JP3238455B2 - 共重合体ラテックスの製造方法、共重合体ラテックスおよびそれを用いた紙塗工用組成物 - Google Patents
共重合体ラテックスの製造方法、共重合体ラテックスおよびそれを用いた紙塗工用組成物Info
- Publication number
- JP3238455B2 JP3238455B2 JP05285392A JP5285392A JP3238455B2 JP 3238455 B2 JP3238455 B2 JP 3238455B2 JP 05285392 A JP05285392 A JP 05285392A JP 5285392 A JP5285392 A JP 5285392A JP 3238455 B2 JP3238455 B2 JP 3238455B2
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- acid
- copolymer latex
- polymerization
- weight
- 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
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- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000000178 monomer Substances 0.000 claims description 53
- 238000006116 polymerization reaction Methods 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 33
- 239000012986 chain transfer agent Substances 0.000 claims description 28
- 150000002430 hydrocarbons Chemical group 0.000 claims description 16
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 6
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- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- -1 for example Chemical compound 0.000 description 32
- 238000000034 method Methods 0.000 description 30
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 4
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- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 4
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 description 4
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- BHWWTWCFLZECFZ-UHFFFAOYSA-N 2-sulfanylethyl octanoate Chemical compound CCCCCCCC(=O)OCCS BHWWTWCFLZECFZ-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- SFHANYOFMGEJCT-UHFFFAOYSA-N octyl 2-sulfanylpropanoate Chemical compound CCCCCCCCOC(=O)C(C)S SFHANYOFMGEJCT-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- KGDQKMRJLRNYEX-UHFFFAOYSA-N tridecyl 2-sulfanylpropanoate Chemical compound SC(C(=O)OCCCCCCCCCCCCC)C KGDQKMRJLRNYEX-UHFFFAOYSA-N 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 description 2
- LSZCIZOHKPPEJD-UHFFFAOYSA-N 2-sulfanylethyl hexanoate Chemical compound CCCCCC(=O)OCCS LSZCIZOHKPPEJD-UHFFFAOYSA-N 0.000 description 2
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
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- PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 description 2
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- 239000002270 dispersing agent Substances 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
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- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
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- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
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- SYDXLQBPOBUJQC-UHFFFAOYSA-N sulfanylmethyl octanoate Chemical compound CCCCCCCC(=O)OCS SYDXLQBPOBUJQC-UHFFFAOYSA-N 0.000 description 1
- LULQEGKRWUAHFD-UHFFFAOYSA-N sulfanylmethyl pentanoate Chemical compound CCCCC(=O)OCS LULQEGKRWUAHFD-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
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- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05285392A JP3238455B2 (ja) | 1992-03-11 | 1992-03-11 | 共重合体ラテックスの製造方法、共重合体ラテックスおよびそれを用いた紙塗工用組成物 |
| TW81102400A TW222649B (enrdf_load_stackoverflow) | 1992-03-11 | 1992-03-28 | |
| US07/967,741 US5354800A (en) | 1991-10-31 | 1992-10-28 | Production of copolymer latices |
| DE4236316A DE4236316A1 (en) | 1991-10-31 | 1992-10-28 | Copolymer lattices, useful as binders in paper coating compsns. - by two=stage emulsion polymerisation of monomer mixt., with hydrophilic chain transfer agent and hydrophobic agent in second stage |
| CA002081820A CA2081820A1 (en) | 1991-10-31 | 1992-10-30 | Production of copolymer latices |
| KR1019920020121A KR100250375B1 (ko) | 1991-10-31 | 1992-10-30 | 공중합체 라텍스의 제조 방법 |
| CN92112608A CN1048504C (zh) | 1991-10-31 | 1992-10-30 | 共聚物胶乳的制备 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05285392A JP3238455B2 (ja) | 1992-03-11 | 1992-03-11 | 共重合体ラテックスの製造方法、共重合体ラテックスおよびそれを用いた紙塗工用組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05255413A JPH05255413A (ja) | 1993-10-05 |
| JP3238455B2 true JP3238455B2 (ja) | 2001-12-17 |
Family
ID=12926419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05285392A Expired - Fee Related JP3238455B2 (ja) | 1991-10-31 | 1992-03-11 | 共重合体ラテックスの製造方法、共重合体ラテックスおよびそれを用いた紙塗工用組成物 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP3238455B2 (enrdf_load_stackoverflow) |
| TW (1) | TW222649B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6477700B1 (en) | 1999-03-16 | 2002-11-05 | Nec Corporation | Reticle having discriminative pattern narrower in pitch than the minimum pattern width but wider than minimum width in the pattern recognition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010106175A (ja) * | 2008-10-31 | 2010-05-13 | Asahi Kasei Chemicals Corp | 水性接着剤用共重合体ラテックスの製造方法及び水性接着剤用共重合体ラテックス |
| JP5825819B2 (ja) * | 2011-04-13 | 2015-12-02 | 住友ゴム工業株式会社 | ジエン系重合体及びその製造方法 |
| FR3002230B1 (fr) * | 2013-02-15 | 2016-02-05 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
| JP5901707B2 (ja) * | 2014-07-28 | 2016-04-13 | 旭化成ケミカルズ株式会社 | 水性接着剤 |
-
1992
- 1992-03-11 JP JP05285392A patent/JP3238455B2/ja not_active Expired - Fee Related
- 1992-03-28 TW TW81102400A patent/TW222649B/zh active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6477700B1 (en) | 1999-03-16 | 2002-11-05 | Nec Corporation | Reticle having discriminative pattern narrower in pitch than the minimum pattern width but wider than minimum width in the pattern recognition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05255413A (ja) | 1993-10-05 |
| TW222649B (enrdf_load_stackoverflow) | 1994-04-21 |
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