JPH07116128B2 - Polythiol - Google Patents
PolythiolInfo
- Publication number
- JPH07116128B2 JPH07116128B2 JP24495287A JP24495287A JPH07116128B2 JP H07116128 B2 JPH07116128 B2 JP H07116128B2 JP 24495287 A JP24495287 A JP 24495287A JP 24495287 A JP24495287 A JP 24495287A JP H07116128 B2 JPH07116128 B2 JP H07116128B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- acid
- polythiol
- pentaerythritol tetrakis
- solvent
- 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 - Fee Related
Links
- 229920006295 polythiol Polymers 0.000 title description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 2-mercaptoethyl ester Chemical class 0.000 description 4
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- ACTRVOBWPAIOHC-UHFFFAOYSA-N succimer Chemical compound OC(=O)C(S)C(S)C(O)=O ACTRVOBWPAIOHC-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-L 2-mercaptosuccinate Chemical compound OC(=O)CC([S-])C([O-])=O NJRXVEJTAYWCQJ-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規なポリチオールに関するものである。こ
れらのポリチオールは、重合調整剤、合成樹脂の原料、
架橋剤、加硫剤、エポキシ樹脂の硬化剤、酸化防止剤、
金属錯体生成剤、生化学的薬物、潤滑油添加剤等として
広範囲な用途を有するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel polythiol. These polythiols are polymerization regulators, raw materials for synthetic resins,
Crosslinking agent, vulcanizing agent, epoxy resin curing agent, antioxidant,
It has a wide range of uses as a metal complex forming agent, a biochemical drug, a lubricant additive, and the like.
〔従来の技術〕 近年ポリチオールは、樹脂の改質すなわち架橋や酸化防
止に利用され始めている。[Prior Art] In recent years, polythiols have begun to be used for resin modification, that is, for crosslinking and antioxidant.
例えば、ペンタエリスリトールテトラキス（２−メルカ
プトアセテート）および、ペンタエリスリトールテトラ
キス（３−メルカプトプロピオネート）をポリイソシア
ネートと反応させた含硫ウレタン樹脂は、ポリオレフィ
ン系樹脂に比べ、良好な諸物性を有しているが、特に屈
折率と分散のバランスの面からは未だ高度なものとは言
えない。For example, a sulfur-containing urethane resin obtained by reacting pentaerythritol tetrakis (2-mercaptoacetate) and pentaerythritol tetrakis (3-mercaptopropionate) with a polyisocyanate has better physical properties than a polyolefin resin. However, it cannot be said to be high in terms of the balance between the refractive index and the dispersion.
そこで、本発明者らは、ペンタエリスリトールテトラキ
ス（２−メルカプトアセテート）、ペンタエリスリトー
ルテトラキス（３−メルカプトプロピオネート）を用い
た場合よりもより高度の屈折率と分散特性を有し、か
つ、それら以外の諸物性でも同等又はより高度の物性を
有する樹脂原料について鋭意研究を行った。その結果、
本発明のポリチオールを用いることにより、この目的を
成就しうることを見出し、本発明に至った。Therefore, the present inventors have a higher refractive index and dispersion characteristics than the case of using pentaerythritol tetrakis (2-mercaptoacetate) and pentaerythritol tetrakis (3-mercaptopropionate), and Other than the above, the resin material having the same or higher physical properties was also earnestly studied. as a result,
It was found that this object can be achieved by using the polythiol of the present invention, and the present invention has been completed.
すなわち、本発明は、ポリウレタン樹脂の原料としても
有用な、一般式（Ｉ） （式中、Ｒは水素原子又はメルカプト基を表す。）で表
されるポリチオールを提供するものである。That is, the present invention is useful also as a raw material for polyurethane resin, represented by the general formula (I) (In the formula, R represents a hydrogen atom or a mercapto group.).
本発明の新規なポリチオールは具体的には、チオリンゴ
酸ビス（2-メルカプトエチルエステル）、2,3-ジメルカ
プトコハク酸（2-メルカプトエチルエステル）等の化合
物である。The novel polythiol of the present invention is specifically a compound such as bis (2-mercaptoethyl ester) thiomalate and 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester).
これらの化合物は、2-メルカプトエタノールとチオリン
ゴ酸、2,3-ジメルカプトコハク酸等を、無溶媒または、
溶媒中で、p-トルエンスルホン酸、硫酸、塩酸などの触
媒を加えたのち、60〜200℃に加熱し、生成する水を系
外に除去しながら反応させ、反応終了後、反応液を冷却
し、希アルカリ水溶液、水で洗浄し、溶媒を用いた場合
は、溶媒を除去して得ることができる。なお、溶媒を用
いる場合は、原料と反応性を有しないヘキサン、トルエ
ン、ベンゼン、シクロヘキサン、キシレンなどの炭化水
素類、テトラクロルエタン、クロロホルム、モンクロル
ベンゼンなどのハロゲン化炭化水素類などを使用する。These compounds, 2-mercaptoethanol and thiomalic acid, 2,3-dimercaptosuccinic acid, etc., without solvent or,
After adding a catalyst such as p-toluenesulfonic acid, sulfuric acid, hydrochloric acid in a solvent, heat it to 60-200 ° C to react while removing generated water outside the system, and cool the reaction solution after the reaction is completed. It can be obtained by washing with a dilute aqueous alkali solution and water and removing the solvent when a solvent is used. When using a solvent, use hydrocarbons such as hexane, toluene, benzene, cyclohexane, and xylene that are not reactive with the raw materials, and halogenated hydrocarbons such as tetrachloroethane, chloroform, and monchlorobenzene. .
かくして得られる本発明の新規なポリチオールは、重合
調整剤、合成樹脂の原料、架橋剤、加硫剤、エポキシ樹
脂の硬化剤、金属錯体生成剤、生化学的薬物、潤滑油添
加剤として広範囲な用途を有し、特にキシリレンジイソ
シアネート、イソホロンジイソシアネート、ヘキサメチ
レンジイソシアネートなどのポリイソシアネートと加熱
重合して得られる樹脂は、ペンタエリスリトールテトラ
キス（２−メルカプトアセテート）や、ペンタエリスリ
トールテトラキス（３−メルカプトプロピオネート）を
用いた樹脂に比べ、高度の屈折率と低分散性を有し、か
つ、その他の諸物性も良好な、光学部品などに有用な含
硫ポリウレタン樹脂である。The novel polythiol of the present invention thus obtained has a wide range of properties as a polymerization regulator, a raw material for synthetic resins, a crosslinking agent, a vulcanizing agent, a curing agent for epoxy resins, a metal complex forming agent, a biochemical drug, and a lubricating oil additive. Resins that have uses, especially those obtained by heat polymerization with polyisocyanates such as xylylene diisocyanate, isophorone diisocyanate, and hexamethylene diisocyanate are pentaerythritol tetrakis (2-mercaptoacetate) and pentaerythritol tetrakis (3-mercaptopropio A sulfur-containing polyurethane resin having a high refractive index and a low dispersibility as well as other physical properties, which is useful for optical parts and the like, as compared with a resin containing a vinyl ester).
以下実施例を示す。 Examples will be shown below.
実施例−１ チオリンゴ酸25.22g、をベンゼン100mlに懸濁させ、p-
トルエンスルホン酸0.2gを加えた後、2-メルカプトエタ
ノール27.56g加え、加熱還流させた。反応の進行に従い
生成する水を留去し、その量が5.8gとなったところで加
熱を終了した。次に５％重炭酸ソーダ水溶液で系を洗浄
したのち、水で洗浄し、ベンゼン層を硫酸ナトリウムで
乾燥後、残っている溶媒を減圧濃縮して、無色のシロッ
プ38.36gを得た。Example-1 25.22 g of thiomalic acid was suspended in 100 ml of benzene, and p-
After adding 0.2 g of toluenesulfonic acid, 27.56 g of 2-mercaptoethanol was added, and the mixture was heated under reflux. The water produced was distilled off as the reaction progressed, and heating was stopped when the amount of water reached 5.8 g. Next, the system was washed with a 5% sodium bicarbonate aqueous solution and then with water, the benzene layer was dried over sodium sulfate, and the remaining solvent was concentrated under reduced pressure to obtain 38.36 g of a colorless syrup.
Ｃ Ｈ Ｓ 元素分析値（％） 35.31 5.18 35.43 計 算 値（％） 35.54 5.22 35.57 NMR δ CDCl3 実施例２ 実施例１においてチオリンゴ酸の代わりに2,3-ジメルカ
プトコハク酸36.01gを用いた以外は、実施例１と同様に
して無色透明のシロップ40.58gを得た。C H S Elemental analysis value (%) 35.31 5.18 35.43 Calculated value (%) 35.54 5.22 35.57 NMR δ CDCl 3 Example 2 A colorless and transparent syrup (40.58 g) was obtained in the same manner as in Example 1 except that 36.01 g of 2,3-dimercaptosuccinic acid was used instead of thiomalic acid.
Ｃ Ｈ Ｓ 元素分析値（％） 31.35 4.58 41.38 計 算 値（％） 31.77 4.67 42.40 NMR δ CDCl3 使用例１ 実施例１で得られたチオリンゴ酸ビス（2-メルカプトエ
チルエステル）18.1g、ｍ−キシリレンジイソシアネー
ト18.8gを混合し、ジブチルチンラウレート0.01gを加え
均一とした後、シリコン系焼付タイプの離型剤で処理を
したガラスモールドとテフロン製ガスケットよりなるモ
ールド型中に注入した。次いで80℃で３時間、100℃で
２時間、120℃で３時間加熱した後、冷却し、モールド
から取り出した。この樹脂は屈折率1.62、アッベ数35で
あり、無色透明で加工性、耐衝撃性も良好であった。C H S Elemental analysis value (%) 31.35 4.58 41.38 Calculated value (%) 31.77 4.67 42.40 NMR δ CDCl 3 Use Example 1 18.1 g of thiomalic acid bis (2-mercaptoethyl ester) obtained in Example 1 and 18.8 g of m-xylylene diisocyanate were mixed, and 0.01 g of dibutyltin laurate was added to homogenize the mixture, followed by silicon baking. It was poured into a mold composed of a glass mold treated with a mold release agent and a Teflon gasket. Then, after heating at 80 ° C. for 3 hours, 100 ° C. for 2 hours, and 120 ° C. for 3 hours, it was cooled and taken out from the mold. This resin had a refractive index of 1.62 and an Abbe number of 35, was colorless and transparent, and had good workability and impact resistance.
比較例１ ペンタエリスリトールテトラキス（２−メルカプトアセ
テート）21.6g、ｍ−キシリレンジイソシアネート18.8g
を混合し、使用例１と同様の方法で重合を行い樹脂を得
た。得られた樹脂は、屈折率1.60、アッベ数35であり、
無色透明で加工性、耐衝撃性も良好であった。Comparative Example 1 Pentaerythritol tetrakis (2-mercaptoacetate) 21.6 g, m-xylylene diisocyanate 18.8 g
Were mixed and polymerized in the same manner as in Use Example 1 to obtain a resin. The obtained resin has a refractive index of 1.60 and an Abbe number of 35,
It was colorless and transparent, and had good workability and impact resistance.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｋ 3/00 １０６ Ｃ０８Ｇ 59/40 ＮＪＫ 65/34 ＮＱＳ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location C09K 3/00 106 C08G 59/40 NJK 65/34 NQS
Claims (1)
されるポリチオール。1. A general formula (I) (In the formula, R represents a hydrogen atom or a mercapto group.).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24495287A JPH07116128B2 (en) | 1987-09-29 | 1987-09-29 | Polythiol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24495287A JPH07116128B2 (en) | 1987-09-29 | 1987-09-29 | Polythiol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6490169A JPS6490169A (en) | 1989-04-06 |
| JPH07116128B2 true JPH07116128B2 (en) | 1995-12-13 |
Family
ID=17126397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24495287A Expired - Fee Related JPH07116128B2 (en) | 1987-09-29 | 1987-09-29 | Polythiol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07116128B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015190809A1 (en) * | 2014-06-09 | 2015-12-17 | 주식회사 케이오씨솔루션 | Novel thiol compound and polymerizable composition containing same |
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| EP1723104B1 (en) | 2004-02-17 | 2010-11-10 | Chevron Phillips Chemical Company Lp | Sulfur-containing compositions and processes for making same |
| US8003748B2 (en) | 2004-02-17 | 2011-08-23 | Chevron Phillips Chemical Company, Lp | Polythiourethane compositions and processes for making and using same |
| CA2619316A1 (en) | 2005-08-16 | 2007-02-22 | Chevron Phillips Chemical Company Lp | Polymer compositions and processes for making and using same |
| WO2007022217A1 (en) | 2005-08-16 | 2007-02-22 | Chevron Phillips Chemical Company Lp | Mercaptan-hardened epoxy polymer compositions and processes for making and using same |
| EP3483220B1 (en) | 2013-09-30 | 2020-08-05 | Hoya Lens Thailand Ltd. | Transparent plastic substrate and plastic lens |
-
1987
- 1987-09-29 JP JP24495287A patent/JPH07116128B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015190809A1 (en) * | 2014-06-09 | 2015-12-17 | 주식회사 케이오씨솔루션 | Novel thiol compound and polymerizable composition containing same |
| CN106458876A (en) * | 2014-06-09 | 2017-02-22 | 可奥熙搜路司有限公司 | Novel thiol compounds and polymerizable compositions containing them |
| CN106458876B (en) * | 2014-06-09 | 2018-06-05 | 可奥熙搜路司有限公司 | Novel thiol compounds and polymerizable compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6490169A (en) | 1989-04-06 |
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