CN1019572B - 二苯甲酮衍生物的制备方法 - Google Patents
二苯甲酮衍生物的制备方法Info
- Publication number
- CN1019572B CN1019572B CN88100768A CN88100768A CN1019572B CN 1019572 B CN1019572 B CN 1019572B CN 88100768 A CN88100768 A CN 88100768A CN 88100768 A CN88100768 A CN 88100768A CN 1019572 B CN1019572 B CN 1019572B
- Authority
- CN
- China
- Prior art keywords
- group
- compound
- formula
- hydroxyl
- represent
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title description 3
- 150000008366 benzophenones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 alkali metal salt Chemical class 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 3
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000005660 chlorination reaction Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- 230000009965 odorless effect Effects 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- 239000002932 luster Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 11
- 230000008033 biological extinction Effects 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000004922 lacquer Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 229960004756 ethanol Drugs 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- MQVMJSWYKLYFIG-UHFFFAOYSA-N propane-1-sulfonic acid;sodium Chemical compound [Na].CCCS(O)(=O)=O MQVMJSWYKLYFIG-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 1
- MIEJPWILCQAQKT-UHFFFAOYSA-N 4-methylsulfanylbenzoyl chloride Chemical compound CSC1=CC=C(C(Cl)=O)C=C1 MIEJPWILCQAQKT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- 230000005461 Bremsstrahlung Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- PXFOBPPTJQWHRN-UHFFFAOYSA-N [4-(chloromethyl)phenyl]-phenylmethanone Chemical compound C1=CC(CCl)=CC=C1C(=O)C1=CC=CC=C1 PXFOBPPTJQWHRN-UHFFFAOYSA-N 0.000 description 1
- JNMOJOGOZNDAHL-UHFFFAOYSA-N [Na].[Na].OC(CS(=O)(=O)O)C Chemical compound [Na].[Na].OC(CS(=O)(=O)O)C JNMOJOGOZNDAHL-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- FLNKWZNWHZDGRT-UHFFFAOYSA-N azane;dihydrochloride Chemical compound [NH4+].[NH4+].[Cl-].[Cl-] FLNKWZNWHZDGRT-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
- C07C49/786—Benzophenone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8703606 | 1987-02-17 | ||
| GB878703606A GB8703606D0 (en) | 1987-02-17 | 1987-02-17 | Benzophenone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN88100768A CN88100768A (zh) | 1988-09-07 |
| CN1019572B true CN1019572B (zh) | 1992-12-23 |
Family
ID=10612422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88100768A Expired CN1019572B (zh) | 1987-02-17 | 1988-02-15 | 二苯甲酮衍生物的制备方法 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0279475B1 (enExample) |
| JP (1) | JPS63239253A (enExample) |
| KR (1) | KR880009894A (enExample) |
| CN (1) | CN1019572B (enExample) |
| AT (1) | ATE71613T1 (enExample) |
| AU (1) | AU596888B2 (enExample) |
| BR (1) | BR8800614A (enExample) |
| DE (1) | DE3867649D1 (enExample) |
| DK (1) | DK79788A (enExample) |
| GB (1) | GB8703606D0 (enExample) |
| HU (1) | HU205061B (enExample) |
| IL (1) | IL85435A (enExample) |
| IN (1) | IN172591B (enExample) |
| NZ (1) | NZ223526A (enExample) |
| PT (1) | PT86770B (enExample) |
| ZA (1) | ZA881063B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101270060B (zh) * | 2008-05-07 | 2011-02-02 | 重庆医科大学 | 2，6-二（氨基苯亚甲基）环烷酮类化合物及其制备方法和用途 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8806527D0 (en) * | 1988-03-18 | 1988-04-20 | Ward Blenkinsop & Co Ltd | Benzophenone derivatives |
| WO1991007380A1 (en) * | 1989-11-08 | 1991-05-30 | Dunlena Pty. Ltd. | Arthropodicides |
| US5415976A (en) * | 1991-10-25 | 1995-05-16 | Minnesota Mining And Manufacturing Company | Aminoketone sensitizers for photopolymer compositions |
| US5455143A (en) * | 1991-10-25 | 1995-10-03 | Minnesota Mining And Manufacturing Company | Aminoketone sensitizers for aqueous soluble photopolymer compositions |
| AT401726B (de) * | 1993-05-17 | 1996-11-25 | Gerhard Dr Ecker | O-acylaryloxypropanolamine mit tertiärem oder quartärem stickstoff als reversionsmodulatoren für p-glykoprotein mediierte multidrug-resistenz |
| WO2002100912A1 (en) | 2001-06-08 | 2002-12-19 | Basf Aktiengesellschaft | Water soluble radiation activatable polymer resins |
| EP1504772A1 (en) | 2003-08-06 | 2005-02-09 | The Procter & Gamble Company | Superabsorbent polymers having radiation activable surface cross-linkers and method of making them |
| US8080705B2 (en) | 2004-07-28 | 2011-12-20 | The Procter & Gamble Company | Superabsorbent polymers comprising direct covalent bonds between polymer chain segments and method of making them |
| EP1624002B1 (en) | 2004-08-07 | 2019-04-03 | The Procter & Gamble Company | Superabsorbent polymer particles comprising functionalizers and method of making them |
| EP1669394A1 (en) | 2004-12-10 | 2006-06-14 | The Procter & Gamble Company | Superabsorbent polymer particles with improved surface cross-linking and hydrophilicity and method of making them |
| CA2649299A1 (en) | 2006-04-10 | 2007-10-25 | The Procter & Gamble Company | An absorbent member comprising a modified water absorbent resin |
| WO2008102322A2 (en) | 2007-02-22 | 2008-08-28 | The Procter & Gamble Company | Method of surface treating particulate material using electromagnetic radiation |
| EP2459519B1 (en) * | 2009-07-30 | 2017-11-29 | Basf Se | Macrophotoinitiators |
| CN102206293B (zh) * | 2010-03-29 | 2013-09-18 | 比亚迪股份有限公司 | 一种光引发剂,一种光固化涂料和模内装饰方法 |
| JP5565588B2 (ja) * | 2011-03-22 | 2014-08-06 | スリーボンドファインケミカル株式会社 | 液晶滴下工法用シール剤 |
| GB201218447D0 (en) * | 2012-10-15 | 2012-11-28 | Givaudan Sa | Organic compounds |
| AU2013359919A1 (en) | 2012-12-11 | 2015-07-02 | Nano Safe Coatings Incorporated (A Florida Corporation 3 P14000024914) | UV cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
| CN105121495A (zh) | 2013-02-15 | 2015-12-02 | 英派尔科技开发有限公司 | 酚类环氧化合物 |
| MX2015010720A (es) | 2013-02-19 | 2016-07-11 | Nano Safe Coating Inc A Florida Corp 3P 14000024914 | Recubrimiento antimicrobiano de fosforo funcional para superficies de metal. |
| KR101806862B1 (ko) | 2013-06-13 | 2017-12-08 | 엠파이어 테크놀로지 디벨롭먼트 엘엘씨 | 다작용 페놀 수지 |
| WO2015084304A1 (en) * | 2013-12-02 | 2015-06-11 | Empire Technology Development Llc | Novel gemini surfactants and their use |
| CN112441953A (zh) * | 2020-11-22 | 2021-03-05 | 同济大学 | 含二苯硫醚基酮甲酸酯水溶性光聚合引发剂及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1187703B (it) * | 1985-07-23 | 1987-12-23 | Lamberti Fratelli Spa | Benzofenoni sostituiti e loro miscele liquide,atti all'impiego come iniziatori di fotopolimerizzazione |
-
1987
- 1987-02-17 GB GB878703606A patent/GB8703606D0/en active Pending
-
1988
- 1988-02-08 EP EP88200105A patent/EP0279475B1/en not_active Expired - Lifetime
- 1988-02-08 DE DE8888200105T patent/DE3867649D1/de not_active Expired - Fee Related
- 1988-02-08 AT AT88200105T patent/ATE71613T1/de not_active IP Right Cessation
- 1988-02-12 BR BR8800614A patent/BR8800614A/pt unknown
- 1988-02-15 CN CN88100768A patent/CN1019572B/zh not_active Expired
- 1988-02-15 KR KR1019880001593A patent/KR880009894A/ko not_active Withdrawn
- 1988-02-16 DK DK079788A patent/DK79788A/da not_active Application Discontinuation
- 1988-02-16 IN IN125DE1988 patent/IN172591B/en unknown
- 1988-02-16 IL IL85435A patent/IL85435A/xx unknown
- 1988-02-16 HU HU88745A patent/HU205061B/hu not_active IP Right Cessation
- 1988-02-16 JP JP63032003A patent/JPS63239253A/ja active Pending
- 1988-02-16 AU AU11747/88A patent/AU596888B2/en not_active Ceased
- 1988-02-16 ZA ZA881063A patent/ZA881063B/xx unknown
- 1988-02-16 NZ NZ223526A patent/NZ223526A/xx unknown
- 1988-02-17 PT PT86770A patent/PT86770B/pt not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101270060B (zh) * | 2008-05-07 | 2011-02-02 | 重庆医科大学 | 2，6-二（氨基苯亚甲基）环烷酮类化合物及其制备方法和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU205061B (en) | 1992-03-30 |
| EP0279475A3 (en) | 1989-05-31 |
| NZ223526A (en) | 1989-12-21 |
| DK79788D0 (da) | 1988-02-16 |
| BR8800614A (pt) | 1988-09-27 |
| JPS63239253A (ja) | 1988-10-05 |
| HUT47069A (en) | 1989-01-30 |
| EP0279475B1 (en) | 1992-01-15 |
| GB8703606D0 (en) | 1987-03-25 |
| IL85435A (en) | 1992-01-15 |
| AU1174788A (en) | 1988-10-20 |
| AU596888B2 (en) | 1990-05-17 |
| EP0279475A2 (en) | 1988-08-24 |
| ZA881063B (en) | 1988-08-11 |
| IL85435A0 (en) | 1988-07-31 |
| IN172591B (enExample) | 1993-10-23 |
| CN88100768A (zh) | 1988-09-07 |
| ATE71613T1 (de) | 1992-02-15 |
| PT86770A (pt) | 1988-03-01 |
| DE3867649D1 (de) | 1992-02-27 |
| DK79788A (da) | 1988-08-18 |
| KR880009894A (ko) | 1988-10-05 |
| PT86770B (pt) | 1992-05-29 |
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