GB837704A - Improvements in or relating to thermoplastic mixtures of copolymers - Google Patents
Improvements in or relating to thermoplastic mixtures of copolymersInfo
- Publication number
- GB837704A GB837704A GB21194/56A GB2119456A GB837704A GB 837704 A GB837704 A GB 837704A GB 21194/56 A GB21194/56 A GB 21194/56A GB 2119456 A GB2119456 A GB 2119456A GB 837704 A GB837704 A GB 837704A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- cross
- copolymer
- copolymers
- vinyl
- 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
- 229920001577 copolymer Polymers 0.000 title abstract 8
- 239000000203 mixture Substances 0.000 title abstract 5
- 229920001169 thermoplastic Polymers 0.000 title abstract 5
- 239000004416 thermosoftening plastic Substances 0.000 title abstract 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 6
- 238000004132 cross linking Methods 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 5
- 239000000178 monomer Substances 0.000 abstract 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 3
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005521 carbonamide group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 229920001198 elastomeric copolymer Polymers 0.000 abstract 2
- 229920013728 elastomeric terpolymer Polymers 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 abstract 2
- 229920000126 latex Polymers 0.000 abstract 2
- -1 methylol derivatives of acrylamide Chemical class 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- NTQDHUATINPOQS-UHFFFAOYSA-N (4,5-dihydroxy-2-methylpent-2-en-3-yl) prop-2-enoate Chemical compound C(C=C)(=O)OC(C(O)CO)=C(C)C NTQDHUATINPOQS-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- YNUIGWRKJHQRGL-UHFFFAOYSA-N 1-(2-ethenoxyethyl)-1-ethylurea Chemical compound C(=C)OCCN(C(=O)N)CC YNUIGWRKJHQRGL-UHFFFAOYSA-N 0.000 abstract 1
- ZDFSVUUSSAXGJE-UHFFFAOYSA-N 1-cyclohexyl-1-(2-ethenoxyethyl)urea Chemical compound C1(CCCCC1)N(C(=O)N)CCOC=C ZDFSVUUSSAXGJE-UHFFFAOYSA-N 0.000 abstract 1
- OMNYXCUDBQKCMU-UHFFFAOYSA-N 2,4-dichloro-1-ethenylbenzene Chemical class ClC1=CC=C(C=C)C(Cl)=C1 OMNYXCUDBQKCMU-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- BPAZCWSPOCHLKP-UHFFFAOYSA-N 3-ethenoxypropylurea Chemical compound NC(=O)NCCCOC=C BPAZCWSPOCHLKP-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- 241000694440 Colpidium aqueous Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 230000015271 coagulation Effects 0.000 abstract 1
- 238000005345 coagulation Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- 229920001897 terpolymer Polymers 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/16—Homopolymers or copolymers of alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
- C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/12—Copolymers of styrene with unsaturated nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
- C08L21/02—Latex
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
A thermoplastic composition comprises (1) an elastomeric terpolymer of butadiene or homologue or derivative thereof and acrylonitrile with a minor proportion of a further ethylenically-unsaturated monomer to which, in the polymer, is attached a self-cross-linking group and optionally divinyl benzene, glycol diacrylate or vinyl chloride; and (2) a thermoplastic copolymer of 95-55 parts by weight of styrene or a nuclear-substituted derivative thereof and 5-45 parts of acrylonitrile; the terpolymer (1) being present as 10 to 75% by weight of the composition and part of the copolymer (2) optionally being replaced by polyvinyl chloride or a copolymer of vinyl chloride with vinylidene chloride or vinyl acetate. The elastomeric terpolymer may be made by copolymerizing butadiene or isoprene, acrylonitrile, and an unsaturated monomer carrying the requisite self-cross-linking groups by which is to be understood groups which effect crosslinking when heated to 100-220 DEG C. and which may be carbonyl groups such as carboxyl, carbonamide and aldehyde groups; methylol and methylol ether groups; dioxolane groups; ureido groups; and groups of the formula <FORM:0837704/IV (a)/1> where R4 and R5 each stand for a hydrocarbon residue which may be bound to the carbonyl group through an oxygen atom. A large number of general classes of compounds are referred to and the following specific examples: acrylic acid, a -chloromethacrylic acid, methacrylic acid, crotonic acid, sorbinic acid, cinnamic acid, mono-alkyl esters of acrylamide, methacrylamide, acrolein, methacrolein, alkyl ethers of the methylol derivatives of acrylamide, isopropylidene-glyceryl acrylate and methacrylate, methylene glyceryl acrylate and methacrylate, b -ureidoethyl acrylate and methacrylate, b -ureidoethyl vinyl ether, 3-ureido-n-propyl vinyl ether, b -ureido-isobutyl vinyl ether, N-(2-vinyl-oxyethyl) - N1 - cyclohexyl urea, N - (2 - vinyl-oxyethyl)-N1-ethyl urea, and the methylene derivatives of malonic acid esters, ethyl acetoacetate and acetyl acetone. The self-cross-linking group can also be introduced into the copolymer by reacting polymers containing copolymers containing carbonamide groups with formaldehyde, if desired in the presence of an alcohol to introduce methylol or methylol ether groups. These elastomeric copolymers preferably contain 5-45 wt. per cent of acrylonitrile and 0.1-20 wt. per cent of monomers with self-cross-linking groups, the rest being butadiene; these copolymers are converted into an insoluble gel by heating for a short time. They are prepared by standard emulsion polymerization. Additional cross-linking monomers, such as divinyl benzene and glycol diacrylate, and additional monomers such as vinyl chloride, may also be copolymerized. The thermoplastic copolymer may also be prepared by emulsion polymerization. Suitable styrene derivatives are 2-chloro-, 4-chloro- and 2,4-dichloro-styrenes. The blending of the copolymers is carried out by mixing the latices of the copolymers as obtained by emulsion polymerization and the mixture coagulated by known methods, washed, dried, and cross-linked by heating to 100-220 DEG C. Aqueous emulsions or dispersions of pigments, stabilizers and plasticizers may be added to the mixed latices before coagulation, and in the examples, titanium dioxide is added to the blends. Alternatively the elastomeric copolymer may be cross-linked and thereafter mixed with the thermoplastic copolymer. Numerous examples are given.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE837704 | 1955-07-09 | ||
| DE865374X | 1958-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB837704A true GB837704A (en) | 1960-06-15 |
Family
ID=25749846
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21194/56A Expired GB837704A (en) | 1955-07-09 | 1956-07-09 | Improvements in or relating to thermoplastic mixtures of copolymers |
| GB19757/59A Expired GB865374A (en) | 1955-07-09 | 1959-06-09 | Improvements in or relating to thermoplastic mixtures of copolymers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19757/59A Expired GB865374A (en) | 1955-07-09 | 1959-06-09 | Improvements in or relating to thermoplastic mixtures of copolymers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1078324B (en) |
| GB (2) | GB837704A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004776A3 (en) * | 1978-04-06 | 1979-10-31 | Monsanto Company | Thermoplastic compositions comprising blends of styrene-acrylonitrile resin and nitrile rubber, and a process for their production |
| EP0281080A1 (en) * | 1987-03-05 | 1988-09-07 | Polysar Limited | Thermoplastic rubber compositions |
| EP0990465A3 (en) * | 1998-10-01 | 2000-08-30 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Decomposition type reactive emulsifier and polymer-modifying method using the same |
-
0
- DE DENDAT1078324D patent/DE1078324B/en active Pending
-
1956
- 1956-07-09 GB GB21194/56A patent/GB837704A/en not_active Expired
-
1959
- 1959-06-09 GB GB19757/59A patent/GB865374A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004776A3 (en) * | 1978-04-06 | 1979-10-31 | Monsanto Company | Thermoplastic compositions comprising blends of styrene-acrylonitrile resin and nitrile rubber, and a process for their production |
| EP0281080A1 (en) * | 1987-03-05 | 1988-09-07 | Polysar Limited | Thermoplastic rubber compositions |
| EP0990465A3 (en) * | 1998-10-01 | 2000-08-30 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Decomposition type reactive emulsifier and polymer-modifying method using the same |
| US6307069B1 (en) | 1998-10-01 | 2001-10-23 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | 1,2 - Dioxolane decomposition reactive emulsifier and polymer-modifying method using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1078324B (en) | 1960-03-24 |
| GB865374A (en) | 1961-04-19 |
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