PT80850B - PROCESS FOR THE PREPARATION OF CURVED LIQUID COMPOSITIONS OF EPOXY-FINISHED POLYMERS AND MERCAPTAN - Google Patents

PROCESS FOR THE PREPARATION OF CURVED LIQUID COMPOSITIONS OF EPOXY-FINISHED POLYMERS AND MERCAPTAN Download PDF

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Publication number
PT80850B
PT80850B PT80850A PT8085085A PT80850B PT 80850 B PT80850 B PT 80850B PT 80850 A PT80850 A PT 80850A PT 8085085 A PT8085085 A PT 8085085A PT 80850 B PT80850 B PT 80850B
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PT
Portugal
Prior art keywords
mercaptan
process according
epoxy
terminated polymer
terminated
Prior art date
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PT80850A
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Portuguese (pt)
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PT80850A (en
Inventor
Timothy Charles Philip Lee
Thomas P Ross
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Morton Thiocol Ltd
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Application filed by Morton Thiocol Ltd filed Critical Morton Thiocol Ltd
Publication of PT80850A publication Critical patent/PT80850A/en
Publication of PT80850B publication Critical patent/PT80850B/en

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  • Epoxy Resins (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Stable liquid adduct compositions are prepared by an addition reaction between epoxy-terminated polymers and mercaptan-terminated polymers. One of the polymers is in stoichiometric excess so that the composition has free epoxy or mercaptan functional groups. The liquid polymer composition can be stored for long periods before curing with a curing agent reactive with the free functional groups.

Description

Descrição Viscosidade Partes em peso do ageii

química 25°C te de cura para 100

partes de:

(a) ADUTO (b) ΕΡΟΧΙ N0 CON TROLO Anchor 1608 Aduto amina, alifatica liquido 36 12,5 25 Ancamina 1768 Amina alifatica liquida activada 3 10 20 Ancamida 502 Amina amido alifatica liquida 3,5 25 50 Ancamina MCA Amina ciclo-alifatica liquida 2,5 27,5 55 Trietilenetetramina Amina alifatica liquida 5 10

OS OBJECTIVOS DO ESTUDO DE CURA FORAM:

1. Observar a miscibi1 idade do agente de cura com a resina durante a mistura

2. Medir o tempo de gel, tempo livre de junção e exotermia de cada sistema agente de cura/resina.

3. Medir a dureza da cura destes sistemas.

4. Medir o aumento do volume dos produtos curados depois de imersão em água â temperatura ambiente e 60°C.

V

-53V

Até agora foram estudados os

seguintes Adutos e as correspondentes resinas de controlo.

EPIKOTE 816 + LP-3 EPIKOTE 816 + LP-33 EPIKOTE 213 + LP-3 EPIKOTE 213 + LP-33

Os resultados do estudo de

cura são indicados nos Quadros 17 a 28 e resumidos abaixo. Dependendo da propriedade requerida, são feitas recomendações sobre a selecção dos agentes curativos £ partir dos que foram estudados.

ADUTO EPOXI EM EXCESSO EPIKOTE 816 + LP-3 1:1

EPIKOTE 816 + LP-3 1:1

Parâmetros

Aduto optimo/miscibilidade do Curativo Cura Rápida

Resistência óptima à agua

Agente cura recomendado

Anchor 1608 Ancamine MCA

Anchor 1608

Tetraetileno tetramina

Ancamina 1768, Ancamida 502 a Trietileno tetramina com imersão a 60°C e Trietileno tetramina com imersão a 22°C

ADUTO EPOXI EM EXCESSO EPIKOTE 816 + LP-33 1:1

Parametro Agente de cura recomendado

Aduto optimo/Miscibi1 idade

do Curativo Anchor 1608

Cura rápida Anchor 1608

Resistência óptima à agua Trietileno Tetramina

ou Ancamina 1768 com imersão a 60°C Trietileno tetramina ou ancamina 1768 ou ancamina 50 a 22°C

9 ·

ADUTO EPOXI EM EXCESSO EPIKQTE 213 + LP-3 1:1

Parametro Agente de cura recomendado

} Aduto óptimo/miscibi1 idade do Curativo Anchor 1608

Ancamina MCA

Cura rapida Anchor 1608

Resistência óptima à agua Ancamida 502 ou TrieI tileno tetramina

' com imersão a 60°C

Ancamina 1768 com imersão a 22°C

ADUTO EPOXI EM EXCESSO EPIKQTE 213 + LP-33 1:1

Parametro

Agente de cura recomendado

Aduto óptimo/miscibi1 idade

do Curativo Anchor 1608

Ancamida 502

Cura rapida Anchor 1608

Resistência óptima â agua Trietileno tetramina

com imersão a 60°C Ancamina 1768 com imersão a 22°C

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68Exemplo 18

Foram testadas as propriedades fisicas de um aduto Epikote 1001 + LP-33 1:0,25. 0 aduto

foi avaliado como um revestimento não preenchido, aplicado com espátula, em placas de aço macio com projecção por descarga. O revestimento foi curado com Ancamina 1608, uma amina?. alifática. As caracteristicas da cura do revestimento são indicados no Quadro que se segue:

ADUTO CONTEÚDO EM ANCAMINA TEMPO LIVRE DE EPOXIDO DO NIVEL 1608 FIXAÇÃO DE PELI ADUTO phr CULA FINA MOLES KG-1

EPIKOTE 1001 + LP-33 1:0,25 1,03 4,12

Foram preparadas duas amostras do aduto, diferindo apenas na espessura do revestimento.

As amostras avaliadas, quanto à adesão, impacto, pulverização salina e resistência UV.

) Os resultados do teste são indicados como se segue:

AMOSTRA B

AMOSTRA A

Espessura do revestimento (u) 300-350

da adesão desenvolvimento-cru

zado* 0

Impacto inverso (lbs polegada) 160

Impacto directo (libs polegada) 160

110-260

0

160

80

DEPOIS DE 312 HORAS DE EXPOSIÇÃO A UV

Desenvolvimento-cruzado da adesão 0

Impacto inverso (lbs polegada) 160

DEPOIS DE 200 HORAS DE EXPOSIÇÃO A PULVERIZAÇÃO SALINA

Desenvolvimento cruzado da adesão 0

Proteccão à Corrosão Sem aumento da

corrosão

sem perda de adesão

Sem perda de flexibilidade

" O desenvolvimento-cruzado da adesão é avaliado numa escala graduada de zero a seis. Uma leitura de zero indica adesão excelente. Uma leitura de seis = pouca adesão.

MICROESTRUTURA DO ADUTO

Amostras curadas do Aduto Epoxi em Excesso Epikote 213 + LP-33 1:1 e o controlo Epikote 213 + LP-33 1:1 foram submetidas a exame por Microscopia Electrónica de Transmissão quanto à sua microestrutura.

Foram analisadoas três amostras:

a) Controlo Epikote 213 +LP-33 1:1 curado à temperatura ambiente com 10 pbw de EH-330.

b) Aduto Epoxi em Excesso Epikote 213 + LP-33 1:1 ourado â temperatura ambiente com 10 pbw de EH-330.

c) Aduto Epoxi em Exeesso Epikote 213 + LP-33 1:1 curado durante 1 hora a 60°C com 10 pbw de EH-330.

Preveniu-se que as três amostras revelariam uma microestrutura diferente devido aos seus diferentes métodos de manufactura e temperaturas da cura.

Os resultados do teste são os seguintes:

1. Todas as amostras têm uma microestrutura indicativa de materiais de duas fases.

2. A fase dispersa que se pensa ser LP-33 tem uma dispersão mais fina na amostra de Aduto Epoxi em Excesso curada à temperatura ambiente. O grau de dispersão foi avaliado na seguinte ordem:

Aduto Curado à Temp. Ambiente"^, Controlo LP/Epoxi^ Aduto Curado a 60°C.

Description Viscosity Parts by weight of ageii

chemistry 25 ° C cure for 100

parts of:

(a) ADUTO (b) ΕΡΟΧΙ N0 WITH TROLLE Anchor 1608 Amine adduct, liquid aliphatic 36 12.5 25 Ancamina 1768 Activated liquid aliphatic amine 3 10 20 Ancamida 502 Amine liquid aliphatic starch 3.5 25 50 Ancamina MCA Liquid cycloaliphatic amine 2.5 27.5 55 Triethylenetetramine Liquid aliphatic amine 5 10

THE OBJECTIVES OF THE HEALING STUDY WERE:

1. Observe the miscibility of the curing agent with the resin during mixing

2. Measure the gel time, free time of binding and exotherm of each curing agent / resin system.

3. Measure the cure hardness of these systems.

4. Measure the volume increase of the cured products after immersion in water at room temperature and 60 ° C.

V

-53V

So far we have studied the

Adducts and the corresponding control resins.

EPIKOTE 816 + LP-3 EPIKOTE 816 + LP-33 EPIKOTE 213 + LP-3 EPIKOTE 213 + LP-33

The results of the

curves are given in Tables 17 to 28 and summarized below. Depending on the required properties, recommendations are made on the selection of curative agents from those studied.

ADUXE EPOXY IN EXCESS EPIKOTE 816 + LP-3 1: 1

EPIKOTE 816 + LP-3 1: 1

Parameters

Aduto optimal / Miscibility of Healing Fast Healing

Optimal water resistance

Healing agent recommended

Anchor 1608 Ancamine MCA

Anchor 1608

Tetraethylene tetramine

Ancamina 1768, Ancamida 502 to Triethylene tetramine with immersion at 60 ° C and Triethylene tetramine with immersion at 22 ° C

ADUXE EPOXY IN EXCESS EPIKOTE 816 + LP-33 1: 1

Parameter Healing agent recommended

Optimal adduct / Miscibi1 age

of Anchorage 1608

Fast Healing Anchor 1608

Optimal water resistance Trietileno Tetramina

or Ancamine 1768 with immersion at 60 ° C Trietileno tetramina or ancamina 1768 or ancamina 50 at 22 ° C

9

EPOXY ADHESIVE IN EXCESS EPIKQTE 213 + LP-3 1: 1

Parameter Healing agent recommended

} Optimum adduct / miscibility of Anchorage 1608

Ancamina MCA

Healing fast Anchor 1608

Optimal water resistance Ancamide 502 or TrieI tylene tetramine

with immersion at 60 ° C

Ancamina 1768 with immersion at 22 ° C

EPOXY ADHESIVE IN EXCESS EPIKQTE 213 + LP-33 1: 1

Parameter

Healing agent recommended

Optimum adduct / miscibility

of Anchorage 1608

Ancamida 502

Healing fast Anchor 1608

Optimal resistance to water Triethylene tetramine

with immersion at 60 ° C Ancamina 1768 with immersion at 22 ° C

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tO

ro Ό • i-1 ro C 1 · in 1 W ro r- 3 And the t to to to ro s. (I.e. to + -> AND O O to 10 clone O O ro to AND Cu s- < ro to O (I.e. (I.e. AND ro δ- έη fO (I.e. W rt + j Π3 U3 W £ r ro 1 (I.e. to ω (I.e. t3 τ-

<·. ro 00 ..... The ro T rH

H LU O · » '- F- +> (I.e. <#> ro r-1 C * J Z CO AND LU (I.e. 3 l-1 AND 1 '· " CO 3 O < > < < IO O QC Rt 3) The H cu δ- < (I.e. QC X? AND LU • 1-4 Π3 AND ' ass ro Z5 (I.e. s Not to cn O) q *W LU φ να S- H ro 1- EU ro m (N ro 3 Π3 AND < (I.e. W: O K r-1 to frog there • fH LU Q 1 ξ; T3 -rt AND 1-1 W (I.e. Φ · (-t cn N δ- O ro 00 Ro ια co tO L. 5_ AND => 3 a u QJ <0. ro (I.e. Φ h; u • 3 + j - 3 c υ The CL 5 00 υ o oo 0 LO 0 · -T C cr- C ° cn_2 (- rtj r4 5 rd <in <-σ

the iro ω to o s_ Ο · φ E

ro

O

σ ω

ro xj

cn to Φ c -F 5 it)

c ε - φ Μ Μ Φ Q

Trieethylene '73A 19a 1 t 5 73a 20D

tatramina

67o

0 + J Φ cos fm cn Φ XI 3 ·. e Γ- = o <>' tfp (I.e.

ro

ADUTO EPIKOTE 213 + LP-33

0 (I.e. LD • ri! (OOM < Cl sφ Cl (O O XJ ε = 3 e * < • rH cn φ LO ro νσ σ> CC N. (/) yl) The W < LU (I.e. ie ro 00 «3 · s s- ε W e LD ro * 3 3 Q '-

Hardness of initiation cure margin 42D 30Α 15D 0 + j φ c ε (I.e. νο • * 3 Φ 3 ε φ · - <3 tJ ο <#> Ί3 · (I.e. (I.e. LU <c> H z , Λ ° LU ω ! <α * J- < <o co The ι- Σ 9- φ • < φ ε e U · <· -ι ί U φ * < 3 σ) cc Ι / J OJ Ν <Φ «α E. < W j Π3 ιη o (I.e. 1- ue W (I.e. Γ- ė < 03 03 cc - 5 - - SZ LU Q CL s: LU (I.e. 1- Φ ο • σ * < W e ro · ή φ 0 (I.e. 07 K Ro L- or *W α CZ) 5- Π3 (I.e. (I.e. ιη <ν * 23 23 ι-ι 53> η rH LU ουυr

(I.e.

+ J

W

(I.e.

στ

R

φ

XJ

ro

s_

3

O

/ triethylene 28D 71A 1.3 28D

tetramine 1

Example 18

The physical properties of an Epikote 1001 + LP-33 1: 0.25 adduct was tested. 0 aduto

was evaluated as an unfilled, spatula-coated coating on soft steel plates with discharge projection. The coating was cured with Ancamine 1608, an amine. aliphatic. The coating cure characteristics are set forth in the following Table:

ADUTO CONTENTS OF ANCAMINE FREE TIME EPOXIDE OF LEVEL 1608 PELI FIXATION ADUTO phr FINE CUL MOLES KG -1

EPIKOTE 1001 + LP-33 1: 0.25 1.03 4.12

Two samples of the adduct were prepared, differing only in the thickness of the coating.

The samples evaluated for adhesion, impact, saline spray and UV resistance.

) The test results are indicated as follows:

SAMPLE B

SAMPLE A

Coating thickness (u) 300-350

of development-raw adhesion

* 0

Reverse Impact (lbs.) 160

Direct impact (libs inch) 160

110-260

0

160

80

AFTER 312 HOURS OF UV EXPOSURE

Cross-compliance development 0

Reverse Impact (lbs.) 160

AFTER 200 HOURS OF EXPOSURE TO SALINE SPRAYING

Cross-compliance development 0

Protection against Corrosion Without

corrosion

without loss of adhesion

No loss of flexibility

"The cross-development of adhesion is evaluated on a graded scale from zero to 6. A reading of zero indicates excellent adhesion, a reading of six = low adhesion.

ADULT MICROSTRUCTURE

Cured samples of the Epikote 213 + LP-33 1: 1 Excess Epoxy Adduct and the 1: 1 Epikote 213 + LP-33 control were submitted to Transmission Electron Microscopy for its microstructure.

Three samples were analyzed:

a) Control Epikote 213 + LP-33 1: 1 cured at room temperature with 10 bp of EH-330.

b) Epoxy Adduct in Excess Epikote 213 + LP-33 1: 1 at room temperature with 10 pbw of EH-330.

c) Epoxy Adduct in Exeesso Epikote 213 + LP-33 1: 1 cured for 1 hour at 60 ° C with 10 bp of EH-330.

The three samples were predicted to exhibit a different microstructure due to their different manufacturing methods and cure temperatures.

The test results are as follows:

1. All samples have a microstructure indicative of two-phase materials.

2. The dispersed phase which is thought to be LP-33 has a finer dispersion in the sample of Excess Epoxy Adduct cured at room temperature. The degree of dispersion was evaluated in the following order:

Cure Adduct at Temp. Ambient ", LP / Epoxy Control. Adduct Cured at 60 ° C.

Claims (23)

REIVINDICAÇÕES lâ.- Processo para prepararA process for preparing uma composição polimérica curável caracterizado por se fazer reagir um polimero com terminação epoxi tendo pelo menos dois grupos epoxi por molécula com um polímero com terminação mercaptano tendo pelo menos dois grupos mercaptano por molécula, em que um dos referidos polímeros está em excesso estoiquiométrico pelo que o produto final contem um copolímero liquido curável tendo grupos livres epoxi ou mercaptano e tendo uma viscosidade estável antes de ser curado.a curable polymer composition comprising reacting an epoxy-terminated polymer having at least two epoxy groups per molecule with a mercaptan-terminated polymer having at least two mercaptan groups per molecule, wherein one of said polymers is in excess of a stoichiometric amount; final product contains a curable liquid copolymer having free epoxy or mercaptan free groups and having a stable viscosity before being cured. 2ã.- Processo de acordo com a reivindicação 1, caracterizado por a reacção ser efectuada na ausência de um catalisador.2. A process according to claim 1, wherein the reaction is carried out in the absence of a catalyst. 3&.- Processo de acordo com aProcess according to claim 1, reivindicação 1 ou 2, caracterizado por o referido polímero com terminação epoxi ter um conteúdo de epóxido de 2 a 6 moles/kg.Claim 1 or 2, characterized in that said epoxy-terminated polymer has an epoxide content of 2 to 6 moles / kg. 4ê.- Processo de acordo com qual^ quer uma das reivindicações anteriores caracterizado por o referido polimero com terminação epoxi ser uma resina epoxi.4. A process according to any one of the preceding claims wherein said epoxy terminated polymer is an epoxy resin. 5â.- Processo de acordo com a reivindicação 4, caracterizado por a referida resina epoxi ser uma resina sólida.5. A process according to claim 4, wherein said epoxy resin is a solid resin. 6ã.- Processo de acordo com a reivindicação 3 ou 4, caracterizado por o referido polimero com terminação epoxi ser uma resina liquida tendo uma viscosidade variando entre 0,5 e 20 Pas.6. A process according to claim 3 or 4, wherein said epoxy terminated polymer is a liquid resin having a viscosity ranging from 0.5 to 20 Pas. 7ã.- Processo de acordo com qualquer uma das reivindicações anteriores caracterizado por o referido polimero com terminação epoxi ter um peso molecular médio de 250 a 600.7. A process according to any one of the preceding claims wherein said epoxy terminated polymer has an average molecular weight of from 250 to 600. 8&._ Processo de acordo com qualquer uma das reivindicações anteriores caracterizado por o polímero com terminação mercaptano ser um poli-sulfeto líquido.The process according to any one of the preceding claims characterized in that the mercaptan terminated polymer is a liquid poly-sulphide. 9a.- Processo de acordo com9. A method according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o referido polimero com terminação mercaptano ter uma viscosidade entre 0,5 e 2,5 Pas.any of the preceding claims characterized in that said mercaptan terminated polymer has a viscosity between 0.5 and 2.5 Pas. 10a._ Processo de acordo comMethod according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o referido polímero com terminação mercaptano ter um peso molecular médio de 500 a 12.000.any of the preceding claims characterized in that said mercaptan-terminated polymer has an average molecular weight of 500 to 12,000. lia.- Processo de acordo com a reivindicação 10, caracterizado por o referido polimero com terminação mercaptano ter um peso molecular médio de 500 a 2.000.11. A process according to claim 10, wherein said mercaptan terminated polymer has an average molecular weight of 500 to 2,000. 12a.- Processo de acordo com12. A method according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o referido polímero com terminação mercaptano ter uma média de 2 a 2,5 grupos mercaptano por molécula.any one of the preceding claims characterized in that said mercaptan terminated polymer has a mean of 2 to 2.5 mercaptan groups per molecule. 13a.- Processo de acordo com13. A method according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o referido polímero com terminação mercaptano ter um: conteúdo de mercaptano de 1,5 a 2,5 mole/kg.any one of the preceding claims characterized in that said mercaptan-terminated polymer has a: mercaptan content of 1.5 to 2.5 mol / kg. ' -73}.'-73}. ί -------.н -------. 14§.- Processo de acordo com qualquer uma das reivindicações anteriores caracterizado por a reacção ter lugar a uma temperatura entre 10 e 120°C.14. A process according to any one of the preceding claims wherein the reaction takes place at a temperature between 10 and 120 ° C. 15§.- Processo de acordo com15. Method according to qualquer uma das reivindicações anteriores caracterizado por a relação entre os grupos epóxidos nos polímeros com terminação epoxi e os grupos mercaptano nos polimeros com terminação mercaptano variar entre 2:1 e 7,5:1.any one of the preceding claims characterized in that the ratio of the epoxy groups in the epoxy-terminated polymers to the mercaptan groups in the mercaptan terminated polymers is from 2: 1 to 7.5: 1. 16ã.- Processo de acordo com a reivindicação 15, em que a referida relação molar varia entre 2:1 e 5:1.16. The process of claim 15, wherein said molar ratio ranges from 2: 1 to 5: 1. 17^.- Processo de acordo com17. A process according to claim 1, qualquer uma das reivindicações anteriores caracterizado por que a relação molar entre os grupos mercaptano nos polímeros com terminação mercaptano e os grupos epoxi nos polímeros com terminação epóxido variar entre 1,5:1 e 3:1.any one of the preceding claims characterized in that the molar ratio of the mercaptan groups in the mercaptan terminated polymers and the epoxy groups in the epoxide terminated polymers is from 1.5: 1 to 3: 1. 18^.- Processo de acordo com18. A process according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o copolímero liquido resultante ter uma viscosidade de 100 Pas ou menos a 25°C.any of the preceding claims characterized in that the resulting liquid copolymer has a viscosity of 100 Pas or less at 25 ° C. 19§.- Processo de acordo com a reivindicação 18, caracterizado por o copolímero liquido resultante ter uma viscosidade de 60 Pas ou menos a 25°C.19. A process according to claim 18, wherein the resultant liquid copolymer has a viscosity of 60 Pas or less at 25 ° C. 20^.- Processo de acordo com20. A process according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o copolímero liquido resultante ter um peso molecular varian do entre 1.600 e 5.000.any of the preceding claims characterized in that the resulting liquid copolymer has a molecular weight ranging from 1,600 to 5,000. 21§.- Processo de acordo com a reivindicação 20, caracterizado por o copolímero liquido re·21. A process according to claim 20, characterized in that the liquid copolymer re -74sultante ter um peso molecular de não mais de que 3.000.It has a molecular weight of no more than 3,000. 22ã.- Processo de acordo com22. A process according to qualquer uma das reivindicações anteriores caracterizado por o componente principal do copolimero liquido resultante se apresentar sob a forma de um copolimero de bloqueio ABA.any one of the preceding claims characterized in that the main component of the resulting liquid copolymer is in the form of an ABA block copolymer. 23^.- Processo de acordo com23. A process according to claim 1, qualquer uma das reivindicações anteriores caracterizado por o produto de reacção ser armazenado sob a forma de um pré-polímero líquido não-cruzado e subsequentemente curado com um agente de cura de modo a formar um produto sólido.any of the preceding claims characterized in that the reaction product is stored in the form of a non-cross-linked liquid prepolymer and subsequently cured with a curing agent to form a solid product. 24^.- Processo de acordo com24. A process according to claim 1, a reivindicação 23, caracterizado por o pré-polímero liquido ter grupos epoxi livres e o referido agente de cura ser um catalisador amina.Claim 23, characterized in that the liquid prepolymer has free epoxy groups and said curing agent is an amine catalyst.
PT80850A 1984-07-26 1985-07-23 PROCESS FOR THE PREPARATION OF CURVED LIQUID COMPOSITIONS OF EPOXY-FINISHED POLYMERS AND MERCAPTAN PT80850B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848419036A GB8419036D0 (en) 1984-07-26 1984-07-26 Liquid copolymers
GB08517361A GB2162189B (en) 1984-07-26 1985-07-09 Curable liquid compositions of epoxy-and mercaptan-terminated polymers

Publications (2)

Publication Number Publication Date
PT80850A PT80850A (en) 1985-08-01
PT80850B true PT80850B (en) 1987-09-30

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CA (1) CA1255040A (en)
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NO (1) NO164779C (en)
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KR100685952B1 (en) 2002-03-19 2007-02-23 엘지.필립스 엘시디 주식회사 Substrate for Liquid Crystal Display Device, Liquid Crystal Display, and Method of manufacturing the same
DE10320543B4 (en) * 2003-05-07 2006-02-02 Thioplast Chemicals Gmbh & Co.Kg Process for the preparation of prepolymers based on polysulfides and polyepoxides

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US2789958A (en) * 1951-10-30 1957-04-23 Thiokol Chemical Corp Resinous reaction products of polyepoxides and polysulfide polymers and methods of making the same
GB787022A (en) * 1952-12-20 1957-11-27 Minnesota Mining & Mfg Improvements in or relating to self-hardening, liquid resinous compositions and articles having the resinous composition bonded thereto
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NO852951L (en) 1986-01-27
JPH0432087B2 (en) 1992-05-28
NO164779B (en) 1990-08-06
AU4518085A (en) 1986-01-30
DK339785D0 (en) 1985-07-25
CA1255040A (en) 1989-05-30
IN164412B (en) 1989-03-18
PT80850A (en) 1985-08-01
DK339785A (en) 1986-01-27
JPS63314233A (en) 1988-12-22
NZ212727A (en) 1988-09-29
NO164779C (en) 1990-11-14

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