JP5522580B2 - 新規方法 - Google Patents
新規方法 Download PDFInfo
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- JP5522580B2 JP5522580B2 JP2011537988A JP2011537988A JP5522580B2 JP 5522580 B2 JP5522580 B2 JP 5522580B2 JP 2011537988 A JP2011537988 A JP 2011537988A JP 2011537988 A JP2011537988 A JP 2011537988A JP 5522580 B2 JP5522580 B2 JP 5522580B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzalmalonate
- organopolysiloxane
- functionalized
- unit
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 23
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 45
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 claims abstract description 38
- -1 cyclic ester Chemical class 0.000 claims abstract description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- 229940100498 polysilicone-15 Drugs 0.000 claims description 8
- 229920002282 polysilicones-15 Polymers 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*Oc1ccc(C=C(*)*)cc1)=C Chemical compound CC(*Oc1ccc(C=C(*)*)cc1)=C 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229960004106 citric acid Drugs 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004904 UV filter Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 231100000435 percutaneous penetration Toxicity 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Description
場合によっては、式(II)の1単位又は複数単位と、
(式中、
aは0、1又は2であり、
bは0、1、2、3であり、
R1は、C1−C30炭化水素基又はトリメチルシリルオキシ基、特にC1−C10アルキル基(メチル基など)であり、
R2は、水素、C1−C30炭化水素基又はトリメチルシリルオキシ基、特にC1−C10アルキル基(メチル基など)であり、
R3は、C1−8−アルキル基、特にC1−4アルキル基(エチル基など)であり、
Yは、2価C1−C10アルキレン又はC2−C10アルケニレン鎖、好ましくはC1−C4−アルキレン鎖、最も好ましくはメチレン基である)
を含む。
上記で示されるとおりの、a=1である、(Ia)、(Ib)、(Ic)及び/又は(Id)の群から選択されるs単位と、
式(IV)
(b=2である式(II)の単位に相当)のr単位と、
(式中、
sは、0から50の整数であり、
rは、0から200の整数であり、
R1、R4、R5、R6、R7は、独立して、R1に対して上記で定義されるとおりであり、
R8及びR9は、独立して、R2に対して上記で定義されるとおりであり、
B及びB’は、独立して、基R1又は
から選択されるベンザルマロネート残基であり、ただし、sが0である場合、少なくともB又はB’はベンザルマロネート残基である)
を含む、直鎖状オルガノポリシロキサンである。
ポリシリコーン−15の退色
欧州特許第1142930号明細書、実施例1で開示されるプロセスに従い調製された、ガードナー値が3.5である、600gのポリシリコーン−15試料、398.5gイソプロパノール、1gクエン酸一水和物及び0.5g過酸化水素(35%水溶液)の混合物を60℃で4から8時間、ガードナー値が約2になるまで撹拌した。減圧下(250−20mbar)で75℃にて溶媒を蒸発させ、ガードナー値が1.9である、600gのポリシリコーン−15を得た。
アスコルビン酸でのポリシリコーン−15の退色
欧州特許第1142930号明細書、実施例1で開示されるプロセスに従い調製された、ガードナー値が3.5である、600gのポリシリコーン−15試料、398.5gイソプロパノール、1gアスコルビン酸及び0.5g過酸化水素(35%水溶液)の混合物を60℃で4から8時間、ガードナー値が約2.2になるまで撹拌した。減圧下(250−20mbar)で75℃にて溶媒を蒸発させ、ガードナー値が2.2である、600gのポリシリコーン−15を得た。
Claims (9)
- ベンザルマロネートで官能化されたオルガノポリシロキサンを有機溶媒中で、過酸化水素の存在下で、グリコール酸、乳酸、酒石酸、クエン酸及びアスコルビン酸からなる群より選ばれるヒドロキシカルボン酸又はその環状エステルと接触させる工程、
及び前記有機溶媒を蒸発させる工程を含む、ベンザルマロネートで官能化されたオルガノポリシロキサンのカラーインデックスを改善するための方法。 - ベンザルマロネートで官能化された前記オルガノポリシロキサンが、前記ヒドロキシカルボン酸又はその環状エステルと接触させられた後、2.9未満のガードナー値を示す、請求項1に記載の方法。
- 前記有機溶媒が、C1−8アルキルアルコール、アセタールもしくは芳香族炭化水素又はそれらの混合物から選択される、請求項1又は2に記載の方法。
- 前記有機溶媒がイソプロパノールである、請求項1〜3のいずれか1項に記載の方法。
- 前記有機溶媒を蒸発される工程の前に、メタノール/水の混合液で洗浄する工程をさらに含む、請求項1〜4のいずれか1項に記載の方法。
- ベンザルマロネートで官能化された前記オルガノポリシロキサンが、1個の式(IIIa)の末端封鎖単位及び1個の式(IIIb)の末端封鎖単位と、
請求項6で示されるとおりの、a=1である、(Ia)、(Ib)、(Ic)及び/又は(Id)の群から選択されるs単位と、
式(IV)
のr単位と、
(式中、
sは、0から50の整数であり、
rは、0から200の整数であり、
R1、R4、R5、R6、R7は、独立して、R1に対して上記で定義されるとおりであり、
R8及びR9は、独立して、R2に対して上記で定義されるとおりであり、
B及びB’は、独立して、基R1又は
から選択されるベンザルマロネート残基であり、ただし、sが0である場合、少なくともB又はB’はベンザルマロネート残基である)
を含む直鎖状オルガノポリシロキサンである、請求項6に記載の方法。 - ベンザルマロネートで官能化された前記直鎖状オルガノポリシロキサンが、1単位の式(IIIa)及び1単位の式(IIIb)と、4から10単位の式(Ia)及び/又は(Ib)と、40から90単位の式(IV)と、から構成され(式中、R1、R2、R4、R5、R6、R7、R8、R9、B及びB’はメチルであり、Yはメチレンであり、R3はエチルである)、前記式(Ia)及び/又は(Ib)の単位が前記オルガノポリシロキサン鎖中に無作為に分布することをさらに特徴とする、請求項7に記載の方法。
- ベンザルマロネートで官能化された前記直鎖状オルガノポリシロキサンが、ポリシリコーン−15である、請求項8に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08170368A EP2192143B1 (en) | 2008-12-01 | 2008-12-01 | Novel method |
EP08170368.8 | 2008-12-01 | ||
PCT/EP2009/065970 WO2010063648A1 (en) | 2008-12-01 | 2009-11-27 | Novel method |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012510532A JP2012510532A (ja) | 2012-05-10 |
JP5522580B2 true JP5522580B2 (ja) | 2014-06-18 |
Family
ID=40602267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011537988A Active JP5522580B2 (ja) | 2008-12-01 | 2009-11-27 | 新規方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8492575B2 (ja) |
EP (2) | EP2192143B1 (ja) |
JP (1) | JP5522580B2 (ja) |
KR (1) | KR101735845B1 (ja) |
CN (1) | CN102232094B (ja) |
AT (1) | ATE523547T1 (ja) |
BR (1) | BRPI0923202B1 (ja) |
WO (1) | WO2010063648A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2780887C1 (ru) * | 2019-11-01 | 2022-10-04 | Дзе Йокогама Раббер Ко., Лтд. | Пневматическая шина |
JP7172953B2 (ja) | 2019-11-01 | 2022-11-16 | 横浜ゴム株式会社 | 空気入りタイヤ |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8497338B2 (en) * | 2011-10-31 | 2013-07-30 | Momentive Performance Materials Inc. | Process of manufacturing organosilicon products with improved quality using heterogeneous precious metal catalysts |
Family Cites Families (15)
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FR2636338B1 (fr) | 1988-09-09 | 1990-11-23 | Rhone Poulenc Chimie | Diorganopolysiloxane a fonction benzalmalonate |
GB9110123D0 (en) | 1991-05-10 | 1991-07-03 | Dow Corning | Organosilicon compounds their preparation and use |
DK0709080T3 (da) * | 1994-10-14 | 2002-05-21 | Hoffmann La Roche | Fotostabile kosmetiske lysskærmende sammensætninger |
ES2280281T3 (es) | 1994-10-14 | 2007-09-16 | Dsm Ip Assets B.V. | Nuevo benciliden malonato siloxano. |
FR2756287B1 (fr) * | 1996-11-28 | 1998-12-24 | Oreal | Nouveaux derives de filtres silicies sur leur partie aromatique, compositions cosmetiques photoprotectrices les contenant et utilisations |
FR2772030B1 (fr) * | 1997-12-04 | 2000-01-28 | Oreal | Nouveaux derives silicies de benz-x-azoles filtres, compositions cosmetiques photoprotectrices les contenant et utilisations |
FR2771926B1 (fr) * | 1997-12-04 | 2000-03-31 | Oreal | Emulsions huile-dans-eau contenant un derive de 1,3,5-triazine et une silicone copolyol et applications cosmetiques |
ES2262270T3 (es) * | 1998-07-16 | 2006-11-16 | Dsm Ip Assets B.V. | Composicion de filtro solar que contiene un agente de filtrado de radiacion uv-b de tipo polisiloxano y un agente de filtrado de radiacion uv-b de tipo bencimidazol. |
CA2288854C (en) * | 1998-11-11 | 2009-09-15 | F. Hoffmann-La Roche Ag | Novel indanylidene compounds |
EP1074244B1 (en) * | 1999-08-06 | 2006-03-08 | DSM IP Assets B.V. | Topical composition comprising a tocopherol compound |
US6489486B2 (en) * | 2000-02-21 | 2002-12-03 | Roche Vitamins Inc. | 2-hydroxyphenyl benzotriazoles as UV-A/B filters |
DE10012408A1 (de) * | 2000-03-15 | 2001-09-20 | Basf Ag | Verwendung von Lichtschutzmittelkombinationen, die als wesentlichen Bestandteil aminosubstituierte Hydroxybenzophenone enthalten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
US6346595B1 (en) * | 2000-07-07 | 2002-02-12 | Siltech Llc | Aromatic dimethicone copolyol polymers as sunscreen agents |
JP4565998B2 (ja) * | 2002-07-16 | 2010-10-20 | ディーエスエム アイピー アセッツ ビー.ブイ. | サンスクリーン |
JP2008545843A (ja) * | 2005-05-31 | 2008-12-18 | ディーエスエム アイピー アセッツ ビー.ブイ. | 新規なポリシロキサン日焼け止め剤 |
-
2008
- 2008-12-01 AT AT08170368T patent/ATE523547T1/de not_active IP Right Cessation
- 2008-12-01 EP EP08170368A patent/EP2192143B1/en active Active
-
2009
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- 2009-11-27 CN CN2009801483800A patent/CN102232094B/zh active Active
- 2009-11-27 KR KR1020117012449A patent/KR101735845B1/ko active IP Right Grant
- 2009-11-27 EP EP09763934A patent/EP2352780A1/en not_active Withdrawn
- 2009-11-27 US US13/132,136 patent/US8492575B2/en active Active
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2780887C1 (ru) * | 2019-11-01 | 2022-10-04 | Дзе Йокогама Раббер Ко., Лтд. | Пневматическая шина |
JP7172953B2 (ja) | 2019-11-01 | 2022-11-16 | 横浜ゴム株式会社 | 空気入りタイヤ |
Also Published As
Publication number | Publication date |
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US8492575B2 (en) | 2013-07-23 |
EP2192143A1 (en) | 2010-06-02 |
WO2010063648A1 (en) | 2010-06-10 |
US20120022280A1 (en) | 2012-01-26 |
CN102232094A (zh) | 2011-11-02 |
EP2192143B1 (en) | 2011-09-07 |
KR20110089413A (ko) | 2011-08-08 |
ATE523547T1 (de) | 2011-09-15 |
CN102232094B (zh) | 2013-08-14 |
BRPI0923202A2 (pt) | 2016-01-26 |
EP2352780A1 (en) | 2011-08-10 |
JP2012510532A (ja) | 2012-05-10 |
BRPI0923202B1 (pt) | 2019-07-30 |
KR101735845B1 (ko) | 2017-05-15 |
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