 (da) |
| JP (1) | JP5691041B2 (da) |
| KR (1) | KR101572706B1 (da) |
| CN (1) | CN102119149A (da) |
| DK (1) | DK2285773T3 (da) |
| NO (1) | NO2285773T3 (da) |
| WO (1) | WO2009137444A2 (da) |
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| US8106141B2 (en) * | 2008-05-07 | 2012-01-31 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| GB2482531B (en) | 2010-08-05 | 2013-11-13 | Loctite R & D Ltd | Adhesive composition with enhanced cure through volume |
| US9365750B2 (en) | 2012-06-27 | 2016-06-14 | Henkel IP & Holding GmbH | Accelerators for curable compositions |
| US9371473B2 (en) | 2012-06-27 | 2016-06-21 | Henkel IP & Holding GmbH | Accelerators for two step adhesive systems |
| WO2015168576A1 (en) * | 2014-05-01 | 2015-11-05 | Henkel IP & Holding GmbH | Anaerobic curable compositions containing blocked dicarboxylic acid compounds |
| WO2015168582A1 (en) | 2014-05-01 | 2015-11-05 | Henkel IP & Holding GmbH | Anaerobic curable compositions containing blocked carboxylic acid compounds |
| WO2016064543A1 (en) * | 2014-10-22 | 2016-04-28 | Henkel IP & Holding GmbH | Phenylhydrazine/anhydride adducts and anaerobic curable compositions using same |
| EP3418053B1 (en) * | 2016-02-19 | 2020-04-22 | Riken Technos Corporation | Decorative sheet |
| WO2017166188A1 (en) * | 2016-03-31 | 2017-10-05 | Henkel Ag & Co. Kgaa | A latent curing accelerator composition and a one-part curable adhesive composition comprising the same |
| CN114667304A (zh) * | 2019-11-18 | 2022-06-24 | 汉高股份有限及两合公司 | 单组分(1k)可厌氧固化组合物 |
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| US3000929A (en) * | 1959-12-15 | 1961-09-19 | Shive William | O-(3-phenylcarbazyl) serine |
| US3218305A (en) | 1963-12-26 | 1965-11-16 | Loctite Corp | Accelerated anaerobic compositions and method of using same |
| DE1719144C3 (de) | 1967-12-01 | 1974-08-22 | Henkel & Cie Gmbh, 4000 Duesseldorf | Unter Sauerstoffausschluß beschleunigt erhärtende Klebstoffe oder Dichtungsmittel |
| DE1817989C3 (de) | 1967-12-28 | 1981-11-05 | Loctite Corp., 06111 Newington, Conn. | Verfahren zum Verbinden von nicht porösen Oberflächen mittels polymerisierbaren Klebstoffen |
| US3970505A (en) | 1973-01-15 | 1976-07-20 | Loctite Corporation | Anaerobic compositions and surface activator therefor |
| US4321349A (en) | 1975-05-23 | 1982-03-23 | Loctite Corporation | Accelerator for curable compositions |
| US4287330A (en) | 1975-05-23 | 1981-09-01 | Loctite Corporation | Accelerator for curable compositions |
| IE43811B1 (en) | 1976-11-08 | 1981-06-03 | Loctite Ltd | Curable acrylate ester compositions containing hydrazine acelerators and acid co-accelerators |
| JPS53102989A (en) | 1977-02-22 | 1978-09-07 | Denki Kagaku Kogyo Kk | Curable composition |
| JPS5710142A (en) * | 1980-06-20 | 1982-01-19 | Fuji Photo Film Co Ltd | Photographic element for color diffusion transfer |
| JPS57122066A (en) * | 1980-12-10 | 1982-07-29 | Ciba Geigy Ag | Manufacture of pyrazolidine-3-one |
| JPS615248A (ja) * | 1984-06-19 | 1986-01-11 | Fuji Photo Film Co Ltd | カラ−拡散転写法用写真フイルムユニツト |
| JPS61188535A (ja) * | 1985-02-18 | 1986-08-22 | Fuji Photo Film Co Ltd | 乾式画像記録方法 |
| IT1230058B (it) * | 1989-04-13 | 1991-09-27 | Ciba Geigy Spa | Procedimento per la preparazione della fenilidrazide dell'acido 2,2.bis(idrossimetil) propionico. |
| JPH0415642A (ja) * | 1990-05-09 | 1992-01-21 | Mitsubishi Paper Mills Ltd | 画像形成方法 |
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| US5605999A (en) | 1995-06-05 | 1997-02-25 | Loctite Corporation | Anaerobically curable silicones |
| JPH09160156A (ja) * | 1995-12-13 | 1997-06-20 | Mitsubishi Paper Mills Ltd | ハロゲン化銀写真感光材料 |
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| WO2000040664A1 (en) | 1999-01-08 | 2000-07-13 | Loctite (R & D) Limited | Novel curative for anaerobic adhesive compositions |
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| US6958368B1 (en) | 2002-05-31 | 2005-10-25 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| JP2004277369A (ja) | 2003-03-18 | 2004-10-07 | Sumitomo Chem Co Ltd | 酸ヒドラジド化合物の製造方法 |
| US6897277B1 (en) | 2003-12-22 | 2005-05-24 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
-
2008
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2009
- 2009-05-05 CN CN200980124434XA patent/CN102119149A/zh active Pending
- 2009-05-05 KR KR1020107027382A patent/KR101572706B1/ko not_active Expired - Fee Related
- 2009-05-05 WO PCT/US2009/042793 patent/WO2009137444A2/en not_active Ceased
- 2009-05-05 NO NO09743430A patent/NO2285773T3/no unknown
- 2009-05-05 EP EP09743430.2A patent/EP2285773B1/en not_active Not-in-force
- 2009-05-05 DK DK09743430.2T patent/DK2285773T3/da active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2285773A2 (en) | 2011-02-23 |
| WO2009137444A3 (en) | 2010-03-04 |
| EP2285773A4 (en) | 2015-01-14 |
| NO2285773T3 (da) | 2018-05-19 |
| EP2285773B1 (en) | 2017-12-20 |
| US20090281335A1 (en) | 2009-11-12 |
| KR101572706B1 (ko) | 2015-11-27 |
| KR20110021850A (ko) | 2011-03-04 |
| CN102119149A (zh) | 2011-07-06 |
| JP2011519944A (ja) | 2011-07-14 |
| JP5691041B2 (ja) | 2015-04-01 |
| US8609881B2 (en) | 2013-12-17 |
| WO2009137444A2 (en) | 2009-11-12 |
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